What 35 Businesses Taught Dwayne Kerrigan About Building Success w/ Dwayne Kerrigan

In this episode, Benji sits down with serial entrepreneur and podcaster Dwayne Kerrigan, who has owned 35+ businesses across 14 industries. From road building to landscaping to restaurants, Dwayne shares the 5 fundamental business skill sets that span industries.

You’ll hear:

• Why vision is a muscle anyone can build
• The 20-minute “think time” writing exercise that forces breakthroughs
• The shocking truth about culture: you get what you tolerate
• Why sales scripts are the ultimate freedom—not a crutch

⏰ Timestamps
00:00 – Intro: 35+ businesses before 40
06:59 – The power of singular focus vs. juggling businesses
12:51 – Vision is a muscle, not just a gift
16:23 – The power of better questions
22:40 – The brutal 20-minute think-time exercise
27:29 – Culture = you get what you tolerate
41:12 – Sales is table stakes—find the pain point
57:57 – Becoming data-driven: P&Ls and finance days
01:01:51 – Advice to 21-year-old me

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