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280 - Creating Profitable Short Term Rentals with Kenny Bedwell

Real Estate Investor Growth Network Podcast

Release Date: 12/01/2025

302 - From $5 to Million Dollar Deals: The Mindset That Changes Everything with Elle Anderson show art 302 - From $5 to Million Dollar Deals: The Mindset That Changes Everything with Elle Anderson

Real Estate Investor Growth Network Podcast

302 - From $5 to Million Dollar Deals: The Mindset That Changes Everything with Elle Anderson What if the real reason you’re not making money in real estate… isn’t your deals, your strategy, or your market—but your identity? In this episode, we break down the hidden force silently capping your income and keeping you stuck, even when you’re doing “everything right.” If you’ve ever felt like you’re working harder but getting nowhere, this conversation will hit hard—and open your eyes. Elle Anderson shares how she went from losing everything twice—including being down to her...

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301 - Why Most Airbnb Investors Fail Before They Even Launch with Kim Fitzpatrick show art 301 - Why Most Airbnb Investors Fail Before They Even Launch with Kim Fitzpatrick

Real Estate Investor Growth Network Podcast

301 - Why Most Airbnb Investors Fail Before They Even Launch with Kim Fitzpatrick What if the biggest mistake in short-term rentals isn’t the deal… it’s how you launch it? Too many investors lose time, money, and momentum before their listing even goes live. From blown budgets to slow setups and missed revenue windows, the launch phase can quietly kill your profits before you ever welcome your first guest. In this episode, short-term rental expert Kim Fitzpatrick reveals her proven 7-day property launch system that’s 8x faster than DIY. Starting with just $40 and a plane ticket, Kim...

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300 - The Mentor Who Changed Everything, Than Merrill show art 300 - The Mentor Who Changed Everything, Than Merrill

Real Estate Investor Growth Network Podcast

300 - The Mentor Who Changed Everything, Than Merrill   What if everything you’ve been doing to “learn” real estate is actually keeping you stuck? In this powerful 300th episode, Jen Josey sits down with legendary investor and mentor Than Merrill to expose the truth about why so many aspiring investors stay trapped in learning mode, and what it really takes to break through, take action, and build a profitable real estate business. With over $2 billion in real estate transactions and nearly two decades of experience, Than shares the exact mindset shifts, systems, and strategies that...

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299 - The Short-Term Rental Safety Mistakes That Could Destroy Your Business show art 299 - The Short-Term Rental Safety Mistakes That Could Destroy Your Business

Real Estate Investor Growth Network Podcast

299 - The Short-Term Rental Safety Mistakes That Could Destroy Your Business Your short-term rental could be one overlooked hazard away from a lawsuit, a tragedy, or the end of your investing career — and you probably don't even know it. In this eye-opening episode of REIGN, the Real Estate Investor Growth Network, host Jen Josey sits down with Justin Ford, Director of Safety and Certification Programs at Breezeway, to expose the hidden dangers that most STR hosts completely ignore. With nearly 30 years in the short-term rental industry, Justin reveals why over 80% of incidents have...

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298 - The Hidden Real Estate Strategy No One Talks About: Seller Finance Notes Explained show art 298 - The Hidden Real Estate Strategy No One Talks About: Seller Finance Notes Explained

Real Estate Investor Growth Network Podcast

298 - The Hidden Real Estate Strategy No One Talks About: Seller Finance Notes Explained What if the biggest opportunities in real estate aren’t in flipping houses… but in buying paper? In this eye-opening conversation, Will Harvey breaks down the hidden world of seller finance notes, hard money lending, and how savvy investors are capitalizing on valuation gaps between public and private markets. If you’ve ever felt stuck relying on traditional flips or unpredictable buyers, this episode reveals a smarter way to create consistent returns. Will shares the real strategies he uses through...

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297 - Why Smart Investors Are Quietly Buying Detroit Real Estate Right Now show art 297 - Why Smart Investors Are Quietly Buying Detroit Real Estate Right Now

Real Estate Investor Growth Network Podcast

Episode Summary What if one overlooked U.S. market could deliver cash flow, appreciation, and turnkey simplicity all at once? In this episode, Jen Josey sits down with Voytek Mardula and James Lloyd to uncover why Detroit real estate investing is rapidly becoming one of the most compelling opportunities for investors seeking passive income, portfolio growth, and scalable wealth. With over 600 renovated homes, $100M+ raised from private investors, and thousands of guest stays managed, Voytek and James share how they built a data-backed turnkey investing model that removes the guesswork. They...

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296 - Passive Commercial Real Estate Investing Explained by a Deal Expert show art 296 - Passive Commercial Real Estate Investing Explained by a Deal Expert

Real Estate Investor Growth Network Podcast

What if the biggest reason you have not stepped into commercial real estate is not lack of money, but lack of clarity? In this episode, Jen Josey sits down with Michael Holshouser of Linville Team Partners to break down how accredited investors can build wealth through commercial real estate without getting lost in confusing deals, vague promises, or risky guesswork. If you have ever wondered how passive real estate investing really works, this conversation pulls back the curtain.     Michael shares how his team created an investor portal that gives people deal-by-deal...

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295 - He Quit Traditional Rentals for Land Investing and It Changed Everything with Brent Bowers show art 295 - He Quit Traditional Rentals for Land Investing and It Changed Everything with Brent Bowers

Real Estate Investor Growth Network Podcast

What if the biggest real estate opportunity isn’t a flip, a rental, or an apartment complex, but a piece of vacant land most investors overlook? In this episode, Brent Bowers breaks down how land investing can create cash flow, seller-financed income, and affordable housing opportunities without the constant repairs, tenant drama, and surprises that come with traditional rentals. If you’ve ever wondered whether land is too risky, too boring, or too hard to value, this conversation will challenge everything you thought you knew.   Brent shares how he transitioned from military...

