From Sales to Strategy: Ryan Mitchell on Helping Small Business Owners Find the Right Path
Small business ownership comes with plenty of challenges, but few are as important as understanding where you want the business to go—and then building a plan to get there.
On this episode of the Grit Won’t Quit Podcast, Tom sits down with Ryan Mitchell of CPR Tax to talk about Ryan’s journey from insurance and outside sales into tax and accounting, his work with small business owners, and the importance of understanding what clients actually need.
Finding the Real Problem Behind the Problem
Ryan’s entrepreneurial journey began in insurance before he moved into outside sales. Through that experience, he noticed a common problem among the small business owners he worked with: they needed help with their accounting, but their bigger concern was often their fear of the IRS.
That realization led Ryan into the tax and accounting world, where his goal became more than simply preparing returns or maintaining books. He wanted to help business owners understand their numbers, reduce uncertainty, and address the risks that could affect their businesses.
Today, Ryan has expanded his focus to include insurance as well, recognizing that financial planning and risk management are closely connected.
Start With the Desired Outcome
One of the biggest themes throughout the conversation is the importance of starting with the end goal.
Before deciding what accounting strategy, insurance coverage, or business structure makes sense, Ryan believes you first have to understand who the client is and what they are actually trying to accomplish.
Once the desired outcome is clear, the strategy can be built around it.
That might mean evaluating insurance needs, considering a buy-sell agreement, improving accounting practices, or identifying financial decisions that could create unnecessary risk.
The key is that the plan should fit the business owner—not the other way around.
Small Business Owners Have to Work On the Business, Not Just In It
For many entrepreneurs, working in the business comes naturally. They’re serving customers, completing jobs, managing employees, answering calls, and handling the daily responsibilities that keep everything moving.
Working on the business is different.
It requires stepping back and asking bigger questions:
Where is the business going?
Are the goals realistic?
What needs to change to reach those goals?
Are current systems supporting growth?
What risks could prevent the business from getting there?
As Tom and Ryan discuss, most people don’t start a business because they want to manage employees, build systems, or spend their days making strategic decisions. They start because they want independence and the opportunity to do something they care about.
But as the business grows, the job changes.
Growth Changes the Game
A business with one employee and a business with 30 employees are fundamentally different responsibilities.
With growth comes more people depending on the business, more customers, more expenses, more decisions, and more opportunities for a small mistake to become a much bigger problem.
Tom and Ryan discuss how one poor decision—whether it’s an insurance gap, a bad real estate commitment, or an expensive operational change—can create a domino effect throughout a growing company.
The bigger the organization becomes, the more important thoughtful decision-making becomes.
A decision that costs a small business $1,000 or $2,000 might become an $80,000 problem at a larger scale.
Getting Comfortable Being Uncomfortable
Another major theme of the episode is the willingness to step outside your comfort zone.
For Ryan, that has included getting on video, marketing himself, and putting his personality in front of potential clients.
It’s uncomfortable for many business owners, but customers increasingly want to know the person behind the business.
Authenticity matters because relationships matter.
Ryan talks about how his clients know his personality, his quirks, and even his imperfections. That familiarity can create trust because clients know they’re dealing with a real person rather than a polished corporate persona.
For business owners, being visible can be part of building the brand.
AI Can Help, But It Can’t Replace Authenticity
The conversation also explores how artificial intelligence is changing marketing, communication, and business operations.
AI can be extremely useful for repetitive tasks, organizing information, and improving efficiency. But Tom and Ryan question what happens when businesses rely on technology so heavily that the human element disappears.
If every social post looks the same, every website feels generated, and every customer interaction comes through an automated funnel, businesses risk becoming interchangeable.
The distinction between AI and automation is important. Automation can streamline a workflow, but genuine human intelligence still requires curiosity, judgment, creativity, and critical thinking.
AI can help enhance someone’s ideas. It shouldn’t eliminate the thinking that produced those ideas in the first place.
The Importance of Doing the Work
One of the strongest points from the conversation is that shortcuts don’t eliminate the need for effort.
Whether it’s building a business, training for a marathon, improving a marketing strategy, or developing expertise, the visible result is only the end of a much longer process.
Ryan compares this to running. The marathon itself isn’t the work. The hundreds of miles of training that lead up to it are the work.
Business works the same way.
The sale isn’t necessarily the work. The job isn’t necessarily the work. Building the systems, relationships, knowledge, reputation, and consistency that make those results possible is the work.
AI may make some tasks faster, but the people who continue investing time into learning and improving can use that technology as an advantage rather than simply as a shortcut.
Curiosity Is a Business Skill
Curiosity is another recurring idea throughout the episode.
Instead of simply accepting a result, curious business owners ask what caused it and what they can learn from it.
Where did a lead come from?
What search produced it?
Which marketing channel generated the customer?
What information does an AI platform use to understand the business?
What could be improved?
That mindset creates opportunities to keep refining the business rather than simply repeating what has always been done.
Sometimes Low Tech Works Just Fine
Not every successful business needs to be highly automated or technologically sophisticated.
Tom and Ryan talk about tradespeople and contractors who operate with simple systems—a phone, a clipboard, a truck, and a strong network of customers—while still building successful businesses.
The lesson isn’t that technology is unnecessary. It’s that technology should serve the desired outcome.
If a simple process works and produces the result the owner wants, there may be no reason to complicate it.
Making Decisions With the Bigger Picture in Mind
As a business grows, decisions affect more than the owner.
Employees and their families, customers, vendors, and other stakeholders can all be affected by major business decisions.
That makes it increasingly important for owners to think beyond the immediate result.
Is this decision aligned with the company’s goals?
Does it create unnecessary risk?
Can the business absorb the downside if things don’t go according to plan?
Is the decision being made intentionally, or is the business simply reacting to the latest problem?
Those questions can help business owners stay focused on the bigger picture.
Building a Business Around the Life You Actually Want
Ultimately, the conversation comes back to the idea of outcomes.
There isn’t one universal definition of a successful business.
For one owner, it might mean building a large company and creating jobs. For another, it might mean a small, profitable operation that provides independence and flexibility.
The right strategy depends on what the owner actually wants.
Understanding that goal first can help determine everything that follows—from technology and marketing to accounting, insurance, staffing, and growth.
Ryan’s conversation with Tom is a reminder that building a business isn’t simply about working harder. It’s about understanding where you’re trying to go, making intentional decisions, managing risk, staying authentic, and putting in the work required to get there.
Learn More
To learn more about Ryan Mitchell and CPR Tax, visit CPR.Tax.
You can also learn more about Ryan’s work, entrepreneurship, taxes, food, and running at TaxmanWhoEats.com.
This podcast episode was filmed at Wingman Planning in Belmar.
