How Buying a Failing Business Turned Into a Short-Term Rental Empire

Welcome back to Radical Wealth Plan, hosted by Paul Mark Morris and brought to you by Entrepreneur Media. Today, we're talking about an exciting and potentially lucrative area of real estate—short-term rentals. I had the pleasure of sitting down with Josh Rudin and Patryck Swietek, two impressive young investors who have built a thriving business in the short-term rental space. They didn’t just dip their toes in—they went all in, from buying and managing properties to scaling up by acquiring an entire property management company. Josh started flipping houses at just 19 years old, learning the ropes of real estate investment firsthand. Patryck, on the other hand, comes from a high-tech entrepreneurial background and brought his business expertise into the world of short-term rentals. Together, they’ve built a rapidly growing business, managing dozens of properties and helping others succeed in this space. In this episode, we cover what it really takes to be successful in short-term rentals, from choosing the right market and property type to standing out in an increasingly competitive field. They share the hard lessons they learned from buying a business, the strategies they use to maximize profitability, and why regulations are actually a good thing when choosing where to invest. Whether you’re looking to get started with your first rental or scale an existing portfolio, there’s a lot to take away from this conversation. If you’ve ever considered short-term rentals as a path to wealth, or if you just want to hear a great story about two entrepreneurs taking big risks and making them pay off, you won’t want to miss this one. Timestamps 00:00:00 Introduction 00:01:18 Josh & Patryck 00:02:02 Patryck’s Journey – From Deli Worker to Real Estate Investor 00:05:15 Early Investments and Learning from a Mentor 00:08:02 Leveraging Credit and Buying During Market Lows 00:10:33 Josh’s Background – From Flipping Houses to Short-Term Rentals 00:11:36 Patryck’s Tech Background and Entrepreneurial Journey 00:16:20 Short-Term Rental Market & Airbnb Arbitrage 00:20:35 Forming a Partnership 00:23:22 Acquiring a Property Management Company 00:26:00 Lessons Learned from the Acquisition 00:30:38 Transitioning from Operators to Business Owners 00:35:34 Strategies for Short-Term Rental Success 00:41:09 Understanding Local Regulations and Investment Safety 00:46:40 Properties That Perform Well 00:50:49 Future Plans & Final Takeaways for Aspiring Investors Learn more about your ad choices. Visit megaphone.fm/adchoices