April 25, 2017

4 Lessons Learned From Jason Robins, Founder and CEO of DraftKings

Last night, District Hall was the stage for Pillar VC and's Leadership and Libations panel. Moderated by Sarah Hodges, a Partner at Pillar and Co-Founder of, District Hall welcomed DraftKings' Founder and CEO, Jason Robins, for a fireside chat. Before the event, members of Boston’s tech community and guests who were avid DraftKings users came together to network and get to know each other.

Hodges and Robins then took center stage. Hodges began asking Robins a series of questions related to DraftKings, including when he gained interest in becoming a tech entrepreneur. “I caught the bug in college,” Robins said to the capacity crowd. “It started my sophomore year and it was right in the middle of the big tech boom.”

Hodges asked a few questions regarding sports as well, including what major events Robins has attended over the years. The CEO has attended the 2015 and 2017 Super Bowls where the New England Patriots won and was in attendance for the Chicago Cubs’ historic World Series win last fall.

Robins touched upon the long-delayed merger with FanDuel and remained positive about it after the two companies took surveys about company culture. “Even though there are differences, at the core we are quite similar,” Robins told the crowd. “We’ve both been through the same experiences over the past few years. It doesn’t surprise me how similar the cultures were.”

Robins offered the other entrepreneurs in the crowd sound advice and shared a bit of his story when he founded DraftKings.

Finding Investors is Hard Work...Ditto for Fundraising
One of the most brought up topics was the company’s problem with finding the right investors for a sports-related startup. Robins found himself talking with investors who were into niche markets, such as solar power. “I thought the investing part was going to be easy,” he said with a chuckle. “I always thought investors only invested in new, fresh companies.” He advised the audience to research what kind of investors would be perfect for their business.

Previous Careers Are Always Helpful
Before forming his own company, Robins held positions at both Capital One and Waltham-based Vistaprint. Both positions involved marketing, and he revealed this ended up becoming vital to selling the idea of DraftKings to investors. For any entrepreneur with a different background than business, it’s good to keep this in mind.

Managing a Startup = Being a Father?
Robins has two young children and touched upon the stresses of fatherhood. However, he did compare it to being in a management position at a company. “If you can be patient as a dad, then you have time to run a company,” he said summing it up.

One Word of Advice: Persistence
Robins’ most vital piece of information of the night was telling the entrepreneurs and founders in the crowd to be persistent with their companies. Robins talked about his mid-year struggle with DraftKings in 2015 and how they were able to overcome it. “I try not to think so negatively,” he said starting his final answer for the night.

“Anyone who has formed a company and has said there weren’t any struggles is lying,” he said. “There will be struggles. There will be bumps in the road. And at the end of the day, you just have to work through it.”

Colin Barry is a contributor to VentureFizz. Follow him on Twitter @ColinKrash.

Images via Colin Barry.