Venture Declassified

Hosted by Mike Kelly, Ben Pidgeon, and Jacob Schpok

Business Investing

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Latest episode

Oct 2026

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About the show

Venture Declassified is here to provide you with practical insights, expert advice, and a deeper understanding of the investment landscape for first-time investors. Hosted by a team of seasoned investors and financial experts, this podcast is tailor-made for newcomers who are eager to learn about the fundamentals of investing and want to make informed decisions. We understand that starting your investment journey can be intimidating, but our goal is to demystify the process and equip you with the knowledge and tools needed to succeed.

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43 recent

October 5, 202628 min

Swapping CEOs: When the Founder Isn’t the Right Fit

Swapping out a startup CEO is never a simple decision—especially when that CEO is also the founder. In this episode, Ben, Mike, and Jacob dig into when a leadership change makes sense, why it can be so disruptive, and how boards can tell the difference between a founder who needs help and one who may no longer be the right person to lead the company. They share stories from their own portfolios, including one CEO transition that helped a company more than double its ARR, and another where board micromanagement helped send things in the opposite direction. The conversation also gets into the less obvious pieces of a CEO transition: founder ownership and compensation, messy cap tables, burnout and flight risk, finding replacement talent, and what happens when a founder moves into a different role instead of leaving altogether. And when things get really ugly? The hosts discuss the “nuclear option,” interim CEOs, and whether your board should have a backup quarterback ready to step in. Key Topics • When and why a startup might need a new CEO • The challenges of replacing a founder at different stages of a company • Successful vs. disastrous leadership transitions • Board transparency, executive sessions, and avoiding surprises • Founder compensation, equity, and cap-table health • Using executive recruiters to find new leadership 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.

September 21, 2026Episode 4218 min

The Fine Line Between Pitching and Selling

What happens when investors have to pitch a deal to other investors? In this episode, Mike, Ben, and Jacob turn the tables and talk about the art of selling an investment without sounding like you’re selling it too hard. The hosts discuss everything from putting your own “chip on the table” to asking about founders' salaries, ownership, and even what happens if a husband-and-wife founding team gets divorced. They also get into the challenge of syndicating deals with friends and fellow investors, where credibility matters just as much as enthusiasm—and where overselling a deal can come back to bite you the next time you have something to syndicate. Ultimately, the hosts come back to a pretty simple idea: good investing conversations aren't about convincing someone to say yes. They're about being honest enough to share both why you believe in the opportunity and where you think it could go wrong. Key Topics • Why syndication becomes necessary for larger fundraising rounds • Investor-to-investor communication vs. founder-to-investor communication • The importance of knowing your audience when pitching a deal • The risks of pushing an investment too aggressively • Using smaller checks to reduce investment and relationship risk • Separating current-round participation from past investment • Reading signals from investors who choose not to follow on • Asking uncomfortable questions during investment diligence • Planning for personal and professional contingencies at a startup 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.

September 7, 2026Episode 3936 min

AI One Year Later: What's Changed?

In this episode of Venture Declassified, Mike Kelly, Ben Pidgeon, and Jacob Schpok revisit one of the fastest-moving topics in tech: artificial intelligence. Fourteen months after their last AI discussion, the hosts compare notes on how dramatically the landscape has changed—from building internal tools with platforms like Lovable and Claude to using AI to develop production-ready software in a fraction of the time it once took. What once felt experimental has quickly become part of the everyday toolkit for founders, operators, and investors alike. But the conversation quickly moves beyond the latest tools. The hosts explore what AI means for startup investing, debating whether traditional SaaS businesses are becoming less attractive as software development costs continue to fall. They discuss why customer validation now requires more than a list of interviews, how investors should evaluate companies whose products can be "vibe coded," and what competitive advantages—like proprietary data, trusted brands, and marketplaces—still create lasting value. The episode wraps with a look toward what's next, including agentic AI, autonomous workflows, and the security considerations that come with giving AI greater responsibility. Whether you're building software, investing in startups, or simply trying to keep pace with AI's rapid evolution, this episode offers a practical snapshot of where the technology stands today—and where the hosts believe it's headed. Key Topics • How AI-assisted development is changing the economics of software creation • When human expertise still matters in software architecture and product design • The evolving expectations for pre-seed founders seeking investment • Security risks surrounding AI agents and prompt injection attacks • Practical AI tools founders and investors should be experimenting with today 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.

