Exitwise Productions

Tommaso Trionfi has sold five companies across SaaS, EdTech, and ecommerce, including Wimba to Blackboard and Merchantry to Tradeshift in an all-stock deal that landed him a stake in what's now a $3.2 billion company. He's done it from every angle: founder-CEO, hired-gun CEO, and operator running divestitures inside a private equity firm.

In this episode, Tommaso sits down with Exitwise Managing Partner Todd Sullivan to walk through the nine years he spent building Wimba into the #1 virtual classroom for higher ed: 800+ institutions, $20M+ ARR, and the post-2008 moment he realized Blackboard was about to buy his closest competitor and corner him out of the market. He explains why he pushed his board to sell while the baby could still grow, the Merchantry deal where he took $30M in Tradeshift shares instead of cash, and the 18-month sprint at Oak Hill Capital where he divested Alibris, Monsoon Commerce, and Stone Edge through his personal network. "You sold yourself out of a job," as his wife put it.

Tommaso also breaks down what surprised him most across five exits: M&A in the $10–100M range is almost entirely a relationship business, not a banking one. He talks about reading market timing, when to take stock vs. cash, the emotional weight of selling "your baby," and why he now coaches founders through earn-outs and PE acquisitions, including the Cloud Academy CEO he kept from walking away from a fortune early. Today, he's co-founder of Noro, a life-size immersive portal redefining remote collaboration, and advises B2B SaaS and EdTech founders on exit strategy.

Whether you're staring down your first acquisition offer, weighing a stock-vs-cash deal, or trying to figure out when to sell before the window closes, this conversation is full of hard-earned wisdom from a founder who's been on every side of the table. If you want to build with the exit in mind, Tommaso's playbook is one to study.

Learn more about Tommaso and see how he can help you on your exit journey: https://exitwise.com/founders/tommaso-trionfi
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