Exited founder turned CEO-coach | Helping founders discover who they are as leaders and build high-performance, low-drama companies

Over 15 years I founded and served as CEO to three VC backed companies (one big exit and two learning experiences), all while presenting only the most polished, hyper-competent version of myself and my company, at all times. And then, in 2020 I left it all behind.When I signed the papers, officially removing myself as CEO of the company I’d started a decade prior, it felt like I’d been punched in the gut.Without my persona as the “CEO of VNN,” I realized that I had no idea who I was anymore, or what to do with my life.It was the opportunity of a lifetime.I spent the next 2 years searching, meditating, hanging out with monks, diving into psychedelics, and trying on new identities that never felt right.I was stuck.And then, I finally opened up.I started being honest about my struggles, despite the voice in my head telling me to play a role. I let go of my compulsion to be “Ryan the CEO,” or “Ryan the entrepreneur,” or even “Ryan the guy who’s raised a ton of money and scaled a media company.”I was just, Ryan.And the most surprising things happened.1. The more I opened up, the more everyone else did around me. My network grew and developed into one of deep relationships spanning life and business.2. The more I let go, the more the universe seemed to place exactly what I needed on my doorstep. Things began to happen organically, in ways much better than I could have planned.3. The quieter my mind got, the more I was able to access an innate wellspring of creativity and inspiration that, frankly, made work feel easy and joyful.Me, the guy who’d worked so hard his whole life to be perfect, when I learned to let go and be me, great, meaningful work flowed out of me.And from that foundation, I started Inside-Out Leadership, a boutique executive coaching firm that helps founders transform their companies into their masterpieces and step fully into their lives.Today, in my work as a coach I see the tendency to present that veneer of polished competence in nearly every founder I meet. And while I recognize the need for presentation in some cases (fundraising, recruiting), I also see how that need to look good actually gets in the way of our learning and growth.If you're tired of doing your own impression of the "perfect leader," you're not alone.Shoot me a DM. There's another way. And it's fucking incredible.

Ryan H. Vaughn

Early in my career, I was hesitant to be direct with people. I didn’t want to come across as aggressive. I didn’t want to hurt feelings. I didn’t want to be “that guy.”

So I softened feedback.
I talked around the point.
I hoped people would infer what I meant without me having to actually say it.

It sounded thoughtful.
It felt kind.
And it created more confusion than clarity.

For a long time, I told myself this was generosity. What I eventually saw was that it was mostly fear.

Indirect communication often gets framed as “niceness.” But more often, it’s a way of trying to preserve connection without risking discomfort.

And that’s the paradox.

The key to influence isn’t niceness. It also isn't directness. It’s connection.

Directness only works when it happens inside connection.

Leaders tend to go indirect in the moments that matter most:

Difficult feedback
Missed expectations
Tension that’s been quietly building

In those moments, indirectness becomes a crutch - a way to avoid the risk of saying something true and potentially disrupting the relationship.

But people feel it anyway.

They notice the mismatch between words and tone.
Between praise and body language.
Between what’s said publicly and what’s felt privately.

Standards get fuzzy.
Expectations get unclear.
And psychological safety starts to erode.

Because no one actually knows where they stand.

Or, equally problematic, leaders are overpowering in their directness. Crossing the line into asshole territory, and leaving no room for the other person in the interaction.

This is equally problematic, as it equally erodes connection.

Real influence happens when you can stay in connection and speak truth into that connection.

That requires self-trust.

Learning to communicate directly isn’t just a communication skill.
It’s a developmental shift.

It means trusting yourself enough to stay present when things feel uncomfortable.

To say what’s true without withdrawing or armoring up.
To risk momentary tension in service of long-term trust.

As that fear loosens, you learn to stay in connection with another human within more and more intense conversations. Then, something interesting happens.

Directness stops feeling harsh. It becomes clean. Simple. Human.

If experimenting with directness feels uncomfortable, that doesn’t mean you’re doing it wrong.

It takes practice. The key is in monitoring how connected you are with the other person, while you speak your truth.

That’s where influence lives.

---

Proud to coach with Inside-Out Leadership, CEO coaching by exited founders who've been there.

If this resonated and you want to dive deeper, shoot me a DM.

Exited founder turned CEO-coach | Helped early/mid stage startup founders raise over $500m, and create equity value over $12bn (and counting...)

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25 years building companies taught me that creating something meaningful is different than creating something successful.

Most people think meaning comes from getting somewhere.

A clearer vision. A bigger goal. A better version of themselves.

That belief creates tension.

Like a rubber band stretched tight between who you are today and who you think you’re supposed to become.

We praise that tension. We call it ambition.

And to be fair, it works.

It gets people out of bed. It builds companies. It produces results.

It also quietly guarantees dissatisfaction.

Because the moment you reach one version of the dream, it stops mattering.

It’s immediately replaced by the next one.

Not because you failed. But because the dream was never designed to end.

So the bargain most achievers make, usually without realizing it, looks like this:

Progress, momentum, recognition in exchange for contentment.

And we normalize this trade so completely that questioning it feels irresponsible.
Lazy, even.

Here’s what I've learned, working with dozens of founders in transition:

There are 2 fundamentally different ways to act.

1. Functional action

Doing things to get somewhere.
Action in service of an outcome.
Most work lives here.

2. Expressive action

Action taken not to become someone, but to faithfully respond to what’s true right now.

Not “What will this lead to?”
But “What feels honest in this moment?”

Expressive action doesn’t optimize for success.

It doesn’t guarantee status or promise outcomes.

It’s closer to art than strategy.

That scared me.

I worried that if I stopped chasing, I’d fall behind.

That everyone else would keep running while I stood still.

What I found instead was this:

When action comes from expression rather than ambition, there’s more energy, not less.

More precision. More aliveness.

You still work hard. But the work stops feeling like a toll paid on the way to a future life.

