15 May 2023

📚 Wherever You Go, There You Are

From Jon Kabat-Zinn’s Wherever You Go, There You Are:

Meditation is simply about being yourself and knowing something about who that is. It is about coming to realize that you are on a path whether you like it or not, namely, the path that is your life. Meditation may help us see that this path we call our life has direction; that it is always unfolding, moment by moment; and that what happens now, in this moment, influences what happens next.

I lucked into reading this book at the right time, when I was ready to do the work it proposes and open to the possibilities it presents. I found it to be a gentle and nurturing introduction to mindfulness — “paying attention in a particular way: on purpose, in the present moment, and nonjudgmentally” — and a practical overview of how to cultivate it through meditation. I also found it to be a peaceful companion to pick up and just enjoy “the bloom of the present moment” with. I’d find myself looking forward to when I could pause to share time with this book.

It guided me, in an unstructured way, into meditating. I’d read a bit of the book and then try meditating. Or, I’d try meditating and then read a bit of the book. The line between the two could blur, and reading the book slowly, carefully, and openly became a bit like (I at least imagine, having never participated in one…) a guided meditation session in itself.

This book has provided some serious upgrades to my thinking, perceiving, and ultimately, being.

It gave me some powerful visual metaphors: imagining my mind as a lake; my thoughts as the winds that blow across its surface; my emotions as the waves that get stirred up. Sometimes all is tranquil; sometimes light waves start lapping at the shore; sometimes rough and stormy ones come crashing down on it. I can observe these conditions without getting caught up in them. Or imagining myself as a mountain, rooted deep in the ground and shooting into the sky, yet for all that might, humbly and tolerantly observing all that comes and goes.

It provided practical techniques, like finding my breath while meditating — in, out, in, out — as an anchor to the present moment. It also helped me start to find my breath when I’m not meditating, and to glimpse how it’s probably possible to transcend the meditating/not meditating boundary such that I’m always mindful and in the present moment.

It helped me discover that my mind’s eye has peripheral vision too, and that if I expand my awareness to include this periphery, it has an immediately calming effect: instead of being trapped inside my own thoughts, I lovingly encompass them (positive and negative) and hold them in acceptance.

These upgrades have generally led me to see how if I improve my awareness, and see things as they actually are, here and now, in this moment, just about everything else naturally falls out from that. I’m finding that living in this awareness and acceptance is more efficient, and that things can at times even become effortless, because I’m no longer straining against my own judgments, or insecurities, or whatever.

It’s not as if it’s easy, though, or that I can always sustain this, or that I even know how far I am in whatever this journey is. And I often find myself back at the beginning, and have to just set out anew, one breath at a time.

I could go on, but I hesitate, and have already shared more than I prefer, if only because I wish to preserve the positive intuitions that this book has instilled in me, and to protect them from any judgment that somebody else might bring to bear on them. But my desire to keep my own experience with this book private is overridden by my hope that sharing it might help somebody else start to form theirs.

So I’ll just leave it at this: this is one of those rare books that’s so good, I started rereading from the beginning as soon as I’d reached the end. I imagine I will do so again and again, and I’m certain I’ll get something new out of it every time I do.

It’s timeless and true.

02 May 2023

Designing Your Startup’s Interview Process

We built our founding team at Accompany by recruiting from within our personal networks. Hiring close friends and colleagues ensured everyone we added to the team was phenomenal, and it let us rely upon our past experience working together in place of a formal interview process. As we started to scale our team, though, we had to expand beyond our personal networks and source candidates we didn’t already know. This meant we had to design an interview process that worked just as effectively.

To do so, we approached interviewing very deliberately. We treated our interview process like it was another product we were building — one to be designed and iterated on. This consumed a lot of our team’s creative energy, but it paid to get this right. In the end, we designed an interview process that candidates enjoyed and that consistently led to hiring great engineers. ¹

In this post, I’ll present how we designed each step of our interview process and why. Every startup is unique, and their interview process should be too. Still, my hope is that a lot of what we found can serve as a useful starting point for founders designing their own interview process from scratch.

Introductory Chat

We began with a thirty minute introductory chat with the candidate. This was a chance for both sides to determine if we wanted to commit to interviewing.

We asked ourselves: “If this candidate were to pass all of our technical interviews, would we want them on the team?” If we wouldn’t, there was no point in proceeding, no matter how good at programming they might be. To determine this, we asked the candidate about their favorite past projects and what they were seeking in their new role. This quickly identified candidates who would be a great fit – friendly and optimistic hackers at heart, who prized a high degree of autonomy and responsibility, who wanted to make stuff that people actually use, and get equity for it. The kinds of people who would make great startup founders themselves. It also quickly identified mismatches, like candidates who either just weren’t very nice, prioritized more work-life balance than we could offer, or (whether they realized it or not) wanted to join a company much larger than ours. ²

We tried to help the candidate answer the same question for themself by telling them about our team, product, and ambitions. This introductory chat was always a blend of assessing if the candidate would be a good fit for us and pitching how our startup could be a good fit for them. Contextualizing the role to the specific candidate — by exploring where their prior experience could prove useful, discussing how our upcoming projects could meet their interests and goals, and imagining the impact they could have for our customers — enabled us to naturally do both at once.

We also used this call to check basic things like start date, employment status, location, and compensation ranges. We didn’t want to go through the entire interview process to only then discover the candidate was seeking a salary twice what we could offer.

We told candidates at the end of the call if we’d like to move forward. With practice, we were able to accurately determine this on the spot. Doing so pleasantly surprised candidates and helped build momentum. If we weren’t going to move forward, we found it was smoother to just let the candidate know the next day over email.

I’ve noticed founders can be tempted to either skip this introductory chat entirely or outsource it to a recruiter. This is a mistake. Nobody can tell if a candidate would make for a great addition to the team better than the founders. And the candidates you ultimately hire are only as good as the ones you decided to interview, so there’s a huge return on spending the time up front to get this right. ³

The other benefit is that candidates are more likely to decide to interview if they get to learn about the company directly from one of the founders. And in the early days, when your startup is still unknown, you have to do whatever you can to stand out. If done right, this introductory chat is a chance to convey to the candidate that you are keenly interested in them, their goals, and the contributions they could make at your company. You’re building a relationship with the candidate over the entire course of their interviewing with you; the sooner you start, the stronger it will be by the time they’re deciding if they want to join.

Technical Phone Screens

After the introductory chat, we conducted two thirty minute technical phone screens. ⁴ The goal of these calls was to determine if we should invite the candidate onsite for a full day of interviews.

We found that a single thirty minute call wasn’t long enough to accurately assess the candidate’s abilities and yielded too many false positives. But a single sixty minute call often resulted in us getting stuck spending an hour with a candidate that we could tell wasn’t a good fit a few minutes in. So two thirty minute calls ended up working best, and had the added bonus that two different interviewers could vet the candidate before we brought them onsite.

On each call, we’d spend five minutes getting to know each other, twenty minutes working on a programming problem, and then five minutes debriefing with the candidate on their solution. We had the candidate code up their solution in a collaborative editor in the browser or just by screen sharing their desktop. We had them actually run their code, and we provided test cases for them to work against. This helped remove some of the superficial dynamics that can creep into interviewing and let the candidate work more naturally.

We were surprised to find that easy questions told us more about the candidate’s abilities than hard ones. In only twenty minutes, good candidates could nail an easy question, and we’d get to see how they designed, implemented, and debugged their solution. When we tried hard questions, candidates had to spend too much time just figuring out how to even solve it, and we wouldn’t cover enough ground to determine if we should invite them onsite.

Inviting the Candidate Onsite

If the phone screens went well, we’d invite the candidate to come in for a full day of interviewing at our office. Initially, we fell victim to the mistaken belief that we should share very little information about what to expect. We thought it was important to preserve secrecy; why give away what’s going to be on the test? This was a huge mistake. It made candidates nervous — like they were entering into some mystical rite of passage — and left them unprepared.

Over time, we learned to invert this and became extremely transparent, arming candidates with as much information as we could to set them up for success.⁵

Here’s what we shared when we invited them to come onsite:

• Who the candidate’s interviewers would be, what their background was, and what they were working on at our startup. This helped remove some of the anxiety that comes with being interviewed by a total stranger, and let the candidate prepare questions of their own well suited to each individual interviewer.
• What topics each interview would cover and how it would be structured.
• Tips on how to prepare, like ensuring their development environment was set up on their laptop; familiarizing with writing a small program from scratch; reviewing things like printing to stdout and using standard library calls that they would need in the interview but might not use in their daily work inside a large codebase.
• What qualities we were looking for: problem solving ability, solution design, implementation ability, and communication skills.

Telling candidates what qualities we were looking for was especially helpful. Don’t expect them to magically know what you value. Tell them in advance, and if you notice them falling short on it during the interview, coach them to see how they adapt. Once we started doing this, candidates had a better sense of what to prioritize and performed better.

The Onsite Interview

We began our onsite interviews with lunch because none of us could reliably manage to get in much earlier than that. At first we felt a bit guilty about this, but it ended up being ideal, because it gave the candidate a chance to meet the entire team and work out any nerves before diving into interviewing.

We conducted three interviews: ⁶

• Writing a simple program, on the candidate’s laptop in their language of choice, assessing programming proficiency and code quality (90 minutes)
• Designing a small software system, on a whiteboard, assessing practical concerns like coming up with a clear interface, a correct implementation, and good performance (60 minutes)
• Solving a few algorithms questions, on a whiteboard, assessing problem solving ability and solution design (60 minutes)

Every startup is unique and their interviews should be too. Our product required strong software architecture and algorithms abilities, so we designed our interviews to assess that. Other startups should design theirs accordingly. A less algorithms heavy startup might benefit from replacing the algorithms interview with a debugging exercise or a second coding session.

Interviewing will always be an approximation of what it’s actually like to work in the role. Our aim was to make it as close of an approximation as possible. We needed to figure out how good the candidate would be at the work they would actually do if they joined the team, and not just how good they were at interviewing.

We found a few ways to shrink the distance:

• We gave candidates problems that we’d actually had to solve. Our system design interview asked candidates to design an API endpoint that we’d actually had to build, our programming problem emphasized coding skills that we used every day, and our algorithms interview tested concepts that we needed to know in order to maintain correctness and performance in our product.

• We encouraged candidates to work the way they normally do. In our coding interview, for example, we invited them to Google and Stack Overflow anything they weren’t sure about, and we reassured them not to feel embarrassed if it seemed like a dumb thing to look up. We all do this every day in our regular work; why shouldn’t candidates do it in their interview? We also suggested they run their code early and often, because we noticed candidates who did so produced better results.

• We tried to make the candidate feel like they were collaborating with a future coworker rather than being judged by an interviewer. In our coding segment, for example, we encouraged the candidate to treat their interviewer like a peer they were pair programming with. Ultimately, the candidate was responsible for designing the solution and writing the actual code, but we invited them to talk through anything they were grappling with. This let both parties get a feel for what it’s like to really work together. If we made a suggestion, did the candidate run with it or ignore it? If they got stuck on something, did they just need a nudge, or did we have to perfectly spell things out? If we pointed out a bug, did they get defensive or eagerly jump on a fix?

We actively interviewed. We weren’t on Slack, clearing out messages while we waited till the time was up to see if the candidate had coded up the right answer. Instead, we engaged fully with the candidate, observing how they think and approach their work.⁷ We realized this mattered more than if they came up with a completely correct answer. There were rarely circumstances on the actual job (production outages aside) where we had to perfectly solve something in under an hour. But we always needed to work productively. Actively interviewing let us assess if the candidate did.

It was helpful to ask the candidate to reflect on their work at the end. What were they happy with? What did they wish was better? If they had another hour, what would they do next? We treated this like an informal code review, and would share what we liked and wished were better too. This told us a ton about what the candidate valued and how receptive they were to feedback. We gained a lot of confidence in making offers to candidates who didn’t come up with a perfect solution if we were able to discern that they saw its shortcomings and had good ideas about how to address them.

Sometimes candidates really struggled at certain points in our interviews. If it became clear they were completely stuck, we’d make a mental note and shift from testing to teaching. This was just the nice thing to do, and it also enabled us to move onto the next question, which a candidate might do better at. It’s important to help candidates preserve their self-confidence along the way. Nobody does great work when they’re feeling demoralized.

The Hiring Decision

It took practice to become proficient at deciding if we should make an offer.

After a long stretch of rejecting nearly every candidate we interviewed, we had to take a step back and remind ourselves that the goal of interviewing was to hire great people onto the team. Since we weren’t doing that, we needed to improve our interview process until we were. This may seem obvious, but it was surprisingly easy for us to lapse into assuming that the reason we weren’t making any offers was that the candidates just weren’t good enough, when in fact it was actually our interview process that wasn’t good enough. Over time, we improved how we sourced candidates, changed the questions we asked and how we asked them, and refined our criteria for determining if a candidate had passed our interviews.

Making good decisions required rigor. The mechanics mattered. We made each interviewer write up their feedback right away while their memory was still fresh. Everyone followed the same template, noting the candidate’s strengths, weaknesses, and if we should hire them. Each interviewer’s decision came in the form of: Strong No, No, Yes, Strong Yes. ⁸ The same evening as the onsite, all the interviewers would get together (including whomever conducted the introductory chat and phone screens) and share their feedback with each other. We’d discuss, debate, and decide.

We didn’t have a fixed rule treating Strong No’s as vetoes; we just discussed why the interviewer gave that vote. But usually, if a single interviewer had strong objections, that would be it. Or if all the Yes votes were only lukewarm, we still might not hire. Having all interviewers in a room made this a more consensus driven process rather than just tabulating the votes and applying some formula.

Ultimately, our decision came down to if we believed the candidate would be effective in the role we were hiring for and if the company would be stronger for having them on the team. However they had performed in the interviews only mattered insofar as it answered this question. For example, we’d hire candidates that didn’t quite perform at the level we were hoping for if we could tell that they were determined and were fast learners.

Making an Offer (Or Not)

Speed was one of our competitive advantages, so we let the candidate know the next day if we would be making an offer.

We didn’t always give the actual offer right away though. Instead, we asked candidates when they’d be ready to decide by (which was typically whenever they finished interviewing with other companies) and then gave them our offer a week prior to that. This let us avoid giving an offer without a deadline — we didn’t want candidates to shop it around, or to have to rescind it if we ended up filling the role with someone else — without having to give an “exploding” offer that forced the candidate to decide before they were ready. Once a candidate had all the pieces on the board, a week tended to be plenty of time for them to decide.

When we gave candidates the good news, we also shared a quote from each interviewer capturing something that had really impressed them during their time with the candidate. This showed candidates that we were genuinely excited to have them on the team and what the camaraderie would be like if they joined.

If a candidate didn’t pass our interviews, we let them know via email and offered to do a phone call to debrief. Most companies don’t do this, and it meant a lot to candidates that we did. It just seemed like the right thing to do — the candidate spent all day interviewing with us; the least we could do was spend half an hour on the phone giving them feedback. But we discovered it was a great way for us to get feedback too. When candidates agreed with our remarks, we knew our interview process was working well, and when they disagreed, it often identified things that we could improve. Following through like this left such a positive impression with candidates who didn’t pass our interviews that they would often later refer friends who did.

Closing the Candidate

Once we made an offer, we kept in close touch with the candidate over the week that they had to decide. Different members of our team emailed the candidate to share why they were excited to work with them and to offer to chat. The hiring manager (namely, me) would schedule a call to check in and see how the candidate was leaning. We found that encouraging open communication let the candidate share any concerns, and if needed, let us adjust our offer to ensure we were competitive. It also provided an opportunity to share our own perspective on how to think about the decision, which new grads found especially helpful.

Some candidates wanted to dive deeper into the company because it’s always too rushed to fully do so during the interviews. We’d invite them to swing by our office or hop on a call so that we could further demo our app, share more about our roadmap, tell them about our customers, and even have them meet some more people from our team, advisory board, or customer base.

We were careful to never pressure candidates to join and to always respect what was best for them. This was less stressful for everyone, and things ultimately wouldn’t work out well if we forced it anyways.

Only the Start

Interviewing was a tremendous amount of work, but it was only the start. To make all that work pay off, we then had to successfully onboard the new hire and retain them over the long run. Thus began the great craft of management. Since interviewing and managing are such a full time investment, it pays to put it off for as long as possible, at least until you reach product market fit. Once you do, you’ll have the fundamentals of your startup in place, and recruiting and retaining will become easier anyways.

But when the time is right for your startup, it’s worth intentionally designing your interview process like this. The greatest joy of working at our startup was our team, and none of what we accomplished would have been possible without it. So go forth and build the best one you possibly can.

18 Jan 2023

Apple Announces M2 Pro and M2 Max

Yesterday, Apple announced the M2 Pro and M2 Max, and updates putting these new chips into the Mac mini and MacBook Pro. The bits of this that I find most interesting:

• An announcement video presented like a segment of a keynote. I can’t recall an instance where Apple’s done this before, but I like it. It makes for less than a standalone event, but more than just a press release, which feels about right for an announcement of this scope. I hope they do more releases like this throughout the year. It seems like it would free up Apple to announce new updates as soon as they’re ready, without having to hold them for a marquee event like WWDC. And it would also free up space in those marquee events, which are increasingly crammed to the gills.

