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I'm an operator documenting what I've learned building revenue engines over the past decade.

CEO @ MSP Sales Partners. Managing Partner @ Repeatable Revenue. Former PE-backed CEO. Former Managing Director at the U.S. Chamber of Commerce. Spent six years building sales systems for Robin Robins (TMT, sold to PE). Built revenue engines for 100+ service businesses.

I write about what I've learned: how sales systems actually scale, the difference between activity and productivity, why hard choices matter more than hard hours, building a business without burning out.

This isn't guru content. It's lessons from the work... what I got wrong, what finally clicked, patterns I see across businesses, frameworks that actually held up under pressure.

I write for three types of people: Strategists thinking about exits and scale. business owners stuck at a plateau trying to break through. Thinkers who want to build intentional lives, not just businesses.

If you're one of those (or all 3), follow along.

Ray J. Green

"I do have to tell you, Ray, there is a small chance of sudden death."

My cardiologist. 

About a year-and-half-ago following a chance diagnosis of hypertrophic cardiomyopathy (HCM). 

I initially reacted the way you'd expect. 

"WTF am I supposed to do with that?!?!"

And, "Why in the hell is this happening to me?"

After all, I do 2 hours of cardio a day. 

In fact, my last echocardiogram shows I have 'athlete's heart.' My heart has literally grown because I've exercised it so much--in a good way. 

So how do I end up with a heart condition? 

But I had it wrong. This wasn't happening TO me. 
It was happening FOR me. 

That reframe changed how I look at this. Even with a couple ER visits in recent weeks. (Which ended up perfectly fine and just more awareness.) 

And it's reframed how I see every hardship in general. 

I break it all down in 10 min podcast here: https://lnkd.in/e3FKQD-m

CEO @ MSP Sales Partners | Man. Partner @ Repeatable Revenue | Ex-PE Backed CEO | Former U.S. Chamber Man. Director

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6 years ago I started posting on LinkedIn because I actually enjoyed creating content. 

I also had a decent amount experience turning around sales teams & businesses using some unorthodox practices. 

So, I wrote about it. 

And wrote about leaving the C-Suite, moving my family to Cabo, and figuring out how to generate income from a Mexican beach. 

My wife and a couple friends were the only people who liked my posts. Sometimes not even them. 

But I actually enjoyed the process. And I wrote just about every day. It was easy. It was light. It was enjoyable. 

With just 3 or 4 likes per post (I don't have many friends), I even managed to get a couple clients from content. They saw a post, looked at my half-assed "optimized" profile, and hired me to give them advice. 

Shortly after that, creating content became a task. Something I had to do every day to be seen and known. To generate some business. 

Sit down. 
Think of something to write. 
Hammer out a post. 
Make it look pretty with descending lines. 
Post. 
Every day at the same time. 

It started to consume every morning. 

Then I learned that commenting on everyone else's posts helped my posts get more reach. So I'd block time every day to "engage" with people's content. A couple hours a day... on a slow day. 

Then I decided to start "batching" content, sitting down and hammering out 6 or 7 posts in one setting and scheduling them all out in advance. 

Then I started recycling content, taking old stuff, refreshing it, and adding it to a second publishing slot for the day. 

Before long, I was cranking out 21 posts a week and racking up who knows how many hours of commenting. 

For all intents and purposes, I was a machine. 

And that's before AI got added to the mix. 

But along the way, I stopped enjoying the process. 

I managed to systematize the joy out of writing. 

Content was forced. Engagement was forced. 

I wasn't sharing a viewpoint I felt strongly about. I wasn't enjoying the process. I was just "building an audience" and generating leads. 

And to some extent, that's perfectly fine. It's LinkedIn. We're all here to do business in one way or another. Myself included. We all gotta eat. 

But today I made a decision: I'm going to start spending more time doing things I genuinely love doing. And one of those things is writing for the sake of writing. 

Not for leads. Not to check a box. Not at a specific time. Not on a schedule. Not in conjunction with 7 hours of commenting on other people's posts. 

But for the joy of it. 

And hoping it adds value in one way or another to someone else here. Even if it's back to 3 or 4 likes per post. 

This post is the first stab at that. And I'm already enjoying this process a hell of a lot more. 

If you want to follow along, comment "WRITING" to receive my.... kidding. 

You'll never see another handraiser post like that from me again. But that's a post for anther day. Maybe tomorrow. But then again, maybe not. 

See you around.

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OCAS 2.0

It took me 40 months to break $40k/month as an independent consultant. If I started again, I'd do it in a fraction of the time. I created this course - and share it for FREE - to help others do exactly that: https://www.rayjgreen.com/digital-course

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Join my email list for practical advice on sales, strategy, and self-mastery from an operator, not a guru: https://rayjgreen.beehiiv.com 

Chief Executive Officer

Managing Partner

Writer & Podcaster 

Expert In Residence: Sales & Sales Management

When people say, “just stay consistent” or “it’s about volume,” what I hear is: work hard, cross your fingers, and hope you get lucky. 

Just read a post from a popular ghostwriter on how to go viral. His hack? Just have to keep posting. 

Over the weekend watched a YouTube video from a popular business guru on how to find the right growth strategy. Solution? You just have to keep trying new things until it works. 

