Serial entrepreneur Rick Mekdessie sold uGov Systems, watched the deal nearly collapse at the last minute, and learned within six months of closing that private equity had already bought his company out from under the buyer he trusted.
Rick joins Maartje van Krieken on The Business Emergency Room to talk about what actually happens after the champagne runs out. He built eGov Systems around a strange gap in Louisiana tax law, took it through a near-collapsed sale, and then watched the company he'd handed off get bundled and flipped to private equity without a word of warning. What do you actually owe yourself before you sign an LOI? Rick's answer: do your own due diligence first, line up more than one buyer, and know your number before anyone else does.
The conversation also digs into a mistake Rick doesn't dress up. When he acquired a consulting firm, he kept both identities separate instead of building something new, and the resentment that grew from it taught him more than the acquisition itself did. How much of founder success comes down to timing versus knowing when to walk? Rick argues it's mostly the latter, and he's using that lesson to build his next company smaller, leaner, and on a timeline that actually fits the years he has left to build it.
Episode Breakdown:
00:00 Introducing Rick Mekdessie, Entrepreneur and Investor
03:26 How Louisiana's Tax Law Sparked the eGov Systems Idea
07:13 Why Seller-Side Due Diligence Can Save a Business Sale
13:37 When a Trusted Buyer Sells Your Business to Private Equity
15:56 The Merger Mistake That Created an Us-Versus-Them Culture
21:28 Why This Founder Is Building an AI Startup
27:54 Building Board Trust Before You Ever Plan an Exit
Connect with Rick Mekdessie:
uGov Systems
Email: [email protected]
Rick Mekdessie is the Founder and CEO of uGov Systems, a GovTech company focused on helping state and local government agencies leverage artificial intelligence to improve revenue collections, operational efficiency, and citizen services.
A lifelong entrepreneur and technology executive, Rick has spent more than two decades building technology-driven solutions for government agencies across the United States. His experience spans tax administration, electronic filing and remittance systems, and digital modernization initiatives.
His mission is to help government agencies harness the power of artificial intelligence to operate more effectively, recover critical revenue, and deliver better outcomes for the communities they serve.
Outside of building companies, Rick is big on giving back. He is an active mentor, investor, and advocate for entrepreneurship and innovation. He regularly works with startup founders, university entrepreneurship programs, and economic development organizations, and has served as a judge, mentor, and advisor for numerous startup accelerators and business pitch competitions.
Connect with Maartje van Krieken:
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Host Maartje van Krieken is a crisis strategist and decision-making expert who thrives in high-stakes business environments. Combining disaster management training, hands-on experience in global industries, and leadership skills honed as a seasoned sailor, she helps businesses navigate chaos with precision. Whether tackling transformation, scaling challenges, or leadership bottlenecks, Maartje delivers actionable insights to turn turbulence into traction.
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