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

My Guests 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. In 2017 they also co-published the widely readContinue reading “Royce Yudkoff & Rick Ruback: Educators, Mentors, and Leaders Within the SMB Community”

Jeff Stevens & A.J. Wasserstein on The Future of Entrepreneurship Through Acquisition

My Guests A.J. Wasserstein is the Eugene F. Williams, Jr. Lecturer in the Practice of Management at the Yale School of Management. His research, writing, and teaching concentrates on search funds, entrepreneurship, programmatic acquisitions, and small businesses. In addition to his role as an educator, A.J. is also a private investor in lower middle-market businesses.Continue reading “Jeff Stevens & A.J. Wasserstein on The Future of Entrepreneurship Through Acquisition”

Michael Girdley on The Rise of Holding Companies

My Guest Michael Girdley is an entrepreneur and investor who has spent the past 30 years building a personal holding company boasting over $100M in annual revenue, comprised of 12 businesses across software, technology, consumer retail, and education, among others. Outside of managing his holding company, Michael is deeply involved in the North American SMBContinue reading “Michael Girdley on The Rise of Holding Companies”

Questions You Should Be Prepared to Answer Before Buying (or Selling) a Small Business

Listen to this Blog Post It likely goes without saying that every transaction is different: Every company, industry, searcher, and investment opportunity presents unique considerations that in turn give rise to unique questions and areas for further due diligence. With that said, over many years of evaluating countless acquisition targets alongside searchers, I’ve found thatContinue reading “Questions You Should Be Prepared to Answer Before Buying (or Selling) a Small Business”

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”

The 2023 SaaS CEO Survey

Listen to this Blog Post The Data Set The year in which each target company was acquired is detailed in the chart to the right. As can be seen, we were able to achieve reasonably good diversity by vintage year, with 18 of the 41 transactions taking place in 2019 or earlier, and 23 ofContinue reading “The 2023 SaaS CEO Survey”

Are You Selling to the Wrong Customers?

Listen to this Blog Post In my experience, among the countless strategic decisions that software CEOs must make, the decision of which end markets to serve doesn’t seem to command the time, attention, and level of thoughtfulness that it probably should. Leaders who run mature and established companies often take comfort in the product/market fitContinue reading “Are You Selling to the Wrong Customers?”

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”

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”