ShipCompliant - "Successful" Exit

                We read and hear a lot of stories in this class about entrepreneurs who are currently fighting the good fight in the wine industry, and a handful of stories about unsuccessful ventures.  We’ve heard fewer case studies of successful wine-industry exits, and I happened to hear about one this weekend so I figured I’d share. 

If you believe my mother, it turns out I have a distant cousin, Jason Eckenroth, who founded a wine DTC compliance and logistics software business, ShipCompliant, in his college dorm-room and grew it into a business at scale over 17 years.  After doing a bit of stalking online I found that he sold the business to a PE buyer several years ago and now is effectively retired splitting his time between Barcelona Spain and Denver Colorado. 

Even more surprising were the several interviews and blogs I found online where Jason muses on whether he made a mistake in selling the business when he did.  Here’s a link here to a speech he gave on “the agony and ecstasy of selling my business”: https://businessofsoftware.org/2017/11/the-agony-and-ecstasy-of-selling-my-business-jason-eckenroth-shipcompliant-bos-europe-2017/

It took him selling his business to realize how much purpose he derived from running it.  In retrospect it sounds like, were he to have a do-over, he would have kept ownership for life, and he has now built a reputation as a mentor to founders who are struggling with what to do over inbound offers to buy their businesses.

Really interesting (and admittedly a bit cliché) to hear from a founder/operator who had a great exit, and thought that would be their big “arrival”, but realized they missed the hustle of being in the business when they get out.  Would be interesting to compare this reaction with some other wine business owners who have managed to successfully exit the business.