Designed to GlideWell

Hosted by Sarah & Ethan Glidewell

Business Investing Arts Design

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Latest episode

Jun 2026

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EN-US

About the show

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.

Listen to episodes

60 recent

June 8, 2026Episode 637 min

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 hardIf 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!

May 26, 2026Episode 51 hr 22 min

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 forThis 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!

May 11, 2026Episode 455 min

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!

April 29, 20261 hr 2 min

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!

April 13, 2026Episode 21 hr 25 min

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!

April 13, 2026Episode 157 min

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!

October 30, 2025Episode 2259 min

Is It Time to Say Goodbye to KarWells and Embrace a New Chapter?

Have feedback or a topic you want to hear about, let us know by sending us a direct message!After five incredible years, we're sitting down together for the FINAL episode of The KarWell Chronicles. From late-night hustle sessions to heartfelt retreats, we've weathered every up and down—and now, we're turning the page to new chapters in our lives. Get ready for honest stories, behind-the-scenes confessions, and lots of laughs (and maybe a few tears), as we talk friendship, business breakups, motherhood, and what truly matters most. If you’ve ever wondered what it’s really like to build something special with your best friend, navigate the wild ride of entrepreneurship, or make the hard decisions when passions and realities change—this episode is for you. Whether you’re an OG listener or finding us for the first time, we’re so grateful you’re here.Join us for reflections on our biggest lessons, the legacy we hope to leave, and a look ahead at what’s next (hint: family, new businesses, and even more personal growth). Plus, you’ll hear empowering takes on trusting your gut, protecting your friendships, and unapologetically choosing YOURSELF.Don’t miss the finale to five years of laughter, learning, and friendship. Hit play and leave us a comment with your favorite KarWell Chronicles moment!TIMECODES:00:01:58 – Life Changes: Why We’re Closing This Chapter (& The Big Announcements!)00:13:30 – Overcoming Guilt & Embracing the Stay-at-Home Mom Journey00:32:40 – The Power of Community: Our Final Retreat Reflections00:46:08 – Business Peaks & Pits: Lessons from Saying Yes & No00:52:45 – Friendship First: How We Kept Our Bond Through It All👉 Subscribe for more on entrepreneurship, personal growth, and navigating transitions with heart. Follow us on Instagram for life updates, future projects, and everything that comes next.Instagram: @sarahkarwell@emkarwell@thekarwellsTHANK YOU for being part of our journey. This isn’t goodbye… it’s see you later. 💛#TheKarWellChronicles #BestFriendBusiness #Entrepreneurship #MomLife #Transition #PodcastFinale #WomenSupportingWomenHosted by Ethan Glidewell & Sarah Glidewell You can view the video & audio version on our Youtube Channel Thanks for listening!

October 15, 2025Episode 2159 min

From Solopreneurs to Acquisition Entrepreneurs: A Game-Changing Journey

Have feedback or a topic you want to hear about, let us know by sending us a direct message!Welcome back to The KarWell Chronicles! In this episode, Sarah and Ethan dive deep into the mindset shifts that transformed their entrepreneurial journey—from building businesses from scratch to embracing the powerful strategy of buying established companies. 🚀We peel back the curtain on real-world statistics that will change the way you think about risk, success, and failure in entrepreneurship. Why do most solopreneurs hit a ceiling? How do you build for an exit instead of getting stuck wearing every hat? And what about stepping out of your comfort zone, overcoming limiting beliefs, and restructuring your entire life (including going alcohol-free!) to become the leader you were meant to be?Whether you're a seasoned business owner, a budding entrepreneur, or just curious about personal growth and leveling up your circle, this transparent, no-BS conversation will open your eyes, motivate you, and maybe even make you laugh. Plus, we talk about the journey as a couple: what it means to truly partner with an A-player and why surrounding yourself with the right people is non-negotiable.🔥 If you’ve ever wondered whether you’re building your business right, how to escape burnout, or if you’re simply ready for a new perspective—hit play now!🎯 KEY MOMENTS (Timestamps):00:05:19 — The Turning Point: From Building to Buying Businesses & Mindset Shifts 00:06:30 — Eye-Opening Stats: Why Buying Beats Building (And Failure Rates that Shock) 00:15:10 — Leadership Unleashed: Why Solopreneurs Get Stuck & The Power of Teams 00:22:29 — Breaking Limiting Beliefs: Big Loans, SBA Secrets, and Taking Massive Leaps 00:43:55 — Going Alcohol-Free: Reinventing Your Identity for Greater Success & Leadership 👇 Tell us in the comments: What’s YOUR biggest entrepreneurial mindset shift? Ready to buy, build, or both? Don’t forget to Like, Subscribe, and Share if you found this valuable. #Entrepreneurship #BusinessMindset #KarWellChronicles #BusinessAcquisition #Leadership #PersonalGrowth #BuyNotBuild #Solopreneur #APlayer #SuccessMindset #LifeByDesignHosted by Ethan Glidewell & Sarah Glidewell You can view the video & audio version on our Youtube Channel Thanks for listening!

