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 explores the most effective (and least destructive) ways to voice concerns, —asking sincere, probing questions to prompt founders to re-examine their assumptions.

Ken, Ben, and Mike unpack scenarios from disengaged boards to founders clinging to wishful thinking, debating whether tough conversations should happen one-on-one over lunch or in the boardroom. They dissect the role of data in clarifying disagreements, how to build consensus among other investors, and the importance of humility—accepting you might be wrong, even if you’re passionate and experienced.

The episode also tackles the reality of misaligned investor goals, such as the choice between holding out for a potential big exit versus taking chips off the table in a tough market. Throughout, the hosts keep it real about the ups and downs of angel investing—reminding listeners that failures are common, big wins can come unexpectedly, and open debate is often the healthiest path forward.

Whether you’re an experienced angel or just getting started, this episode is brimming with practical wisdom for navigating the emotional, interpersonal, and strategic challenges of influencing startups from the sidelines.

Ken Miller

With 30 years of experience developing teams and focusing on growth and innovation, Ken Miller has gained deep insight into the unique challenges of leadership. While technologies and industries continue to evolve, he believes the solutions to these challenges are consistently found in the same place: people. His passion lies in building empowered teams and cultivating leadership, helping individuals understand the powerful connection between personal growth, innovation, and high performance.

LinkedIn

Key Topics

• The Value Angel Investors Bring Beyond Capital

• Minority Stakeholders: Influence Without Control

• Board Dynamics and Effective Questioning

• Approaching Disengaged Founders and Boards

• Building Consensus and Escalating Concerns

• Navigating Differing Investor Philosophies

• Recognizing When Influence Isn’t Working

Connect

Mike Kelly

• LinkedIn

• Website

• Developer Town

Ben Pidgeon

• LinkedIn

• VisionTech

Jacob Schpok

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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.