Hint Health

Zach Haldsworth spent about three years at a healthcare company before co-founding Hint Health with Graham. While he didn't come from a healthcare background, that experience opened his eyes to how broken the system was. The pair spent two to three months evaluating half a dozen ideas, using a specific rubric: Could the innovation fundamentally transform the trillion-dollar problem in US healthcare? Did it involve building technology? And could they move quickly and generate revenue fast?

They landed on direct primary care—a growing community of doctors stepping outside the traditional insurance fee-for-service model to work directly with patients or employers. These doctors were managing payments and membership using spreadsheets. Zach and Graham believed they could build the software backbone these practices needed.

Once they identified the market, the founders moved at lightning speed. They attended industry events, did cold calling and networking across the country, and began coding almost immediately. Zach closed deals while Graham built the product. Within 30 days, they had their first paying customer. The initial customers weren't small pilots—they were doctors about to spend $20,000 customizing Salesforce. Zach offered custom builds for $15,000-$20,000, and they said yes. One first customer was a doctor named Dr. Rob who worried: "If you guys screw up my payments, I go out of business." Zach's response was radical: "I'll personally guarantee your payroll out of my own pocket if we fail." Dr. Rob signed up immediately.

The first 10 customers came within three to four months. Early deals were a mix of custom projects and a transaction-based model (1% of all payments through the platform with no upfront fee), which reduced friction.

The biggest objections weren't about trust in a startup—they were practical. First: migration was terrifying. Patient data, payment info, and membership details were scattered across systems. Second: operational risk. Missing a single payroll could sink a practice. Zach overcame the migration objection by offering free migration services (which he initially thought wasn't scalable but became routine after doing it 10 times). For the trust issue, he leaned hard on mission-driven messaging: "We're entrepreneurs committed to supporting your community." And when needed, he put his own money on the line.

Once they had 10 customers generating word-of-mouth and social proof, growth began to compound through referrals and inbound leads.

Zach reflects that moving too fast was both a blessing and a curse. They got to revenue in 30 days, but they also accumulated product debt. Had they spent more time embedded in customer workflows—even working for free as an admin for a few weeks—they likely would have avoided architectural mistakes that became expensive to fix later. Speed equated to early traction but higher long-term costs of change.

Fundraising was deceptively easy at first. They raised $250k initially, expanded to $1.3 million in their first round, using small momentum tricks (like mentioning a YC interview to accelerate investor timelines). But this created a trap: Zach assumed it would always be easy. It wasn't. Over the lifetime of the company, he's pitched over 1,000 investors, faced rejection based on TAM concerns, and dealt with increasing dilution.

Horizontal expansion into adjacent healthcare verticals (specialty care, employer on-site clinics) looked promising but didn't scale without rebuilding the entire go-to-market engine, community relationships, and sales infrastructure he'd already built in DPC. The lesson: adjacent markets aren't as adjacent as they seem.

Hint Health now serves close to 1,000 customers across 750,000 lives and processes over $500 million in payments annually. They've raised $60 million (expanded to roughly $64 million by the end of the podcast) and employ around 40 people. Revenue is approaching eight figures in ARR.

Growth shifted from pure cold outreach to word-of-mouth, partnerships with complementary vendors (EMR systems), and a signature annual conference (now 450+ attendees) that reinforces mission alignment without being a direct sales vehicle. The conference doubled as community building and partner development, so powerful they turn away sponsorship money to maintain its integrity.

Zach acknowledges the venture path has required more dilution than he'd like because the DPC market, while growing, is nascent and smaller than traditional VCs prefer. But the mission—transforming healthcare from first principles—keeps him grinding. He's been at it for eight years and expects a multi-decade journey. Without that underlying mission, he says he would have quit when fundraising and growth became harder.

The biggest lesson: don't chase social media metrics or billionaire comparisons. Define success on your own terms. 5% of a billion-dollar company beats 100% of nothing—but so does 80% of a profitable $20 million business. The path matters more than the exit size.