My Real Estate Story: From Working For Free To Owning a $1.2 Million Portfolio

My Real Estate story is a OneSavvyDollar series where we interview millennials who have successfully invested in real estate because; “real estate is an imperishable asset, ever-increasing in value. It is the most solid security that human ingenuity has devised. It is the basis of all security and about the only indestructible security”.- Russell Sage.

Can you tell us a bit about you and what kind of real estate investor you are?

I am a value add self-storage investor in the southeast. I got started investing back in college where I decided to work for a mentor for free for over a year to learn the ropes.

During that time, I did it all and was thrown in immediately to every aspect of the business. Wholesaling, house flipping, residential rentals, apartments, and eventually commercial property like self-storage.

When did you decide to get into real estate? What was the aha moment for you?

I read Rich Dad, Poor Dad in college and knew instantly I was not going to get to where I wanted to go by being an employee. I instantly set out to learn all I could about acquiring assets that cash flowed.

To build wealth, you can either start a business, invest in the stock market or real estate. Why real estate?

I decided on real estate for five reasons; control, cash flow, leverage (time and money), tax benefits,  appreciation, and owning a real asset. Also, real estate will always be needed.

Most people think you have to quit your job to invest. Did you keep your job or are you involved in real estate full time? How has the experience been (either way?)

I started in college so I did not have a full-time job but was a full-time student.

I worked at a bar at night to make money, went to class in the mornings until about noon, and then worked for my mentor for free between when I got out of class and when I would go to work at the bar.

Tell us about your first home/deal. How did you find it? How much did it cost and do you still own it?

The first investment I put cash into was a storage facility. We found it off-market – direct mail. It was $500,000, we arranged a lease option with only $30,000 down. I still own it today, but actually looking to sell it for $1,200,000.

What are some mistakes you made during your real estate journey?

All of them! Haha – my journey has been littered with mistakes, but that’s why I have been able to make progress so fast. The biggest mistake I made was in the beginning when my limiting belief was that I needed to have a ton of money in order to start buying real estate.

Was there any time during your journey where your friends and or family challenged your plans to get involved in real estate?

Most people who knew that I was working for free thought I was crazy for doing so but it worked out pretty good for me. I had the vision of what I wanted to do and who I wanted to be.

I was not going to let their opinions change that.

As an investor, what is your real estate investing strategy and how do you determine if a property is worth the investment?

Value add and development deals. Commercial only. The primary objective is a 30% internal rate of return (IRR) and a 15% cash -on-cash after refinancing enough to get all my investor’s capital out of the deal.

Do you invest in state or out of state and which would you consider to be harder?

I do both. They are of equal difficulty. The main thing is to make sure you have the right systems and team in place.

Were any resources such as blogs, books, podcasts particularly helpful to you to get started? How did you find the inspiration to get started?

Rich dad, poor dad. Cash flow quadrants. Real Estate Espresso podcast is pretty great. I wrote my book, Skip The Flip: Secrets the 1% Know About Real Estate Investing as a follow up to rich dad poor dad.

That book gives you the mindset that you need, my book gives you the details you need in order to get started investing in real estate. It’s like the why and the how.

Let’s talk about leverage: would you advise reinvesting your profit to pay down the loan or acquiring more using your profits?

Never pay off debt unless it’s mortgage constant is higher than the rate of return you can get in a new investment. Which debt is rarely more expensive than what you can earn in a new deal

If you could do it all over again, what would you do differently?

I would say to be more proactive in meeting other people and building my network. The greatest assets in my life are strong and powerful relationships. I also wish I could have started when I was 12.

What advice would you give anyone who is trying to buy their first home or become a real estate investor?

Just do it. You can’t learn everything before you start. You are going to make mistakes so don’t get down on yourself when that happens. Consider it part of the journey and a sign of progress. Then when you make a mistake, you can actually get excited about it rather than down on yourself.

What markets do you primarily invest in and which do you avoid completely?

Sunbelt states with growing submarkets. I avoid any area with a shrinking population base.

How can our readers keep in touch with you?

I would love for everyone to get a free copy of my book in pdf or audiobook from You can also find me on instagram (@haydencrabtree)


Congratulations Hayden! Wishing you much success in your real estate investing journey!

About Ogechi

Hello, I'm Linda Ogechi. I'm a financial educator, real estate investor, and founder of OneSavvyDollar. I write to empower you into saving more, paying off debt, increasing your net worth, and building real wealth so you can achieve financial freedom

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