Inside Prizeout

Prizeout CRO Richard Blankenship on Closing Big Deals, Leaving a Legacy, and Doing What You Love

"I hear so many people that on Sunday are like 'Oh god, I have to go to work tomorrow', and for me it’s like, 'Man, it’s Friday, it’s the weekend, I don’t get to go into work for two days. Nobody’s gonna be working this weekend.' I’m bummed on Friday afternoons. I get the Friday Afternoon Scaries."

Prizeout’s Chief Revenue Officer Richard Blankenship knows what makes a good investment. He’s been an entrepreneurial investor since graduating college in 2013, when he founded a real estate investment firm with childhood friend Sam Simmons. Since then, Richard has diversified his portfolio into fashion, education, and media by making key investments in CUTS Clothing, MightyKidz, and Triller. As luck would have it, he was also the first investor in Prizeout. But, Prizeout has become a bit different from his other investments. As CRO, Richard dedicates his most important asset–his time–to growing this business. I asked “RB”, as he’s affectionately known by Prizeout staffers, a few questions about how he came by Prizeout, what makes this investment different, and what gets him out of bed in the morning. 

How did you first meet [Founder and CEO] David Metz and how did that lead to your investment into Prizeout?

My first job was at Poker Central, which produces the majority of poker content available on TV, including the World Series of Poker on ESPN. I joined as a “Sales Executive” or something–and there was a Vice President of Sales, a Senior VP of Sales, EVP of Sales, and Chief of Sales all above me. So safe to say I was bottom of the totem pole. 

When I was tasked with selling sponsorships for our first event, I probably reached out to at least a thousand different brands. After hearing a whole lot of ‘no’s, I ended up closing three brands for sponsorship, including Amazon. Nobody else on the team closed any deals for this event. I kept outselling everyone and rising up the ranks and eventually I became VP of Sales, then SVP of Sales, and then finally the Chief Revenue Officer. Special shout out to my mentor, Joe Kakaty, for the incredible support and guidance throughout those years.  

I was introduced to David Metz while he was in Vegas for G2E for FleetWit (the trivia app he founded). He wanted a tour of our poker studio at the Aria to produce a Poker Trivia show. As a startup, Fleetwit needed advertising, so I proposed a deal to him where Poker Central would provide sponsorship and ad placement throughout all our content, in exchange for equity. The deal was complicated, and it took around three months to execute, but out of that David and myself developed a really strong relationship. In April 2019 he approached me with the idea for Prizeout. I immediately thought it was a no-brainer. I wired him money before we had any paperwork signed–that’s how excited I was by the idea. 

And what made you commit your time to the extent of becoming the Chief Revenue Officer?

Around the same time that I invested in Prizeout, I had just become CRO for the family office that owned Poker Central. They decided to invest in Prizeout as well, and it became clear very early on that this was going to be a big opportunity. So, we decided it was worth spending the majority of my time leading the sales org at Prizeout as the Chief Revenue Officer, and member of the Board of Directors.

You always mention that you don’t do anything that doesn’t excite you. So, what is it specifically about Prizeout that gets you out of bed in the morning?

I love building something from the ground up–it’s literally insane to bring something from an idea in someone’s brain to a functioning, thirty-person organization. Specifically, though, the number one thing that drives me is closing deals. It just gets me juiced up. I love closing big business deals and building friendships along the way. Most people get up to go to work and they’re unhappy about it, and I think one of the great things about working at Prizeout is that I wake up in the morning feeling fired up to be heading to the office. I hear so many people that on Sunday are like “Oh god, I have to go to work tomorrow”, and for me it’s the opposite, it’s like, “Man, it’s Friday, it’s the weekend, I don’t get to go into work for two days. Nobody’s going to be working this weekend.” I’m bummed on Friday afternoons. I get the Friday Afternoon Scaries…and then I usually spend most of the weekend working anyways.

What is the best piece of advice you’ve ever been given?

I have a poster in my house that says “Be Kind and Work Hard”. When I think back I don’t know if anyone has said these specific words to me but it’s been a theme throughout my career. And that’s just a great life philosophy. If you work really hard, you’re going to be successful. I’m not the sharpest tool in the shed, I’m not an Ivy League graduate with a huge brain, but I will literally outwork anybody. And the second part of that–you have to be kind. If you’re a good person, people will want to work with you, hang out with you, and do business with you.

Say that there are two deals that are exactly the same, but one of the partners is nice and you enjoy hanging out with them and the other partner isn’t–you’re going to go with the nice person. Even if the latter has a better deal, you’re probably going to partner with the former because it’s human nature to enjoy being around people who you enjoy.

Looking forward–what is your goal for the next year and then what is a more distant-future, lifetime goal?

Forbes 30 Under 30 for this year since it’s my last year to get it. (laughs) Can you tag them in this article? 

Seriously though, in terms of a lifetime goal, it’s to create a legacy. Your life will be a finite number of years but you can live forever depending on how you impact the world. I always seek to do things that will drive my legacy forward.

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