8 lessons from 2025 that changed how I run my business

I just closed the books on 2025.

And before jumping into 2026 with a fresh set of goals and strategies, I did what I do every year: I audited the hell out of the past 12 months looking for new lessons learned, old lessons relearned, and—maybe most important—lessons unlearned, or things I was simply wrong about.

Some of these lessons cost me time. Some cost me money. A few cost me both.

But every single one changed how I operate.

So here they are—eight of the highest-leverage lessons from 2025. Not theory. Not stuff I read in a book. The expensive kind you only learn by screwing up and figuring it out.

Here’s something that’ll keep you up at night: Every limitation you have as a founder gets baked into your business and your team.

Think small? Your business stays small.

Can’t delegate? You become the bottleneck.

Insecure around people better than you? You’ll never build an A-team.

I worked with a founder a few years back—sharp guy, solid entrepreneur. But he needed to be the smartest person in the room. He’d hire people with serious experience and strong track records, then get insecure when they actually knew their domain better than he did.

So he’d step in. Create conflict. Eventually, those A-players would leave.

His “fix”? Hire yes-people. Folks who’d just do what he said without pushback.

I watched that become a permanent ceiling on the business. The executive team that could’ve been stacked with killers turned into a roster of order-takers.

That limitation—his insecurity—became the business’s limitation.

Personally, I’ve learned how my ADHD can lead to a business that’s unfocused and chaotic. How a passion for quality can become perfectionism that leads to slow progress. And how easily a bias for action and “getting shit done” becomes an inability to delegate.

Upgrading your business means upgrading yourself.

Which is exactly what I see from the best founders I know—the ones running $50M, $100M, $200M+ businesses without burning out. They’re constantly upgrading themselves. They challenge their own beliefs. They seek out people smarter than them. They’re deliberately evolving.

That steady evolution compounds into massive differences in how you see things over time.

One of my good friends runs a $200M gym empire. Before I run an idea past him now, I stop and think, “Wait, what’s he gonna say?” Because he sees things completely differently than most people.

He sees risk where others see opportunity. Opportunity where others see risk. What looks hard to most founders looks simple to him—and vice versa.

That didn’t happen by accident. He’s spent years deliberately upgrading how he thinks, surrounding himself with people who challenge him, staying curious about other perspectives.

Because he knows: If he stagnates, the business plateaus.

Your business can only grow as fast as you do. If you’re not deliberately working on your own limitations, you’re installing them into everything you’re building.

I used to manage big budgets in corporate. I could be selective. Offer killer comp plans. Go hire A-players all day long.

When I went out on my own, budgets got tighter. And I developed a bad habit: I started hiring cheap.

I had a big vision with all this work that needed doing. So I’d think, “I need three people, but I only have budget for this much,” and I’d hire multiple cheaper people to try to get it all done.

Terrible idea.

What I should’ve done was prioritize ruthlessly, pick the single most important thing, and hire one badass to attack it.

Instead, I ended up with mediocre people on the team. Which meant more noise in the business. More oversight from me. More micromanaging, fixing, cleaning up messes.

In most cases, it wasn’t even leverage. It diluted my time more than it expanded capacity because I was constantly managing mediocrity.

The business didn’t move forward nearly as fast as it would have if I’d said, “We’re letting fires burn. That’s the priority. I’m hiring the best person I can find to own it.”

This past year, I went back to my roots. I made it a priority to only accept A-players. And yes, that limited what we could tackle. But it forced better prioritization—and the business accelerated dramatically. December marked the highest month of revenue since striking out on my own in 2019.

Here’s the thing about hiring A-players: You need to treat it like video production.

If you spend way more time on pre-production—research, strategy, getting the hook right—you get better results and dramatically less work in post. Same with hiring.

Most people jump straight to the job post, get flooded with resumes, pick someone who’s “good enough,” and then wonder why it’s not working.

Instead, spend more time on strategy up front.

We spend so much more time on this now. And hiring is faster. Ramp-up is exponentially faster. The quality of people we’re stacking the team with is night and day.

The caliber of people you bring into your business has massive impact on speed, effectiveness, and how much margin you have as a leader to focus on other things versus managing mediocrity.

One A-player is worth 10–20X what a mediocre hire delivers.

Not 10–20% better. Actually 10–20X.

Hire accordingly.

Okay, so you hired the A-player.

Here’s the shift I had to make—and it’s a relearning from my corporate days that I’d somehow lost along the way.

When you have mediocre players on the team, you lead by effort. You clock long hours. You stay in the weeds. You execute alongside them to demonstrate “this is the standard—we go hard in the paint here.”

That works when people need to see the work ethic modeled. When they need you showing them what’s expected through sheer force of example.

But A-players? They come batteries included (one of our core values now).

They already have the work ethic. They’re already wired to execute. They don’t need you demonstrating how hard to work—they need clarity on what to work toward.

And here’s where I screwed up as I started upgrading the team this past year:

I kept investing my time the old way. Clocking 12-hour days. Staying in the weeds of execution. Leading by effort and example because that’s what had been required with mediocre talent.

