I’ve been an investor for 20 years. I’m confident in my abilities and intimately familiar with my industry. Very little comes as a surprise to me anymore, and the stress that once overwhelmed me has significantly diminished, even in new ventures! I will take on new challenges with open arms and the stress during the day minimally affects me.

Nevertheless, there’s one moment that can shake even the most seasoned professional: waking up at 4:00 AM. In that quiet, predawn hour, every worry seems amplified when you are half awake and half asleep.

Entrepreneurship is rife with unexpected challenges, and my first property flip was no exception. What began with a harrowing struggle for financing became one of my most educational experiences and ultimately, a tale of resilience and redemption. Hopefully, my struggle will help you avoid some of the rookie mistakes I made if its your first flip! Don’t worry, I’ll add a few lessons and take away here, so you’re not lost! Lol

The Bumpy Road

The journey started with a staggering 202 calls to secure 100% financing. Well, almost 100%. I needed $600.00 to close the deal. So, Scotty, my brother let me borrow it! When the approval finally came, I felt exhilarated but naive to the trials ahead.

A little while later, I heard them announce that limbo was coming up. I was excited to impress her and show off just a little. I noticed she went to change skates for the limo, she went from in-lines to quads (four-wheel skates) We both got in line for the contest. It started with 30 kids and quickly narrowed down to just me and her. I am on the second bar to the bottom and I hit the bar and was out. She did the lowest bar and won and In the end, I lost. I was devastated, embarrassed and humiliated.

Accountability can be intimidating, yet it's one of the most powerful assets for an entrepreneur. Taking responsibility for your actions grants you control and empowers you to enact meaningful change.

Ever noticed how some people are covered in name brands, flaunting their designer bags and flashy cars? It often seems like these folks want to feel rich or have others think they're rich. But there's a subtle difference between being rich and being wealthy. 

Here's the thing: Truly wealthy individuals don’t waste their money on keeping up with the Joneses. They understand that real wealth doesn’t scream for attention. It’s not about constantly buying the latest trends or stacking up purses in their rooms.

People often ask me, "Jackie, why aren’t you a realtor?" The answer is pretty simple: I break far too many rules to fit in that box. In the world of real estate investing, sometimes you have buy a house without ever stepping foot inside first. It’s risky, it’s thrilling, and it’s what I love.

Back in my early 20s, I crossed paths with a businessman named Mitchell. Mitchell was in the commercial construction business, building Home Depot stores and other big-name facilities. Despite his serious reputation, he was drawn to my hustle and energy. Our bond formed over an unusual situation—I found out a mutual friend of ours was stealing 50K in another deal from Mitchell.

When Bella was a baby and I was still a struggling young mom, I found solace in parenting magazines. They were filled with ads for dreamy hotels and family-friendly destinations. One particular ad, featuring a shark slide at Atlantis, Paradise Island in the Bahamas, captivated my heart. I wanted to be able to take Bella there so badly. It seemed like an unattainable dream back then—I could hardly afford diapers, let alone a luxurious vacation. But I clipped that ad, folded it carefully, and kept it in my wallet. Little did I know, that small piece of paper would fuel my entrepreneurial journey.