Coach.me

Tony Stubblebine had already built Lyft, a goal-tracking community with a million users, but he realized the eyeballs business model was broken. "If you can't get 50 or 100 million users, you're not really anything at all," he explains. What excited him wasn't helping people floss—even if Coach.me had "helped more people floss than any other organization in the world." What he really wanted was to see people become great entrepreneurs, great athletes, and elite performers.

The turning point came through an unexpected collaboration. Tony partnered with Tim Ferriss to recruit coaches from the Lyft community to run a challenge (an abstinence challenge with multiple components). The results were stunning: people who hired a coach were three times more successful than those in the free version. The conversion rate hit 5%—almost double the 3% benchmark for freemium products. Every metric worked: revenue, conversion, outcomes. "Oh, shit," Tony remembers thinking, "like we have something here."

January 1st, 2015, they relaunched Lyft as Coach.me, a marketplace for coaching. But here's the crucial insight: they didn't just build a marketplace. They invented the product being sold in it. "Traditional coaching had never been brought online," Tony says. "It's way too expensive. You have no idea who's a good coach because you can't track any of the outcomes." Coach.me pioneered "digital coaching"—message-based daily coaching through their platform, giving clients daily access to their coach with full data transparency.

The Tim Ferriss challenge proved the model worked. The platform takes a 50% cut when Coach.me brings the client, and 70-90% when the coach brings their own. Revenue exploded: $82,000 in 2014, $650,000 in 2015, with $2 million projected for 2016. By December 2015, they had about 150 coaches actively generating revenue monthly, though 5,000 were in the database.

The magic metric turned out to be lifetime value (LTV). When Coach.me first launched, LTVs were just $42 per user per year. "Shit, this is not good," Tony thought. They dug into the problems—bad coach-client matches, poor onboarding, missing features—and fixed them. LTV jumped to $90. Then they discovered 40% of clients hire more than one coach, and started adding phone calls and premium services. Unlike traditional coaching organizations, "we are sitting on all of the data about what works and what doesn't work."

With minimal burn ($20k/month net after revenue), Coach.me closed a rolling convertible note starting in December 2015, targeting $500k total. Evan Williams (founder of Blogger and Medium) joined the board and works one floor above Tony. The company is obsessed with one thing: increasing client lifetime value through product quality, better coach training informed by real outcome data, and expanding the coaching categories beyond the early mindfulness and habit-building coaches.