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.
What is Exitwise Productions?
Exitwise Productions is your one-stop shop for M&A education, real-world exit stories, and expert insights. Whether you're a founder planning to sell, a business owner exploring your options, or just looking to understand how mergers and acquisitions really work.
The Wise Exit · Host Todd Sullivan, M&A Advisor and Exitwise CEO & Co-founder, brings you in-depth conversations with founders and former business owners who've sold to some of the top acquirers in the world, alongside focused masterclasses and expert guidance on the M&A process. From business valuations and quality of earnings to choosing the right M&A advisor or investment banker for your deal, The Wise Exit breaks it all down.
The Exited Founder Podcast · Hear first-hand exit journeys from successful founders across dozens of industries who are now paying it forward as M&A advisors with Exitwise. Every episode features an exited founder sharing what they wish they'd done differently, their take on current industry trends, and the lessons they're bringing to help the next generation of business owners maximize their exits. Meet the advisors and explore the Exited Founder Marketplace at exitwise.com/exited-founders
Whether you're years away from selling or already exploring a transaction, Exitwise Productions gives you the insights, strategies, and real-world perspective to get the exit you deserve.
Learn more at exitwise.com