It is the life.

This is how you create something meaningful.

Not by aiming at meaning.

But by taking the action that feels most honest in this moment, without negotiating with outcomes.

Meaning is a byproduct of expressive action, never the goal.

This doesn’t mean ambition is wrong. Or that goals are bad.

It means if the only reason you’re moving is to escape the present moment, no amount of achievement will ever feel like arrival.

Meaning doesn’t come from becoming someone else.

It comes from doing what you’re doing as if it were art for its own sake, without needing it to justify your worth.

If this lands uncomfortably, nothing has gone wrong.

You may just be noticing that the ladder you’re climbing was never actually yours.

---

Proud to coach with Inside-Out Leadership, CEO coaching by exited founders who've been there.

If this resonated and you want to dive deeper, shoot me a DM.

Once upon a time, I won $500k from a five-minute business pitch, but I still think the business pitch, as currently constructed, is leading investors to fund the wrong entrepreneurs...

I have a friend. Immigrated from a war zone in Haiti with his family. Served in the military with distinction. After becoming a civilian, he founded multiple businesses, including a few aimed at helping vets. I have some high-capacity friends, but this particular friend is a force of nature.

I got to witness him pitch to a couple of angels & seed investors a while back. 

He told his story, explained what he was raising money for, but even as he was pitching, I found myself getting confused. The pitch didn’t follow the format I’m used to, and as a result, it wasn't as clear as it could have been. I noticed this, so I wasn’t surprised when the investors told him he was too early. 

These investors, who will tell you until they’re blue in the face that at the seed stage they bet on the jockey and not the horse, unceremoniously turned down a force of nature because his pitch didn’t match the pattern they’re looking for. 

And it got me wondering: is the investor pitch really the best way to make an investment decision at the seed stage? 

If it really is about the jockey, and not the horse, shouldn’t our attention be on learning about the jockey?

Now I get it. A good presentation at the seed stage is indicative of someone who will be able to give a good presentation at later stages. This is important.

But this is also a learned skill. 

There is a “right way” to present your business, which I or any other experienced fundraiser could teach a young entrepreneur in an afternoon. It’s glorified paint-by-numbers.

At the seed stage, having a great pitch is compelling. But however compelling it sounds, the business is wrong. 

It’ll change a ton of times between then and any sort of exit, so having a good pitch really only proves that you know the combination lock to get investors excited. 

Instead, we should be looking for someone who can create their own path when there is no clear way forward. 

What if, instead of focusing our diligence on the fundamentals of a business that will change umpteen times, we asked entrepreneurs to tell their stories? 
What if we tailored the process to finding the best jockeys, knowing that we can train them to pitch to later-stage investors as we go?

The best entrepreneurs, invariably, have incredible stories from their lives, school, the military, previous companies, etc. Stories of amazing resilience in which they've overcome incredible odds. Learning about how a person has navigated these environments in their past will tell us more about their ability to do those same things than asking them to make up pretty-sounding shit.

If what we’re really looking for at the seed stage is good people, shouldn’t we design our vetting process around figuring out who it is, really, that is pitching us?

I'd love to hear your thoughts below.

Somewhere along the way, many of us lose the ability to pretend.

We stop softening our words.
We stop managing the room.
We stop spending energy trying to be palatable.

What once felt automatic starts to feel exhausting. And then, quietly, it stops working.

This is not bitterness. And it is not a personality flaw.

There is actually some interesting science behind it.

I recently read an article by Ellen Scherr that explored how, as we age, the brain reorganizes itself. Neural pathways tied to constant social monitoring and emotional labor get pruned. Energy becomes more precious. And the brain becomes less invested in managing how we are perceived. 

In simple terms, we become less compelled to please.

The article talks about women in particular, but I see this shift in the men I work with all the time. Founders in their 40s and 50s become more direct. They people-please less. They stop contorting themselves to fit rooms they have already outgrown.

And almost without exception, life feels more intense: More alive, Less numb.

Usually, they often become more effective too, because they are no longer self-limiting just to fit in.

A lot of my clients come to me wanting to trust themselves more and show up as more thoroughly themselves, with fewer filters in their lives.

That transition matters.

When people let go of those filters, everything sharpens. And in our work, we help people get to know themselves deeply enough to trust what wants to come through.

But there's another way this happens: Age

I see it in most clients as they grow older. They care less about what they used to care about, especially socially. They become more direct. They give less fucks.

There are ways to accelerate that. Inner work is one of them. But age is a very reliable indicator. Think of your nana, farting loudly in the middle of dinner and completely ignoring it. It's that sort of thing.

Now, you may not want to go around farting everywhere.

But letting go of all the subtle ways you limit yourself to fit in is, in my experience, unquestionably a happiness and effectiveness amplifier. 

When you stop checking whether you're acceptable and adjusting yourself in real time, you stop outsourcing your authority to the room.

This is not about becoming careless or abrasive. There's a difference between authenticity and unintegrated impulse. It's about reclaiming parts of yourself that were kept hidden primarily to keep the peace.

Age will eventually take you there. Inner work can take you there sooner.

Either way, the destination is the same.

 A life that feels less managed. Less split. More honest.

If this feels familiar, nothing has gone wrong. You may just be growing into yourself.

And that is not something to fix.

-

Proud to coach with Inside-Out Leadership, CEO coaching by exited founders who've been there.

For most of my life, I had a very clear idea of who I was supposed to be. Then I discovered how to really live...

First, it was a professional basketball player.

I practiced constantly. Organized my life around it. Got the tattoos. I lived inside that identity.

And then that dream ended.

When it did, I didn’t stop to ask who I was without it.
I just found something else to become.

That next phase got darker. Drugs. Alcohol.
A few years of trying very hard not to feel the question underneath all of it.

Eventually, that identity collapsed too.
I ended up in jail after my second DUI.

