Interview with Side Hustler Jay Helms on his Journey to Financial Nirvana

I am so excited to introduce you to Jay Helms, from Gulf Breeze, FL, a husband, a father, corporate america minion, and a side hustling real estate investor juggernaut. A cool fact about him – he met his awesome wife at a reality TV show, ‘The Catch’ in Costa Rica.

When he’s not with the kids and his awesome wife – he writes on  Bigger Pockets and his own blog –

His most recent accomplishment includes buying a 42 unit apartment complex for $700K and with $200k renovation budget.

I wanted to interview Jay, a busy father, who juggles a career, life, kids and real estate investments to inspire you to stop settling in life, to empower you to design a life that is purposeful and meaningful to you.

His interview will:

  1. Inspire you to develop a strong ‘WHY’ with real estate investing

  2. Provide you his top 5 tips for juggling life, kids, real estate investments and a career

  3. Arm you with his top notch real estate investing rules that make or break a deal;

  4. Make you think twice BEFORE throwing your hard earned money to a  shoddy property deal even if it looks like a great deal.

Without further adieu, here’s his interview.

  1) How did you get started investing in real estate?

We really started with the purchase of what we call The Little Yellow House. 1 bed / 1 bath 600 sqft home. Bank foreclosure in a part of downtown that was starting to see revitalization. Purchased for $22k, spent $9k in rehab, rented it the month it was ready for $600/month. It stayed occupied since we bought and we never thought we’d sell it but we did. Just last month for $50k. That property cash flowed $300/month and provided us a 77.5% return (when including the sale). [  ] But, growing up, my grandparents, maw-maw & paw-paw, owned what they called a tenant building. It was 10-15 units and they lived in the house next door. Maw-maw kept the books, paw-paw was the handyman. So growing up, I saw them work this business. It didn’t hit me that I could follow in their footsteps until 2014 (30+ yrs later). Growing up around that environment gave me a sense of confidence that I could be a successful real estate investor – and unfortunately I didn’t recognize this until 2014 but at the time we purchased the Little Yellow house, we started tracking our net worth and reading a lot of books about building wealth. After a year and a couple more acquisitions we quickly saw how real estate was going to be able to exponentially grow our net worth…we were hooked.

2) What was your ‘aha’ moment that drove you to invest in real estate?

My ‘aha’ moment was what I call the Trifecta of moments that pushed us to invest. In 2014 (a) I stumbled upon the book Rich Dad Poor Dad by Robert K (b) we had our first child (c) the company I worked for the last 10 yrs was acquired by a larger company and let’s just say the acquisition wasn’t as smooth as everyone hoped. I needed to find a way out and through REI I decided to setup a legacy building platform

3) What drove you down the path of scaling your real estate investment business?

My kids and my wife. Designing a lifestyle where I have more free time to spend with them.


YEP!!  Real estate investing is a great vehicle for designing your life aligned to you!  But I highly recommend scaling according to your LIFESTYLE, a great model I coined for buying real estate.


4) Why invest in real estate versus other investment vehicles?

I have found out Buy & hold just makes sense to me, think of path of least resistance. After our first 2 transactions, seeing the cash flow, see the net worth growth, I was hooked. In the past I have invested in stocks, they just didn’t work for me – Buy high, sell low and it’s not that I was just listening to Cramerica and acting on his actions, I’d spend a few hours each week learning about companies before I invested and I still lost money.

5) What are your top 5 tips for juggling life as I understand your wife is your business partner, your full time job and two kids under 4??!!

  1. Be ok with chaos!