298. Kyle Cooke: Loverboy, SBA Debt & Fighting to Save a Multimillion-Dollar Brand

This week, Jason is joined by Kyle Cooke — entrepreneur, reality TV personality, DJ, and founder of Loverboy — for a conversation on what it really takes to build, scale, and fight to save a consumer alcohol brand in real time. Kyle shares the full story behind Loverboy today — from once scaling to 30 employees, 200-plus distribution agreements, and national attention, to now operating with just three full-time employees while navigating cash constraints, distributor challenges, and millions of dollars in debt. He breaks down the unique economics of the alcohol industry — including why brands are legally required to go through distributors, how wholesalers and retailers cut into margins, and why selling alcohol is far more complicated than most consumer products. Kyle also opens up about the financial pressure behind the scenes, including personally guaranteeing a $4.2 million SBA loan, still owing roughly $2.9 million, and needing to generate over $100,000 a month just to cover the loan payment after taxes. Beyond the numbers, Kyle shares the emotional reality of entrepreneurship — putting $500,000 of his own money back into the business, laying off employees, losing his COO, managing strained vendor relationships, and nearly facing the possibility of bankruptcy. He also explains how the support from Summer House fans helped save Loverboy through direct-to-consumer sales, merch pre-orders, and renewed demand after he vulnerably shared the company’s financial struggles on the show. Jason and Kyle also get into the impact of reality TV on business, why Loverboy’s fan base remains so loyal, how public attention can both help and hurt a brand, and why Kyle has intentionally avoided capitalizing on personal drama in a way that feels cheap or exploitative. From SBA debt and distribution nightmares to multiple revenue streams, DJing, brand partnerships, and rebuilding Loverboy with a leaner team, Kyle gives a raw and honest look at what it means to keep showing up when the business, the money, and the public pressure are all hitting at once. Kyle reveals all this and so much more in another episode you can’t afford to miss! Subscribe to the Trading Secrets podcast! Host: Jason TartickCo-Host: David ArduinAudio: John GurneyVideo: Marc ColcerGuest: Kyle Cooke Learn more about your ad choices. Visit podcastchoices.com/adchoices