How to Avoid the Unforced Errors That Can Wipe Out Your Equity

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. 

Show Notes & Links

Connect with Spencer on LinkedIn

Definitions

Due-Diligence: This is a comprehensive appraisal of a business or investment undertaken before a merger, acquisition, or investment. It seeks to validate the information provided and uncover any potential risks or liabilities.

Earn-out: This is a financing arrangement for the purchase of a business, where the seller must meet certain performance goals before receiving the full purchase price. It reduces the buyer’s risk and aligns the interests of both parties post-acquisition.

Roll Over Investor: A rollover investor, in the context of selling a business, refers to an individual or entity that rolls some of their proceeds from the sale with the buyer. This strategy allows the seller to defer capital gains taxes and potentially leverage their expertise or resources in a new venture.

About Our Guest

Spencer Dennis

Spencer Dennis is the founder and former CEO of CoachNow, a global digital coaching platform used by thousands of coaches across 60+ sports in more than 140 countries. A former professional golfer and high-performance coach himself, Spencer launched CoachNow (originally Edufii) in 2014 to solve the real-world frustrations of staying connected with athletes outside of the practice venue. Under his leadership the SaaS-platform gained widespread adoption in sport, performance and fitness coaching. Today, Spencer combines his deep experience in operational growth, product innovation and coaching-technology strategy to mentor founders and explore new ventures while maintaining his passion for sport and athlete performance.