What happens when you hit rock bottom and have to rebuild everything?

In this episode of How to Ride a Roller Coaster, David Ezell sits down with entrepreneur and Inked Stores founder Jay Sapovitz to discuss the highs, lows, and hard truths behind building a successful business and life.

Before becoming the CEO of a multi-million-dollar company, Jay battled a gambling addiction that nearly cost him everything. After walking away from a promising career and starting over from scratch, he rebuilt his future through discipline, honesty, resilience, and entrepreneurship.

Jay shares the lessons he's learned from recovery, launching multiple businesses, navigating failure, leading teams, surviving COVID pivots, and scaling Inked Stores into a thriving e-commerce brand.

Whether you're an entrepreneur, business leader, founder, or someone navigating a difficult chapter, this conversation is packed with practical wisdom about perseverance, growth, and what it really takes to succeed.

Connect with Jay:

LInkedIn: https://www.linkedin.com/in/jaysap/

Ink'd Stores: https://inkdstores.com/

#Entrepreneurship #BusinessPodcast #StartupLife #Leadership #Recovery #SmallBusiness #FounderStory #PersonalGrowth #BusinessOwner #HowToRideARollerCoaster

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

Hannah Howard is a former Division I athlete and Power Five head coach who has made the leap from elite college athletics into tech leadership as the CEO of Rematch U.S.

In this episode of How to Ride a Roller Coaster, Hannah shares her journey from the court to the boardroom, including what it means to lose your first professional dream, how coaching is really running a business, and why leadership requires stepping into uncertainty long before clarity shows up.

We dive deep into:

• The transition from athlete and coach to CEO

• How sports leadership translates to business leadership

• Why youth sports visibility matters beyond recruiting

• How Rematch uses AI to capture meaningful moments in real time

• The fragmented nature of the U.S. youth sports market

• Building teams through vision, trust, and transformation

This conversation goes beyond technology and tactics. It’s about identity, belief, and what happens when you’re willing to enter the arena, even when the outcome isn’t guaranteed.

🎧 Whether you’re an entrepreneur, a former athlete, a parent in youth sports, or a leader navigating your next chapter, this episode is for you.

Show links:

Hannah on LinkedIn

Rematch

Greatness book