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

• LinkedIn

• Website

• Developer Town

Ben Pidgeon

• LinkedIn

• VisionTech

Jacob Schpok

• LinkedIn

• Elevate Ventures

Hear more interviews and stories like this one at www.VentureDeclassified.com

The information provided on the show is not intended to be investment advice and should not be relied upon as such. The investors on today’s episode are providing their opinions based on their own assessment of the businesses or topics presented. Those opinions should not be considered professional investment advice. If they start up pitched as a part of this episode, it is for informational purposes only and is neither an offer to purchase nor a solicitation of an offer to sell, subscribe for or buy any securities.

In this episode of Venture Declassified, hosts Mike Kelly, Ben Pidgeon, and Jacob Schpok take a hard look at bridge rounds—what they are, when they make sense, and when they’re really just a disguised recap.

The conversation starts with definitions: a bridge round is typically a smaller, short-term raise—often structured as a convertible note or SAFE—intended to extend a company’s runway until the next major milestone. But as the hosts point out, bridges can fall into three very different categories: a pivot where the company needs fresh conviction, a quick infusion of capital to hold a team together until revenue catches up, or a milestone-driven raise where investors want a bit more proof before the next priced round.

The discussion also touches on founder storytelling and investor diligence. Is the pitch grounded in new information and realistic milestones, or is it just recycled pipeline promises? Asking for the prior pitch deck, comparing KPIs over time, and paying attention to who else is writing checks can reveal the true state of play.

Whether you’re an angel investor considering a bridge, a founder debating how to structure a raise, or just curious about the mechanics of early-stage capital, this episode offers a candid and practical breakdown of how bridges can either keep a company on track—or lead it further into trouble.

Key Topics

• Defining bridge rounds and how they differ from full priced round

• Common scenarios where bridges arise: pivots, milestone-driven raises, and team runway extensions

• Extension rounds and how insider vs. outsider participation signals confidence

• Market conditions and their impact on valuations and recapitalizations

• Risks of ego and financial incentives driving bridge decisions

• Governance dynamics: insider commitment, board participation, and signaling strength

• Key diligence questions for angels considering a bridge investment

Connect

Mike Kelly

• LinkedIn

• Website

• Developer Town

Ben Pidgeon

• LinkedIn

• VisionTech

Jacob Schpok

• LinkedIn

• Elevate Ventures

Hear more interviews and stories like this one at www.VentureDeclassified.com

The information provided on the show is not intended to be investment advice and should not be relied upon as such. The investors on today’s episode are providing their opinions based on their own assessment of the businesses or topics presented. Those opinions should not be considered professional investment advice. If they start up pitched as a part of this episode, it is for informational purposes only and is neither an offer to purchase nor a solicitation of an offer to sell, subscribe for or buy any securities.

In this episode of Venture Declassified, hosts Jacob Schpok, Ben Pidgeon, and Mike Kelly unpack the inner workings of Special Purpose Vehicles (SPVs) and their role in managing follow-on investments. Drawing from recent real-world scenarios, the trio explores how SPVs are structured, how pro rata rights work in practice, and what happens when not all investors are on board for additional funding rounds.

Ben shares a current “pay-to-play” situation, explaining how failing to participate in a follow-on can push investors down the preference stack—or even convert them to common shares—dramatically impacting potential returns. The conversation dives deep into mechanics like preference stacks, pari passu arrangements, capital calls, and how SPVs track ownership across multiple rounds. Mike adds perspective on structural differences between manager-led and member-managed SPVs, and why understanding your voting rights and obligations matters.

They also highlight the nuances of running internal “waterfalls” within an SPV to distribute returns fairly among investors in different rounds. From the realities of last-minute investor dropouts to the importance of clear governance, the hosts offer a candid look at the operational and relational challenges that come with managing pooled investments.

The discussion wraps with practical guidance for angels considering joining or creating their own SPV—covering fee structures, deal economics, and minimum check sizes. Whether you’re investing through an angel group or setting up an SPV with friends, this episode delivers a grounded, experience-based look at protecting your position, avoiding unnecessary dilution, and making informed follow-on decisions.

Key Topics

• Defining SPVs and their role in pooled startup investments

• Handling last-minute investor dropouts and capital call gaps

• Fee structures, hurdle rates, and carried interest models

• Governance considerations and voting rights within SPVs

• Risks and benefits of forming your own SPV with peers

• Minimum check sizes and factors influencing deal participation

Connect

Mike Kelly

• LinkedIn

• Website

• Developer Town

Ben Pidgeon

• LinkedIn

• VisionTech

Jacob Schpok

• LinkedIn

• Elevate Ventures

Hear more interviews and stories like this one at www.VentureDeclassified.com

The information provided on the show is not intended to be investment advice and should not be relied upon as such. The investors on today’s episode are providing their opinions based on their own assessment of the businesses or topics presented. Those opinions should not be considered professional investment advice. If they start up pitched as a part of this episode, it is for informational purposes only and is neither an offer to purchase nor a solicitation of an offer to sell, subscribe for or buy any securities.