So I did what a lot of people do at that point.

I decided to become someone better.

This was the late 2000s. Facebook and Twitter were just getting started. Startup founders were the new heroes. That seemed like a good thing to be.

So I became one.

I founded companies. Failed a couple times. Learned. Tried again. Built and scaled a venture-backed company over a decade. Raised money. Built a big team. Chased and eventually secured an exit.

And honestly, for a long time, it worked.

Until it didn’t.

A few years before I left that company, I started noticing how much energy it took to hold everything together.

Who I thought I needed to be for investors.
Who I thought I needed to be for employees.
Who I thought I needed to be for customers.

I was constantly managing the room. Constantly performing the role.

At some point, that just became unsustainable.

When I finally stepped away, a question landed that felt bigger than any business problem I’d ever faced:

If I’m not the CEO of this company anymore... who am I?

My reflex was the same one I’d always had.

Start something new.
Build the next thing.
Reconstruct the identity.

But this time, I didn’t.

Instead, I sat in the discomfort of not knowing.
No title. No pitch. No clean story about what was coming next.

People kept asking, “So what’s next?”

And for a long time, I genuinely didn’t know.

That was uncomfortable.
And humbling.

But something interesting happened in that space.

When I stopped trying to become anything, things started emerging on their own.

I started writing again. Not strategically. Just honestly.

That writing led to conversations.
Those conversations led to coaching.
And eventually, to the work I do now.

None of it came from a master plan.
It came from listening.

Entrepreneurship taught me how to build companies.

Letting go taught me how to build a life.

I see this pattern constantly in founders.

They think the next level requires a sharper identity.
A clearer vision.
A stronger version of themselves.

Sometimes the work is the opposite.

Not becoming someone new, but undoing the person you think you have to be.

If the old story isn’t working anymore, nothing has gone wrong.

You might just be standing at the edge of something more honest.

And that’s not a problem to solve.

It’s an invitation.

Most “shitty co-founder relationships” don’t start that way. Here's how they actually go off the rails: They decay slowly.

Every time something matters to you, but you don't say it, "eh, no biggie. I'll let it go."

You’re taking on relational debt. Cruft.

Imagine communication like a pipe.
Early on, it’s clean, you can say anything.

But over years of working together:

Missed expectations
Unspoken frustration
Feedback you meant to give, but didn’t

A little gunk builds up each time you don’t speak.

Eventually, the pipe clogs.

Now you’re arguing about trivial things, when the real issue is years of unsaid truth.

Here’s what I’ve learned from being a co-founder multiple times, and from coaching hundreds of founders:

Hyper-effective companies are built on hyper-effective relationships.

And hyper-effective relationships require clearing.

Clearing the pipe takes a simple (and very hard) 3-step process:

1) Observe what’s true, inarguably

Facts + your feelings.
No stories. No interpretations. No blame.

2) Take 100% responsibility

Not because it’s all your fault but because ownership is the only place you can create change.

3) Commit to doing your part differently

Your commitments are the antidote to the environment you helped create.

Notice what’s missing?

No demand for an apology.
No score-keeping.
No forcing the other person to change.

When you fully own your side, one of two things happens:

• The relationship becomes clean and effective again
• Or it becomes obvious it can’t continue, without drama

Either way, the pipe is clear.

And clear communication is the foundation for whatever you build next.

If you're struggling with your cofounder relationship, comment "gimme gimme" to get the full, comprehensive strategy we share with clients.

---

Proud to coach with Inside-Out Leadership, CEO coaching by exited founders who've been there.

If this resonated and you want to dive deeper, shoot me a DM.

Jim Carrey stood on the Golden Globes stage, a two-time winner, looking out at a room full of the most successful people on earth. What he said next is a valuable lesson to us all: 

“I am two-time Golden Globe winner Jim Carrey...
And when I dream, I don’t just dream any old dreams. No sir. I dream about being three-time Golden Globe winner Jim Carrey. 
Because then I would be enough. 
It would finally be true. 
And I could stop this, this terrible search. 
For what I know, ultimately won’t fulfil me.”

He was joking, but at the same time, he definitely wasn't.

This is the sacred, self-inflicted wound that drives every high-achiever.

It starts with a dream. And with the first whisps of the dream, the machine locks in, and the outcome is set.

You create details, bringing the dream to life. And the minute it's real, a tension is born: a taut rubber band stretching between the dream and you. 

The dream is always pulling. 

You feel this tension as the disappointing, unself-actualized side of yourself, which compels you to chase, to change today to conform to your vision for tomorrow. This tension propels you out of bed every day.

We deify this tension as ambition. We call it "making something of yourself." But in addition to propelling us, it permeates life with a generalized dissatisfaction that no amount of achievement can solve. The moment you attain a piece of your dream, it becomes irrelevant, overwhelmed by the necessity of attaining the next piece. If you attain the whole thing, your dream will have receded, sitting as far out of reach from your hard-won perch as it was at the start.

The bargain is this: to succeed in getting closer to my dream, I offer in trade my contentment, in full, and vow to never be satisfied. 

This is the trade many high-achievers make. They get the allure of the chase at the cost of the moment.

Chasing a dream translates roughly to "wishing things were different from what they are." Since they cannot possibly be, our perpetually unfulfilled wishes leave us wanting. The game of chasing an ever-receding mirage is a game you can't win. 

I see this most often with founders right after an exit, to whom I say:

If you can still convince yourself that building a bigger company will finally make you feel complete - considering the last exit didn't - then do it. It is by far the easier path. 

It’s just like Jim Carrey's "dream" of a third Golden Globe. 

But eventually, you realize that no exit is big enough to make you feel whole in a lasting way. 

That is the moment the real work begins. The work that leads you away from chasing achievements to feel complete, and into the actual work of your life.

That transition - from performer to person - is the most exciting part of what I do.

