Changing seasons

Today is the last day of September, and I'm happy and relieved to see it go. I've been holding my breath. September is a violent month.  That may seem like a ridiculous thing to say, but I think there's some truth in it.  Something about the end of the summer and the abrupt change to the fall causes some trauma.  A lot of pent-up energy on the planet.  September is hurricane season, and this one has been particularly bad. A year ago yesterday, my wife's parents were hit by a truck while crossing the street.  The accident happened at 7pm, which in September, in Boston, is dark -- a time of day when it wasn't dark just a few weeks earlier.  My mother-in-law spent 4 months in the hospital, most of that with her skull partially removed to relieve the swelling and hopefully stave off extensive` brain damage.  A year ago today we were in a state of full shell-shock. In the past year, she has had a miraculous recovery, and this month she actually went back to work.  She's driving, and taking care of herself.  If you didn't know her and didn't know about the accident, you'd never suspect anything happened.  It's amazing really.  The doctors have been in awe of the recovery. We're so thankful.  And so exhausted and traumatized from the past year.  And we've been walking on eggshells all month, feeling the season change -- the air getting crisper, the night coming earlier.  Feeling the feelings we felt last year at this time, and having this unconscious expectation of impending doom.  I'm knocking on wood as I write this, that we've made it through. It's also Yom Kippur today -- the day of atonement, the holiest day of the year, and the end of the high holidays.  A time to turn the page, look back at the last year, reflect on our actions, and look forward to the new year.  I like that.  I've always liked formal turning points; somehow they make it easier to find some clarity amidst the mess. I guess I don't really have a point to this post, except to point out the change in the air, and wish everyone the best as they navigate the coming season.


Optimizing for energy

In the world of startups and investing and ideas, things are always chaotic and fluid, and as such a key skill is to somehow cut through the noise and find focus.  That's on a micro level, like what do I do for the next five minutes, and on the macro level, like am I (or are we) heading in the right direction? This may be true in other fields, but I find it to be especially true on the investing side, where situations are undefined, and there are infinity ideas and directions to explore.  On the operating side, things are slightly more bounded, but there are always large questions about direction and focus. So I find myself spending a lot of personal time working on my own mindstate, and trying to find ways to help with this challenge.  One thing I have tried this year is to use a Volt Planner, which helps you structure goals on a weekly, monthly and yearly basis.  I have found this to be incredibly useful, and I can write more that later.  One immediate observation from using the Volt Planner is that I emerge from each session (on Monday each week) feeling a rush of energy, paired with an increased sense of focus.  It's really nice. And that energy is really the important thing.  It's the foundation for all of the moments and decisions that happen, all day every day.  The more of it you have, the better.  It's foundational. So a little more broadly, I've been thinking about how important it is to optimize for energy in life.  I think that is some combination of exercise, diet, sleep, and writing.  Maybe that's obvious, and the first three are things that anyone would tell you are good for your health.  But "health", while obviously good and positive (especially compared to major injury or illness) is a little abstract, and for me at least, a little hard to motivate around on an everyday basis.  I suspect that will change as I get older. Energy is the foundation of doing anything, and it feels like there are compounding / exponential results to having more.  I am not saying I have figured out how to really rally myself behind this idea on a consistent basis (which is why I'm writing this), but I think it's worth figuring out which activities give you more energy and which suck it away.  Worth figuring out.


Learning by doing

I had lunch yesterday with someone who has been investing in the crypto / token space recently -- having pooled together a small "fund" from friends and family.  It's a short-term vehicle (like, 6 months), and a large part of the goal is simply to become hands-on familiar / capable investing in token sales / ICOs, and dealing with issues like custody and security.  At least for the moment, there are so many odd aspects of working in this space (handling private keys, exchanging tokens on various exchanges, downloading wallet software, etc.) that actually a large part of the value that a fund manager offers is handling all of that stuff.  Over time, this will change, as infrastructure and new financial vehicles (e.g., ETFs) come to market. But for now, it's actually really complicated and hard to do this stuff, and there's no better way to learn it than by doing it. More generally, I just love the idea of learning-by-doing.  It's the best way. Right after college, when I thought I wanted to be an architect, the first thing I did was get a job with a construction company, building homes.  I spent the better part of a year shoveling gravel, jack-hammering old driveways, and sealing foundations, but I also got to do some more interesting / complicated building work over time.  My reasoning at the time was that I didn't want to be that jackass, know-it-all architect (believe me, that's often how they are perceived by builders) who didn't know how things really worked at the ground level. Same thing when I got into programming.  There are two really beautiful things about learning to code: 1) you can learn everything you need to learn at basically zero cost online, and 2) you're making as you're learning.   I think that's great as a learning mechanism, and it's also really great in terms of motivation.  Nothing like wanting to finish making something as motivation for learning how to do it! Learning-by-doing is harder to do when it comes to investing.  Because, of course, in order to invest, first and foremost you need capital.  But it doesn't need to be a lot, especially in the cryptocurrency space.  So it's possible to learn to be an early stage tech investor by actually doing it.  I think that's pretty exciting. (as always, buyer beware!)


