An exclusive community and data backed acquisition system to buy your first or your next business and build a lasting legacy.
You're not stuck, you're just alone at the top. Most entrepreneurs hit a ceiling, not because the opportunity isn't there, but because you're solving $10M problems with $1M strategies.
Unsure where to start?
Try our concierge
Welcome to The Main Street Minute, your shortcut to small business buying and scaling.
👋 Huge shout-out to the new readers who joined the newsletter last week.
Reminder: When you’re ready to get to work, we designed these tools just for you…
Now, onto today’s story.
START HERE
Most people think accounting is boring. Kelly Bender thinks that’s perfect.
Kelly has been advising small business owners for 15 years, building an accounting firm around serving what she calls “the quiet everyday millionaire next door.”
In 2018, she noticed something:
“It felt like everybody around us in the accounting space was retiring or dying.”
But rather than wait for the ground to shift under her, Kelly saw it as an opportunity.
She started buying firms. Some smaller ones. Then bigger ones.
Five acquisitions later, she’s built a 19-person, multi-location, $2.5M firm with a path to break $3M soon. But scaling there wasn’t linear. Kelly has hit hurdles in hiring, operations, and dealmaking.
This is the story of how she pushed through those hurdles, survived a 6-figure loss, and used 1 key operational shift to hire effectively in one of the hardest labor markets in America.
Lots of lessons you can steal below…
THE PROBLEM
If you want to know where future fortunes will be made, don’t look at markets; look at rooms.
Why? Wealth follows proximity. The closer you are to capital, information, and ambition, the higher your expected return.
Presence is an asset. Yield is measured in things like better relationships, asymmetric insight, and time saved. Like any asset, the earlier you invest, the greater your potential to compound.
Economists call it agglomeration, the phenomenon where productivity and innovation rise as people and ideas cluster together.
By the time Kelly joined our programs, she already had a relatively established firm and a clear operational base, with acquisitions ranging from just $35k to about $750k.
Each deal taught her something different:
But over time, she also learned that she felt something else: isolation.
She wasn’t surrounded by many people who understood the problems she was facing and who knew what buying and integrating firms really felt like on a day-to-day basis…
Inside our Growth Boardroom, she found operators who had already solved or experienced the problems she was wrestling with:
That proximity changed how she thought about acquisitions mechanically.
“I didn’t quite understand that I’d be able to bolt a larger acquisition into what I already have… That confidence came from learning that what I had in place was actually pretty good.”
Larger acquisitions… Building an empire… These didn’t feel like a stretch anymore. They felt within reach.
PATH TO SCALE
Nearly everyone in business will tell you that you’ll eventually get burned. The real skill is knowing how to recover, learn from it, and keep on moving.
One of Kelly’s biggest acquisition setbacks happened early this year.
Issues with a dishonest seller surfaced after closing, and Kelly ended up having to absorb a six-figure loss. “It was gut-punching,” as she put it.
Most owners would have spiraled or lawyered up for 2 years pursuing the seller legally, costing tens of thousands in attorney fees, and destroying their focus.
Not Kelly.
“I suffered a loss for being naive and trusting someone who was less than honest. Being in a room with other owners who were like, ‘Yeah, I know exactly what that feels like. It sucks. You’re going to have to move on and here’s how.’ That bluntness was really helpful.”
Not dismissive. Experienced. This moment didn’t just help her process the loss. It helped her develop as an owner.
As Kelly said, “That’s what the evolution to being a more seasoned entrepreneur will do to you. Some people think that when you buy businesses, it’s all sunshine and roses, but obviously, it’s not. It’s hard, and sometimes you have less-than-ideal individuals who do you wrong.”
GROWTH LEVER
Sometimes, scaling isn’t a growth problem, but rather a talent problem. And after 5 acquisitions, one of Kelly’s biggest constraints was hiring.
“We have a really hard time hiring in our industry… Nobody wants to be an accountant.”
She is not wrong… Accounting grads are in serious decline:
Her firm had systems. It had clients. It had referrals. What it didn’t have was a reliable way to turn a new potential hire into a high-performing, long-term team member.
That changed after she took the time to work with us to seriously develop her employees’ first 100-day talent plans.
“We had something okay, but we implemented it a lot better after that.”
She rebuilt her employee onboarding from the ground up. Clear expectations. Structured ramp-up. Weekly check-ins. Skill benchmarks. The results were rapid and measurable:
In an industry battling a historic shortage of talent, this was a breakthrough.
KEY RESULTS
Kelly is unapologetically Main Street. She believes small businesses should employ people in their own communities more often.
“If we’re really going to change Main Street, we have to be committed to employing people inside our community.”
Despite immense pressure in accounting to offshore work, she refuses. She’s also honest about what happens when culture is ignored and is blunt about what she sees private equity doing in her space:
“Private equity has essentially come in and stripped the culture of Main Street America out of our communities by only focusing on capital. You can be a capitalist and still care about employing people inside of our communities.”
While not everyone might agree on the approach (even we have some offshore team members), Kelly believes Main Street businesses should be staffed locally because of the flywheel it can create:
She’s not naive about the pressure and benefits of outsourcing. She also believes strongly in leveraging technology to operate and grow efficiently.
But she also believes that culture scales reputation, and reputation builds a more durable SMB accounting firm in the long run.
THE FUTURE
Kelly wanted to solve problems faster and with other builders.
She now calls up peers in our Boardroom to reality-check acquisitions.
She speaks to our in-house sales experts to develop her outbound strategy (after growing 15 years purely by referrals).
And she helps other members evaluate their potential deals using her own experience.
Your best solutions rarely come from inside your own 4 walls. They come from people who’ve already survived the problem you’re facing.
As for what’s next?
Bigger Deals. Better Systems. More Stability.
Kelly is now evaluating multi-million-dollar deals, the kind she once assumed were out of reach and might never have considered before improving her systems and joining the right room.
“There’s plenty of room for all of us… If you go out on your own, I hope you win.”
Want to join thousands of smart business builders and buyers?
Get access to our live expert calls (and so much more) when you join our Contrarian Academy or Growth Boardroom.
The information contained here is educational, may not be typical, and does not guarantee returns. Background, education, effort, and application will affect your experience and the profitability of any business. Individual results may vary.
.svg)