It’s when you finally stop searching. And start living.

---

Proud to coach with Inside-Out Leadership, CEO coaching by exited founders who've been there.

Most companies that implode, do so for the same reason.

I still remember the chair I was sitting in.

Brown leather. Boardroom.
Nine months after our Series A.

We were scaling fast, from 15 to 75 people.
Hitting numbers. Lining up a Series B.

An investor looked at the pitch deck I’d spent weeks on and said:

“This is garbage. No one will buy this. Change it.”

In that moment, my job as CEO was to push back. I knew that.

Instead, something else happened. Fear took over.

And it almost killed the company.

A wave hit my body first, heat in my chest, pressure, shame.
And suddenly I wasn’t a CEO in a boardroom anymore.

I was a kid, scared that if I didn’t comply, someone would leave.

So I did what fear told me to do. I changed the pitch.

The raise failed.
We closed a bridge round instead.
It took years to recover.

At the time, I told myself a clean story: bad advice, bad board dynamics, bad timing.

What I couldn’t see yet was the real cause.

Fear made the decision for me.

This is far more common in startups than we like to admit.

We rarely talk about fear directly. So it hides behind more respectable labels:

Perfectionism
Founder conflict
Execution issues
Being “off your game”
Tone problems

Different symptoms. Same root.

Fear is a reflex. And when it’s unexamined, it runs companies from the background.

I see this constantly now in founders I work with:

• Flinching in negotiations
• Avoiding hard conversations
• Over-polishing instead of shipping
• Defensiveness
• Burnout

All fear-based. Mostly unconscious.

So what actually helps?

1. See fear as a bodily experience, not a thought.
Fear shows up as sensation before it becomes story.

2. Name it directly.
Not “I’m off my game.” But “I’m scared right now.”

3. Wait to make important decisions until fear has subsided.

The ability to sit with discomfort until you can respond instead of react is a leadership skill.

And finally: talk about fear as fear. Unexamined fear becomes fate.

For founders, this isn’t optional inner work.

It’s a business risk.

Ignoring fear and hoping it goes away isn’t an acceptable strategy for technical debt or competition.

It shouldn’t be for leadership either.

---

Proud to coach with Inside-Out Leadership, CEO coaching by exited founders who've been there.

If this resonated and you want to dive deeper, shoot me a DM.

Anxiety is the price of the life you were meant to live. James Hollis said that years ago, and I’ve found it to be painfully accurate.

If you’re building something new, stretching beyond who you’ve been, anxiety is inevitable. 

Not as a flaw. As a signal.

Most people treat anxiety like an enemy. Something to suppress, outrun, or eliminate. And when that doesn’t work, they assume something is wrong with them.

Usually, nothing is wrong.

Anxiety is your nervous system doing its job. It’s an alarm designed to pull your attention toward something that matters.

The problem isn’t anxiety. It’s our relationship to it.

When you resist anxiety, it tightens.
When you try to override it with logic, it gets louder.
When you numb it, you mute everything else too.

What actually helps is learning to interpret it.

Some anxiety is functional. It’s telling you to act. Make the call. Fix the problem. Adjust the plan. Once you do, it quiets down. Feature, not bug.

Other anxiety is patterned. Old. Installed early. Designed to protect you from hurts that are no longer present. That kind of anxiety doesn’t resolve through action. It resolves through feeling it fully. Listening to it all the way, until it has nothing more to say.

That’s the part most people avoid.

Because feeling anxiety fully takes courage. It requires slowing down instead of muscling through. Listening instead of fixing. Trusting that the emotion isn’t here to destroy you, but to show you something.

When you learn to work with anxiety this way, it stops running your life from the background. It becomes guidance instead of interference.

The irony is that the leaders who feel the most alive, most grounded, most effective aren’t the ones without anxiety.

They’re the ones who stopped fighting it.

---

Proud to coach with Inside-Out Leadership , CEO coaching by exited founders who've been there.

If this resonated and you want to dive deeper, shoot me a DM.

For most of my life, I thought happiness lived in peak experiences.

The big win. The next milestone. The moment where everything finally clicked.

So I chased them.

In business. In relationships. In sports. In life.

And I got a lot of them.

Enough, eventually, to notice something uncomfortable:

no matter how hard-won or impressive the achievement, the feeling at the end was almost always underwhelming.

Brief. Fading. Never quite what I’d imagined.

I could still see how the chase worked. How it motivated me. How it produced results people admired.

But I could no longer convince myself that the next gold star would bring anything lasting.

What’s surprised me most over the last few years is discovering a different source of happiness altogether.

Not from attaining something. But from paying attention.

Through consistent practice, I’ve learned to give full, singular attention to the present moment, not just what I see or hear, but the whole thing: sensations, sounds, thoughts, everything happening right now.

What that unlocked wasn’t excitement or adrenaline.

It was something quieter.

Contentment.
Gratitude.
A sense of awe that doesn’t depend on circumstances.

And here’s the paradox.

The fastest way I’ve found to lose that feeling... is to chase it.

Trying to pay attention in order to get somewhere defeats the point.
Trying to become something pulls you out of where you already are.

Real attention only happens when you stop trying to improve the moment and simply let it be.

For a long time, I lived the version of success our culture rewards: sacrifice now, work harder, accumulate achievements and experiences, and enjoy them later.

I played that game well.

But it wasn’t until I stopped chasing that I noticed something unexpected.

The quiet beauty of an ordinary tree on the side of the road.

And the realization that it had been there all along.

In 2014, Microsoft was stagnant after years of success. Then, Satya Nadella took over and did the opposite of what most CEOs do: he didn’t start with strategy, he started with psychology...

For years the stock essentially wouldn’t move.
Key markets, like mobile and early cloud were slipping away.
Internally, teams were siloed.
Competition inside the business was rewarded more than collaboration.

