Hey there, business warriors! Selling a company sounds like a victory lap—pop the champagne, cash the check, ride off into the sunset, right? Well, sure, but it’s also a rollercoaster that can leave you dizzy, teary, or wondering who you are without your 9-to-5 (or, let’s be real, 24/7). I’ve been there—after scaling Five Doors Network and Owen Capital, I’ve handed over pieces of my soul disguised as businesses. It’s messy, it’s human, and nobody talks about it enough. So, let’s rip off the Band-Aid and get into the emotional side of selling—because at Icon Business Advisors, we don’t just crunch numbers; we get the heart of it too.
It’s Like Breaking Up with Your First Love
Ever built something from scratch? I did—starting with real estate, serving 500 families, then growing Owen Capital into a mini-empire with mortgage, title, and even lawn care gigs. When it came time to sell parts of it, I felt like I was dumping my high school sweetheart. There’s pride, sure—$450 million in sales is no small potatoes—but also a pang of “what now?” Your business isn’t just a paycheck; it’s late nights, big wins, and that one time you fixed the printer with a paperclip. Letting go feels like losing a piece of yourself. Buyers don’t tell you that—and neither do the spreadsheets.
The Guilt Trip’s Real
Here’s a kicker: guilt sneaks up like a ninja. After my kids were born, I shifted gears to focus on family and Owen Capital, but when I sold off chunks later, I wondered—did I let my team down? My clients? That family legacy I’d built as a third-generation real estate guy? I’ve seen owners hesitate mid-deal because they felt they were abandoning ship. It’s not irrational—it’s human. You’ve poured your guts into this thing, and now someone else gets the keys. Cue the existential crisis over a beer (or three).
The Identity Crisis No One Warns You About
Who are you without your business card? For years, I was “Daniel, the real estate rainmaker” or “Daniel, the growth guy.” After selling, I had to figure out “Daniel, the… what?” It’s like when my dog Delilah looks at me funny because I’m not rushing out the door—she knows something’s off too. Whether you’re retiring, starting over, or just chilling with your kids (shoutout to Charlie and Peyton), that shift can hit like a ton of bricks. I stumbled through it until I landed on Icon—helping others became my new “who.”
The Joy—and the Jitters—of What’s Next
Selling’s not all doom and gloom. There’s a rush—cashing out after years of hustle feels like acing a test you didn’t study for. I remember the thrill of my first big exit, dreaming of lake days on Center Hill. But then the jitters kick in: Did I sell too soon? Too cheap? Will the new owners trash my baby?
It’s a tug-of-war between relief and second-guessing. I’ve talked owners off that ledge—sometimes you just need someone to say, “You did good, now breathe.”
How Icon Holds Your Hand Through It
Here’s where we come in. At Icon, we’re not just about valuations and deal terms (though we’re darn good at those—thank you, Betty, our AI sidekick). We get the feels too. I’ve been the guy pacing at 2 a.m., wondering if I made the right call. My team’s been there too—entrepreneurs, operators, humans. We’ll sit with you, hash out the “why” behind your sale, and make sure your exit’s not just a win on paper but a win for your soul. Whether it’s connecting you to the right buyer or just being a sounding board, we’ve got your back—because CEOs need friends, not just advisors.
Take a Beat, Feel It, Then Move Forward
Selling’s a wild ride—equal parts heartbreak and high-five. Don’t bottle it up. Talk to your spouse, your dog, or heck, shoot me a message—I’m a sucker for a good story. Reflect on what you’ve built (you’re a rockstar, admit it), and let yourself feel the messy stuff. Then, let Icon help you turn the page. We’re here for the lower middle market heroes—$5 million to $50 million businesses—who deserve an exit that honors the journey, not just the destination.
So, if you’re staring down a sale and feeling all the things, let’s chat. No stiff suits or cold handshakes—just real talk over a virtual coffee. Because your business isn’t just a deal—it’s your legacy, and we’re here to make it shine.
Daniel Askew is the CEO of Icon Business Advisors, a Nashville crew lifting up lower middle market champs. When he’s not navel-gazing about exits, he’s dodging Nerf wars with his boys or hiking with his wife Rachel.