Skip to main content

Episode 157: Investing in Chicago Midterm Rentals with Rishi Bajaj

After staying in an Airbnb while on vacation, Rishi Bajaj realized how we can leverage this  strategy and used midterm rentals to multiply his rental income!

Rishi shares how he got the idea to venture out into the niche space of midterm rentals. He talks about furnishing, costs, and additional considerations when comparing midterm rentals to traditional long term rentals. He dives into why he sees value and has been investing in some south side neighborhoods and also shares the characteristics he looks for in properties! Throughout the show, Rishi provides valuable tips on thinking outside the box to maximize profit and ROI!

If you enjoy today’s episode, please leave us a review and share with someone who may also find value in this content!

04:45 House Provider Tip: Hire professional and reputable HVAC contractors to ensure systems function properly!

05:13 Intro to our guest, Rishi Bajaj!

08:15 What motivated Rishi to get into real estate?

12:07 How did Rishi live frugally when he first got started?

13:53 What are some considerations when furnishing a unit?

17:30 What are some additional costs to consider on midterm rentals that differ from long term rentals?

24:18 How is Rishi marketing his midterm rentals?

28:16 Why did Rishi start purchasing property in Bridgeport and the Heart of Chicago neighborhood?

31:15 What property characteristics does Rishi look for?

34:28 How are these properties being financed?

39:19 How does Rishi underwrite for vacancy?

43:57 How has Rishi managed a growing Chicago portfolio from a remote location?

49:34 What is Rishi’s competitive advantage? 

50:34 One piece of advice for new investors.

51:42 What do you do for fun?

52:19 Good book, podcast, or self development activity that you would recommend? 

53:32 Local Network Recommendation?

55:10 How can the listeners learn more about you and provide value to you?

That’s our show! Thanks for listening!


Guest Name: Rishi Bajaj

Guest Company: West Loop Capital Partners

Guest Link

Other Links for show notes:

Multifamily Insights (Podcast Recommendation)

The Short Term Show (Podcast Recommendation)

Eric Hubbard (Network Recommendation)