Reinvest 10% in Yourself: The Antidote to Business Fear

In this episode of the Measure Success Podcast, I sat down with Tommy Breedlove, Wall Street Journal and USA Today bestselling author of Legendary and founder of Legendary, a success accelerator for high-achieving leaders and entrepreneurs, to talk about what's driving fear among business owners right now, why AI can't replace real accounting judgment, and why reinvesting in yourself might be the best hedge against an uncertain future. Tommy began his career at Deloitte and rose to Shareholder, International Practice Leader, and Board Member at one of the Southeast's largest financial firms before building a coaching practice for nine-figure entrepreneurs and executives.

Why Successful People Are Still Afraid

Tommy works mostly with entrepreneurs and business leaders, including several worth nine figures personally.

Even at that level, the fear doesn't go away. It just changes shape.

He shared the story of a client who predicted, three years out, that his fifteen-million-dollar company would shrink to seven and a half million if he didn't change course.

He saw it coming. He didn't act.

"Guess what happened this year? He lost half, seven point five million in one year."

The lesson: knowing what's coming isn't the same as doing something about it.

Reinvest 10% in Yourself

Carl brought up a principle he credits back to Zig Ziglar and Darren Hardy:

Reinvest about 10% of your revenue into yourself and your business every year.

Tommy agreed it's non-negotiable, especially with how fast the market is changing.

• Skills, tools, and coaching compound over time • Standing still isn't neutral, it's falling behind • The businesses that keep investing are the ones still standing when others capitulate

AI Still Gets the Basics Wrong

Carl shared a moment that reframed how he thinks about AI in his CPA practice.

He ran part of a client's strategy document through AI to save time. The client noticed immediately.

"I hired you for your 30 years of experience. I did not hire you for AI."

Tommy backed it up with his own story: his team member Erica ran his writing through an AI tool overnight, and it came back as "garbage" and "slop."

• AI still gets basic debits and credits wrong • Small business accounting is messy, and AI alone won't fix it • The real value is curating what AI produces and communicating it in human terms

"If you know what AI looks like, you can't unsee it."

Private Equity Is Coming for CPA Firms

Carl pointed out that over 70% of CPA firms are run by people at or past retirement age.

Many are coasting, unwilling to take new clients, and selling to private equity as fast as they can.

Tommy didn't hold back on what that means:

"They're just not good at a lot of things, but they're very good at making numbers up, and making money until they don't make money."

He compared it to a debt stack that eventually has to be paid, calling it "the next internet bubble."

From 2 to 10: Building Without a Partnership Structure

Carl shared that his own CPA firm grew from 2 employees to 10 in a single year, a 5X jump.

He built it deliberately without a traditional partnership structure, which lets him avoid the retirement obligations and pricing pressure many legacy firms face.

That structure is part of why he can keep investing instead of raising prices as AI pushes costs down across the industry.

Why We're Both Building ESOPs Instead of Selling

Both Carl and Tommy said they have zero intention of selling their companies to private equity.

Instead, both are building toward an Employee Stock Ownership Plan (ESOP), so the team benefits long-term instead of a single payout going to the founder.

Tommy shared that his team member Erica, the last original employee at his company, has two years of salary guaranteed if anything happens to him. He's actively developing her to become a stronger speaker and leader than he is.

"I want to leave something bigger than me. I want to leave a legacy."

The Data on Retirement Without Purpose

Tommy shared data from his own research after selling businesses without a follow-up purpose:

People are up to 80% more likely within a year to be on a new prescription medication after they retire or sell without a plan for what comes next.

His speech on the topic became the highest-rated keynote at a major conference he spoke at, specifically because he was honest and vulnerable about what happens to "doers" and "builders" after the transaction.

"Plan for the human and the leader who was a doer, who was a maker, who was a builder, after the transaction."

Master Your Mindset

Tommy's core belief: success starts with the mind and heart, not tactics.

"It is a master your mindset. It is constant development of your heart muscle and your mind muscle."

He's currently rereading The Millionaire Mindset, The Road Less Stupid, and A Pocket Full of Money, and plans to work through Think and Grow Rich with his executive team for the sixth or seventh time.

• Eliminate people and noise that drag you down • Don't let mediocrity or naysayers into your circle • Treat mental and emotional strength like a muscle that needs constant training

Forgiveness

The conversation closed on an unexpectedly personal note.

Tommy shared that he hadn't left things right with his wife, Heather, that morning, and apologized to her live on the call.

Both hosts connected that moment to a bigger theme: forgiveness as a business and life skill, not just a personal one.

"When you can forgive and feel like you've been forgiven, it's the most powerful thing in the world for you to have the freedom to move forward."

Forgiveness is one of the core sections at Tommy's Legendary Retreat in the Appalachian Mountains, alongside the harder skills of strategy and scale.

Final Thoughts

This episode covered a lot of ground: fear, AI, private equity, ESOPs, mindset, and forgiveness.

But the through-line was simple.

The businesses and people who keep reinvesting in themselves, stay honest about what AI can't do, and hold onto purpose beyond the transaction are the ones who come out ahead.

Listen to the full episode and ask yourself:

What would change if you stopped waiting for permission to reinvest in yourself?