Teaming Up vs. Going Solo for First Fix & Flip in Chicagoland?

Question

Hello Fix & Flip community,

My friends and I are interested in getting into fix and flips in the Chicagoland area. We're considering pooling our capital to take on a project together, but I'm also wondering if it might be smarter for me to partner with an experienced investor first. That way, I can learn the ropes and then guide my friends through the process later.

What do you think makes more sense for a first-time investor — team up with friends from the start, or gain experience solo with a mentor or investor before bringing others in?

Would appreciate any advice or personal experiences!

Sultan Ali · Answer

From what I’ve seen (and experienced), partnering with someone seasoned on your first flip can save a lot of trial-and-error. You get to see how they structure the deal, manage the rehab, and handle surprises - all without carrying the entire risk yourself.

I work in the investment space and have watched people try both approaches. The ones who start with an experienced partner usually end up moving faster and making fewer costly mistakes. Once you’ve been through that first cycle, you’ll be in a much stronger position to bring your friends in confidently.

Either way, having clear agreements and defined roles from the start is huge for keeping everyone on the same page.

Jason Taken · Answer

Chicago is tough on a beginner. Stick to the suburbs. And if you're looking for a really beginner friendly area, head over to northwest Indiana. A lot of us invest over there as its pretty close to Chicago with less cost, headache, and struggle with local municipalities.

Aaron Zimmerman · Answer

I would recommend learning from an experienced investor as they will be more likely to know the rules. The city of Chicago is a machine and you need to know how to play the game. Suburbs are generally a bit easier but there are certain ones that require rental licenses or have strict laws when buying/selling properties (I.e. making property owners upgrade the property to meet certain code)

Diego Montoya · Answer

From the perspective of a lender, experience from the borrower is always more attractive. Even though there's plenty of lenders willing to work with 0 experience investors like us right now we can do 0 experience 90 100 financing on fix n flips, but working with an experienced GC or having a mentor for your project will help you in regards to learning the ropes as well as building that track record and setting you up for future projects.

Best,

Jennie Berger · Answer

My advice? Don't risk your friendships on your first flip.

As a lender who’s been a borrower, I can tell you money can ruin relationships, especially when a project goes south.

You need to learn the ropes, the hard way, with an experienced partner first. From my side of the table, I'd rather lend to a team with one seasoned lead than a group of first-timers.

Get the experience solo, then you can guide your friends. It's a win-win for everyone involved!

-Jennie

Teaming Up vs. Going Solo for First Fix & Flip in Chicagoland?

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