How To Ride A Roller Coaster

David Ezell
  • 5.0 (9)
  • Marketing
  • Weekly

Building a brand is one thing. Evolving it is another. How To Ride A Roller Coaster explores the strategies, decisions, and challenges behind building, managing, and transforming brands. Hosted by brand strategist David Ezell, each episode features candid conversations with industry leaders about brand strategy, architecture, mergers and acquisitions, integration, governance, and building lasting brand equity. Because building a great brand isn't just about how it looks. It's about how it works.

  1. Oct 15

    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 How to Ride a Roller Coaster explores the challenges, decisions, and lessons that shape the entrepreneurial journey.

  2. Jun 9

    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

  3. Apr 7

    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 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/id1456618718 Connect 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 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

  4. Jan 28

    From the Sidelines to the CEO Seat: Building Leadership, Visibility, and Belief in Youth Sports | Hannah Howard of Rematch

    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

  5. 12/16/2025

    The Hidden Tax Mistakes That Kill E-Commerce Businesses (and How to Avoid Them)

    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 correctly How 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 exit What’s changing next for digital products and services taxation When 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/

  6. 11/26/2025

    Episode #91: Lacy Garcia, Co-Founder and CEO of Willow

    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 identity Why separating your personal and business finances is non-negotiable as a founder How to protect your energy and avoid burning yourself out while building something meaningful The hard lesson of focusing on revenue and efficiency first, not perfection Whether 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.com Lacy on LinkedIn: https://www.linkedin.com/in/lacygarcia Willow on Instagram: https://instagram.com/trustwillow Today'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.com IG: https://instagram.com/clutchcityhq More at: https://realdavidezell.com/clutchcity If 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.

  7. 11/19/2025

    Episode #90: Amanda Taylor, Founder of Expand Your Empire

    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 growth Why most business owners neglect their personal wealth — and what it costs them The difference between good debt and bad debt (and why debt is often cheaper than equity) Why liquidity fears hold entrepreneurs back How women can close the confidence gap in financial decision-making Where beginners should start investing outside their business Why traditional financial advice leaves entrepreneurs exposed — and what to do instead The power of aligning your money with the life you actually want If 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 LinkedIn Amanda on Instagram Expand Your Empire Powered 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.

  8. 11/11/2025

    Episode #89: Perry Sheraw, Managing Partner at Duma Marketing

    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 dashboard Building automations that feel human — from welcome emails to onboarding flows The psychology behind customer trust and why email still outperforms social New frontiers in automation, including WhatsApp integration and conversational AI How to “turn the lights on” in your marketing house — and stop losing leads you’ve already paid for Whether 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.com High-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

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About

Building a brand is one thing. Evolving it is another. How To Ride A Roller Coaster explores the strategies, decisions, and challenges behind building, managing, and transforming brands. Hosted by brand strategist David Ezell, each episode features candid conversations with industry leaders about brand strategy, architecture, mergers and acquisitions, integration, governance, and building lasting brand equity. Because building a great brand isn't just about how it looks. It's about how it works.

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