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How To Ride A Roller Coaster is the official podcast of Clutch City. Each episode brings you honest, tactical conversations with founders navigating the highs and lows of entrepreneurship – from wild pivots to clutch wins.
What happens when your life flatlines… and it completely changes how you see business?
In this episode of How to Ride a Roller Coaster, I sit down with Draye Redfern, former professional cyclist turned entrepreneur who has built, scaled, and exited multiple companies (including a $40M+ sale to Berkshire Hathaway).
But this isn’t just a success story.
Draye shares how a near-death experience, and later a career-ending accident, forced him to rethink everything. That shift led him into entrepreneurship, where he now helps 7- and 8-figure businesses fix broken marketing systems and scale smarter.
We break down:
- Why most marketing feels like “throwing money into a hole”
- The biggest mistakes businesses make at each revenue stage
- How to actually build a scalable marketing system (not guesswork)
- Why direct mail might outperform social media right now
- The truth about vanity metrics and fake “online success”
- How AI is changing marketing—and what to do about it today
- The leadership shift from operator to owner
This episode is packed with practical insights, but also a powerful reminder: Sometimes the hardest moments in your life are the ones that set everything in motion.
Links:
Listen / Subscribe to the show:
https://podcasts.apple.com/us/podcast/how-to-ride-a-roller-coaster/id1456618718
Connect with David Ezell:
- LinkedIn: https://www.linkedin.com/in/davidezell
- Website: https://realdavidezell.com
Connect with Draye Redfern:
Timestamps:
- 00:00 – Intro & Draye’s background
- 03:30 – The health scare that changed everything
- 12:15 – Transition into entrepreneurship
- 18:40 – Selling a business to Berkshire Hathaway
- 25:10 – Common marketing mistakes (7–8 figure companies)
- 35:20 – The “1s and 3s” growth framework
- 42:00 – Why direct mail still works
- 50:30 – Content strategy + AI opportunity
- 1:02:00 – Leadership lessons & delegation
- 1:10:00 – Advice to younger entrepreneurs
Tags:
entrepreneurship, marketing strategy, scaling a business, fractional CMO, business growth, marketing mistakes, startup marketing, AI marketing, brand strategy, leadership, business systems, digital marketing vs direct mail, scaling to 7 figures, scaling to 8 figures