4 Valuable Takeaways From the Sale of 'Barstool Sports'…

Barstool Sports is a blog I’ve been reading for the past 10 years. Founded in Boston by Dave Portnoy, a.k.a. “El Presidente,” it’s since grown into one of the most popular blogs out there, mixing just the right combination of sports and satire.

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When I read last week’s blog post announcing the sale of a majority stake, I wasn’t sure if it was true or just a hoax. Then I saw outlets like Business Insider and Fortune picking up the story, confirming that a sale had taken place. Reports claimed that the blog had received a valuation between $10 million and $15 million.

I was genuinely happy for Portnoy and the team over there, but aside from that, I realized that there were some lessons entrepreneurs could learn from this win. Here are those five valuable takeaways, along with some insight from Portnoy himself.

1. Consumers fall in love with a brand, not ‘smoke and mirrors.’

Longtime readers of Barstool Sports will all agree on one thing — the blog hasn’t always provided the best user experience. Even after a recent redesign, users still posted a lot of sarcastic comments about how bad it still was. 

Personally, I vividly recalling Portnoy once mentioning that technology wasn’t the site’s strong point, but that the brand overall had still always thrived because the user-base fell in love with its message and the people behind it.

Elaborated the founder: “Technology has always been frustrating for us. I can see a guy’s blog and know if he’s funny, but I can’t tell if that person is a good designer or coder. I stuck with what we were good at, which was creating great content. Content always outweighed our technical struggles.”

An elaborate website design, then, isn’t going to magically make a mediocre blog successful. Focus on creating an authentic brand that your audience will fall in love with and become loyal to — they will see right through any smoke and mirrors. 

2. Don’t listen to someone who says your idea will never amount to anything.

How many people do you think told Portnoy he was borderline insane to think that his blog would turn into something? I’m willing to bet that number was staggering. I’m also willing to bet that there were numerous people who continued to doubt him throughout the next ten years.

Imagine if he had listened to those doubters when the blog was first launched? What if he had said, “Yeah, you are right; it’s a long shot. I won’t even try.” 

There was plenty of doubt, even from those closest to him: “I met my wife in the early days of Barstool and she said the idea stunk,” Portnoy wrote. “She made me get a job during year two, and I quit at lunchtime on my first day. My dad said he didn’t get it, but I always knew in my heart that I was on to something. I’m not sure if I was right about that at the time, or if all entrepreneurs feel that way in the beginning. This is the only thing I’ve ever started, and I was basically ready to die to make it work.”

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In short, had he taken the advice of those that doubted him and his vision, he wouldn’t have been able to sign off on the sale announcement blog post with this:

“PS – I’m kinda rich now.”

You too can welcome constructive criticism and opinions, but never let someone flat-out tell you that your idea “will never work.”

3. Hold out for your price, and partner with those that you are 100 percent confident in.

Portnoy has been approached with offers in the past — and has declined them every time because he feared the blog’s editorial direction being changed. He held out for the right deal, and received exactly that from Peter Chernin’s Chernin Digital Group.

While he sold 51 percent of his company, he still maintains 100 percent editorial control. Combine that with a nice financial payout, and it’s the perfect deal for him. Even more important is the fact that he has complete trust in Chernin’s group to take Barstool Sports to the next level.

“Lots of people have asked me what made this the right time to take money,” Portnoy explained. “It wasn’t the timing — it was that the right investor finally revealed itself. Barstool was profitable and everybody was happy. We weren’t desperate. Chernin was the first time I felt 100 percent in my gut it was the right fit and the right partner — that’s why I did it.” 

4. Be open to change when it opens the door to something larger.

Portnoy is a diehard Boston sports fan. Yet, in what might be the most diabolical Boston super-fan move of all time, he is relocating the company, the entire team and himself to New York.

In the video that accompanied the announcement, shot in Times Square, Portnoy said, “Do I like Manhattan? No. Do I want to be in Manhattan? No . . . but it’s the right move.”

He was right: It’s a move that will ultimately play a major role in the brand’s growth. And Portnoy was open to change because it’s ultimately led to larger opportunities.

“I’m a firm believer that if you’re not growing, you’re dying,” Portnoy concluded. “We’ve been doing Barstool for 12 years. It’s a totally different landscape from when I started. We’re still young, hip and relevant, and that’s because we don’t fight change. We’re not afraid to change — we want to lead, not follow.”

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