Career advice- path into management/investment

Chicago, Illinois
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Career advice- path into management/investment

David Hanson
Member since 2026 · 2 posts · 7 votes

Hello everyone,

I’m 22, based in the Chicago area, and just finished a degree in finance and real estate in May. My long-term goal is to own small multifamily or mixed-use properties in Chicago. I have a strong interest in getting a start in the industry with hands-on experience in BRRR deals, multi-family management, brokerage, or any other field where I can learn how investors operate. 

I could really use advice on finding an early-career path or mentorship. I’ve applied to leasing and assistant property manager roles, but many require prior experience. I'm open to commission-only brokerage roles, but I'm not sure if this is a good place to start. My past work experience started at a restaurant, bar jobs at college, an inventory management internship, and most recently, I helped launch and manage a family-owned franchise business after graduation.  

I'd love to hear stories of how you guys got hands-on exposure as recent grads or young professionals. How did you find a mentor in the industry? If you could go back, how would you get started? What are good resources specifically in Chicago? 

Thanks in advance!

-David

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Aaron ZimmermanBusiness Member
Accountant · Chicago, IL · Member since 2018 · 2k+ posts · 1k+ votes
9mo

David - welcome! Love the game plan and wanting to be involved in real estate in multiple ways. 

I'd say if you're wanting to get into management, I'd try to increase your odds of success and go to networking events where property management companies hang out. In my experience, it seems Like property management companies are hiring pretty frequently. You may have to work your way up but there's definitely a path to assistant property manager if you can't get it right away. 

On the investing side, I'd also go to networking events such as Chicago multifamily club, Windy City REI, Chicago breakfast club, etc. I'd recommend listening to the straight up Chicago investor podcast as well. There's all local guests, with some of them being property management companies that you could reach out to and try to provide value.

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  • Aaron ZimmermanBusiness Member
    Accountant · Chicago, IL · Member since 2018 · 2k+ posts · 1k+ votes
    9mo

    David - welcome! Love the game plan and wanting to be involved in real estate in multiple ways. 

    I'd say if you're wanting to get into management, I'd try to increase your odds of success and go to networking events where property management companies hang out. In my experience, it seems Like property management companies are hiring pretty frequently. You may have to work your way up but there's definitely a path to assistant property manager if you can't get it right away. 

    On the investing side, I'd also go to networking events such as Chicago multifamily club, Windy City REI, Chicago breakfast club, etc. I'd recommend listening to the straight up Chicago investor podcast as well. There's all local guests, with some of them being property management companies that you could reach out to and try to provide value.

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    • David Hanson
      OP
      Member since 2026 · 2 posts · 7 votes
      9mo
      Quote from @Aaron Zimmerman:

      David - welcome! Love the game plan and wanting to be involved in real estate in multiple ways. 

      I'd say if you're wanting to get into management, I'd try to increase your odds of success and go to networking events where property management companies hang out. In my experience, it seems Like property management companies are hiring pretty frequently. You may have to work your way up but there's definitely a path to assistant property manager if you can't get it right away. 

      On the investing side, I'd also go to networking events such as Chicago multifamily club, Windy City REI, Chicago breakfast club, etc. I'd recommend listening to the straight up Chicago investor podcast as well. There's all local guests, with some of them being property management companies that you could reach out to and try to provide value.


       Thanks Aaron! I appreciate the warm welcome. I think networking events would help my search a lot, I'm becoming more familiar with those events since joining the forum a few days ago. I will definitely continue listening to straight up Chicago investor as well, its a great show. 

      Are you an investor in Chicago?

      1Reply
    • Aaron ZimmermanBusiness Member
      Accountant · Chicago, IL · Member since 2018 · 2k+ posts · 1k+ votes
      9mo

      @David Hanson happy to help! yes I invest in Chicago (and live here too)

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  • Mike FisherBusiness Member
    New Lenox, IL · Member since 2024 · 128 posts · 66 votes
    9mo

    David, yes, I invest in and around Chicago.

    I started by getting close to operators and property managers and showing up consistently at local meetups. That is still the fastest path for a newer person because you learn what deals really look like, how tenants and vendors behave, and what investors actually care about.

    If I were you at 22, I would do three things over the next 60 days.

    Pick a lane for your first job

    Assistant PM or leasing is a strong start if your goal is ownership, because it teaches you rent readiness, turns, tenant issues, collections, capex, and what breaks. Brokerage can work too, but only if you are disciplined and can handle a commission ramp.

    1. Make yourself useful to investors

      Go to those meetups and offer something specific: build a rent comp sheet, pull a tax bill history, call a few contractors for rough rehab ranges, or walk a property and do a photo based punch list. Investors remember execution.

    2. Find one operator and one PM mentor

      One investor mentor teaches acquisition and underwriting. One PM mentor teaches reality. That combination is gold.

    And yes, keep coming to the events you listed. Chicago is a relationship market.

    If you want, tell me what neighborhood and asset type you want to buy first, 2 to 4 unit, mixed use, or 10 plus units, and I will tell you the best first role to target and the exact skills to build so you are useful immediately.

