Venture Declassified

Hosted by Mike Kelly, Ben Pidgeon, and Jacob Schpok

Business Investing

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Latest episode

May 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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36 recent

May 25, 2026Episode 3625 min

When Startup Valuations Stop Making Sense

Episode SummaryIn 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 ConnectMike 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.comThe 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. ConnectMike Kelly• LinkedIn• Website• Developer Town Ben Pidgeon• LinkedIn• VisionTech Jacob Schpok• LinkedIn• Elevate VenturesHear more interviews and stories like this one at www.VentureDeclassified.comThe 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 ConnectMike Kelly• LinkedIn• Website• Developer Town Ben Pidgeon• LinkedIn• VisionTech Jacob Schpok• LinkedIn• Elevate VenturesHear more interviews and stories like this one at www.VentureDeclassified.comThe 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.

March 30, 202619 min

What Happens When It’s Time to Dissolve a Startup

In this episode of Venture Declassified, hosts Mike Kelly, Ben Pidgeon, and Jacob Schpok dive into a reality every startup investor eventually faces: what happens when a company simply doesn’t work out. The conversation kicks off with Ben stepping off a real-time investor call dealing with a struggling portfolio company, which leads the group into an honest discussion about dissolutions, asset sales, and how investors determine “who gets what” when the outcome falls short of expectations. The hosts break down how liquidation preferences, funding rounds, and cap table structures influence the waterfall when a company winds down. Along the way, they explore the practical side of navigating these situations—why transparency, documentation, and investor alignment matter when difficult decisions are being made quickly and under pressure. But the discussion isn’t just about mechanics. The group also reflects on the human side of startup failures—from the emotional toll on founders who have poured years into their companies to the responsibility investors have to approach these moments with empathy and professionalism. The episode closes with a look at how experienced investors run postmortems on failed investments and what lessons can be learned for future deals. Key Topics • Recognizing early warning signs that a startup may be struggling • How funding rounds and investor preferences affect payout order • The difference between convertible notes, SAFEs, and priced rounds in downside scenarios • Why transparency and documentation reduce investor conflict • The role angel investors can play during difficult portfolio moments • Product-market fit vs. management issues as causes of startup failure • Running post-investment debriefs to improve future investment decisions ConnectMike 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.comThe 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.

March 16, 2026Episode 3225 min

Startup Funding: When the Founder Becomes the Bank

Episode SummaryIn this episode of Venture Declassified, hosts Mike Kelly, Ben Pidgeon, and Jacob Schpok unpack a topic that occasionally pops up in startup financials but rarely gets discussed openly: founder loans. What happens when a founder puts their own money into the company—and more importantly, what happens when it’s time to raise outside capital? The group walks through common scenarios where founders fund early operations out of necessity, only for that contribution to later show up on the balance sheet as a liability. The conversation explores why these arrangements often lack proper documentation, how they’re perceived during diligence, and why investors tend to get uneasy if new capital is used to pay founders back. Along the way, the hosts discuss practical approaches for handling these situations without derailing a round—from structuring repayment expectations to converting obligations into equity. With their usual mix of candor and dry humor, the crew offers a behind-the-scenes look at how investors actually evaluate these situations—and what founders should think about before lending their own startup money. Key Topics• The risks of undocumented or informally structured founder financing• Investor reactions when repayment is tied to a new funding round• Options for restructuring or resolving founder debt before closing a round• The role of board oversight and investor communication in these situations• Early-stage cash constraints that lead founders to personally fund operations• Navigating founder incentives and fairness during financing events• How experienced investors evaluate these situations during diligence ConnectMike 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.comThe 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.

