Riding the Short-Term Lane: Kenny Bedwell’s Data-Driven Journey to STR Riches episode artwork

EPISODE · Feb 10, 2026 · 39 MIN

Riding the Short-Term Lane: Kenny Bedwell’s Data-Driven Journey to STR Riches

from Real Estate Underground · host Ed Mathews

Mastering Short-Term Rentals with Data-Driven Real Estate Strategies - Featuring Kenny Bedwell from STR InsightsIn this insightful episode of the Real Estate Underground podcast, host Ed Mathews welcomes Kenny Bedwell from STR Insights to discuss the intricacies of short-term rental investments. Kenny shares his journey from a data analyst at Citibank to a successful real estate investor specializing in short-term rentals. He emphasizes the importance of choosing the right markets, investing in amenities, and focusing on the guest experience to succeed in the competitive short-term rental space. Kenny also highlights his strategies for managing properties remotely, leveraging local resources, and the value of balancing work and family life. This episode is a must-listen for anyone looking to optimize their investments in the short-term rental market.00:00 Introduction and Podcast Overview01:19 Guest Introduction: Kenny Bedwell from STR Insights01:45 Kenny's Background and Real Estate Journey02:19 The Shift to Short-Term Rentals02:45 Navigating Regulations and Diversifying Investments04:00 Understanding the Short-Term Rental Market09:17 Creating Unique Guest Experiences15:50 Managing Short-Term Rentals Across Multiple States20:07 Managing Property Operations20:57 Human Capital and Property Management23:35 Personal Drive and Motivation25:09 Valuable Advice and Lessons Learned32:41 Defining Success and Personal Growth34:46 Hobbies and Family Life37:25 Connecting with Kenny BedwellThis Week's Book: The Pumpkin Plan: A Simple Strategy to Grow a Remarkable Business in Any Field (Entrepreneurship Simplified) - By Mike MichalowiczElevista - Speed as a Service™Elevista Connect is the first AI-powered lead conversion system built for real estate investors. 🎧 Subscribe to Real Estate Underground for weekly insights on building wealth through real estate, without sacrificing your sanity.Additional Resources:Clark St Capital -> Passive real estate investments for busy business owners and executivesElevista -> AI SaaS for real estate investorsClark St Academy on YouTube -> Learn how to invest in real estateSocial Media:LinkedIn -> Ed Mathews (President at Clark St and Elevista)Heads up: If you find this week's book intriguing and you buy using our link, we receive a small commission that helps support the show. Thank you!

Episode metadata supplied by the publisher feed · Published Feb 10, 2026

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Mastering Short-Term Rentals with Data-Driven Real Estate Strategies - Featuring Kenny Bedwell from STR Insights In this insightful episode of the Real Estate Underground podcast, host Ed Mathews welcomes Kenny Bedwell from STR Insights to discuss the intricacies of short-term rental investments. Kenny shares his journey from a data analyst at Citibank to a successful real estate investor specializing in short-term rentals. He emphasizes the importance of choosing the right markets, in...

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Riding the Short-Term Lane: Kenny Bedwell’s Data-Driven Journey to STR Riches

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