In The Trenches

Steve Divitkos
  • 5.0 (19)
  • ENTREPRENEURSHIP
  • UPDATED SEMIMONTHLY

The only podcast dedicated exclusively to Entrepreneurs and CEOs running Small to Medium Sized Businesses (SMB). Nobody knows what it’s like to be an Entrepreneur or CEO unless you’ve been one. Though many understand the rewards of company leadership, very few understand the arduous journey that’s required to get (and stay) there. I share my own lessons as an Entrepreneur and CEO, and interview experts spanning Sales, Leadership, Mental Health, M&A, and Operations (among others) all with a single goal: To improve the personal and professional lives of Entrepreneurs and CEOs running SMBs.

  1. FEB 5

    “Don’t F*ck It Up": Les Trachtman on Avoiding Post-Close Founder Succession Mistakes

    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     *   When assuming the leadership role of a company that was previously held by its original Founder, new CEOs are often surprised at how difficult it can be to properly manage that relationship. A non-functional relationship between the incoming and outgoing owners can divide the employee base, create confusion about who to approach with problems and opportunities, and can limit critical transfers of knowledge and relationships that incoming CEOs typically require. Incoming owners often themselves in a bit of an awkward position during their first few months on the job: On one hand, they've likely just spent many months slogging through a protracted purchase process with the seller that was likely filled with contentious negotiations and several emotional disagreements. Yet on the other hand, almost immediately upon the closing of that acquisition, new CEOs will likely find themselves meaningfully in need of the help, knowledge and experience that only the person from whom they purchased the business can provide. In other words: Upon closing, what the seller wants from the buyer (mostly transaction proceeds) has already been received. What the buyer wants of the seller (help, knowledge transfer, introductions, and so on), hasn’t even yet begun. To help us better understand how to manage this critical hand off process, I was joined this week by Les Trachtman, Author of “Don't F**k It Up: How Founders and Their Successors Can Avoid the Clichés That Inhibit Growth”. Les is a seasoned entrepreneur, educator, and author with over four decades of entrepreneurial experience. He is also an adjunct instructor at the Johns Hopkins University Carey Business School, and is a frequent guest lecturer at Harvard Business School, MIT and other academic institutions, where he often talks to students about the unappreciated nuances of Founder succession.

    1h 18m

  2. JAN 20

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

    I suspect that the CEOs in our audience are likely to agree that crafting a truly effective incentive compensation plan is simultaneously one of the most difficult, and one of the most important, tasks that a small business CEO will face. Charlie Munger is famous for saying “Never, ever think about something else when you should be thinking about the power of incentives.” He's also said “I think I’ve been in the top 5% of my age cohort, all my life, in understanding the power of incentives, and all my life I’ve underestimated them.” But why is it so difficult to craft a truly effective incentive plan? Based on many years of experience putting them together myself, here are just a few of the challenges that I faced: Avoiding unintended consequences and people "gaming" the systemHow to balance individual goals vs. company goals vs. departmental goalsHow to incent people on company goals when the achievement of those goals falls largely outside of their controlIf or how to change a comp plan if circumstances change materially within any given yearHow to manage changes in goals & targets across any two given yearsThe balance between simplicity & detailHow to handle inherited employees whose salaries may fall outside of company-wide pay bands To help me untangle each of these challenges, this week I'm joined by Stacey Carroll. Stacey has spent substantially her entire career leading HR organizations across a wide array of companies, with a specific focus on compensation & benefits. She has also spent the past 14 years leading HR Experts on Call, a company she founded where she acts as an interim HR leader for small and medium-sized businesses.