Keeping it simple

We recently had our daughter's birthday party, and we held it in a public park near our house, where there's an old parks department building.  The sun plan was outdoors, but of course it thunderstormed and we didn't have a back-up plan.  So we called an audible and asked if we could use the back room in the parks building and they said sure. So we ended up with a bunch of kids running around a dank, old, concrete room (1950's style - mostly unchanged since then), eating pizza and cake and being entertained by a (wonderful, thank god) balloon twister, in the pouring rain.  It was dead simple, and cheap.  And the kids had a *fabulous* time.  Our daughter was thrilled; one of her friends said it was the best party ever. It just goes to show that sometimes, simple is best (or at least, can be great).


What's your medium?

Yesterday, I caught up with my old friend Gary Chou.  Gary was the first General Manager of the USV Portfolio Network (predating Brittany and Bethany), and has since been running Orbital, a community space and "studio for building networks" (which happens to be in the original Kickstarter building on the Lower East Side).  We got to talking about the different things that have been going on at Orbital and the ideas Gary is working on now. One of the things he said that really stuck w me was the question of "what medium do you want to work in"?  Like, bits & pixels (design, coding), or dollars (investing), or people (events, teaching), etc.  I had never really thought of it this way, but it does make sense to think of things in terms of the medium, or put another way, the tools and objects you have at your disposal.  Or yet another way, what is the craft you really want to hone. At USV, our primary medium is dollars, or more accurately, investments, which includes dollars but also things like deal terms, corporate structure, etc.  And it's also ideas - we need to absorb ideas from the market, develop our own ideas (conviction around investing themes) and trade in ideas (influence within companies, attention in the market, etc).  And my personal medium has always included a healthy dose of bits and atoms, as my background is as a builder, designer, and hacker. I never really understood money/investing as a medium until I joined USV, but now I see that there is real artistry to be developed here.  So much nuance involved in making situations "work out", and the tools at hand are the tools of finance, corporations, leverage, and dealmaking.  It has been really incredible to see those play out from the inside, and I feel like I have the privilege of observing masters at work. As a personal strategic question (from the perspective of someone working to develop their career path or professional identity), I find the framing of "medium" to be really clarifying and helpful.  What medium do you really want to be devoted to?  Where do you have the most leverage?  And as such, how should you be prioritizing your time, and what skills should you be focusing on developing?  Where are you dedicating to perfecting your craft, and honing your art? This is a useful frame because, at least in certain fields like startups where things are often under-determined and fluid, it can help you prioritize and focus, which is perhaps the #1 most important overall skill. So, what's your medium?  


Getting Help

I'm on vacation this week, and we have some old friends and their family staying with us.  Last night we got to talking about therapy (like psychotherapy) and how valuable it has been for me over the past few years. Maybe four years ago I started seeing a therapist on a bi-weekly basis.  There were a few specific things that were stressing me, and also a more generalized sense of anxiety that I wanted to work on.  And then, over the next few years a few specific difficult situations came up that we worked through.  My guy comes from a Zen / mindfulness background, which really works well for me. When I think about what I've been working on and dealing with over the last few years, I can point to this first step of finding a therapist (I refer to him my "shrink") as the single most important thing I've done.   It's really amazing how much just having someone there to help makes a difference -- whether there's something specific going on, or nothing at all -- having someone there to help just unlocks a lot of stuff. At around the same time, I got a new primary care doctor, and also a new accountant.  Both of whom are amazing and have helped get things in better order, in terms of health and finances. I remember thinking, back then, "wow, it's OK to get help with things".  That may be so obvious to people, but for some reason it really hit me as profound.  For the first time, I felt like I had a great team backing me up, helping me improve on all the things I wanted to improve on. There is a lot of stigma around getting help, in particular around getting psychological help.  Like, what's wrong with me that I need this, or why can't I just deal with this on my own, or with my friends, or with diet and exercise.   It took me a while to take the plunge and get help for the things I needed help with, and I got stuck on all of those questions before I did. But I can say without hesitation that getting actual dedicated help was the best thing I've ever done, and it has really unlocked a whole lot for me.  And if you think about it, it would be ridiculous to expect anyone who wants to excel at anything to do it all alone -- the Patriots don't coach themselves, and Roger Federer doesn't go it alone either.  In those cases, it's so obvious that help is good and necessary, and that's true for your mind, your health, your finances, etc. At USV, many if not most of our CEOs have an executive coach, and I can't recommend it more.  A good executive coach can play the role of therapist in a lot of ways, but a dedicated, non-work therapist is a great thing too. If it's available, and if you can find it, I'd encourage anyone out there dealing with anything hard to get help from someone good.


