John Preston of Horvath & Tremblay joins us to discuss opportunities in multifamily and mixed-use assets on Chicago's North Side!

John begins by discussing what it takes to build a successful brokerage business including early struggles before hitting his stride! He breaks down his process for reaching out to and converting seller leads and also explains the work brokers do that leads to a successful transaction. In typical SUCI fashion, John gets hyper-specific on neighborhoods that have seen great rent growth and areas where he sees investors putting their money! He closes with a bullish outlook on Chicago and emphasizes the importance of building market knowledge and networking to be successful in the game!

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Guest: John Preston, Horvath & Tremblay | Email John: jpreston@hgapartments.com | Connect with John on LinkedIn

Link: NBOA Chicago

Guest Questions:

02:45 Housing Provider Tip - Understand catch basins and have a maintenance plan.

04:35 Intro to our guest, John Preston!

06:47 Getting off the ground as a real estate broker focusing on multi-family assets.

16:17 Troubling deals early on in John's career.

22:18 The work behind a successful listing.

29:30 Effectively following up with and converting leads!

31:27 How buyers can find opportunities in today's market.

34:57 John breaks down north side neighborhoods!

45:00 John's pick for a neighborhood with major upside!

50:17 John's bullish outlook on Chicago.

51:15 What is your competitive advantage?

52:15 One piece of advice for new investors.

53:04 What do you do for fun?

53:34 Good book, podcast, or self development activity that you would recommend?

54:23 Local Network Recommendation?

55:11 How can the listeners learn more about you and provide value to you?

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Production House: Flint Stone Media

Copyright of Straight Up Chicago Investor 2026.

Episode 459: North Side Neighborhoods and Market Opportunities with John Preston

Straight Up Chicago Investor

Episode 459: North Side Neighborhoods and Market Opportunities with John Preston