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.