Exitwise Productions

Andrew Lassise tried to sell his IT company in 2019, and got rejected. Revenue was down, there were no contracts, no recurring revenue, no clean story. So he rebuilt. Then COVID gave him free money, the IRS handed him a monopoly, and a 700-person company came knocking for his 12-person firm.

In this episode, Andrew shares the full arc with Exitwise’s Stephanie Horwitz Reuveni & Todd Sullivan: from selling literal air guitars on eBay as a teenager, to building Tech 4 Accountants into the dominant cybersecurity firm for accounting professionals, to a 2023 strategic acquisition by Rightworks who came to him and had to make it worth his while. Andrew had 6,000 clients on a compliance product his future acquirer had 32 of. They had no leverage. He had all of it.

Andrew also gets painfully honest about what happened after he cashed out. Three hours after collecting his retention bonus, he quit. His entire team was fired. The entrepreneur who had been crowned the industry expert found himself in a corporate machine that killed off a million-dollar-a-year product because it didn't fit the org chart. The identity crisis that followed — "I used to run a tech company" — led him to found Sober Founders, a 501(c3) community for entrepreneurs in recovery, built on the same framework he credits with keeping him grounded: shared experience over advice, not a therapist telling you what to do but someone who's been in the hole showing you how they got out.

Whether you're building toward a first exit, trying to understand what life looks like on the other side, or just want to know what it actually takes to turn a rejected deal into a life-changing one, Andrew's story is the rare kind that's equal parts playbook and confession.

Learn more about Andrew and how he can help on your exit journey: https://exitwise.com/founders/andrew-lassise 

Getting exit-ready or thinking about selling your business? Visit https://exitwise.com

Learn about Sober Founders: https://soberfounders.com