Exitwise Productions

Exitwise
  • 5.0 (19)
  • ENTREPRENEURSHIP
  • UPDATED WEEKLY

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

  1. Exited Founder Podcast | Tommaso Trionfi: How He Sold 5 Companies Across SaaS, EdTech, and eCommerce

    1D AGO

    Exited Founder Podcast | Tommaso Trionfi: How He Sold 5 Companies Across SaaS, EdTech, and eCommerce

    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 Thinking about selling your business? Visit https://exitwise.com

    29 min
  2. Exited Founder Podcast | Dan Cornell: What 25 Years and Multiple Exits Taught Him About Selling a Cybersecurity Company

    MAY 13

    Exited Founder Podcast | Dan Cornell: What 25 Years and Multiple Exits Taught Him About Selling a Cybersecurity Company

    In 1999, Dan Cornell sold his first company in an all-stock deal and watched the shares ride from 8 15/16 to nearly $94 — and then, contractually barred from selling or hedging, watched the same stock crash all the way back down. He ultimately sold his shares in chunks at 32 cents, 18 cents, and 9 cents. Twenty-two years later, he sold his second company. Dan walks Exitwise Managing Partner Todd Sullivan through the full arc: co-founding Atension out of Trinity University and selling it to Rare Medium at the peak of the internet bubble, then starting Denim Group in San Antonio in 2001 with Sheridan Chambers and John Dickson. He explains the four-business evolution that took Denim Group from custom software dev to a leading application security firm, the creation of the ThreadFix vulnerability management platform, the asset sale of ThreadStrong to Veracode in 2015, the minority investment from Wipro that started as a full acquisition attempt, and the 2021 sale to Coalfire. Dan also breaks down what nobody tells you about M&A: why "every organization is screwed up in a way that its stakeholders are comfortable with," how bankers reframe your financials to lift multiples, why storytelling is the real lever in a strategic deal, and the brutal reality of running your day job while taking 3:30 a.m. diligence calls with offshore counsel. He talks honestly about the founder-to-VP identity shift, why he never wanted to be "the guy who used to be the guy" twice, and why he now spends his time advising cybersecurity and DevSecOps founders through the Exited Founder Marketplace. Whether you're a cybersecurity founder fielding inbound offers, a software CEO weighing strategic versus PE buyers, or a first-time seller trying to understand the emotional rollercoaster of diligence, this conversation is full of hard-won lessons on deal structure, advisor selection, earn-outs, and what it really feels like to put the backpack down. Learn more about Dan and connect with Exitwise: https://exitwise.com/founders/dan-cornell Thinking about selling your business? Visit https://exitwise.com

    34 min
  3. Exited Founder Podcast | Vik Tantry: How He Bootstrapped FormSwift to $95M and Sold to Dropbox

    MAY 6

    Exited Founder Podcast | Vik Tantry: How He Bootstrapped FormSwift to $95M and Sold to Dropbox

    Sathvik "Vik" Tantry and his co-founder built FormSwift from a freelance frustration into a 10-million-document platform without raising a single venture dollar. Ten years in, they ran a process, went out to 400 potential buyers, and closed a $95 million all-cash deal with Dropbox in December 2022. In this episode, Vik walks Exitwise Managing Partner Todd Sullivan and Brian Dukes through the full journey: spotting the SMB document gap that DocuSign and Adobe ignored, using a phantom equity program to retain key employees without issuing stock, and the deliberate decision to hire VistaPoint Advisors, bankers who understood the nuances of SMB SaaS churn that a standard model would have penalized. Dropbox entered the process quickly, having already acquired DocSend and HelloSign to build a document workflow group aimed squarely at competing with Adobe. Vik also gets into what he'd do differently: he and his co-founder were seen as the face of the business externally, which raised buyer concerns about durability post-exit. His biggest 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 business isn't founder-dependent. He also shares a sharp framework for reading buyer intent mid-process: one runner-up that seemed product-focused turned out to care most about FormSwift's marketing funnel, which completely changed how Vik repositioned for that conversation. Whether you've been building for two years or ten and are starting to wonder if now is the right time to sell, this episode is packed with hard-won insight on bootstrapped exits, deal structuring, and how to position your company as the piece a strategic acquirer didn't know they were missing. Work with Vik on your exit journey: https://exitwise.com/founders/sathvik-tantry Thinking about selling your business? Visit https://exitwise.com

