EPISODE 237: In this first installment of the M&A Master Class Series for Sellers, the Revenue Rocket partners break down one of the toughest decisions for any founder: knowing when it’s time to sell. Mike, Matt, and Ryan explore how to read the signals that you’re ready, the emotional and financial factors at play, and the difference between “selling out” to move on versus “selling in” to grow bigger. Whether you’re feeling burned out, hitting growth ceilings, or just wondering what’s next, this episode helps you self-assess where you are and what comes next in your journey.
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Mike:
Hello, and welcome to this week’s Shoot the Moon Podcast, broadcasting live and direct from Revenue Rocket world headquarters in Bloomington, Minnesota. With me today are my partners, Ryan Barnett and Matt Lockhart. Welcome, guys.
Matt:
Great to be here, Mike. Great to be here with you, Ryan. I’m excited about this. Ryan, what’s going on?
Ryan:
Each week, we cover what’s on the minds of IT services CEOs — and after more than 20 years in the market, we’ve learned a lot.
Today, we’re kicking off our new series: the Sell-Side Master Class for Tech Services Founders.
This series will walk you through what to consider before selling your firm — from understanding why you want to sell, to finding the right buyer, navigating diligence, and ultimately knowing when to let go.
By the end of the series, you’ll feel more confident about what it means to go through an M&A transaction as an IT services leader.
So let’s start with the biggest question founders face: How do you really know when it’s time to sell?
Selling isn’t quitting — it’s moving on to the next chapter for you and your firm. So Mike, why is that decision such a tough one for founders?
Mike:
It’s a huge decision. For most founders, their firm is their single largest asset. You’ve spent years — maybe decades — building something of real value.
There’s emotion, identity, and purpose tied into that.
When you start thinking about selling or recapitalizing, it can feel like you’re walking away from your life’s work. But it doesn’t have to be that way — you can design your exit to meet both your goals and your team’s goals.
It’s natural for this to feel big. My advice: get outside counsel early so you’re not making that decision in a vacuum.
Ryan:
Exactly. For CEOs, the firm is personal. You’re asking, Is this right for me, my employees, my customers? You fear regret — either for selling too soon or holding on too long.
It’s also hard to picture yourself having a “boss” for the first time. Even if your clients are technically your boss today, the idea of new ownership can be uncomfortable.
Matt, when founders start quietly wondering if it’s time — what are the early signals you see?
Matt:
The first sign is usually curiosity about valuation. They start asking, What’s my firm worth? and How attractive am I in today’s market?
Others feel stuck — like they’ve hit a growth barrier and can’t break through.
And then, sometimes, it’s simply time. They’ve been leading for 20 or 30 years and realize there’s more to life.
Those are all valid signals that it may be time to explore options.
Ryan:
That’s a great point. If you’re wearing every hat and feeling burned out, that’s a clear readiness signal. It might be time to take some chips off the table or become part of something bigger.
That brings us to two key paths: selling out or selling in.
Mike, what makes someone decide that “selling out” — fully moving on — is right?
Mike:
If you’ve lost passion for the business, or find yourself dreaming about other pursuits, that’s a sign.
If you’re burned out or hitting growth ceilings you can’t overcome, that’s another.
Age and life stage matter, too — maybe you want more time for family or new experiences.
At some point, it’s just time. Listen to yourself and your family. Those are all fair reasons to exit.
Ryan:
And that’s perfectly okay — selling out can be a healthy and positive next step.
But there’s another path: selling in, which means joining a larger platform and staying involved.
Matt, why do founders choose to sell in?
Matt:
Usually, it’s about acceleration. Selling in lets you scale faster with the help of a growth partner.
It also gives you a “second bite at the apple” — you de-risk by selling a majority stake but keep equity in the new, larger entity.
You also get to work with a higher caliber of peers and leadership — people who’ve done it before. That can reignite your energy and break you past growth barriers.
Ryan:
Exactly. It’s not binary — you can keep leading and still gain the benefits of a larger platform.
Let’s talk about a couple of “tests” that can help founders figure this out.
Mike, explain the Sunday Test — what does it mean if you wake up on Sunday excited or exhausted about the week ahead?
Mike:
It’s simple. If you dread Monday every week, that’s a red flag — you might be ready to sell out.
If you’re excited about the week and what’s ahead, that’s a sign you still have fuel in the tank — maybe a good fit for selling in.
Another is the time horizon test: if you want to be done within a year, that’s a sell-out mindset.
If you see yourself staying three to five years to grow value, that’s a sell-in mindset.
The gray zone — wanting out in two to three years — takes careful thought and deal structuring.
Ryan:
That’s a great way to look at it.
Matt, here’s another one — the Three-Year Test. Can you clearly picture your business three years from now being meaningfully stronger?
Matt:
That’s a confidence test.
If you can honestly say your foundation for scale — go-to-market, delivery, team, and positioning — is solid, that’s great. You might stay the course or find a partner to accelerate.
But if that vision feels cloudy or uncertain, it might be time to explore a sale. Sometimes “growing with someone else” is the right move.
Ryan:
Perfectly said. One last test: which decision would you regret more — selling or not selling?
If your biggest fear is missing out on something bigger, consider selling in.
If you’re burned out and ready for a clean slate, selling out might be right.
Mike, how important is alignment at home before making this decision?
Mike:
It’s critical. Your family has been through the ups and downs with you. They deserve a seat at the table.
Be transparent — share your thinking and timeline. These are life decisions, not just financial ones.
Having that clarity and support makes the transition much smoother.
Ryan:
Exactly. And Matt, let’s close with some low-stakes steps founders can take right now.
Matt:
Start small.
Get a valuation and see if it aligns with your personal “number.”
Do a readiness check — is your financial data clean? Are your contracts in order?
Identify your advisory team — legal, tax, and peers who can give you perspective.
These are low-commitment moves that prepare you whether you decide to sell or not.
Ryan:
That’s great advice. And that’s exactly what this Master Class series is about — helping founders think clearly about readiness before they jump in.
Mike, close us out.
Mike:
It takes a village to do this right — to decide when and how to sell, and to reach your number.
We’ve been doing this a long time and are always here to help founders navigate both the business and personal sides of M&A.
That wraps this week’s episode of Shoot the Moon.
Join us next time as we dive into the next step in the Master Class: Getting Your Business Ready to Sell.