The company wasn’t dying, it was stagnating.

Most leadership plays at moments like this start with strategy:

New products. New org charts. New KPIs.

Nadella’s first move was quieter and much harder.

He called out the real problem:

Microsoft had become a “know-it-all” culture and needed to become a “learn-it-all” one.

That feels soft, but it isn’t.

A know-it-all culture is driven by fear:

• Fear of being wrong
• Fear of losing status
• Fear of admitting uncertainty

That fear doesn’t show up as panic. It shows up as silos.

Avoiding hard conversations.
People optimizing for brilliance over learning.

That wasn’t a strategy problem. It was a psychology problem.

So he started inside.

He modeled curiosity instead of certainty.
He rewarded leaders who learned and collaborated.
He made it safe to say “I don’t know” and ask better questions.

He didn’t just change culture, he changed how leadership worked.

The result?

Microsoft regained relevance.
Cloud became a core growth engine.
And the company went from a decade of stagnation to becoming one of the most valuable companies in the world.

But that’s not the real lesson.

Leadership breakdowns rarely start as strategy problems. They start as fear-driven behavior patterns.

Fear doesn’t announce itself as fear.
It shows up as:

“We need more certainty.”
“That’s not how we’ve always done it.”
“We’re right and they’re wrong.”

Those aren’t causes.
They’re symptoms.

Nadella began with the psychology under the surface:

• how people relate to uncertainty,
• how they protect identity,
• how they choose learning over armor.

Most leaders try to fix outcomes.

The best fix themselves first.

That’s where real transformation begins.

---

Proud to coach with Inside-Out Leadership, CEO coaching by exited founders who've been there.

If this resonated and you want to dive deeper, shoot me a DM.

Step 7, The Postcard: The primary risk to any intentional change is inertia. Specifically, that your best intentions get lost within the never-ending sea of life/work/family tasks, and before you know it, another year has passed... 

Don’t let that happen.

Create accountability for yourself, to yourself, by writing a letter to your future self, which you’ll schedule to have automatically delivered at a future date.

This way, whatever happens in the year ahead, you know that at some point in the future you will be reminded of your commitments, and have occasion to reflect on how well you kept to them (remembering that the key is keeping to actions taken, not outcomes produced).

In this letter, share your reflections from these exercises, your learnings, and any commitments you are making to yourself.

Schedule the email to send to yourself on June 30, 2026, using your mail client’s “Schedule Message” feature. 

And with that, brings the close to my annual reflection template.

------------

This is it.
This year.
This minute. 
This moment.

Even if it seems like this couldn’t possibly be it. 

That feeling is it, too.

Thank you for everything you brought to the world in 2025, for everything you are, and for everything you are becoming. 

Thank you for taking the time to reflect on your one weird, precious life, and by doing so giving yourself the opportunity to create it more consciously. 

Thank you for being unabashedly you, and not anyone else.

There will be a lot of moments in 2026. Co-create them with the ones you love.

I wish you the best of luck in diving deep, leading authentically, and bringing your unique story to the world this coming year.

And, if you'd like access to the full Annual Reflection Template, comment "Gimme gimme" below.

---

Proud to coach with Inside-Out Leadership, CEO coaching by exited founders who've been there.

If this resonated and you want to dive deeper, shoot me a DM.

I had to die three times before I finally got the hang of it.

The first was at 17.

I was convinced I’d be a professional basketball player. I practiced constantly. Built my life around it. That identity gave everything meaning.

And then it ended.

I didn’t know who I was without it, and I wasn’t willing to stay with that question.
So I numbed it.

Drugs. Alcohol. A few years of running hard in the wrong direction, until I found myself sitting on a stiff cot in a jail cell after my second DUI.

That version of me collapsed completely.

The second time, I responded the way our culture teaches us to.

I decided I could still be great, just as someone else.

This was the late 2000s. Startup founders were the new heroes. That felt like a worthy thing to become.

So I became one.

I founded companies. Failed a couple. Learned. Tried again. Built and scaled a venture-backed company over a decade. Raised capital. Built a large team. Eventually exited.

For a long time, that identity worked.

Until it didn’t.

When I finally stepped away from the CEO role, that identity died too.

But this third time was different.

Every other time an identity fell apart, I rushed to replace it.
New role. New story. New certainty to keep myself moving forward.

This time, I didn’t do that.

Instead, I stayed in what followed.

No title.
No plan.
No clean answer when people asked what was next.

It felt like standing on a plateau, between where I’d come from and wherever I might go next. The old story was gone. The new one hadn’t arrived.

A liminal space.

In the past, I treated moments like this as problems to solve.
Something to fix as quickly as possible.

This time, I let it be unfinished.

That space was uncomfortable. Disorienting. Quiet.
And unexpectedly, it was also the most alive I’d felt in years.

Without an identity to perform or defend, I started noticing what actually had energy. Writing. Honest conversations. Work that emerged instead of being forced.

Not from a master plan.
From listening.

Every major transition creates this in-between moment, when who you were no longer works, and who you’ll become isn’t clear yet.

Most of us rush to close that gap.

But there’s another way through it.

Not by recreating yourself.
Not by rushing to certainty.
But by staying with the space long enough for something truer to surface.

That’s what the third death taught me.

Not how to become someone new.

But how to stop interrupting the moment where life is trying to show you who you already are.

---

Proud to coach with Inside-Out Leadership, CEO coaching by exited founders who've been there.

If this resonated and you want to dive deeper, shoot me a DM.

There’s a moment in leadership that doesn’t get talked about much - when the role that once fit you perfectly starts to feel heavy.

Not wrong.
Not broken.
Just no longer yours.

Most people interpret that feeling as something to fix. 

Recommit. Push harder. Find the motivation again. 

After all, this role worked once. It made you who you are.

But sometimes what’s happening is simpler, and harder to accept.

