Delian is a venture capitalist based in San Francisco. Prior to joining Founders Fund, he was a Thiel Fellow working on an enterprise healthcare startup. He also spent time as the VP of Growth at Teespring, before beginning his career as an investor at Khosla Ventures. Delian is also the host of Operators, a podcast where he “interviews non-founder/VC/CEO operators that make the startup world go round,” and also writes a weekly newsletter on tech, VC, commercial space, movies, and more. He’s written some incredibly helpful essays and is a great follow on Twitter. Here’s his story!
Who are you and what are you currently working on?
My name is Delian Asparouhov and I’m a Principal at Founders Fund. Founders Fund is a venture capital firm based in San Francisco that primarily focuses on early-stage technology companies. We invest everything from seed checks of $500k all the way up to series D checks of $150 million. I primarily focus on the earlier stage companies, specifically startups within the industries of commercial space, consumer hardware, financial services, and housing.
Previously, I was a Thiel Fellow for my startup, Nightingale, that was in the enterprise healthcare space. I was then the VP of Growth at Teespring for about a year, and I’ve been investing for the past three years. I spent my first two years as an investor at Khosla Ventures, before transitioning to my current firm, Founders Fund.
What are your goals or plans for the next 5 to 10 years?
One of my major focus areas over the course of the next 5 to 10 years is to spend more and more time in the commercial space industry. I think that we’re on the precipice of an exponential growth curve in terms of the amount of commercial activity that’s going to be happening in low Earth orbit and that there’ll be a ton of interesting investment opportunities that will come up because of that. I hope to be involved in that process and help accelerate that exponential curve. So if I had a particular goal it would be to be one of the early investors in several of the companies that are at the forefront of making commerce happen in low Earth orbit.
Do you see yourself staying on the VC side or maybe moving over to the operations side?
I originally wasn’t planning to get into venture capital. I just sort of stumbled into the role, but after a few months, I realized that my personality is likely a much better fit for venture capital and investing than it is for being an actual operator. I’m super ADD, super intellectually curious, and I excel at constantly switching my focus throughout the day. All of those characteristics are huge pros and strengths as an investor, and unfortunately, most of those attributes are typically huge cons as a founder. I typically tell people to lean into what their strengths are, as opposed to trying to mitigate or shore up their weaknesses. So for me, it’s probably better to focus on my strengths, and I think my strengths so far seem to align better with being an investor. But if I were to go back operating, I think the one area that would be interesting and motivating enough would be the commercial space industry.
What opportunity most impacted where you are today?
I was originally studying Computer Science at Massachusetts Institute of Technology (MIT), which was a great experience and opportunity. The real catalyzing moment for my career, however, was actually my summer internship between my freshman and sophomore year of college. I ended up literally physically stumbling into a Square recruiter when I was at the MIT career fair my freshman year. After chatting with her and going through a few interviews, I decided to intern there for the summer. At the time, Square was an extremely fast-growing early-stage startup. They had just raised their Series B as I was interviewing with them, and during the summer I spent there they raised a $250 million Series C and closed a major corporate deal with Starbucks. I had such an awesome experience getting to join a company that was growing so fast. When I joined there were about 120 employees and by the end of the summer, there were 250-300. Over the course of about three months, I got to watch a company basically double in size.
Up until that point in time, I thought that I was going to stay in the world of academia for a long time—both of my parents are Ph.D./professor types—but that summer internship at Square really got me hooked into the world of startups. On top of that, the opportunity to be out here in San Francisco, in the midst of Silicon Valley, during that time was amazing as well. At that point, I decided that the world of academia was probably not my future and my interests shifted to the world of startups and technology.
The internship at Square actually helped me learn about the Thiel Fellowship as well. My roommate in San Francisco that summer was friends with a Thiel Fellow, and brought me to a couple of their marketing events over the summer to learn more about the program. That’s when the idea clicked that rather than finishing college or working at a startup, why don’t I drop out of school, apply for the Thiel Fellowship and work on my own startup.
Do you think that if you hadn’t been selected for the Thiel Fellowship, you still would have dropped out of college?
I definitely told myself at the time that I would find a way to drop out no matter what. I don’t know exactly what I would have done. I probably would have gone back to Square and continued to work at early-stage companies. I’m sure that I would not have returned to MIT. Maybe I would have continued working on the company and tried to raise funding outside of the Thiel Fellowship. But the Thiel Fellowship definitely made things a lot easier. I remember in late spring of 2013 I signed a lease on a place in Mountain View, CA with a couple of friends and I literally didn’t have the money to pay the first month’s rent when we were supposed to be moving in. And if not for the Thiel fellowship coming through, I’m not sure how I would have found the money.
