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”

Brent Beshore: The “Forrest Gump of Private Equity”

My Guest My guest today is Brent Beshore, Founder and CEO of Permanent Equity, a private investment firm that invests in Founder-owned private companies. Permanent Equity is a long-term investor that typically intends to hold portfolio companies indefinitely, often without the use of any leverage. In addition to his role as an investor, Brent isContinue reading “Brent Beshore: The “Forrest Gump of Private Equity””

A.J. Wasserstein: Reflections of a Founder, CEO, Investor and Educator

My Guest My guest today is A.J. Wasserstein, 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 inContinue reading “A.J. Wasserstein: Reflections of a Founder, CEO, Investor and Educator”

Sell-Side M&A Advisors: How to Choose One, How Much They Cost, and The Importance of the “Fine Print”

My Guest John Carvalho is the President of Stone Oak Capital, an M&A advisory firm that focuses exclusively on middle market businesses, with a specific focus on transactions between $10 and $100 million. Among other things, Stone Oak offers acquisition, divestitures, corporate finance and valuations services for its clients. John is also the Founder ofContinue reading “Sell-Side M&A Advisors: How to Choose One, How Much They Cost, and The Importance of the “Fine Print””

Strategic Considerations When Evaluating a Letter of Intent to Sell Your Business

Listen to This Blog Post For many business owners (particularly those actively looking to sell their companies), few things are as exciting as receiving a Letter of Intent (“LOI”) from a prospective purchaser. Beyond the sense of personal validation stemming from the fact that a sophisticated counterparty sees an asset worth paying for, many businessContinue reading “Strategic Considerations When Evaluating a Letter of Intent to Sell Your Business”