• The Mac mini still only comes in silver. This will come as a disappointment to the many people who speculated that Apple would offer a higher-end Mac mini in space grey. Their rationale was that in the last of the Intel Mac mini line, the regular Mac mini came in silver but the souped up Mac mini came in space grey. And that the darker space grey says “pro”. But I called it when Apple released the M1 Mac mini two years ago: Apple seems to be moving all the desktop Macs entirely to silver. While this wasn’t entirely obvious when Apple first released the M1 Mac mini in silver, it seemed pretty clear once they later released the (more pro) Mac Studio in silver as well. If a forthcoming high-end Mac mini were going to come in space grey, wouldn’t the even more high-end Mac Studio have come in space grey too? I’m personally fine with this. The allure of space grey wore off for me a while back. At some point it stopped seeming intensely cool and just kind of… drab. And I like having my Studio Display, Mac mini, and MacBook Pro all in matching silver on my desk.

• Apple’s leading with comparing the performance of the M2 Pro/Max MacBook Pros against the old Intel-based Macbook Pros. This seems silly. Why don’t we also compare against a processor from 10 years ago while we’re at it? Benchmarking against the Intel-based Macs of course yields more impressive numbers than comparing against the regular M2 (or even against the M1) does. But that’s a credit to Apple, not a mark against them. And we’re well enough past the Intel transition (Mac Pro aside…) that comparing to an Intel processor feels kind of irrelevant. That said, maybe Apple is targeting a subset of the customer base that has yet to switch to Apple silicon, and this messaging is specifically aimed at convincing them to do so. Our new MacBook Pros are 6x faster than your old Intel one… Now will you switch?

• It feels a little asymmetric and funny that the Mac mini (you know, the desktop) doesn’t get the most powerful chip, and the MacBook Pro (you know, the laptop) does. But Apple positions the Mac mini as their affordable desktop, and there is the Mac Studio, so I suppose it makes sense.

• As for me, I still have so much performance headroom in my M1 Mac mini and M1 Pro MacBook Pro that I won’t be upgrading, but it’s nonetheless heartening to see a more regular cadence of updates coming to these machines now that Apple controls the silicon. He who controls the spice controls the universe…

07 Jan 2023

Start in a Niche

Speaking of Le Guin, I just came across her recounting of how she got her earliest work published, and her start as an author:

I had entered the field of science fiction two or three years before via publication in genre magazines. Academia and literary criticism snubbed it, but it had a lively, informed, and contentious critical literature of its own in magazines and fan-zines, and it was notable for the close connections among its writers and readers. Young writers in the genre were likely to get more intelligent attention and more sense of their audience than those who, having published a conventional realistic novel, were often left in a great silence wondering whether anybody but the proofreader had read it.

— Hainish Novels & Stories, Volume One, Introduction, page xiii

It’s strikingly similar to the way successful startups often get their start: in some nascent niche — that’s ignored by incumbents, and small but growing — building what to outsiders looks like a toy, and where there’s a clear and concrete need from early users, whom the startup forms a deep understanding of. Le Guin found writer reader fit the same way good startups find product market fit.

It’s neat that this is shared across different fields. Most pursuits benefit from early and frequent feedback. Great stuff isn’t made in a vacuum. So just make stuff you love to make, share it with others, and use their feedback to iterate and improve. If you’re ever tempted to stop short from fear of failure, turn to the last bit of the quote. Better to share something with others and learn they don’t like it than to pour all your effort into something and wonder if anybody saw or cared. You can always try again.

06 Jan 2023

📚 Rocannon’s World & Planet of Exile

I enjoyed reading Rocannon’s World, Ursula K. Le Guin’s first published novel.¹ It was neat to discover that many of her signature ingredients were in place right from the start:

• Minimal and elegant prose
• A keen interest in human (and nonhuman) nature
• Reverence for nature, imaginatively rendered on an alien yet familiar world
• Magic and supernatural elements rooted in language, community, nature… The every day things that are all around us, but that we so often fail to really see
• A character’s journey into the unknown, seeking something external, only to in the end discover internal truths instead

Le Guin realizes most of these ingredients more fully in her later work (The Left Hand of Darkness and A Wizard of Earthsea particularly come to mind), but they’re all here.

If you’re curious to read Ursula K. Le Guin, I’d recommend starting with one of her more famous books (like Earthsea or Left Hand). They’re better. But if you were curious about this book for whatever reason, or if you’ve already read those ones, I’d happily recommend this. It’s good, and I was both satisfied and a little sad it was over when I finished.

I did not enjoy Planet of Exile, her second published novel which is set in the same Hainish universe, as much. This surprised me. I figured that as an early author finding her form, her second pass would be better than her first. Maybe she had more time realizing Rocannnon’s World? Or maybe it’s just a matter of taste; the two books have similar ratings on Goodreads…

In her courses on writing, Le Guin emphasizes the importance that a story moves. From her excellent writing guide, Steering the Craft:

What it has to do is move — end up in a difference place from where it started. That’s what narrative does. It goes. It moves. Story is change.

Well, Rocannon’s World moves. Quite literally: Rocannon moves clear across the planet of Fomalhaut II as he journeys on his quest, and the narrative and reader move with him. I enjoyed some deep flow while reading it, immersed in the story’s movement, propelled by Le Guin’s minimal and pure style.

I didn’t find the same kind of movement and accompanying flow in Planet of Exile. The plot kind of meanders, and we end up somewhat in the same place as we started. The characters and communities they live in do change, so Le Guin is still following her own advice. She just isn’t doing it with the singular aesthetic that the focus and drive of Rocannon’s World and her later works offer.

I appreciate Planet of Exile nonetheless, as a brief stop on the way to greater things. And I enjoyed some of the ideas, like how both peoples (one native, one alien) think of themselves as human and the others as other. I liked the further exploration of mindspeak, which we first encounter in Rocannon’s World. And I enjoyed the alternating viewpoints that Le Guin experiments with here; the counterbalance of Rolery and Jakob as wife and husband feels like a prototype for the gender exploration that Le Guin masterfully realizes in The Left Hand of Darkness. In all, though, I might skip reading Planet of Exile unless you are an avid Le Guin fan or interested to see what the early work that comes before a masterpiece can look like.

03 Jan 2023

Writing More

I’m hoping to write more this year and have been considering how I’ll go about it. I strive to write things that are both true and new, but it’s hard to always say something new. I don’t want to let that limit how much I write, because the way to get better at writing is to write a lot.

So here’s my plan: true and new is my goal, but just true is sufficient. So long as what I’ve written is correct — or at least as correct as I can get, given my current understanding — I can post it.

Writing something that’s true but not new is still useful to me. It cements my understanding of the topic, yields a handy reference for my future self, and is good practice. I write first and foremost for myself, so as long as it’s something I want to write and read, I’m happy doing so.

But I do want my writing to be useful to others too. Even if the ideas in something I write aren’t new to me, they could be new to some readers. And saying something novel is a matter of degree. The core idea may not be new, but perhaps putting it into my own words and sharing my perspective adds something that is.

I wonder if writing things that are true, but not new, will push me into the territory of ideas that are both. Maybe I need to first travel through the land of familiar ideas, honing my powers of observation and expression along the way, in order to reach the land of unfamiliar ones.

I won’t overthink it. Writing is better than not writing, and that can be my compass. I’ll write about interesting things, and seek out interesting things to write about.

I’ll experiment – with both what to say and how to say it – until I find my voice and the constellation of topics that feel like an authentic fit. I’m hoping to play around with different formats like shorter posts, link posts with commentary, and posts where I’m still in the midst of figuring something out.

If all goes well, my writing this year will be a journey of discovery, which I hope to get to share with at least a few readers, and which I hope will yield interesting new things.

Happy writing, happy reading, and happy 2023.

18 Nov 2022

What I've Learned About Angel Investing

I recently started angel investing and have now invested in seven startups. I’m treating it as an experiment, and I don’t have any results yet. Even so, I’ve learned a ton from making these first investments, and want to refine what I’ve found before making more.

At YC’s Investor School, Ron Conway prefaced his advice to aspiring angels with: “Teach yourself”. I now understand why. All the advice at Investor School was super helpful, but there’s no teacher quite like experience.

So, here’s what I’ve taught myself about angel investing… So far.

It’s Fun

The most important thing I’ve learned about angel investing is that I find it to be super fun.

Before I got started, I wasn’t sure if I would. I’d loved doing my own startups, but would I enjoy investing in somebody else’s? There was really only one way to find out, so I just made a few investments. Happily, I had a blast doing those first ones, so I kept going with it.

It’s exhilarating to meet energetic and optimistic founders who have the kernel of an idea and the conviction to try it. And it’s gratifying to be able to help them in some small way. There’s this special feeling in the air when these ingredients come together. It’s just pure potential.

If I didn’t find angel investing to be fun, I would have stopped. It’s hard to get really good at something I don’t like doing. And with angel investing in particular, if I was only doing it to make money, I think I’d make worse decisions. It’d push me towards worrying about the wrong things, like valuations and what other investors think. Since I’m just having fun, I gravitate to the right things, like the founders, their product, and their customers. Just like the way to start a great startup is counterintuitively not trying to start a startup, I wonder if the way to make great angel investments is to not worry too much about making money…

At the very least, if my main motivation was making money, I’d be disappointed if all my investments went to zero. Whereas I’m currently having so much fun with each that it’ll just be bonus points if I see a return on any of them. But I really think I will. The founders I’ve invested in are all really good!

Founder Over Idea

The founders matter the most, so I’ve made each of my investments because of them more than their idea. ¹ But they’re still pitching me on their idea, so I had to figure out how to evaluate it. After a few pitch calls, I found a trick: just assess the idea for what it tells me about the founders.

Why are they working on their idea? It needs to be to solve a problem they have deep conviction in. One founder that I invested in saw his Dad’s long standing restaurant suddenly go out of business during the last recession. That got him thinking about software to help restaurant owners improve their bottom line. That’s conviction. Whereas another founder I met with was trying to build a better version of X, but didn’t have a compelling case for why the current X isn’t good enough. Something, something, “ours is going to be better”. I didn’t invest. It felt like a solution in search of a problem.

Are they obsessed with their idea? The founders I’ve invested in think about their idea all the time. They know their problem domain inside out. They’ve tried all the existing solutions, and not just out of due diligence; they really want something that solves their problem! But they’ve come up empty, so they’re building their own. This also means they are their own first users (or close proxies), and that they know where to get more.

And are they also flexible with their idea? Will they experiment their way from the initial idea – which rarely works – to something that does? I try to discern this by tossing out a bunch of related ideas to see how the founders respond. The ones I’ve liked are open to considering any of them and quickly cook up ways to test the promising ones out. Whereas founders I’ve decided not to invest in let the ideas just kind of pass them by. Being flexible doesn’t mean being easily swayed though. The best founders always seem certain of what to try next.

I do still weigh the idea itself. Can I imagine it growing into a billion dollar company? If I can’t imagine some way, I’ll pass. And I also need to be just plain excited about the idea. It’s hard to do a good job helping the founders I invest in if I don’t care about what they’re working on.

How do I assess the founders themselves? One trick I’ve found is to ask myself if I’d want to work on a side project with them. This reduces the question of deciding who I should invest in to the much more familiar one of deciding who I should work with. I’ve had a lot of practice answering that over the years, so it lets my subconscious serve up the answer. Thinking in terms of a side project calls for the right attributes in the founder and ensures I’m exacting enough without being too exacting. “Would I cofound a startup with them?” would be too exacting. There’s just no way to know that after a thirty minute call. Whereas that’s plenty of time to determine if it’d be fun to work on a side project together.

One nice property from all this is that investing in the best startups means investing in the best founders. And investing in the best founders requires meeting the best people, which is something I already want to be doing anyways.

How To Be Decisive

For each of my investments, I’ve taken one meeting and then decided within a few days. ²

At first I did this for the founders’ benefit, but I’ve found it’s my preference too. Agonizing over a deal is stressful and unproductive. To avoid getting stuck in limbo, I aggressively address my remaining concerns after the pitch call. I accept that there will be some I can’t resolve. And then I just make my best guess. It’s helped me to write out the concerns I have, and why I’m investing despite them. If I’ve decided not to invest, I write all the reasons I might regret the decision. Formalizing this brings me closure. It lays plain how I’m making difficult decisions on imperfect information, and that there isn’t a right answer.

I’ve discovered there’s also a nice reward for deciding quickly: everyone feels great! It conveys to the founders that I believe in them and am eager to get to work. And it’s a helpful test for me. If I can’t decide quickly, I probably don’t feel this way, and so I probably shouldn’t invest.

It’s helped me to decide on all the knowns prior to the pitch call, like how much I’d invest and what my key concerns are.This frees me to focus on the unknowns that come up during the call. I try to learn as many new things during the call as I can instead of just validating what I already think. This generates more data points for me to work with when I later decide.

It’s helped to stay focused on the founders. I can’t overthink that after the pitch call in the same way I can overthink an idea. And I’ve already established that the founders are more important than the idea anyways.

And it’s also helped to lower the stakes by writing smaller checks. I thought this might make founders less inclined to talk to me, but it hasn’t. Especially after I show that I’m easy to work with and will provide concrete help in addition to money.

How To Help

I like helping before even starting to talk about investing. It provides an organic way to explore things and ensures I’ve earned the founders’ time.

I can start by getting them some users. I can always get at least one… Me! Trying out the product is fun, and also helps me decide if I should invest. Is it any good? Does it improve each week? How attentive are the founders to me, their humble user? ³ In the process, I come up with useful feedback that I can share with them. Win win.

Sometimes I can introduce the founders to other potential customers. If they convert, I’m way more inclined to invest.

After I’ve invested, I try to bring a few more good angels into the round. It’s a lot of leg work — checking if the angel is interested, ensuring the founders are interested, and crafting the intro — but it’s worth it. It’s rewarding to connect good founders with good angels. And I like getting to work with my angel friends in this ad hoc way. Win win win.

I enjoy providing ongoing advice and mentorship most of all. I’ve found this works best if I meet with the founders on a regular basis. ⁴ Since every startup is unique, it helps to have the company’s context and history in order to give good advice. So far, the topics that come up the most are getting users and figuring out hiring.

I’ve learned not to speculate. Bad advice is worse than no advice. If I don’t have direct personal experience with something, I just say that. At first I felt bad about this, but I’ve noticed the founders don’t mind. They just go ask some of their other angels. But I do make a note to go learn whatever it is firsthand, so that the next time it comes up I have useful experience to draw upon.

Sometimes the most valuable help is offering moral support. Real moral support is giving the founders energy and promising directions to channel it. It’s helping them identify their most pressing problem and possible ways to solve it. It’s giving them feedback on their work, especially until they have users to do that for them.

I benefited immensely from this kind of support when I was doing my own startup. Things could get really demoralizing when I wasn’t sure if it was going to work, and it was helpful to share my burden with mentors who really understood my company but sat outside its emotional gravity well.

I’m extremely grateful to the few angels who took a keen interest in providing that to me, and am glad to be finally paying this back to other founders now.

Leaps Of Faith

My first investments were in close friends that I have a long history of working with. Those were no brainers. I’d invest in them again and again. But when I wanted to make more investments, I had to branch out and invest in people I’d just met. The first time I did that felt extremely weird, but I got used to it surprisingly quickly. Formalizing the qualities I look for in founders helped, as did officially committing to experimenting with angel investing. At that point, investing in new connections just came with the territory.

There’s also this question of making money… It’s required a leap of faith to invest in startups raising on such high caps. They’ll have to become unicorns in order for me to see a meaningful return on the investment. And it’s required an even bigger leap of faith to keep making investments before I have any results back. That will likely be years from now, when the startups I’ve invested in have successful exits or die. And while I will get some partial results along the way, like if they gain traction and raise subsequent rounds, I don’t even have that data yet. But this seems like the kind of thing that doesn’t work until it does, and like the way to succeed is to just keep going. ⁵

I’ve been surprised by how random it all feels. Super angels and top VC firms get to see every deal, but I don’t. So it’s all a bit haphazard as I invest in people I happen to meet and decide I like. I’m hopeful that over time, as I work with more founders and other angels, I’ll get a feedback loop going and things will feel more comprehensive.

But it’s always going to be at least somewhat random because it’s impossible to predict the future of technology. There’s no way to know if a startup will work. And the founders I invest in may end up working on completely different things anyways.

In most of my other work, I’m accustomed to arriving at a correct answer through rigorous effort. Angel investing just isn’t like that. I’ve learned to just accept this, make the best investments I can, and trust that it will all work out.

Always Be Closing Coding

The last thing I’ve learned about angel investing is that, as fun as it is, I don’t want to spend all my time doing it. If I did, I wouldn’t have time to make things, like this essay or cool computer programs. That’d be sad. There’s a satisfaction in making good things.

It’s not just for the art though. I think writing and hacking will improve my investing. It will lead me to interesting technology and the people working on it. And it will keep me empathetic to them through frequent reminders of how hard it is to bring something new into the world.

Making things maintains balance. If I was angel investing full time, I’d find myself always seeking “opportunities”, essentially looking at the world through the lens of a salesperson. That sounds terrible. All the magic would go out.

I’d rather be first and foremost a maker, curious and always learning. And whenever that brings me abreast of founders I can help, through angel investing or otherwise, I will.

So as I ramp up my angel investing, I’ll keep working on projects in parallel, and let one reinforce the other. Who knows where it will take me.

09 Oct 2022

Small Projects

I tend to assume that a new project, like writing something to post here, will take a lot of time. But today I realized a neat productivity hack: What if I tell myself it will only take a little?

