Ken DeWitt's Blog Sign Up & Past Issues
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E-book: 7 Stages of Long-Term Wealth Building Through Business Ownership and Driving Enterprise Value
Fear of Loss Outweighs Desire for Gain 6.2.26
“What would the company have to look like for you to disappear for a month?”
I’ve asked that question dozens of times in EOS® sessions. It’s simple. Disarming. And it almost always creates a pause.
This time was no different. The Visionary business owner hesitated, looked down. Thought for a minute then he began to describe what that would require. Not in abstract terms—but in very real, very specific conditions.
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What Is Your "Work Language"? 5.19.26
Ever watch people work together who don’t speak the same language? It’s part charades, part jazz improvisation—and somehow… wildly effective.
Until someone assumes everyone else is hearing the same thing in their head.
In my work with leadership teams, I consistently find they’re unaware of what I call “The Four Work Languages.” Or maybe more accurately, dialects. There’s nothing official about this—just observations from more than 40 years of misinterpretation and miscommunication.
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My Life’s Wish at 27 5.5.25
There’s a question that can change your life.
Mine came over dinner… I was 27 years old… Engaged… Insecure… Trying to prove I belonged in rooms I didn’t feel qualified to enter.
I had started an accounting firm with my brother at 24. We were grinding. I hadn’t found my footing — or my identity.
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Investing in Training for a Scalable Company (Part 1 of 2) 3.31.26
Companies make cost/benefit decisions every day. Typically, it is fairly easy to do so on a key piece of equipment or perhaps a new building. You can model depreciation, capacity, and payback.
This is harder to do when the investment is people—especially when deciding whether to hire a new employee, or whether to invest in a leadership and management training like Entrepreneurial Operating System® (EOS®).
Many companies quickly see the benefits of investing in EOS training with a Professional EOS Implementer® during the first two years.
But once those foundational investments are complete, an important question emerges: Where should you turn your attention next to keep scaling—without losing what you built?..
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Investing in Training for a Scalable Company (Part 2 of 2) 4.7.26
In Part 1 I started to share ways to take EOS® deeper in a company. Even after scaling down your reliance on—and payments to—your EOS Implementer®.
Here are 5 MORE ways to do that, with a brief Cost/Benefit analysis for each.
No Mas. EOS Is Enough. 4.3.26
Adding more feels like progress, but it often reduces results. Here’s why EOS is enough and how you can protect your company’s focus...
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Three Big Lessons I’ve Learned in Business 3.17.26
I do a lot of podcasts, workshops, and other appearances these days. It’s fun, and it’s my way of giving back—because “help first” is one of my cherished core values.
I was on the Level 10 Leaders podcast with Ryan Castle recently, and he asked a deceptively simple question: “What are the top three lessons you’ve learned in 40+ years in business?”
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Why Am I So Scared? 2.17.26
Why am I so scared?
I’m talking about something unglamorous and deeply familiar: my struggle to have frank, candid conversations—with business partners, employees, contractors, customers, and even family.
If I’m honest, I’ve been lousy at this my whole life. I avoid these conversations. And that avoidance has cost me dearly.
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Is It Time to Recommit to Your EOS Journey? 2.13.26
Drifting from EOS fundamentals? Learn the hidden cost of losing traction and how to recommit and strengthen your business from top to bottom...
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EOS® Best Practices: Why Reviewing the Prior Quarter Is One of the Highest-Value Disciplines You’ll Ever Install 2.3.26
If you’ve worked with me for any amount of time, you’ve heard me say it: “EOS is a discipline system disguised as a business operating system.” And nothing proves that more clearly than the practice of reviewing the prior quarter.
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Work Really Is Like College Football — Except When It’s Not 1.20.26
Every Saturday in the fall, I live for College Football.
I throw on my team’s colors. Fire up the grill. Turn on College Gameday. I’ve been this way since I was ten – growing up here in Tuscaloosa. For me, college football isn’t just entertainment. It’s ritual. It’s rhythm. It’s us vs. them.
There are game plans, rivalries, upsets, Rudy-like walk-on stories, locker room speeches, and last-second field goals that haunt you for decades. And if you’ve ever sat in the stands for a night game at Bryant-Denny or Jordan-Hare in October, you know — it’s more than just a game.
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EOS® Companies and AI: Where We Are – January 2026 1.6.26
Let me start with a confession: I’m not the fastest adopter of new technology.
But entrepreneurs—especially those running on EOS—can no longer ignore this: AI is no longer “coming” ... it’s here. It’s showing up in your competitors’ workflows, bids, customer outreach, and internal systems. And unless your leadership team begins exploring how—and equally important, how not—to use it, you will be left behind.
My mantra lately?
“AI is not necessarily coming for your job (or your business). But people and companies who know how to use AI are coming for your job.”
So let's get curious, cautious, and competent about it—or watch our competitors eat our lunch.
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The Tortoise Wins: Building Wealth, the EOS Way 12.9.25
If you're tired of startup fairy tales and ready for something real, this is for you. After more than 40 years in business—as an owner, advisor, and for the last 14 years as a Professional EOS Implementer—I’ve learned this truth the hard way: “Let’s not let our lives serve our businesses. Let’s build businesses that serve our lives.”
That’s the heartbeat behind “The 7 Stages of Long-Term Wealth Building through Business Ownership”.
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Pre-Annual Planning Retreat Homework for V/I Duos 11.25.25
Every fall, thousands of Leadership Teams gather for their EOS® Annual Planning Sessions—two full days of clarity, connection, and commitment. But if you're the Visionary/Integrator (V/I) Duo at the top of the org chart, the real work starts well before that first whiteboard gets a mark.