You’ve changed.

Most leaders don’t leave roles because they fail at them. They leave because, quietly, the role no longer matches the person they’re becoming.

Howard Schultz is a useful example of this.

He built Starbucks. For a long time, he was Starbucks. The company’s culture and story were deeply personal to him. When he first stepped away as CEO, it wasn’t because the company was broken. It was because the role no longer fit.

Years later, he returned. The company needed him, and at that moment, he was the right person again.

And then, later still, he stepped away once more.

That second departure is the interesting one.

It wasn’t driven by crisis or failure. It came from something quieter. A recognition that staying would mean clinging to a version of himself that no longer felt true.

Most founders struggle here.

They stay in roles long after they’ve outgrown them, not because they’re incapable, but because their identity hasn’t caught up. The company becomes a proxy for self-worth. Letting go feels like disappearing.

But outgrowing a role isn’t failure.

It’s information.

It’s a signal that the work is changing, and so are you.

I see this often in my work. Leaders who are still performing competence long after it stopped being authentic. They’re not failing. They’re misaligned. And the longer they ignore that signal, the more brittle everything becomes.

Stepping away, when done honestly, isn’t quitting. It’s a form of stewardship. Of yourself, and often of the organization too.

The hardest part is trusting that who you are is bigger than the role that once defined you.

But that trust is exactly what makes the next chapter possible.

---

Proud to coach with Inside-Out Leadership, CEO coaching by exited founders who've been there.

Michael Phelps won 28 Olympic medals across four Games. Yet, after London 2012, despite winning six medals, he was in deep crisis and contemplated ending his life...

He's not alone. Will Smith has talked about "Cliff Top" being just as lonely and hard as "Rock Bottom." Jim Carrey has said similar. The list goes on.

So what's going on?

This is a central paradox of high performers in any field. The fierce drive that propels you to the top of your game/market is the same corrosive force that leaves you hollowed out at the summit. For founders, we chase the exit unquestioningly, so focused on attaining the goal that we never stop to consider what might come after.

What nobody tells you about an exit is that the leaving is its own special kind of challenge. Special, and yet surprisingly consistent from person to person.

Here's the typical process:
1. Exit.
2. Existential vacuum.
3. ???
4. Realigned to purpose.

Some founders, confronted with this vacuum of purpose, jump immediately into the next thing. If you exit your consumer app and can find purpose in an even bigger consumer app, bless your heart, please run with everything you've got. Come read this post back after your next exit. 

If you find yourself struggling, however, know that you're not alone. Many founders struggle with step 3. I did. I experimented, jumping into each project with the same gusto, but I kept finding that I couldn’t recapture that sense of unquestioning purpose. Try as I might, it just felt different.

The salient issue, I've learned after coaching dozens of founders through their post-exit transition, is that as we mature, the way we construct meaning changes. 

At first, we FIND purpose. But eventually, we must CREATE it.

Finding Purpose:

• Purpose is found in the world and brought into yourself.
• Meaning is derived from what, and how much, you get.
• Success is a function of the outcome achieved.

Creating Purpose:

• Purpose is found inside yourself and brought to the world. 
• Meaning is built from what, and how much, you give.
• Success is a function of the work done and the motivations behind it.

Phelps found his breakthrough by checking into intensive treatment in 2014.

He returned in 2016 to win five more golds in Rio, but he swam from a radically different internal foundation. He swam from love for the sport, not the desperate need for meaning. The achievement was the same, but his entire relationship to it had transformed.

Today, he has moved beyond the pool to create purpose as a vocal advocate for mental health. By sharing his struggle, he is building a meaningful life that a gold medal alone never could.

Only you can tell if it's time to start your own work. If so, here's a question for you to get started on your path to rediscovery:
 
How can your career be most useful to others?

In 2017, Uber lost its CEO, its reputation, and nearly its future - because the culture became toxic and turned against itself. I’ve been there, too, without the global brand, but with all the danger...

Uber's early success was fueled by aggression, speed, and internal competitiveness. These traits fueled their rise, but without emotional regulation or boundaries, they became catastrophic liabilities.

I've been in that pressure cooker.

Years ago, I scaled my company from 15 employees to 75 employees in nine months. Our corporate culture was completely unprepared for the stresses of such rapid scale-up.

I talk to founders every day who face the same dilemma. They do what successful people do: they try to fix it. They spend a fortune on consultants, off-sites, and "culture work."

Uber is the masterclass in this.

They hired a former U.S. Attorney General to write a 12-page report with recommendations, fired 20 people in one shot to signal 'change', and ditched their original values for a new list of corporate-approved principles.

But you can't fire or spend your way into a new culture. By pushing new cultural frames without acknowledging the current ones, you breed resentment and cynicism from those who see the culture for what it actually is.

To truly change your culture, first, you must stop trying to build the culture you want and start by looking at the culture you actually have. Only then, working from a foundation of what is, can you begin to make change.

Here's how:

1. Look Inside Your Company

Anonymous surveys are a great tool to understand how your employees view your culture. Anonymity is key.

A survey like this communicates to your employees that you understand the importance of culture and that you will presumably listen to what they say. However, if you take this route and do nothing to address the feedback, it can break trust. 

2. Look Inside Yourself

At some point in every entrepreneur’s journey, they realize that their company is a manifestation of themselves. This offers a shortcut: you can understand your corporate culture by understanding yourself.

Are you late to meetings? That’s your culture. Others are late, too. 
Do you hold yourself to the grindstone, sacrificing holidays to make more progress? That’s your culture. Others do that, too. 

While most entrepreneurs resist this, looking internally is the most reliable route to determine your culture. For those brave few, it’s best done with either a 360-degree survey, or a dedicated coach to help you see your blind spots.

Great. I’ve reconciled with my current culture, and I still don't like it. Now what?