September 24, 2025Episode 2057 min

How Can We Foster Respectful Dialogue in a Polarized World?

Have feedback or a topic you want to hear about, let us know by sending us a direct message!On this episode of The KarWell Chronicles, Emily and Sarah dive deep into the current state of the world, navigating tough conversations about politics, free speech, cancel culture, social media, and the importance of open, honest dialogue—especially during turbulent times. They grapple with the public’s response to the recent assassination of Charlie Kirk, the internet’s loud reactions, and how society is dealing with disagreement in an age of polarization. Along the way, they share personal anecdotes, the challenges of raising thoughtful children, and the struggle to hold space for differing beliefs within their circles. If you’re craving raw, unfiltered conversation about humanity, empathy, navigating the echo chambers of today’s media, and how to foster real community even when opinions clash—this episode is for you.Whether you’re exhausted by social media outrage, worried about free speech, or just want to hear two friends wrestle with the gray areas of modern life, tune in for an honest, vulnerable look at what it means to (imperfectly) try to live with love and conviction in a divided world.🌎 No topic is off limits—expect everything from travel dreams, parenting fears, and media responsibility to conspiracy theories and being “cancelled” for unpopular opinions. Plus, hear about the upcoming Cardwell Chronicles retreat and why civil, in-person conversation with people who disagree matters now more than ever.👇 Join the discussion in the comments—respectfully, please!✨ Key Timestamps:00:11:03 – Social Media, Free Speech & Cancel Culture: Navigating When to Speak Up and When to Scroll Past 00:12:43 – The Charlie Kirk Assassination: Impact, Reactions, and Why It Hit So Hard 00:19:26 – The Disappearing Middle: Tug-of-war, Echo Chambers, & Losing Civil Debate 00:38:06 – Cancel Culture on the Right: Are We Just Silencing Each Other? 00:49:53 – Privilege & Perspective: Why Travel Reminds Us How Lucky We AreDon’t forget to subscribe, leave a comment if this episode resonated, and check out the details for the upcoming retreat—a space where real, respectful conversations thrive!Hosted by Ethan Glidewell & Sarah Glidewell You can view the video & audio version on our Youtube Channel Thanks for listening!

September 10, 2025Episode 1957 min

The Best Strategies for Managing Contractors and Renovation Projects

Have feedback or a topic you want to hear about, let us know by sending us a direct message!Welcome back to the KarWell Chronicles! In this episode, Sarah and Emily reunite after a busy month apart and dive right into the drama (and hilarity) of life, renovations, Airbnb investing, and navigating the chaos of contractors. From infuriating plumbers and quirky electricians to neighborly "breaking and entering," you won't believe the stories behind the latest lake project and Newaygo flip. Plus, we share the thrilling results of our latest appraisal (spoiler: record-breaking numbers!), tough lessons learned with building teams, why design matters more than you think, and discuss the shifting landscape of Airbnb real estate. If you're interested in behind-the-scenes real estate, female entrepreneurship, and real talk about work, family, and friendship—you can't miss this episode!Don’t forget: Our Cape Cod retreat is coming up soon, and spots are filling fast! Tune in for all the juicy updates and info on how to grab your spot before our special room rate expires.https://thekarwells.space/the-retreat-fall-2025👀 WATCH FOR:Outrageous contractor complaints and how we handle themThe hilarious saga of Keith the ElectricianSerious appraisal wins (despite the naysayers)Unfiltered talk about healthcare, insurance, and advocating for your familyWhat’s going on in the Airbnb investment world right now⏰ HIGHLIGHTED MOMENTS & TIME CODES:00:05:43 — Off-Center Showers, Type A Renovator Problems, and Parental Home Upgrades00:16:01 — Breaking the Appraisal Ceiling: Our Airbnb Surpasses All Expectations00:24:15 — Is the Airbnb Seller’s Market Flipping? New Trends in Short-Term Rentals00:33:32 — Lake House Neighbors Casually Break In… and Admit It00:50:10 — Keith the Electrician’s “It’s a Bad Day, Not a Bad Life” Pep Talk💬 QUESTION FOR YOU: Have you ever had a wild experience with a contractor or renovation project? Drop your craziest story in the comments!👇 Don’t forget to LIKE, SUBSCRIBE, and hit the bell for more KarWell Chronicles! And if you want to join us at our next retreat, get all the info and secure your spot before September 19th! #Airbnb #RenovationStories #EntrepreneurLife #WomenInBusiness #RealEstateInvesting #Podcast #HomeImprovement #KarWellChroniclesHosted by Ethan Glidewell & Sarah Glidewell You can view the video & audio version on our Youtube Channel Thanks for listening!