Lenaille Smith shared their story and experiences with us recently and you can find our conversation below.
Lenaille, really appreciate you sharing your stories and insights with us. The world would have so much more understanding and empathy if we all were a bit more open about our stories and how they have helped shaped our journey and worldview. Let’s jump in with a fun one: What is a normal day like for you right now?
Since pausing my wholesale real estate business, it’s been managing my construction company and watching over projects.
Can you briefly introduce yourself and share what makes you or your brand unique?
My name is Lenaille “Lenny” Smith a father, entrepreneur, and creative deal maker originally from Cleveland, Ohio, now building businesses and opportunities in Springfield, Missouri. I’m the founder of The Smith Financial Relief Group LLC, an Ohio-based company focused on creative real estate solutions and helping homeowners and investors structure deals that work when traditional financing doesn’t.
After starting in Cleveland, I moved to Missouri to grow my real estate investments under The Smith Financial Relief Group. That journey unexpectedly led me to the demolition industry: I sold a house to an investor who asked if I knew anyone who could handle a demo. I figured out what to charge, jumped in, and 417 Demo LLC was born; now a fast growing demolition and dumpster rental company serving homeowners, investors, and city projects across southwest Missouri.
What makes my path unique is that I built these companies without a safety net, relying on grit, faith, and creative problem solving. I’m known for giving second chances to people who need work, taking complex property situations and turning them into win-win outcomes, and scaling blue-collar businesses using modern branding and social media savvy.
417 Demo started with just me and a few tools; today we own a fleet of branded dumpsters and heavy equipment, handling everything from interior tear-outs to complete demolitions. I also run 417 Roofing Solutions, a trusted local partner for investors and homeowners needing reliable roof work.
I’m passionate about mentoring new real estate investors through my “Creative Wholesaling with Lenny” community, using social media to show how to break into real estate without traditional financing. At the same time, I give back locally sponsoring back-to-school drives and free haircuts for kids, supporting other small businesses, and creating jobs.
Right now, I’m focused on expanding our dumpster rental and demo fleet, growing our real estate portfolio, and creating more educational content for up-and-coming investors. My journey shows how you can start with creative real estate deals in Cleveland, take risks, and build a recognized brand that changes your city and leaves a lasting legacy.
Okay, so here’s a deep one: Who saw you clearly before you could see yourself?
That’s my mother, she made a comment the other day about I post I made on Facebook about how kids blame everything on the teachers and her comment was; remember when we thought it was the teachers until I figured you out. Definitely my mother lol
Was there ever a time you almost gave up?
I quit every week lol… No, but seriously, at times the road gets so rockey that you want to sometimes just stop right? Just shut the business down and move on to something less stressful. But then I remember why I do it and who I do it for and that’s enough to keep me showing up everyday in my best capacity.
Next, maybe we can discuss some of your foundational philosophies and views? What’s a belief you used to hold tightly but now think was naive or wrong?
That you needed money and credit to do business when you only need a customer.
Thank you so much for all of your openness so far. Maybe we can close with a future oriented question. What is the story you hope people tell about you when you’re gone?
I hope people say I was a man who bet on himself, created opportunities where none existed, and pulled others up with him. That I came from Cleveland with nothing guaranteed, trusted God, worked relentlessly, and built businesses that gave people second chances and families financial stability. I want to be remembered not just for tearing down buildings, but for tearing down obstacles showing that with grit and creativity you can rewrite your life and impact a community. Most of all, I hope my kids and everyone who worked with me can say, “Lenny didn’t just chase success he built a legacy that helped us dream bigger and do better.”
Contact Info:
- Website: All cash buyers.org
- Facebook: Lenny Smith
- Youtube: @wholesalingwithlenny
so if you or someone you know deserves recognition please let us know here.
