Too many business owners wait too long to raise their prices.
They think it’s about timing. Or loyalty. Or not wanting to rock the boat.
But it usually comes down to one thing: fear.
At the main stage at ProfitCON hosted by Profit First Professionals, the organization behind the Profit First methodology, Arron Bennett, CEO of Bennett Financials, broke down exactly how that fear shows up, and how to move through it without putting your business at risk. He wasn’t giving hypotheticals. He explained how to restructure pricing in a way that aligns with margin, delivery, and long-term scale.
“It’s going to feel uncomfortable when you first go out there and say, like, say if you’re $1,000—you raise your prices double, and it’s like now $2,000—it’s like, oh, that is scary at the very beginning. But it gets easier over time.”
Arron Bennett at ProfitCON 2024
Most businesses don’t need more volume. They need better structure. If your pricing model doesn’t support your actual costs, capacity, or value, you’re not just leaving money on the table—you’re building on a shaky foundation.
Arron shared exactly how his own firm handled the shift.
“Just keep bringing those new people in and raising the prices… It is a slower process. I’m like, all right, $2,000 comes in, let’s do two clients and see what happens. And then we just keep inching it along until you’ve rinsed your whole client space.”
Arron Bennett at ProfitCON 2024
This is strategic finance in action: adjusting how revenue is generated, not just how expenses are tracked. It’s what allows a business to scale without burning out the team or blowing up cash flow.
That method—gradual replacement of underpriced clients—works. And once you make it through the first cycle, the next one gets easier.
“Then what’s going to happen is you’re going to get to the end, and then you’ll be like, I need to raise my prices again. Do it again. Keep doing it.”
Arron Bennett at ProfitCON 2024
The goal isn’t just to charge more. It’s to build a system that supports higher-value delivery, stronger margins, and sustainable growth. That starts with a financial model that ties pricing, compensation, tax planning, and cash flow together.
That’s what strategic finance does. It gives you the clarity and structure to make confident pricing decisions — and the visibility to know when it’s time to adjust again.
If your margins are tight and pricing hasn’t been touched in a while, now is the time to take a hard look at how your numbers support the business you’re trying to run.
This is the kind of work we do every day with our clients.
Explore Strategic Finance to see how pricing, profit, and planning all connect or reach out to optimize your pricing.
Original clip from Arron’s main stage on YouTube:
Interested in learning more about Profit First? Read Chapter 1 of our ebook, Profit First, Unofficial: A CFO’s Playbook for Owners.