Designed to GlideWell

Sarah & Ethan Glidewell
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Designed to GlideWell is a podcast about building a life—and business—by design. Hosted by husband-and-wife duo Sarah and Ethan Glidewell, this show takes you behind the scenes of what it really looks like to build wealth and freedom through unconventional paths. From buying and building businesses to investing in and designing high-performing vacation rentals, they share the strategies, lessons, and mindset shifts that have shaped their journey. But this isn’t just about business—it’s about intention. Each episode explores how to create a life that feels as good as it looks, whether that’s through thoughtful design, smart investments, or redefining what success can be beyond the traditional 9–5. Along the way, they sit down with founders, investors, and creatives who are carving out their own paths through unique opportunities and alternative ways of living. If you’ve ever felt like there’s more than the default path—this is your invitation to build it.

  1. 20 Jul

    We Were Wrong About Airbnb. Here's What We Learned After 5 Years.

    Have feedback or a topic you want to hear about, let us know by sending us a direct message! For years, we believed Airbnb investing was the fastest path to building wealth. After renovating multiple properties, navigating changing regulations, spending more than we ever had on our latest lake house, and building businesses alongside real estate... our perspective completely changed. In this episode, we're sharing the lessons we wish someone had told us five years ago. We talk about: • Why we spent 2.5× more on our newest Airbnb, Black Pearl • The luxury upgrades that were actually worth every dollar • The expensive mistakes we'd never make again • Why we're shifting our focus from buying more Airbnbs to building cash-flowing businesses • The truth about real estate, cash flow, taxes, and long-term wealth • Launching Black Pearl and its first booking results • Why we left Michigan and moved to Texas • What's next for us and our businesses This isn't an anti-Airbnb episode. It's an honest conversation about how our mindset has evolved after five years of building, investing, and learning the hard way. If you're an entrepreneur, Airbnb host, real estate investor, or someone trying to build financial freedom, we hope this episode helps you avoid a few of the mistakes we made. 🎙️ Subscribe for more conversations on entrepreneurship, real estate, design, business, and building a life you're proud of. Hosted by Ethan Glidewell & Sarah Glidewell  You can view the video & audio version on our Youtube Channel  Thanks for listening!

  2. 22 Jun

    She Quit Drinking at 22, Built $3M in Real Estate, and Now Says Airbnb Isn't the End Goal.

    Have feedback or a topic you want to hear about, let us know by sending us a direct message! What does success look like after you've already achieved the dream? In this episode of Designed to GlideWell, Sarah sits down with real estate investor and entrepreneur Zoe Burgoff to talk about the journey from renting out a simple yurt on Airbnb to building over $3 million in equity in just a few years. But this conversation goes far beyond short-term rentals. Zoe shares how quitting alcohol at 22 changed the trajectory of her life, why she and her husband ignored trends and built wealth their own way, the realities of raising a child while developing real estate projects, and the surprising question many successful Airbnb investors are asking themselves today: "What's next?" Whether you're building a business, investing in real estate, navigating parenthood, or simply trying to create a life aligned with your values, this episode is packed with honest insights on discipline, lifestyle design, long-term wealth, and staying true to your own path. 🎙 In this episode:  • How a $16,000 yurt launched a real estate empire  • Building $3M+ in equity without chasing trends  • Why sobriety became a competitive advantage  • The truth about Airbnb in 2026  • Parenting, entrepreneurship, and creating freedom by design  • Why successful investors are looking beyond short-term rentals If you've ever wondered what happens after you "make it," this conversation is for you. Hosted by Ethan Glidewell & Sarah Glidewell  You can view the video & audio version on our Youtube Channel  Thanks for listening!

  3. 8 Jun

    The Ugly Truth About Entrepreneurship Nobody Talks About

    Have feedback or a topic you want to hear about, let us know by sending us a direct message! Everyone sees the beautiful photos, successful businesses, and dream lifestyle. What they don't see are the sleepless nights, late rent payments, maxed-out budgets, relationship stress, and constant fear of failure. In this episode, Madi and Skyler from For The Love of Upstate share the raw truth behind building an 8-property short-term rental portfolio, working as a couple, managing investor money, and sacrificing comfort to chase a dream. We talk about:  ✨ The reality behind "Instagram success"  ✨ Entrepreneurship vs. a traditional 9-5  ✨ Building a business with your partner  ✨ The pressure of managing other people's money  ✨ Why they almost wouldn't do it again  ✨ The advice they'd give their younger selves  ✨ The mindset that kept them going when things got hard If you've ever thought about quitting your job, starting a business, investing in real estate, or chasing a dream that feels bigger than you, this conversation is for you. Hosted by Ethan Glidewell & Sarah Glidewell  You can view the video & audio version on our Youtube Channel  Thanks for listening!

    The Ugly Truth About Entrepreneurship Nobody Talks About

  4. 26 May

    The Truth About Freedom, Burnout & Building a Life You Actually Want.

    Have feedback or a topic you want to hear about, let us know by sending us a direct message! What does freedom actually look like after you leave the 9–5? In this episode, we sit down with Cassidy & Aaron for one of the most honest conversations we’ve had yet about entrepreneurship, burnout, relationships, identity, health, social media, Airbnb investing, and building a life that actually feels good to live. From quitting corporate jobs and living in a van, to building a real estate portfolio and navigating the pressure of constantly chasing “more,” this conversation dives deep into the reality behind the dream life people see online. We talk about:  — Leaving corporate burnout behind  — Building a business with your partner  — Codependency in entrepreneurship  — Fitness, sobriety & identity shifts  — Why social media changed their lives  — Feeling guilty after achieving freedom  — Airbnb investing in today’s market  — AI, creativity & the future of business  — Learning how to slow down and enjoy the life you worked for This episode is for anyone who feels stuck between ambition and peace… and is trying to figure out how to build both.  Hosted by Ethan Glidewell & Sarah Glidewell  You can view the video & audio version on our Youtube Channel  Thanks for listening!