Maybe I’ll trick myself into actually finishing it faster! But even if I don’t, I’ll at least have tricked myself into getting started. Often times that’s the hardest part, and it seems less daunting to start something that’s only supposed to take a few minutes than something that’s supposed to take a few hours, days, or more. ¹

I don’t think this is just because of time commitments. A project that is supposed to take a long time feels serious, which causes me to have higher expectations. Things suddenly seem intimidating. I cautiously take a step back to try and see the entire thing, which isn’t even possible yet.

Whereas a project that’s only going to take a few minutes or hours… no big deal. “Oh, this? It’s just a little blog post about a quick idea I had…”.

This effect seems similar to how iconic products can start out as “toys”, massive companies can grow out of side projects, and entire essays can come from a few passing conversations.

So maybe the real hack isn’t to tell myself a project will be quick, but to actually shrink the size of the project. If I do this each step of the way, I’ll eventually grow it into something bigger, and in a natural way where I never got stuck.

25 Jul 2022

The Apple Studio Display

I finally received my Studio Display after much supply chain related delays. I went with the tilt and height adjustable stand with the standard glass option.

The Studio Display’s aesthetic design is exquisite. It’s a beautiful object atop my desk. It exudes a sense of calm. The display seems like it’s just floating in space. There’s something about the black bezel surrounding the display, and the stand’s minimal footprint which only barely extends in front of the display, that yields this effect. It imparts this ineffable quality that makes me want to work at the display. The minimalist design lets the display all but disappear, automatically pulling me into focus mode.

I like the 27” size. The Pro Display XDR comes in the larger 32” size (and with 6K resolution, instead of the Studio Display’s 5K, in order to maintain Retina), but I don’t find myself wishing for it. 27” feels right to me: large enough to comfortably fit two windows side-by-side, and large enough that there’s some content in my peripheral vision, but small enough that I hardly have to turn my head to view the outer edges of the display. It’s mostly just contained right in front of me. I really like this form factor for physical ergonomics.

I’m happy with my decision to stick with the standard glass. I thought I might want the nano-texture option, which is why I’m only just now receiving the display. By the time I made it to an Apple Store to see the nano-texture in person, the display was backordered by a few months. My personal preference is for matte displays; I can’t stand glare or reflection when I’m working. I really liked the matte upgrade option on my 2011 MacBook Pro, back when Apple still offered that on their notebooks. Surprisingly, I don’t like the nano-texture option on the Studio Display.

While the nano-texture is extremely effective at eliminating any and all glare — truly impressive; I tested it out at the Apple Store in the Stanford Shopping Center, which is basically a glass box with sunlight streaming in from all directions — this black magic comes at a cost. There’s an effect that I can only describe as being somewhat like having a film layered over the screen. It reminded me of the plastic screen protectors libraries installed on their computer screens back in the day. In practice, I found the nano-texture imparted some “texture” to content, almost like a subtle but perceptible pixellation. I especially noticed this with text. This tradeoff wasn’t worth it to me: eliminating glare some of the time by taking on this effect all of the time.

If I was in an environment where I had to deal with sunbeams directly hitting my display for much of the day, I’d have chosen the nano-texture anyways. But my home office where I’ve set this up thankfully doesn’t have that problem; it has a very large, north facing window which lets in lots of ambient light, but no direct sunlight. The window is perpendicular to my display. For ambient light, even in a room with a lot of it, the standard glass eliminates just about all glare. Apple mentions that the standard glass is already engineered for extremely low reflectivity, and empirically this seems to be the case. My main advice would be that if you think you’re interested in the nano-texture, be sure to see it in person first. The other thing to be aware of is potentially finicky maintenance and care issues with the nano-texture etching. I’m pretty careful with my stuff, but even so it’s relieving now that I have my Studio Display set up for daily work not to have to worry about one errant fizzy water or sneeze destroying it. Yikes.

The tilt and height adjustable stand is gorgeous and easy to use. It solidly holds the display in place wherever I set it. It’s very granular; you can set the display to any point along the curve. I actually wish the stand let the display go a little lower. Set at the lowest setting, the top of the display is still just slightly above my eye line. Optimal ergonomics sets the top of the display even with your eye line. It’s close enough for me that this is only a minor concern, but I’m six feet tall so imagine it could be an issue for others. Though I bet most people will feel like they want it higher than the lowest setting anyways. As I’ve gone down the ergo rabbit hole, I’ve learned that everything (chair height, desk height, display height) should be much lower than you’d naturally think.

The stand’s moment of truth for me, after setting everything up just so on my desk, was to type at my keyboard and see: does the display wobble? I am happy to report that it does not wobble. This was a huge problem with the LG UltraFine 5K that I’m switching from. I type fairly lightly, but I use a standing desk, which only has two legs instead of four. The LG display wobbled like crazy. Letters literally jiggled when I typed. It was maddening. The Studio Display is entirely immune from this problem when my desk is at sitting height, and almost entirely immune when at standing height. When standing, there’s a tiny bit of wobble, but it’s so minor that I don’t find it distracting.

The Studio Display has a bunch of other attributes that I like better than the not-so-ultra-fine LG. The macOS integration is way better. The LG had weird problems like sometimes taking forever to wake from sleep and letting the display’s brightness get out of sync with the macOS brightness setting. I’d have to adjust the setting to resync the display’s brightness. With the Studio Display, everything just works.

Everyone has critiqued the built-in camera’s poor image quality. I agree; I find it makes me look like I’m made out of plastic. It’s a shame, because the bad camera prevents the Studio Display from entering the rarefied air of a perfect product. And it’s so agonizing, when the Studio Display’s Achilles heel is something so obvious! It’s literally in the name — the Studio Display. Shouldn’t it have a great camera that makes you look amazing in your home… studio? ¹

The consensus seems to be that the image quality is so bad because Apple went with an Ultra Wide camera, and that they did this in order to offer Center Stage. Everyone disses on this decision, smugly pointing out that Center Stage doesn’t make any sense on a display where you’re sitting directly in front of it. I disagree and have been pleasantly surprised by two very nice benefits from Center Stage:

• If I raise my desk from sitting to standing, I used to have to adjust my monitor height and/or webcam tilt in order to properly frame myself in a video call. This was really annoying and disruptive, because I invest a lot of effort into getting my display adjusted just right for ergonomics. Now I don’t have to muck with it, because Center Stage just smartly pans and crops me so that I’m automatically vertically centered. Win.
• Center Stage’s primary use case — reframing the shot to dynamically support people entering and leaving — is especially nice on a stationary display. With iPads and Macbooks, it’s at least easy to physically move the device to fit everyone in the shot. Moving a desktop display isn’t feasible. And while a lot of Center Stage critics claim having multiple people in a video call taken from your Mac + Studio Display isn’t common, I think it totally would be in an open-office startup environment where ad hoc meetings happen and people come in and out of the call. I also anticipate we’ll end up taking a lot of family video calls on mine here at home for the same reason.

I’m not sure the Ultra Wide + Center Stage was the right tradeoff to make, but at least what we lose in image quality we gain in ease of use.

Confounding camera issues aside, I’m extraordinarily happy with the Studio Display. There was such a long stretch where you were just plain out of luck if you wanted a Retina display, made by Apple, at a palatable price, for your Mac. Thankfully the Studio Display is exactly that.

I’m enjoying my first few days of working on it mightily. Great craftsmanship benefits from great tools. The Studio Display is a great tool.

01 Jul 2022

📚 Summer Reading List

There’s something special about summer reading. It feels different than the reading I do throughout the rest of the year because of habits I formed growing up. When school let out for summer, I’d have three glorious months of being left mostly to myself. For me, that meant visiting the library, checking out the biggest stack of books they’d let me walk away with, and then reading them all week before returning to do it all over again. The good life!

Even though summer doesn’t really bring a sudden abundance of free time like it used to, I still like to let it bring a sudden abundance of reading. I love immersing myself in a period of intense reading, knowing I’ll come out different on the other end.

Here’s what I’m hoping to read this summer and why.

The Hobbit - J.R.R. Tolkien

This feels like the perfect way to kick things off. Rereading this will be full of nostalgia and a great way to limber up my imagination. I last read this in middle school up in a walnut tree that grew in our backyard. I’m hoping to once again read this out in nature and without a care in the world, but this time with much better reading comprehension.

Never Let Me Go - Kazuo Ishiguro

Ishiguro’s The Remains of the Day is one of my favorite novels. I’d like to read some of his more recent work (Klara and the Sun, The Buried Giant), but really want to read Never Let Me Go first. It’s been on my list for too long, and is too highly recommended. I’m anticipating getting a lot out of this.

One Hundred Years of Solitude - Gabriel Garcia Marquez

I’m super curious to read this seminal work that (I think?) established the genre of magical realism. I’ve managed to keep completely clear of the plot or premise.¹

The Prophet - Kahlil Gibran

We had a fabulous excerpt from this read at our wedding ceremony, and so I’m hoping to read this short book to nourish my spirit on some cool, quiet morning this summer.

Rocannon’s World - Ursula K. Le Guin

Le Guin is one of my favorite authors; I aspire to read everything she’s written.² I haven’t read any of her stuff in a while, so she’s definitely on my list for this summer. But which to choose? One of her most highly regarded books that I’ve yet to read is The Dispossessed. But it’s at the end of a series of loosely related novels, so I’m going to instead start at the beginning of that series with Rocannon’s World and then work my way forward to The Disposessed. Bonus: it’s short.

The Raven Tower - Ann Leckie

I’m always reading for productivity these days… but I love escaping into great Fantasy & Science Fiction. Summer reading should be filled with great Fantasy & Science Fiction. I really enjoyed Leckie’s Ancillary Justice for its novel ideas and immaculate writing (a rare combination in this genre). I’m hopeful that The Raven Tower will have both as well.

Startup: A Silicon Valley Adventure - Jerry Kaplan

I’d somehow missed this (seemingly classic?) book on the company Go’s failed attempt to make a pen based computer. I’m actually halfway through and just can’t put it down! So far, it’s especially fascinating to see how much Silicon Valley has changed since the heyday of the personal computer in the late 80’s and early 90’s.

In the Plex - Steven Levy

While we’re on the topic of Silicon Valley… I’ve had this on my shelf since it was published in 2011, right next to The Everything Store (which is excellent). I’ve somehow still not read it, but I’ve heard from a few friends that it’s really good. I’m hoping to get some fun new stories about the early days of Google.

The Soul of a New Machine - Tracy Kidder

I don’t know anything about this book, but it was so strongly recommended by a friend that I’m going to read it no matter what it’s about. Plus, it won the Pulitzer.

Sapiens: A Brief History of Humankind - Yuval Noah Harari

I’m actually in the middle of this and put it down when things got busy. The first part was so fascinating that I want to reread it and take notes to post here. I’m going to read it at the same time as some of the others on this list so that I don’t have to wait to get into some great fiction.

The Code Book - Simon Singh

This could end up being a great companion to a summer coding project idea I have. I’ll definitely read it if I commit to that project, but hopefully will read it regardless as multiple friends have recommended it to me now.

Speed & Scale - John Doerr

I recently read Bill Gate’s How to Avoid A Climate Disaster and found it provided a helpful bird’s eye view on climate change. I’m a few chapters into Speed & Scale and am finding it similarly helpful, especially to see where Gates & Doerr agree and disagree.³

Can I really read all these books this summer?! We’ll see. My only reading rule is: there are no rules! I’m totally fine aborting a book if I dislike it, reading books that aren’t on this list, and skipping books that are… Just like I did with the stack of books I took home from the library each week back when I was just a kid reading his way through the summer.

06 Jun 2022

Thoughts on WWDC 2022

This WWDC keynote was crammed with updates for iOS 16, watchOS 9, the new M2 chip and redesigned MacBook Air, macOS Ventura, and iPadOS 16. Each year, Apple’s empire seems more sprawling than ever… So rather than try to cover everything, here’s some impressions on the bits I personally found most interesting in this year’s keynote.


New Lock Screen + Focus Filters

The redesigned Lock Screen lets you customize the font and color of text (time, date, etc), add widgets (which come in a new compact form factor), and drag your custom photo to position it optimally amongst everything. This work seems to build on the momentum from introducing Widgets to the Home Screen last year, which has been a hit amongst users.

The new Lock Screen also moves notifications to the bottom. This seems ideal. We already swipe to unlock from the bottom of the screen, and the top of the screen has become hard to reach with one hand as iPhones have gotten larger. I especially like the idea of being able to assign different Lock Screens to different Focus modes. I can imagine creating a work Lock Screen, with a more understated wallpaper and work widgets (calendar, Slack, etc); a personal Lock Screen, with a family photo and personal widgets (Home controls, Fitness, etc) and an evening Lock Screen when I want to tune out all the noise but still have my iPhone at hand for e.g. reading as I wind down for bed.

Apple is taking Focus modes a step further by introducing filters inside of apps. When you’re in your Work focus, you might only see work related browser tabs in Safari, and when you’re in your Personal focus, you wouldn’t see your work email in Mail. I love Apple’s continued push to provide tools to be present and intentional with how and when we use our devices and the constant stream of information they put at our finger tips. I hope these filters will be helpful, but I think they will only be as good as their weakest link: third-party app support. Things could break down quickly when you leave the walled garden of Apple’s own apps. Will Chrome, Slack, and other apps that straddle people’s work and personal lives support Focus filters?

FaceTime Handoff

This lets you seamlessly move a FaceTime call across your iPhone, iPad, and Mac. I can’t count the number of times I’ve gotten all set up at my desk, rearranged my windows, double checked my webcam, and prepared for a FaceTime call on my Mac, only to have it come in on my iPhone or iPad instead. Cue the awkward dance of me asking to call the person back, doing so from my Mac, only to have the call get routed to their iPhone, etc… Ideally, a FaceTime call would always come in on the device I’m actively using, but being able to seamlessly hand it off to different devices will be really nice.

Shared Tab Groups

I’ve come to really like Tab Groups in Safari. They help me be more intentional with actively researching something, keep track of everything good that I’ve found, and then destroy the group when I complete the project. (Or just “archiving” it by dragging the Tab Group to the bottom of my Tab Group list for posterity). They also help me stay more organized and focused on the task at hand, instead of having a messy mix of tabs and minimized browser windows for different suspended processes in my brain.

It will be really useful to be able to share them when researching something with others. We’ll each be able to add tabs to the group, and we’ll even be able to see who is viewsing which tab in real time. My wife and I are planning our honeymoon to Italy right now, and I so wish we had this. We currently drop links in our wiki, and then just huddle around each other’s computers to see what the other is looking at.

Continuity Camera

Continuity Camera lets you use your iPhone as a webcam. You have an incredible camera in your pocket, and (sadly) a fairly crappy one built into your Mac. Why not unlock that potential? This is a great feature, and I’m excited Apple is introducing it.

But here’s the thing — there’s this amazing app called Camo that has let you do this for a long time. I have a soft spot for it, because we used it to shoot our Zoom wedding during the pandemic, and it worked great. So it’s a little sad to see Apple sherlocking it.

On the other hand, the Camo creator has a thoughtful and optimistic take on how everything’s going to be Just Fine. And it will be nice to also have Apple offering a solution that just works out of the box, and pushing an ecosystem of accessories for mounting your iPhone to your Mac or (gasp!) Studio Display. ¹

Messages: Edit, Undo Send, and Mark Unread

Apple mentioned that Messages has hundreds of millions of users… It’s often overlooked how huge their messaging platform is. I’m pleased to get support for editing messages (no more follow-up bubbles with “*typo: bats, not cats”), undoing sends², and marking messages as unread. I find myself using Messages with friends and colleagues more and more, so more power for managing it is very welcome.

Family Photo Library

Family Photo Library lets you share photos and videos with up to five other people, so that everyone can share a family photo collection. This seems long overdue. I do wonder how much overhead and cognitive load it will introduce in practice. Will I default to my personal or family photo library? Can a photo live in both? Will it count against storage for both?

Apple seems to have designed helpful suggestions both for creating your Family Photo Library from all of your existing photos, and also for adding new photos as you take them. For example, the Camera app will suggest a photo go in your Family Photo Library if you take it when family members are nearby.

M2 + Macbook Air

The M2 chip looks impressive, but the M1 and then M1 Pro/Ultra are already so impressive, it’s less interesting to me than the redesigned MacBook Air. The new form factor looks amazing, and I especially love the lean, mean Midnight machine.

Despite such a great looking design, the announcement somehow felt… underwhelming. Maybe it’s because this industrial design for the Air takes its cue from the recently redesigned MacBook Pros. It may also be because Steve Jobs set such a high bar when he first announced the MacBook Air by pulling it out of a manila envelope in 2008. And the excitement might have been dulled by sandwiching the segment in the keynote amongst everything else…

Regardless, this machine looks sweet. I went from the M1 MacBook Air to the 16” MacBook Pro. I’m now tempted to switch back, but I’ve come to love the larger display… Which brings me to my one disappointment. I’d really hoped that Apple might introduce a 15” or 16” version of the Air. I don’t actually need the Pro functionality that comes with the MacBook Pro: the faster chip, the extra ports, the fans… I just want the larger display. It would be really nice to see Apple separate the larger display from Pro specs. Perhaps they have no incentive to. It would complicate the lineup, and they know that people who really want the larger display will just pay extra for a MacBook Pro anyways.

Some Curiosities

I’m curious to try the new Freeform app, which provides a collaborative whiteboard to brainstorm ideas with others in real time. This looks like a cool tool for thought. I’ve recently been playing around with the awesome (and already launched!) Muse App… It’s hard to imagine Apple isn’t aware of it, and will be interesting to see how Freeform compares.

