Spencer Dennis was an elite golfer turned coach who built CoachNow, a platform coaches loved. From the outside, it looked like a straight climb. Inside, funding choices and deal terms told a different story. This episode is a cautionary tale for any owner considering outside capital or a sale.
You’ll learn how to:
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Model who actually gets paid under preferences and convertibles.
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Cap SAFEs and track cumulative dilution before it sneaks up on you.
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Hire a COO or fractional ops help without surrendering control.
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Negotiate cash at close versus rollover stock and model both outcomes.
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Surface earn-outs, ratchets, and other “gotchas” that reappear years later.
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Keep product direction post-acquisition when the buyer “knows better.”
Listen to pressure-test your endgame before you sign the next term sheet.
Quote of the Week
My co-founders actually got completely squeezed off the cap table when we got acquired. They left with nothing.
Deals
Ask Sage, a fast-growing Generative AI company that builds secure tools for defense, national security, and other highly regulated industries, has agreed to be acquired by BigBear.ai for $250 million. The platform allows government and enterprise clients to safely deploy and manage AI models. Ask Sage is expected to generate about $25 million in annual recurring revenue in 2025, valuing the company at around 10 times its projected revenue.
