Welp... Start by saying I'm not at my goal yet. I'm about 2-years away from passively cashflowing all my living expenses + a nice savings rate.

With that said, I graduated school during the great recession and hiring was rather bleak. I went to a school that's usually well https://twitter.com/MTSpeigle/status/1309355982904934400

regarded, and was a cum laude finance major. School wanted me to go i-banking or consulting and I interviewed with Deloitte and McKinsey who basically both told me it seemed like I'd be passionate about CRE.

My mom never sold the first condo she ever bought downtown Chicago so I

got to witness a nice passive rental investment, which had great appeal.

Coming out of school at that time, real estate was in the tank and no one was hiring analysts fresh out of school b/c there were so many available all the entry level roles required 2+ year experience. I

ended up going into brokerage and learning how to sell (most important skill, imo). My current business partner and I built out a tenant rep advisory group that works nationally and built up a strong market share in location based medical tenants advising on site selection by

building custom predictive models (minor in stats) and executing at a high level. I was always interested in the investment side, but built up a lot of expertise and investible cash through pure brokerage production.

Couple fortunate things allowed that:
1) graduating debt free

2) gf, now wife had a great salary

As a team she allowed me to pile the risk on and made a huge jockey bet that I wouldn't fail in a high attrition business. While there is structure to brokerage, in a lot of instances you're taking on entrepreneurial risk and really grinding a

lot of cold calls / business development out.

It has worked for me and certainly been a fun ride.