In The Trenches

Steve Divitkos
undefined
Jan 20, 2026 • 1h 3min

Why Most Incentive Plans Fail—and How Thoughtful CEOs Get Them Right

Join Stacey Carroll, an HR leader and compensation specialist with decades of experience, as she explores the intricacies of incentive plans for businesses. Discover why many plans fail, from the pitfalls of complexity to the importance of aligning individual and company goals. Stacey emphasizes the power of simple, objective metrics and meaningful communication. She also discusses the significance of personalized rewards over cash incentives and shares strategies for managing inherited pay inequities. Tune in for insights that can transform your compensation strategy!
undefined
30 snips
Jan 8, 2026 • 56min

Installing an Operating System in Your Business: Lessons from Real EOS Implementations

In this insightful discussion, Alex Hodgkin, an entrepreneur and EOS implementer, shares his journey of implementing the Entrepreneurial Operating System in his own company. He highlights the advantages of EOS for small businesses, contrasting it with other frameworks like Scaling Up. Alex emphasizes the importance of strong leadership buy-in, effective communication, and comprehensive implementation. He also discusses common challenges and how aligning with technology can enhance the adoption of EOS. Discover how to navigate the complexities of operating systems from a seasoned implementer!
undefined
Dec 23, 2025 • 14min

The Working Capital Adjustment

This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Oberle Risk Strategies⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ *This episode is brought to you by ⁠⁠⁠⁠B⁠⁠⁠⁠⁠⁠⁠⁠⁠oulay, the industry standard for Quality of Earnings, tax, and audit services, serving search fund entrepreneurs for 20+ years⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠*The Working Capital Adjustment is part of substantially every M&A transaction, yet it is the calculation (and concept) with which most business owners remain largely unfamiliar. Without a proper understanding of what the working capital adjustment is, why it's necessary, and ways in which it can be manipulated, business owners risk leaving a lot of money on the table when dealing with a more sophisticated and experienced counterpart (even AFTER the sale of their business is already complete). If you don't like the idea of having to wire money back to your buyer after they've wired you the money to purchase your company, then this episode is for you.
undefined
9 snips
Dec 11, 2025 • 21min

Hard to Kill: A Four-Part Framework for Evaluating Small Business Acquisitions

Dive into the complexities of small business acquisitions with a unique four-part framework that aims to clarify investment decisions. Explore the concept of asymmetry—where potential upside outweighs downside. Discover the importance of avoiding existential risks, like customer concentration. Learn why protecting the downside is crucial, and see examples of resilient companies ideal for first-time CEOs. Plus, gain insights from real-world success stories that exemplify this investment philosophy.
undefined
Nov 27, 2025 • 1h 29min

Facing the Worst-Case Scenario: How Jed Morris Lost His Business and Rebuilt His Life

This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Oberle Risk Strategies⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠  *This episode is brought to you by ⁠⁠⁠B⁠⁠⁠⁠⁠⁠⁠⁠⁠oulay, the industry standard for Quality of Earnings, tax, and audit services, serving search fund entrepreneurs for 20+ years⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠*Today’s guest, Jed Morris, has been incredibly generous, vulnerable, and forthright about the challenges that he faced as a Searcher and CEO. In his own words, after the bankruptcy of his company, he experienced homelessness, a profound sense of shame and failure, and nearly lost his marriage. Since then, however, his courage has helped an untold number of entrepreneurs either persist through similar circumstances, or avoid them entirely. To me, Jed is somebody who demonstrates and embodies what true leadership looks like.The point of today’s conversation is not necessarily to scare people away from taking this path, nor to suggest that Jed's outcome is necessarily likely to happen to you. Instead, what I took from this conversation is the fact that, sometimes, even the worst case scenario is still one that we can not only survive, but learn from, grow from, and share with others.
undefined
Nov 13, 2025 • 1h 1min

