How Betr is Turning The Sports Betting Industry On Its Head

A sit-down with Betr’s Head of Marketing, Alex Kuwada

Author

Carlo Palomino
June 27, 2025

Welcome back to The Friday Fortune! We’re officially in the early haze of summer, too hot to think, too far from Labor Day to coast. If you’ve been dodging Slack messages while secretly planning your beach playlist, we’ve got just the productive distraction you need.

Every week, we spotlight marketing’s boldest minds, biggest brand plays, and a few brilliant ideas to steal and claim as your own. From unforgettable activations to unexpected leadership insights, we’re serving you inspo with a side of strategic genius.

Here’s what’s on deck this week:

  • A sit-down with Betr’s Head of Marketing, Alex Kuwada

  • Mars x Razer collab

  • OpenFortune works with credit unions?

📈 Marketer of the Week

If there’s anyone showing that the path to marketing leadership doesn’t have to be linear, it’s Alex Kuwada, Head of Marketing at Betr. With a career that began in conceptual math and high school teaching, Alex didn’t come up through the usual brand-building pipeline, but that’s part of what makes his perspective so sharp.

After graduating with a degree in math from Wesleyan, Alex’s first job was teaching teenagers at a boarding school, just a few years younger than he was. That experience, he explained, required balancing authority, engagement, and humor—skills that now fuel his work leading marketing in a high-stakes, high-velocity startup.

He entered the marketing world without formal business training, but leaned into his problem-solving instincts and collaborative mindset to learn fast. A six-year stint at FanDuel exposed him to nearly every part of the sports betting funnel (fantasy, sportsbook, casino) and gave him the mentorship and foundation to take a bigger swing.

That swing came in the form of Betr, the sports gaming and media company co-founded by Jake Paul. At Betr, Alex oversees everything from brand strategy to digital and content. His approach emphasizes experimentation and fun, especially in a crowded fantasy market where product differentiation takes time. Instead of relying on typical acquisition campaigns, Betr is leaning into entertainment and community-building. One campaign put three content creators in a Las Vegas casino for 48 hours, with the two who lasted longest winning tickets to the Super Bowl. “Whether or not these things will always succeed,” he noted, “the goal is learning, trial and error, and building a lot of fun along the way.”

Community, not just clicks, is core to Betr’s ethos. From Jake Paul personally FaceTiming top players to inviting partners into their half-office, half-content playground, the company’s goal is to feel more like a group chat than a gambling app. “They don’t just want to have a transactional relationship, they want to become part of the bigger ecosystem,” Alex explained.

While much of his new role stretches into brand and retention, Alex still gets his math fix through highly segmented A/B testing of bonuses and promotions, what he calls the “math problem behind generosity.” It’s a space where he’s found joy in quantifying success and optimizing value without losing sight of creativity.

Alex’s Takeaway

Trust, transparency, and calculated risk-taking anchor Alex’s leadership philosophy. He builds horizontally structured teams that welcome ideas from every corner of the business, from product, marketing, and even customer support.

To hear more about how Alex is redefining what a sports entertainment brand can be, listen to the full episode of CMO Weekly.

Crack open a handful of the week’s best marketing links—because good fortune favors the curious.

That’s a wrap for this week’s Friday fortune.

If you enjoyed the read, pass it along to your favorite marketer who could use a little extra inspo in their inbox.

Until next time, may your marketing be memorable and your cookies always be fortunate!

— The OpenFortune team