But if you take this advice literally, and completely, you’re essentially saying “Just keep doing shit until you get lucky.”

And if you’re wired anything like me, that’s not going to fly. Not is it going to be sustainable. 

Volume does matter. Consistency does matter. 

But just like driving to the office everyday doesn’t train you to be an F1 race car driver, volume and consistency aren’t enough. 

It’s intentional volume. Combined with focused reflection and aggressive iteration. 

A critical mass of effort done on purpose. Then regularly reflected on to discern what’s working and what isn’t. And adjusting accordingly. 

Volume without intentionality and iteration is wasted energy. Or lottery ticket-type betting. 

And a good way to burn out.

The thing you're most certain about in your business is probably the exact thing keeping you capped.

Just took my kids to a Museum of Illusions in Utah. Your brain swears things are true that aren't—by design.

Same thing happens in business. 

I've spent a lot of time this past year with founders of $200M businesses. And founders of $2M businesses. 

Biggest difference between them? 

A few simple beliefs. 

I break down what this looks like in a 10 min podcast. 

Tune in to listen here: https://lnkd.in/eCpt5-i7

My inner critic is a loud SOB.

Good workout? 
You could've gone harder. 

Eating okay? 
Could be cleaner. 

Time with your kids? 
Could be more present. 

Productive at work? 
Could've done more.

It never stops.

I used to fight it. Try to quiet it. Tell myself that I should be easier on myself, like everyone says you should.

And you know what happened?

It made things worse.

Because then I had the critic AND a voice criticizing the critic. 

Layering noise on top of noise.

So I stopped fighting.

I realized my inner critic is a feature. Not a bug.

That voice... the one constantly pushing me... is what I credit for jumping literal generations for my family.

Growing up with divorce. Absent father. Broken homes. In a foster home at one point. Not a lot of money. Or formal education. And layers of other challenges. 

Today? Happily married. Two healthy boys who know nothing of that instability. MBA from a top school. Living in Cabo. Traveling the world.

That tough critic that pushed me said "This is not for you. You can do better. You will do better."

And I did.

Here's the nuance though.

I've learned to allow the critic to push my actions. My habits. My standards.

Without allowing it to define my worth.

I can accept that my actions will never be "enough" while also knowing that I am enough as a person.

And that's a big effing difference.

One keeps you sharp. 

The other keeps you whole.

Dropped a podcast expanding on this a bit if you're interested: https://lnkd.in/eAm7GyPn

Most salespeople treat discovery like a podcast interview.

"Tell me about your business. How many users? What's your current setup? Walk me through your IT history."

Like you're only there to gather information and collect facts.

And I promise you it's costing you deals. 

Something that's helped the hundreds of consultative sellers I've coached: 

Discovery isn't information gathering.
It's the first step of a strategic close. 

Run a bad discovery and the rest of the process is going to pay the price. 

Example for IT companies:

Bad discovery: "How many servers do you have?"

Good discovery: "How is IT accelerating your growth or holding it back right now?"

One gets you data. The other gets you business impact—the ammunition you need when you're actually trying to close the deal 3 weeks later.

The same thing happens in assessments.

Example for IT companies: 

You find cracked passwords. You find too many O365 admins. You document the vulnerabilities.

Then you present them like a checklist: "You have X problems."

But the MSPs who close? They explain why that matters: "You have cracked passwords on essential systems. Let me tell you what happened to a company last month when a disgruntled employee knew they were leaving…"

Every step in your process—from first call to final proposal—has one job: move the deal forward.

Not educate. Not inform. Not "let them think about it."

Move. The deal. Forward.

I shared a podcast on this, and why despite the stigma attached to it, it really is Always Be Closing. 

I explain why and how here: https://lnkd.in/e7SVFiVx

I wish there were more 'right' and 'wrong' calls in business. But what I've learned from 20 years of leading teams, divisions, and businesses? 

It's a lot more "good bet vs bad bet' and a lot less 'right decision vs wrong decision.' 

Regardless of whether you're running $500K business or a $500M business, when you're making high level decisions about where the business should go, you're operating with uncertainty. 

You may be 55% sure on some days. 90% sure on a good day. But that's the job description. 

The problem is, I see this crush a lot of founders. 

They go this direction. Then that direction, Start this project. Change to that project. Pick this priority. Then that priority. 

It's exhausting just to watch. 

Even more exhausting to do. I know from experience. 

I recorded a 10 min podcast for any founder or business leader that's felt overwhelmed by uncertainty. And anyone that's let that uncertainty lead to perpetual pivots and indecision. 

You can tun in here: https://lnkd.in/eVNUZDuY

One of the biggest challenges with digital marketing is remembering that the people in your feed aren’t the people buying your stuff. 

(Unless you sell products and services to online creators.) 

I’m guilty of forgetting this myself. 

I scroll here and see a bunch of people using AI in really cool, new ways. 

That gets baked into my head when creating a podcast or YouTube video on AI. 

Then I go to an event and talk to my actual customers and prospects and realize, they’re not using AI in their sales process in some of the simplest ways. 

But it’s not just with AI. It’s with all our messaging. 

We have what’s called “the curse of knowledge.” 

