EPISODE · Feb 25, 2026 · 1H 4M
Mike & Kass Lazerow: Golf.com → Buddy Media → Salesforce, Founder Pivots, Investing & The Grass League
from The Dan Evans Show · host Dan Evans
Mike and Kass Lazerow join The Dan Evans Show for the full breakdown of their golf-to-tech-to-investing journey: the Golf.com origin story, the dot-com crash and comeback, Buddy Media’s growth and sale to Salesforce, the hard pivots founders have to make, and why they believe The Grass League is a perfect modern golf format.0:00 Intro1:57 Golf as the thread + “swing test” story8:35 Spreadsheet → Golf.com concept11:48 Chipshot.com deal + dot-com crash13:35 Medinah lunch pitch comeback14:00 Tiger’s impact on Golf.com21:39 Buddy Media + Facebook wave24:16 Pivot to SaaS + recurring revenue26:14 Panic-attack pivot moment32:26 Phish tangent35:30 Building with kids during the grind40:02 Salesforce transition + Benioff quote45:16 Investing checklist53:34 The Grass League: why it works1:03:01 Outro + book + New York Bluebirds
What this episode covers
Mike and Kass Lazerow join The Dan Evans Show for the full breakdown of their golf-to-tech-to-investing journey: the Golf.com origin story, the dot-com crash and comeback, Buddy Media’s growth and sale to Salesforce, the hard pivots founders have to make, and why they believe The Grass League is a perfect modern golf format.0:00 Intro1:57 Golf as the thread + “swing test” story8:35 Spreadsheet → Golf.com concept11:48 Chipshot.com deal + dot-com crash13:35 Medinah lunch pitch comeback14:00 Tiger’s impact on Golf.com21:39 Buddy Media + Facebook wave24:16 Pivot to SaaS + recurring revenue26:14 Panic-attack pivot moment32:26 Phish tangent35:30 Building with kids during the grind40:02 Salesforce transition + Benioff quote45:16 Investing checklist53:34 The Grass League: why it works1:03:01 Outro + book + New York Bluebirds
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Mike & Kass Lazerow: Golf.com → Buddy Media → Salesforce, Founder Pivots, Investing & The Grass League
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