Exitwise Productions

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

What is Exitwise Productions?

Exitwise Productions is the home of M&A education for entrepreneurs. If you're a founder thinking about selling your business, a business owner exploring your exit options, or simply trying to understand how mergers and acquisitions actually work, this is where you start.

Three shows. One mission: get founders the exit they deserve.

The Wise Exit by Exitwise is hosted by Todd Sullivan, M&A advisor and CEO and Co-founder of Exitwise. The Wise Exit brings you in-depth conversations with founders and business owners who have successfully sold their companies to some of the top acquirers in the world. From business valuations and quality of earnings to choosing the right M&A advisor or investment banker for your deal, The Wise Exit covers every stage of the M&A process with the depth and clarity that founders actually need.

On the Exited Founder Podcast by Exitwise, hear first-hand exit stories from successful founders across dozens of industries who are now paying it forward as M&A advisors with Exitwise. Each episode features an exited founder sharing what they wish they had done differently, their take on current industry trends, and the lessons they are 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.

Wise Up on M&A by Exitwise is the M&A education series for entrepreneurs who are curious about selling their business but don't know where to start. Each episode breaks down one mergers and acquisitions concept in plain English, with zero jargon left unexplained. If you have ever nodded along in a conversation about LOIs, EBITDA, or quality of earnings and had no idea what any of it meant, this show is for you.

Whether you are 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 and work with Exitwise at exitwise.com.