A Cautionary Tale for Founders
“Spencer Dennis built the technology product CoachNow to guide golfers between coaching sessions. He ended up making many decisions that left him with little to show for a product customers loved,” shares Sam Thompson, a Minneapolis business broker and the president of M&A firm Transitions In Business. “In this episode Spencer talks about preserving product control, hiring a COO, and what he’d do differently.”
Spencer Dennis was an elite golfer whose playing career ended with spine surgery in his teens. He became a tour-level coach, running high-performance programs for juniors, college players, and pros. Managing parents, trainers, and recruiters through texts and email was chaos, so he built CoachNow to guide athletes between sessions.
CoachNow caught on quickly with busy coaches. Then a run of decisions—turning off revenue under “grow fast” advice, stacking convertibles and preferences, and accepting stock-for-stock deals—left Spencer with little to show for a product customers loved. This is a cautionary tale for any owner negotiating with “sophisticated” investors.
You discover how to :
- Keep charging from day one and sidestep the “free to grow” trap.
- Map liquidation preferences so you know who gets paid—and who gets wiped.
- Cap and track SAFEs before a dozen small checks equal a big chunk of your company.
- Hire a COO or fractional operators instead of surrendering the CEO seat.
- Demand clarity on cash at close versus rollover paper—and model both outcomes.
- Surface earn-outs, ratchets, and “gotchas” that reappear years later.
- Preserve product control post-acquisition when the buyer “knows better.”
- Raise from friends and clients without taking on emotional debt.
Listen to the episode before you sign a term sheet with an institutional acquirer.