From Flatlining to $40M Exit: Draye Redfern on Fixing Broken Marketing & Scaling Smarter

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 itThe hidden risks of building a company that depends entirely on youHow to recognize when it's time to sellWhy some entrepreneurs wait too long to exitThe financial mistakes that can cost owners hundreds of thousands of dollarsWhat business owners can do today to build long-term valueWhether 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.comHow to Ride a Roller Coaster explores the challenges, decisions, and lessons that shape the entrepreneurial journey.

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 stageHow to actually build a scalable marketing system (not guesswork)Why direct mail might outperform social media right nowThe truth about vanity metrics and fake “online success”How AI is changing marketing—and what to do about it todayThe leadership shift from operator to ownerThis 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/id1456618718Connect with David Ezell:LinkedIn: https://www.linkedin.com/in/davidezellWebsite: https://realdavidezell.comConnect with Draye Redfern:LinkedIn: https://www.linkedin.com/in/drayeredfern/Timestamps:00:00 – Intro & Draye’s background03:30 – The health scare that changed everything12:15 – Transition into entrepreneurship18:40 – Selling a business to Berkshire Hathaway25:10 – Common marketing mistakes (7–8 figure companies)35:20 – The “1s and 3s” growth framework42:00 – Why direct mail still works50:30 – Content strategy + AI opportunity1:02:00 – Leadership lessons & delegation1:10:00 – Advice to younger entrepreneursTags: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 CEOHow sports leadership translates to business leadershipWhy youth sports visibility matters beyond recruitingHow Rematch uses AI to capture meaningful moments in real timeThe fragmented nature of the U.S. youth sports marketBuilding teams through vision, trust, and transformationThis 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 LinkedInRematchGreatness book

Selling online feels simple... until taxes quietly start working against you.In this episode of How to Ride a Roller Coaster, host David Ezell sits down with Jared Smithson, Founder of RJM Tax Exemption and one of the leading experts in U.S. e-commerce tax compliance. Jared has helped over 5,000 businesses navigate sales tax, multi-state nexus, and regulatory landmines that most founders don’t realize they’ve stepped on until it’s too late.You’ll learn:The most common sales tax mistakes e-commerce founders make (including the “one-click” Shopify error)Why revenue growth can be fake growth if compliance isn’t handled correctlyHow economic nexus actually works (and why $100K isn’t the only number that matters)Why collected sales tax isn’t “your money”—and how it can block an exitWhat’s changing next for digital products and services taxationWhen to DIY vs. when to bring in experts (without wasting money)Whether you’re selling on Shopify, Amazon, Walmart, or planning to expand into the U.S. market, this conversation could save you six figures, months of stress, and a painful audit.Show links:RJM Tax Exemption: https://rjmtaxexemption.com/Jared: https://www.linkedin.com/in/jared-smithson-692607228/

Finance isn’t just numbers. It’s identity, access, and peace of mind. Yet so many women, millennials, Gen-Z professionals, and underserved investors feel invisible in the world of wealth management. Today’s episode shines a spotlight on changing that.I’m joined by Lacy Garcia, CEO and Cofounder of Willow, a fintech platform that matches individuals with fiduciary financial advisors who actually get them. Lacy left a stable career, survived the chaos of launching during COVID, and built a platform dedicated to empathy, education, and empowerment in financial planning.We dig into:The shame-free truth about financial literacy (even highly educated people don’t know this stuff!)How to find an advisor who understands YOUR values, goals, and identityWhy separating your personal and business finances is non-negotiable as a founderHow to protect your energy and avoid burning yourself out while building something meaningfulThe hard lesson of focusing on revenue and efficiency first, not perfectionWhether you’re growing a business, building wealth, or just trying to make smarter financial decisions, this episode will save you time, money, and serious stress.Show links:Willow: https://trustwillow.comLacy on LinkedIn: https://www.linkedin.com/in/lacygarciaWillow on Instagram: https://instagram.com/trustwillowToday's episode is sponsored by Clutch City, a bold, high-impact experience for entrepreneurs scaling real businesses between $250K and $3M.Clutch City: https://www.clutchcityhq.comIG: https://instagram.com/clutchcityhqMore at: https://realdavidezell.com/clutchcityIf you loved today’s episode, share it with a founder who needs clarity on money or is tackling their next big leap. One episode can change someone’s week.

In this episode of How to Ride a Roller Coaster, David Ezell sits down with Amanda Taylor — entrepreneur, real estate investor, and bold money mindset coach — to talk about what it really looks like to rewrite your story.After 15 years in dentistry and walking away from a 25-year relationship, Amanda completely rebuilt her life. She discovered freedom through real estate, launched multiple businesses, and now helps entrepreneurs—especially women—grow both their companies and their personal wealth.Together, we unpack:The moment Amanda realized she could stop being the “worker bee” and step into the “queen bee”How curiosity, not confidence, accelerates your entrepreneurial growthWhy most business owners neglect their personal wealth — and what it costs themThe difference between good debt and bad debt (and why debt is often cheaper than equity)Why liquidity fears hold entrepreneurs backHow women can close the confidence gap in financial decision-makingWhere beginners should start investing outside their businessWhy traditional financial advice leaves entrepreneurs exposed — and what to do insteadThe power of aligning your money with the life you actually wantIf you’re an entrepreneur trying to build a business and build wealth at the same time, this episode will change how you think about money forever.Show links:Amanda on LinkedInAmanda on InstagramExpand Your EmpirePowered by Clutch City — high-energy training, hands-on events, curated rooms, and one immersive conference each year for entrepreneurs in the $250k–$3M range who want to scale faster and smarter.

