Not many couples can point to a twenty-eight-year partnership that includes building and selling a business for $750 million and investing in more than a hundred startups along the way. When Kass and Mike Lazerow joined Sean Kelly on the Digital Social Hour, they brought that combined experience to bear on some of the most practical questions in entrepreneurship: how to focus, when to pivot, how to build a culture people actually want to work in, and what it is really like to build alongside a spouse.
The conversation is grounded and honest in a way that makes it stand out from the typical entrepreneurial success narrative. Kass and Mike do not shy away from the complexity of their journey — the stress, the decisions that did not go as planned, the discipline required to stay focused across decades of work and life together.
About Kass & Mike Lazerow
Kass and Mike Lazerow are serial entrepreneurs best known for co-founding Buddy Media, the social media marketing platform that sold to Salesforce in 2012 in a deal valued at approximately $750 million. That exit established them as significant figures in the digital marketing and tech startup world, and they have since channeled that experience into building, advising, and investing — with more than 100 startup investments between them.
Together they run a platform and community for entrepreneurs, including the book and brand Shoveling Shit, which channels their philosophy of hard-won practical wisdom over polished theory. Their marriage and business partnership, now nearly three decades long, is itself a case study in focus, alignment, and the kind of radical transparency they discuss openly in their work.
What Kass & Mike Lazerow and Sean Kelly Talked About
- How Kass and Mike Lazerow think about focus as the fundamental skill separating successful entrepreneurs from the rest
- Lessons from building and exiting a company for $750M — and what they would do differently
- Their approach to working as romantic and business partners without letting either relationship undermine the other
- The investment framework they have developed across more than 100 startup bets
- Why they believe radical transparency is essential to building company culture worth staying for
- Their take on the value of college, job-hopping, and how career-building has changed for younger generations
- How they think about leadership: what it means to lead by example in a remote and distributed environment
- The role AI plays in their current thinking about the future of business and entrepreneurship
Why This Conversation Matters
Kass and Mike Lazerow's episode on the Digital Social Hour delivers something that is genuinely rare: entrepreneurial wisdom that comes from people who have actually done it, not just observed it. Their combination of a landmark exit, deep investment experience, and a decades-long partnership as both colleagues and spouses gives their perspective a texture and credibility that most business conversations simply cannot match.
▶ Watch the full episode on YouTube
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About Sean Kelly & the Digital Social Hour
Sean Kelly is an entrepreneur and the host of the Digital Social Hour, one of the fastest-growing interview podcasts in the world, where he sits down with entrepreneurs, athletes, creators, and cultural voices for candid, long-form conversations. The show draws over 100 million views a month across platforms. Explore more guest features on SeanKelly.io.
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