Ep. 8 Seasoned, Not Done: Turning Decades of Experience into a Successful Exit (feat. Tom McKeown)

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Exit-Ed: Stories From Grind to Sale

Gabriela Smith

10 episodes

1 month ago

Exit-Ed: Stories from Grind to Sale Join us on Exit-Ed, the podcast where successful founders share the untold stories behind building, scaling, and selling their companies. In each dynamic episode, we go beyond the headlines to explore the challenges, strategies, and pivotal moments that shaped the journeys of entrepreneurs from each corner of the globe. From the long nights spent grinding to the high-stakes negotiations that led to rewarding exits, our guests provide practical insights, hard-won lessons, and inspiration for anyone on the path to success. Whether you're an entrepreneur preparing for a sale, an investor looking to understand founder dynamics, or a business leader seeking new growth strategies, this podcast is for you. Learn from those who've been there. Get Exit-Ed.

All content for Exit-Ed: Stories From Grind to Sale is the property of Gabriela Smith and is served directly from their servers with no modification, redirects, or rehosting. The podcast is not affiliated with or endorsed by Podjoint in any way.

Ep. 8 Seasoned, Not Done: Turning Decades of Experience into a Successful Exit (feat. Tom McKeown)

Exit-Ed: Stories From Grind to Sale

56 minutes

1 month ago

Ep. 8 Seasoned, Not Done: Turning Decades of Experience into a Successful Exit (feat. Tom McKeown)

In this episode of Exit-Ed: Stories from Grind to Sale, Gabriela Smith interviews Tom McKeown, founder and former CEO of Trend Data. Tom shares how, at age 56, he left a long corporate career to build and sell a successful HR analytics company—proving it’s never too late to become an entrepreneur.

Trend Data, founded in 2017, used AI-driven people analytics to help companies identify workforce trends such as turnover and recruiting success. Tom and his co-founder saw an opportunity to serve mid-market clients that lacked affordable analytics tools. The company grew steadily until the pandemic hit, forcing hard choices and stalled funding rounds. Still, Trend Data survived and caught the attention of iSolved, a national HR and payroll firm. What began as a potential partnership turned into an acquisition finalized in June 2021.

Tom stayed on for two years to oversee integration and product expansion before stepping away in 2024. Reflecting on the sale, he highlights the importance of organization and discipline: keep documentation ready, align stakeholders early, and resist overreaching earn-outs. Most of all, understand that after the deal closes, the product belongs to the buyer—founders must adapt quickly.

Before founding Trend Data, Tom spent decades in software, working with firms like Adobe, Citrix, and WebEx, and leading multiple HR tech exits. He credits his early inspiration to Ross Perot, whose advice to “learn an industry cold” shaped his approach to entrepreneurship.

After his exit, Tom published This Is Panther Country: A Memoir of Youth, Underdog Spirit, and Basketball Glory, about his Long Island high school basketball team. He draws parallels between sports and business—pressure, teamwork, and knowing when to pivot.

Today, Tom advises several startups in HR and technology and believes AI, like past innovations, will create more opportunities than it eliminates for those willing to adapt. His story is a testament to resilience, reinvention, and the value of experience in building and exiting a company.