In The Trenches

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During my ~10 years as a searcher and CEO, I had an endless number of commercial problems and opportunities that required my attention at any given time. However, it was often the personal considerations that kept me up at night: I rarely lost sleep over whether to raise prices by 5% or 15%, but instead was kept awake by the idea that even asking the question suggested that I didn’t truly know what I was doing. I wasn’t anxious about what mix of equity and debt to include in a letter of intent, but was instead anxious about the prospect of not finding a company to acquire at all after spending two years in pursuit of one.

For this reason, I thought it might be helpful to compile some of the lessons that I’ve learned over the years that cover the “human side” of acquisition entrepreneurship. I hope at least one of them provides you with a reason to reflect on your own situation, and perhaps make a change for the better in the process.

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

It is also my experience that many problems that seem to be attributable to the engineering group (technical debt, high levels of customization, regularly missing deadlines, etc.) are actually product management problems masquerading as development problems. This episode, originally published in 2021, is as applicable today as it was then.

My guest today is Rich Mironov, who is North America's preeminent Product Management thought leader. He has spent 40 years in the software industry in numerous capacities, and currently acts as a Coach, Consultant, and Interim Executive for CEOs and Heads of Product across Canada and the United States, advising them on a diverse range of issues spanning product, marketing, engineering, and sales. Rich has led Product Management at six software companies, and has now consulted for more than 170 technology businesses of all sizes. He is the author of "Product Bytes", a hugely popular and long-running blog on software, start-ups, product strategies, Silicon Valley, and the inner life of product managers. Our conversation covers hiring a Product leader and Product team, how to think about prioritizing products/features/functions, how Product should interface with Sales and other internal departments, how involved CEOs should be in Product, and what fatal mistakes he’s seen Product Managers make.

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

Though it is correct to suggest that all acquisitions are funded through some combination of cash-on-hand, debt, or equity, it’s also a bit of an oversimplification. Indeed, the financing options available to prospective acquirors are numerous, and in today’s blog post, I focus specifically on debt, and evaluate the four most common sources of leverage used to finance the purchase of small and medium-sized businesses. These include bank debt, mezzanine debt, seller financing, and SBA loans.

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

I recently published a blog post, Why You May Want to Reconsider Your Industry Roll-up Strategy, within which I detailed many of the ways in which consolidation strategies can go wrong. In today’s episode, I want to look at the opposite side of that coin and dig deeply into an instance where a consolidation strategy went very right.

I'm joined today by Jay Davis & Jason Pananos, who, after graduating from business school in 2008, acquired Vector Disease Control, a company that they grew from ~$7M to ~$50M in revenue in ~7 years through successfully executing on 14 bolt-on acquisitions.

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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

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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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.

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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.

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, CEO, and best-selling author, Rob Dube. In 1991, Rob co-founded imageOne,

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").