Today we’d like to introduce you to Kevin Oldham.
Alright, so thank you so much for sharing your story and insight with our readers. To kick things off, can you tell us a bit about how you got started?
My story starts in a skate shop in Topeka, Kansas. My mom owned Square One Skateboards, and I grew up watching her pour everything she had into that business. When it closed, she walked away with nothing. I didn’t really have language for it back then, but I was watching what happens to the majority of small businesses in America: they build something, and then one day it just ends. That lesson really stuck with me.
From there, I went deep into the world of helping people sell things, from helping launch a couple of marketing companies to becoming the CMO and co-founder of United Real Estate. I’ve helped move hundreds of millions of dollars in assets in my career, everything from distressed properties during the Great Financial Crisis to trophy properties and estates.
A couple years ago, I ran into a statistic that roughly 80% of businesses listed for sale actually never sell.
Millions of owners will try to exit over the next decade, and most of them will end up exactly like my mom did. Not because their businesses aren’t valuable, but because nobody ever helped them build a business that works without them, and the traditional selling process just isn’t built for them.
I became a Certified Exit Planning Advisor and a Certified Value Builder, and we partnered with John Warrillow’s Value Builder System.
Every founder is eventually at one of two crossroads.
Either they need to fall back in love with their business, or they need to exit it like a hero. We call it Love It or List It.
Some founders just need to fix what’s broken, get themselves out of the day-to-day, and remember why they started. Others are done, and they deserve a process that actually pays them for what they built, rather than becoming another statistic.
Today, Diffactory does both. We help founders build more valuable, more sellable companies, and when it’s time to go, we run an accelerated sale process that gets verified offers in 60 days instead of letting a listing rot on the market for 18 months.
I’m basically spending my career making sure other founders don’t end up where my mom did.
We all face challenges, but looking back would you describe it as a relatively smooth road?
I don’t want to speak in the past tense here. I think it’s still not a smooth road. Entrepreneurship is full of ups and downs, and there have been a couple of times when we, as I like to say, almost crashed the plane. I’m thankful that we’re still in the game 11 years later and helping others exit with dignity.
Alright, so let’s switch gears a bit and talk business. What should we know?
Diffactory is an exit planning and M&A advisory firm based in Lee’s Summit. We work with founder-led businesses doing $250K to $20 million in revenue, and the whole thing comes down to one idea: we help founders love their company again, or exit it like a hero.
On the front end, we’re value acceleration experts. We assess your business across the eight drivers buyers actually pay for, then work with you to fix what’s dragging down your value, whether that’s owner dependency, weak systems, or nonrecurring revenue. The same work that makes a business sellable makes it more profitable and easier to run right now.
On the back end, we’re business brokers and M&A advisors who actually get deals done. Here’s the stat that drives everything we do: roughly 80 percent of businesses listed for sale never sell. That’s a process problem, not a market problem. So we built a different process. We’re a seller-side fiduciary running an accelerated sale model, the same auction and accelerated marketing mechanics I spent years running at the national level, applied to Main Street businesses. Verified offers in 60 days, closed in 150 or fewer.
What sets us apart is that we’ve lived it. I’m a three-time founder, a Certified Exit Planning Advisor, and an investor in over 30 companies. We’re not theorists. Whether you’re three years from selling or you need out yesterday, we know the path because we’ve walked it.
Are there any books, apps, podcasts or blogs that help you do your best?
I keep my favorite books and most impactful ones on my desk:
– Purple Cow by Seth Godin (it’s about being a remarkable business)
– Buy Back Your Time by Dan Martell
– Walking to Destiny by Christopher Snyder
– Built to Sell by John Wurlow
– The Obstacle is the Way by Ryan Holiday
Contact Info:
- Website: https://diffactory.com/
- Instagram: https://www.instagram.com/thekevinoldham
- Facebook: https://www.facebook.com/koldhamkc/
- LinkedIn: https://www.linkedin.com/in/kevinoldham
- Twitter: https://x.com/koldhamkc
- Youtube: https://www.youtube.com/@kevinoldham
- Other: https://www.skool.com/founderhq
