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

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), systems (assistant/transaction coordinator, Follow Up Boss CRM, calendar, and morning routine), and his definition of success as enough passive income to support his lifestyle. 

 

00:00 Welcome to REIGN: What to Expect on the Podcast

01:02 Badassery Tip: Why Pro Photos Sell Listings (5 Reasons)

03:24 Meet Mike Doherty: Investor, Realtor & Podcast Host

04:46 From Finance Cubicle to First House Hack Duplex

08:49 Early Landlord Lessons & Misconceptions to Unlearn

11:32 Take the First Step: Beating Analysis Paralysis with Action

14:17 Scaling Up: Running Out of Cash & Learning the BRRRR Method

16:59 Creative Financing Deep Dive: Seller Finance, Sub-to & Balloons

20:57 Favorite Deals & Partnering Up Using Other People’s Money

21:33 Raising the Down Payment + 1031 Into Seller Financing (5-Unit Deal)

23:00 What He’d Do Differently: OPM Sooner & BRRRR After the First Duplex

24:18 Flip vs Hold: Wealth-Building Mindset, Leverage, and Today’s Market Risk

25:36 OPM Playbook: Partners, Private Money Terms, JVs & Structuring Deals

27:21 Friends & Family Funding + Skin in the Game (Even Teachers Have Money)

29:16 His Business Today: Full-Time Realtor, Investor Niche, Flips/Wholesale to Buy Rentals

31:40 Sky’s the Limit Podcast + The “BADASS” Rapid-Fire Segment Begins

32:39 Books & Advice: Rich Dad, Poor Dad, Who Not How, Never Split the Difference + Take Action

35:46 Drive, Goals & Systems: Generational Wealth, 200 Doors, Assistants, CRM, Morning Routine

39:46 Defining Success + Where to Find Mike (Podcast, IG, Website)

41:12 Wrap-Up & Show Outro: Subscribe, Follow, and Join REIGN

 

🔗 Learn More & Connect with Jen Josey:
https://www.therealjenjosey.com – Real estate investing resources, podcast episodes, and more.

👑 Join the REIGN Mastermind:
https://www.reignmastermind.com – Network with real estate investors nationwide.

🔥 Stuff Jen Josey Loves (Recommended Tools & Resources):
https://www.reignmastermind.com/resources – Handpicked tools, books, and services for real estate investors.

📚 Buy Jen Josey’s Book: From Beginner to Badass
https://a.co/d/bstKlby – Step-by-step guide to real estate investing success.

🏠 Grow Your Rental Portfolio with Jen’s Coaching:
https://rentalproppro.com/booking?am_id=reign – Book a session and scale your rental business.