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This week: ​​Birches Health raises $20M to “lead fight against gambling addiction”

Birches Health raises $20M to fight gambling addiction, Underdog CEO chronicles his journey on Masters of Scale, and Bet Caddy CEO on building the “ultimate sports remote.”

Birches Health raises $20M to “lead fight against gambling addiction” 

The news: Birches Health, a national provider of gambling addiction treatment, has raised $20 million across Seed and Series A rounds to to “lead [the] fight against gambling addiction.” General Catalyst led the Seed, and AlleyCorp led the Series A, with support from Will Ventures, defy.vc, Haystack, and others. The capital will expand Birches’ provider network, grow insurance and state health partnerships, and scale infrastructure to meet rising demand. 

Zoom in: The raise comes as gambling addiction is increasingly seen as a public health crisis. An APA poll found 28% of U.S. adults gamble online daily, fueled by sportsbook ads and speculation products. Birches has built the largest U.S. network of specialized clinicians, with coverage from major insurers including United, Cigna, and Aetna. It has also established partnerships with betting companies like Jackpocket, Sleeper, Props.Cash, and others to strengthen responsible gaming efforts.

Why it matters: Birches Health’s $20M raise signals growing capital interest in behavioral health solutions tied to online gambling. With betting embedded in mainstream sports culture, regulators, insurers, and state agencies are under pressure to address social costs. Birches Health’s approach is that payer-backed, clinically rigorous care can scale where fragmented treatment options have failed—a model that could set the standard for other emerging behavioral health verticals.

Underdog CEO: “If we can be the best at building product, we’ll build the biggest company in this space.”

The news: Underdog CEO Jeremy Levine appeared on Masters of Scale earlier this month, retracing his journey from hustling on Craigslist to build StarStreet, to weathering daily fantasy’s existential legal battles, to now steering Underdog into unicorn territory with a product-first philosophy.

Zoom in: Levine’s third act is Underdog, launched in 2020 on the thesis that product velocity beats marketing spend. The company is now valued at $1.3B, fueled by “games, not transactions” and a product approach tailored to U.S. fandom rather than imported sportsbook templates. Growth bets include women’s sports—WNBA entries are up ~4x YoY, spiking when Caitlin Clark plays—and testing new prediction-market formats through a federally regulated fantasy framework.

Why it matters: Levine’s founder’s-eye view distills three lessons for betting startups: resilience is non-negotiable, product velocity beats promo spend, and regulation isn’t a hurdle—it’s strategy.

Bet Caddy CEO Tony Ryan on building the “ultimate sports remote”

The news: Bet Caddy CEO Tony Ryan wants to make the current sports viewing experience less miserable by building what he calls the “ultimate sports remote.” The app connects to users’ existing subscriptions and layers in real-time data to surface the action that matters most—whether that’s an Aaron Judge at-bat or a late-game drive in college football. The breakthrough is its notification system, which anticipates key moments ahead of broadcast latency and drops fans directly into the right stream. 

Zoom in: Getting there wasn’t straightforward. Early versions of Bet Caddy weren’t sticky enough to pull users away from the apps they already used, forcing the team to confront the reality that to succeed, they had to “break the habit” customers had with competing products. As non-technical founders, Ryan and his co-founder leaned into scrappiness—teaching themselves design tools, experimenting with APIs, and iterating on user flows until they landed on notifications as the indispensable feature. 

Why it matters: Without ad budgets, Bet Caddy has relied on comedic, highly shareable content to grow—amassing 20,000 followers in six months with skits like “historical bad bets” that drew millions of organic impressions. Today, the app is free, but Ryan sees long-term monetization opportunities in affiliate deals and premium features. The bigger vision is bolder: to become the one-button destination for sports fans everywhere. As Ryan put it, “My goal is that people only have to hit one button when they wanna watch sports at night. It’s the power button.”

Listen to the full podcast on YouTube, Spotify, and Apple Podcasts.

Sparket partners with THNDR Games to expand into skill-based play

The news: Sparket, a peer-to-peer betting platform that lets users create and wager on contests across sports, entertainment, and pop culture, has partnered with THNDR Games to add fast-paced games that fill the gaps between contests. The integration allows Sparket users to move seamlessly from real-money contests into THNDR’s skill-based titles like Blackjack, Slots, Solitaire, and Blocks. For Sparket, it’s another step in broadening engagement beyond traditional sportsbook markets by layering in always-on products.

Zoom in: The partnership aligns two companies with a shared thesis: betting should be more social, fair, and player-first. Sparket has carved out a niche by building markets around cultural moments that resonate with Gen Z and underserved audiences, Founder Evan Fisher previously told BettingStartups. THNDR extends that same philosophy with fast-paced, skill-based titles that also give Sparket regulatory flexibility in markets where iCasino is restricted—an increasingly valuable edge as operators look for compliant ways to diversify.

Why it matters: The tie-up is less about one-off engagement and more about retention—keeping users in-network with products that are sticky, socially relevant, and regulator-friendly. For founders, it’s another example of how partnerships can accelerate both product breadth and market access without shouldering all the build internally.

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