In The Trenches

Steve Divitkos
  • 5.0 (16)
  • ENTREPRENEURSHIP
  • UPDATED BIWEEKLY

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. 12/23/2025

    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

  2. 12/11/2025

    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

  3. 11/27/2025

    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

  4. 11/13/2025

    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

  5. 10/30/2025

    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

  6. 10/22/2025

    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.

    1 min

  7. 10/16/2025

    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.

    1h 18m

  8. 10/02/2025

    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.

    1h 20m
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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 - 2025
  • Episodes
    130
  • Rating
    Clean
  • Copyright
    © Steve Divitkos
  • Show Website
    In The Trenches

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