August 31, 2026Episode 4145 min

Valuation, Burn Rate & Pipeline: The VC Math Every Founder Should Know

Mike, Ben, and Jacob swap the back-of-the-napkin calculations they rely on when evaluating startups, from market size and valuation multiples to sales pipelines, burn rates, and runway. Along the way, they challenge each other's assumptions, share where those quick calculations can go wrong, and explain why venture investing is just as much about asking the right questions as it is crunching the numbers. The conversation also explores the softer side of diligence: why founders earn credibility by showing their work instead of polishing every metric, how repeatable sales matter more than flashy growth projections, and why today's AI costs create a whole new set of investment questions. Equal parts practical framework and friendly debate, this episode offers founders and investors an inside look at how venture capitalists think before they ever build the spreadsheet. Key Topics • Market sizing and estimating venture-scale exit potential • Why post-money ownership matters more than pre-money valuation • Understanding dilution from SAFEs, convertible notes, and option pools • Burn rate, runway, and raising enough capital to reach meaningful milestones • Trust-building signals founders can provide during diligence • How AI infrastructure costs and technical decisions impact future scalability 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.

August 17, 2026Episode 4026 min

Investment Thesis

Angel investors love to say they have an investment thesis—but do most people actually have one before they start writing checks? In this episode, the guys unpack what an investment thesis really is, why it matters, and how it can keep investors from chasing shiny objects (or the latest AI hype train). Along the way, they compare their own approaches to investing, debate whether founder quality outweighs market timing, and admit that sometimes the best investment isn't just about returns—it's about satisfying your own curiosity. The conversation wanders through everything from power law returns to coachability, and why patience is one of the most underrated advantages an investor can have. With plenty of real-world examples, and a few self-deprecating jokes, the hosts explore how experienced investors develop conviction without becoming dogmatic—and why a good thesis should evolve as you gain experience. They close with a challenge for listeners: write down your own investment thesis and send it in for a future episode, because nothing tests your thinking quite like putting it on paper. Key Topics • Building guardrails to avoid FOMO and emotionally driven investments • Why founder grit and coachability often outweigh industry expertise • Investing in industries you know versus industries you want to learn about • Timing, discipline, and avoiding overhyped markets • Concentrated versus diversified investing within the same market • Creating a follow-on investment strategy for winning companies 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.

July 13, 2026Episode 385 min

Quick Tip: The Problem with Pipeline Numbers

In this Venture Declassified Quick Tip, the hosts tackle one of the most common—and most misleading—metrics in startup updates: pipeline. Mike, Ben, and Jacob explain why experienced investors are skeptical of massive pipeline numbers at the pre-seed and seed stages, and what founders can do to present a more credible picture of future revenue. It's a quick lesson in separating real traction from wishful thinking. 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.

June 29, 2026Episode 371 hr 5 min

From Prototype to Production: The Hard Tech Investor's Guide

In this special crossover episode of Venture Declassified, Mike Kelly, Ben Pidgeon, and Jacob Schpok join Grant Chapman on the Hard Tech Podcast to tackle a question many angel investors wrestle with: how should you evaluate hard tech opportunities differently from software companies? The discussion explores how investors should think about technical expertise, scalability, and the transition from a promising prototype to a manufacturable product. Along the way, the hosts compare the unique risks of software and hardware, debating whether hard tech is truly less nimble—or simply misunderstood by investors who are more familiar with SaaS. The episode ultimately turns into a broader conversation about investor psychology, founder quality, and the tradeoffs between risk and reward. While hardware companies often require more capital and patience upfront, the group discusses why they can benefit from deeper competitive moats, stronger acquisition dynamics, and more defensible technology. For investors looking beyond software, this episode offers a candid look at what makes hard tech both challenging and compelling. To hear more from Grant Chapman and explore additional conversations on hardware innovation, startups, and product development, visit the Hard Tech Podcast at thehardtechpodcast.com Key Topics • How hard tech differs from software at the pre-seed, seed, and Series A stages • The transition from proving a concept to scaling manufacturing • Technical risk versus execution risk in hardware and software companies • The role of customer discovery before significant capital is committed • Acquisition dynamics and the strategic value of hardware intellectual property • Capital efficiency, power-law investing, and portfolio construction considerations 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.