I’m curious to try the new Running Form on Apple Watch, which will provide a few metrics: your vertical oscillation, stride length, and ground contact time. This seems like a really tricky task to get right; inferring all of this from a single sensor on your wrist is bound to be error prone, and the science on what constitutes a “good” running stride seems somewhat mixed in the first place.

It’s curious to see that Apple has not only completely redesigned the Home app, but has also reset their marketing. In today’s keynote, they positioned their Home strategy as being early days, they reminded users why they might want a smart home in the first place, and they oh-so-nobly took the stance of being happy to help the ecosystem evolve. I think this is a tacit acknowledgement that their home strategy has been a total mess to date and in need of a reset. Hopefully this complete redesign of the Home app is laying the groundwork for new hardware that works well with it too.

It’s very odd to me that Apple is keeping the 13” MacBook Pro in the lineup, and with the TouchBar no less! This is in addition to the 14” MacBook Pro. I don’t know why they would choose to do this… Is there some market segment that particularly likes this machine?

Notably missing: tvOS. Nary a mention.

Some Speculation

I recently explored some ideas around Apple’s rumored AR/VR headset, and how one killer use case might be watching movies in VR. I didn’t expect Apple to announce the headset today, but I did think they’d announce ARKit (and possibly some kind of new VRKit) features to help pave the way. Perhaps there will be updates to them shared in the developer sessions, and Apple will just quietly lay the groundwork before a large reveal whenever the headset is ready.

Is the new CarPlay a strategic retreat for Project Titan, from launching an entirely new autonomous car to “just” sticking a slick UI inside existing cars? Or is it the cusp of much more to come?

I was guessing that Apple would announce the new Mac Pro today. In the previous “Peek Performance” event when the new Mac Studio was unveiled, John Ternus teased how the Mac Pro is the one remaining machine to complete the Mac’s transition to Apple Silicon… but that it would have to wait for another day. Today seemed like it could be that day. The Mac Pro is first and foremost for developers and creative professionals, so WWDC is the perfect fit for releasing it. Maybe it’s not ready, maybe Apple doesn’t want to launch it amidst supply chain woes, or maybe there just wan’t enough time in this already crammed keynote to do its new architecture and industrial design justice.

05 Mar 2022

Arcane, Apple, and Watching Movies in VR

I was blown away by Arcane: League of Legends, an animated series set in the universe of Riot Games’ hugely popular video game. I haven’t played LoL, but I’ve always been intrigued by video games as a medium for story telling. I’ve even played some games just for their stories. In the end, though, video games’ stories tend to fall short of realizing their full potential. At some point, the story must take a backseat to the actual game.

Arcane realizes this full potential. It’s like if you took a video game, removed all of the gameplay, enhanced the aesthetics, and crafted a thoughtful story with fully formed characters. I’ve never seen anything quite like it. There’s something new going on here, and I think the root of it lies in how immersive it is.

You don’t feel like you’re watching Arcane; you feel like you’re participating in it. The show drops you into a richly realized world: the twin cities of Piltover and Zaun. They’re deliciously detailed. Steam comes out of vents on the ground, intricate architecture unfolds to the horizon, airships float by overhead, and a full populace ebbs and flows in the streets. All of this texture leaves the impression that you’re inhabiting a real, breathing world.

But what really instills the sense that you’re inside the story, instead of just watching it on a TV, is the way Arcane plays with perspective. Every scene is shot with a depth of field that yields a kind of three dimensional effect. Focal points are established so that you feel like you are there: like you’re looking up at a monster hulking over you, or peering down a narrow hallway straining to see what’s around the corner.

Most strikingly, the perspective frequently shifts from third-person to first-person. We might watch big sister and all around badass Violet sprinting across a rooftop and hurling herself into the air, and then cut to first-person as she/we look down to see the alleyway we’re leaping over rushing beneath our feet, and then look up just in time to see our hands bracing for impact as we roll and land on the neighboring rooftop.

See what I did there? That perspective shift, where you suddenly find yourself thinking you are that character, happens all the time in Arcane. We go from seeing a character looking at something, to looking at that something through their eyes. This is interesting beyond just the exhilaration of action sequences unfolding in first-person. It conveys emotional import. You feel bad when you watch a bigger kid picking on Violet’s little sister Powder. But you feel devastated when the scene suddenly switches to Powder’s perspective, and you see just how big and scary that bully is to her.

All of this makes me wonder: could this be a possible path for VR?

Arcane’s immersive effect would only be enhanced when viewed in virtual reality. In the simplest case, Arcane could remain exactly as is, but instead of watching it on your TV, you watch it inside a VR headset. Now it fills your entire field of view. In the same way that going from a small TV to a large one makes a movie more immersive, going from a large TV to a VR headset would take that effect even further.

It gets even more interesting though. Arcane could let you look around. Now you’re actually participating in it, controlling the perspective yourself. When Violet and Powder are walking down a crowded street, you could look over your shoulder to get a better look at a passerby. As they scramble the rooftops of Piltover, you could look up to watch that airship float overhead. And if the narrative has you worried that they’re being followed, you could look behind you to put your mind at ease.

Watching a show like Arcane in VR would be insanely cool… assuming there was a VR headset that I actually wanted to use.

Apple is widely rumored to be working on a VR headset. It’s surprising to me that there isn’t more buzz about this. If true, it could be a category defining product. Just as the iPhone completely changed what we thought we knew from Blackberries, it’s easy to imagine a VR headset from Apple causing us to look back and chuckle at today’s options. There’s still ample room for Apple to realize the ideal form of a VR headset. It’s early days.

Many of the issues that have plagued VR headsets to date are exactly the kinds of problems that Apple is exceptionally well-suited to solving. Today’s headsets are hot, heavy, and uncomfortable to wear for extended periods. They’re especially uncomfortable if you wear eyeglasses. The displays don’t have a high enough resolution to look visually stunning, and a combination of pixelation and low refresh rates can induce headaches (or worse).

If you do get a headset, unless it’s Facebook’s Meta’s Quest, you need a PC to drive it. And the specs are constantly outpacing themselves, such that you can’t simply get a VR headset, some new VR game, and assume it will “just work”.

And, frankly, the entire experience is awkward. Wearing a VR headset today completely isolates you from your surroundings. It’s disorienting. Some people can acclimate to this, but I bet most people won’t. It’s also easy to feel self-conscious, since the devices look dorky and their marketing leans weirdly into this.

Today’s VR headsets just aren’t very nice. But Apple could make one that is. They could draw upon their expertise from Apple Watch and Airpods to design a headset that’s light, breathable, and comfortable to wear for long periods of time. Just as they found a unique harddrive from Toshiba that made the iPod possible, it’s plausible that they could procure curved, Super Retina XDR-like displays that look phenomenal in a headset. And they could bring all of Apple Silicon to bear, building the computer right into the headset, so that no wires and no external computer is required. No specs to figure out. It just works.

Beyond making the headset itself nice, though, Apple is well-poised to make it nice to use. This may be what truly separates whatever Apple creates from the competition. It’s exactly the kind of design challenge – sitting at the intersection of human-computer interaction, technology, and the liberal arts – that is deep in Apple’s DNA.

Perhaps there’s a Transparency Mode to seamlessly switch from displaying VR to displaying your surroundings, just as AirPods can switch from noise cancelling to amplifying what you’re hearing around you. As with touch on the iPhone, it’s likely that Apple will discover novel ways to arrange and navigate UI inside VR, be it with controllers, gestures, or voice commands. And a VR headset could finally provide a good use case for Spatial Audio, so that if you wear your AirPods with the headset, the soundscape adjusts depending upon where you’re looking. That would be immersive.

All of these pieces could come together in a breakthrough product. Apple’s headset could finally bring VR from feeling unnatural to natural, so that it better fits into our lives. If the device looks good, feels good, and does cool things, VR could finally go mainstream. It helps that Apple’s product marketing is among the best in the world; the positioning would be less like this and more like this.

But even supposing Apple achieves all of this and ships an amazing VR headset, what are we going to do with it?

There will, of course, be many use cases. I hope the headset will serve as a tool for content creation: 3D graphics and modeling, video editing, coding… infinite Vim, anyone?! But in order to achieve the mainstream appeal that Apple will be aiming for, the headset will have to be great for content consumption.

Until I saw Arcane, I’d been scratching my head about this. Most VR content to date is in the form of video games, which Apple has been historically bad at supporting on their platforms.¹ And most of Apple’s customers aren’t serious gamers. Video games just don’t seem like a viable path for Apple to take their VR headset mainstream.

But Arcane showed me that VR movies just might be. Arcane is the demo that proves VR movies would be super cool, and my sense is that people will really like them. They would be way less awkward than VR games, which often degrade to waving your arms like a lunatic until ultimately knocking a lamp off the table. With VR movies, you’d just recline on the sofa, pull on the headset, and immerse yourself in another world for a couple hours. This seems like a fairly natural thing to do. For better or worse, people like passively consuming content. Instead of asking most people to do something completely new, VR movies would improve upon something they already do.

So I can see customers wanting to watch movies in VR.

I can also see Apple and the studios they’d partner with wanting to make them:

• Apple has the potential to make VR ubiquitous. To date, VR headsets just aren’t prevalent enough to merit investment from major film studios in a new content category like VR movies. But it’s feasible that Apple’s headset could eventually sell in volumes similar to, say, the iPad. ² This would be ubiquitous enough to cement the idea of VR movies in consumers’ minds, and to persuade film studios to make them.

• Apple TV+ is only expanding and would be a natural place for Apple to release “Made for VR” movies. This seems like a good strategy for them. In the streaming wars, exclusive content is key; this would be an exclusive category of content. And the “regular” version of these VR movies could still be viewed in TV+ on a normal TV, iPad, etc. Arcane demonstrates that you can still get a sense of virtual reality on a regular display. It wouldn’t be so unlike the 3D movies in theaters that also have a regular 2D option. Supporting both formats would avoid limiting marquee content to only those with a VR headset. It would also help create buzz to entice more people into getting one. I think this may be a theme for Apple’s VR headset overall: you can do something more immersively in VR, but there’s still a regular way to do it on your Mac, iPad, or iPhone.

• VR movies would fit into Apple’s design philosophy of tight vertical integration. They would have total control over the content, its distribution, and the hardware it runs on in order to create the best possible experience. Interestingly, this may appeal not only to Apple but also to some of Hollywood’s most progressive directors like James Cameron, Peter Jackson, and Christopher Nolan, who are famous for pushing the technical boundaries of their films and wanting total control over how they’re screened. It’s a stretch, but they might go for an exciting new technology platform with strong guarantees over what the end viewer will experience. And Apple may now actually have the connections to court filmmakers of their stature, thanks to these past years working with Hollywood for TV+.

• The video game industry only continues to grow. It surpassed the film industry a long time ago. There’s a ton of content to leverage in video games, and a ton of money being spent on that content (look no further than the recent acquisitions of Weta, Activision, and Bungie). So there’s certainly desire to maximize revenue from that content. VR movies could grow the market by bringing all that content to a broader audience, beyond gamers. Just as Arcane came out of League of Legends, video games seem like a great source for VR movies, at least initially. Animated films more naturally fit the medium than live action, game engines are probably the right technology for rendering movies where the viewer can control the camera, and game studios have the talent and domain expertise in creating immersive worlds.

• There’s been a shift from movie-theater going to home streaming. If this is a trend that continues past the pandemic, then Hollywood will need to figure out a way to monetize releasing blockbuster films straight to the home, and a new high-end VR movie platform could be one answer.

I have no idea if VR movies will actually become a thing. There are so many open questions, starting with if Apple is actually going to make a VR headset. And if they do, am I right that people will want to watch movies while wearing it? What if it’s family movie night – does everyone wear a headset? That gets expensive fast. What if it’s date night? That’s just weird.

I think these questions point to how VR isn’t going to be instead. It’s going to be in addition. I hope VR movies will be one such addition, and I’m curious what the others will be. It’s exciting and a little wild that an entirely new mode of computing could be right around the corner.

04 Nov 2021

How To Get Really Good At Something

You can get way better at most things than you think. The first step is to identify what you want to get really good at and then just start.

Don’t directly compare yourself to others at the top of the field. You’ll inevitably fall short, and it will be demoralizing. It’s good to be inspired by them, but you want to measure against your previous self. Try to get a little bit better each day. If you do this for long enough, you’ll be amazed by the results.

You will improve fastest by working with others who are better than you. Seek them out. This becomes easier as you gain in skill and start to feel more confident approaching them. You will also have more opportunities to do so, since impressive people tend to operate in fairly tight-knit networks.

You have to invest a lot of time and energy to get really good at something. You have to get obsessed; thinking about it all the time, even when you aren’t doing it. You have to let it take over your life. This will mean neglecting most nonessential things and carefully nurturing the few essential things (family, close friends, personal health, maybe one or two other personal pursuits) that remain.

Be very intentional in deliberately practicing your craft. When you’re on, you should be completely on, performing bursts of intensely focused work. Don’t fall into the trap of working long hours but never really getting anything done. It’s tempting to do this, consoling yourself that the long hours must mean you are improving. But you aren’t; you’re just avoiding the real work that you must push through in order to improve.

These are the trappings of working on something other people wanted you to do. But you’re working on something you want to do. You are accountable only to yourself, so forget appearances and shed extant bad habits. Your results are what matter. Your process only matters insofar as it gets you the results. This is intimidating but also extremely liberating.

The best approach looks something like two blocks of time intensely focusing on your craft, and then spending the rest of the day resting, thinking about it in the background, and tending to everything else in your life. It will of course depend upon what you are pursuing.

For all this to work, you have to genuinely love what you’re doing. Discovering what you love to do will feel like a revelation, as though a little furnace of energy is burning inside you. It will bring out your most authentic self. You’ll feel compelled to do it. If the thing you’re pursuing doesn’t feel this way, you’re unlikely to become truly great at it. Keep looking; as Steve Jobs imparted, “You’ll know when you find it”. It is such a rare privilege if you do.

You probably only have room to become truly great at one or two things. So choose wisely. You should try to find something that really matters. My metric is that the pursuit should benefit others in some way. Writing is one example, because great writing benefits anyone who reads it. Don’t worry about this too much though. Once you get really good at something, you’ll have so much leverage with it that you’re sure to find some way it can be used to help others.

So the best way to identify what to get really good at is to just follow your nose until you find what you love to do. Once you have, it will feel so inevitable that you’ll happily realize you likely didn’t have much of a choice in the matter anyways.

20 Oct 2021

Some Thoughts on Apple's 'Unleashed' Event

In the order that they were announced:

Apple Music Voice Plan

Amusingly, this could be viewed as an upgrade instead of a budget option. You get to pay less and you don’t even have to use the clunky Music app!

In all seriousness, I bet there are plenty of people who just want to be able to stream music while driving, exercising, etc., don’t care much about curating a library or browsing content, and are perfectly happy to just have a “smart radio” that they command through Siri. And I bet there are also plenty of people who won’t pay $9.99 / month for music, but who will pay half that. Apple will never break out the numbers, but it will be interesting to see what analysts estimate the uptake of this plan actually is.

Speaking of numbers, I assume Apple can’t offer a free tier since they don’t do ads. But perhaps they can offer this lower $4.99 pricing for the Voice Plan because they’ve worked out a deal where they pay the record labels less for music the end user streams via Siri? The record labels have a lot of weird and arbitrary rules, and pricing their content based on how the listener accesses it is one of them.

HomePod Mini Colors

Ordinarily, adding three new colors to a product priced at $99 would mean Apple is going to sell them like hotcakes for the holiday season. I’m not sure that’s going to happen here. The new colors don’t actually look that good to my eye. Which is rare; Apple’s colors are normally very on point. But even if most people like the new colors more than me, the HomePod Mini still doesn’t seem to have found product market fit. So it’s unclear how much a few new colors will help.

I personally love my original HomePods… or at least the ideal of what they could have been. So the new HomePod Mini colors are heartening to me, if only because they indicate Apple is still actually thinking about and investing in this area.

Which is strategically good for them. As they continue to expand the Apple Home software layer, they need a solid physical presence in the home to underpin it all. I really hope Apple revamps the HomePod product line, and doesn’t just abandon the original, larger speaker. It could also be so much more than a speaker: mesh wifi router, a FaceTime device… It has unrealized potential that I’d love to see Apple take another crack at. Plus it’s really incongruous to have a HomePod Mini when there’s no HomePod “regular”.

AirPods 3

I’m totally obsessed with my AirPods Pro, so these aren’t for me, but it’s great to see the regular AirPods getting some upgrades. It’s also great to see the previous 2nd generation remaining in the product lineup, offering a more affordable option. But even at $129, they’re still pretty expensive for a pair of ear buds that are easy to lose. Why can’t they be $99?! That would sell like hotcakes for the holiday season.

M1 Pro and M1 Max

Names first. Everyone’s been debating if the new chip would be the M1X (in the A*X tradition) or if Apple would go straight to the M2. Surprise! It’s neither.

M1 Pro seems like a good name. The M1 is in the MacBook Air, the M1 Pro is in the MacBook Pro. Makes sense.

M1 Max is a bit strange. With iPhones and AirPods, “Max” denotes “physically larger”. And while the M1 Max is literally larger, that’s irrelevant since nobody except nerds will ever even see it. What “Max” really means here is “even more powerful”. M1 -> M1 Pro -> M1 Max.