When we forget what it’s like to not know what we know so well. It’s a trap a lot of experts fall into. 

So, reminder (to myself as much as anyone) to spend a little more time creating for the people we want to listen. 

Not other creators.

Years ago I gave my wife terrible business advice.

Not because it didn't work.

But because it did.

She had a custom baby bedding business doing $25K/month on Etsy. Six-month waiting list. Countless 5-star reviews. People literally begging her to make "just one more."

She asked for my input.

I looked at all the indicators and told her what any business advisor would say: "It's time to scale."

She had some resistance. "Yeah, but I love sewing."

But she pushed on.

She hired people. Built systems. Went from spending her days doing what she loved—talking to customers, designing patterns, creating with her hands—to managing quality control and dealing with employee issues.

The advice worked. The business scaled.

And she fucking hated it.

Her initial resistance? That gut instinct she had?

Spot on.

She didn't want to build a business. She wanted to do the thing she loved and get paid well for it. Those are two completely different games.

My advice was biased by what I believed a business should be. Not what her business could be for her.

I see this happen quite a bit. And I'm more aware of it having gone through my wife's experience with her. 

I recorded a podcast breaking down: 

→ Why you should pick advisors carefully (even if you love them)
→ Why product-market pull doesn't mean you should scale
→ How to filter advice so you build the right thing (for you, not for them)

Listen in here: https://lnkd.in/eCtMPwpn

Our 4th graders were begging for cell phones. 

Parents made a pact: rewind the clock & meet 'em halfway. 

No smartphones... 

But they were genuinely thrilled to get these retro beauties instead. 📞✨

You know why so many salespeople waste 10 minutes talking about the weather?

Because they think being liked is the same as being trusted.

It's not.

Here's how I think about it:

If I needed brain surgery, I wouldn't pick the surgeon who makes great small talk.

I'd pick the one who asked questions that prove they've seen my exact condition 50 times before.

Likability gets you in the door. Credibility gets you the deal.

(If you are selling anything of high importance.) 

But there's the psychological trap a lot of reps fall into:

Small talk feels safer. It's comfortable. It doesn't require you to demonstrate expertise or challenge assumptions or risk saying something that might make the prospect uncomfortable.

So you hide behind it.

You talk about dogs and football teams instead of asking the question that might make them think: "Wait, maybe our current IT setup isn't as solid as we thought."

Real rapport is built on confidence, not comfort. 

Confidence that you know their industry. That you've done your homework. That you're not afraid to respectfully push back when they tell you something that's not accurate.

I recorded a podcast breaking down: 

→ Why people confuse likability with trust (and how to fix it)
→ The preparation work that builds real credibility
→ How to show up as an expert, not an order taker

Listen to the whole thing here: https://lnkd.in/eDs2mfSZ

There's a name for what happens in a business when leaders have no spine. 

You know what I'm talking about. When the people responsible for making the tough calls... just don't. 

They ignore underperformance. 
Avoid difficult conversations. 
Procrastinate making hard decisions. 
Or just never make them at all. 

From a business standpoint, it's called 'management debt.' 

'Management debt' compounds just like financial debt. 

It destroys cultures. And it can stunt growth just as much as irresponsible financial debt can. 

I recorded a quick podcast breaking down: 

→ What management debt is (vs. real leadership)

→ The compounding impact it has on companies 

→ How to keep it from accumulating in yours 

Tune in here: https://lnkd.in/eT3aBrt2

We all have beliefs that aren’t true. Every single one of us. 

The question is: How much are those beliefs holding us (or our business) back? 

Last week we took our beach kids on a ski trip to Utah for a few days. 

(“Dad, is that real SNOW?!?!) 

We had an unexpected delay in Salt Lake City and stopped by the Museum of Illusions—which is basically an hour and a half of mind bending experiences. 

It’s display after display of, “How in the hell is that happening?” 

And what it comes down to is your brain creates shortcuts with limited data. It stitches information together in a way that makes sense… but isn’t true. 

Like this picture. 

The tops of both of these boxes are the same size. Hard to see. But they even give you a block to hold over it to confirm. 

It’s harmless in this controlled environment. 

But what if the tops of these boxes represented a critical belief you held about something of importance that was holding you back. 

You know, the belief that: 

— “This business just doesn’t have the potential.”

— “That idea will never work.”

— “I’ve got to have [money, experience, connections, etc]  before I can do that.”

— “I’m too [young, old] to do this.” 

— “That channel doesn’t work anymore.” 

And what if it was just completely… wrong? 

An illusion that was holding you back from a monumental shift and achieving what you wanted. 

I've spent a lot of time this past year with entrepreneurs who've built $50M, $100M, $200M businesses.

I've also spent a lot of time with entrepreneurs who are struggling to get there. 

And the biggest difference I see is their belief systems. 

Founders who struggle to get to the next level typically have a belief that’s holding them back. Something they know to be true… that simply isn’t.  

A common one being that they are more essential to day-to-day operations than they really are. 

The question I’m asking myself today: What am I dead certain is true… that isn’t?

How about you?

I'm on Facebook the other day and see an ad: "Every sales expert is telling you the same lie—you need to build rapport before you sell."

The pitch? Buy my $37 course to learn how to sell without rapport.

