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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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What if the biggest reason most startups collapse has nothing to do with the product and everything to do with the founder behind it?
In this episode, we sit down with Greg Cassar: self-made multimillionaire, growth hacker, investor, and the strategic mind behind scaling 350+ companies. He’s built businesses generating over two million dollars a month… but the part that stands out is the freedom he’s created along the way. Greg surfs every day, spends time with his family, mentors entrepreneurs around the world, and lives a lifestyle he intentionally designed.
Together, we break down why nearly 90% of startups fail—and what the remaining 10% do differently. Greg reveals the mindset founders need before launching, the structural traps that set most startups up to burn out, and the real marketing and investing strategies that matter in 2025’s attention-driven world.
You’ll hear insights on how Greg chooses the right businesses to back, how to shift from “doing everything” to becoming the CEO of a self-managing company, and which skills will genuinely separate winning founders as AI reshapes digital marketing.
Whether you're an entrepreneur, creator, or future business owner, this episode gives you a roadmap to scale smarter—not harder—while building a life you actually want to live.
WHAT WE COVER
- The truth behind why most startups fail before year one
- Greg’s mission beyond money—and what drives him today
- The mindset he developed growing up and how it shaped his success
- The biggest structural mistakes founders make when launching in 2025
- The key criteria Greg looks for when investing in or backing a startup
- How to transition from founder to CEO and build a self-managing company
- The marketing skills that now matter most in the era of AI and attention
- What metrics actually matter for real growth (no vanity metrics)
- How founders should think about investing—personally and professionally
- Listener question: “What’s the most important skill to become the best salesman?”
- Greg’s advice to his younger entrepreneurial self
DISCLAIMER
This conversation is for educational purposes only. We are not financial advisors. Always seek professional advice before making financial decisions.
Watch on YouTube: The Growth Concept - YouTube!
43 episodes