Oh well. In the end, the names are short, so they’re good. People will quickly stop thinking about it and just use them: “Are you going to get the Pro or the Max”? But the delineation isn’t as clear as it could be.

Names aside, these chips seem like they will absolutely shred. I have yet to experience a single performance hiccup on my M1, and the M1 Pro and M1 Max are going to scream compared to it: 70% faster CPU than the M1, and 2x - 4x faster GPU. It makes me wish I actually needed them. But I’m excited for the real pros who do!

MacBook Pros

So as impressive as the new chips are, what I’m more excited about is the notebook’s new design.

The new XDR display is going to look phenomenal, and the thinner bezels provide extra screen real estate for the same physical footprint. The raised feet, squared chassis edges, and matte black keyboard all look super Pro. They make one want to rub their hands together and proclaim “Let’s get to work!”. And since we’re all still stuck in the land of video calls, the 1080p camera is going to be really nice.¹

I ordered the 16” with the M1 Pro chip. I’ve historically used a 15” MacBook Pro for the larger display, so when I stepped down to the 13” Air in order to get the sweet new M1 chip, it was always with the idea that it was a stopgap for these machines. Now that they’re finally here, I’m surprised to find I’ve developed an affection for my little Air and am sad to move on. But I’m going to be coding exclusively on a laptop without an external display for a while, and the 13” Air is a bit cramped for this. Hence, upgrade. Anyways, I’m sure these feelings of fondness will immediately fade when I first power on my lean, mean, Pro machine.

The “Unleashed” moniker for this event was clearly referring to the new M1 Pro and M1 Max chips and what these new MacBook Pros can do with them. But it might as well refer to Apple the institution, because they’re finally unleashed to make insanely great tools for Pros.

First, unleashed from Intel and their performance plateaus. It’s notable that this is the first time you can spec up the smaller MacBook Pro just as fully as the larger one. In the past, this just wasn’t possibe because Intel’s more powerful chips ran too hot for the smaller chassis / battery. This eliminates the tradeoff of form factor vs. computing power. Now you can just select your preferred size and specs independently.

Second, Apple’s unleashed from the Jony Ive design era’s relentless pursuit of minimalism. After an extremely frustrating stretch for the MacBook Pro, Apple is adding all the ports back (goodbye, messload of adapters!), adding physical function keys back (goodbye, TouchBar! Hello, physical and full-size Escape key!), and even made the machines the tiniest bit thicker. I doubt the extra thickness will be noticeable in practice, but it says a lot in principle about the new design philosophy. Form is no longer prioritized over function at all costs, and Apple is once again taking into consideration what people are actually trying to do with their machines. Awesome.

Wishful Thinking

I was really hopeful that Apple would release a standalone Retina display to go along with these machines. It seemed possible, since the two would have presented perfectly together. I really want an Apple-engineered, Retina quality display. I really don’t want to pay $6,000 (!!!) for their Pro Display XDR. And I also don’t need its reference monitor functionality. I just want a 27” - 30” Apple display that has Retina resolution, looks great on my desk, and works seamlessly with my Macs.² There’s rumors that an Apple display for the rest of us is in the works… I sure hope they’re true.

24 Jun 2021

Leadership Lessons From Shackleton's Incredible Voyage

In 1914, Ernest Shackleton set sail for Antarctica with a team of twenty-seven men, aiming to be the first party to cross the continent overland. But when the Endurance became locked in pack ice, Shackleton’s objective changed from setting a new record to simply getting his team out alive.

Endurance: Shackleton’s Incredible Voyage recounts his team’s legendary feats in doing so, from schlepping across treacherous ice floes, to sailing a lifeboat through the roughest seas in the world, to climbing across South Georgia Island’s presumed impassable interior in order to finally reach help.

Individually, each of these would make for an incredible achievement. Taken together, all whilst facing extreme cold and starvation, they are truly extraordinary. Shackleton prevailed against seemingly impossible odds and made history by getting every single one of his men home safely.

How did he do it? What were the qualities that caused Sir Raymond Priestley, another Antarctic explorer and contemporary of Shackleton’s, to proclaim:

For scientific leadership give me Scott; for swift and efficient travel, Amundsen; but when you are in a hopeless situation, when there seems no way out, get down on your knees and pray for Shackleton.

Here are some aspects of Shackleton’s leadership that struck me while reading this fabulous book.

Do What You Love.

To be truly great at what you do, you have to love doing it. Shackleton loved exploring the Antarctic.

His first expedition was under Robert F. Scott in 1901 and got the closest to the South Pole to date. He then returned with his own expedition in 1907, aiming to reach the Pole:

With three companions, Shackleton struggled to within 97 miles of their destination and then had to turn back because of a shortage of food. The return journey was a desperate race with death.

Despite this life threatening close call, Shackleton was already considering his next expedition even before returning home. He was only fully alive when he was exploring the Antarctic.

Figure Out What Really Matters. Let Everything Else Go.

When disaster strikes and the Endurance becomes trapped in the ice, Shackleton fully commits to getting his men home safely. This may seem obvious, but less so is how he jettisons his concerns over everything else. Merely ensuring his men’s survival is going to take every fiber of his being, and so distraction means death.

Early on, before the Endurance gets crushed and when it is merely stuck, Shackleton could still have pursued his original goal of crossing the continent. But to do so would have incurred additional risk for the rest of his men, and since saving them had become his raison d’etre, he didn’t even consider it. This is very significant, as he’d spent over two years preparing (and fundraising) for the trip, and felt this expedition was the last real opportunity for glory in the Antarctic.

In addition to letting go of distractions, Shackleton seemed to let go of his fears. He must have carried them deep down, but he was so wholly set on getting everyone home safely that there simply wasn’t room in his mind for considering the possibility of failure. This prepared him to lead his team through seemingly impossible challenges that under any other circumstances he and his men wouldn’t even consider undertaking.

Pick Good People.

It may be called Shackleton’s Incredible Voyage, but it couldn’t have been completed without a phenomenal team. Shackleton built his team around a nucleus of tested veterans, all 5 of whom he’d been on previous Antarctic expeditions with. These were the best of the best, and Shackleton had the first hand experience to be sure of it.

He selected Frank Wild as his second-in-command; if the expedition were a startup, Wild would be his cofounder. Wild was one of Shackleton’s three companions in the 1907 race for the pole where they faced starvation, and Shackleton “had developed a tremendous respect and personal liking for him”. Similarly,

Wild’s loyalty to Shackleton was beyond question, and his quiet, somewhat unimaginative disposition was a perfect balance for Shackleton’s often whimsical and explosive nature.

This complementary relationship proved key time and again, especially when circumstances required that they split in two, with Shackleton leading one group and Wild the other. It’s hard to imagine things turning out the way they did if Shackleton didn’t have Wild to depend on.

Lead By Example. Put Your Team Before Yourself.

Shackleton is every bit a member of the team. He seems to always take the first night shift watching for deadly cracks in the ice beneath them. He does his full share of the menial chores, like ferrying the pot of hoosh (yum…) across the freezing cold between the stove and his tent mates. He takes part in all of the men’s social activities, including teaching many of them how to play bridge.

He never asks anything of the men that he won’t do himself. When he implores them to travel as light as possible, he dumps his own personal belongings into a small pile of things to be left behind. Shortly thereafter, that small pile grows into a mountain as the rest of the men follow his example.

He demonstrates that the team’s safety is his top priority in everything he does. When the ice that Shackleton and a handful of men are camped on splits off from the main floe, Shackleton sees that every man makes it safely across before he sees himself across.

This unwavering commitment to his men engenders their complete faith in him, which they honor even when he makes big decisions that they don’t all agree with.

Decide Quickly. Update As Needed.

Shackleton is extremely decisive. Before bed, he will write in his journal that he is considering something, and the next morning he will announce it to all hands. He makes hugely difficult decisions on imperfect information, and he never lets uncertainty overwhelm him into inaction.

Instead, he simply makes the best choice he can with the information he has. The key to this approach, though, is how he revisits decisions and quickly course corrects when he gets new information.

After the men abandon the Endurance, they camp on an ice floe they’ve affectionately named “Ocean Camp”. The hope is that the wind and current will blow the ice pack in the direction they need to go, helping them reach the Palmer Peninsula. However, after weeks of waiting, they’ve made little progress, and morale is declining.

Shackleton therefore decides that instead of relying on the wind, they will take matters into their own hands and march across the ice pack. This is not a popular decision, and many members of the party feel they should stay put and bide their time.

It turns out to be a bad call. After five days of exhausing struggle, the party has only covered nine miles out of the 200 required to reach the peninsula.

Rather than doggedly stick with the decision, Shackleton reassesses and reinstates the waiting strategy. They form a new camp and return to relying on the wind to blow them in the right direction. It does, and finally gets them far enough that they can take to their boats.

Once they do, over the course of five harrowing days at sea, Shackleton repeatedly updates their target based on the wind and currents. Initially, they aim for Clarence/Elephant Island; then, King George Island; then Hope Bay at the tip of the Palmer Peninsula, and then finally, back to the original target of Elephant Island, where they ultimately land.

This wasn’t poor leadership or haphazard planning; this was high-resolution decisionmaking as conditions unfolded and rapidly changed, and it’s what ultimately saw them to land.

Shackleton doesn’t have to be perfect at deciding because he is really good at re-deciding. In this way, he ensures the party is always making forward progress towards its goal in the best way presently possible.

Move Fast.

Once he makes a decision, Shackleton moves fast to execute it. He sets his team to action right away, which leaves no time for debate or second guessing.

More generally, he knows that time is of the essence, and that he is in a race against starvation and freezing to death. He brings incredible intensity to every single day. It is amazing how much you can get done, and in how little time, when you operate this way.

One striking example: Upon surviving the week long journey across the Drake Passage to reach South Georgia island, Shackleton rests for only a few days before setting out with a small party across the island’s interior. And upon finally reaching the other side, he waits even less than that before forging his rescue attempt for his marooned men.

Shackleton is a relentless force of nature.

Leadership Is Lonely.

I am rather tired. I long for some rest, free from thought. -Shackleton’s diary

Shackleton bears an incredible and lonely burden. He must always project absolute confidence to his men, which means he can’t ever confide his own fears and uncertanties to anyone else.

Beyond this, no one else is quite experiencing what he is. As expedition leader, he alone is responsible for the fate of the party, and so he alone knows what that responsibility feels like.

You Still Need Some Luck.

Even with all of the genuinely great leadership described above, there are still inflection points where the expedition’s survival hinges entirely on luck.

At one point, while waiting out the wind on the ice, the party comes to the brink of starvation. With winter approaching, most of the wildlife has migrated, and there hasn’t been a successful hunt in weeks. Then, miraculously, an entire penguin rookery moves onto their ice floe in the middle of the night, supplying them with all of the meat they need in their most desperate hour.

There are many examples like this - including that the wind didn’t just blow them out to the open sea, which was a very real possibility - but maybe the most remarkable bit of luck is at the very end of Shackleton’s journey.

Shackleton has made it across the pack ice; up the Weddell Sea to Elephant Island; and finally across the Drake Passage to South Georgia Island. Help is just on the other side of the island, but the currents are so dangerous they can’t sail around it. So, Shackleton and two men set out to cross the interior. This has never been done before and the island’s craggy peaks are considered impassable. Night is setting in as they reach the top and the three men are facing freezing to death at their elevation. There’s no time to safely descend, and even if there was, the visibility is so poor that they wouldn’t be able to make out a path.

So Shackleton rolls the dice and proposes their only option: that they slide down into the abyss. After almost two years of struggle and meticulous decision making, the success of their voyage literally comes down to sliding on their butts and hoping they don’t plummet to their death. Luck was on their side and they smoothly slid until safely bottoming out 2,000 feet lower in a snowbank.

Don’t Give Up.

Shackleton’s family motto was Fortitudine vincimus – “By endurance we conquer.” Nothing better epitomizes his incredible voyage. There are so many moments where sheer perseverance is what sees him and his men through. This serves as a powerful example for all of us. When we are in our own struggle, underlying everything is to just keep going. You can’t succeed if you stop.

09 Jun 2021

Well, It's About (Face)Time

There isn’t an insanely great video call service for personal use. Zoom, which became the de facto standard during the pandemic, was really meant for the enterprise, and it shows in everything from their pricing plans to their UI. To my mind, FaceTime has always come the closest, but certain limitations have forced me into Zoom, Google Meet, etc. when video chatting with family and friends over the course of the pandemic this past year.

These are the three primary limitations I’ve run into:

• FaceTime is only available to people in the Apple ecosystem. This rules it out when a member on the call is an Android or Windows user.
• There’s no way to send a link for a call ahead of time. This rules FaceTime out for events that are important to plan ahead, like a virtual wedding ceremony.
• FaceTime isn’t great for calls with many participants. Despite adding support for Group FaceTime (up to 32 participants) in 2018, it’s pretty impractical to actually use for this. The floating UI layout looks neat, but doesn’t handle well outside of a slick demo.

This year’s update to FaceTime feels like the team went heads down during the pandemic, dug in, and determined to make it an all around viable option for personal video calls. In doing so, they’ve addressed each of these three limitations.

First, FaceTime will now be available in the browser, making it an option for people outside the Apple ecosystem. Steve Jobs famously promised that FaceTime would be made an open standard 11 years ago, much to the surprise of not only the audience at WWDC 2010, but also to FaceTime’s own engineers! While this year’s update still doesn’t make FaceTime an open standard, it does bring it to all major platforms (via the Web). Presumably this addresses the primary goal Jobs had in mind when he shot from the hip on stage so many years ago.

Second, users will be able to create a link to an upcoming FaceTime, which makes it possible to schedule and share a call in advance. And third, Apple’s adding a standard grid view to FaceTime calls, which looks a lot more practical for doing calls with a large number of people: everyone remains fixed in the same position on the screen for the duration of the call.

None of these features are novel. All major video call services offer multiplatform support, URL’s to upcoming calls, and grid view. But bringing these features to FaceTime is still notable. It takes FaceTime from something that works great for certain use cases to something that can work great for all use cases. At least that’s what I hope will happen… the ingredients are finally all here; now Apple just needs to actually deliver on them. ¹

Today’s announcement isn’t limited just to laying a better foundation though. There’s some really cool, novel features that I’m eager to try out too.

Portrait Mode is the marquee feature, at least for me. It squarely solves two things that are always top of mind when I join a video call: I want to look my best and I want my background to be nice. Zoom’s virtual backgrounds, which completely replace your actual background with a photo of something like the Golden Gate Bridge, are too superficial and distracting for my taste. And while apps like Webex offer “Background Blur”, it’s janky. The blur opacity often isn’t quite right and the edge detection on the subject (me!) is often flakey, doing weird things like cutting off my arms when I gesture with my hands.

Apple’s deep expertise and history with Portrait Mode from all their camera work leaves me optimistic that this will work great in FaceTime. I hope it brings out good lighting and features on my face and pleasantly blurs everything that’s behind me. I’d love the blur to leave everyone else with a sense of the space but not the specifics. We’ll see how it performs in practice, but the demo looked great.

Unsurprisingly, the product marketing is superior to the competitors here too. Webex’s “Background Blur” sounds like I’m hiding something; Apple’s “Portrait Mode” sounds like I’m presenting my best self. Nice.

Voice Isolation eliminates background noise so that you can hear the speaker clearly. Apple did a cute demo where a kid is playing with a leaf blower in the background. It sounds like a tornado until Voice Isolation comes on, after which the speaker’s voice becomes crystal clear. ²

Spatial Audio makes it sound like the audio is coming from wherever in the grid the speaker is located. Will this really make a difference for making conversations feel more natural? I have no idea, but I’m glad that Apple is experimenting with things to help reduce the cognitive dissonance of hanging out virtually. ³

And then there’s SharePlay, which lets you sync music and movies with the other members of your FaceTime call. I would have loved this when I was in a long distance relationship; at the time the state of the art was “One, two, three… play!” Woe unto the person who gets up to fetch a snack. There’s a slew of dead (and typically illicit) apps that have tried to solve this through something like a browser extension. None of them possessed both the deep integration into the platform and the partnerships with the content providers that are required in order to really do this right. But Apple does; that’s the power of them fully owning their platform in action.⁴

I can’t help but feel a little bit of irony in Apple announcing all of these phenomenal video calling features right as we are coming out of the pandemic. And I’m sure they would have liked to ship these features sooner, when we all so desperately needed them, too! But my guess is that even if they were willing to break rank with WWDC and ship early, they wouldn’t have been ready to. Even now, FaceTime engineers are probably frantically scrambling to get all of this stuff ready for the Fall.

Regardless, it’s (obviously, without question, times 1000) a great thing that we’re coming out of the pandemic, and we must of course be sensitive to the fact that the same can’t be said for everyone, everywhere. And while we may no longer need these features quite so desperately, remote work and virtual socializing are here to stay. I just hope that Apple’s commitment to making FaceTime insanely great is too.

06 Feb 2021

How Will You Measure Your Life?

In How Will You Measure Your Life, Clayton Christensen begins by observing how despite tremendous professional accomplishments, many of his peers were clearly unhappy in life. Their unhappiness included personal dissatisfaction, family failure, professional struggles, and even criminal behavior. And yet each of them had started out as good people who somehow let forces and decisions derail them along the way.

