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, op...

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 ...

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 parti...

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—especially when you’re a minority on the cap table and not on the board. The group exp...

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—who are feeling the pinch—and those insulated from global trade dynamics. The conversation kic...

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-volume deal flow. Jacob, Mike, and Ben begin by sharing their recent experiences at South by Southwest and qu...

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 but rather enable liquidity for shareholders looking to exit their positions. The conversation is ki...

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 advancements. Toph illustrates this urgency with the example of Chegg, a company that saw its valuation collapse due to A...

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 investors. Jacob outlines the main reasons why pre-seed and seed stages often employ safes and convertib...

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, equity, or a mix of both. Ben starts by defining waterfall analysis, explaining the allocation of returns and th...

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 like Figma can generate front-end experiences quickly, allowing for iterative design, which is particularly b...

In this insightful episode of "Venture Declassified," hosts Mike Kelly, Ben Pidgeon, and Jacob Spock tackle the often contentious topic of CEO compensation in startups. With an engaging and dynamic discussion, the trio delves into the intricate balance of aligning executive pay with company milestones and investor expectations. Key Topics • Budget implications of CEO compensation with regard to business longevity and milestones. • Risk of misalignment w...

In this episode of "Venture Declassified," hosts Mike Kelly, Ben Pidgeon, and Jacob Schpok dive into various investment strategies and market dynamics affecting angel investors. Key Topics • Investment Strategies: Sticking to goals, but being flexible • Benefits of Knowing CEOs or Board Members: Looking beyond just using deal platforms like AngelList. • Emotional Engagement in Investments • Importance of a B...

Episode Summary In this episode of "Venture Declassified," hosts Mike Kelly and Jacob Spock, along with special guest Nick Wangler, co-founer and COO of Orthodontic Details, delve into the intricate dynamics of venture capital and startup fundraising. The episode offers invaluable advice for founders navigating the challenging VC landscape, focusing on practical strategies to enhance their pitch and financial planning. Key Topics Challenges founders face with discounted estimatesVarious finan...

In this thought-provoking episode of "Venture Declassified," hosts Mike Kelly and Jacob Schpok, alongside guest Ben Pidgeon, delve into the complexities of investment decision-making in the venture capital world. This episode shines a light on the critical factors that influence whether to continue funding a company or finally "wave the white flag. The discussion starts with the importance of not relying solely on pipeline slides, which Mike Kelly criticizes as potentially fictional. He empha...

In this special episode of "Venture Declassified," recorded live at the Rally Innovation Conference, hosts Mike Kelly, Ben Pidgeon, and Jacob Spock engage with a series of live pitches and conversations with entrepreneurs and founders. They unpack the complex dynamics of the fundraising landscape for startups, exploring how the backgrounds of entrepreneurs—whether they are repeat founders or first-timers—significantly influence their approach and success in securing investments. Mike and Ben ...

In this enlightening episode of "Venture Declassified," hosts Jacob Schpok, Ben Pidgeon, and Mike Kelly take a deep dive into the intricacies of Series A valuations, fundraising strategies, and the unique challenges faced by Midwest startups. The episode sheds light on the complex dynamics that come into play when a company with $3 million in annual recurring revenue aims for a Series A round, touching on standard valuation multiples, dilution impacts, and capital efficiency. The discussion ...

In this episode of Venture Declassified, hosts Mike Kelly and Ben Pidgeon explore the complexities of managing angel syndicate groups and the art of curating investment opportunities. Both Mike and Ben run angel syndicates, creating SPVs (Special Purpose Vehicles) for investments, and they highlight the challenge of recommending numerous deals each year without overwhelming their investors. Ben elaborates on his group's approach of working on multiple deals simultaneously, often over a two to...

Episode Summary Welcome back to Venture Declassified. In this episode, we continue our conversation into the nuances of creating an influential pitch. Jacob and Ben share their insights on the significance of active listening to evaluate a team effectively. We then pivot to tackle the challenging topic of setting valuations and discuss vital metrics including revenue, customer acquisition costs, and churn rates. Expect to hear candid conversations about founders' narratives, why present...

Episode Summary In this episode of Venture Declassified, hosts Mike Kelly, Jacob Schpok, and Ben Pidgeon come together to talk about the fundamentals of an influential pitch. This episode promises to strip away the misconceptions and focus on what truly matters during investor presentations. As the hosts delve into the narrative aspect of pitch decks, they emphasize clarity and accuracy in communicating the startup's vision and potential. The episode also explores the strategic presentation o...