Welcome back to another edition of The Wise Exit newsletter.

This week, we're doing something a little different.

We just wrapped Season One of the Exited Founder Podcast. Ten episodes, 10 remarkable founders, and somewhere north of 20 exits between them across industries ranging from cybersecurity to franchising, HR tech to edtech, consumer apps to SaaS and beyond.

Every one of these founders built something real. Every one of them went through the fire of an M&A process. And every one of them chose to join the Exitwise Exited Founder Marketplace because they want to help you navigate yours.

We're proud of what they built. But we're even prouder of why they're here.

This week, we're pulling the biggest lessons from Season One into one place: not as a highlight reel, but as a gift. Because if there's one thing every founder on this podcast made clear, it's that you shouldn't have to figure this out alone.

Let's dive in.

What 10 Founders and 20+ Exits Taught Us About Getting to a Great Outcome

When you listen to all 10 conversations from Season One back to back, the same themes keep surfacing. Different industries, different deal structures, different timelines, but the same hard-won truths underneath.

Here's what stood out most.

This was the loudest drumbeat across the entire season. Andrew Lassise (IT and cybersecurity) tried to sell his company in 2019 and got rejected. No contracts, no recurring revenue, no clean story. He rebuilt with all of that in mind and when a strategic buyer came to him in 2023, he had all the leverage. Dan Bauer (MBA consulting and PE advisory) put it simply: run your business like it's always for sale. Not as a financial exercise. As a strategic one. He didn't name his firm after himself on day one. He trademarked every service line. He structured the business so the exit conversation was never about one person. Sean McKenna (HR tech and payroll software) launched DataFuZion HCM during a pandemic, got an acquisition offer nine months in, turned it down, and watched it double, then triple, because he was prepared enough to wait for the right outcome (and worked together with Exitwise in doing so!)

Tommaso Trionfi (EdTech, SaaS, ecommerce, and private equity) has been through five exits across multiple industries. His biggest surprise across all of them was how relationship-driven M&A really is, especially in the $10–100M range. He knew his buyer at Blackboard for years before a dollar changed hands. And when he was running divestitures at Oak Hill Capital, he moved three companies through his personal network. Dan Bauer’s exit was a management buyout with a former client he'd known for years before the first conversation about a deal. Shannon Wilburn (franchising and consumer goods) sold Just Between Friends — a nationwide franchise doing $60 million in system-wide sales — to her largest franchisee, someone already in her world. Rachel Murphy (e-learning and digital transformation) sold to a competitor she'd spent years building a genuine relationship with. The pattern across all of them is the same: the people who end up buying your business are usually already in your orbit. The question is whether you're nurturing those relationships before you need them.

Vik Tantry (SMB SaaS and document tech) bootstrapped FormSwift for 10 years and closed a $95 million all-cash deal with Dropbox. His biggest regret was that he and his co-founder were seen as the face of the business, which raised buyer concerns about what happens after they leave. His lesson: build a strong, visible number two early. Not just to run the day-to-day, but to show up in front of buyers and prove the engine runs without you. Colin Hodge (consumer apps and growth) learned the same thing across multiple transactions, including buying his own company back after his acquirer divested it during an IPO panic. He's now deliberately building his team so the business doesn't depend on him being in the room. Andrew Lassise said it best: by the time his second exit came around, he'd built a company that ran itself without him, and that became his greatest source of leverage.

Sean McKenna worked with Exitwise to find a specialist investment banker who truly understood HR tech, and watched his valuation move from 2x to 6x. Five of his team members walked away as millionaires. Dan Cornell (custom software, application security, and cybersecurity) learned this across multiple transactions over 25 years, including a painful first exit where an all-stock deal in 1999 left him selling shares at 32 cents, 18 cents, and 9 cents after watching them peak near $94. By the time he sold Denim Group to Coalfire, he understood exactly what having the right people in your corner actually meant. Andrew Kirpalani (HR tech, logistics, and B2B SaaS) put it this way: because he had exited founder friends to confide in during the WorkHound sale, he was able to approach the whole process in a more zen-like way, experiencing the emotional journey without letting it drive his decisions.

Shannon Wilburn chose buyer fit over the highest price because protecting the legacy of what she'd built for 20 years mattered more to her than the number. She called an exit what it actually is: not just a financial transaction, but an emotional transformation. Dan Cornell described closing his deal as finally setting down a backpack he'd been carrying so long he'd forgotten what it felt like not to have it on. Andrew Kirpalani talked about the importance of founder therapy, having someone in your corner who helps you stay grounded when the process gets hard. Colin Hodge said what most founders won't: you need an honest mirror held up to you before you go to market, and most people don't have one. Tommaso Trionfi, who has more exits than almost anyone we've spoken to, said the thing he wishes he'd done earlier was get a coach. Someone who could find his blind spots, because we all have them.

The founders who get the best outcomes aren't always the ones with the best businesses. They're the ones who prepared early, built teams around them, understood what buyers were really looking for, and had people in their corner who'd already been through it.

That's exactly why every one of these founders joined our Exited Founder Marketplace. Not because they had to. Because they wanted to. Because they remember what it felt like to navigate this without the right support, and they don't want that for you.

☑️ Audit your business like a buyer would today. Walk through your financials, your contracts, your key person dependencies, and your documentation. Write down the three things a buyer would flag immediately. Those are your starting points.

☑️ Map the relationships already in your orbit. Who in your network has shown interest in your space, acquired companies like yours, or could be a natural strategic fit? You don't need to do anything with the list today. Just know who's on it and start showing up for those people.

☑️ Identify who runs the business when you're not in the room. If the honest answer is nobody, that's your most important hire. If someone is already doing it, make sure buyers can see it clearly.

☑️ Get the right people around the table before you need them. Whether that's an M&A advisor, an exited founder in your industry, or both — the time to build those relationships is before an offer lands on your desk, not after.

☑️ Think through what you actually want on the other side. Shannon Wilburn chose fit over price. Dan Cornell said closing felt like setting down a backpack. Andrew Lassise found himself figuring out his identity three hours after collecting his retention bonus. The emotional reality of an exit catches most founders off guard. Start thinking about it now.

Or listen wherever you get your podcasts!

Every founder featured this season is available to work with you directly through the Exitwise Exited Founder Marketplace. And they're just the beginning. Whether you're actively preparing for a sale or just starting to think about what an exit might look like, there's someone on our marketplace who has built and sold in your industry and genuinely wants to help you get there.

You don't have to figure this out alone.

Find your Exited Founder at exitwise.com/search-exited-founders

And if you're not sure where to start, just reply to this email. We're always happy to point you in the right direction.

Talk next week,

Brian Dukes
Managing Partner at Exitwise