Knowing that we are all vulnerable to these forces, he set forth to apply business theory (statements of what causes things to happen–and why) to the individual. Instead of using businesses as the case studies, he suggests we use ourselves. In doing so, Christensen provides frameworks for each of us to answer:

How Can I Be Sure That:

I will be successful and happy in my career?

My relationships with my spouse, my children, and my extended family and close friends become an enduring source of happiness?

I live a life of integrity—and stay out of jail?

He notes that while these are simple questions, answering them is very hard work and part of a continuous, ongoing journey through life. He hopes that at the end of that journey, the theories in his book will help you definitively answer the question: “How will you measure your life”?

The book is fairly short and very worth reading in full. Doing so provided me with the time to really internalize the material and to start actually applying it to my own life.

At the same time, I find myself wanting a distilled version that I can reference from time to time, in order to correct my own course as I chart it through the “seas of life”. If I had to compress the entire book down into a recipe, it would be:

1. Figure out the things that actually make you happy
2. Be open to unexpected opportunities until you land on a career that lets you realize those things
3. Always monitor where your time and energy is going, to ensure what you’re actually doing is what you intend to do
4. Always be investing in your relationships
5. Clearly establish your personal moral code and never make exceptions to it

But there is so much good stuff behind each of these, that I think a more detailed outline of notes is the sweet spot for a proper reference manual. Here it is.

The Power of Theory

• There are no easy answers to how to find happiness and meaning in life.
• The book instead provides tools (the theories) to help you make good choices appropriate to the circumstances of your own life.
• Instead of telling you what to think, it will teach you how to think.
• Good theory is a general statement of what causes what, and why. It is universal, and not only true in certain circumstances.
• This means it can help us predict:

  People often think that the best way to predict the future is by collecting as much data as possible before making a decision. But this is like driving a car looking only at the rearview mirror—because data is only available about the past. Indeed, while experiences and information can be good teachers, there are many times in life where we simply cannot afford to learn on the job. You don’t want to have to go through multiple marriages to learn how to be a good spouse. Or wait until your last child has grown to master parenthood. This is why theory can be so valuable: it can explain what will happen, even before you experience it.

• Being able to predict means we can use the theories to help steer us to good decisions and build the lives we want to live.

Part I: Finding Happiness in Your Career

The only way to be truly satisfied is to do what you believe is great work. And the only way to do great work is to love what you do. If you haven’t found it yet, keep looking. Don’t settle. As with all matters of the heart, you’ll know when you find it. – Steve Jobs

• We should strive to reach a point where we wake up every morning loving what we do.
• We need to build a strategy to achieve this.
• A strategy is what you want to achieve and how you will get there.

• Three things build our strategy: priorities, balancing plans with opportunities, and allocating our resources.

• Priorities
  • Our priorities need to be set according to what will make us happy.
  • To do so, we need to fundamentally understand what motivates us.
  • Incentive theory says that to get people to do something, you just need to pay them to do it.
  • This theory is flawed, because it can’t explain powerful anomalies, such as highly happy and motivated individuals doing amazing work at nonprofits for little to no pay.
  • What truly motivates people, then, if not money?
  • Motivation theory says that incentives are not the same as motivation.
  • True motiviation is people doing something because they want to do it.
  • Satisfaction and dissatisfaction are separate, independent measures. This is why it is possible to love and hate your job at the same time.
  • Hygiene factors are elements that will cause us to be dissatisifed: compensation, job security, work conditions, company policies…
    • Compensation is a hygiene factor, not a motivator. ¹
    • At best, improving hygiene factors just means you won’t hate your job. It does not mean you will love it.
  • Motivators are what will truly, deeply satisfy us and cause us to love our jobs.
    • Doing work that is truly meaningful to us, is interesting and challenging, allows us to grow personally and professionally, and that provides opportunities for increased responsibility.
  • Most of Christensen’s peers who found themselves unfulfilled in their careers had chosen them using hygiene factors as the primary criteria; income was often the most important of these.
  • Rationalizing that you’ll take a job for compensation now so that you can pursue a job you’ll actually love later rarely works. Lifestyle inflation and losing track of the dreams you had in the first place make it really hard to wind it back and correct course. ²
  • Aside: If done well, being a manager is one of the noblest professions of all, because you have the opportunity to frame each person’s work such that their life is filled with motivators. ³
  • Once you get the motivators right, the more measurable incentive factors will fade in importance (but will also naturally fall into place).
• Balancing Plans with Opportunities
  • Knowing our priorities is only half the battle.
  • We then have to actually find a career that both motivates us and satisfies the hygiene factors.
  • We have to balance the pursuit of our aspirations and goals with taking advantage of unanticipated opportunities.
  • Options for your strategy spring from two very different sources.
    • The first source is anticipated opportunities: the opportunities you can see and choose to pursue. Pursuing these is your deliberate strategy.
    • The second source is unanticipated options: a mix of problems and oppportunities that arise as you are executing your deliberate strategy.
  • These unanticipated options then fight with your deliberate strategy for resources.
  • The new strategy that forms from these unanticipated options is your emergent strategy.
  • Over time, your emergent strategy becomes your deliberate strategy, and the cycle repeats, constantly evolving.
  • We are constantly navigating a path by deciding between our deliberate strategies and the unanticipated alternatives that emerge.
  • Understanding this will help you sort through the choices that your career will constantly present.
  • Which you choose depends upon where you are in your journey:
    • If you have found an outlet in your career that provides both the requisite hygiene factors and motivators, then a deliberate approach makes sense. Rather than worrying about adjusting to unexpected opportunities, your frame of mind should be focused on how to best achieve the goals you have deliberately set.
    • If you haven’t found a career that does this for you, then you need to be emergent. Experiment in life. As you learn from each experience, adjust. Then iterate quickly. Keep going through this process until your strategy begins to click. ⁴

    • What’s important is to get out there and try stuff until you learn where your talents, interests, and priorities begin to pay off. When you find out what really works for you, then it’s time to flip from an emergent strategy to a deliberate one.

  • It’s easy to say to be open to opportunities as they emerge; it’s much harder to know which to actually pursue.
  • A tool that can help is to ask: “What has to prove true for this to work?”.
    • What assumptions must prove true in order for me to succeed? Are they in my control?
    • What assumptions must prove true for me to be happy if I go for it?
    • Then swiftly and inexpensively test if these assumptions are valid.
• Allocating Resources
  • You’re aspirations and intentions don’t mean anything until you align them with where you actually expend your time, money, and energy.
  • If your resources aren’t supporting the strategy you’ve decided upon, then you’re not implementing that strategy at all.
  • How you allocate your resources can make your life turn out to be exactly as you hope or very different from what you intended.

  • How do you make sure that you’re implementing the strategy you truly want to implement? Watch where your resources flow—the resource allocation process. If it is not supporting the strategy you’ve decided upon, you run the risk of a serious problem. You might think you are a charitable person, but how often do you really give your time or money to a cause or an organization that you care about? If your family matters most to you, when you think about all the choices you’ve made with your time in a week, does your family seem to come out on top? Because if the decisions you make about where you invest your blood, sweat, and tears are not consistent with the person you aspire to be, you’ll never become that person.

Part 2: Finding Happiness in Your Relationships


• There is much more to life than your career.

• Work can bring you a sense of fulfillment–but it pales in comparison to the enduring happiness you can find in the intimate relationships that you cultivate with your family and close friends.

• They are worth fighting for.

• Techniques for nourishing these relationships:
  • Give them consistent attention and care.
  • This is surprisingly difficult to properly invest in, because:
    1. You’ll be routinely tempted to invest your resources in other things (like your career) that provide a more immediate payoff, and
    2. Your family and friends rarely shout the loudest to demand your attention.
  • So you have to always be investing in your relationships.
  • Think from the perspective of the other person: what do they need from you? What “job” does my spouse most need me to do?
  • You then have to actually do that job. This will require sacrifice, but that sacrifice will deepen our commitment, and ultimately happiness.

  • The path to happiness is about finding someone who you want to make happy, someone whose happiness is worth devoting yourself to.

Part 3: Staying Out of Jail

• Everybody thinks they have integrity, and nobody sets out to live a life without it.
• The trap is that it is easy to make a small compromise, “just this once”, in order to get an edge or get ahead. Once people start down this path, it is hard to turn back.
• The marginal cost of doing something “just this once” always seems to be negligible, but the full cost will typically be much higher.

• But looking back on it, I realize that resisting the temptation of “in this one extenuating circumstance, just this once, it’s ok” has proved to be one of the most important decisions of my life. Why? Because life is just one unending stream of extenuating circumstances.

• Decide what you stand for. And then stand for it all the time.

Finding Your Life’s Purpose

• The type of person you want to become – the purpose of your life – is too important to leave to chance.
• You have to answer the question: who do I want to become?
• This is worth investing in, because once we figure it out, we will apply it to aspects of our life every single day.

• The only metrics that will truly matter to my life are the individuals whom I have been able to help, one by one, to become better people. When I have my final interview with God, our conversation will focus on the individuals whose self-esteem I was able to strengthen, whose faith I was able to reinforce, and whose discomfort I was able to assuage–a doer of good, regardless of what assignment I had. These are the metrics that matter in measuring my life.

• If you take the time to figure out your purpose in life, you’ll look back on it as the most important thing you have ever learned.

23 Jan 2021

Building Your Startup's Founding Team

The most impressive thing we built at Accompany was our team. Years from now, what I’ll recall most fondly won’t be the product we created or the outcome we had, but the incredible people I got to work with. Assembling such a high quality team was super hard, so I’d like to capture here how we went about it, focusing on the very first step: sourcing great candidates.

Our best source of candidates, by far, came from within our own personal networks. This is an amazing bit of bootstrapping to see in action: our first key hires landed us our next key hires, and so on. Once we hit a critical mass of like minded individuals who enjoyed working together, a positive feedback loop formed, attracting more like minded individuals in turn.

This is not a particularly novel idea, and lots of super stacked technical teams (Dropbox, for example) have talked about leveraging it in their early days. What I hadn’t heard them talk about (beyond “call up all your friends from MIT”) was how exactly to go about it.

We discovered a few key ingredients.

First, it’s essential that your first few hires be absolutely phenomenal. Do not compromise on this in any way! Since the first key hires will seed the next N hires, if the first are even slightly suboptimal fits, those next N will be too. Happily, the opposite also holds: if the first key hires are phenomenal, their referrals will be, and in a way where the value they add is multiplicative, not just additive, thanks to the magic that happens when you get these kinds of people together in a room. So be extremely intentional in making these first key hires and do not compromise in any way.

What does it mean for a hire to be absolutely phenomenal? This will look different from startup to startup, depending upon the kind of company you are building. But there will be shared traits:

• they are great at their craft
• they can operate autonomously
• you can trust their judgement completely
• they have an owner’s mindset
• they actually ship
• they are extremely high integrity individuals who share the company’s values and care deeply about its mission

The best way to be certain that someone possesses all of these attributes is to have worked with them before and/or known them for a very long time; ideally both. Which speaks to why recruiting the first ten hires or so (let’s call it the founding team) from within the founders’ and existing team’s personal networks is essential.

Once you have assembled the founding team, amazing candidates unfortunately do not just start magically showing up at your door. Drats! You have to get the founding team organically recruiting their friends and colleagues to come join in turn. This was a really big barrier for us to break through at Accompany. It ends up that getting people to tap their personal network is a tall order: they have to let the startup become a part of their identity, tie their reputation to it, and spend a lot of time and energy outside of their official job description on recruiting.

How do you overcome this? Like most challenges startups face, the answer is straightforward but difficult: hit growth and make it a fabulous place to work. If your startup is going places, and if getting there is fun, the referrals will follow. You’ve made it easy for everyone. The founding team would almost feel bad not recruiting their friends, and their friends will really want to be recruited.

That was how things unfolded for us. After some initial success where the founding team recruited friends purely on the mystique of a pre-launch startup, things stalled out. This coincided with when we entered into the Trough of Sorrow after we launched. Once we found product market fit and started to grow, people resumed recruiting from their personal networks.¹

Even then, though, the actual practice of recruiting is a ton of work and takes discipline. Everyone has a million things to do, and especially for hackers, anything other than, well, hacking, feels like a distraction. So you have to rewire your own brain and the rest of the team’s to recognize that recruiting is real work, and to be very intentional about making time for it. Once a month, we’d sit down with everyone 1:1 and brainstorm who they might check in with, and how we could best tailor our recruiting process to that candidate’s needs. This could range anywhere from just getting coffee to inviting them to come meet the team over lunch to actually having them interview with us, if the timing was right. It was always all about the candidate and what would be best for them, given their current circumstances.

To that end, you have to treat these referrals with extra care. High quality referrals do not grow on trees! You already know the candidate is phenomenal — that’s why they’re a referral! And yet for some reason, it’s all too easy to lapse into the default of just sending them through your standard interview track. This is a mistake and a waste of everyone’s time. (Not to mention embarrassing for the person referring them.) Instead, you should treat them like a very special guest. Invite them to come have dinner with the team² to let them gauge if they’re as excited about you as you are about them. If they are, invite them to come hack for a day (or more!) to test run what it’d really be like to work at your startup. This lets them pair program with a few different members of the team so that everyone can really get a feel for working with each other. For us, this ended up providing way more signal than a standard interview would have, and referrals loved it for the same reason. As an added bonus, if the referral did decide to join, they’d hit the ground running because they’d already started getting up to speed during the test run.³

Lastly, and underlying all of this, is that you have to be patient and hold the long view. Everyone will be looking to refer the two or three most talented individuals they know, and such talented people are rarely available. They’re almost always already working on something super interesting and pretty committed to it. That’s ok — you just take them whenever they’re ready. It’s the only way to get them, and it will be very worth the wait.⁴ But when they do become available, they tend to decide quickly. It’s too late to start the process then; you have to have already done the work.

So just focus on building a relationship between them and the rest of your team. Let them know that the door is always open, and that you’d love to work together some day. This approach is extremely liberating because it aligns your interests with theirs. It lets everyone be their authentic selves, without any of the awkward or superficial pressure that so often creeps into recruiting.⁵ And it grows the relationship beyond just recruiting: even if it doesn’t end up being the right fit, you’re now allies and can help each other in any of many ways down the road. But it more often will end up being the right fit, because by genuinely caring about what’s best for the candidate, you naturally nudge your startup towards being the answer.

03 Nov 2020

Piranesi | Susanna Clarke

Some books are so refined to their very essence that I just can’t bear to tarnish their words by describing them with my own. Piranesi is one such book. So instead, I will simply say that this is the best book I have read this year.

I highly recommend you read it, and that you go in knowing as little about it as you possibly can. Don’t read the reviews; don’t even read the book jacket. Just start, and enjoy discovering its secrets first hand.

You will be in awe of what you find.

27 Sep 2020

Thoughts on Dune

I first read Frank Herbert’s Dune in early high school (on the temperate Orcas Island, quite the opposite of Arrakis!), and while I loved the story I was a bit too young to appreciate all of its nuances. So I’d always intended to reread it, and when I first heard that Denis Villeneuve was making it into a film, I resolved to do so prior to its December 2020 release. I finally dove in upon seeing the film’s excellent trailer, and finished in September with plenty of time to spare… only for the film’s release to get pushed out to October 2021 due to the pandemic. D’oh!

Well, at least I’ll have time to read the next five novels before the film finally comes out. Just kidding; I probably won’t do that. But I did really enjoy rereading this one.

Some thoughts (🐉 Spoiler Warning!! 🐉):

• I now better appreciate Paul’s Messiah arc, how his ascendancy distances him from his mother Jessica, and how it transforms him from an earnest, dutiful youth into a reserved, calculating adult. Paul ends up carrying with him millions of lives previously lived, and seeing myriad future paths that he must navigate between. He experiences an inexorable gravitational pull into a dark future that he strains against, yet seems powerless to avoid. He shoulders a tremendous burden. Who Paul becomes by the end of the novel didn’t match my teenage self’s expectations: that our earnest hero would gain incredible powers, but retain the same innocent identity he embodies in the beginning. The cognitive dissonance I felt as a kid — between who I expected Paul to be and who he’d actually become — makes much more sense now.
• I didn’t get that there was a war between Humans and AI’s (the Butlerian Jihad) in my first reading, that the AI’s lost, and that computers have been banned. Instead of computers, we now have highly specialized, elite humans whose abilities are elevated by psychoactive drugs, carefully planned breeding, and all sorts of tricks that don’t leverage silicon and 1’s and 0’s. This is especially interesting to read today, when both science fiction and the tech industry are increasingly enamored with AI. It is also interesting to me that it is never explained just how computers have been fully eradicated. The universe is vast and infinite — are there really no computers? Dune is a world of plans within plans within plans, and feints within feints within feints. Surely someone has has secreted some computers away and wields them to their advantage? We never see hints of this, though, and the extinction of the computer is taken as absolute. (Which stands in interesting contrast to atomic weaponry — banned, but still stockpiled by the Great Houses.)
• It was interesting to reread this with an eye towards Politics as a tool/technology, especially as deployed by the Bene Gesserit.
• The ending felt strangely abrupt: Jessica all but disappears, which I found jarring considering how prominent and compelling she was in Part 1. Paul’s ascendancy to the throne almost ends up feeling like an afterthought, and his knife fight with Feyd Rautha like something Herbert put in out of obligation (climax: check!) rather than authentic storytelling. Why does it really even need to happen? We don’t get resolution to the open questions of the Jihad, what it means for Paul to become Emperor, and for galactic power structure to be upended when the Space Guild is cut off at the knees. I guess this really isn’t an ending to the story of Dune, though. It’s just where this first book happens to end. So perhaps I should just be grateful it’s conclusive enough that I don’t feel I have to read the next one.
• I enjoyed the world building and thrill of discovery just as much this time around. That first moment when we discover one can ride a Sandworm… I can’t wait to see that in the film!
• I now have a better appreciation for what melange is; as Jon Michaud aptly put it in the article Dune Endures for The New Yorker: “Imagine a substance with the combined worldwide value of cocaine and petroleum and you will have some idea of the power of melange.” Woah.
• I was worried that rereading this book in 2020 would leave me cringing at antiquated sensibilities reflecting the period it was published in. I wouldn’t have faulted the book for it, but I wouldn’t have enjoyed it. Thankfully, I was pleasantly surprised that this was not the case; Herbert is pretty progressive in this respect relative to other science fiction from the time.
• Jessica is a very authentic character and the one I most identify with. It’s too bad that her presence diminishes as Paul’s powers grow, although this does serve to enhance the sense of the isolation he experiences, and the magnitude of the burdens he shoulders.
• Having just read and seen way more stuff heading into this rereading, it’s fascinating to revisit Dune and see how many future works it must have influenced: Star Wars (Tatooine is a desert planet; there is also an evil emperor; the Jedi <> Bene Gesserit are similar mystic organizations…), Game of Thrones (I am curious if GRRM was directly or only indirectly influenced by Herbert, but the political chess that is played in Dune seems like it must have had at least some influence….) , The Incal (I intend to watch Jodorowsky’s Dune for more of the backstory here), Miyazaki’s Nausicaä of the Valley of the Wind (the ecological aspects of Dune feature prominently)…
• I was surprised how rapidly the third-person omniscience switches between characters (often times across adjacent sentences!), but it worked well, since so much of the story is dedicated to characters outthinking each other and it is fun to get such a tight feedback loop.
• It is cool how Dune sits at the intersection of science fiction, fantasy, the classics, and just timeless myth; in that sense it’s actually fairly genreless.
• The spice must flow! Spiced drinks while reading this book are highly recommended!

