5 Things I Learned From Dave Portnoy About Starting a Business

I recently sat down with Dave Portnoy and he told me absolutely everything about how Barstool came to be. He didn’t have hundreds of thousands in startup funds, a fancy degree, or a staff of people to help him—in fact, he did it all on his own, the scrappy way, with barely any money… and he shared all the details about how he got it done. Here are five things I learned from Dave about launching a grassroots business:

1. Don’t be afraid to fail.

Before Barstool, Dave tried to start a company that matched student athletes with college recruiters. “I spent two grand—at the time, a ton of money for me—developing the software. It was called Next Step Scouting,” he told me. As you can tell, Next Step Scouting didn’t exactly get off the ground; But things worked out just fine for Dave because he kept trying and didn’t turn one setback into a complete defeat.

2. Begin with your most attainable idea.

Dave had a few business ideas he was kicking around, but they were all more complicated, expensive, or had more barriers to entry than Barstool. Waiting for a big, huge, disruptive idea to come along results in… waiting. Starting with something attainable leads to… action. “I had other ideas; This is the one I landed on because I thought I could do it the easiest,” Dave said.

3. Lean on your friends, but don’t rely on them.

When Dave came up with the idea for Barstool—a flyer for guys who like sports and gambling—many friends initially seemed interested in getting involved. “I talked with my friends about starting it, and everyone was gung ho, gung ho, but when the rubber met the road, they were nowhere to be found,” he said. So, he proceeded with his idea on his own.

4. Focus on quality and exposure.

When Dave first started Barstool, it was a simple newspaper. “I used to wake up and hand the newspaper out outside subway stations,” he said. A stroke of luck came when a fan of the paper offered to help: “A guy who took it, like, routinely, was moving from Boston to New York and basically was like, I love the newspaper, if I build you a website, would you put it on the web? I was like, yeah, if you wanna do that for free, knock yourself out,” Dave said. The guy ended up being Ian White, who was the CTO for Business Insider. “I got very lucky,” Dave said.

5. Believe in your idea even if no one else does.

Dave started expanding his distribution from subway stations to bars, even though he was unsure if the idea would catch on. Because he persisted, it did; “I’d go around Boston, and every time I went in bars every week, more and more people would be, like, ‘Hey!’ waiting for us. So, I just had a gut feeling like, hey, more and more people are picking up on it,” he said. He took Ian White’s offer and put the newspaper online—literally just as a PDF at first. “When I started, if you told somebody I had a blog, they’d be like, what is that? It wasn’t a term yet,” Dave told me. In the end, the online presence helped rapidly expand the brand across college campuses.

The moment Dave knew that Barstool had finally made it came in 2010. He had pocketed enough revenue through running ads in the paper and on the blog to stage a college music tour called Stoolapalooza. “We showed up and it was like the Beatles were there. Every dorm had signs, like, ‘Viva La Stool.’ That tour was the first time we started making money. I paid [musical artist] Sam Adams, like, $20,000 for the six shows, and we probably made a couple hundred grand,” Dave said.

Want to hear more? Listen to my full interview with Dave Portnoy here.