As entrepreneurs, we often find ourselves continuously striving to achieve our dreams. After a few flips, I thought I was on the right track. I wasn’t where I wanted to be yet, but I felt I was making progress.

Then, one day, something happened that changed my perspective forever.

A friend of mine, Kristina, came over for a BBQ. She was only a few years older than me and had just parked her brand-new Jeep outside.

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.

Imagine this: it's my daughter’s 12th birthday, and we're at an escape room. I thought it would be nothing more than puzzles taped on walls, but boy, was I wrong. We had a blast! When we exited the room, my daughter casually suggested, "Mom, you should open an escape room."

Now, anyone else might have brushed it off, but I remembered something crucial. By turning the word “can’t” into “how,” anything becomes possible. It's like unlocking a superpower. So, why not build an escape room? Hmm How can I build an escape room?

Time and time again, I see talented individuals with immense potential hindered by their own self-limiting beliefs. Despite their enthusiasm, they rattle off countless reasons why they "can't" achieve success. Whether it's being a parent, lacking spousal support, or financial constraints, these reasons become roadblocks.

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.

As an entrepreneur, I've faced my share of challenges, but none loomed larger than the fear of losing my home—a fear rooted deeply in my past.

When I was a little girl, my stepdad seemed like an ideal father figure. He was wonderful to my mom, my siblings, and me. We lived in a beautiful house, and he appeared every bit the perfect businessman—always in a suit, never drinking or smoking, nothing that was bad for his body. But beneath this façade, was something different, he was a heroin dealer, a figure straight out of "American Gangster."

I wanted an inground pool. All of the quotes I received were around 80,000 which I thought was pretty high. So, I thought, “why not try to build my own pool”, Despite knowing nothing about pools.

Although we were considerably competitive with each other, watching my older brother Scotty, growing up was nothing short of inspiring. Every Christmas, while other kids were enjoying their break, he was out there hustling, selling poinsettias from my dads greenhouse to every business in town. No sleeping in, no distractions—just pure, unwavering commitment to his goal.

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.

I scoured the tax rolls, hoping for a contact number, but nothing turned up. Every once in a while, I'd see people coming and going from the property, but I wasn’t able to catch them. I noticed there were printed flyers from wholesalers taped to the door. They looked like they had been there for some time. I didn’t want to do the same thing and I was sure the mass-printed flyer wasn’t going to work. I thought, why not add a personal touch and make it feel human?

I grabbed my trusty post-it note pad and wrote:

“Hey! I’m Jackie and I love your house and and was wondering if you would be interested in selling it. Call me at [my number].” 📮💛