What does growth mean to you?
The way that I’d apply that terminology to both companies and people is relatively similar: being in motion and expecting constant change. At a company, it’s looking through each part of your business equation and trying to find where you can make constant and continuous improvements. Where most of a company’s growth comes from isn’t applying the same formula over and over again, but it’s from constantly opening up new channels, trying out new products, changing things in the funnel, etc. I think that also applies to individual people as well. It seems like the people that have been the most successful in the world tend to apply that same mindset to themselves. They’re not static or fixed in terms of their skills, capabilities, and focuses. They’re constantly finding aspects of themselves to improve, and not just professionally, but personally as well. I think that the discipline of applying a growth mindset in relation to physical fitness or competitive sports is actually extremely similar to applying a growth mindset in the professional world. There’s a reason why you’ll see a lot of D1 college athletes actually end up being really great founders. It turns out that the discipline they needed in order to be a D1 athlete is relatively similar to the discipline needed to be a great founder. I think a lot of success comes down more to grit, discipline, and putting in the hours as opposed to any sort of raw IQ.
How do you think about self-care?
I actually think most of the world of self-care is a little bit BS. A different way of phrasing that thought is I actually think you’re much better off being stressed out about work than having a job that is boring and not challenging enough. I think you’re much better off actually being pushed by your job in a way that stresses you out, as opposed to not being pushed, and I tend to think that applies to most aspects of life. That means that the best way I can take care of myself is by pushing myself across all aspects of life. Whether that’s physical fitness and trying to really push myself in my workouts, or what I call “mental fitness.” It’s trying to maintain really strict sleep routines, and doing some level of meditation. The same principles apply to professional aspects of my life, by pushing myself to find the next great company, or help my portfolio companies, and other things like that.
What’s your mindset towards overcoming obstacles?
There are definitely times in my life where I’ve encountered obstacles that I haven’t been able to overcome. The most relevant was when I was running Nightingale, the company that I dropped out of school to work on. It was an enterprise healthcare company, and although we had one of the best products on the market, we weren’t particularly great at sales and distribution. Part of that came from us being a pair of MIT dropouts, as opposed to people that knew how to sell enterprise software to healthcare companies. I banged my head against the wall on that problem for multiple years without making very much progress. Each time I closed a new customer I would basically churn out another, and after two years or so of banging my head against the problem I finally said, “Hey, this is clearly an obstacle that I’m not currently able to overcome with the skill set and knowledge that I have today.”
I’ve gotten better over the years of recognizing when I’m starting to repeatedly bang my head against the wall on a problem, and have figured out how to raise my hand and start asking questions. Questions like: “Why am I banging my head against the wall with this problem? Who do I need to ask for help? What kind of skills do I need to develop so I can more successfully re-approach this problem?” To sum that up, my method is to bang my head against the problem 5-10 times and if I’m still not seeing progress, figure out why the particular obstacle is so difficult for me and what I need to learn in order to overcome it.
Has any book, podcast, or movie been particularly meaningful to you during the course of your career?
Troublemakers by Leslie Berlin. It goes through a lot of the stories of Silicon Valley that you’ve heard before, but instead focuses on the stories’ untold heroes. So rather than following Steve Jobs and Steve Wozniak, it instead follows the third co-founder of Apple, as well as people that were influential in the early days of Genentech and Atari. I really liked that book because it shows how there’s a lot of different people that are involved in the story of building a great company.
Can you talk about how you think about finding mentors or working with them?
One of the most influential parts of my career was the two years that I spent at Khosla Ventures basically being mentored by Keith Rabois on a very regular basis. I think venture capital, in particular, is very much an apprenticeship-type business where it’s really hard to start out on your own, totally from scratch, and figure out how to be great at it. I think you can really accelerate your learning curve by learning from some of the greats. That principle has been hugely influential throughout my career, to the point that the way that I categorize the different periods of my career is less so by the actual work that I did, but more so by who I was taught by and who I learned from during each period.
What piece of advice do you have for somebody building something?
Especially early in your career, I think it is best to optimize less for the exact problem that you’re working on or what the day to day might be like, and more for who you’re going to be learning from and working with. For example, when I joined Teespring, it wasn’t because I cared about selling t-shirts or consumer apparel, it was because I knew that I was going to be working with really high-quality executives and board members. The opportunity to have those learning experiences made working there worth it, even if I didn’t necessarily care that much about the particular problem or company.
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