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  • Denise SuppleeBusiness Member
    Realtor · Willow Grove, PA · Member since 2017 · 1k+ posts · 656 votes
    9mo

    Hands-on experience often comes fastest by getting close to active operators, even if the role isn’t perfect at first. Property management, acquisitions analyst roles, or working for a small multifamily owner can teach you more about how deals actually work than commission-only brokerage alone. Mentorship usually comes from showing up consistently, being useful, and learning the business from the ground up,  especially in a market as deep as Chicago’s.

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  • Jonathan KlemmBusiness Member
    Moderator
    Contractor · Chicago, IL · Member since 2016 · 4k+ posts · 2k+ votes
    9mo

    What's going on @David Hanson - If you have a degree in finance and real estate...and it sounds like you are a go-getter, then I highly suggest looking into some Chicago commercial real estate brokerages.

    Other options would be some larger property managers or developers.  I've got a couple of good connections that would be worth linking up with.

    Most importantly, I recommend checking out some of the local meetups to network with other Chicago investors and industry professionals. 

    https://www.biggerpockets.com/forums/521-real-estate-events-...

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  • Paul De Luca
    Real Estate Agent · Chicago, IL · Member since 2018 · 1k+ posts · 1k+ votes
    9mo

    @David Hanson

    If your goal is to buy 2-4 unit properties, it would be more beneficial for you to get a W2 job since that makes it easier to qualify for financing rather than being commission only/1099. 

    I think you have the right idea with applying to leasing and property management jobs. Working in property management will give the most relevant skillset and experience for owning and managing rental properties. Consider working for a property manager & brokerage and work as a property manager and get your real estate license to sell on the side. You'll be working with managers, contractors, owners, brokers etc so I think it would give you the most comprehensive exposure.

    0Reply
  • Henry Lazerow
    Real Estate Agent · Chicago, IL · Member since 2017 · 2k+ posts · 2k+ votes
    9mo

    Feel free to shoot me a PM happy to chat on a call. I did my first house hack 4 unit at 26 in Roger’s Park and have helped many younger people get in the market. House hack is the best way to start as can buy low down. I worked as an intern and then analyst for a bit at a real estate investment firm but really you just need solid income to get approved for a house hack and real estate investing is not that complicated, no mentor needed and be careful anyone who offers to mentor you as most are scammy. See if any jr analyst positions open if you have a finance degree. Will make great money after few years and life long contacts. Being a realtor or leasing won’t get you approved for good mortgages for at least 2+ years. W2 income is the best.

    0Reply
  • Wale LawalBusiness Member
    Real Estate Broker · Houston | Dallas | Austin, TX · Member since 2018 · 5k+ posts · 2k+ votes
    9mo

    @David Hanson

    Your finance and real estate background along with your business experience already put you ahead of the majority of beginners. A wise move in Chicago could be doing networking with a local brokerage, property management company or investor group that are all focused on multifamily even if you start at an entry level position, since that will be the place where you will quickly gain real deal and operation exposure. For getting guidance through a mentor, visit the Chicago real estate investor meetups, become a part of the NAIOP or local REIA events and begin with the relationship building most mentors will be found by those who are trustworthy and come regularly.

    Good luck!

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  • Clare PitcherBusiness Member
    Property Manager · Milwaukee, WI · Member since 2024 · 162 posts · 97 votes
    9mo

    Hey David!

    I graduated in May 2024 with a business degree and knew I wanted to work in real estate and possibly invest one day. I started applying to development companies, brokerages, and property management companies, but it was difficult to hear back when I was only submitting online applications, especially with limited experience.

    What really helped me was calling the office to set an appointment to speak with the hiring manager, or, if I didn’t hear back, showing up in person with a resume and cover letter when I was home for breaks. This went a long way with hiring managers and clearly demonstrated initiative and determination. I highly recommend this strategy, as it truly sets you apart from your peers.

    I’ve loved working in property management because I get to learn from other owners’ mistakes, so I don’t have to make them with my own future properties.

    A great company I’ve connected with in Chicago is GC Development and Realty. They are one of the largest property managers in the city and offer many different career paths. I suggest visiting their office and inquiring about any open positions they may have. If you’re hungry to learn and coachable, I can almost guarantee any company would be happy to have you.

    Best of luck, and please feel free to reach out if you have any questions!

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  • Mike FisherBusiness Member
    New Lenox, IL · Member since 2024 · 128 posts · 66 votes
    9mo

    David, you are on the right track. If your goal is to own small multifamily in Chicago, the fastest path is a W2 role inside the business so you learn operations and you can qualify for financing.

    Target assistant PM, leasing, maintenance coordinator, or analyst roles at a property management company or active investor. Then show up consistently at Chicago meetups and make yourself useful to operators, bring rent comps, tax history, contractor rough numbers, or a photo based punch list from a walk through. That is how you earn mentors.

    Chicago resources: Windy City REI, Chicago Multifamily Club, Chicago Breakfast Club, NAIOP, and the Straight Up Chicago Investor podcast network.

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