From “Hot Mess” to Fundable: Cleaning Up Cap Tables
In this episode of Venture Declassified, hosts Mike Kelly, Ben Pidgeon, and Jacob Schpok tackle one of the most overlooked—but most consequential—parts of startup investing: the cap table. From abandoned founder equity to a stack of mismatched SAFEs, the trio share war stories of cap tables that turn into what they like to call a “hot mess”—and why those messes can scare off the very investors a company needs most.
Along the way, they unpack the mechanics behind dilution math, option pools, and convertible notes, and shine a light on the hidden gotchas that quietly eat away at ownership. But it’s not all spreadsheets and legalese—the conversation also digs into the human side: what happens when founders don’t own enough of their company, when incentives drift out of alignment, or when optimism leads to painful down rounds.
Whether you’re an angel investor learning how to spot red flags or a founder preparing for your next raise, this episode offers a candid guide to keeping ownership structures clean, credible, and fundable.
Key Topics
• Common scenarios that create broken cap tables
• Governance challenges and the importance of transparent decision-making
• Investor psychology: how over-diluted founders and misaligned incentives undermine growth
• Practical approaches to repair ownership structures
• The legal and emotional pitfalls of restructuring without new capital on the table
• Why alignment between founders, investors, and boards determines whether companies survive or stall
Connect
Mike Kelly
• Website
Ben Pidgeon
Jacob Schpok