Passive Real Estate Investment | Casmon Capital Group | United States

From Flipping to Multifamily with Tom Shallcross

Tom Shallcross is a born and raised Chicagoan specializing on the North and Northwest side of Chicago. Tom is director of Acquisitions and Operations at Drexel Properties, which owns and operates over 500 units on Chicago’s Northside, a licensed realtor with Second City Real Estate, and an avid investor/flipper himself. Tom is also the co-host of the Straight Up Chicago Investor Podcast and an active father of four.


We talked to Tom about his flipping strategies, and how he uses them to grow his multifamily portfolio, the importance of relationships, and his podcast “Straight Up Chicago Investor”.




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[00:01 – 03:33] Opening Segment

  • Tom talks about his background.

  • How he got into house hacking accidentally;

  • And how he moved forward to private lending

[03:33 – 11:12] Flipping to Grow

  • He talks about why he chose the private lending space.

  • Some of the six-figure flipping projects they worked on.

  • He breaks down their flipping strategy.

  • How Tom is using flipping to grow his multifamily portfolio.

  • Some of the unique strategies Tom uses to find leads.

  • The importance of relationships.

  • How he chose his partner.

[11:12 – 28:13] Building Relationships and Credibility

  • What to look for when acquiring.

  • The importance of having credibility.

  • Some of the lessons learned from buying a larger property.

  • Tom talks about the value he found in his podcast.

  • Some of the ways that Tom helps investors.

  • How one deal can snowball into many.

[28:13 – 33:38] Round of Insights

Apparent Failure:

Doing cold calls when he was in college.

Digital Resource:


Most Recommended Book:

Think and Grow Rich

Daily Habit:

Getting up early.

#1 Insight for Investing

You’ve got to understand what you are looking for.

Best Place to Grab a Bite in Chicago:

The Gale Street Inn

Contact Tom:

Click here to get to check out his podcast “Straight Up Chicago Investor”.

Tweetable Quotes:

“If you want to vouch for it with your mouth, you need to really be able to see it with your eyes.” – Tom Shallcross

Thank you for joining us for another great episode! If you’re enjoying the show, please LEAVE A RATING OR REVIEW, and be sure to hit that subscribe button so you do not miss an episode.

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