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Mike and Kass Lazerow are married serial entrepreneurs and investors best known as the co-founders of Golf.com and Buddy Media, a social media marketing platform that sold to Salesforce in 2012 for $745 million. Their entrepreneurial journey began after they reconnected at a mutual friend's wedding in 1996, and two years later they co-founded Golf.com before marrying in 1999. After selling Golf.com to Time Warner in 2006 for $24 million, they launched Buddy Media. Since then, they have supported nearly 100 early-stage startup founders as angel investors and advisors, with their investments generating more than $10 billion in realized gains, including notable successes like Scopely and Liquid Death. They are authors of "Shoveling $h!t: A Love Story" and have received numerous accolades, including being ranked number one on Business Insider's Silicon Alley 100.
➡️ Show Links
https://www.instagram.com/kassandmike/
https://kassandmike.com/
➡️ Podcast Sponsors
Hubspot - https://hubspot.com/
ShipStation - https://www.shipstation.com/ (Code: SuccessStory)
Square - https://square.com/go/success
SurveyMonkey - https://www.surveymonkey.com/scott
Monarch Money - https://www.monarchmoney.com (Code: Success)
Claude - https://claude.ai/success
Huel - https://huel.com/scott (Code: scott)
Revenued - https://www.revenued.com/
NetSuite - https://netsuite.com/scottclary/
Indeed - https://indeed.com/clary
➡️ Talking Points
00:00 – Intro
01:28 – Why Building a Company Is Awful and Amazing
04:33 – How Not to Destroy a Relationship in Business
08:16 – Turning Each Other’s Weaknesses Into an Edge
11:45 – Building a Company With Your Partner
13:56 – Pivot or Die: Surviving the Hard Moments
18:26 – When to Quit vs. When to Push Through
23:29 – Sponsor Break
26:13 – Getting Your Team to Truly Buy In
33:03 – The 3 Real Reasons Companies Fail
35:46 – Why They Hired a Coach After Raising $100M
42:15 – Health, Burnout, and Long-Term Success
51:50 – Sponsor Break
53:45 – The Traits They Bet On as Investors
1:05:38 – Is Social Media Breaking Entrepreneurs?
1:10:38 – The “Go Gauge” Decision Framework
1:15:59 – The Founder Delusion That Kills Great Ideas
1:17:26 – What They Respect Most About Each Other
1:18:23 – The One Lesson They’d Teach Their Kids
