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 in lower middle-market businesses. He was the President of Onesource Water, the third-largest bottleless water service business in the U.S., which was sold to Water Logic, a U.K.-based strategic acquirer, in 2016. Previously, A.J. was the founder and CEO of ArchivesOne, the third largest records management company in the U.S. ArchivesOne was sold to Iron Mountain (NYSE: IRM) after 17 years of operation.
A. J. was the recipient of the Faculty Teaching Excellence Award for outstanding teaching in elective courses at the Yale School of Management in 2022. The U.S. Small Business Administration has recognized A. J. as the Small Business Person of the Year in Connecticut.
A.J.’s incredible collection of writing can be accessed here.
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A.J. Wasserstein: Reflections of a Founder, CEO, Investor and Educator – In The Trenches
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Specific Questions and When They’re Asked
Reflections of a CEO
- (3:30) Please provide us with a brief overview of your career, including what led you to your current roles as a Professor at Yale?
- (5:28) What did you enjoy most about being a CEO? What did you enjoy least about being a CEO?
- (10:41) You’ve mentioned that one of your regrets running ArchivesOne was not moving aggressively enough early enough. How generalizable is this lesson for new operators who have recently ascended to the CEO seat?
- (13:13) As the CEO of ArchivesOne, you purchased 38 other businesses. How do you reconcile the success that you had as an acquiror with the empirical observation that acquisitions are more likely to destroy equity value than to create it?
- (22:55) What are some of the generalizable lessons that you can tease out from the hiring mistakes that you made over two decades as a CEO?
- (28:31) So many CEOs find their overall sense of happiness tied to the commercial success of their companies. Is this as an inescapable reality of entrepreneurship, or is it a potential danger that CEOs can work to overcome?
- (33:44) What was the specific process that you followed at ArchivesOne and OneSource water to either create or discover the core values that you then lived by as a company? How did you ensure that they became more than hollow platitudes?
Reflections of an Investor
- (47:25) In your experience, how are private market valuations correlated with public market valuations, if at all?
- (50:37) Is now a “good time” to acquire a SMB? Is the current macroeconomic climate a help or a hinderance to finding a quality business at a fair price?
Concluding Questions and Reflections
- (57:14) For young, prospective CEOs contemplating whether to take the entrepreneurial plunge: What questions should these people be asking of themselves? If you were given the opportunity to make this decision in your 20s or 30s, how would you think through it?
- (1:04:19) Given your professional success, it would be easy to look at you as somebody who has never really failed at anything. Can you tell us about a time in your life where you were insecure, uncertain, or struggling with something meaningful?
- (1:09:11) What 3-5 books would you put on your personal “Mount Rushmore” of books that you think every SMB CEO ought to read?
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Links to the Resources Discussed
- Beyond Entrepreneurship by Jim Collins
- Authentic Leadership by Bill George
- Execution by Larry Bossidy
- Toyota Way by Jeffrey Liker
- The Outsiders by Will Thorndike
- Delivering Happiness by Tony Hsieh
- How Will You Measure Your Life by Clayton Christensen
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