February 16, 202651 min

Investing in Hardware: Honest Timelines, Burn Rates, and Brutal Truths

In this episode of Venture Declassified, Mike Kelly and Jacob Schpok are joined by Grant Chapman, co-founder of Glassboard, along with GrowthX Partner Jeanette Renshaw for a candid conversation about what it really takes to build—and invest in—hard tech. Drawing from deep, hands-on experience across hardware, medtech, and physical product development, the group unpacks why hardware timelines routinely stretch, why testing and validation are chronically underestimated, and why optimism is often the most expensive line item in a founder’s budget.Jeanette brings a go-to-market and founder-coaching lens to the discussion, highlighting how early assumptions around customers, timelines, and revenue expectations often collapse once physical constraints enter the picture. Grant shares hard-earned lessons from working with founders who discover too late that physics, compliance, and manufacturing don’t bend to pitch decks, while Mike and Jacob ground the conversation in what angels should realistically expect when evaluating hard tech opportunities.Together, the group offers a clear-eyed look at how hardware startups can responsibly de-risk, raise capital without overpromising, and avoid the common traps that derail otherwise promising companies. For angel investors, this episode delivers practical insight into separating ambition from execution—and understanding when patience, not speed, is the real advantage. Guest BioGrant Chapman is the CEO and co-founder of Glassboard, a hardware product development firm that helps startups and established companies design, prototype, and bring complex physical products to market. With over a decade of experience in hard tech and engineering, he leads development efforts that bridge early-stage validation and scalable manufacturing. Under his leadership, Glassboard has become a trusted partner for founders navigating the unique risks and execution challenges of hardware innovation. Chapman’s work emphasizes rigorous testing, practical product strategy, and connecting founders with the right capital and expertise to accelerate growth. LinkedIn Website Jeanette Renshaw is a Partner and Managing Director of Startup Growth at GrowthX, where she helps B2B founders get to market and build repeatable revenue engines. With over a decade of experience across 20+ tech industries, she has worked hands-on with hundreds of startups, coaching founders through early-stage sales, go-to-market strategy, and customer validation. LinkedIn Website Key Topics• Why hardware timelines are longer and less forgiving than software• How to spot unrealistic timelines and missing milestones in pitch decks• Ethical ways to validate hardware demand before building the product• Why early crowdfunding often backfires for hardware startups• How founders accidentally alienate early investors through optimism• What true “de-risking” looks like at each stage of hardware development• Why hard tech investing is nearly impossible without domain expertiseConnectMike Kelly• LinkedIn• Website• Developer TownBen Pidgeon• LinkedIn• VisionTechHear more interviews and stories like this one at www.VentureDeclassified.comThe 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.

January 19, 2026Episode 3151 min

Narrow First, Scale Later: A Smarter Go-To-Market Playbook

Episode SummaryRecorded live from the Rally Innovation Conference, this episode of Venture Declassified features a wide-ranging and candid conversation with Jeanette Renshaw, Partner at GrowthX, on what actually drives early-stage success: understanding your ideal customer and learning how to sell—before you run out of runway. Jeanette breaks down why startup sales remains one of the least-supported (and most misunderstood) skills founders need to master, especially at the pre-seed and seed stages. The discussion digs into how investors can evaluate whether founders truly understand their market, moving past vanity metrics like the number of customer interviews and instead focusing on outcomes, clarity, and execution. Jeanette introduces GrowthX’s concept of intentional “micro-sprints,” explains why ICPs should be painfully narrow early on, and shares why founders—not hired guns, consultants, or AI—must own early sales conversations themselves. From red flags that signal poor coachability to practical guidance on avoiding the “do nothing” status quo in buyer behavior, the episode blends humor, real-world examples, and hard-earned lessons from working deep in the weeds with founders. For angel investors and early-stage operators alike, this conversation offers a grounded look at how learning velocity, focus, and disciplined go-to-market work can dramatically reduce execution risk. Key Topics• Why early-stage go-to-market success depends on focus, not scale• How investors can evaluate ICP clarity without relying on interview counts• The risks of outsourcing sales learning too early• When AI-generated feedback helps—and when it misleads• Signals investors should look for to assess founder coachability• Common red flags that indicate execution risk• How founders overcome the “do nothing” status quo in buying decisions• Why documenting learnings matters more than polished decks Guest BioJeanette Renshaw is a Partner and Managing Director of Startup Growth at GrowthX, where she helps B2B founders get to market and build repeatable revenue engines. With over a decade of experience across 20+ tech industries, she has worked hands-on with hundreds of startups, coaching founders through early-stage sales, go-to-market strategy, and customer validation. LinkedIn Website ConnectMike 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.comThe 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.

October 6, 2025Episode 291 hr 3 min

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 ConnectMike 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.comThe 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 22, 2025Episode 2821 min

The Good, the Bad, and the Risky: Understanding Bridge Rounds

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 ConnectMike 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.comThe 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 8, 2025Episode 2728 min

Navigating Follow-On Rounds Through Special Purpose Vehicles

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 ConnectMike 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.comThe 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.