Getting in over your head

I was out last night with some of the little league coach dads, and we got to talking about whether it's better for our kids to be bumped up a level (but be at the lower end of skills/experience) or stay back a level and have a chance to really excel.  The consensus was that you want the kids to stretch, and learn from people who are better than them, but not to take it so far that they feel demoralized and tiny. It got me thinking back to the time in first grade where I got bumped up to the higher math group, but then couldn't hack it and got bumped back down.  I can still see the workbook where I doodled all over the pages because it was easier to do that than to engage in the work. And then I thought about the time I took intro to computer science my freshman year at Stanford (never having done any coding before) and feeling so left behind by the rockstar kids in the class, who seemed as though they'd been coding since they were six. I dropped the class.  That one really stuck with me -- I really enjoyed coding, but didn't stick with it (at that moment in time -- I came back to it later). But for years, I regretted not giving it a better shot. Then, 5-1/2 years ago, I was out to lunch with Brad Burnham from USV, intending to pitch him on funding one of our spin-out projects at OpenPlans, and he asked if I wanted to come and do some work with them.  The area of work that Brad wanted to focus on at that time (tech policy) was something I had touched on during my time at OpenPlans, but I was by no means an expert.  And stepping up into a big name VC firm was exciting but intimidating. I remember going home and weighing a bunch of options -- at that time, things were changing at OpenPlans, and there was one opportunity there, another opportunity at another tech company, and then a very unformed (and kind of terrifying) opportunity with USV.  As I thought about all of that, I remember thinking that going in the USV direction was definitely the most interesting, but it would mean getting in way over my head. I obviously decided to go that route, and it has been a steep and amazing learning curve ever since (starting with the policy work, then getting into everything we do at USV).  And I think I have learned a whole lot from people who have been doing this for decades.  I'm glad I made that decision -- and more importantly that I stuck with it, even though there have been plenty of times when I doubted whether I could do it. I think this is particularly relevant in the startup world, where things are changing constantly, and there's plenty of opportunity to step up into bigger roles as things change.  My colleague Bethany wrote about this last week -- how a startup is almost like a completely different organism every six months, with different holes to fill and different ways to contribute.  It can be scary.  I remember back at OpenPlans, when I went from managing a small product basically by myself, to inheriting a 20-person engineering team, and then 2 years later running a diverse division of the company.  The first time I had to decide someone's salary I was like, oh shit, and the first time we did a restructuring, I was like really oh shit. Going through all of this, the earlier failures that continue to haunt me (and believe me, there are others) have continued to serve a pretty good purpose: reminding me, when things get hard or intimidating, or when doubt creeps in, that I want to stand up though it and learn from the situation, rather than shrink from it. I hope we can teach our boys (and girls) to do the same.


The Next Web Amsterdam: Purpose, Mission & Strategy

Last month, I went to the (most beautiful city in the world) Amsterdam, to speak at The Next Web Conference.  I did two talks, one at a sub-event focused on tech & social issues, on the topic of Data & Power, which I will post when it comes online, and a main stage talk on the topic of Purpose, Mission & Strategy -- how to connect the three to align efforts within a company. In the talk, I take examples from throughout our portfolio of how leaders define and communicate their purpose, within their organizations and externally, and then use that to make tough strategic calls.  For example, I wrote last week about how Cloudflare is fighting hard against patent trolls, and how deciding to do that is not just a narrow corporate decision, but a tough strategic call that draws from the company's sense of purpose and mission (frankly, I explain that example much better in the post than I did in the talk). For another example, Brian Armstrong from Coinbase just posted their long-term strategy yesterday, and this another example I discuss in the talk. I've been impressed by how Coinbase's efforts are aligned internally, and by the way Brian has connected the company's purpose and the strategy. You can watch the whole video (about 25 min) here: And you can see the slides here: This was my first time giving this talk, so of course there are things I'd tune for take two.  I would in particular like to thank the awesome folks at Praytell who hosted me for a dry run of the talk and gave me great feedback and questions.  And of course I would like to thank all of the USV leaders who, over the years, have shared their stories, which were the foundation of the talk.  


