Kass and Mike Lazerow who are serial entrepreneurs, seasoned investors, and co-authors of Shoveling Sh!t: A Love Story About the Entrepreneur’s Messy Path to Success joined me for one of the most honest conversations I’ve had about what it really takes to build companies and build a life. They share the unvarnished truth about their journey: surviving the dot-com crash, buying Golf.com back from bankruptcy, founding and scaling Buddy Media (eventually acquired by Salesforce for $745 million), and raising three kids while raising capital. They talk about the choices that shaped them, including why they walked away from a bigger offer from Google and how radical transparency kept their team committed during a three-month period when they couldn’t make payroll.

We also dive into the patterns they see in the 100+ startups they’ve backed like how ego, secrecy, and shiny-object syndrome derail founders along with the essential habits that help leaders stay grounded. And because they work together and live together, they open up about how they divide responsibilities, handle stress, and stay connected through exits, pivots, health scares, and everything in between. Their upcoming book distills 50 hard-earned lessons about leadership, resilience, and building a life that actually works. This episode gives you a powerful preview and a reminder that the entrepreneurial path is messy, human, and absolutely worth it.

Where to find Kass and Mike:

Timestamps:

(00:00) The beauty in the struggle: why entrepreneurship is a love story

(01:10) Resilience as identity and getting punched 10 times for one win

(19:19) Creating a workplace people stay in through loyalty and learning

(20:16) Radical transparency: telling the team you might not make payroll

(21:06) Bad news vs. surprises: the leadership rule that protects trust

(22:21) Benevolent dictatorship vs. democracy: choosing decisive leadership

(23:53) Honesty as the most valuable currency in a downturn

(37:30) The pivot mindset: knowing when to throw things away

(52:23) Life after a big exit and leaving ego at the door

(53:45) Why working under others made Mike a stronger leader

(58:26) Founders and the guilt tax: the emotional cost of ambition

(01:08:45) The long-term power of paying it forward

(01:10:01) When cofounding goes wrong: misalignment, fallout, and repair

(01:12:50) Picking the right partner—in life and in business

(01:13:29) Cofounder “prenup” talks: values, work ethic, commitment

(01:14:05) No shortcuts: filtering for grit and willingness to shovel

(01:15:16) Why overlapping founder roles create conflict

(01:21:12) A simple lens for evaluating opportunities without the jargon

(01:22:14) Imposter syndrome and grounding yourself under pressure

(01:24:22) What they wish they’d k

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#106 Kass and Mike Lazerow— Serial Married Founders Sold their Company to Salesforce for $750M on Loving the Journey (Encore)

From Start-Up to Grown-Up