The Makings of a Serial Entrepreneur: Interview with Richard P Blankenship

Richard Blankenship

Last week we sat down for a (virtual) coffee chat with Richard Blankenship, Co-founder and Chief Revenue Officer at Prizeout, to understand his early success as an entrepreneur. The following conversation has been edited for concision and clarity:

Thanks for the time, Richard. How do you describe what you do to those who don’t know you?

Well, it’s always tricky, because I’m involved in so many different industries as an investor, a co-founder, or an advisor. The simplest answer, and probably the most truthful answer, is I’m an entrepreneur. I see problems, and I try to build businesses that solve them – that mission has launched me into industries as different as financial technology, real estate, and poker media.

Tell us a bit more about the poker industry. I’m sure many of us play, but few of us think about the industry behind it.

Definitely. I had never thought about the poker media business either. My first company was a real estate partnership with my best friend, Sam Simmons, that focused on single-family homes in the Chicago area. Our largest investor-owned Poker Central, the media rights holder for the World Series of Poker and some of the other biggest tournaments in the world. He was one of my earliest mentors as an investor, and he gave me an opportunity to join the sales team at Poker Central.

The real estate partnership was successful. We were buying a house a month, and the cash flows from the properties were lucrative, so re-focusing myself on a $52k per year sales job in an unfamiliar industry was a risky move. I believed in the founder, though, and I knew there was a lot more I could learn from him if I joined his company.

How was the transition? Did the gamble pay off?

Initially, I was in over my head. I was new to the industry and new to the structure of working in an established company. I was the most junior member of the sales team, but I knew I had the tenacity to succeed. The company’s chief sales officer, Joe Kakaty, mentored me, and I relentlessly reached out to sales prospects. In my first year with Poker Central, I pitched 1,000 companies for sponsorship.

My first big breakthrough came in 2015. Poker Central was producing the Super High Roller Bowl airing on NBCSN, and I delivered Amazon, Dollar Shave Club, and Draft Kings as sponsors. When I left the day-to-day of the business in 2019, I was Chief Revenue Officer. Today I’m still an equity partner in the company. It was quite the journey. I joined Poker Central to work closely with a mentor, and today that same mentor calls me his partner.

How have you taken those lessons into your current role at Prizeout?

As a salesperson, I’ve learned how important relationships are. The relationships I developed with executives at Amazon, Dollar Shave Club, and Draft Kings back in 2015 have generated revenue for two other companies I have helped launch since leaving day-to-day operations at Poker Central. The mantra “Your network is your net worth” really has been true for me.

As a co-founder, I trace most of my leadership qualities back to that experience at Poker Central. I’ll always remember how gracious the company’s founder and Chief Sales Officer were towards me – both with the opportunity to join the company and with their combined mentorship afterwards. As a cofounder in Prizeout, I feel an obligation to pay that forward to our junior employees. Poker Central embodied a “work hard, be kind” attitude, and I’ve carried that onwards as my own professional motto.

What’s next? Where can we find you?

I’m spending most of my time growing Prizeout and funding other entrepreneurs as an investor. Two of my favourite investments right now are CUTS, a technical menswear brand, and MightyKidz, one of the fastest-growing childcare facilities in the US. You can find me on Linkedin and on Instagram.