Recaps, Downrounds and Cap Table Engineering: What Really Happens When Your Growth Plan Fails with Steven Finn

Glimpse is the all-in-one, AI-powered deductions management platform for CPG brands—automating deduction capture, classification, disputes, and accounting. Recover more revenue while saving time – ⁠https://www.tryglimpse.comWhen fundraising stalls, valuations reset, and the cap table gets messy—what really happens next?In this episode, Mike sits down with Steven Finn, Partner at Siddhi Capital, to break down the tough realities of down rounds, recaps, and cap table engineering. Steven has been in the room when brands shift from celebration to survival—and shares what founders and investors need to know when things don’t go as planned: ✅ Why overcapitalization often leads to a “death spiral” ✅ When to use equity vs. debt—and why both can be predatory ✅ How mega funds create distorted valuations (and walk away fast) ✅ The psychology of “dead equity” and how to reset expectations ✅ Why insiders matter most in distressed situations ✅ How to keep founders aligned (and motivated) during a recap ✅ Why margins = runway, and why that matters more than ever ✅ What smart founders can do early to avoid being wiped out👉 If you’re a founder, investor, or operator navigating today’s tougher fundraising environment, this episode is essential listening.Timestamps 00:00 Intro 01:00 Why Fundraising Feels Harder Than Ever 04:50 Fuel on the Fire vs. Finding the Fire 07:00 Debt vs. Equity (and Predatory Capital) 12:00 When Equity Deals Get Ugly 16:30 The Mega Fund Trap & Overcapitalization 23:00 How Huge Rounds Re-Risk Companies 27:00 Recaps, Option Pools & Dead Equity 30:00 Why Venture is Now “Financing Risk First” 34:30 Rethinking Portfolio Strategy 39:50 Are Down Rounds Still a Scarlet Letter? 43:00 Why Margins = Runway 46:00 Selling Distressed Assets (and Why It’s So Hard) 50:00 How Founders Can Protect Themselves Early 53:00 Spotting Coachable vs. Uncoachable Founders 56:00 Growing in Retail Without Growing Too Fast 58:00 Steven’s Book Recommendations📬 Subscribe for more founder stories & venture insights: 👉 The Consumer VC Newsletter - https://www.theconsumervc.com/Follow Mike Gelb: Twitter / IG / TikTok → @mikegelb / @consumervc

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