If you read on, you'll see this supposed sales expert was making a common mistake: 

Confusing rapport with small talk. 

Rapport = trust & credibility. 

Small talk = likability. 

Talking about the weather. The local football team. The family pictures on the desk.

That might make you likable. But it doesn't make you credible.

And if you're selling anything of real importance to someone, likability only goes so far.

Think of it this way: If you need brain surgery, are you going with the doctor you like most, or the one you trust to get the job done? 

I recorded a podcast breaking down the common misconception. 

In it, I break down:

→ Why small talk doesn't equal rapport (and what does)

→ How to establish credibility in the first 5 minutes

→ The questions that prove you're an expert, not just likable

→ Why rapport is an ongoing process, not a one-time event

Listen now: https://lnkd.in/eDs2mfSZ

We glorify the benefits of entrepreneurship like independence, ownership, optionality. 

But those are the very things that crush entrepreneurs once they get going. 

Having an infinite number of options. 
Virtually no certainty while making huge decisions. 
But owning the outcome entirely. 

It's the freedom people think they want. 

But it drives a lot of entrepreneurs crazy once they get it. 

They can't make decisions. And when they do, the immediately doubt themselves and change directions. 

Which basically makes only one thing certain: they won't move forward.

I watched an entrepreneur change their mind on lead gen strategies 8 times recently. 

And I recorded a 10 min podcast breaking down why this happens (from experience). And how we can flip the script on uncertainty. 

Listen in here: https://lnkd.in/eujidhhV

The MSP owner on the phone with me sounded defeated.

His sales rep had just spent three weeks and 20+ hours on what looked like a perfect fit.

Discovery had uncovered real pain points. The assessment was thorough. The proposal meeting went well—good questions, engagement, positive energy.

Then... nothing.

Not a “no thanks.”
Not a “we’re going with someone else.”
Not even a “we need more time.”

Just complete radio silence after weeks of investment.

“This keeps happening,” he told me. “How do we stop bleeding time on deals that were never going to close?”

This was my response:

Open article: Stop Chasing Dead Deals: How to Read Your MSP Prospects Before They Ghost You by mspsuccess.com

Stop Chasing Dead Deals: How to Read Your MSP Prospects Before They Ghost You

Graduate corporate life for entrepreneurial freedom — without jeopardizing your income or family 💚 | Pod: UncageYourself.FM 🎧

Directors. VPs. Executives.
Ready to go Corporate → Founder in ONE Year?

This is the smart path out — without blowing up your life.

We help corporate veterans turn their employer into an investor, compress their job by 50%, and launch a 1-of-1 premium business.

Corporate becomes a short-term asset — not a lifelong trap.

The system is called Corporate Graduation™.
And it works.

You’ve built a strong corporate life. But you’re likely facing 2+ of these:

1) Your time isn’t yours.
2) Work consumes everything.
3) Family & health get leftovers.
4) You’re just going through motions.
5) You know you’re meant for more — but have no idea what.

It’s costing you — emotionally, physically, financially.
You feel stuck. Fading.

That was me.
Divorced. Burnt out.
Later — remarried, rebuilt, and free.

I made my employer my investor.
Cut hours in half.
Launched a business around my genius.
Graduated corporate life — forever.

Now I help others do the same.

Corporate Graduation™ is the system.
165+ have used it to:

✅ Compress their job into 20 hours/week
✅ Exit with runway, not regret
✅ Build a premium service business that reflects who they are
✅ Create leverage through proprietary IP, not more hours

This is how you build your founder future — without burning bridges.

This isn’t about dabbling.
It’s about reclaiming your life.
For your family. Your future self. Those you’re meant to serve.

No “passive income” BS.
Just active transformation — with revenue, clarity, and agency.

Ready to graduate?

👉 DM me “GRADUATE.”

Matt Doan

I left corporate 4 years ago.

Here’s what actually changed:

1) Mondays have energy again.
I wake up early because I want to. Not out of discipline or obligation, but out of genuine excitement for the week ahead. That feeling was gone for years in corporate. Now it’s normal.

2) The Sunday dread disappeared.
That quiet weight that used to settle in by Sunday afternoon — the sense of re-entering a system that didn’t fit — lifted once I started building something I actually owned.

3) My wife became my partner — in a new way.
Cecilia and I now talk about clients, strategy, and impact together. We’re building something side by side. Corporate never could have offered that, and it’s deepened our marriage in ways I didn’t anticipate.

4) My kids see a different version of me.
They see energy instead of depletion. Engagement instead of exhaustion. They’re watching what it looks like to build something you care about... not just talk about it.

5) My health followed my work.
When work creates energy instead of consuming it, everything else responds. Sleep improved. Stress dropped. At 41, I have more capacity than I did at 35.

6) I’m building skills that compound.
Psychology. Sales. Marketing. Persuasion. Category design. These aren’t corporate skills. They’re human skills. They don’t expire when roles or markets change.

7) I finally understand who I am.
Not my title. Not my employer. Me. The founder path forced me to confront things I could avoid for years in corporate. On the other side was clarity I never found climbing the ladder.

This isn’t about hating corporate.

Corporate gave me my Career Capital:
judgment, pattern recognition, credibility.

But it couldn’t give me ownership.

That required a different structure.

