From Poker to Nightlife to Digital Marketing

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Join me, Nik (https://x.com/CoFoundersNik), as I interview Ryan Bartlett, founder and CEO of True Classic (https://x.com/@RyanBartlett)

From failed musician and poker player to billion-dollar t-shirt brand founder, Ryan Bartlett's entrepreneurial journey is proof it's never too late to start a business. In this episode, we explore how Ryan built True Classic from zero to over $100 million in revenue in just two years, selling 30+ million t-shirts and becoming one of the fastest-growing e-commerce brands in the apparel industry.

Questions This Episode Answers:

Is it too late to start a business in your 30s or 40s?

How do you pivot from a failed career into successful entrepreneurship?

What skills from music and poker translate to building a billion-dollar business?

How did True Classic grow from $0 to $100M in just two years?

What is the "white space opportunity" strategy for finding winning business ideas?

How do you identify which business idea to pursue (the "fat pitch" method)?

When should you transition from founder-operator to hiring a CEO?

How do you scale a team from scrappy generalists to specialized experts?

What role does creativity play in winning at e-commerce and digital marketing?

How do you build risk tolerance for making big inventory and business bets?

What are the three core problems True Classic solved in the t-shirt market?

How do you compete in a "boring" or saturated industry like apparel?

How important are co-founders vs. going solo as an entrepreneur?

What's the best way to test products cheaply using drop shipping?

How do Facebook ads and paid media drive D2C brand growth?

Why do employees quit without warning and how do you prevent it?

How will AI tools like Sora change marketing and ad creative production?

Should entrepreneurs use AI video generation for Facebook advertising now?

What's True Classic's expansion strategy (women's line, new products)?

How do you balance profit with purpose and philanthropic impact?

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This week we covered:

00:00 – Intro: Who is Ryan Bartlett / True Classic story

03:05 – Failing in music & poker for a decade

10:08 – Moving from poker to digital marketing

12:25 – Creativity becomes a business advantage

14:49 – Compounding skills over 10+ years

17:14 – Running a $1M/year marketing agency

22:01 – Solving fit, feel, and price in clothing

24:19 – Why boring industries have big opportunity

26:44 – The bet that launched True Classic

31:33 – Leveraging experience & risk tolerance

33:57 – Scaling to $100M and needing a real team

36:12 – Creatives vs Operators

38:33 – Why people management is the hardest part

40:45 – Staying in your area of strength

43:12 – You don’t need perfect planning to start

45:33 – Failure builds the muscle

47:57 – Creativity is the real advantage

50:20 – AI + Sora + creativity for content

55:02 – Sora is changing marketing