Mike & Kass Lazerow: Golf.com → Buddy Media → Salesforce, Founder Pivots, Investing & The Grass League

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 Intro
1:57 Golf as the thread + “swing test” story
8:35 Spreadsheet → Golf.com concept
11:48 Chipshot.com deal + dot-com crash
13:35 Medinah lunch pitch comeback
14:00 Tiger’s impact on Golf.com
21:39 Buddy Media + Facebook wave
24:16 Pivot to SaaS + recurring revenue
26:14 Panic-attack pivot moment
32:26 Phish tangent
35:30 Building with kids during the grind
40:02 Salesforce transition + Benioff quote
45:16 Investing checklist
53:34 The Grass League: why it works
1:03:01 Outro + book + New York Bluebirds