    The Truth About Freedom, Burnout & Building a Life You Actually Want.

  5. 11 May

    From Survival Mode to Multiple Businesses in 3 Years

    Have feedback or a topic you want to hear about, let us know by sending us a direct message! What happens when you leave everything behind, move to a new country with almost nothing, and bet on yourself anyway? In this episode, Fede and Caro share their raw journey from Argentina to America — from making $3.50 an hour and cleaning apartments for cash, to building multiple businesses in just a few years. They open up about entrepreneurship, ADHD, AI, creativity, risk-taking, scarcity mindset, and why they still believe the American Dream is alive. This conversation dives deep into:  Building businesses from the ground up  The reality behind hustle culture  Neurodivergence as a superpower  Why creativity may survive AI  The mindset shift that changed everything  Immigrant perspective on opportunity in America  Mental health, fear, ambition & resilience A real, honest conversation about what it actually takes to create a life you once only imagined.  Hosted by Ethan Glidewell & Sarah Glidewell  You can view the video & audio version on our Youtube Channel  Thanks for listening!

  6. 29 Apr

    We thought 10 Airbnbs would make us rich… turns out, one business could do it faster.

    Have feedback or a topic you want to hear about, let us know by sending us a direct message! This episode dives into a major mindset and strategy shift—from building wealth through Airbnb and real estate to focusing on acquiring cash-flowing businesses. The hosts reflect on their journey: starting with short-term rentals as a path to financial freedom, only to realize that real estate—while valuable—is slower, capital-intensive, and heavily reliant on equity rather than immediate income. After conversations with mentors and analyzing real numbers, they uncover a key insight: buying established businesses can generate significantly higher and faster cash flow than building or scaling real estate portfolios. They break down:  Why many investors are pivoting from real estate to business acquisition  The difference between being “equity-rich” vs. “cash-flow rich”  How buying an existing business removes the grind of starting from zero  The surprising opportunities in “boring” service-based businesses (like plumbing, street sweeping, etc.)  The impact of AI on jobs—and why owning businesses may be the safest long-term move The episode also highlights the power of social media in creating unexpected opportunities and emphasizes a key mindset shift:  👉 You don’t need to know everything—you just need to be willing to lead and figure it out. Overall, it’s a raw, honest conversation about evolving financial strategies, risk, and building wealth in a rapidly changing economy. Hosted by Ethan Glidewell & Sarah Glidewell  You can view the video & audio version on our Youtube Channel  Thanks for listening!

  7. 13 Apr

    Are We Going To Jail? (How We Got Here Pt. 2)

    Have feedback or a topic you want to hear about, let us know by sending us a direct message! In Episode 2 of Designed to Glidewell, we’re continuing the story—and this is where things get even more real. Just as we started to find our footing in the Airbnb world, everything shifted. Regulations tightened. Neighbors started paying attention. And what once felt like momentum quickly turned into legal battles we never saw coming. We’re sharing what it actually looked like to navigate lawsuits, deal with the pressure of community pushback, and make the difficult decision to sell some of our properties. This episode is about more than just real estate—it’s about risk, resilience, and the parts of entrepreneurship that no one talks about. The moments where you’re forced to pivot, protect what you’ve built, and decide what’s worth fighting for. If you’ve ever wondered what happens when things don’t go according to plan—or how to move forward when they really fall apart—this one is for you. Hosted by Ethan Glidewell & Sarah Glidewell  You can view the video & audio version on our Youtube Channel  Thanks for listening!

  8. 13 Apr

    Was Getting Robbed a Blessing? (How Did We Get Here)

    Have feedback or a topic you want to hear about, let us know by sending us a direct message! In this episode of Designed to Glidewell, we’re taking it back to the beginning. We’re introducing ourselves—who we are, what we’ve built, and why this podcast is evolving into something deeper and more intentional. From the outside, our journey into business ownership and vacation rental investing might look smooth… but the reality was anything but. We’re sharing what it looked like to invest our first $20K into Airbnb properties that launched right before the world shut down—when everything we thought would work… didn’t. From struggling bookings to one of our units being completely robbed, this episode is a raw look at the moments that could have taken us out. But they didn’t. We talk about how we navigated those setbacks, rebuilt from the ground up, and ultimately created a portfolio and business model that performs at a completely different level today. If you’re in the messy middle, questioning if it’s worth it, or wondering how people actually recover when things go wrong—this episode is for you. Hosted by Ethan Glidewell & Sarah Glidewell  You can view the video & audio version on our Youtube Channel  Thanks for listening!

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About

Designed to GlideWell is a podcast about building a life—and business—by design. Hosted by husband-and-wife duo Sarah and Ethan Glidewell, this show takes you behind the scenes of what it really looks like to build wealth and freedom through unconventional paths. From buying and building businesses to investing in and designing high-performing vacation rentals, they share the strategies, lessons, and mindset shifts that have shaped their journey. But this isn’t just about business—it’s about intention. Each episode explores how to create a life that feels as good as it looks, whether that’s through thoughtful design, smart investments, or redefining what success can be beyond the traditional 9–5. Along the way, they sit down with founders, investors, and creatives who are carving out their own paths through unique opportunities and alternative ways of living. If you’ve ever felt like there’s more than the default path—this is your invitation to build it.

Information

  • Creator
    Sarah & Ethan Glidewell
  • Years Active
    2022 - 2026
  • Episodes
    98
  • Rating
    Explicit
  • Copyright
    © 2026 Designed to GlideWell
  • Show Website
    Designed to GlideWell

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