---

For those who've outgrown their container.
Jan 19 → https://lnkd.in/esvq8nuY

Monday, your Career Capital starts compounding.

Or it doesn't.

One-time, special event:
https://lnkd.in/esvq8nuY

Here's what most people miss about workshops like this:

It's not information.
It's decision-making.

You slow down and show up.
You become a captive audience — to yourself.
You stop scrolling. Stop reacting. Stop drifting.

And for the first time in months (maybe years), 
you do the actual work:

1) You stop making excuses for your delay
2) You uncover your Career Capital
3) You decide how to deploy it
4) You see what's possible beyond the role
5) You start forging a path no employer could match

That's not just inspiration.
That's the compound effect, taking hold.

Imagine where you'll be 90 days from now.

Not just "thinking about it."
Not merely "planning to start."

Actually in motion.

Energy returning.
Clarity sharpening.
Your family feels the new you.

This is what Corporate Graduation™ looks like.

Those who've already committed to Monday aren't hoping for answers. They're giving themselves permission to move.

One decision.
One workshop.
A new trajectory.

The Career Capitalist™
Monday, January 19
$50: Live + Recording + Assets

One time only.
See you inside.

https://lnkd.in/esvq8nuY

---

PS - Registrants get the IP Builder GPT, Corporate Graduation Readiness Scorecard, category design tools, case studies, and a private 1:1 Founder Game Plan call. Recording included.

The moment I knew corporate couldn’t hold me.

5 lessons it took too long to learn:

For a long time, I couldn’t name what was wrong.

I was progressing.
Respected.
Trusted.

But every time my thinking stretched a little too far — every time I tried to hold a bigger picture — it was quietly contained.

Not shut down.
Just… redirected.

That’s when the tension started.
Not dramatic.
Just constant.

Here’s what I eventually learned.

---

1) Big thinking can be praised and still be unwelcome.

I’d offer a strategic view and hear, “That sounds good.”

Then came the quiet clause:
“But we’re not taking that outside.”

I wasn’t wrong.
My imagination just didn’t fit the system’s design.

---

2) Being valued doesn’t mean being usable.

I was told my work mattered.

But my judgment had nowhere real to land.

When your best thinking can’t move anything, it doesn’t disappear. It withers.

---

3) Side outlets are signals, not solutions.

Publishing in HBR.
MIT Sloan.
The Atlantic.
Think tanks. External channels.

Those weren’t mistakes. They were proof I was trying to breathe outside the box.

What I didn’t see at the time:
External validation was a symptom, not a cure.

Every byline was evidence of capacity the system couldn’t absorb. I kept finding outlets because the main channel was blocked.

Useful moves.
Never satisfying.

---

4) Breakthroughs aren’t about talent. They’re about ownership of environment.

Everything clicked when I sat in a room full of founders.

They had Career Capital too. Decades of it.

The difference was simple:
They didn’t need permission to create.

They built conditions where judgment could compound.
They said yes to themselves.

---

5) Staying longer has quiet, compounding costs.

The financial ceiling was obvious.

The real toll was energy.
Family.
Self-trust.

Saying yes to work that wasn’t me.
Knowing I could be far more impactful — and accepting I wasn’t.

---

That’s when I stopped asking how to optimize my role.

And started asking a harder question:

Where does my Career Capital actually belong?

That question led me out of corporate.

Four years later, I’m a founder.
Still answering it.
On my own terms.

---

PS - If you’re standing at the edge of that question, don't miss what's unfolding here: https://lnkd.in/eDEkDVb2

If corporate feels a bit "too small" lately, 
you're not imagining it.

That feeling usually shows up when your Career Capital has outgrown the container it's in.

Most people respond the same way.

They start with business logic.
Offer. Niche. Monetization.

Or they quietly reach for passive income.

Passive income won't solve under-leverage.
Only owned Career Capital does.

That's why so many smart exits stall.

The real issue isn't effort.
It's missing conditions.

You can't access, package, and deploy Career Capital into founder leverage if you don't first create:

Space.
Then Self.
Then System.

A recent client — VP in ops — followed this sequence. It changed everything:

1) Compressed his corporate load by ~50%
No drama. No bridges burned. No reputational cost.

2) Reclaimed control of time
Now works 3–4 focused hours/day. Deliberate. Surgical.

3) Restored personal leverage
Energy returned. Health improved. Relationships at home strengthened.

Only then did the founder work begin.

He codified his Career Capital into language, frameworks, and IP.
He clarified category direction.
He ran his first program and delivered real results.

Corporate became optional because leverage was no longer trapped inside the role.

That's real Corporate Graduation.
Not escape. Not dependency.

Leverage.

---

If you want to do this work in the right order, I'm running a live, private, one-time workshop:

𝗧𝗵𝗲 𝗖𝗮𝗿𝗲𝗲𝗿 𝗖𝗮𝗽𝗶𝘁𝗮𝗹𝗶𝘀𝘁™
Monday, January 19
$50 (Live + Recording + Assets)

Included with registration:

• IP Builder GPT (to structure your Career Capital)
• Corporate Graduation™ Readiness Scorecard
• Category-claiming exercises you can reuse
• Case study pack + common traps guide
• Private 1:1 Founder Game Plan call

See you on the inside:
https://lnkd.in/esvq8nuY

Has work stopped creating energy for you?
This isn’t burnout.
It’s worse.

