# 291 - From Cubicles to Closings: Mike Doherty's Path to Real Estate Success

Page: https://stenobird.com/podcast/real-estate-investor-growth-network-podcast-1375818/291-from-cubicles-to-closings-mike-doherty-s-path-to-real-estate-success
Text version: https://stenobird.com/podcast/real-estate-investor-growth-network-podcast-1375818/291-from-cubicles-to-closings-mike-doherty-s-path-to-real-estate-success.md
Podcast: [Real Estate Investor Growth Network Podcast](https://stenobird.com/podcast/real-estate-investor-growth-network-podcast-1375818)
Published: 2026-02-16T11:00:00+00:00
Episode link: https://reign.libsyn.com/291-from-cubicles-to-closings-mike-dohertys-path-to-real-estate-success
Audio file: https://dts.podtrac.com/redirect.mp3/traffic.libsyn.com/secure/reign/Mike_Doherty.mp3?dest-id=2264141
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JSON: https://stenobird.com/v1/public/podcasts/real-estate-investor-growth-network-podcast-1375818/episodes/291-from-cubicles-to-closings-mike-doherty-s-path-to-real-estate-success
Duration seconds: 2527

## Resource

291 - From Cubicles to Closings: Mike Doherty's Path to Real Estate Success Jen Josey hosts the REIGN podcast and shares a "Badassery Bestowment" on why every listing needs a professional photographer, citing five reasons: more clicks and offers, selling a lifestyle, protecting price, standing out in a crowded market, and saving time and stress. She then interviews Mike Doherty, a Connecticut-based full-time real estate investor, realtor, entrepreneur, co-founder of Skytree Investments, and host of the Sky's the Limit Podcast. Mike describes his path from a finance job after graduating from the University of Connecticut in 2015 to real estate investing, including learning through BiggerPockets, house hacking a duplex, and scaling by using the BRRRR method after running out of capital. He discusses misconceptions new investors face, emphasizes taking action, using meetups to build confidence and connections, and explains creative financing strategies such as seller financing and subject-to deals, including an example with 10% down, 4% interest, 40-year amortization, and a 10-year balloon. Mike shares a favorite deal involving raising the full down payment, selling after one year, and completing a 1031 exchange into a seller-financed five-unit property. He explains OPM approaches, partnerships and joint ventures, friends-and-family capital, and the importance of track record and some skin in the game. Mike outlines his move from W2 work to becoming a full-time realtor by lowering living expenses through house hacking, and he shares his BADASS answers: key books (Rich Dad Poor Dad, Who Not How, Never Split the Difference), best advice (take action), his drive (generational wealth and financial freedom), a goal of reaching 200 doors before age 35 (currently at 100), system…

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