Once you've identified how you're creating the culture you say you don't want, changing it is simple:

Step 1: Change yourself to live by the values you want the company to live by.
Step 2: Write the values you live by on the wall.

And if you’re wondering, yes, that’s what we actually did to transform our culture at speed.

Simple, yes.

But not easy.

I used to be a virtuoso of the "Founder's Glance." In 30 minutes, I could diagnose a hemorrhaging sales pipeline or a toxic board member with surgical precision. It took me 15 years to sharpen these instincts into a blade...

And then GPT-4 learned it all in an afternoon. 

For the modern founder, watching AI automate your "unique" expertise is far more than merely a professional crisis. It’s an existential punch to the gut. 

The standard advice is to pivot - to move from "knowledge" to "wisdom." We’re told that our value now lies in judgment, in knowing which fires to douse and which to let burn. There is some truth there, certainly. 

But here is the deeper rot that no one wants to name. 

Tying your worth to "wisdom" is just as brittle as tying it to knowledge. Because wisdom is still something you possess. It is an accumulation, a trophy case of experiences. And anything you possess can - eventually, inevitably - be taken from you. 

I grokked this the hard way in 2020. 

The day I signed the papers and officially ceased to be "Ryan the CEO," the armor evaporated. Without the title, the expertise, and the authority, I realized with a terrifying clarity that I had no idea who was left standing in the room. I had spent a decade building a masterpiece of a company, but I was a stranger to the person underneath it. 

The only foundation that cannot be automated is your Integrity. 

Not integrity as a corporate buzzword, but integrity as wholeness - the radical alignment between your deepest values and your daily actions. This requires two things that are infinitely harder than raising a Series A: 

1. Ruthless Self-Inquiry: 

Stripping away the inherited scripts of "unicorn status" and "disruptive growth" to find what you actually give a damn about when the world isn't watching. 

2. The Courage to Lose: 

The terrifying bravery to say "no" to the high-status investor or the lucrative exit because it doesn't match the shape of your soul. 

When I finally put down the Successful CEO costume, the world didn't end. 

It began. 

And I became a more integrated human being. 

Inside-Out Leadership was born from that wreck. We help founders find the floor that doesn't drop out when the technology changes. 

If you’re tired of being at war with an algorithm for your sense of worth, let’s talk. 

Shoot me a DM. There's another way.

I’m the founder and co-CEO of Pragmatico, an AI cultural transformation company. 

I serve as a Fractional Chief AI Officer for organizations like Prime Hospitality Group and Audiochuck (creator of Crime Junkie),  where we grew AI adoption from 12% intermittent use to 95% skilled, active usage.

Building world-class teams that solve real business problems is what gets me out of bed in the morning. 

I'm also a 3x-exited founder and executive coach. I’ve spent the last decade helping hundreds of leaders transform their cultures through data-driven insights and coaching. I co-founded Emplify, an employee engagement measurement company, which was acquired by 15Five in 2021. I started my executive coaching practice shortly thereafter. 

On the personal side, I’m a proud Colombian immigrant, drummer, hot yoga enthusiast, and world traveler (40 countries and counting). 

Here on LinkedIn, I write about:

- The human aspects of AI transformation
- How to lead well without losing yourself
- Lessons learned from my own entrepreneurial and leadership journey

Other awards and accomplishments include:

- Amazon best-selling author of “Agile Engagement”
- Indiana Latino Businessman of the Year 
- Indianapolis Business Journal 40 Under 40 
- Inc. Magazine's 30 Under 30 
Whitehouse.gov "Champion of Change"

Santiago Jaramillo

Pragmatico has a new Head of Sales, and I’m thrilled to share that it’s John Gotsis! 

I’ve known John for 16 years. He’s a deeply authentic, high-integrity human and seller.

John is joining Pragmatico after crushing it at Conga for three years. He was Strategic AE of the Year for 2025, hitting a massive 205% of quota. 

At Authenticx, he built the entire Sales Development function from scratch as employee #25. Generated $8.2M in pipeline in 10 months.

The best part: I’ve witnessed John in action. He joined Emplify as an SDR in 2019, and by 2021, he was leading the team and setting company records for outbound meetings booked.

And John already knows AI. 

At Conga, he drove digital transformation with automation and AI-aligned tools. 

At his most recent role at ConnexAI, he closed enterprise deals for conversational and agentic AI platforms.

When you're building a company, you want people who've proven they can sell while having fun along the way.

John is that guy.

Welcome to the team, John. Let's do this.

Santiago (Santi) Jaramillo

Founder, Co-CEO & AI Transformation Lead (3X Exited CEO & Founder)

As we forge ahead into 2026, I’d like to reintroduce myself to the newer faces in my network and touch base with those who’ve been along for the ride.

Entrepreneurship has always been my “art form,” ever since I sold water to neighbors out of a red Radio Flyer wagon at age 7. 

At age 10, I was almost kidnapped in my hometown of Cali, Colombia, and moved to the US shortly after.

I spent 2011-2021 founding, growing and selling venture-funded tech companies. 

My last venture, Emplify, focused on helping companies build measurably healthier cultures. Sold it to 15Five in 2021.

I needed a break from the intensity of building companies, so I transitioned into executive coaching to help leaders work through their growth areas and blindspots.

Then ChatGPT dropped.

As I experimented with AI for my coaching practice, the entrepreneur in me woke up. 

So I co-founded Pragmatico in 2024 as a side hustle. I billed it as an AI education and upskilling firm. Led workshops to teach senior leaders how to use AI.

It didn’t work. 

People loved our training. But their companies and cultures didn't actually transform.

Turns out AI adoption is a cultural problem, not an educational one.

So today, I’m back in founder mode after pivoting Pragmatico. We're building systematic programs that embed AI adoption into organizational DNA, not just teaching skills. 

