Listen to This Blog Post Over the past few months, I’ve been presented with five separate opportunities that contemplated the acquisition of a company with $7M or more of EBITDA (this compares to the Search Fund average of $2.2M for the 2022-2023 cohort of Searchers). While I acknowledge that five data points don’t constitute aContinue reading “Are Search Funds Moving Up Market?”
Author Archives: sdivitkos
The Four Stages of Leadership Maturity: Why the CEO Must Change Before the Company Can
My Guest Jenner Garvey Berger is the Co-Founder and CEO of Cultivating Leadership, a firm that utilizes tools from history, psychology, business and neuroscience to help leaders grow and evolve over time. The firm offers custom programs, one-on-one coaching, and organizational development initiatives to companies across various industries and size ranges. Jennifer is also theContinue reading “The Four Stages of Leadership Maturity: Why the CEO Must Change Before the Company Can”
“Don’t F*ck It Up”: Les Trachtman on Avoiding Post-Close Founder Succession Mistakes
My Guest Les Trachtman is a seasoned entrepreneur, educator, and author with over four decades of experience in strategy, consulting, and start-ups. Les is also an adjunct instructor at the Johns Hopkins University Carey Business School, where he shares his years of experience and insights with the next generation of business leaders. He is aContinue reading ““Don’t F*ck It Up”: Les Trachtman on Avoiding Post-Close Founder Succession Mistakes”
Why Most Incentive Plans Fail—and How Thoughtful CEOs Get Them Right
My Guest I’m joined this week by Stacey Carroll, who 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 anContinue reading “Why Most Incentive Plans Fail—and How Thoughtful CEOs Get Them Right”
Installing an Operating System in Your Business: Lessons from Real EOS Implementations
My Guest 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 (or “the Entrepreneurial Operating System”) in my own company beginning in 2015, and we continued toContinue reading “Installing an Operating System in Your Business: Lessons from Real EOS Implementations”
Hard to Kill: A Four-Part Framework for Evaluating Small Business Acquisitions
Listen to This Blog Post I would make the world’s worst Venture Capitalist. If you don’t believe me, keep reading. As I’ve transitioned from operator to investor over the past 5 years or so, I’ve attempted to develop (and have attempted to articulate below) a general philosophy to guide my decision making, given that almostContinue reading “Hard to Kill: A Four-Part Framework for Evaluating Small Business Acquisitions”
Facing the Worst-Case Scenario: How Jed Morris Lost His Business and Rebuilt His Life
My Guest Jed Morris is the Founder and Managing Partner of Sunset Coast Capital, where he leads investments in U.S.-based aerospace and defence businesses. He specializes in helping acquisition entrepreneurs and independent sponsors navigate the complexities of small business ownership, diligence, and operator readiness. Jed’s career began in the U.S. Air Force, where he heldContinue reading “Facing the Worst-Case Scenario: How Jed Morris Lost His Business and Rebuilt His Life”
How A.I. is Transforming the Acquisition and Operations of Small Businesses
My Guest You are likely aware of how much AI has already changed how we live and how we work. You’re probably also aware – at least vaguely – of how much it will continue to change the way that we live and work over the coming months and years. The process of searching for,Continue reading “How A.I. is Transforming the Acquisition and Operations of Small Businesses”
Technical Debt: What it is, How Much of it You Can Live With, and How to Incorporate it into an Investment Thesis
My Guest 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). HeContinue reading “Technical Debt: What it is, How Much of it You Can Live With, and How to Incorporate it into an Investment Thesis”
Stress, Panic Attacks, Debilitating Anxiety, and a $170M Exit: iContact Founder Aaron Houghton
My Guest Aaron Houghton started his first business at age 17, and since then he has built and launched more than ten technology startups, scaling one to 350 employees and $50M in annual subscription revenue. He has sold two companies to private buyers and one to a publicly traded company for $169M before his 30thContinue reading “Stress, Panic Attacks, Debilitating Anxiety, and a $170M Exit: iContact Founder Aaron Houghton”