Some businesses scale effortlessly. Others struggle, stall, or collapse under their own weight.
The difference? It’s not intelligence, luck, or even resources. It comes down to one simple rule—a rule that championship sports teams, billion-dollar companies, and elite entrepreneurs all understand.
Most people ignore it. And it costs them millions.
I break it down in my latest article.
Would you let $235 a month cost you millions?
Sounds ridiculous, right? But I’ve seen business owners sabotage multi-million dollar deals just to save a few bucks on proper bookkeeping and financial reporting.
One refused to upgrade her accountant—her deal fell apart in due diligence. Another wasted hours in Excel hell instead of growing his business.
The #1 deal killer? Poorly done financial records.
Don’t be the Black Knight hacking away with no arms
Jay was leading an M&A team set to close a major acquisition the next day.
That night, they took the seller out for a celebratory dinner. Drinks were flowing, and the owner had too much.
As they were leaving, things turned awkward. The seller got aggressive with the staff, grabbed his car keys, and drove off.
The next morning?
The deal was dead
Last night, I had a simple goal: clear out an old room and get rid of a bed in excellent condition that had been sitting in storage for three years.
What should’ve been an easy giveaway turned into something much more interesting.
It made me rethink the difference between transactions and relationships… short-term cash and long-term value.
And how these same principles shape the businesses that truly thrive.
Is your business less independent than my 3 and 5-year-olds?
Next week, I’m flying to Greece for my father’s funeral. It’ll be the first time in five years that I won’t be sleeping under the same roof as my daughters.
They’re 5 and 3 now—not old enough to take the keys, but they’ll manage just fine. My wife has it all under control.
It made me think, though… How many business owners can say the same about their companies?
If you step away for a week, does everything fall apart?
Sure, your business might pay the bills, but that’s not freedom. That’s a trap.
There’s a playbook for building a business that works without you—one that frees your time, reduces stress, and builds real value.
Have you started working on yours?
How a dream gave me the peace to handle the news I expected… and long feared coming…
There’s a thief in your business.
But this isn’t just someone stealing money. It’s much worse.
This thief is taking your time, your freedom, and your future… right under your nose. And the scariest part? You won’t believe who it is
Customers in. Customers out. Your business is running like a hamster wheel you can’t escape.
You’ve cut prices, offered discounts, and even slashed costs. But you’re still sprinting just to survive.
Why? Because there’s a Thief you haven’t seen yet. And he’s silently killing everything yo have been sacrificing and building…
This story might hit closer to home than you’d like
Imagine waking up to find out you’re being robbed.
Not just by anyone—but by someone you trust… every single day.
This isn’t just a story about theft. It’s about an invisible threat taking control of your life, your business, and your future.
The craziest part? You’re letting it happen.
Discover the truth before it’s too late.
What if the way you’re running your business is setting you up for failure?
Most business owners focus on one thing—more income. More sales, more cash flow, more profit. Sounds smart, right?
But there’s a silent killer lurking in that mindset… one that’s destroyed once-thriving businesses overnight.
I’ve seen it happen. You probably have, too.
The worst part? Most people don’t even realize they’re making this mistake.
Here’s what you need to know before it’s too late.
Ever feel like you’re stuck doing tasks that aren’t moving your business forward? At last night’s Happy Hour, one business owner shared with me after the event how he planned to reclaim 15 hours a week just by applying the key lessons on delegation we discussed. He realised those hours spent on emails, bookkeeping, and admin were costing him real opportunities—like landing high-value clients.
This morning, I came home to my dog losing her mind with excitement—running back and forth, grabbing her toy, acting like a puppy again.
Cute, right?
But here’s the thing: I stepped out again a couple of hours later…for one minute. And she did the exact same over-the-top welcome.
It got me thinking about business—and why being “more of the same” is the kiss of death.
In 1987, my football team won exactly one game.
Our coach thought positivity could save us. Spoiler: it didn’t.
So, what did a bunch of frustrated teenagers do? We turned our frustration in the wrong direction. Immature? Absolutely. But the lessons from that disaster of a season stuck with me for life.
Fast forward to 2025, and I’m sharing a very different kind of game plan for winning in business.
Aileen came to us stuck.
She needed to decide whether to invest in or divest one of her divisions—a decision worth millions.
In 60 minutes, she had her answer.
Not because I told her what to do. Not because I overwhelmed her with frameworks or formulas.
But because I guided her …..
Delegation isn’t about “letting go”—it’s about leading smarter. Yet so many business owners struggle to step away because their team just can’t handle the load.
Here’s the kicker: it’s not your team’s fault. It’s a skill you need to master.
Want to know how one business owner went from being the bottleneck to having a business that runs without him?
I break it all down here
7 out of 10 business owners aren’t ready for the big payday they’ve worked so hard for.
Just like a team that dominates the season but falters when it matters most, many businesses fail to sell—not because they aren’t profitable, but because they aren’t ready.
If your business depends on you for survival, it’s not sellable.
Here’s what you need to know to prepare for your moment:
Life doesn’t warn you when it’s about to change everything.
Most people live like tomorrow is guaranteed—but it’s not.
In my latest article, I dive into a critical question every business owner must ask themselves to safeguard what matters most.
This one shift could mean the difference between thriving in uncertainty—or scrambling to recover.
Because the best time to prepare isn’t after the phone call. It’s before.
Lose in the playoffs? Tough break, but you dust yourself off, train harder, and take another shot next year.
In business? Let’s just say the rules are a little… different.
How different?
My first hit on the high school baseball team? A home run.
Sounds impressive, right? But what happened before that might surprise you. Let’s just say I wasn’t exactly team material when I started out…
It took a mentor, some tough lessons, and a total transformation to make it to that moment at home plate.