But that came at the expense of what A-players actually needed from me: clarity on the goals, the targets, the objectives. What does success look like? What’s a home run? What are the boundaries of this role?

I was spending time doing and not enough time defining.

When I made that shift—stopped doing more and started defining more—everything changed.

We established more clarity in the role itself, what the expectations were, what success looked like and how it’d be measured, and what it took to achieve it. That’s exactly what A-players need to execute at their full potential.

That shift enabled me to truly start delegating again, which has created true leverage in the business and set the stage for the business to expand well beyond me. Because it doesn’t require my direct execution—and it’s something I can do for 5, 10, or 20 more people we will eventually add to the team.

Upgrading your team requires upgrading how you lead the team.

A-players don’t need to see you work. They need to know what winning looks like.

Provide that clarity, and they’ll run through walls to get there.

This is arguably the mistake I had to repeat more times than any other for it to truly be learned. Because I LOVE me some systems in a business. But obsessing over them can actually impede growth.

Here’s how it happens for me: I get an idea for an outcome I want to achieve.

Next, I think about how we’re going to do it.

And immediately, my brain jumps to, “How do we systematize this? How do we make it scalable?”

Then I spend my time (or my team’s time) building out systems and processes ensuring everything is scalable and executed efficiently—before I’ve proven the content, or that the strategy of volume across channels, actually works.

It’s something I’ve done more times than I can count—with operations, reporting, task management, and yes, content.

But the lesson has finally set in.

Because of that, I’m far more diligent about not asking, “Is that process scalable?” and more disciplined about asking, “How do we know this works at all, and what does it take to do it really well?”

If I don’t know the answer to that, we’re wasting time trying to do it faster, easier, cheaper, or more efficiently. Because it may not need to be done at all.

Prove it works. Learn what makes it work. Then systematize.

«Related podcast: I Built a 7-Figure Stream with a Six-Pack and a Spreadsheet»

I’m convinced: Foundational AI skills are essential for anyone leading a team or business. Not optional.

Here’s why.

Without a solid understanding of what AI is capable of, you won’t be able to allocate resources in your business effectively. And if you’re a CEO or business owner, that is your most important job.

For example, I’ve been paying a copywriter to turn content I’ve already created into other forms of content. They mine my YouTube channel, this newsletter, and my podcast to repurpose it into content for other channels (similar to the content system I described above).

Recently, as I was reviewing a batch of content to approve, I had an idea.

I’d been experimenting with Claude Skills—preprogrammed prompts to make complex but repetitive prompting easy. And I thought, I wonder how my experiment would stack up to my copywriter.

So I put the related podcast transcript into Claude, used the Skill I created, and got the exact same output as what was submitted by my copywriter.

Not close. The same post. Almost verbatim. Same hook. Same structure. Same everything.

I’ve learned my lesson about systematizing too quickly—but in this case, I already had all the data I needed to know whether the content worked. So I systematized.

Within one day I built a system that fetches new podcast episodes and puts them in a spreadsheet, grabs the transcript and puts it into a file, sends that transcript to an AI model, uses preprogrammed prompts to create content, critiques the content and puts it in a new file, sends a link to that file back to the original spreadsheet, then creates a task in my daily task manager to review approve.

Automatically.

It took me about 8 hours of coding with the help of AI to replace my copywriter and get the same output, on-demand.

(And now armed with the understanding of how other people can use my content to get the same content, I dramatically improved the process and get a better output with more variety.

I’m not suggesting you need to know how to code with AI if you’re a CEO or business owner.

But I strongly believe that knowing what’s possible with AI—and how to harness its strengths while protecting against its weaknesses—is essential if you want to remain competitive as it evolves.

AI can dramatically reduce your expenses, or lead to paying 10X more for something than you need to. It can create leverage for productivity, or drain time and resources. It can help your team get smarter, or lead to lazy thinking.

The difference maker is you.

And not someone you delegate it to. Because the funny thing about AI knowledge is, many of the people who understand its potential most right now are gatekeeping that knowledge in order to monetize it.

«Related YouTube video: AI Is Making Your Team Stupid»

I’ve been posting online for six years. Primarily LinkedIn, but also YouTube, podcast, some on X. I’ve driven millions in revenue from my personal brand.

I started posting because I liked writing and wanted to share points of view I felt were underrepresented in sales and leadership.

Content quickly became my primary source of business. And that changed the dynamic entirely.

I was still creating content I wanted to create, but there were now “rules” for content marketing that didn’t exist when I was creating content just to create: write for a tightly defined target market, focus on a few narrow pillars, be repetitive (say the same thing 10,000 times), post every day, use personal profiles for maximum reach.

The niche-down-and-repeat playbook works. If you’re posting content purely to generate leads, it’s proven.

The problem? I got bored with content. I felt like I was on an assembly line, cranking out content to check the box.

Yet I wasn’t ready to completely hand it off to a ghostwriter or AI because I’m terribly picky about what goes out on my personal profiles. (A ghostwriter once called me the worst kind of client you could have: I love creating content and care more about the accuracy of the message than results.)

