Hey, business owners! If you’re reading this, chances are the thought of selling your company has crossed your mind—maybe as a fleeting “what if” over coffee, or maybe it’s keeping you up at night. I’ve been there. After scaling businesses like Five Doors Network and Owen Capital, I’ve stared down that crossroads myself. It’s a big deal, and it’s not just about the numbers—it’s about you. So, let’s hit pause and walk through some key questions to ask yourself before you take the leap. At Icon Business Advisors, we’re all about helping you think it through, and I’m here to get the ball rolling.

1. Why Am I Selling?

Start with the big “why.” Is it burnout, like I felt after years of grinding? Are you ready to retire and sip margaritas on a beach? Or maybe you’ve got a new venture itching to launch. Your reason shapes everything—timing, price, even who you’ll sell to. Be honest with yourself. If it’s just a rough patch, maybe you don’t need to sell; maybe you need a break or a better team. Whatever it is, nailing this down is step one.

2. Am I Ready to Let Go?

This one’s a gut check. Your business might be your baby—mine sure felt like it at times. Can you picture someone else running it? Will you cringe if they repaint the office or tweak your logo? Selling isn’t just a transaction; it’s an emotional handoff. I’ve seen owners pull out mid-deal because they weren’t ready to cut the cord. Think about what “done” looks like for you—financially and personally.

3. What’s My Number?

How much do you need to walk away happy? Not just “what’s it worth,” but what covers your next chapter—whether that’s a nest egg, a new project, or paying off that boat you’ve been eyeing (Center Hill Lake is calling my name!). Too many folks skip this and either undersell or chase an unrealistic unicorn. At Icon, we help you crunch the real numbers—valuation, taxes, fees—so you know your target before the offers roll in.

4. Is My Business Ready to Shine?

Buyers don’t just buy your revenue; they buy your story and your systems. Are your books clean? Is your team solid? Could it run without you micromanaging every move? I learned this scaling Owen Capital—vertical integration looked slick, but it took work to make it buyer-ready. If your operation’s a hot mess, you’ll either scare off prospects or take a haircut on price. Ask yourself: would I buy this today?

5. When’s the Right Time?

Timing’s everything. Are you riding a growth wave, or is the market tanking? Are you selling because you have to (cash flow’s tight) or because you want to (peak value)? I’ve seen owners wait too long and miss their window—others jump too soon and leave money on the table. Look at your industry, your numbers, and your life. There’s no perfect moment, but there’s a smart one.

6. Who’s the Right Buyer?

Not every handshake is a match made in heaven. Do you want a competitor who’ll keep your legacy alive? A private equity firm with deep pockets? A family friend who’ll call you for advice? I once sold a piece of a business to a group that didn’t get the vision—it stung. Think about who aligns with your goals and values. At Icon, we use tech to spot the right fit, but it starts with you knowing what you want.

7. What’s Next for Me?

Selling’s not the end—it’s a pivot. What’s on the horizon? When I stepped back after $450 million in sales at Living TN, I didn’t have a clear “next,” and it threw me. Are you itching to start something

new, mentor others (like I’m doing now), or just kick back with the kids and the dog? If you don’t have a plan, the void can hit hard. Give yourself something to run toward.

Why This Matters

Selling a company isn’t like selling a car—it’s a journey, and these questions are your roadmap. Rush it, and you might regret it. Mull it over too long, and you might miss out. I’ve been on both sides of the table, and I can tell you: clarity is king. That’s why Icon exists—to guide lower middle market owners like you through the fog with straight talk, smart tech, and a team that’s been there.

So, take a beat. Grab a notebook (or a napkin—I won’t judge) and jot down your answers. If you’re stuck—or ready to dig deeper—drop me a line. We’ll chat, no pressure, about where you’re at and how we can help. Because at Icon, your exit isn’t just a deal; it’s your legacy—and we’re here to make it a win.

Daniel Askew is the CEO of Icon Business Advisors, a Nashville-based firm empowering lower middle market businesses to thrive. When he’s not asking big questions, he’s chasing his sons or plotting his next outdoor adventure.