    31 min
  4. Exited Founder Podcast | Colin Hodge: How He Sold His Viral Dating App, Bought It Back in a Fire Sale, and 10X'd It

    APR 22

    Exited Founder Podcast | Colin Hodge: How He Sold His Viral Dating App, Bought It Back in a Fire Sale, and 10X'd It

    Colin Hodge built a dating app so viral it hit one million users in three and a half months — then got sued, kicked off the App Store, acquired by a company in Asia, and sold off in a fire sale when his acquirer panicked mid-IPO. So Colin bought it back. Then he 10X'd it. In this episode, Colin shares the full story with Exitwise Managing Partner Todd Sullivan: from fixing computers at 15 in Pennsylvania, to Microsoft, to launching Bang with Friends at the dawn of the smartphone era. He breaks down the costly mistake of going into M&A pre-revenue, how fast things changed once he finally turned on monetization (zero to $75K/month), and what it felt like to watch his own company get divested like a footnote during someone else's IPO process. Colin also gets into the psychology of M&A that most people skip over: why founders need an honest mirror held up to them before they go to market, how he now helps other founders grow and exit smarter, and how his Amazon bestseller Outrageous Startup Growth started as a way to document his playbook and ended up helping him scale the business beyond himself. Whether you're pre-revenue and wondering when to monetize, stuck navigating your first acquirer conversation, or trying to understand what buyers are really looking for, this one's packed with hard-won lessons from someone who's been on every side of the M&A table. Learn more about Colin and connect with Exitwise: https://exitwise.com/founders/colin-hodge Thinking about selling your business? Visit https://exitwise.com Get Colin's book Outrageous Startup Growth: https://colinhodge.com

    29 min
  5. Exited Founder Podcast | Andrew Kirpalani: From Bar Napkin to Acquisition — Exiting WorkHound

    APR 8

    Exited Founder Podcast | Andrew Kirpalani: From Bar Napkin to Acquisition — Exiting WorkHound

    Andrew Kirpalani co-founded WorkHound in 2015 after being pitched the idea over a beer in exchange for putting his name on an accelerator application. What he agreed to that night became a platform serving 75,000 frontline workers, and a successful acquisition by WorkStep a decade later. In this episode, Andrew shares the full story with Exitwise's Todd Sullivan and Stephanie Horwitz Reuveni: how a 95% annual driver turnover rate in trucking sparked the idea, how anonymous SMS-based feedback gave a voice to workers who'd never sit at a desk, and what happens to a "painkiller" product when the market turns it into a vitamin. Andrew also breaks down how he built a targeted buyer list of 30 to 40 strategic acquirers from a 400-company spreadsheet, why strategics valued WorkHound so differently than PE firms, and what it really feels like to hand over your product and team piece by piece as a technical founder, giving away your toys, one at a time. If you're building toward an exit or navigating a market shift, this one's full of honest perspective on timing, buyer strategy, and the psychology no one warns you about. Want Andrew in your corner when you sell? Connect with him on the Exitwise Exited Founder Marketplace: https://exitwise.com/founders/andrew-kirpalani Thinking about selling your business? Visit https://exitwise.com

    35 min
  6. Exited Founder Podcast | Rachel Murphy: Selling to a Competitor and Building a Founder Exit Playbook

    MAR 25

    Exited Founder Podcast | Rachel Murphy: Selling to a Competitor and Building a Founder Exit Playbook

