280 - Creating Profitable Short Term Rentals with Kenny Bedwell

Dec 1, 2025

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