In this episode of How to Ride a Roller Coaster, host David Ezell sits down with Perry Sheraw — a pioneer in marketing automation and customer experience strategy. Long before tools like HubSpot and Klaviyo became industry staples, Perry was building CRM systems from scratch, connecting call centers to digital marketing, and architecting the early blueprints of what we now call customer journey design.Together, David and Perry explore how founders and teams can bridge the gap between marketing and sales, transform chaos into consistency, and design systems that build trust over time — not just conversions. They dig into:Why marketing and sales silos still exist (and how to break them)How to map your customer journey using a whiteboard, not a dashboardBuilding automations that feel human — from welcome emails to onboarding flowsThe psychology behind customer trust and why email still outperforms socialNew frontiers in automation, including WhatsApp integration and conversational AIHow to “turn the lights on” in your marketing house — and stop losing leads you’ve already paid forWhether you’re an entrepreneur trying to scale your first system or a marketing leader rethinking automation strategy, this episode offers a grounded, tactical approach to customer-centric growth.Perry Sheraw is a strategist, consultant, and speaker specializing in marketing automation and customer experience frameworks. She’s led marketing and call center operations for highly regulated industries, built cross-functional CRM systems, and currently advises companies on scaling automation with empathy. Perry is also writing a forthcoming book on marketing automation frameworks for young professionals — a practical guide on integrating automation and selling it to the C-suite.Learn more at perrysheraw.comShow links:• Connect with Perry on LinkedIn• HubSpot – hubspot.com• Mailchimp – mailchimp.com• Klaviyo – klaviyo.com• Seth Godin – “Permission Marketing”• Neil Patel – neilpatel.comHigh-level takeaways:• “If you invite people to your house and then leave, that’s what it’s like sending paid traffic without follow-up.”• “Automation isn’t about removing the human — it’s about meeting them where they are.”• “Start your customer journey on a whiteboard, not in a platform.”• “Marketing and sales are two halves of the same customer conversation.”🎧 Apple Podcasts | Spotify | YouTube🗞 Subscribe to the Field Notes newsletter for key takeaways from every episode → realdavidezell.com/fieldnotes

What if the smartest business move you ever make… is not to scale?In this episode of How To Ride A Roller Coaster, host David Ezell sits down with Matt Krayton, Founding Principal of Publitics, a communications and political strategy firm that helps leaders, organizations, and public figures navigate high-stakes challenges, shape public opinion, and build trust in an age of polarization.Matt shares his unconventional path—from a laid-off history teacher to launching his own political consulting firm during the 2008 recession—and how choosing to stay small became his biggest competitive advantage.Together, David and Matt unpack the tension between growth and purpose, what it really means to be nimble in business, and how founders can build lasting success without losing their freedom or values.They dig into:The real story behind founding Publitics and breaking into political consultingWhy staying small and agile beats scaling for scale’s sakeHow taking investor money can change your mission overnightThe “SWAT team” approach to problem-solving in high-pressure industriesHow to craft messages that resonate across fragmented media platformsWhy attention is the new currency—and how to earn it authenticallyWhat entrepreneurs can learn from political campaigns about narrative, focus, and resilienceThis episode is a masterclass in intentional growth, narrative strategy, and the power of staying true to your mission—even when everyone else is telling you to go bigger, faster, and louder.If you’ve ever wondered whether more is really better, this conversation will give you the clarity to redefine success on your own terms.Show links:Matthew on LinkedIn: https://www.linkedin.com/in/mkrayton/Publitics: https://www.publitics.com/M2Aspire: https://www.m2aspire.com/Substack: https://m2aspire.substack.com/

What if the key to higher performance wasn’t working harder — but understanding your brain?In this episode of How To Ride A Roller Coaster, host David Ezell talks with Dr. Eugene Choi, a neuroscience-based executive coach and former LA County health system leader who managed operations for six major hospitals and over 250 clinics. After witnessing burnout and pressure derail even the most talented teams, Eugene set out to uncover why — and discovered how our brains can be retrained to operate in peak performance mode.Together, David and Eugene explore:🧠 The neuroscience behind leadership burnout (and how to fix it)⚡ How to trigger “flow state” on demand — even under pressure👥 How high-performing teams can unlock clarity, creativity, and engagement🔄 Practical brain-based tools entrepreneurs can use to perform better without burning outIf you’ve ever hit a wall in your business, this conversation will help you understand what’s happening under the hood — and how to rewire it.Website → https://eugenekchoi.com/LinkedIn → https://www.linkedin.com/in/eugenekchoi/Connect with David:Website → https://realdavidezell.comListen to past episodes, discover upcoming guests, and get resources for founders and creators navigating the highs and lows of entrepreneurship.