Venture Capital “Orphans”: Exploring an Emerging Search Fund Investment Thesis

Listen to this Blog Post Since their inception in 1984, Search Funds have largely targeted a very particular profile of company: Targets tend to be mature, enduringly profitable businesses with recurring revenue profiles, low capital requirements, and straight-forward operations. These businesses are often still run by their founders, and these founders tend to be laterContinue reading “Venture Capital “Orphans”: Exploring an Emerging Search Fund Investment Thesis”

Lessons Learned From 400+ Post-Exit Entrepreneurs: John Warrillow, Host of Built to Sell Radio

My Guest My guest today is John Warrillow, author of the bestselling book Built to Sell: Creating a Business That Can Thrive Without You, and Founder & CEO of The Value Builder System, a sales and marketing software tool for business advisors to find, win and keep their best clients. Built to Sell was recognizedContinue reading “Lessons Learned From 400+ Post-Exit Entrepreneurs: John Warrillow, Host of Built to Sell Radio”

When Search Funds Don’t Go As Planned (Part 2): Trends & Observations With Jim Sharpe

My Guest My guest today is Jim Sharpe, somebody who I’ve been fortunate enough to call a mentor and friend for over 10 years now. This is Jim’s second appearance on In The Trenches (you can access the first episode here) In this week’s episode, we build upon the first-hand accounts presented in episode 1Continue reading “When Search Funds Don’t Go As Planned (Part 2): Trends & Observations With Jim Sharpe”

When Search Funds Don’t Go As Planned (Part 1): 3 Searcher Case Studies

My Guests If one were to attend a randomly selected group of Search Fund conferences, they’d be forgiven for thinking that every search fund is a smashing success. When I was both a searcher and a CEO, I often left these types of events with a certain sense of insecurity and self-doubt, as everybody seemedContinue reading “When Search Funds Don’t Go As Planned (Part 1): 3 Searcher Case Studies”

The State of Lower-Middle Market Credit: Two Major Bank Failures, Rising Interest Rates, and a Looming Recession

My Guests To say that it’s been an active 6-18 months in the banking sector would be an understatement: Beginning as recently as January, 2022, we’ve seen the US Federal Funds rate increase from .08% to 4.83%, which, at least in part, precipitated the rapid collapse of Silicon Valley Bank, and the rescue of FirstContinue reading “The State of Lower-Middle Market Credit: Two Major Bank Failures, Rising Interest Rates, and a Looming Recession”

The Merits, Risks, and Possible Unintended Consequences of Earn-Outs

Listen to this Blog Post When acquiring small to medium sized businesses, buyers often utilize a tool called an “earn-out”, which is a form of contingent consideration that sellers may receive at some point in the future in addition to the cash that they stand to receive at closing. Though earn-outs can be useful andContinue reading “The Merits, Risks, and Possible Unintended Consequences of Earn-Outs”

The Smallest Changes That Had the Largest Impacts: 4 CEO Case Studies

My Guests This is a very special episode of In The Trenches: In today’s episode, I will be interviewing 4 different CEOs of 4 different SMBs, and asking them just a single question: “What are some of the seemingly small changes you’ve made that have had the largest impacts?” When taking over a new business,Continue reading “The Smallest Changes That Had the Largest Impacts: 4 CEO Case Studies”

Mike Zani, CEO of The Predictive Index: Hiring, Personality Profiling Tools, Working with a Partner, and Other Lessons from 20 Years as a CEO

My Guests My guest today is Mike Zani, CEO of The Predictive Index. The Predictive Index serves more than 9,000 clients across 142 countries, helping businesses optimize their hiring and team composition decisions through a combination of behavioral science, software, and professional consulting from the world’s top workplace behavior specialists. Mike has been CEO ofContinue reading “Mike Zani, CEO of The Predictive Index: Hiring, Personality Profiling Tools, Working with a Partner, and Other Lessons from 20 Years as a CEO”

The Current State of the Debt Capital Markets

My Guests My guests today are Cory Kaiser and Timothy Eaton, Vice President & Associate Vice President respectively within TD’s Commercial Banking Group. Between them, they have over 40 years of experience lending to lower-middle market businesses not just to finance their acquisitions, but also to finance growth initiatives, day-to-day working capital needs, and leveragedContinue reading “The Current State of the Debt Capital Markets”

Evaluating 5 Very Different Approaches to Acquiring a Software Company

Listen to This Blog Post Enterprise software is considered to be among the world’s best business models, and for good reason: Revenue tends to be highly recurring. Switching costs, pricing power and customer retention rates are often high. And businesses have the ability to scale in a non-linear fashion owing to the fact that additionalContinue reading “Evaluating 5 Very Different Approaches to Acquiring a Software Company”