May 25, 2026Episode 3625 min

When Startup Valuations Stop Making Sense

Episode Summary In this episode of Venture Declassified, Mike Kelly, Ben Pidgeon, and Jacob Schpok tackle one of the murkier concepts in startup investing: mark-to-market valuations. What starts as a conversation about portfolio reporting quickly turns into a candid debate about spreadsheets, “black magic,” and the uncomfortable reality that startup valuations are often far more subjective than investors would like to admit. The hosts break down how mark-to-market works in venture investing, why new financing rounds are typically used as valuation anchors, and how institutional investors think about portfolio appreciation before an actual exit ever occurs. Along the way, they unpack the tension between reporting optimistic numbers and staying grounded in reality—especially when insider-led rounds, soft pricing, or struggling companies muddy the picture. But the conversation goes beyond valuation math. The group also explores the role of sentiment analysis, investor psychology, and pattern recognition when evaluating portfolio health over time. From “sad face” companies with strong markups to founders who keep promising a Series A “six months away” for years, the episode offers an honest look at how experienced investors separate signal from noise when deciding where to keep deploying capital. Key Topics • What “mark-to-market” actually means in startup investing • Why venture valuations are fundamentally different from public markets • The role financing events play in startup price discovery • How insider-led rounds can distort portfolio valuations • Different approaches to handling SAFEs and convertible notes in reporting • Why some investors pair valuation tracking with sentiment analysis • The importance of portfolio construction versus evaluating a single deal • Using valuation trends as one signal—not the whole story—when making follow-on decisions 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.

April 20, 2026Episode 342 min

Quick Tip: Drag-Along Rights

In this quick Venture Declassified “nugget,” Mike Kelly, Ben Pidgeon, and Jacob Schpok break down the concept of drag-along rights—one of those legal terms that can have major real-world consequences for investors and founders. Using a real example involving a missed acquisition opportunity, the hosts explain why investors sometimes insist on having the power to force a sale. It’s a fast look at how governance provisions can protect investors from emotional decision-making when big offers hit the table. If you’ve ever wondered why drag-along clauses show up in deal documents, this short episode delivers the answer. 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.

April 13, 2026Episode 3531 min

The Reality Behind Startup Exits

In this episode of Venture Declassified, hosts Mike Kelly, Ben Pidgeon, and Jacob Schpok unpack one of the most misunderstood moments in startup investing: the exit. While headlines often highlight big acquisition numbers, the hosts explain why the reality behind those numbers is rarely as straightforward—or as lucrative—as it first appears. The conversation breaks down the different ways exits actually play out for angel investors. From acquihires to strategic acquisitions and deals structured with stock, earnouts, or buyer notes, the hosts explore how value is really distributed after a company is sold. They also walk through why the headline price doesn’t necessarily reflect what investors ultimately receive, and how deal structure can dramatically shape the outcome. Along the way, the group shares practical perspective on how angels should think about liquidity, timing, and expectations when a portfolio company exits. Whether you’re new to angel investing or have a few deals under your belt, this episode offers a candid look at what “success” can really mean when the exit finally arrives. Key Topics • The range of exit scenarios founders and investors may encounter • How earnouts and deferred payments affect investor returns • When equity in the acquiring company becomes part of the deal • Understanding acquihires and their impact on early investors • The role of post-acquisition performance targets • Why exit timelines can stretch years beyond the initial transaction • Managing expectations around liquidity events in early-stage investing 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.

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