5 Lessons CEO Jason Robins Learned In DraftKings’ First 5 Years
Pillar VC was founded on the belief that connecting visionary founders with experienced entrepreneurs leads to game-changing impact. When you’re experiencing the rollercoaster of startups, there’s a lot to be learned from people who have seen the movie play out before.
On Monday evening, Pillar Partner, Sarah Hodges, sat down with DraftKings co-founder and CEO, Jason Robins — one of Pillar’s seventeen CEO co-founders — for a candid conversation with founders and emerging leaders from across Boston. The conversation was an opportunity for Robins to share the knowledge he’s gained by founding and leading one of Boston’s highest-valued private companies. The night was filled with lessons he’s learned from challenges he’s faced at the helm of his company during the last five years.
Here are five enlightening takeaways from the conversation:
Preparation
Hodges: What did you learn during your time working at Vistaprint that prepared you for where you are now?
Robins: Even though I caught the tech bug in college, and I worked at Capital One, Vistaprint was really the first technology company I worked at, and they really pioneered early internet marketing. They were the first to figure out a lot of new measurement and testing techniques, which allowed them to do a lot of rapid testing on the web. They had an incredibly well-built out analytics department, and they had been early-on in certain marketing channels and were really doing things differently than what I had seen at Capital One.
So, I learned a lot about Internet-based analytics, user interface design, marketing, and I made a lot contacts on the technology side with a ton of great engineers there. Overall, I learned how an Internet-based company thinks. And while they were still analytics-based, similar to what I learned at Capital One, it was a bit different in the actual applications and specifics around it.
Ideas and Opportunity
Hodges: From Vistaprint to fantasy sports, what took you there? How did you have the idea for DraftKings?
Robins: I had been a fantasy sports fan for my whole life. But it was really only luck that I ended up doing something for my startup in fantasy sports. It was just a fortunate by-product.
The real draw was the idea of being an entrepreneur, especially a tech entrepreneur. Anything that I thought was a good idea, was a good opportunity, and was obviously a chance to put a great team together…anything that fit that mold, I would have been interested in. For me, it was more about finding an idea that we could really build into a big company.
If you are going to go and pour everything that you have into something, you better be going after something that is a big market and is a real opportunity.
It ended up being different from what we initially thought, but the core idea stayed the same.
Early Fundraising
Hodges: Many people know that you’ve raised hundreds of millions. What was it like when you initially went out to raise money?
Robins: This week, we are actually celebrating the five year anniversary of the launch of the company. So that first fundraise was about five years and two months ago.
The first one was just a huge struggle. I was still at my day job at Vistaprint, and we were working nights and weekends on DraftKings. Every night after work, Matt [Kalish] and I would go over to Paul’s [Liberman] house and we would work out of his spare bedroom. We’d wake up around 6 or 7 am on weekends and work on it all day. We were putting in close to 25 or 30 hours per week.
It was hard. We were working 80 hours plus per week, overall, and, more than half of that wasn’t going towards this venture. None of us came from wealthy backgrounds, and none of us could afford to fund a business without working. So we were facing this dilemma about whether we quit and go all in — which meant we’d have to dial back the amount we were contributing to get stuff done for the business — or, do we keep going at that pace.
For a while, we were hearing from folks who said they loved us and loved the idea, but that they couldn’t fund someone who hadn’t left their day job. Still to this day, I don’t know how much of that was BS and how much was real, but eventually, we raised money.
It was this terrible dilemma, and we did a lot of back and forth discussions with each other trying to decide if one of us should quit. From the moment we first set out to fundraise, it probably took six months for an investor to commit.
Once you get a good VC firm with a name though, it’s funny how some people who before were hesitant suddenly aren’t so hesitant. One of the only other funds that came in on that initial close was Boston Seed. (Nicole Stat’s here tonight.)
Luck and Hustle
Jason met Ryan Moore, the partner at Accomplice who ended up investing in DraftKings, through Alex Finkelstein, a partner at Spark Capital. Although Spark passed on DraftKings, Finkelstein had told Robins that he liked the company. Jason told the story of going back to meet with Alex just to get advice on what he should be doing differently to raise money. After giving him some suggestions, Finkelstein told Jason that he couldn’t connect him with other VCs because they would ask why Spark wasn’t doing the deal. That night, Finkelstein and Moore happened to have a meeting, during which Ryan discussed his love for fantasy sports. Alex connected Moore and Robins, and Accomplice became one of DraftKings biggest early backers.
Robins: That was a good lesson for me in many different ways. One lesson was, obviously, had to do with the process of fundraising; I’ve learned so much about it since then. But also, I learned about the idea of putting yourself out there and trying to build relationships with people.
It was just good fortune and that approach that led me to end up spending time with Alex on the same day he ended up getting a beer with Ryan. And Ryan ended up being a perfect fit as our initial investor. It was just luck and putting yourself out there that put us in a situation for something good to happen.
Learning Through Others Experiences
Hodges: As first time-founders, how did you, Matt, and Paul figure out how to navigate new territory?
Robins: Early on, we tried to surround ourselves with advisors that were smart and who had had experiences that were similar to the experiences that we thought we’d go through. We always talked about the idea that you can multiply the value of your experiences if you get really good at learning from others.
If you can take other people’s experiences and make them have the same level of value, or as close to the same level of value, as if they were your own experiences, that is a real talent and a real skill to have.
It is worth putting time into doing this because you can save yourself a lot of time and heartache by taking others experiences and getting the same value out of them as if they were your own.
Know Your Audience
Hodges: So, you were born in California, grew up in Florida, and have spent the last many years in Boston. What’s your favorite team?
Robins: Obviously, the New England Patriots.
[Thunderous applause from the sold-out crowd]
Like it? ❤ it. Share it. Below.
