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”
Author Archives: sdivitkos
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”
Rob Markey: Creator of the Net Promoter Score and Founder of Bain’s Global Customer Strategy Practice
My Guest Rob Markey is the creator of the widely-used Net Promoter Score (“NPS”) system. Rob also leads the NPS Loyalty Forum, a group of 35 senior executives from loyalty-leading companies around the world, such as The Vanguard Group, American Express, JetBlue, TD Bank, LEGO, Progressive Insurance, PwC and Intuit. He is also the co-authorContinue reading “Rob Markey: Creator of the Net Promoter Score and Founder of Bain’s Global Customer Strategy Practice”
Building Better CEOs: Lessons From a Veteran Executive Coach
My Guest Sherman Black is an executive coach that specializes in working with CEOs running small and medium-sized businesses. His coaching practice, at least in part, is based on over 35 years of experience leading and transforming companies himself. Among other things, Sherman spent 15 years as a technology CEO across public and private companies,Continue reading “Building Better CEOs: Lessons From a Veteran Executive Coach”
Evaluating Customer Retention in Recurring Revenue Businesses: With Craig Zingerline
My Guest Craig Zingerline is a serial entrepreneur currently working as the CEO of Growth Minded, a company that helps startups and other technology companies scale their growth and retention strategies. Prior to Growth Minded, he founded Velocity Growth and scaled to 7-figures of ARR, was Chief Product Officer at Sandboxx, and the Head ofContinue reading “Evaluating Customer Retention in Recurring Revenue Businesses: With Craig Zingerline”
Rethinking Asset Intensity in Search Fund Acquisitions
Listen to this Blog Post The vast majority of Search Funds seek to acquire businesses that are both “asset-light” and “capital-light”. That is, companies that don’t have a large base of tangible assets that need to be added to, refurbished, or replaced to either maintain operations or pursue growth. All else being equal, this makesContinue reading “Rethinking Asset Intensity in Search Fund Acquisitions”