    Rachel Murphy has been an entrepreneur since she was 12 years old, when she hired her mates to wash cars and kept a cut for herself. That early instinct for building things led her to launch an e-learning systems training academy in her 20s. Then she did it again, building a consulting firm that led large-scale digital transformation for the UK's National Health Service, including standing up the country's Covid-19 digital testing infrastructure. In this episode, Rachel talks about what it was like to sell her second business to a competitor she'd been building a relationship with for years, she shares the emotional reality of running an M&A process while simultaneously managing day-to-day operations, and talks about the steep learning curve of selling to a listed company.  Rachel also opens up about life after exit, from a period of deep self-discovery to building The Grafter, a methodology and service designed to help founders grow revenue, raise capital, and prepare for an exit on their terms. After approaching 42 companies and signing 21, Rachel proved the model works. Today, Rachel is paying it forward as an Exited Founder with Exitwise, bringing her experience as a two-time exited founder to help fellow entrepreneurs navigate M&A transactions. She and Brian also announce a brand-new global partnership between Exitwise and The Grafter.  If you're a founder thinking about selling your business, this one's for you. Learn more about Rachel: https://exitwise.com/founders/rachel-murphy Thinking about selling your business? Visit https://exitwise.com

    32 min
  7. Exited Founder Podcast | Shannon Wilburn: Selling the Franchise Empire She Built From Her Living Room

    MAR 11

    Exited Founder Podcast | Shannon Wilburn: Selling the Franchise Empire She Built From Her Living Room

    Shannon Wilburn started Just Between Friends in her living room, a marketplace for families to buy and sell gently used children's clothes, toys, and baby gear. Over 20 years, she grew it into a nationwide franchise spanning 33 states and doing $60 million in system-wide sales. When her largest franchisee came to her and said "if you ever think about selling, I might want to buy this," Shannon had a decision to make. In this episode, Shannon talks about choosing buyer fit over the highest price and what it meant to protect the legacy of a franchise she'd built for two decades. She shares the emotional reality of letting go, how she leaned on an advisory board of franchise industry heavyweights to navigate the deal, and what the transition looked like on the other side as she stayed on as a board member while watching her company continue to thrive under new leadership. Shannon also dives into what's changing in franchising right now, from the rise of platform companies bolting on brands to how AI is reshaping the landscape for emerging franchise businesses. Today, Shannon is paying it forward as an Exited Founder with Exitwise, advising fellow founders through M&A transactions and bringing 20 years of franchise industry relationships to every deal. If you're a franchise owner thinking about selling your business, this one's for you. Learn more about Shannon: https://exitwise.com/founders/shannon-wilburn Thinking about selling your business? Visit https://exitwise.com

    28 min
  8. Exited Founder Podcast | Sean McKenna: How He Sold His HR Tech Startup to Dayforce in 16 Months

    FEB 25

    Exited Founder Podcast | Sean McKenna: How He Sold His HR Tech Startup to Dayforce in 16 Months

    Sean McKenna launched DataFuZion HCM in the middle of a pandemic with a new baby at home, and just nine months later, Ceridian (now Dayforce) called with an offer to buy. Sean turned it down. Then the offer doubled. Then it tripled. In this episode, Sean shares the full story with Exitwise Managing Partner Todd Sullivan: why he tried (and failed) to buy his former employer first, how he built an MVP that changed the HR tech integration space, and the moment he realized his seven-client startup had something a public company desperately wanted; not revenue, but software and people. Sean also breaks down how bringing in a specialist investment banker moved the valuation from 2x to 6x, how he structured an earn out that created multi-generational wealth, and why five of his team members walked away as millionaires. Whether you're building toward an exit or just curious what it really feels like to sell your company, this one's full of real talk on negotiation, the emotional rollercoaster of M&A, and how to protect yourself on the other side of a deal. Learn more about Sean and connect with Exitwise: https://exitwise.com/founders/sean-mckenna Thinking about selling your business? Visit https://exitwise.com

    28 min
See All (77)

Trailer

5
out of 5
19 Ratings

About

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

Information

  • Creator
    Exitwise
  • Years Active
    2022 - 2026
  • Episodes
    77
  • Rating
    Clean
  • Copyright
    ©️ Copyright 2025 Exitwise, LLC
  • Show Website
    Exitwise Productions

You Might Also Like