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:

• LinkedIn: https://www.linkedin.com/in/drayeredfern/

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