There was constant tension between creating content I wanted to create and creating content I had to create to grow the business.

This year, I made a decision that changed everything: I decoupled my personal brand from the businesses I own.

I committed to creating the content I wanted to create, and built a simple process to turn that content into marketing.

My content no longer needed to fit within narrowly defined pillars. I no longer had to write only for one tightly defined audience. I could start creating content for the reason I started in the first place: because I enjoy it and want to help others through my experiences.

My identity and brand is not my business’s identity and brand.

This unlock has been massive.

Because I’m creating content I want to create instead of content I have to create, I’ve become a content machine again. And ironically, we’ve seen a sharp spike in the channels where I’m publishing more freely.

Not surprisingly, 70–80% of my content is still about the same stuff I always write about: sales strategies, growth strategies for MSPs and IT businesses, leadership and entrepreneurship. That’s what I’m genuinely obsessed with.

But if I veer off on a tangent about destructive social media marketing trends or neurodiversity lessons I’m discovering (which has been a big topic in the Green household this year), I can do that without confusing customers of MSP Sales Partners or companies we’re considering investing in.

The best part? It hasn’t resulted in less content to use for marketing. We have more content than we know what to do with now.

I simply crank out raw, unfiltered content on a regular basis on my podcast and X. My team mines all of it for marketing.

Candidly, I don’t know if doing this from day one would have had the same impact. But after repeatedly hitting the plateaus and challenges of leveraging a personal brand to grow a business, what we’re doing now feels like the most enjoyable and sustainable approach in all six years of creating.

This is an unlearning.

If you go back through my content over the years, I talk a lot about the importance of vision. I coached people on exercises to extract the vision from their head—what they’re building, who for, what they want that business to be.

The thinking: Get clear on what you’re building so you can be intentional with decisions.

Because I see people build businesses they become prisoners of. Three, four, five years in, revenue is good, but they can’t stand the team, the product, the clients, the systems.

If you’re proactive with a clear vision, you’ve got a decision-making filter. New client offers you a bunch of money to do something that conflicts with where you want to go? You can say no.

Still believe that’s true.

But here’s what I learned this year: That’s not the only way.

That’s the Jeff Bezos approach. Bezos famously articulated what Amazon was going to be very early. Almost prophetically said, “This is what we’re building,” then built it piece by piece.

That’s one way.

The other way is to treat it like a blank canvas. More art than science. You’re not assembling every brick with a clear outcome in mind. You’re building because you love building, and you iterate as you go.

Strategy unfolds dynamically.

You don’t need the clarity of vision to pull you forward. You have the love of the process keeping you going.

That’s more the Steve Jobs approach. Jobs famously said, “You can only connect the dots looking backwards.”

Bezos approach: Crystal clear vision, builds intentionally toward it.

Jobs approach: “This is going to be random. There’s going to be iteration. Decisions today create optionality that doesn’t exist tomorrow. So let’s get started and make intentional decisions as we go.”

Both work.

One caveat: If you go with a fuzzy vision—recognizing it’s a blank slate—and you don’t love what you’re doing, it becomes very frustrating and affects sustainability.

If you don’t have a crystal-clear vision of what you’re building and find the process of building a business tedious and unenjoyable, chances are this will not be a sustainable path for you.

And, by the way, there’s nothing wrong with that.

One of my mentors once said, “Entrepreneurs have to be slightly off. Otherwise, there’s no reason we would keep doing this to ourselves.”

Speaking of being slightly “off.”

This year has been a waterfall of learning about myself through my children.

Earlier this year, we discovered that one of our sons was dyslexic and had ADHD. We had the opportunity to learn a lot about how those things can create challenges, particularly in school.

We also had the opportunity to learn that those things are superpowers when leveraged properly.

In doing this, I discovered how much my own ADHD affects how I build and lead businesses—and discovered that I have level one autism (previously known as ‘high functioning autism’ or Asperger’s).

I learned enough this year to fill a book if I really reflected on it.

But the big takeaway is this: the better I understand and accept my strengths and weaknesses, the more of a superpower my strengths become, and the less of a liability my weaknesses are.

Because I can now better understand why, after decades of self-improvement work, I barely move the needle in certain areas.

Meanwhile, other aspects of this that are exceptionally hard for most people are incredibly easy for me.

It’s allowed me to stack the team with people who offset my weaknesses. I focus on the areas of the business that are truly my superpower.

It also explains why my wife and I work so well together. Our mutual strengths and weaknesses fit together like puzzle pieces, creating a 1+1=3 dynamic for us.

If any of this is relatable for you or anyone you know, I highly recommend watching this video from my friend Dave Rendall. It is easily the most impactful video I watched in 2025.

Here’s what I’ve realized: Expensive lessons separate people who build something real from those who dabble.

The question isn’t whether you’ll face expensive lessons. You will.

The question is whether you’ll learn from them fast enough to make them worth the cost.

Most people pay the same tuition over and over again.

Don’t be most people.

I’m breaking down each of these lessons in more detail and sharing more of them in individual podcast episodes starting this upcoming week.

Find us on your podcast player of choice by clicking here.

Adios,

Ray