Venture Declassified

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, i...

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 tea...

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 fr...

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...

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 ou...

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...

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 fro...

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 in...

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 h...

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...

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 sal...

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 scenari...

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 rout...

Episode Summary Recorded 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-suppor...

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 c...

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...

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 r...

Episode Summary In this episode of “Venture Declassified,” hosts Mike Kelly, Jacob Schpok, and Ben Pidgeon are joined by super angel investor Ken Miller for a candid conversation on the art and reality of exercising influence as an angel investor.     The discussion kicks off with the dilemma many angels encounter: what to do when you see a portfolio company making decisions you disagree with—espe...

In this insightful episode of "Venture Declassified," hosts Jacob Spock, Mike Kelly, and Ben Pidgeon are joined by guest Ken Miller to tackle the timely and complex topic of tariffs, and their ripple effects on startups, investors, and the broader business ecosystem. The crew dives straight into the current landscape, highlighting the divide between companies with international exposure—...

In this lively episode of "Venture Declassified," hosts Mike Kelly, Ben Pidgeon, and Jacob Spock dive deep into their screening processes, offering a backstage pass to how venture capital decisions are made. The episode is a fascinating exploration of how these experts engage with potential portfolio companies, balance efficiency with thoroughness, and deal with the challenges of high-vo...

In this episode of "Venture Declassified," hosts Ben Pidgeon, Mike Kelly, and Jacob Schpok delve into the intriguing world of secondary markets. They explore how these markets offer a mechanism for current shareholders in privately-held companies to sell their shares to private entities. With a candid approach, the hosts detail how these transactions do not inject new cash into companies...

In this insightful episode of "Venture Declassified," hosts Ben Pidgeon, Mike Kelly, and Jacob Schpok join guest Toph Day to explore the rapid shifts within Indiana's burgeoning tech ecosystem. The discussion centers on the theme of "Innovate or Evaporate," emphasizing the need for businesses to adapt to swiftly evolving technological landscapes, particularly with AI advan...

Episode Summary In this engaging episode of "Venture Declassified," hosts Mike Kelly, Ben Pidgeon, and Jacob Schpok unpack the various types of investment vehicles and the appropriate contexts for their use. The episode is loaded with expert insights into the nuances of safes, convertible notes, and equity financing, making it a must-listen for both budding entrepreneurs and seasoned inv...

Episode Summary In this enlightening episode of "Venture Declassified," hosts Ben Pidgeon, Mike Kelly, and Jacob Spock tackle the subject of waterfall analysis, offering listeners a clear understanding of its role in the investment process. The topic comes to life through a real-life scenario where their portfolio company faced an acquisition offer, leading to choices between cash, equit...

In this episode of "Venture Declassified," hosts Jacob Schpock and Mike Kelly dive into an engaging discussion centered on using AI tools to create a Minimum Viable Product (MVP). They explore the necessary skills, costs, and time commitment involved in product development with a focus on leveraging low code/no code platforms and developer productivity tools. Mike emphasizes how tools li...