Most senior pros describe something quieter.

Disinterest. Going through the motions. Sitting in meetings you've sat in a hundred times, solving problems you solved three years ago. Doing "good work" without feeling engaged by any of it.

(After 15 years, this is how I felt about cybersecurity.)

Work used to create energy. It used to sharpen you. Stretch you. Feed the rest of your life.

At some point, that flipped.

Now it drains energy — and nothing meaningful is replacing it.

That state is not neutral.

When work consumes energy instead of creating it, the deficit shows up everywhere. In patience at home. In health. In imagination. In your sense of building toward a future that's actually yours.

What's really happening underneath is simpler (and more damaging) than most people want to admit:

Your Career Capital — years of judgment, experience, pattern recognition, and hard-earned capability — is going undeployed.

Not unused. Undeployed.

You're applying a fraction of what you've built inside a system that can't fully use it. And when Career Capital isn't exercised meaningfully, it doesn't just sit idle.

It decays.

The most dangerous response here is waiting. Waiting for a reorg. Waiting for renewed motivation. Waiting for something external to force clarity.

Energy doesn't come back on its own.

If work no longer creates it, you have a responsibility to create conditions where it can.

That doesn't require a drastic leap. 

But it does require an environment where your thinking actually matters again — and people who understand what you're navigating.

I'm hosting a private workshop next week for people who recognize this moment and want to think clearly about what to do with the Career Capital they've built.

Details: https://lnkd.in/esvq8nuY

The cost of waiting is quiet. 
But it compounds quickly.

I didn’t know how valuable I was until I stepped outside the corporate system.

Not because I lacked confidence inside.

But because the environment couldn’t show me.

That’s why I built The Career Capitalist™:
https://lnkd.in/esvq8nuY

Happening Monday. A live, private workshop designed to surface, package, and deploy your Career Capital into founder leverage.

Inside corporate, your value gets filtered.

Your judgment gets diluted by consensus.
Your instincts get buried in approval chains.
Your best ideas get spent in meetings that go nowhere.

You’re performing.
Contributing.
Delivering.

But not seeing the full picture of what you’ve built.

It took stepping outside for me to realize:

Every story I lived through → raw material
Every pattern I recognized → deployable insight
Every hard-won lesson → Career Capital to be claimed

And it’s why I hear this constantly from clients once the conditions change:

“Corporate feels simple now. Almost optional.”
“I finally feel in control of my days.”
“I didn’t know I had this much to offer.”

That last one makes me so proud.

Because most people don’t lack value.
They lack the conditions to see it clearly.

Corporate systems are too constraining to reveal what you’ve actually accumulated.

You have to put yourself in founder conditions.
Where your thinking is deployed on your terms.

That’s when Career Capital stops being theoretical.

And starts compounding.

---

Details for The Career Capitalist™
Monday, January 19
$50 (Live + Recording)

Included:
• IP Builder GPT
• Corporate Graduation™ Readiness Scorecard
• Category-claiming exercises
• Case study pack + common traps guide
• Private 1:1 Founder Game Plan call

https://lnkd.in/esvq8nuY

This is a one-time, private event for people who are done playing small inside a big system.

Burnout isn't the real problem.

You've reached a structural mismatch.

After years in the arena, you've built something substantial.

Pattern recognition.
Lived experience.
Relationships.
Reputation.
Judgment.
Talent.

Taken together, this is your Career Capital.

It's stacked. It's real. And it's valuable.

The problem is that the system you're in can only use a tiny fraction of it.

Not because you're capped.
Because the environment is.

Corporate systems are designed for efficiency, predictability, and control. They define a role, reward you for staying inside the lines, and call it success.

Over time, that role becomes a box.
And then a box within a box.

No matter how much Career Capital you accumulate, the system can't meaningfully expand to meet it.

Even changing teams.
Even changing companies.
Even "one more promotion."

The system is the system.

So while your Career Capital keeps compounding, its expression gets constrained.

Your best ideas die in approval chains.
You're solving problems you solved three years ago.
Work that energized you now = going through motions.

That's when the tension starts.

Not because you're ungrateful.
Not because you've lost motivation.
And certainly not from a lack of ambition.

But because you've outgrown the container—which will never change enough to hold who you're becoming.

This might be your first quiet signal that something else is required.

Not a better role.
But a different relationship with corporate altogether.

And a deliberate decision about where your Career Capital will compound.

---

PS - I'm writing deeply about Career Capital this month. The first long-form essay drops on Substack this Saturday — it's about the hidden tax you pay by staying put and what happens when you stop tolerating it.

Subscribe: https://lnkd.in/eDEkDVb2

Career Capital doesn’t sit idle.

It either compounds — or quietly decays.

Inside corporate, decay is the default.

Not because you’re underperforming.
Because the system is designed to consume judgment, not multiply it.

Your experience gets spent in meetings.
Your insight gets diluted by consensus.
Your best instincts get buried under endless “alignment.”

Over time, something subtle but costly happens.

You’re still “successful,” but your optionality shrinks.
Your leverage flattens.
The work takes more energy and gives less back.

