86 episodes

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.

In The Trenches Steve Divitkos

    • Business
    • 5.0 • 16 Ratings

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.

    The Constellation Software Playbook for Acquiring and Growing Software Companies

    The Constellation Software Playbook for Acquiring and Growing Software Companies

    This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses⁠⁠⁠⁠⁠⁠⁠⁠⁠





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    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





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    Constellation Software is one of the world's most widely followed and admired software companies, having acquired upwards of 500 lower-middle-market software companies since its founding in 1995. Our guest today, Mike Dufton, is the CEO of the Volaris group, one of the six major operating units within Constellation, that itself owns upwards of 200 portfolio companies.

    • 1 hr 17 min
    Evaluating Stock Options as Attraction, Retention, and Incentive Alignment Tools

    Evaluating Stock Options as Attraction, Retention, and Incentive Alignment Tools

    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





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    This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses⁠⁠⁠⁠⁠⁠⁠





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    After many years of using company stock options as attraction, retention, and incentive alignment tools, I’ve come to appreciate their merits, risks, and possible alternatives. I intend to share these lessons with you today. More specifically though, I will argue that while options do have their time and place, there are often much simpler and less expensive alternatives that arguably have a greater impact on attraction, retention, and incentive alignment.

    • 22 min
    Can Ambition and Inner Peace Coexist? With Rob Dube

    Can Ambition and Inner Peace Coexist? With Rob Dube

    This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses⁠⁠⁠⁠⁠⁠⁠⁠





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    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





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    Today I'm joined by entrepreneur, CEO, and best-selling author, Rob Dube. In 1991, Rob co-founded imageOne,
    a managed print services business based in Oak Park, Michigan, that has won countless awards across countless publications for it’s growth, culture, and employee engagement, among many other accolades.

     

    Today we discuss Rob's newest book, Shine: How Looking Inward Is the Key to Unlocking True Entrepreneurial Freedom. This book is all about how CEOs can manage their inner worlds, which stands in stark contrast to most business books, that focus almost exclusively on how CEOs can manage their outer-worlds. Rob co-authored the book alongside Gino Wickman, who is the author of the widely-read Traction, the book that introduced the world to the Entrepreneurial Operating System ("EOS").

    • 1 hr 26 min
    Answers to Recurring FAQs from Current and Prospective Searchers

    Answers to Recurring FAQs from Current and Prospective Searchers

    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





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    This episode is brought to you by ⁠⁠⁠⁠⁠⁠The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses⁠⁠⁠⁠⁠⁠





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    Many searchers understandably tend to have very similar questions and areas of uncertainty. Indeed, in most instances, I had these very same questions and areas of uncertainty myself prior to raising my own search fund in 2012. As a result of the frequency with which I'm asked these questions, I've presented each of them in today's episode, and have also included my opinion on what the answers may be. Some of the questions include:


    Constructing a cap table
    Differences between the Canadian and US search ecosystems
    Is the search fund market too crowded/saturated
    The trade-off between price and business quality
    What the best searchers do in their first 3-6 months
    Proprietary vs. brokered deal flow generation
    When to visit a prospective seller
    Success rates of industry agnostic searches
    Having an industry & geographic focus
    Homogeneity among search investors re: industry preferences
    How to spend your first week as a new CEO
    Should I create a 100-day plan?
    How to communicate the ownership change to customers

    • 44 min
    Profit Before Anything Else: With Mike Michalowicz, Author of "Profit First"

    Profit Before Anything Else: With Mike Michalowicz, Author of "Profit First"

    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




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    This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses⁠⁠⁠⁠⁠⁠⁠⁠




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    Today I'm joined by Entrepreneur, Investor, and Author Mike Michalowicz. In addition to being the author of 9 books, Mike is himself a serial entrepreneur, having founded, operated, and successfully exited several companies across his multi-decade career. He now spends much of his professional time writing, speaking, and coaching CEOs and entrepreneurs on the various systems that helped make him successful, including (and especially) his "Profit First" system, a highly tactical guide to organizing your entire company around achieving endurable profitability.

    • 1 hr 19 min
    Royce Yudkoff & Rick Ruback: Educators, Mentors, and Leaders Within the SMB Community

    Royce Yudkoff & Rick Ruback: Educators, Mentors, and Leaders Within the SMB Community

    This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses⁠⁠⁠⁠⁠⁠⁠




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    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




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    Today I am thrilled to be joined by two guests that, without the risk of hyperbole, have changed my life in more ways than I can count. Royce Yudkoff & Rick Ruback are both professors at the Harvard business school, and co-teach two wildly popular courses called “The Financial Management of Smaller Firms” and “Entrepreneurship through Acquisition”, both of which focus on how to acquire, finance and operate your own smaller firm. They also co-published the widely read book, The HBR Guide to Buying a Small Business, published by Harvard Business Review Press, which acts as the definitive source of wisdom and guidance for a countless number of acquisition entrepreneurs

    • 1 hr 2 min

Customer Reviews

5.0 out of 5
16 Ratings

16 Ratings

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