The same kind of transformation your business needs to break through to its next level. Ready to see how?
“For she is more profitable than silver, and her gain is better than fine gold. She is more precious than rubies; nothing you desire can compare with her.” (Proverbs 3:14-3:15).
We’re talking about Sophia…
More specifically, the Greek word for wisdom.
And how tapping into Sophia or wisdom can transform what your business provides you.
“Sing us a song, you’re the piano man…”
Hearing those lyrics took me back to a snowy Christmas Eve years ago, driving through Chicago in a blizzard to pick up my friend Don. We slid into snowbanks, laughed until we cried, and celebrated late into the night.
Years later, Don built a thriving business and a life he loved abroad. But his story has always stayed with me—and not for the reasons you might think.
Profitability alone doesn’t guarantee a buyer will be interested in your business. In fact, many owners don’t realise that 7 out of 10 businesses fail to sell—not because they’re unprofitable, but because they lack what buyers value most:….
“I ain’t missing you at all… since you’ve been gone.”
That’s the song your business should sing when you’re away.
If your business misses you every time you step out—whether it’s for a holiday, a family event, or even a few hours—it’s a sign of trouble.
A friend of mine recently jumped on a plane for his 12th trip in just nine months. He’s headed to Europe for some skiing and a bit of downtime to enjoy a hobby he’s fallen in love with.
But here’s what’s remarkable: his business doesn’t miss him.
It wasn’t always this way. Just a few years ago, he was stuck working 80-hour weeks, tethered to his desk and overwhelmed by the daily grind.
The turning point? He decided ……
When you’re running a business, it’s easy to think buyers will see the value in everything you’ve built—the late nights, the sacrifices, the blood, sweat, and tears.
But buyers don’t care about brownie points.
They care about what your business can do for them. If you can’t answer that, your business could end up like Sally’s….
“I know kung fu.”
That line from The Matrix always stuck with me. Imagine downloading a lifetime of knowledge—mastering martial arts, business strategies, or customer service excellence—in seconds.
While we can’t quite do that yet, what if you could save years of trial and error in your business?
Back in 1999, I took a road trip to the American River—the exact spot where James Marshall discovered gold in 1848 and kicked off the California Gold Rush.
When Marshall first found gold, the area was quiet. No crowds. No rush. Just endless opportunity for those who knew where to look.
It reminded me of our last Business Value Happy Hour.
A small group of us listened as one of our peers shared how he turned his business into a goldmine
Don’t miss the next opportunity. Find out more inside…
2025 is here, and it feels like a year of growth and opportunity.
This year, I’m doubling down on some exciting new initiatives designed to help business owners take their companies to the next level. From collaborations and workshops to practical strategies you can apply immediately, I’ve outlined it all in my latest post.
2024 taught me some big lessons—ones I thought I already knew but needed to learn again.
These lessons reshaped how I approach my business, the people I surround myself with, and the value I bring to my clients. They’ve set me up for a major shift in 2025, and I’m excited to share the journey with you.
Curious what I learned and how it might apply to you?
“Sell the team… Sell the team…”
The chants echoed through Soldier Field as frustrated Chicago Bears fans voiced their anger after yet another loss.
But here’s the irony: The Bears could sell tomorrow for over $1 billion, no questions asked.
Why?
Because they’re the perfect example of a sellable business.. including 5 key areas you can have in your own business -without worrying about poor blocking or bad time management:
“I didn’t want the business. I just wanted my dad.”
A reader sent me that after my last post — and it remined me of the song Cat in the Cradle.
His father built a profitable company from nothing.
But it took everything from him.
Time. Health. Connection. Life.
When he finally offered it to his son —
the answer was no.
Not because the business didn’t make money.
But because no one else could survive it.
Founders, if you’re building something no one wants to inherit…
Maybe it’s time to change what you’re building
He built it for his son.
His son didn’t want it.
And now the business is gone.
Founders — your legacy only matters if someone actually wants it.
Let me show you how to make sure it’s worth passing on — or selling for millions.
I haven’t trimmed my beard in two weeks.
Not because I’m lazy.
Because the only guy I trust is out of town — and I’d rather look like a werewolf than let the wrong hands touch my face.
That’s loyalty.
And if your business doesn’t have customers who feel that way about you — you’re leaving a goldmine untapped.
Let me tell you why the best clients are the “wolfmen”…
(And why you never, ever let them go.)
I saw a restaurant commit business suicide.
I watched a project lose its sponsor and still gain value.
And I spent 7 weeks away — not because I’m rich.
But because I built for control.
Most entrepreneurs build themselves a cage.
Q4 is about unlocking the door — and stepping into open roads and open skies.
If you want real control over your time, money, and relationships…
Stay tuned.
What if the client you’re afraid to lose… is actually the one suffocating your business?
I’ve fired clients before.
Some readers hated me for saying that.
Some unsubscribed.
But what happened next was a lesson in revenue, sanity, and scaling.
Blindly believing that the “client is always right” can be a recipe for killing your business margins and your family life.
The Boss You Should’ve Fired 6 Months Ago
Your client doesn’t pay your salary — so why are they treating you like an employee?
Here’s how one midnight meltdown showed me exactly who needed to go — and what happened when I pulled the trigger
The Boss You Should’ve Fired 6 Months Ago
What do you do when your CEO storms out, ghosts the board, and then casually shows back up expecting his job back?
Let me tell you what one founder did — and how it cost him everything
They cut $150K in “non-essentials”…
Then lost $5.2M in company value.
When margin obsession becomes value destruction — here’s the mistake they made, and how to avoid it.