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?
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.
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