How AI is Transforming the Acquisition and Operations of Small Businesses

Geoff Woods, author of The AI-Driven Leader and former Chief Growth Officer at Jindal Steel, discusses how AI is reshaping small business acquisition and operations. He shares insights on assessing AI risk versus opportunity and the resistance industries like law and accounting face. Geoff reveals how to leverage AI for legacy businesses and highlights the importance of leaders personally engaging with AI. He also introduces practical techniques like CRIT prompts and using AI for simulating advisory scenarios. His views on future AI impacts and guiding the next generation are equally enlightening.
undefined
Oct 30, 2025 • 1h 26min

Technical Debt: What it is, How Much of it You Can Live With, and How to Incorporate it into an Investment Thesis

In this engaging discussion, Chris Smith, Managing Partner at Spellbound Partners with over 25 years in software development, explores the elusive concept of technical debt. He reveals how shortcuts can lead to significant business problems and outlines common pitfalls in software companies. Chris underscores the necessity of thorough due diligence for acquirers, providing strategies for assessing and managing technical debt. With insights on hiring and growth, he highlights the importance of aligning tech strategies with investment theses.
undefined
Oct 22, 2025 • 1min

Announcing the Launch of Mineola Fund II

In 2022, we launched Mineola’s first fund to help entrepreneurs navigate the tactical, commercial, and personal challenges that are an inevitable part of the acquisition entrepreneurship journey. Almost four years later, we’re excited to continue this work through Mineola Fund II. Playing a small role in helping people realize their entrepreneurial dreams has proven to be an incredibly fulfilling way to spend my professional life. I hope to be able to do this very same thing for many more years to come.
undefined
Oct 16, 2025 • 1h 18min

Stress, Panic Attacks, Debilitating Anxiety, and a $170M Exit: iContact Founder Aaron Houghton

This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Boulay, the industry standard for Quality of Earnings, tax, and audit services, serving search fund entrepreneurs for 20+ years⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠*This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Oberle Risk Strategies⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠  *  Aaron Houghton is a serial entrepreneur, having launched more than 10 companies in his career, with the most famous arguably iContact, an email and marketing automation tool that he sold for $170M prior to his 30th birthday. Among countless other accolades, Aaron was selected as an E&Y Entrepreneur of the Year in 2008, and was listed to Inc Magazine's 30 Under 30 list in 2010. He now spends his time running Dory, a company that helps high performers under high levels of stress optimize their performance.In Aaron's words, his "success came with the hidden costs of long-term stress including panic attacks, debilitating anxiety, burnout, and mental breakdown”. We dig into the psychological realities of entrepreneurship quite deeply in our discussion today, and discuss how his struggles led to a five-year study of how entrepreneurs manage stress, and the tools & techniques they can utilize for achieving high performance while maintaining mental and physical health.
undefined
Oct 2, 2025 • 1h 20min

Rob Markey: Creator of the Net Promoter Score and Founder of Bain's Global Customer Strategy Practice

This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Oberle Risk Strategies⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠  *This episode is brought to you by ⁠⁠⁠B⁠⁠⁠⁠⁠⁠⁠oulay, the industry standard for Quality of Earnings, tax, and audit services, serving search fund entrepreneurs for 20+ years⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠*Rob Markey is the creator of the Net Promoter Score ("NPS"), which has grown to become the de facto metric for measuring the health, loyalty and satisfaction of a customer base. He is also a longtime Partner at Bain & Company, where he founded and leads their Global Customer Strategy practice.Rob is the co-author of The Ultimate Question 2.0: How Net Promoter Companies Thrive in a Customer-Driven World, a New York Times and Wall Street Journal bestseller. Rob also teaches at Harvard Business School, and serves on several nonprofit and corporate boards, where he helps leaders build customer‑centric businesses.

The AI-powered Podcast Player

Save insights by tapping your headphones, chat with episodes, discover the best highlights - and more!
App store bannerPlay store banner
Get the app