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294 - How Smart Real Estate Investors Use Virtual Assistants to Scale Faster with Bob Lachance show art 294 - How Smart Real Estate Investors Use Virtual Assistants to Scale Faster with Bob Lachance

Real Estate Investor Growth Network Podcast

Feeling overwhelmed in your real estate business? If your deals are slowing down, your inbox is overflowing, and you feel like the bottleneck in your own company… you’re not alone. In this episode, Jen Josey sits down with real estate entrepreneur and outsourcing expert Bob Lachance to reveal how smart investors eliminate bottlenecks, reclaim their time, and scale their businesses using virtual assistants and automation. Bob Lachance has completed 1,500+ real estate transactions and built multiple companies—including REVA Global, a virtual assistant service designed specifically for real...

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293 - Infinite Banking: Unlocking Financial Freedom with Anthony Faso & Cameron Christiansen show art 293 - Infinite Banking: Unlocking Financial Freedom with Anthony Faso & Cameron Christiansen

Real Estate Investor Growth Network Podcast

293 - Infinite Banking: Unlocking Financial Freedom with Anthony Faso & Cameron Christiansen What if the money you need for your next deal is already sitting right under your nose—and you’re just not using it the right way? In this episode, we break down how real estate investors can stop “begging” for funding, keep their money compounding, and use smarter systems to build real financial freedom. Jen Josey sits down with Anthony Faso and Cameron Christensen (founders of Infinite Wealth Consultants and hosts of the Infinite Wealth Podcast) to dumb down the concept of infinite...

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Mastering Short-Term Rental Investments: Insider Tips with Kenny Bedwell | REIGN Podcast
 
Welcome back to the Real Estate Investor Growth Network (REIGN) Podcast, hosted by Jen Josey! In this episode, we welcome short-term rental expert and data-driven investor Kenny Bedwell. Kenny reveals how he transitioned from a corporate career at Citibank to building a thriving real estate portfolio focused on short-term rentals and vacation properties.
 
Discover proven strategies for finding off-market deals, identifying the most profitable short-term rental markets, and maximizing your rental income. Kenny discusses the importance of niche investing, selecting the right amenities for Airbnb and VRBO properties, and using data analytics to boost your returns. You’ll also learn how to avoid the most common mistakes made by new short-term rental investors, the difference between forced appreciation and cash flow, and why reviews are critical for STR success.
 
Whether you’re a new real estate investor or looking to scale your short-term rental business, this episode is packed with actionable tips on property management, market research, and leveraging consulting resources like STR Insights. Don’t miss Kenny’s personal advice for achieving your real estate goals!
  • 00:00 – Real Estate Investor Growth Network (REIGN) Podcast introduction, short-term rental investing overview
  • 01:02 – How to find off-market real estate deals, lead generation strategies
  • 03:15 – Guest intro: Kenny Bedwell, short-term rental specialist, Airbnb investing
  • 04:38 – Kenny’s real estate investing journey, transitioning from corporate to entrepreneurship
  • 08:01 – Maximizing short-term rental income, property performance optimization
  • 09:50 – How to identify profitable short-term rental markets, market research tips
  • 26:52 – Essential amenities for Airbnb, VRBO, and vacation rental properties
  • 31:20 – Pros and cons of boutique hotels vs. short-term rentals
  • 34:53 – Forced appreciation strategies vs. short-term rental cash flow
  • 35:56 – Common rookie mistakes in short-term rental investing, risk management
  • 41:43 – The importance of guest reviews and reputation management in STRs
  • 48:56 – STR Insights, consulting services for short-term rental investors
  • 54:56 – Kenny’s personal goals, success advice for real estate entrepreneurs

 

KENNY BEDWELL is a seasoned real estate investor and entrepreneur known for helping high-income
professionals identify and acquire short-term rental properties that generate strong cash flow. With over
eight years of experience in market analysis and deal structuring, he has guided more than 300 clients toward
investments that consistently deliver impressive returns.
Kenny’s heavy data-driven experience and knowledge stem from his time at CitiBank, where he worked for
several years as a data analyst in the Equities Market. This foundation has shaped his analytical approach to real
estate, enabling him to uncover high-performing opportunities others often miss.
Beyond investing, Kenny is the host of Cash Flow Positive, a top-ranked podcast that reached #30 in iTunes’
Entrepreneur category and #85 among all U.S. business podcasts. Through his podcast, coaching, and speaking
engagements, he shares proven strategies for spotting opportunities, leveraging data, and optimizing property
performance.
Kenny’s straightforward, results-driven approach empowers investors to act with confidence—whether closing
their first deal or scaling a portfolio. His mission is clear: to help others achieve financial freedom through real
estate while avoiding the costly mistakes he’s seen many investors make.

 

To learn more about Jen Josey, visit https://www.therealjenjosey.com/

To join REIGN, visit https://www.reignmastermind.com/

Stuff Jen Josey Loves: https://www.reignmastermind.com/resources

Buy Jen Josey’s Book: From Beginner to Badass: https://a.co/d/bstKlby

Interested in growing your rental portfolio with Jen as your coach? Check out Rental Property Pro: https://rentalproppro.com/booking?am_id=reign