The Side Hustle and Business Show with Eric Lindsey

Using Uber As A Side Hustle To Buy Short-Term Rentals For Airbnb with Jonathan Dempsey


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Jonathan is a Philadelphia-based real estate investor, agent, and business owner specializing in short-term rentals. This 28-year-old millionaire reached financial freedom before age 30 by building a portfolio of over 70 short-term rental units. He spends most of his free time traveling and has also created a short-term rental property management business that manages a portfolio of over 200 units across multiple cities. He believes that financial independence is a lifestyle and that anyone with a desire to be financially independent should pursue it. This is what inspired him to create the “Live Free” to teach entrepreneurs how to pursue their financial freedom.



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During this episode, you will learn about:
[01:03] A bit about Jonathan and how he got started in real estate


[02:43] Tips and strategies that Jonathan has found to work better in the Airbnb model  


[09:32] Airbnb model expenses and how to self-manage your revenue and expenses  


[04:52] Techniques that will get you better ratings and more reviews for your short-term rentals


[06:37] How the day-to-day looks like when buying real estate and working a W2 job 


[09:04] Jonathan's strategy of finding and locating short-term rental deals   


[11:36] The average expense ratio of short-term rentals


[12:59] Jonathan's hold technique and the endgame for his exit strategy 


[14:59] Jonathan’s unique strategy of financing and operating deals


[16:46] Other businesses Jonathan is working on outside his short-rental properties 


[18:46] What Jonathan wishes he would have known before he started investing in real estate


[19:46] How long it took Jonathan to close his first real estate transaction


[21:29] How Jonathan balances business and personal life to ensure both continue to thrive


[22:58] How to start a successful real estate business with a limited amount of money and time


[24:37] What would Jonathan do to build a business like his if he was down to $100, with no experience and with limited time


[25:48] A great personal development book that Jonathan recommends for Moonlight listeners 


[26:52] How can you reach out and connect with Jonathan



Notable Quotes:

  • When you are starting, you want to self-manage; handling one property while working another job is not that difficult.
  • It’s essential to work with a mentor earlier on; If you work with someone who is already doing it, you are likely to get good referrals for contractors and other things.
  • Anything is possible if you approach it with the right strategy.


...more
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The Side Hustle and Business Show with Eric LindseyBy Eric Lindsey

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