Those Who Can’t Teach?
A young entrepreneur asked me the question most people are too polite to ask. I respected the hell out of him for it.
I got asked one of the best questions I’ve been asked in a long time.
It came from a young entrepreneur. Smart guy. Hungry. Curious. Trying to build something real. We were having a conversation about business, sales, the technology channel, consulting, courses, coaching, and all the stuff people love to package up and sell once they’ve had some level of success.
Then he asked me, respectfully but directly, the question a lot of people probably think but never say out loud.
If you were so successful doing it, why aren’t you still doing it?
That is a damn good question.
Because every consultant says they were successful. Every coach has a story. Every course creator has a bio that makes them sound like they walked down from Mount Sales with stone tablets and a CRM strategy. Everybody has screenshots, testimonials, vague revenue claims, and some version of “I built multiple seven-figure businesses.”
And let’s keep it honest. A lot of them weren’t that successful. Or they weren’t as successful as they make themselves out to be. Or they had one good run, in one good market, at one good time, and now they’re teaching theory like it’s gospel.
That’s why the old saying hits so hard.
Those who can’t, teach.
I understand why people say it. I’ve seen enough of the coaching world, consulting world, sales training world, and online course world to know there is a lot of truth hiding inside that insult. There are people teaching things they’ve never really built. There are people selling strategy who have never had to make payroll. There are people telling entrepreneurs how to scale when they have never had to look an employee in the eye and tell them the business is changing, the money is tight, and the future is uncertain.
That’s not me.
I don’t teach because I couldn’t do. I teach because I did. I teach because I paid for the lessons in money, stress, sleepless nights, mistakes, wins, losses, ego, humility, and survival. I teach because I know what it feels like to build something from scratch, watch it grow, carry people with you, and then have the game change in ways that force you to become someone new.
I started my sales career in jewelry. Before that, I was a kid knocking on doors and speaking publicly before I even really understood what communication was teaching me. Sales, persuasion, storytelling, reading people, building trust — those things have been part of my life for as long as I can remember.
I got into technology in 2001 and started my first real company in 2004. It was a technology sales agency. Not an insurance agency. Not a marketing agency. Not real estate. A technology sales agency. We sold B2B technology, network access, and services in the channel long before the channel became the crowded, overcomplicated ecosystem it is today.
And we built something real.
At our largest, we had three offices and more than 50 employees. We had salespeople, project management, customer service, operations, process, structure, systems, and customers. We weren’t just a person with a book of business and a cell phone. We were building an actual business.
Were we perfect? Hell no.
Would I build it the exact same way today? Absolutely not.
That’s the point.
Experience is not just what you did right. Experience is also knowing what you would never do again.
At one point, I was on top of the world. At least that’s how it felt. We had built a machine. We had sold thousands and thousands of customers. We had credibility. We had momentum. We had people depending on us. We were respected in our lane.
Then the business model shifted. The economics changed. The things that made us successful also made us vulnerable. We were too tied to one major partner. Too much of the business depended on a model I did not control. Too much overhead was attached to revenue that could be disrupted by decisions made in rooms I wasn’t invited into.
That’s one of the hardest lessons in business.
You can be successful and still be exposed.
You can be smart and still be vulnerable.
You can be winning and still be one structural change away from getting punched in the mouth.
And I got punched in the mouth.
Hard.
I had to make decisions I wouldn’t wish on any entrepreneur. I had to deal with the emotional weight of employees, families, obligations, contracts, debt, loyalty, pride, and disappointment. I had to accept that the thing I built was not going to continue in the same form. That kind of experience doesn’t show up in a LinkedIn bio, but it changes you.
It changed me.
I did not walk away because I failed and needed something easier. I shifted because I had learned too much to keep repeating the same model. I shifted because I could see the industry changing. I shifted because I knew the biggest gap in the technology channel was not access to products. It was education, structure, business acumen, sales process, and leadership.
So I built around that.
I started consulting. I coached. I trained. I created frameworks. I built courses. I licensed content. I worked with suppliers, TSDs, sales teams, channel leaders, and entrepreneurs. I helped other people build better sales motions, better partner strategies, better go-to-market plans, and better businesses.
That is not me being out of the game.
That is me playing a different position.
And let’s be clear, I am still in the game. I still build businesses. I still build brands. I still create sales processes for clients and for myself. I still launch offers, test messaging, structure partnerships, negotiate deals, create content, sell, consult, speak, train, and build.
Business & Bourbon was built from scratch.
SayLess Academy was built from scratch.
My consulting business was built from scratch.
My personal brand was built from scratch.
The courses, the events, the media, the partnerships, the frameworks, the content, the communities — none of that was handed to me. None of that came from theory. It came from doing the work.
That is why I take teaching seriously.
Teaching is not a consolation prize for me. Teaching is an extension of my purpose. It is how I turn scars into strategy. It is how I help the next entrepreneur avoid some of the landmines I stepped on. It is how I help salespeople stop wasting years chasing bad advice from people who don’t understand the actual business they are in.
The best teachers are not the people who read the most books or make the prettiest slides. The best teachers are the ones who have lived the lesson deeply enough to simplify it for somebody else.
That’s credibility.
Not hype.
Not a rented lifestyle.
Not “I made millions” with no receipts, no context, and no real operating wisdom behind it.
Credibility is being able to say, “I know this because I built it. I know this because I broke it. I know this because I had to fix it. I know this because I’m still doing it.”
That young entrepreneur’s question reminded me why I share my story. Not because I need to defend myself. Not because I need everybody to understand every private detail of my journey. Some things don’t need to be public. Some things don’t need to become content. Some things are better left as lessons, not weapons.
But I do think people deserve to know who they are learning from.
If you are going to hire a coach, buy a course, follow a consultant, or take advice from someone telling you how to build, sell, lead, or scale, ask better questions.
What have they actually built?
What happened when things went wrong?
Are they still creating, selling, testing, and operating today?
Do they understand the current market, or are they teaching a version of success that only worked ten years ago?
Can they teach the lesson beyond the highlight reel?
Because those who can’t may teach.
But those who did, survived, evolved, and are still building?
Those are the ones you should probably listen to.
Use code SHITTY for 50% off
