Breaking the Feed: Kass and Mike Lazerow on Building, Selling, and Betting Together

How do you keep going when your biggest success comes with losing almost everything along the way? On Breaking Precedent, Kass and Mike Lazerow discuss their book Shoveling Shit: A Love Story and what happens when entrepreneurship and marriage collide, especially while raising three kids. They recount their early entrepreneurial roots, meeting in the mid-’90s internet era, and building Golf.com. They sold it to Chipshot during their honeymoon period, lost access to everything when Chipshot ran out of money, then rebuilt and ultimately sold Golf.com to Time Warner amid Tiger Woods’ rise. They describe starting Buddy Media in 2007 while juggling a newborn, scaling it, and selling to Salesforce for $745M, yet feeling strained, unhealthy, and disconnected afterward. Now investors, they outline their “Go Gauge” framework for evaluating ideas, argue there’s no perfect time to start, push back on bias against married co-founders, and emphasize embracing the “shoveling” reality while using AI to stay competitive. Key Insights - Entrepreneurship is less about avoiding failure and more about learning to keep moving when things fall apart. - The hardest parts of building a company often happen in the messy middle, when uncertainty, sacrifice, and setbacks become part of the journey. - Success can look very different behind the scenes, especially when professional achievements come with personal and family costs. - Complementary strengths between partners can become a powerful advantage when building a company together. - Setbacks can become turning points when entrepreneurs keep working through the problem instead of staying focused on what went wrong. - There may never be a “right” time to take the leap. Timestamps 00:00 Welcome  02:49 On the Entrepreneurial Journey 07:24 Early Hustles And Roots 10:45 Mike Learns Freedom 13:17 Meeting In Web One 18:17 Golf Dot Com Crash 22:24 Shoveling And Lucky Breaks 26:03 Buddy Media Sacrifices 27:53 Credit And Co Founder Balance 31:42 Exit Aftermath Feelings 33:26 Health Wake Up Call 35:31 Writing The Real Story 36:52 From Founders To Investors 39:25 Go Gauge Framework 43:11 Messy Middle Mindset 44:55 AI As Operating System 48:33 Rethinking Venture Rules 51:09 Venture Capital Reset 55:12 Legacy And Precedent 59:57 Closing Thanks  Resources Mentioned Shoveling Shit: A Love Story: https://www.shovelingshit.com/ Golf.com: https://golf.com Salesforce: https://www.salesforce.com Warner Media: https://www.warnermedia.com Thank you to our Precedent Breaking Partners! Squared Away: gosquaredaway.com/breakingprecedent?utm\source=breakingprecedent&utm\medium=podcast&utm\campaign=breakingprecedent&utm\content=podcast TaskRabbit: taskrabbit.com/?utm\source=breakingprecedent&utm\medium=podcast&utm\campaign=breakingprecedent&utm\content=podcast Justworks: justworks.com/?utm\source=breakingprecedent&utm\medium=podcast&utm\campaign=breakingprecedent&utm\content=podcast Leah Solivan is the host of Breaking Precedent, a podcast that explores the stories of innovators who are pushing societal boundaries and setting new precedents in their fields. Leah Solivan is General Partner at Fuel Capital, where she invests in early-stage companies across consumer technology, hardware, education, marketplaces, and retail. Leah Solivan has 15 years of experience building and creating technology products that have reached millions of people around the globe. She started her career at IBM as an engineer in the software group, working on Lotus Notes and Domino. In 2008, Leah Solivan founded TaskRabbit, the leading on-demand service marketplace in the world. Connect with Leah Solivan: Website: breakingprecedent.com/ Instagram: https://www.instagram.com/leah\_solivan/ X: https://twitter.com/labunleashed?lang=en