Meet RE Investor Guy – degenerate gambler to real estate investor

Good morning,

Earl Nightingale once said that ‘you become what you think about’. The concept is that if you focus on one goal – you will certainly achieve it. Suggesting the goal is achievable, put in the hours of study, and take action.

The problem is that most people in Nightingale’s words ‘think about nothing and then become nothing’. This week’s investor was able to avoid this trap by focusing his energy on something constructive.

Rather than thinking about gambling he began thinking about real estate. In turn he started predictably hitting jackpots where the odds were in his favor.

It is my pleasure to introduce you to RE Investor Guy

How many doors do you have?

Currently I have 10 doors

What got you into real estate investing?

I was a degenerate sports gambler and knew if I didn’t redirect the energy I put into gambling into something more positive, my life would have spiraled down hill fast and so I started to look around and think about what might be a good pivot.

That’s when I found real estate. My dad has been investing in RE since before I was born so that is what initially sparked my interest in buying rentals. I figured at the time that RE was a far more calculated and rewarding “gamble” (than sports gambling) where the odds were in my favor if I did my due diligence. And so I started buying single family rentals in 2016 and progressed from there.

What markets do you operate in?

Hudson Valley, NY and Worcester MA

How would you describe your portfolio?

A mix of small MF and STRs

What are you currently buying?

My focus right now is to find unique, large parcels where I can have multiple STR units on one parcel.

Tell us about your biggest mistake in real estate?

Purchasing an older property WITHOUT first getting a licensed inspector. Hiring a good property inspector is worth its weight in gold.

Don’t make the same mistake I did, it wound up costing me 15k in repairs that I missed when I inspected the property with a contractor buddy.

Tell us about your biggest win in real estate?

Buying a MF property for 595k off-market and the appraisal came in at 723k. We made 128,000 without doing any work to the property. After we renovated one unit (the other units were already in good shape), we did a cash out refinance and the new property value came in at 800k.

Outside of real estate what else do you invest in?

Stocks, ETFs, and index funds.

Books people should read before investing

Rich dad, poor dad is a good first book to read before you start any type of investing.

The Book on Rental Property Investing by Brandon Turner is great for those that want to get started in RE investing.

What advice would you give to a new investor?

Develop a tribe of RE investors and constantly share new ideas with each other. Create a mastermind, help each other grow. This will speed up your learning curve.

Before you buy your first property, make sure your finances are in order, you have reserves allocated for the property and that you have steady income so you can be able to handle unforeseen expenses that come with owning property.

RE Investor Guy (@REinvestor_guy) / Twitter
RE Investor Guy (@REinvestor_guy) /
Real Estate Investor 🚀 | I’ll show you how to buy good RE | Currently own 10 doors in Hudson Valley NY and Worcester MA | Based in NYC

This week on the podcast

As a manager at a Pizza joint then recruiter for the National Guard – he thought he was doing pretty well. That is until he discovered private money. 

His discovery of private money allowed him to super charge his portfolio. Going from 8 doors to over 50 in just 2 years! The incredible thing is that when he started – he didn’t have a huge network of wealthy friends. He had to network, source deals, manage rehabs, get refinancing, all while still working a W2. His grind is admirable! 

Listen on:

Apple Podcasts


Google Podcasts

Enough Business

Piggybacking off my earlier thoughts on Earl Nightingale…

First off I have to mention that Nightingale has a voice lost to time. His deep & smokey voice crackling over vinyl is so reassuring. Like he speaks for all our ancestors who experienced the old world hardships.

Namely being born in 1921. Where he came of age during the Great Depression before seeing the world fall apart before his eyes. And I mean this literally. Nightingale was one of 15 marines who survived the sinking of the USS Arizona at Pearl Harbor.

This man experienced some of the darkest days in our country’s history. So when he says “you become what you think about” we should all take note.

I’d like to close this week’s newsletter with a quote from his masterpiece, The Strangest Secret:

“The human mind is much like a farmer’s land. The land gives the farmer a choice. He may plant in that land whatever he chooses. The land doesn’t care what is planted. It’s up to the farmer to make the decision. The mind, like the land, will return what you plant, but it doesn’t care what you plant. If the farmer plants too seeds and one a seed of corn, the other nightshade, a deadly poison, waters and takes care of the land, what will happen?

Remember, the land doesn’t care. It will return poison in just as wonderful abundance as it will corn. So up come the two plants and one corn, one poison as it’s written in the Bible, “As ye sow, so shall ye reap.”

The human mind is far more fertile, far more incredible and mysterious than the land, but it works the same way. It doesn’t care what we plant … success … or failure. A concrete, worthwhile goal … or confusion, misunderstanding, fear, anxiety, and so on. But what we plant it must return to us.”

Link to the full article

Monday’s podcast:

Exiting real estate – why John sold his portfolio

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