A little better every day

I just got done coaching my son's baseball practice. It has been amazing to watch this group of 7 and 8 year olds improve over the course of the season - learning the fundamentals and now starting to make some pretty great plays. I had a great baseball coach as a kid.  I'll never forget the feeling of having the coach show us the right way to throw, and how weird it felt at first, and then how normal it felt eventually. He said: "practice doesn't make perfect. Perfect practice makes perfect", and that has always stuck with me. It is the idea in Angela Duckworth's book, Grit, that sustained, directed effort is the thing that gets people from good to great. Making little steps every day, targeted to improve the weaknesses you want to work on. At the USV CEO summit a few weeks ago, the CEO of a very large, successful and fast growing company said something to the effect of "we have always reminded ourselves to have a big vision, but to take small steps to get there" (I am butchering the language but you get the idea. It really struck me because it is easy to think that for companies to grow and be great and big, every improvement has to be a giant, immediate leap.  That's a hard mindset to shake, because it's just so intuitive, and there is also so much pressure to grow and succeed. But really, all you can do is focus on getting a little better every day.  And over time, each of those improvements is part of the overall improvement, which compounds as it grows. I think it can be hard to give yourself the space, and have the patience, to just focus on making small improvements every day.  But it feels to me like this is a very healthy and productive mindset if you can find it.


The new normal

The week before last, my in-laws were hit by a truck while crossing the street after dinner. The time since has been a disorienting whirlwind of sadness, fear, hope and thankfulness.  My mother-in-law suffered a very serious brain injury, and while she has cleared the first hurdle of basic survival, the outlook won't be clear for quite some time.  It's been enormously trying on the whole family, and will continue to be for a long time; maybe forever. The issue I want to reflect on here is how, in the face of previously unimaginable circumstances, we seem to have the ability to quickly reset to the new normal.  Two weeks ago it was unthinkable that this would have happened and she'd be in this condition, and now, that's just how things are -- that's where we're starting from and it's what we have to work with. I find that encouraging, and also a little bit scary.  On the one hand, it shows how adaptable humans are, how we can handle more than we might think.  On the other hand, it shows how fragile any current environment or situation can be.  I'm inspired by our ability to take things in stride, and also a little bit terrified by the reality of how quickly things can change. For instance, lots of the talk this election cycle has been drawing parallels between now and the WWII era, in particular looking at what people did or didn't do to stop the rise of Hitler.  As with Trump today, Germans of the 1930s didn't take Hitler seriously, and I'm sure couldn't believe that such a radical change in national character could happen so quickly.  Whether or not you find that comparison fair, the point is that things can change quickly (or seemingly quickly). Given that, I'm thinking about two things: First, man you gotta appreciate what you have when you have it.  Looking back at photos from two weeks ago, or thinking about the last time we saw each other a day before the accident -- that's a lifetime ago now. And it's cliche, but realizing how quickly things can change really helps you motivate to appreciate what you have.  Whether that's family, friends, democracy, or the environment (however imperfect each may be).  For the past week, every time I've been snuggled up with my kids & my wife, or enjoying a moment with a friend, or tackling an interesting work-related issue, I've been hyper aware of how awesome is to be alive and doing that. Second, maybe change isn't so scary after all.  Someone once explained this to me as pain x resistance = suffering.  We burn a lot of effort and energy worrying about what might happen and what it might mean, resisting any exposure to pain.  But this is ineffective and counterproductive, and in fact only increases our suffering.  When bad things actually do happen, we face the pain and move through it, and only then are then able to build up.  This is hard to internalize, especially with smaller things on a day-to-day basis, but I think there's something there to grab onto. To sum up, I just want to say thank you to everyone that has been supporting us through this time, and also thank you to everyone out there putting one foot in front of the other to get through every day, no matter what issues are dogging you.