How Do You Make Money in the Market?

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When things are going good, I hit it. When things are going bad, I run and that's how I do with everything. It's fun, it's an obsession. Similar to poker or gambling. When I'm winning, I lean in really hard but I hate losing. Losing is painful to me. Whenever I'm losing in anything, I run away instead of trying to double down and get my loss back,. I just run. That put you ahead of a lot of investors certainly in 2022 because big losses came on the table that year and I wasn't taking any. Most other times I'm looking for longs, it's easier to make money longs and shorts.

Patrick Donley talks with Jeff Higgins about building a self-managed portfolio, managing remote rentals, and his learnings from being a men’s success coach.

Jeff is a real estate investor with a portfolio of 87 units — 57 in Massachusetts and 30 in Florida. He self-manages his properties and is also a licensed broker in both states. He also works as a men’s success coach for the Fraternity of Excellence, where he helps men find their inner strength and counsels them on their finances.

IN THIS EPISODE, YOU’LL LEARN:

00:00 - Intro

05:15 - How Jeff became involved with the Fraternity of Excellence and men’s success coaching.

07:27 - What his inspiration to invest in real estate was.

16:41 - What entering the Florida market has been like.

27:43 - How he trained his handyman to handle property management.

29:02 - Why he prefers Section 8 rentals.

35:01 - How he self-manages 87 properties in two different states.

42:25 - Why the poem “If” by Rudyard Kipling is his favorite poem to learn to be mentally strong.

52:54 - What the most common mental barriers holding people back are.

And much, much more!

*Disclaimer: Slight timestamp discrepancies may occur due to podcast platform differences.

BOOKS AND RESOURCES

Join the exclusive TIP Mastermind Community to engage in meaningful stock investing discussions with Kyle and the other community members.
Robert’s book The Everything Guide to House Hacking.
Rich Dad Poor Dad by Robert Kiyosaki.
Richer, Wiser, Happier by William Green.
The Confident Mind by Dr. Nate Zinsser.
How I Turned $1000 into Five Million in Real Estate by William Nickerson.
How to Make Money in Stocks by William O’Neil.
Fraternity of Excellence.
If by Rudyard Kipling.

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