That’s not burnout.

That’s Career Capital being used up instead of built on.

Here’s the distinction most people never make:

Most professionals let their Career Capital decay inside systems they don’t own.

Founders decide — deliberately — where it compounds.

Not louder.
Not riskier.
More intentional.

They choose where their judgment is deployed — and who benefits from it.

At some point, the question stops being:
“How do I make this role better?”

And becomes:
“Where does my Career Capital actually belong?”

That question changes everything.

---

PS - I’m writing deeply about Career Capital this month. Saturday’s Corporate Graduation essay breaks down the hidden math of staying put — and what most pros never calculate.

https://lnkd.in/eDEkDVb2

It's been four years since I had a paycheck.

And I'm still here.

Years back, my coach asked something I couldn't shake.

"Is your fire greater than your fear?"

No follow-up. No context.
It just sat there, staring at me. UGH.

I hate that I didn't have an answer right away. 
It's been gnawing at me ever since.

Because here's what I've figured out:
Fear wins by default.

When fear's in charge, you optimize for safety. You wait for the right time. You tell yourself one more year for the bonus, the equity, the title. You do everything except make the actual bet.

And I get it. The golden handcuffs are real. That pressure keeps you sharp. But it also keeps you stuck.

Here's the thing nobody says out loud:
You can't build this new life from comfort.

Something has to break.

We need fire. And it has two parts.

1) Outer fire
It's the forced pressure. The last paycheck. The shrinking savings. You move because you have to. It works. But it's blunt and insufficient.

2) Inner fire
This is the chosen pressure. Why you're doing this. Who you're doing it for.

For me, it's my kids absorbing what they see, not what I say. Them seeing me build a business and choose my own path is arguably one of the greatest gifts I can give them. (Struggles included.)

You need both types of fire: 
Outer conditions that activate you.
Inner conditions that sustain you.

I'll admit it. There are dark days. "How come others move faster than me? Why are they thriving, and I'm struggling?"

Those are the days fear wins.
(But it wins less and less as the years go on.)

My job is to live above the line. In fire. 
Not every second. But more days than not.

Sometimes, you have astounding days. When you earn the equivalent of one or two corporate paychecks in a single day. Or you get a handwritten note from a client that says you saved their life. The fire returns.

You don't feel your way into that. You build it. With discipline. With daily work that rekindles the fire.

Those days I felt broken? It wasn't a dwindling bank account. It was forgetting to build the fire. Letting fear win without a fight.

Which one's greater, your fire or your fear?

Mine said fear for a long time. 
It still does some days.

But I keep asking. And more importantly, I keep answering.

Because your life isn't shaped by the question.

It's shaped by which one you feed.

The quiet frustration you feel isn't burnout.

It's trapped leverage.

Your career capital is decaying right now.

Not because you're losing skill.
Because you're not deploying it.

Yesterday I ran The Career Capitalist™ workshop.

Here are the five ideas that hit hardest.


1) Career capital is stored energy.

Years of judgment, pressure, and decision-making accumulate as untapped power. But stored energy doesn't stay neutral. If it isn't released into the right environment, it implodes.

Career capital needs motion, leverage, and somewhere to be used (hint: someone else's system won't do.)


2) Career capital must become a compounding asset.

Your career capital can only compound when converted into something you own. Left unconverted, they get spent linearly through effort.

Ownership is the difference between earning repeatedly and compounding over time.


3) Labels suffocate career capital.

SVP. Director. Consultant. Coach. Speaker.

These are pre-priced containers with fixed ceilings. The market decides what they're worth.

Labels come with limits. Founders build the room.


4) Career capital has a window.

Experience is sharpest when it's recent, relevant, and energized. Delay too long, and it decays.

Not from lack of ability. But from missing your window of opportunity.


5) You must intentionally package and deploy it.

Unpackaged career capital goes to waste. If you don't turn it into assets — frameworks, language, IP, owned systems — it never compounds.

It just leaks out through time, effort, and obligation.

---

This is what I wish I understood five years ago.

Career capital isn't something you simply have.

It's something you either convert and compound.
Or you quietly lose it.

---

PS - If this resonates, doors are open for the February cohort of our Corporate Graduation™ program. DM me "LEVERAGE" for details.

Stability is quietly destroying you.

Every time you choose the "responsible" move,
you trap energy that needs to move.

Nothing looks broken. The title fits. The comp works. 
On paper, everything makes sense.

But underneath? Pressure building.

What you're sitting on isn't burnout. It's stored energy. Years of pattern recognition. Decisions made under fire. Judgment earned through real stakes.

That's Career Capital.
And it's meant to compound.

When it's deployed, it creates leverage.
When it's trapped, it decays.

I've watched this happen to dozens of people. Smart. Capable. People who should feel satisfied. And they can't figure out what's wrong because nothing appears wrong.

Corporate is excellent at helping you build this energy.
It's terrible at knowing what to do once you have it.

So the pressure keeps building. 
Until it does one of three things:

→ Implodes into disengagement
→ Leaks as resentment 
→ Collapses into false stability

None of these are sustainable. 
They're just different forms of decay.

The people who break this pattern make a private decision:

"This energy will convert into something I own.
Because if I don't, it'll tear me apart."

