Why entrepreneurship is 'awful and awesome'

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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/ 

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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 

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Revenued - https://www.revenued.com/ 

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➡️ 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