    1h 3m

  3. JAN 8

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

    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     *   Over the past handful of years, there has been substantial growth in the number of companies who have decided to implement formal “operating systems” to govern certain strategic and operational decisions within their businesses. I implemented EOS (short for “the Entrepreneurial Operating System”) in my own company beginning in 2015, and we continued to operate under its various principles and structures until successfully selling the company in late 2020. Based on that first-hand experience, I thought it would be worthwhile to dig into a number of recurring FAQs that I often receive from other CEOs who are considering implementing an operating system within their own companies. To help me work through these FAQs, I was joined by Alex Hodgkin. In addition to being an entrepreneur and CEO himself, Alex also co-founded the Entrepreneurship Through Acquisition program at the University of Chicago’s Booth School of Business. Currently, Alex runs his own business specifically to help small business CEOs implement the Entrepreneurial Operating System.

    56 min

  4. 2025-12-23

    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.

    14 min

  5. 2025-12-11

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

    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     *   As I’ve transitioned from operator to investor over the past 5 years or so, I’ve attempted to develop a general philosophy to guide my decision making, given that almost every investment decision seems to present me with a long list of reasons to be simultaneously hopeful and terrified. The four-point framework that I present in today's episode is my attempt to add some structure and objectivity to these decisions. I’m not so vain as to think that my investment philosophy is one that ought to be emulated or studied by others (quite the opposite, in fact: I am a work-in-progress at best, and a complete novice at worst). Instead, I’ve decided to present this framework in hopes that: Searchers might benefit from it as they evaluate potential investment targets without the years of context and hundreds of repetitions that are typically required to calibrate a sense of an attractive opportunity vs. a less attractive oneTo keep myself honest, and to create a single place for me to go whenever I feel like I may be deviating from an investment philosophy that makes intuitive sense to me Please enjoy!

    21 min

  6. 2025-11-27

    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.

    1h 29m

  7. 2025-11-13

    How AI is Transforming the Acquisition and Operations of Small Businesses

    This episode is brough to you by System Six, an outsourced finance, accounting, and tax partner to over 300 businesses nationwide * 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     *   The process of searching for, acquiring, and operating a small business is changing. Those who don’t know how to leverage the power of AI may find themselves quickly falling behind those who do. Joining me today is Geoff Woods, author of The AI-Driven Leader, currently one of the fastest growing and best-selling AI books in the world. Prior to writing the book, Geoff was the Chief Growth Officer of Jindal Steel & Power, where he drove market cap growth from $750M to $12B in four years through AI-driven leadership.

    1h 1m

  8. 2025-10-30

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

    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 * Chris Smith is the Managing Partner of Spellbound Partners, a a company that helps acquirors with technical due diligence, fractional CTO services, and outsourced development services, among other things. Chris has over 25 years of experience building software platforms, and is an expert in cloud computing and software as a service (SaaS). He has been a part of numerous founding startup teams and has led multiple teams through high-growth transitions. Much of what we discuss today is intended to uncover how much “technical debt” any given target company may possess within its code base. Though substantially every software company has some amount of technical debt, those that are weighed down by an asymmetric burden of it tend to experience very real business problems that non-technical acquirors and CEOs may not fully appreciate. As a result, prospective acquirors would be well served to thoroughly diligence the amount of technical debt possessed by any given target company, and proceed very carefully (or perhaps not proceed at all) with those companies who seem to possess much more than their fair share of it.

    1h 26m
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Ratings & Reviews

5
out of 5
19 Ratings

About

The only podcast dedicated exclusively to Entrepreneurs and CEOs running Small to Medium Sized Businesses (SMB). Nobody knows what it’s like to be an Entrepreneur or CEO unless you’ve been one. Though many understand the rewards of company leadership, very few understand the arduous journey that’s required to get (and stay) there. I share my own lessons as an Entrepreneur and CEO, and interview experts spanning Sales, Leadership, Mental Health, M&A, and Operations (among others) all with a single goal: To improve the personal and professional lives of Entrepreneurs and CEOs running SMBs.

Information

  • Creator
    Steve Divitkos
  • Years Active
    2021 - 2026
  • Episodes
    133
  • Rating
    Explicit
  • Copyright
    © Steve Divitkos
  • Show Website
    In The Trenches

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