This week on How Success Happens, I sat down with Joel Milton, co-founder of Splash Sports, a fantasy sports platform that turns everyday pools and pick’em contests into real, scalable businesses for commissioners, creators, and die-hard sports fans alike.

The platform launched in 2021 after the company acquired RunYourPool and Office Football Pool and now boasts over two million active users. Boldname investors include Major League Baseball executive Theo Epstein, New England Patriots President Jonathan Kraft, and three-time Olympian Alex Morgan.

As we near the granddaddy of “fun money” events — the Super Bowl — Splash is partnering with Cousin Sal for Sal’s Super Squares on Splash, a free-to-play game featuring $25,000 in total prizing, including $10,000 in cash for the grand-prize winner.

Listen to Joel break down the launch and growth of Splash Sports here, and read on for three business insights to help your own personal success take off in three, two, one!

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Three Key Insights

1. Make things easier for people

Joel describes Splash Sports as a platform that lets “anyone create a contest,” from a small family league to a big-time content creator or podcast trying to engage fans. But they don’t just power contests — they partner with commissioners. “We act as sort of the trusted third party to make sure entry fees are safely collected,” Joel says. “We hold onto the prize money and we pay the winners.” It creates a safe and profitable environment where some commissioners now earn six figures by running pools on Splash. By giving hosts tools to monetize and own their audience data, they’ve tapped into the “creator economy” of sports commissioners in the same way YouTube empowered video creators.​

Takeaway: Look for ways to turn something people already do informally into a trustworthy, monetizable product that solves their biggest headaches.

2. When the goalposts move, adjust your game

Splash launched in 2021 when capital was flowing and investors were chanting one mantra: “grow, don’t worry about revenue and profitability.” Joel and his team did exactly that—built product, poured into acquisition, and scaled a large, highly engaged user base—only to discover that by the time they went to raise again, investors had pivoted to asking “How much money are you making? Are you profitable yet?” Joel explains, “The goalposts moved and it made for a really challenging time to raise capital,” he says, comparing startup course-correction to steering a tanker, not a sports car. Forced to adapt, they got leaner, became more disciplined, and proved they could “grow efficiently rather than just quickly,” which ultimately made Splash “a stronger and more durable business.”​
Takeaway: Expect investor expectations and market conditions to change and build a business that can tighten up and pivot without capsizing.

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3. Don’t listen to the devil on your shoulder that wants you to try a million new things

Joel thinks one of the hardest parts of entrepreneurship is managing the “angel and devil on your shoulder” when it comes to focus versus opportunity. On one side, you see opportunity everywhere and risk falling into “shiny penny syndrome,” chasing every new idea and never moving forward; on the other, you wear “horse blinders,” execute relentlessly, and risk missing the fork in the road you should have taken. “The biggest piece of advice I can give is to make sure you’re cognizant of both challenges and try to find that balance,” he says. Joel adds that he is a proponent of a classic Lean Startup move: “get product out quickly” and let real-world user feedback, not perfectionism in a lab, guide what you build next.​
Takeaway: Set regular checkpoints where you deliberately ask, “Is it time to double down or time to explore?” and use real user feedback to make that call.

Two Great Ways to Learn More

1. Check out Splash Sports to learn about running your own contests, and find details on Sal’s Super Squares.
2. Read this article that dives into the best ways to implement Lean principles in your business and get consistent results.

One Question to Ponder

Joel talks about how childhood experiences—like watching his dad run betting pools—“planted some seeds subliminally” that didn’t show up in his career until decades later. What’s one experience from your past that might be quietly pointing you toward your next business idea, and how could you experiment with it this month? Hit reply by emailing your answer to howsuccesshappens@entrepreneur.com, and your story might be read on a future episode.

About How Success Happens

Each episode of How Success Happens shares the inspiring, entertaining, and unexpected journeys that influential leaders in business, the arts, and sports traveled on their way to becoming household names. It’s a reminder that behind every big-time career, there is a person who persisted in the face of self-doubt, failure, and anything else that got thrown in their way.