It was my pleasure to welcome A.J. Wasserstein to the podcast this week: In addition to being a Lecturer in the Practice of Management at the Yale School of Management, AJ is also an accomplished entrepreneur, having founded, operated and sold ArchivesOne, a records management company, over the course of 17 years.

Following this experience, A.J. was the President of Onesource Water, the third-largest bottleless water service business in the U.S., which he also sold, this time to Water Logic, a strategic acquirer, in 2016.

As if all of that weren’t enough, A.J. is also a very experienced private investor in lower middle-market businesses.

Today’s episode is loosely broken out into three parts: We begin our discussion reflecting upon his time as a CEO, including his largest sources of regret, how he grew ArchivesOne through executing on 38 (!!) tuck-in acquisitions, and how he separated his overall sense of happiness from the commercial success of his business.

We then transition to some of the lessons that he has learned as an investor, including the extent to which private market valuations are correlated with public markets, and whether he thinks now is a good time to acquire a SMB.

Finally, we conclude with a few personal reflections, including how he would advise somebody in their 20s or 30s considering the entrepreneurial path, and the 7 books that all #SMB CEOs must read.

Please enjoy!

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