Episode 389: Different Approach To Short Term Investing In Chicago With Sebastian Mysliwiec

Jul 24, 2025

Ask episode

Chapters

Transcript

Episode notes

Properties for Sale on the North Side? We want to buy them. Email: StraightUpChicagoInvestor@gmail.com

Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: GCRealtyInc.com/tenant-placement

Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: GCRealtyinc.com

=============

Sebastian Mysliwiec, founder of The Dream Rentals, explains how he’s built a short-term and mid-term rental management company that delivers top guest experiences and maximizes profits!

Sebastian talks about cutting his teeth and eventually thriving at a marketing company that helped build his real estate skill set. He provides tactical advice on underwriting, marketing, and managing short-term rentals (STRs). Sebastian explains how his team manages seasonality, shares a STR horror story, and top amenities for guests. He closes with remarks on refinancing considerations for STR properties and his team’s growth strategy.

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

=============

Connect with Mark and Tom: StraightUpChicagoInvestor.com

Email the Show: StraightUpChicagoInvestor@gmail.com

Guests: Sebastian Mysliwiec, The Dream Rentals

Link: The Dream Rentals Instagram

Link: Skyscraper Tom's Instagram

Link: The 12 Week Year (Book Recommendation)

Guest Questions

01:58 Housing Provider Tip - Leverage Freedom of Information Act (FOIA) to request property info during due diligence!

04:25 Intro to our guest, Sebastian Mysliwiec!

08:31 Defining AirBnB arbitrage.