How To Kill Your Business (with Kevin Jennings)

Business owners spending thousands on marketing to chase one client at a time are playing the wrong game. Most never consider that the largest buyer in the country already publishes exactly what they want, how much they’ll pay, and where to find the opportunity, every single day. If you’re stuck as the bottleneck in your business, burning cash on client attraction, or sitting on a great company with no idea how to exit it profitably, this conversation will shift how you think about revenue, risk, and what your business is actually worth. In this episode of Built to Exit, Jason Sisneros sits down with Kevin Jennings, government contracting expert, serial acquirer, and founder of The Government Cheese, to break down how everyday service businesses can tap into government contracts, why Kevin’s first exit was a painful masterclass, and what it actually takes to go from running one company to building a nine-figure roll-up. Together, we break down: -Why government contracts eliminate the hardest part of business: finding the customer -How a five-year street sweeping contract at the Las Vegas airport covers all the bases -Why 23% of every federal dollar is earmarked for small businesses and most never go after it -What Kevin got wrong in his first exit and why he calls it a “paid MBA” -How running eight businesses became easier than running one -The four startup traits (arrogance, impatience, wrong team) that must flip before you scale -Why knowing your worth as a person, not just a business, changes every negotiation This episode is for business owners who want to: -Add reliable, long-term revenue without spending more on marketing -Avoid a dictated exit where the buyer controls price, timing, and terms -Build a business that runs without them so they can be present for what matters You do not have to figure out government contracts alone, and you do not have to repeat the mistakes Kevin made on his first exit. This episode shows where service-business owners leave money on the table and how to stop. Timestamps 00:00 – Why business owners never consider the government as a client 02:54 – Kevin’s journey: football, real estate crash, and the pivot to government contracts 06:09 – What the government actually buys (hint: it’s not just guns) 09:30 – The janitor analogy: jobs the government stopped filling and now contracts out 12:22 – How government contracts reduce concentration risk and boost your multiple 13:56 – Five-year deals and guaranteed revenue: why Kevin locks in long-term contracts 17:00 – Zero marketing spend: one website, every federal opportunity, every day 19:30 – Running eight businesses is easier than one, here’s why 21:30 – The mindset shift: killing the ego to scale past eight figures 26:30 – Kevin’s NICU moment and why he had to change how he ran his business 31:00 – Kevin’s first exit: uneducated seller, dictated deal, and the lessons inside the pain 37:30 – Building the seller’s code: controlling price, timing, and terms 43:00 – Kevin’s one piece of advice: know your worth 🔗 Connect with Kevin Jennings Find Kevin across all socials: @thegovernmentcheese Facebook | Instagram | TikTok | YouTube: The Government Cheese 🔗 Connect with Built to Exit Website: builttoexit.biz Subscribe for weekly conversations on building enterprise value and exiting on your terms. #GovernmentContracts #BuiltToExit #BusinessExit