19 Aug 2020

A Gentleman in Moscow | Amore Towles

In Amore Towle’s A Gentleman In Moscow, Count Alexander Ilyich Rostov (“recipient of the Order of Saint Andrew, member of the Jockey Club, Master of the Hunt”!), and self-proclaimed gentleman without an occupation, is placed under permanent house arrest in the Hotel Metropol for the crime of being a member of the Leisure Class in a post-Revolution Bolshevik Russia.

Confronted with a lifetime of confinement, Count Rostov might just be the perfect companion for the covid19, shelter-in-place circumstances we all suddenly find ourselves in. For when the Count’s new reality is abruptly thrust upon him, he adopts as his mantra that “if a man does not master his circumstances, he is bound to be mastered by them”. And so as we all settle into our own new normal, it is with satisfying release that we can look to the Count for guidance on how we might set about mastering it:

Like Robinson Crusoe stranded on the Isle of Despair, the Count would maintain his resolve by committing to the business of practicalities. Having dispensed with dreams of quick discovery, the world’s Crusoes seek shelter and a source of fresh water; they teach themselves to make fire from flint; they study their island’s topography, its climate, its flora and fauna, all the while keeping their eyes trained for sails on the horizon and footprints in the sand.

Initially, these practicalities manifest in the form of little luxuries, like procuring four bars of the Count’s favorite soap and arranging for the delivery of “a light blue box with a single mille-feuille” from Fillipov’s, the Count’s favorite bakery. The first half of the book or so is dedicated to the Count reestablishing the trappings of his Leisure life within the confines of the Metropol hotel, and I think the sheltered-in-place reader could certainly luxuriate in all these small delights and even have fun adopting them at home: finding the perfect wine to pair with some homemade Latvian Stew (a dish that features prominently in a pivotal scene at the hotel’s world-renowned restaurant, the Boyarsky); making the perfect cup of coffee (“The secret is in the grinding — not a minute before you brew.”); and arranging our home furnishings until they are “just so”, as the Count loves to exclaim.

For whatever reason, though, despite being so timely, this didn’t work for me. I slowly and idly read the first half of this book, often putting it down for many weeks. The Count ensures his days are full of delights, but his life is ultimately empty of any purpose, and so too was my reading. I just couldn’t find any point to all the idling. Your experience may differ, depending upon the headspace you are in.

If not for having promised my grandmother that I would read it, I might have abandoned. I am so glad I didn’t. I won’t spoil the plot, but about halfway through the book, something very unexpected and wonderful finds its way into the Count’s life, and imbues him with perhaps the purest purpose of all: caring for others. From this seminal turning point onwards, the Count steadily creates something much richer and more meaningful in his life than any of the conveniences he/we indulged in earlier: crafting lasting friendships and family relationships that are brimming with purpose.

After taking so long to get on a roll reading this book, I find I’m now a little sad that it’s over, because I’ll miss the Count’s cheery disposition and I feel a bit like I’m saying goodbye to an old friend. But even so, I will hold the Count’s lasting values close as we continue into our covid unknown: to give myself permission to be happy (in the large things and in the little things), and to remember that above all, even in these remote times, it is our friends and family that matter most.

Just so.

16 Jun 2020

The Rider | Tim Krabbe

I discovered this (apparently cult-classic, published in 1978) short novel when Simon Mottram, the founder of Rapha, kept citing it in an interview as the kernel of inspiration for Rapha’s brand and ethos. He spoke of The Rider so matter of factly, like it was just a part of the air that we cyclists breathe. So I looked it up on the spot, thinking I’d just add it to my queue to read later. But after reading the opening passage, I was hooked and read the entire thing straight through:

Meyruies, Lozere, June 26, 1977. Hot and overcast. I take my gear out of the
car and put my bike together. Tourists and locals are watching from sidewalk cafes. Non-racers. The emptiness of those lives shocks me.

What a way to open! This dry, blunt humor is both deadly serious and yet somehow self-abasing all at once, and it immediately sucked me in. I was compelled by how unapologetically author Tim Krabbe (also our main character) distills his devotion to the sport of cycling.

In The Rider, we don’t get chapters, we get kilometer markers, as our author and titular rider Tim Krabbe marks his progress through the road race he is recounting: the Tour de Mont Aigoual, his 309th race, this one being 134 kilometers, four cols, and four and a half hours long, working its way up and over Mont Aigoual in the South of France, the “sweetest, toughest race of the season”.

The Tour de Mont Aigoual is the sweetest, toughest race of the season.

What follows, then, is the interior monologue of the rider: what is happening in the race, right when it happens, from Krabbe’s perspective. This of course includes the events of the race: the “continuously shifting braid of the peloton”; breakaways forming and then getting caught; a break finally sticking; tactics on the climbs and crashes on the descents; the changing weather; rivals puncturing at the worst possible moment; the sprint into the finish… the ebb and flow is absolutely engrossing, at least to this avid cyclist, and I was compulsively turning the pages and staying up past my bedtime to see what happens next. Krabbe in the lead; Krabbe gets caught… oh no, the Cycles Goff rider has gained a many-minute advantage! Who is that rider anyways?

It’s possible this would all be excruciatingly boring to the non-cyclist, but I don’t think so, because ultimately it is something much more universal, the struggle against self, that forms the bedrock of The Rider. As Krabbe himself put it, “You don’t have to like whaling to like Moby Dick. And you don’t have to like cycling to like my book. Of course, it helps.”

Cyclist or not, we get to traverse the raw and ever-changing interior mental and emotional landscape of the rider, as mercurial as the parcours of the race, darting from supreme confidence to crippling fear; from enjoying the pleasure of fellow riders’ company to despising their presence; from soaring hopefulness to utter despair… through all this, Krabbe captures the essence of cycling. People ask me why I ride, and I will probably always be chasing the evolving answer, but at the very least I can now simply point them to The Rider. It’s all here.

In that same interview, Krabbe asserts that “Once you start explaining things you degrade them. They’re only what they are in themselves.” And so to that end, I’ll simply say that I cycle because I can, and I’ll conclude by selecting some passages that really resonated with my own experiences in cycling:

‘Good legs?’ the guy beside me asks. ‘We’ll see. And you?’

This nervous energy is so familiar; it can be found on every start line of every race everywhere. It’s so pointless, this back and forth, but we can’t help ourselves! By the time we’re lining up at the start, everyone is what they are. You’ve either trained or you haven’t; you either feel good or you don’t. I hate this banter, because it just adds to the edge and anticipation I’m already feeling. Leave me be! Don’t impose your insecurities on me! Don’t invoke mine!

The first climb won’t be for another thirty kilometers, at Les Vignes. I’m longing for it, just like when I’m doing it I’ll long for it to be over.

So true. This might be the central paradox of climbing. It can be so excruciating — your heart rate and breathing on the limit; your legs screaming; stinging sweat rolling into your eyes; the tendons in your forearms aching as you desperately tug on the bars; the tarmac seemingly touching your nose as you round a really steep ramp and head into the next switchback… I daydream about this peak experience, yearn for it, and then at some point will become desperate for it to be over. It’s the arc that matters; you need the anticipation to prepare for the suffering, and you need the suffering to enjoy the triumph of completion.

The riders had little opportunity to admire the breathtaking landscape.

This is always a source of guilt for me, especially on my “adventure” rides where I’m intentionally seeking out new routes and scenery instead of just trying to hammer out a solid training ride. Shouldn’t I be absorbing the scenery more? Shouldn’t I stop to take more photos?

The truth, though, is that flying past that breathtaking scenery enhances it in its own way. The oxygen debt and endorphins amplify the landscape’s beauty; whipping down Page Mill Road such that I can only safely cast a quick, sideways glance out over Silicon Valley only serves to make the view that much rarer and more exquisite; the sound and feeling of the wind rushing over me pairs with the visual input in a way that makes it more striking… there have been times when I have stopped to take a picture only to find the view somehow diminished… there is magic in the motion, turning a meadow of tall, dead, yellow grass into a beautiful tapestry whirring by.

Keep the steer steady, going slow here. The way I see it, your handlebars move forward and you just have to make sure you don’t let go. You need strong arms for that. I view my wrists, stretched out in front of me to the bars, straight as ramrods. They’ve become so tanned, almost black in the wrinkles. The little hairs lie next to each other in wet rows, pointing away from me. I find my wrists incredibly beautiful. I climb.

I find this to be so funny. Cyclists can be such vain creatures. And while I can’t say I’ve ever admired my own wrists, I must admit to similar thoughts: looking down as I pedal an even cadence and marveling at how strong my legs look. Or maybe cursing how weak they look. It just depends upon how I’m feeling on the climb. I’ve even had both thoughts on the very same climb…

Cycling is in many ways the pursuit of perfection, and since such a huge component of this perfection stems from the rider’s own physique, it’s natural and almost impossible not to reflect on our own body. It’s weird to acknowledge it out loud, but doing so is a way of constantly measuring and marking our tangible progress.

A hard stretch of hill. I’m not going to shift down, though, I come up off the
saddle, I’m pushing it. One more kilometer to climb. It’s so incredibly
pitiful that I ever wanted to do this, but now I’m stuck with it.

The essence of climbing. It’s so true — that eager excitement for a big climb, and then I settle into it, and the agony starts, but I bear it, and carry on, and then it’s too much, and my power drops, but now I’m committed. I’m closer to the top than the bottom. Turning around would be defeat. The self-loathing, to want to do this, but to then have to suffer so when I do. To have to slowly wind my way up. Ah, to climb.

When I withdrew to Anduze in 1973 for my first period of cyclo-literary
hermitry, I believed that, while cycling, I would come up with thoughts and
ideas for the stories I’d be writing the rest of the time. Fat chance. The
rest of my time I spent jotting in my cycling logbook and keeping statistics
on my distances and times, and while cycling I thought of nothing at all.

I wrestle with the exact same dilemma. You’d think that all the time on the bike is “down time” when you can constructively and actively think about your brain work, but you can’t, really. A hard ride is too demanding and a recreational ride too liberating to productively “work the problem” while on your bike. And once you become committed to cycling, it somehow manages to start filling up more and more of your life while you’re off your bike too: for Krabbe, jotting in his logbook; for the modern-day rider (me!), scrutinizing Strava. And reading about cycling. And planning my next ride. And, and, and…

On a bike your consciousness is small. The harder you work, the smaller it gets.

This underscores the therapeutic aspect of cycling and how it can be a form of meditation. I experience this shrinking of consciousness when riding. The riding demands being present, and especially as it gets harder, it can invoke the coveted and elusive state of flow. My world becomes the immediate sphere around my bike, and my purpose becomes the road before me. There is something very pure and gratifying in this.

I think this ties into why cycling has become so essential to my personal wellbeing. It’s a conduit for processing who I am right now. If I’m feeling happy, I can celebrate and amplify that on a care-free ride. If I’m feeling sad, I can reflect in quiet solitude. If I’m confused about why I’m feeling a certain way, I can do a long, slow endurance ride and just keep turning things over and over until the answer falls out. If I’m nervous about something coming up in the rest of my life, or if I’m angry, or if I’m frustrated, I can just go wring myself out on the climbs. Climbing can solve just about anything for me.

When I get cut off from cycling for whatever reason (normally because life gets busy), I get cut off from this open dialogue with myself. My wellbeing suffers.

Sometimes I can steer conscious thought on a ride, but mostly I have really dumb and small thoughts. Or hyper-focused, micro-thoughts, thoughts like: I should shift. I should shift back. I’m thirsty. This climb is going great. Sometimes I strive to empty my mind and experience no thought: if something is bothering me and I can’t even escape it out on my ride, then I’m really in trouble. Mind control. Perfect quiescence. Protect my personal sovereignty.

I rarely have intricate thoughts while riding, but stuff does seem to sift out over the course of a ride and by the time I finish I’ve at least prepared the canvas, even if I haven’t painted anything.

I try to return from a ride a better person than when I set out.

Four more kilometers uphill. I put my hand in my back pocket, pull out a fig. A drop of sweat on the inside of Barthélemy’s glasses magnifies this action. The firm ripple of sinew with which that Krabbé lifts a fig, like it was nothing!

This is hilarious, but gets at something deeper. How cycling on our limit can amplify our self-confidence and self-pleasure. It’s the little things.

Bicycle racing is a hard sport. A rider’s body has to ripen; it’s also a mature sport. The average winner of the Tour de France is twenty-nine years old. You do have the occasional prodigy, but those who mean him well keep him from exhibiting it. In 1977, the nineteen-year-old Italian Saronni was one of those. He skipped over all kinds of phases and was right away one of the so-many best riders in the world. Publicity! His managers wanted him to ride the Giro d’Italia. Saronni himself thought that was a wonderful idea. But, shortly before the race, he broke his collarbone. ‘The best thing that happened to Saronni in 1977,’ Merckx said later, ‘was that he broke his collarbone.’

The Rider seamlessly weaves fiction, semi-fiction, non-fiction and history all throughout. And one more bit of history, exquisitely rendered, that I can’t leave out:

Maertens and De Vlaeminck were bitter rivals. ‘De Vlaeminck is the one who let them go,’ Maertens figured quite rightly. ‘So it’s up to him to bridge the gap.’ He waited. The gap grew and grew. ‘He wants to win, so let him bridge the gap,’ thought Maertens. ‘He wants to win, so let him bridge the gap,’ thought De Vlaeminck. Both of them knew that the one who finally bridged the gap would use up energy to his rival’s benefit. What mattered now was: staying patient. Both riders stayed patient: bravo. The winner of the 1976 Tour of Flanders was Walter Planckaert.

Too good.

A disturbing thought: I’m being followed by people who are gliding along warm and motionless, and who may actually be bored to tears.

Krabbe is referring to the coaches and support staff in the “team” cars here, who follow along behind the racers. This contrast underscores the heightened and amplified experience that the physical strain of cycling affords us. People often ask: “How do you ride for so long; isn’t it boring?”

Well, not when it feels so agonizingly great and you are doing everything you can just to sustain it! I think this is why watching road cycling is so much more interesting to cyclists: we can imagine what the rider might be feeling, thinking… I admire non-cyclists who enjoy watching cycling because I think it speaks to a certain degree of empathy. They identify with the rider even though they are not one, and they imagine what the rider is going through even though they have not gone through it themself.

A cow. It’s not watching.

Krabbe’s remark as he passes the only potential spectator in sight. This is so funny to me (having passed by many a disinterested cow up in Petaluma) and highlights how pointless it all is. It’s simultaneously the most and least important thing in the world, racing bikes….

I’m not having any trouble with these curves, I’m much too tired now to worry about matters of life and death. This is about something completely different: about me winning this race.

I descend so much better when I’m able to just let go. Ironically, I find it’s safest when I’m not worrying about safety. When I stop worrying, I start flowing smoothly through the bends, in control, and get down in no time.

In interviews with riders that I’ve read and in conversations I’ve had with them, the same thing always comes up: the best part was the suffering.

The suffering provides the meaning. The suffering empowers me to finish the ride with a bit more than I started with. The suffering is what brings the personal fulfillment; the agency. The suffering is the necessary contrast, the counterbalance that makes the subsequent relaxing that much sweeter.

And then you’re at the summit. You look out over the land; you drink a bit; a ruddy sense of well-being courses through your whole body, and a great desire wells up in you to climb this mountain again some day.

Onward.