That decision is binary.

Either you believe your current conditions can no longer use what you've built... or you keep waiting for permission that never comes.

Career Capital doesn't wait.
It compounds or it decays.

Which is happening to yours?

I paid for code with beer.
 
It was the only way.
 
I was awful at programming. Truly terrible.
 
But it was a forced part of my business degree. So I sat there in front of my computer, completely lost, feeling dumber than everyone around me.
 
The only solution? A case of beer for a few snippets of code from a friend who actually understood it.
 
That's how I survived.
 
Looking back, there were so few moments in school where I felt in flow. Most of it felt forced. Like I was wearing someone else's clothes.
 
Then I entered the corporate world thinking things would be different.
 
They weren't.
 
I remember sitting in a conference room on a Tuesday afternoon. Two hours into a meeting about optimizing a process that didn't need to exist. I watched my director passionately defend a framework nobody would use. And I realized: at least beer only cost me money. This was costing me my life.
 
That's when I started keeping a different kind of scorecard.
 
90% of what I was doing made me feel dead inside. Compliance for compliance's sake. Presentations to justify presentations. Work that looked impressive on paper but felt hollow in my chest.
 
That became my anti-vision.
 
But there was a 10% that lit me up...

Sketching frameworks on whiteboards and watching executives lean in. Helping burnt-out people realize they weren't broken, just miscast. Translating vision into language that made people feel something.
 
That 10% became my vision.
 
The kid who paid for code with beer grew up into someone who could rally teams and help people see what they were capable of. But I was doing it inside a container that would never let me go all the way.
 
So I built enough career capital to have a choice.
Then I made it.
 
But here's what nobody tells you:
 
You need the 90% to find the 10%. 
Your anti-vision clarifies your vision.
 
Most people experience the contrast and stop there. They know what they don't want. They can name it. They might even complain about it over drinks.
 
But knowing your anti-vision without acting on your actual vision? That's just comfortable misery.
 
The contrast is supposed to move you.

---
 
PS - Ever exchange beer for code? 
Or just me?

You spent 27 years building invaluable career capital.

But you can't access any of it.

Patterns only you can see.
Judgment built under real pressure.
A network that trusts your word.

All vaulted.
Uploaded to company cloud drives.

That's the Undeployed Career Capital Trap.

Your days get eaten by reactive work. Meetings about meetings. Fires that aren't yours. Permission loops that drain your best thinking before it sees daylight.

You've tried to use it outside work.
Consulting. Advising. Scattered posts.
That side project that fizzled into nothing.

But without the right sequence, every attempt leaks into generic traps. Billable hours. Execution without control. Work that looks like progress but builds nothing.

And the window is closing — you know it.

Here's what makes it worse:

AI is coming for the execution layer. The deliverables. The analysis. The "work."

What AI can't touch? Your pattern recognition. Your judgment. Your ability to see what others miss.

But that's exactly what's dying inside the trap.

Career capital either compounds or decays. Wait too long and it's not just missed opportunity. It disappears.

The signal I hear most:
"I know I'm sitting on gold. Why can't I deploy it?"

Because the trap is structural.

Fear keeps your best work locked up.
Reactive days steal your judgment hours.
Wrong sequence kills confidence before you start.

The path out requires creating conditions first. Reclaim your days. Release from the system thoughtfully. Build toward founder ownership.

This isn't an escape problem.
It's a deployment problem.

- - - 

PS - Here's where we're solving the Undeployed Career Capital Trap: https://lnkd.in/eDEkDVb2

Your career capital has a shelf life.

If you don’t claim it, it dies.

Most people assume experience compounds automatically and forever.

That once you’ve earned judgment, pattern recognition, and credibility, it stays available, waiting patiently for whenever you’re “ready.”

That’s not how it works.

Career Capital behaves like any other form of capital.

If it isn’t surfaced, packaged, and deployed while the window is open, it decays.

Corporate environments are very good at using your best thinking. They are terrible at helping you own it.

So the decay is quiet.

Your instincts sharpen, but only inside meetings.
Your judgment matures, but stays behind the logo.
Your leverage increases, but never sees daylight.

Over time, a dangerous gap opens.

You are highly capable.
And increasingly under-deployed.

Directors, VPs, and executives feel this most.

Not because they lack opportunity.
But because they’ve outgrown permissioned contribution and haven’t yet claimed authority.

The people who notice this early make a different move.

They don’t rush.
They don’t panic.
They don’t freelance their way out.

They slow down long enough to extract what they’ve actually earned.

They turn experience into language.
Judgment into frameworks.
Reputation into owned direction.

They understand one simple truth.

Capital that isn’t claimed gets spent by someone else.

That’s why I built The Career Capitalist™.

A one-time, live workshop for Directors, VPs, and execs who know they’re sitting on real leverage and refuse to let it expire unused.

This isn’t about quitting faster.
It’s about learning how to own what you already have before the window closes.

The Career Capitalist™
Private workshop + recording + working tools
Monday, January 19

Secure your spot: https://lnkd.in/esvq8nuY

This experience is built to create motion, not inspiration.

---

If this resonates, trust the signal.

Hidden Career Capital doesn’t unleash itself.
It gets claimed — or it withers.

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