What You Can Learn From the Worst Year of My LIFE in Real Estate

Mindset5 min read

I hope you NEVER experience anything as remotely terrible as my 2008…

Patrick Riddle
Patrick Riddle

Have you ever been so worried about something in your real estate business that you couldn’t asleep? And even when you FINALLY do, the split second you wake up… your worst fears flash across your mind?

Allow me to elaborate…

My Real-Life Horror Story

It was January 1, 2008 — the first day of the worst year of my life.

The previous quarter, my investment business went through $847k in cash. With 7 evictions filed, 6 renovations in progress (plus a couple houses waiting to be renovated), and several homes in move-in condition listed for sale … can you say CASH FLOW NIGHTMARE?!

What had I done? How did I let this happen?

No matter how bad a situation seems… it’s important to keep in mind that everyone, EVERYONE makes mistakes… doesn’t matter if you’re brand new to real estate investing or if you’re a seasoned veteran.

You’re going to make mistakes, period! 

BUT, it’s how you respond, how you react, what you learn… that makes the difference.


I remember when my mentor said that when you’re actively investing in real estate over time… it’s not a matter of if someone will file a lawsuit against you (whether it’s a tenant, contractor, seller, lender, etc.), it’s a matter of when.

I read about a poll that was done at the end of the 19th century. People were asked, 

“If you were to get rich, become wealthy, how would you do it?”

The answer: build a business. 

That same poll was conducted 100 years later and the answer, unfortunately: sue someone. 

It just goes to show you how the mindset of the masses has shifted.

In real estate investing, when things go south, it can mean broken agreements, payments falling behind, liens, judgments, foreclosure, and bankruptcy.

You’ve undoubtedly heard many stories of hardship over the years, especially with the 2007/2008 crash, from huge multimillion and billion-dollar real estate investment companies, developers, banks, mortgage companies… 

But regardless of the adversity faced, there are key lessons to be learned and leveraged into your next deal, your business, your personal life. And I was about to learn all about ‘em.

Yeah, my 2008 was THIS bad

When I woke up on January 1, 2008, I no longer had an income. 

My business partner and I stopped paying ourselves… and started putting ever dime we found into the business. We drastically cut expenses, let employees go, got as lean as possible. I stopped making payments on my personal residence (a beautiful home on the Ashley River in Charleston), and my diet consisted of ramen noodles and peanut butter and jelly sandwiches.

In 2008:

  • my business model failed
  • my dream home went into foreclosure
  • I got a serious injury (after training harder than I ever had before for the upcoming beach volleyball season), which took me out for the entire year
  • I had to renegotiate with my private lenders (NOT a position you want to be in… EVER!)
  • I totaled my Mercedes
  • my girlfriend at the time moved a few thousand miles away
  • and to top it all off, I got sued for the first time

I was emotionally, physically, financially distraught. I was confused. Mad. Pissed off. But at who? Myself.

I didn’t blame the market. I blamed my leadership of our investment company coming into the market. And that made all the difference. By taking responsibility for my mistakes, I was able to learn and grow a tremendous amount from them.

I desperately wanted to help as many investors as possible AVOID the big mistakes, heartaches, and pains that I had to go through. 

This became my “why” — the driving force for my comeback… that continually inspired (and continues to inspire) me to do whatever it took, for however long, however hard… to build my business again from the ground up. 

My motto: Persist Until!

So, what’s your “why?”

What’s fueling you to take MASSIVE action and build a thriving, profitable investing business?

Your “why” doesn’t have to be related to real estate. Although, if it were, maybe you’re passionate about improving neighborhoods and want to buy fixer-uppers and renovate them, or you want to help low-income families with nice affordable housing. If that’s what excites you, great! If not, that’s ok too. Because real estate investing is a vehicle.

  • What do you love? 
  • What excites the heck out of you just thinking about it? 
  • Would you like to start a charity? 
  • Help impoverished children in a 3rd-world country? 
  • Become a professional snowboarder… so you can inspire others to follow their dreams?

Whatever it is… use that as the motivation and inspiration to keep moving forward… no matter where you are today, no matter what other people say, no matter what obstacles arise.

If you’re going through some difficult times — as you can see, I’ve been there, so I know how it feels to have the world come crashing down on you…

No matter how bad things are, do your best to focus on the future, on solutions… rather than on problems and the past. Clarify your “why.” Because that’s the driving force that will keep you going, despite inevitable setbacks.

I hope you NEVER experience anything as remotely terrible as my 2008…

But, just as I learned from my mistakes and came out OK on the other end — if you ever find yourself in a similar tragic place, you’ll know it’s completely possible to come out of it.

I did it. You can too.