I destroyed my best friend’s business… here’s what happened

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Eight years ago, I made one of the biggest mistakes in my entrepreneurial career:

I destroyed my best friend’s business.

And to this day, it remains the most painful failure I’ve ever experienced—not just because I tanked a company that wasn’t mine, but because of why it happened.

It wasn’t because of the market. It wasn’t bad luck. It wasn’t even poor execution.

It was me.

I went in cocky, riding the high of back-to-back business wins, thinking I had the golden touch.

Turns out.. I was wrong. Very wrong.

But failure is the best teacher in the world.

That is, if you learn from it the right lessons.

And right now, I find myself in yet another chaotic situation: one of my businesses is actively burning to the ground.

If you listen to my podcast, you already know. This is just part of the game.

In the game of entrepreneurship it’s not a matter of IF you’ll fail… only when.

And when those failures inevitably occur it’s imperative we take the time to unpack them so we can get the most value out of the tuition we’ve paid at the School of Hard Knocks.

So today, I want to share three brutal business lessons I learned the hard way, so you can get my lessons without the scars.

Let’s get into it.

1. The Closed Mind Doesn’t Grow

When I stepped into my friend’s business, I thought I knew everything.

I had just come off a streak of two successful ventures, and honestly, I got lucky….

Right product, right time, right mentors.

Things took off, and it felt easy. Easier than it should have been.

But that luck bred overconfidence.

I walked into my friend’s struggling company like a hero riding in to save the day.

I told him, “Don’t worry. I’ve got this.”

I believed it.

And in doing so, I built a prison around myself… one where I convinced myself I was supposed to be the one that had all the answers.

But I didn’t.

And as soon as I hit walls in areas of the business I had no experience in, I did what every prideful, inexperienced entrepreneur does…

I pushed harder, blindly. I didn’t ask questions. I didn’t seek help.

I thought asking for help would expose me as a fraud.

I thought needing guidance would shatter the image of competence I had built for myself and my friend.

And that became my first brutal lesson:

The closed mind doesn’t grow.

Because when you believe you know everything, you stop learning. You stop growing. You stop asking questions that could actually save you.

And the parts of the business you don’t understand?

Well, they are the ones that will eventually sink you.

Business is brutal like that.

Your weakest points are always where the cracks form.

And if your ego prevents you from filling those gaps, those cracks quickly turn into gaping chasms..

See, this is what I missed back then: Business is the ultimate personal development vehicle.

Business is the systematic process of revealing your own inadequacies.

It will never outgrow YOU, your skills, your resources, your beliefs.

And that’s why business is the ultimate vehicle for personal development.

That was a gut punch I didn’t see coming.

So, here’s what I know now:

You need to approach business like a student, not a savior.

You need to ask the dumb questions.

You need to be brutally honest about what you don’t know.

Because pretending you have all the answers might work for a minute, but it’s just a matter of time until it all comes crashing down.

Trust me, I learned that the hard way.

2. Pride is a Self-Imposed Prison

Looking back, the most dangerous thing I carried into my friend’s business wasn’t my lack of experience…

It was my ego.

Early success, it turns out, can be quite dangerous ‘cause it can easily lead you to overestimating your own abilities.

You tell yourself you’re different. Smarter. More driven. Somehow you’ve cracked the code on your first or second try.

And when others struggle, you assume it’s because they just don’t get it. They don’t have what you have.

That was me.

So, when things started falling apart, I didn’t see a problem to solve, I saw a threat to my identity.

My self-worth had become entangled with being the guy who had the answers. The fixer. The one who didn’t need help.

Admitting I was out of my depth felt like admitting I was a fraud.

Like maybe those first few wins were just luck, and maybe I wasn’t actually that special after all.

And that terrified me.

So instead of raising my hand and asking for help, I doubled down. I worked harder. I isolated myself.

I took on more and more, trying to prove (to myself, more than anyone) that I could do it alone.

But the harder I gripped, the faster things slipped through my fingers.

I was burning myself out, making bad decisions, and alienating the very people who could have supported me.

That’s what pride does.

It doesn’t just blind you…it chains you.

You build this version of yourself in your mind, and suddenly, protecting that version becomes more important than actually succeeding.

You trap yourself in an exhausting cycle of overcompensation and underperformance.

And here’s the brutal truth:

The people who win long-term are the ones who don’t care if they look stupid along the way.

They ask the dumb questions.
They admit when they don’t know.
They surround themselves with people smarter than them.

They seek help…early and often.

They prioritize progress over pride.

I didn’t. And it cost me.

So, whatever you’re building right now, I challenge you to ask yourself:

• Where is your pride keeping you small?
• What help are you resisting because you’re scared it might make you look weak?
• What belief about yourself are you protecting at the expense of actually winning?

3. Expectations Are the Root of All Discontent

If there was one thing that turned this tough situation into an unbearable one, it was this:

I expected it to go my way.

I stepped into my friend’s business thinking I could fix it. I thought my prior success was proof that I was capable, that if I just worked hard enough, pushed hard enough, this thing would turn around.

I expected that my effort would guarantee a result.

But business doesn’t work that way. Life doesn’t work that way.

Reality doesn’t care about your expectations.

It just is what it is.

And that delta between what you expect and what actually happens, well that’s the birthplace of frustration, of stress, of burnout.

I remember the day it all collapsed. I was exhausted, mentally fried, emotionally wrecked.

And beyond the pain of failure itself, what made it ten times worse was that I couldn’t reconcile it with what I thought was supposed to have happened.

I thought I was supposed to win.

But I lost.

And it wrecked me because I was still living in a reality that existed only in my head.

Expectations are dangerous little things.

We set them for ourselves, for others, for our businesses.

We tell ourselves that if we just do X, then Y will happen.

• If I work hard, I’ll succeed.
• If I hire this person, they’ll solve all my problems.
• If I launch this product, it will take off.

And then, to make things worse, we link our future happiness to achieving the result.
​
​If I work hard, I’ll succeed, and then I’ll be happy.

We create this illusion of control over outcomes we can never actually control.

So when reality doesn’t match up, we spiral. We cling to our expectations instead of adapting to the truth in front of us.

And that clinging? That’s what breaks us.

What I learned (the hard way) is this: You can work your ass off. You can make every right move. And you can still lose.

Because effort is not a contract with the universe.

The only thing you control is your input. Your output—the result—that’s up to a million other variables.

So the goal?

Let go of the expectation that success is owed to you.

Detach from outcomes. Fall in love with the process.

Focus on what you can control: your work ethic, your curiosity, your resilience.

Because when you do that, you free yourself from the constant cycle of frustration and disappointment.

You stop riding the emotional rollercoaster of wins and losses.

You find peace in the work itself.

And ironically, that’s when you start winning more often anyhow.

Stay Hyperfocused, My Friend…
Anthony Vicino

P.S. If you’ve got a business doing between 6 and 7 figures and you want my personal help making the jump to the next level, click here to apply for the Apex Accelerator.

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