Rental Property Investor · NH · Member since 2023 · 447 posts · 421 votes
We'd just bought the most expensive 2-family in Manchester at the time
Honestly, they had a point.
It was one of the rougher houses on the market, in a great neighborhood. It barely passed FHA. I sold stocks and pulled together my crypto just to get the down payment.
I wasn't a licensed agent yet. I had zero investing experience beyond watching my parents and my wife's family do it 20 or 30 years earlier.
We bought it in February and moved in that June. In between, we did all the work ourselves. Hardwood floors, paint, ripped out every drop ceiling, a new kitchen and a new bathroom. Late nights and early mornings the whole way.
Then both upstairs tenants moved out when I asked for a rent increase that was still below market. So all of a sudden we had two empty apartments and a lot to learn.
And it was still the best financial decision we've made.
Once it was rented, we lived there for about $700 a month. That building taught me more about owning real estate than anything I'd read. It's a big part of why I got my license and why I do what I do now.
What was the moment you realized you had to own something?
Thanks for sharing this, I like how you mention you learned more buy doing more than anything you read! This is the ah ha to me. It can be easy to get stuck in YOUTUBE university and turn the education into a favorite pastime. Always learning and never acting! The simple truth is real estate is hard, but so is life. real estate tends to reward those that can endure over a long period of time!
Ive had several ah ha's. House hacking a town house was one of them when I was living for ~$500 a month, 1031 exchanging one property into several and having my rents pay my primary mortgage was another. Education is important but applying what you learn and having the courage to take action is where the real rewards come from!
Andrew, I love this — and as an agent, I watch people have that exact moment in real time. It's usually not the math that tips them; it's the first time they pay rent and realize the number on the check is higher than the mortgage payment on a place they toured last month. Your point about friends and family is the part nobody warns you about: the people who care about you most are also the most invested in you staying comfortable, because your risk feels like their worry. My take from the other side of the closing table: the ones who make it aren't the fearless ones, they're the ones who get educated enough that the fear gets specific instead of vague. Specific fears you can underwrite. Vague ones just keep you renting.
I love your point on friends and family! I am here, because I am trying to get into the self-serve car wash industry. Like many, I don't come from money, and I didn't grow up around this, so to say that this pursuit, (which I have been doing for over 3 years now) has been challenging, is an understatement. Almost every member of my family is very risk adverse, and would rather work for 40 years, and hope they can retire off of that rather than try to invest in something like a business or a real estate.
I am young, and I can see the power of investing, and how it can lead to a better life. I love them all dearly, but these past few years, it's been hard to trust my gut, with everyone else's fears surrounding me in a cloud. Add on to that the amount of times you get told "no" in any kind of investing, and it has taken a lot of trust in myself to keep at it this long.
For that and other reasons, analysis paralysis has been a major issue for me.
And thank you for your thoughts as a realtor from the other side of the table about not necessarily being fearless, but educating yourself enough to make your fears specific instead of vague, and that you can underwrite a fear once you can name it.
Until then, vague fears are the boogie man that keeps you from investing. So many people chose to ignore it, and just go to work again today.
Andrew, congrats on the house hack — fellow Candor agent here. I did the same thing with my first purchase in Revere, MA in 2020: buy small, live in one unit, and let the other rents carry the mortgage while you learn landlording up close. That one deal turned into 17+ rental units across 5 buy-and-hold deals, and the habits from house hacking — underwriting conservatively, keeping reserves, and knowing your tenants — still run how I operate today. The doubts from friends are normal; the math and the lifestyle are what matter. Happy to connect and compare notes — DMs open.