What if the real love story isn’t candlelight and grand gestures, but calendars, clarity, and courage under pressure? I sit down with Kass and Mike Lazerow—longtime partners in life and business—to unpack how they navigated Web 1.0 startups, gut-punch setbacks, and life-changing, $345 million-dollar exits while raising three kids and staying on the same team. Their answers aren’t glossy; they’re practical, repeatable, and surprisingly tender.

We explore how role clarity at home mirrors smart org design at work: defined lanes reduce friction and protect respect. Mike shares why he stopped “selling” inconvenient choices and started owning the impact; Kass explains the power of saying, “No, I’m not happy you’re going”—and not forcing a bow on hard truths. Together they map out their three core cheat codes: share the load through good and bad, invest in the relationship with consistent date nights and short getaways, and build teamwork through radical transparency, fair fights, and fast repair. We also dive into the “pivot” mindset: do more of what works, less of what doesn’t and how boredom and novelty can coexist to keep a marriage alive.

From parenting toddlers to guiding adult kids, from almost losing it all to scaling Buddy Media to a massive exit, Kass and Mike show how trust, weekly meetings, and a shared vision can carry a couple through chaos. If you’ve ever wondered how to blend ambition with intimacy, or how to reset when resentment creeps in, this conversation gives you a clear playbook: define your lanes, tell the truth, meet weekly, repair quickly, and keep dating. 

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