In The Trenches

Dr. Jim Schleckser, founder of The CEO Project and author of Great CEOs Are Lazy, advises high-growth leaders on leverage, delegation, and strategy. He discusses peer groups, diagnosing priorities, hiring pitfalls, and what high-leverage CEO work looks like. Short-term wins versus long-term assets, when to attend meetings, and the psychology behind micromanagement also come up.

Discussion about whether small-firm buyers are pursuing larger, middle-market companies. Talks cover risks of moving upmarket like complexity, higher multiples, and cap table issues. Summarizes a 50-person survey on target company size and current preference trends. Considers advantages of bigger deals such as deeper management, lending options, and economics, plus potential impacts on the broader ETA ecosystem.

Jennifer Garvey Berger, leadership expert and author who studies adult development, outlines four predictable stages of leadership maturity. She discusses the emotional surprises of leading, why knowing your stage matters, how to self-diagnose, common sticking points for high performers, and practical habits to accelerate growth.

Les Trachtman, seasoned entrepreneur and author of Don't F**k It Up, shares hard-won lessons from four decades of taking over founder-led companies. He discusses how to manage the founder-successor relationship, crafting practical transition agreements, using short mutual renewals as an off-ramp, assessing who to keep or replace, and the value of patience and tactical communication during the handoff.

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!

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!

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.

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.

Jed Morris, an entrepreneur who endured a business bankruptcy and rebuilt his life, shares hard-won perspective. He covers risky friends-and-family funding, why roll-ups can fail, cultural and cash-flow traps, and the fallout of personal guarantees. Short, candid stories trace his collapse, recovery, and how he now advises others to avoid the same mistakes.

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.