Feb 16, 2026
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.