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.
Is Your Business Really Worth What You Think? | Gregory Kovsky
What makes a business valuable? And how do you know when it's time to walk away?
In this episode of How to Ride a Roller Coaster, David Ezell sits down with Gregory Kovsky, President and CEO of International Business Associates (IBA), a business brokerage firm with more than 4,400 transactions in its history.
With over 300 business sales personally facilitated, Gregory has seen what separates businesses that thrive, scale, and sell from those that struggle to move beyond their founders.
Together, they explore the realities of entrepreneurship, the challenges of letting go, and why building a successful business doesn't always mean building a valuable one.
In this episode:
Why being great at starting a business doesn't mean you're the right person to scale it
The hidden risks of building a company that depends entirely on you
How to recognize when it's time to sell
Why some entrepreneurs wait too long to exit
The financial mistakes that can cost owners hundreds of thousands of dollars
What business owners can do today to build long-term value
Whether you're building your first business, scaling an existing company, or considering your next chapter, this conversation offers a fresh perspective on what it really means to create something valuable.
Connect with Gregory Kovsky:
International Business Associates: https://www.ibainc.com (https://www.ibainc.com/)
How to Ride a Roller Coaster explores the challenges, decisions, and lessons that shape the entrepreneurial journey.
9 Jun 2026
From Gambling Addiction to Multi-Million Dollar CEO | Jay Sapovitz on Reinvention, Recovery & Entrepreneurship
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
7 Apr 2026
From Flatlining to $40M Exit: Draye Redfern on Fixing Broken Marketing & Scaling Smarter
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 (https://podcasts.apple.com/us/podcast/how-to-ride-a-roller-coaster/id1456618718)
Connect with David Ezell:
LinkedIn: https://www.linkedin.com/in/davidezell (https://www.linkedin.com/in/davidezell)
Website: https://realdavidezell.com (https://realdavidezell.com)
Connect with Draye Redfern:
LinkedIn: https://www.linkedin.com/in/drayeredfern/ (https://www.linkedin.com/in/davidezell)
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
Inside a recent episode
Episode #82: Michael Jacobson, CEO of French Florist
Published 24 Aug 2025 · Transcript excerpt
[…] Their flowers are love and even like if you take even if you're not purchasing for just because and you take the culture for what it is today, people are sending happy birthday happy anniversary, even if it's for something sad, like a funeral, you're sending your condolences, but like no matter what the occasion is, sad is happiness, joy, grief, like whatever it is, you're telling the person that you love them when you're sending them flowers. And again, I'm yet to be convinced otherwise. I don't think there's a more powerful human emotion that exists in this planet that's besides love. And that's when I said earlier that we feel very lucky to work in the industry that we're in. […]
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