RE on the side as a DCM guy?

Folks, I'm working a good old boring DCM gig (working both corporate and CRE debt deals) at a no name middle market bank. Pay is ok (in line with lower middle market bank pay). Hours aren't bad ~50 hrs per week. Work is boring and there are limited exits. I'm not being mentally challenged at work at all, so I've had a lot of time to think and reflect. Recently, I've been thinking about investing in RE part-time. I think it's a great opportunity and a great way for me to use my brainpower to better myself & improve my knowledge. I live in a ok cost of living area and the money I make goes a long way where I live. I'm currently a senior associate on the way to VP. I think at the VP level, I will have a lot of discretionary income since I'm single and don't have a GF. With that being said, here are my thoughts:

(1)My bank offers tuition reimbursement for graduate programs. I'm thinking about getting a MSRE degree and having my bank pay for ~50% of it. It'll cost about $25-30K out of pocket for me over two years (part-time), but I'll end up with a masters degree from a good school (Think: NYU Shack, Georgetown, etc...), education on CRE and a good network. I'm thinking I can build connections in the program (partner with them) and perhaps do some development work on the side (buy/build/renovate & hold) after graduation (thinking residential apartments, large duplexes). I think this plays well with the CRE experience that I have now, but is most costly. On a side note, I'll probably be ~30 by the time I exit the program, so I'll actually be taken seriously.

(2)Work on buying properties in my area and try to build a network online. This is the less costly and easier/faster option, but I won't have a good network or a lot of knowledge on RE. 

I'm leaning towards #1, but I wanted to get a sanity check on this forum. Does this make sense to you guys? Is this doable? I think this would be an endeavor worth pursuing since I think it would be mentally challenging and put me on my path to passive income

1 Comments
 

Est ipsa quia in quia inventore est. Libero sint deleniti in officiis et et ex.

Atque odit molestias molestiae laboriosam vitae dolorem. Quidem aut corporis qui velit autem qui. Adipisci odio quo autem eius in molestias. Iste quod dolorem ea quos.

Dolor hic iure totam dolores. Esse non debitis est incidunt voluptate. Optio consectetur ea voluptatem deserunt quas. Quia error laborum debitis ut dignissimos nobis. Pariatur architecto enim tempora vel ut ducimus. Numquam expedita quo qui aut accusamus temporibus.

I'm an AI bot trained on the most helpful WSO content across 17+ years.

Career Advancement Opportunities

July 2026 Investment Banking

  • Evercore 01 99.4%
  • Moelis & Company 01 98.9%
  • JPMorgan 01 98.3%
  • Guggenheim Partners 01 97.7%
  • Morgan Stanley 07 97.1%

Overall Employee Satisfaction

July 2026 Investment Banking

  • Moelis & Company No 99.4%
  • Evercore No 98.8%
  • Morgan Stanley 01 98.3%
  • BMO Capital Markets 13 97.7%
  • Banco Santander 01 97.1%

Professional Growth Opportunities

July 2026 Investment Banking

  • Evercore 01 99.4%
  • Moelis & Company 01 98.9%
  • Morgan Stanley 06 98.3%
  • Goldman Sachs 01 97.7%
  • JPMorgan 01 97.1%

Total Avg Compensation

July 2026 Investment Banking

  • Vice President (15) $434
  • Associates (46) $258
  • 3rd+ Year Analyst (8) $210
  • 2nd Year Analyst (22) $179
  • Intern/Summer Associate (13) $156
  • 1st Year Analyst (80) $150
  • Intern/Summer Analyst (73) $101
notes
16 IB Interviews Notes

“... there’s no excuse to not take advantage of the resources out there available to you. Best value for your $ are the...”

Leaderboard

success
From 10 rejections to 1 dream investment banking internship

“... I believe it was the single biggest reason why I ended up with an offer...”