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Breaking Through the “Layer of Clay”: What I Learned About How New Leaders Really Learn 11.11.25
We've been misunderstanding how new leaders actually learn - and it's costing us. In this blog, I unpack what Mike calls the "layer of clay" that keeps great ideas from taking root inside organizations, and how EOS leaders can help their teams grow through it.
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Why I Appear on The Noon Show 10.28.25
I've started regularly joining 𝘛𝘩𝘦 𝘕𝘰𝘰𝘯 𝘚𝘩𝘰𝘸 with Johnnie Aycock, CPC, IOM and Lisa Jones- to share what I've learned about entrepreneurs, leadership, and growth. It's one more way to 𝘩𝘦𝘭𝘱 𝘧𝘪𝘳𝘴𝘵, and support the business owners who keep our communities thriving. Read more about it below!
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Why Most SMBs Suck at Training — and How EOS® Companies Can Lead the Way 10.14.25
Let’s call it like it is: most small and mid-sized businesses suck at training. Not because they don’t care. Not because their people aren’t worth it. But because they’re stuck in a cycle of survival — and survival mode doesn’t design great systems for thriving.
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Why Choosing the Right EOS Implementer Matters 10.6.25
Not all EOS Implementers are created equal - and that’s a good thing! This blog breaks down why the right fit between an Implementer and a leadership team can make or break your journey to traction.
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A Seat Issue + Drama Triangle = Leadership Danger Zone 7.19.25
As EOS Implementers, we see this over and over again. A leadership team knows they have a Right Person/Right Seat (RP/RS) issue. They nod in agreement. They even score the People Analyzer honestly. Yet when it comes time to act, they hesitate...
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Long-Term Wealth Building Through Business Ownership and Driving Enterprise Value (BBJ) (Part 1) 5.5.25
It’s been said there are only four real ways to build wealth: inherit it, steal it, mine it or grow it through a business or career...
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Getting Control of Your Business: Building Long-Term Wealth Through Business Ownership (Part 2) 7.1.25
For the first 25 years I owned businesses, I was stuck in the same trap that catches so many entrepreneurs: I was working IN the business, not ON it...
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Evolving into a Visionary: Building Long-Term Wealth Through Business Ownership (Part 3) 7.15.25
You didn’t start a business just to own a job. You’re here to create wealth, impact, and freedom. And that begins with discovering your highest and best use in the business...
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Building a Leadership Team: Building Long-Term Wealth Through Business Ownership (Part 4) 7.29.25
Most leaders I coach wrestle with who should (and should not) be on the Leadership Team. There’s fear of hurting feelings—but remember, it’s easier to invite someone in later than to uninvite them...
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Driving Enterprise Value: Building Long-Term Wealth Through Business Ownership (Part 5) 8.12.25
Reinvesting profits is common. But if you’re not doing so with strategic intent to increase enterprise value, your efforts may be misdirected or ineffective. True value comes from the ability to generate consistent profits and cash flow without daily owner involvement...
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Harvest Wealth: Building Long-Term Wealth Through Business Ownership (Part 6) 8.26.25
Let’s talk about getting the money out of your business — and into your pocket — to create lasting financial freedom.
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Get on the Same Page with Spouse/Significant Other: Building Long-Term Wealth Through Business Ownership (Part 7) 9.9.25
Now that we've seen how to build and protect wealth through business ownership, it's time for the most critical stage—enjoying the wealth, keeping it to build financial independence, and, frankly, avoiding a big fight over money at home.
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Shine Brighter, Lead with Peace 9.23.25
An introduction to Shine by Gino Wickman, including the "10 Disciplines of The EOS Life"
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Storming the Beaches Within: A Lesson from Normandy 6.17.25
After 49 years of life together—raising a family, building a business, chasing dreams—Pam and I finally took a vacation unlike any we’d had before. A cruise from Lisbon to London, weaving through Portugal, Spain, France, and the Channel Islands. It was overdue. And unexpected in what it gave back...
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The Advantages of using Software to run your EOS 4.24.25
Back in 1981, as a senior in college, I landed my first “real” job—with Saturdays off. For the first time in my life, I could actually attend Alabama Crimson Tide games like a proper fan. It felt like I’d made it...
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The Sergeant Major: Enforcing Discipline in EOS Meetings 4.18.25
Mom was the Sergeant Major in our family. Vera Mary Cason DeWitt. Dad was out and about running three small businesses, and Mom worked at home raising eight kids. They both were stateside Staff Sergeants in the Army...
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Thoughts After 1,000 Sessions 3.19.25
In my second career, I've finally found abundance.
For the first 30 years, I lived in a world of scarcity.
The last 10 have been the best of my life, and I now wake every day with a sense of gratitude and excitement for the coming day, weeks and years that I may have left on this planet.
What I’ve learned will not take you 30 years to figure out...
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What does it mean to lead a life of Significance and Impact? 3.12.25
Recently, I asked that question of about 20 business people gathered at the John Hand Club in Birmingham.
We’d come together for a “Fall Party,” and these were people I’d served over the last dozen or so years in my second career. All are now my friends...
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Do You Know Your Purpose Here? 2.27.25
Ever stopped to ask yourself why you're here? What your real purpose is?
As business owners, we live fast-paced, chaotic lives. We juggle family, friendships, community responsibilities—on top of customers, employees, vendors, financial pressures, competition, and an ever-changing economy. It’s a lot.
For me, the key to staying grounded is remembering what truly matters...
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Ken DeWitt
Ken is an Expert EOS Implementer. He has worked with 100+ companies in 1000+ sessions to help entrepreneurs and their leadership teams solve root problems, lead more effectively, and gain Traction® in their businesses through a simple, proven operating system.