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

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.

Episode Summary

In 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

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, 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 Bio

Grant 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

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.