18 Jun 2019

eBooks vs. Paper Books

I’ve loved reading ever since I was a kid. But as I discovered computer programming in college and startups right after graduating, I started reading less and less. After selling my first startup and seemingly exhaling for the first time in years, the realization that I basically didn’t read any more hit me hard. So I resolved to start reading again, with the initial goal of one book per month.

In pursuit of this goal, I switched to eBooks in July 2013. I love paper books and independent bookstores, but the practical advantages offered by eBooks became too great to ignore. Being intentional about this decision and the role that my Kindle, iPad, iPhone, and even paper books play in my reading life has helped me to maximize the amount I read overall.

eBooks are portable.
I used to deliberate over lugging a single novel with me each time I headed out the door, but now I can just slip my Kindle in my jeans’ backpocket and bring my entire library with me. This means I always have something appealing to read: if I’m not in the mood for whatever I’m currently reading, I can easily switch to something else. And, because eBooks don’t take up physical space at home, purchasing a book is a lower stakes decision. eBooks enable me to own more books and to keep them with me at all times, both of which facilitate reading more.

Reading ergonomics are better than paper books.
Kindle provides better reading ergonomics than a paper book offers. This starts with the weight. A Kindle weighs the same amount no matter how long the book I’m reading is, so it’s overall more comfortable in my hands.

And because it’s rigid and always perfectly lit, it’s well-suited to more reading positions. I find that in long reading sessions I often want to change positions. I might simply want to shift my weight in the chair; I might want to lie down and hold the book over my head; I might want to pace around. All of this is easy to do with my Kindle, whereas paper books always burdened me with the minor but constant concern that my thumb would slip, the pages would fly by, and I’d lose my spot.

Being able to comfortably read in any scenario enables me to read more.

I can acquire eBooks instantaneously.
This often isn’t important to me, but it sure is nice in a pinch. Whether I’ve just finished the first book in a trilogy and am so sucked in I just want to immediately start the sequel and stay up all night reading it, or take off on vacation only to discover that I hate the book I brought with me, I can easily acquire another book under any circumstances. This creates more reading opportunities, which again helps me read more.

Highlighting and note taking is better on an eReader.
I always felt guilty annotating a physical book because it felt like I was defacing it. But even if I overcame the feeling, there was always the downside that I might run out of room in the margins. My eBook notes are still inline, but they can be as long as I like. They’re also preserved forever. I have physical books that I rigorously annotated in high school and college, but no idea where they are. And for those that I haven’t lost, at some point the pages will rot and the ink will fade. Tapping notes on a Kindle can sometimes feel more painful than writing in the margins of a physical book, but I think posterity and the leverage of being able to search my notes and easily review my highlights outweighs this.

eBook software provides leverage.
I can search an eBook for any term I like; I can view a list of my notes and get linked right to the page I took them on; I never need to dog-ear a page or use a bookmark to keep my spot. I can also easily look up the definition of a word. I often glossed over words I didn’t know when reading paper books because there was no way I was going to lug a dictionary around with me in addition to the book I was already reading. Now I can just look up the word inline, get the formal definition, and move on. And, Kindle’s software remembers the words I’ve looked up so that I can easily review them for retention.

eBooks offer practical advantages.
Portability, accessibility, reading ergonomics, and the leverage of software sold me on eBooks. But given I was switching, which device was the best for reading them? Though I started out reading exclusively on a Kindle Paperwhite, I now think that my iPad and iPhone also have their merits. I read across all three, picking the right tool for the job.

Kindle
The biggest advantage to Kindle (I recommend the PaperWhite for the sweet spot of functionality and price, but the hardware is so mature at this point that there really isn’t a bad option) is that it’s the closest you can get to the experience of reading a physical book. An eInk display is unlike an LCD: it isn’t backlit and it has a physicality that makes the experience extremely close to that of looking at a piece of paper, especially under direct sunlight. This allows for a natural reading experience authentic to that of a physical book. It also means it’s easy on the eyes. Because the screen is front-lit, you don’t have to worry about blue light beaming into your eyes before bed.

Another advantage is that Kindle is a dedicated reading device. There are no other distractions at my fingertips. I won’t hit a difficult sentence in my book and recoil to the guilty comfort of Twitter. I won’t be interrupted by an inbound notification sliding down from the top of my screen and be oh so tempted to tap it, just for a second. The only activity available is reading.

The form factor is also optimal for reading: the screen is big enough that it can fit a full page of content, but the entire device is small, thin, and light enough that it’s comfortable to hold for extended periods.

Above all, I find that I can get in the zone the best on my Kindle – even better than a physical book, due to the aforementioned reading ergonomics.

Kindle’s eInk does come with some downsides though. It can only display black, white, and shades of grey, so it’s not great for visual books or textbooks with lots of diagrams. eInk also has a pretty slow refresh rate, so turning the page, highlighting text, and taking notes can be painfully slow. When reading fiction, I don’t perform these tasks as often and so I find the downsides to be tolerable and outweighed by the above benefits. But I do them all the time when reading nonfiction and technical reference material, and so for that I turn to my iPad.

iPad
My iPad Pro’s screen offers its own unique reading experience. The super retina display is fabulous and there is something luxuriously gratifying about rendering a book edge-to-edge on that magical piece of glass. Though I do feel less like I’m looking at a piece of paper and more like I’m looking at a screen, Apple’s True Tone technology (which adjusts the color temperature of the display to the ambient lighting conditions) ameliorates this quite a bit. And the screen can fit a lot of content, so I can enjoy a full page of text book all at once.

Most importantly, though, the screen is fast. Highlighting, page turning, taking notes, and looking up definitions of words is the instantaneous experience we’ve come to expect from our devices. I tend to perform these tasks a lot when reading nonfiction and textbooks (especially seeking back and forth, as I’ll often want to refer to something on an earlier page), and so my iPad is the weapon of choice for that kind of material.

Because the iPad Pro is larger, though, it can be tiresome to hold for longer reading periods. And, of course, it’s easy to get distracted from reading by all the other things iPad can do.

iPhone
Lastly, there’s the iPhone. The biggest advantage to reading on my iPhone is just that it’s always with me. Even if I only have a few minutes of downtime, I can use them to read a book instead of mindlessly triaging email. I also find it to be very comfortable. Since the entire device fits in the palm of my hand, it’s very easy to grip, and since the screen is small, I don’t have to move my eyeballs very much, especially if I turn on infinite scroll and just lightly scroll as I read.

The Right Tool for the Job
Leveraging all three of these devices provides the most versatility for different reading situations, which, again, increases the overall amount of time I can spend reading.

Physical Books
Whither physical books? There’s still a solid place for paper books in my life. Literally, my bookshelf. I think the biggest thing I gave up by switching to eBooks is having a warm, inviting collection of books at home. After the kitchen, the bookshelf is the heart of the house: when friends come over, it’s a conversation starter. If I want or need some inspiration, my bookshelf is the place I look. If I’m going to settle into some creative work, I want my bookshelf to be in sight. You know that feeling when you walk into a brightly lit, lovingly curated bookstore? That’s what I give up with my massive eBook library. But it occurred to me I don’t have to. For my favorite books, I can just buy a physical copy too! And since only my favorite books make the cut, I can indulge in always buying the nice, high quality print version. Less clutter and more enjoyment!

A Reading Recipe
Thinking intentionally about how I read has removed barriers to entry and reading friction. It’s hard enough deciding what to read; after deciding that I don’t want to stall out because I can’t decide how to read it. So, distilled, the recipe is this:

• read eBooks instead of physical books for all of my regular reading
• primarily read them on Kindle, but switch to iPhone or iPad for specific cases
• buy physical copies of the books I love in order to maintain my bookshelf and enjoy all the little delights that come with having a real book

24 May 2019

Born to Run | Christopher McDougall

“And all because in January 2001 I asked my doctor this: “How come my foot hurts?” With that one question, Chris McDougall launches his obsessive journey to find a better way to run, and really, a better way to live. Born to Run readers get to run along side him and discover the extreme world of ultra-distance running, the essence of going barefoot, the culture of a remote tribe of super runners, and a cast of characters that is just absolutely obsessed with running in one way or another. Whether you are a die hard distance runner or have never laced up a pair of trainers in your life, the commitment to self-improvement, curiosity, and the personal sovereignty that comes from never settling for the status quo is invigorating. Read it for the infectious enthusiasm of those doing what they love, and a clarifying reminder of what is possible if we follow our nose and just keep keep asking why.

24 Mar 2019

Blood Meridian | Cormac McCarthy

I rarely abandon books, and even more rarely after already reading over halfway through, but I abandoned Blood Meridian with about 100 pages to go. The story is bleak and each reading session issued blunt trauma. Were I discovering some deeper meaning or following an interesting character arc or holding out for some narrative conclusion, I could push through the unpleasant atrocities described within and read to the end. But reading this book is to be an outsider denied entry: denied entry into any of the characters’ thoughts or interior. What motivates The Kid? Who is The Reverend, really? What is the point of all this?

I read and deeply appreciated McCarthy’s The Road, and while that book is also very dark, the key difference is it provides something (very significant!) to hope for. There’s a reason to keep reading. There are nuanced characters to cherish and savor and weigh. I didn’t find any of this in Blood Meridian, so I decided to abandon it and the nihilism it smothered me with.

21 Oct 2016

Becoming Steve Jobs | Schlender & Tetzeli

I found Becoming Steve Jobs by Schlender & Tetzeli to be a much more informative read than Isaacson’s official biography, particularly on the intersection of Jobs/Next/Pixar/Apple.

I captured some of my favorite quotes from the book and include quick thoughts on each.

Steve, during an interview he gave in the Next days:

As we talked, he drank steaming hot water from a pint beer glass. He explained that when he ran out of tea one day, it dawned on him that he liked plain old hot water, too. “It’s soothing in the very same way,” he said.

On Steve’s instinct:

Steve was innately comfortable trusting his gut; it’s a characteristic of the best entrepreneurs, a necessity for anyone who wants to make a living developing things no one has ever quite imagined before.

On his decisiveness:

Steve had a kind of hyperawareness of his surroundings that allowed him to leap at opportunities that presented themselves.

This is particularly interesting, since it proves true of acquired companies, incubators, over-funded startups, etc:

Despite what he said about wanting to repeat the experience of the Apple II and the Mac, what Steve really wanted at NeXT was the garage spirit of a startup meshed with the safety, status, and perks of the Fortune 500. It wasn’t a combination he could pull off.

On hiring the best people:

That’s because Steve was always hell-bent on hiring the very best people in the world, especially engineers. “In most businesses, the difference between average and good is at best 2 to 1,” Steve once told me. “Like, if you go to New York and you get the best cabdriver in the city, you might get there thirty percent faster than with an average taxicab driver. A 2 to 1 gain would be pretty big. In software, it’s at least 25 to 1. The difference between the average programmer and a great one is at least that. We have gone to exceptional lengths to hire the best people in the world. And when you’re in a field where the dynamic range is 25 to 1, boy, does it pay off.

On switching to management vs. remaining an individual contributor:

More important for Steve Jobs, overseeing this motley crew had turned Catmull into an expert, imaginative manager of creative people. For years Catmull found himself occasionally regretting his decision to abandon his dream of being an animator. But as he steered this odd and talented group past one crisis after another, he started treating management itself as a kind of art, and accepted that this was how he could best contribute. Later in his life, he would come to be recognized as one of the most extraordinary managers in the world; in 2014, he published a brilliant business bestseller, Creativity, Inc., about what it takes to lead a company of creative people.

Here’s to the crazy ones…

Steve, you’re not wearing shoes! Don’t you want to wear some shoes for the cover of Fortune?” Steve shrugged and said, “Sure, fine.” He ran upstairs, grabbed a pair of sneakers, and came back wearing them—with the laces left untied.

On becoming a billionaire after Pixar IPO’d:

Catmull saw Steve pick up the phone in an office to the side. “Hello, Larry?” Steve said into the handset, once his pal Ellison was on the line. “I made it.” Steve, who owned 80 percent of the company, was a billionaire.

All of the raw technology paid off when it became the foundation for OSX and iOS when Next was acquired and Steve returned to Apple:

The original dream—that NeXT would create the world’s next great computer—was over. “We got lost in the technology,” Steve would later tell me.

Even Steve wrestled with existential questions and uncertainty:

But that didn’t mean he himself was ready to take on the job of running Apple. According to his wife, Laurene, he was still torn about whether to go back. The two of them debated the matter endlessly. […] But did he really want to try to ride to the rescue of Apple when it hardly resembled the company he had tried to build? Was he even convinced it had the people and resources to become competitive? Did he want to work that hard, now that he had a young family? Did he want to risk what was left of his reputation by tilting at windmills? These questions were all on his mind. He had to become convinced that enough of the “true” Apple remained before he would ever consider taking ultimate responsibility for it. Steve didn’t know it at the time, but his indecisiveness was actually a kind of breakthrough. Steve was developing a more nuanced, measured approach to decision making. Steve had grown more comfortable with waiting—not always patiently—to see what developed, rather than jumping impulsively into some new venture where he thought he could once again astound the world. When he needed to—as when the opportunity arose to sell NeXT to Apple—he could strike quickly. But from now on he would act with a piquant combination of quick, committed actions and careful deliberation.

07 Nov 2015

Shadow and Claw | Gene Wolfe

Shadow and Claw made for a very rich and unique reading experience — one that was simultaneously challenging and enthralling. Set in an antiquated future, where the sun is dying and mankind has peaked, Severian — exiled member of the Torturer’s Guild — begins his account of leaving the citadel he’s always known for the greater world beyond.

The world he explores and recounts to the reader is rich and fascinating, but reluctant to give up its secrets. Language plays a very strong part in this, as the book is positioned as author Gene Wolfe translating Severian’s recount. In so doing, Wolfe is translating a history from the future, so we get a mix of words that are either arcane or invented: fuligin. carnifex. hipparch. Words like these are presented in a way that I found satisfying: discovering their meaning from surrounding context is a mode of discovering the world that Severian (and therefore we) get to reside in.

A third of the way in, I realized that though the language and world is dense and intricate, the plot itself is quite simple. It unfolds as a series of anecdotes and memories which are cohesive but do not drive to any form of climax. This made for a strange feeling as I completed The Claw of the Conciliator: that I had travelled so far, but also gone nowhere. But perhaps that is the mark of just how good this book is, for Severian was likely feeling exactly the same way.

Regardless, it’s a rewarding read and would probably make for an even more rewarding reread. At the finish of Claw, half way through the tetralogy, I have a number of remaining questions (spoilers follow):

• Who sent the notules (dark, deadly bat voids that feed on living cells for energy) after Severian and Jonas?
• Why did the Autarch reveal himself to Severian, and why did Severian think so little of it?
• How is it that Severian survived the touch of the avern?

Even with my curiosity around these questions and more, I’m uncertain if I want to invest the time to read the remainder, The Sword and the Citadel, to find out. There’s a good chance my questions may simply go unaddressed, or be answered so matter of factly as to seem trivial. But that’s part of the magic of this book, and probably my key takeaway: I’d read it for the experience, the lasting imagery (the alzabo extract will be very hard to forget), and the journey — not the destination. Don’t turn the pages in a rush — you’ll only reach the end and realize the most interesting parts were along the way.

22 Jan 2014

A Feast For Crows | George R. R. Martin

Had I started reading A Feast for Crows immediately upon finishing the excellent A Storm of Swords, as I was so tempted to do, I would have been sorely disappointed in the stark contrast between these two books. Whereas A Storm of Swords is momentous and significant, Feast is meandering and chooses to focus on the insignificant. Any cursory glance at the reviews for this book will inform you that GRRM leaves his most significant characters out of this installment, choosing instead to focus on secondary characters and new ones. In and of itself, I don’t think this would be a terrible thing, but in the end they aren’t compelling enough to carry the novel.

For much of the book, it felt as though GRRM simply ran out of creative steam. The unfoldings in King’s Landing are much the same, just with different pieces in play and a focus on Cersei undoing herself. Arya’s sections are fairly monotonous and straightforward – unfortunate, because I found her sections in the previous three books to be exceptionally clever and fun. It feels like a missed opportunity too, because her time training with the assassin’s guild of The Faceless Men seems ripe for wonder; instead it bores. Samwell’s passages serve some required plot advancement as we follow him moving from the Wall to the Citadel, but that is about it.

I did enjoy following Jaime on his newfound quest for honor, and also to restore the combat skills he lost along with his swordhand in Storm. Brienne’s quest to find Lady Sansa was engaging, and I think she’s a deeper character for it, but unfortunately all those pages ultimately leave the reader with nothing to show for having read them. It was exciting to learn more about Dorne, but unfortunately those sections were plagued by too many minor characters to keep track of without great effort.

The writing was weaker too – from the prologue, I had my concerns, and though the rest of the book is not that bad, GRRM adopts certain strategies that grate by the end of the book. He punctuates almost every paragraph of dialogue with the character’s internal thoughts, like this. He also betrays the realism and attention to detail in the earlier offerings by allowing implausibly chance encounters of the story’s characters in distant lands.

Ultimately, though, the core problem is it seems that GRRM just doesn’t know where to take the story, and so he bought himself time with this book. Just as the characters wander all over a desolate Westeros without much point, so does the reader trapped in his sprawling plot. There were certainly times I enjoyed this book, but in the end, I’m left feeling a little cheated, like there wasn’t much redeeming value in return on my time investment.

The question, then, is should someone read this book? The completionist in me would advise any GoT fan to see it through, especially in the hopes that the rest of the books will be better. But standing on its own, I don’t think the tale warrants the pages and time required.