Interview: Darrell Silver, Co-Founder & CEO of Thinkful

Mod Note (Andy): Darrell Silver is co-founder and CEO of Thinkful, an online school providing one-on-one education in Python and Front-end Web Development. Prior to Thinkful he was the founder of Perpetually, which was acquired in 2012 by Dell. Follow him on Twitter: @darrellsilver.

1. How did you start working at a hedge fund?

I started working at Clinton Group first as an intern, then after college. After graduation from college I had the opportunity to do some software development freelancing or go back to the fund's StatArb trading desk, which was growing really well. Choosing the hedge fund also let me move out of my parent's apartment much more quickly, so it was an easier decision that it would seem!

2. How was your experience there?

The fund and my mentors really gave me a lot of room to explore new and important areas driving our success. After only 18 months on the job I was offered the opportunity to expand the desk's strategy to several markets in Asia, and manage its trading on a day to day basis. It turned out this area of the business was unexplored (VWAP and TWAP algos were pretty new), so when I saw the opportunity I put my skills as a software engineer to work.

Within 6 months I'd built the first generation algorithms to manage all our execution trading, and after 9 months those strategies were handling about 2/3 of all our trading around the globe. That was a pretty amazing experience which helped me as a manager years later – so much of working with young talent is knowing where to point them running, then letting them do it.

3. Talk about your current company, what service you offer, how did the idea come about, and what was the key thing that triggered the full move to entrepreneurship?

I wanted growth, risk and impact. After 4.5 years in finance I learned that I loved the technology more than the finance. Not surprisingly, tech startups became alluring as a result. It took about a year to commit to leaving, and it was really scary. My first company, Perpetually, was a web archiving company we sold to a subsidiary of Dell in 2012. The experience was a taste of a life I became quickly addicted to. Moving on to Thinkful let me focus on two things I've found myself coming back to over and over: Helping young talent and building technology to solve important problems.

4. Did you have days where you doubted your idea and thought that it wouldn't work out?

Of course. Multiple times a day, and often on the same day as we'd have really good news. When you have to create your own structured day, and truly set your own priorities, life can get pretty stressful pretty quickly. But like most things, the fear is worse than the reality. I've been given enormous opportunities to succeed that frankly, I'm not sure I deserve. Being an engineer is incredibly empowering – even if my ideas don't work out I'm not worried that I'll have the freedom to find the next thing I love.

5. What tips can you give to finance guys who have the entrepreneurial itch?

Talk with more people and listen. The most important mistake I made when I left finance was let the attitude of secrecy stay with me. It took years to realize just how helpful people want to be if you're open to it.

6. Were you always an entrepreneurial type of person? What type of person is best cut out to be an entrepreneur?

I suppose I've never liked simply doing the normal thing, but that's only a small part of what it takes. Mostly, to be an entrepreneur you have to make progress each day – even if you're the only one who'll notice, even if you'll likely fail. There are a hundred tricks to keep yourself productive, but fundamentally you must push yourself to keep trying to figure out what to do next. This isn't a skill most people have naturally – it's something you practice each day.

7. You work with a partner, how much has this helped you rather than doing a project solo?

Dan keeps me honest. When you work alone you can make excuses about anything: Your time, your decisions, your hiring. It's easy to compromise when you have no one calling you out on it. At the heart of mine and Dan's relationship is the comfort for each of us to speak up quickly about what the other is doing well and what we're doing poorly.

8. What was your situation like specifically? How much risk did you undertake? Did you start the company while you still had your 'day job'? How much time did you put into your company during the first 6 months?

I didn't start Perpetually while I had a day job, but I certainly laid the groundwork. The first part of building a company is building the support network of people who will tell you you're crazy and who'll help you answer some basic questions as you grow. Once I was committed full-time I tried several ideas with a few friends before finding the opportunity for web archiving. In that first 6 months I was probably working 80 hours per week. It wasn't that I was overwhelmed, just really, really excited!

9. Pluses and minuses of being an entrepreneur?

It can have an enormous cost on your personal relationships. My partner is incredibly open to my commitment to work, but I've had to really sacrifice time with friends and other family. There's a passion and turmoil that comes with being an entrepreneur that I'm kind of addicted to, but which can be hard for others can understand.

10. What is something you wish you knew when you first got started with your current company?

Your first company doesn't have to be you alone. Don't be afraid to look for mentors in your initial job after finance, using one startup as a stepping stone to your own business.

11. What is a key to success that some people often overlook?

Distribution trumps everything. If you're not sure how people will discover your product, then you don't have a company. It's that simple.

12. What skills that you learned during your HF days do you apply to your day to day work now?

There's an art to understanding incomplete data. The basics of statistics you can learn in a MOOC, but understanding what conclusions you can draw from data, and which you can't takes years to learn. My years in finance, among learning many other things, taught me how to do this exceptionally well and quickly.

13. Anything else you'd like to add?

Many startups are hiring for "Future founders." Those who, in a few years, will want to start their own companies. Unfortunately, they don't list that as a job description, so it can be hard to find. I suggest trying. And if you want to talk to me, don't hesitate to reach out!