Today we’d like to introduce you to Jesse Smith.
Hi Jesse, it’s an honor to have you on the platform. Thanks for taking the time to share your story with us – to start maybe you can share some of your backstories with our readers?
I moved to North Kansas City in 2013 after getting engaged to my wife, who is from the area. We started investing in real estate about a year later, and by 2019, we had 14 rental units. I do all of the purchasing, renovation, tenant screening, and maintenance myself. I’ve also started a YouTube channel to teach others how to do this.
Additionally, I built a website called Loophole Travel to teach people how to use credit card miles/points to travel the world. I’m currently self-employed/semi-retired, a full-time dad to two little girls, and an amateur cabin builder.
Alright, so let’s dig a little deeper into the story – has it been an easy path overall, and if not, what were the challenges you’ve had to overcome?
The road has been pretty smooth. I used to work a government job when we first started investing in real estate. Once the rental income provided sufficient cash flow to leave my position, I ramped up the real estate holdings.
The biggest struggles have been in the form of difficult tenants – I once had a tenant living with 22 dogs in one of my properties, while refusing to pay rent. That wasn’t much fun to handle. Additionally, YouTube, and building an online presence in general, has been a very slow growth process.
Alright, so let’s switch gears a bit and talk business. What should we know about your work?
I’m mostly known as a real estate investor and deal maker.
I’ve always had a knack for finding great deals, whether on properties, travel, services, or items of interest. My degree in finance also helps me identify investment strategies that set up long-term wealth creation. My investments, both in real estate and index funds, have allowed me to create the life I want.
Right now, that looks like spending time with my young daughters, serving in city leadership, and building a lake cabin in my spare time. I’m currently focusing on building a YouTube channel to help others learn to invest and build their financial future.
If we knew you growing up, how would we have described you?
Growing up, I was a little businessman. I used to draw pictures, like most kids, but then I would make copies, staple them together, and sell them as coloring books. I also bought and sold trading cards, computers, and just about anything that held my interest.
Otherwise, I was into sports (baseball and golf) and playing the drums (marching band and with friends).
Contact Info:
- Website: www.loopholetravel.com
- Instagram: @looholetravel
- Youtube: https://www.youtube.com/channel/UCyoaEEBrJFELhC6S4U0jVVw

