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.
How To Ride A Roller Coaster
Claim This Podcastby David Ezell
5.0(3 reviews)
95 episodes
Updated Weekly
Accepts GuestsHas SponsorsLocation 🇺🇸
55
Podcast Authority
BetaFairBased on show quality, social media presence, reviews, charts, and more
Quality52
Social0
YouTube76
Engagement71
Podcast Overview
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.
Language
🇺🇲
Publishing Since
3/15/2019
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55
Podcast Authority
BetaFairBased on show quality, social media presence, reviews, charts, and more
Quality52
Social0
YouTube76
Engagement71
7
Excellent Areas
2
Good Performance
10
Growth Opportunities
excellent
Episode Length
41 minutes
Performing excellently!
good
Show Notes Quality
3.0/5
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needs improvement
Publishing Consistency
Every 29 days
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Recent Episodes
June 9, 2026
From Gambling Addiction to Multi-Million Dollar CEO | Jay Sapovitz on Reinvention, Recovery & Entrepreneurship
<p>What happens when you hit rock bottom and have to rebuild everything?</p><p>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.</p><p>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.</p><p>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.</p><p>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.</p><p>Connect with Jay:</p><p>LInkedIn: https://www.linkedin.com/in/jaysap/</p><p>Ink'd Stores: https://inkdstores.com/</p><p><br></p><p>#Entrepreneurship #BusinessPodcast #StartupLife #Leadership #Recovery #SmallBusiness #FounderStory #PersonalGrowth #BusinessOwner #HowToRideARollerCoaster</p>
April 7, 2026
From Flatlining to $40M Exit: Draye Redfern on Fixing Broken Marketing & Scaling Smarter
<p>What happens when your life flatlines… and it completely changes how you see business?</p><p>In this episode of How to Ride a Roller Coaster, I sit down with <strong>Draye Redfern, </strong>former professional cyclist turned entrepreneur who has built, scaled, and exited multiple companies (including a $40M+ sale to Berkshire Hathaway).</p><p>But this isn’t just a success story.</p><p>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.</p><p>We break down:</p><ul><li>Why most marketing feels like “throwing money into a hole”</li><li>The biggest mistakes businesses make at each revenue stage</li><li>How to actually build a scalable marketing system (not guesswork)</li><li>Why direct mail might outperform social media right now</li><li>The truth about vanity metrics and fake “online success”</li><li>How AI is changing marketing—and what to do about it today</li><li>The leadership shift from operator to owner</li></ul><p>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.</p><p><br></p><p><u><strong>Links: </strong></u></p><p>Listen / Subscribe to the show:<br><a href="https://podcasts.apple.com/us/podcast/how-to-ride-a-roller-coaster/id1456618718" target="_new" rel="noopener">https://podcasts.apple.com/us/podcast/how-to-ride-a-roller-coaster/id1456618718</a></p><p>Connect with David Ezell:</p><ul><li>LinkedIn: <a href="https://www.linkedin.com/in/davidezell" target="_new" rel="noopener">https://www.linkedin.com/in/davidezell</a></li><li>Website: <a href="https://realdavidezell.com" target="_new" rel="noopener">https://realdavidezell.com</a></li></ul><p>Connect with Draye Redfern:</p><ul><li>LinkedIn: <a href="https://www.linkedin.com/in/davidezell">https://www.linkedin.com/in/drayeredfern/</a></li></ul><p><br></p><p><u><strong>Timestamps:</strong></u></p><ul><li>00:00 – Intro & Draye’s background</li><li>03:30 – The health scare that changed everything</li><li>12:15 – Transition into entrepreneurship</li><li>18:40 – Selling a business to Berkshire Hathaway</li><li>25:10 – Common marketing mistakes (7–8 figure companies)</li><li>35:20 – The “1s and 3s” growth framework</li><li>42:00 – Why direct mail still works</li><li>50:30 – Content strategy + AI opportunity</li><li>1:02:00 – Leadership lessons & delegation</li><li>1:10:00 – Advice to younger entrepreneurs</li></ul><p><br></p><p><u><strong>Tags:</strong></u></p><p>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</p><p><br></p>
January 28, 2026
From the Sidelines to the CEO Seat: Building Leadership, Visibility, and Belief in Youth Sports | Hannah Howard of Rematch
<p>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.</p><p>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.</p><p>We dive deep into:</p><ul><li><p>The transition from athlete and coach to CEO</p></li><li><p>How sports leadership translates to business leadership</p></li><li><p>Why youth sports visibility matters beyond recruiting</p></li><li><p>How Rematch uses AI to capture meaningful moments in real time</p></li><li><p>The fragmented nature of the U.S. youth sports market</p></li><li><p>Building teams through vision, trust, and transformation</p></li></ul><p>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.</p><p>🎧 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.</p><p><br></p><p>Show links:</p><p><a href="https://www.linkedin.com/in/hhoward25/" target="_blank" rel="noopener noreferer">Hannah on LinkedIn</a></p><p><a href="https://www.rematch.tv/us/" target="_blank" rel="noopener noreferer">Rematch</a></p><p><a href="https://www.greatnessthebook.com/" target="_blank" rel="noopener noreferer">Greatness book</a></p>
95 total episodes available with 1 transcripts
Recent guests on How To Ride A Roller Coaster
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Elina Panteleyeva
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Jeff Hancher
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Zach Tsakiris
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This podcast updates weekly.
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This podcast is available on 9 platforms including Apple Podcasts, Spotify, and more. You can also use the RSS feed directly.
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