I worked with Audiochuck (creator of the Crime Junkie podcast) as a fractional Chief AI Officer, where we grew AI adoption from 12% intermittent use to 95% skilled, active usage.

On the personal side, I’m running experiments in 2026 about where to live. 

Randy Stocklin and I co-founded Pragmatico to be remote-first, which lets me split time between the U.S. and Latin America to reconnect with my roots and first language.

On weekends, you'll find me doing hot yoga, spending time with my cat, Pippa, and/or attempting a perfect sear on a ribeye steak. 

Thanks for following along on my journey.

undefined undefined

Thought Leadership Consultant, Publicist, and LinkedIn Trainer

I am an Indianapolis-based freelance publicist and LinkedIn thought leadership consultant specializing in B2B industries like HR, tech, and professional services. 

I love helping business leaders leverage social and traditional media to build credibility and grow their audiences. My thought leadership ghostwriting has appeared in publications like Fast Company, Forbes, Inc., and Entrepreneur, but of course, you wouldn’t know it from the bylines. On the public relations side, I drive strategy and execution to deliver top-tier, trade, and local media coverage for clients every month. I've led media strategy for venture capital funding announcements, company acquisitions, data reports, product launches, and more. 

As a result of my efforts, my clients have been featured in publications like Axios, Business Insider, CIO, FastCo, Forbes, Inc., The Indianapolis Business Journal, HuffPost, TechRepublic, Vanity Fair, and VentureBeat.

Pragmatico

Co-Founder & Co-CEO at Pragmatico

Elon Musk got caught off guard at an all-hands meeting.

He was showing off the Optimus robot, talking about its capabilities.

An employee asked: "What does this mean for my job?"

He wasn't ready.

You could see it.

And if ELON wasn't ready for that question, 90% of CEOs definitely aren't.

And your employees ARE asking the question.

Maybe not out loud.

But definitely in their heads.

Every time you mention AI and celebrate a process being automated, they're wondering if their job is on the line.

Here's what most leaders miss:

You think you're talking about innovation. They think you're talking about layoffs.

Until you explicitly address this fear, everything you say about AI gets filtered through it.

"We're implementing AI" becomes "They're replacing us."

"This will make you more productive" becomes "They want to do more with less of us."

"Exciting AI opportunity" becomes "Start polishing your resume."

The companies getting AI adoption right have one thing in common:

They intentionally answer the Elon question BEFORE anyone asks it.

I believe ChatGPT Deep Research is the most powerful learning tool invented since the Internet.

Here's what I watched yesterday:

An executive typed, "What are the best practices for improving consultant utilization rates at mid-size professional services firms, including specific scoping frameworks and client communication approaches that reduce write-offs at top-performing consultancies?"

Then he walked away for 10 minutes.

ChatGPT searched 50+ sources. Read academic papers. Analyzed industry reports. Synthesized frameworks from firms with best-in-class realization rates.

When he came back: a comprehensive research report that would've taken a team of analysts a week to compile.

Not a quick answer. A complete investigation.

It's like having PhD researchers in your pocket who work for free while you're in another meeting.

If you're not doing at least one Deep Research per week, you're learning slower than you could be.

The future belongs to the learners. And this is the learning accelerator.

How to try it:
👉🏽 ChatGPT: Click the "Deep research" button below the prompt box (requires Plus/Pro)
👉🏽 Claude: Type your question, then click "Research" above the input field

What's a complex question you've been avoiding because the research felt too heavy?

My biggest takeaway from 10+ years as a CEO and coaching 50+ CEOs: 

The central importance of high-talent-density teams. ESPECIALLY early on.

To kick off our rapid team expansion, I’m excited to share that Michael Vasey is joining Pragmatico as our AI Transformation Lead. 🎉🎉

Michael built Emplify's employee engagement services model from scratch and coached 200+ CEOs and HR leaders as they navigated culture change.

The skills that make Michael exceptional are exactly what Pragmatico clients need for AI transformation:
- Building executive trust
- Guiding senior leaders through proven change management playbooks
- Coaching through resistance
- Measuring behavior change over time

If you're a mid-market company trying to figure out how to make AI adoption stick and yield results, you're going to want to work with Michael.

Welcome aboard!

Consultative executive influencer driven to provide AI growth and value

I just looked at usage analytics for 50 executives we trained on AI. The split was dramatic.

Top user: 202 messages in 30 days. 
Bottom 5: Logged in twice. Never came back.

Same company. Same training. Same tools.

Here's what nobody wants to admit:

The leaders regularly using AI aren't smarter or more "tech-savvy." 

They made one decision that the others didn't: 

They decided to feel stupid for 30 days.

That's it. 

They pushed through the awkward phase where AI gives you garbage outputs because you don't know how to prompt it yet. 

The others hit that wall and quit.

Being bad at something new is the price of admission for future mastery. 

What could you build, create, or solve if you gave yourself permission to be a beginner for 30 days?

One of my favorite Pragmatico core values: Get Speeding Tickets, Not Parking Tickets

Translation: You have permission to ship before it's perfect.

Many leaders I’ve worked with are a little too careful. They optimize for zero mistakes instead of maximum learning. 

But I believe the cost of delay exceeds the cost of mistakes. If you're not occasionally making mistakes from moving too fast, you're moving too slow.

This doesn't mean reckless. 

It means:
👉🏽 Ship the MVP and iterate
👉🏽 Get real user feedback over internal opinions
👉🏽 Fix mistakes quickly instead of preventing all mistakes forever

Learn by doing, not by planning

Done today beats perfect next month.

If you're an experienced content marketer who's looking for a role where strategic thinking meets hands-on execution, and where your work actually shapes how an industry thinks… 

This is it.

👇🏽

https://lnkd.in/eHCnvgYG

CMO at Docebo | Advisor | Dad x2 | Author x3

My friends at Pragmatico are hiring a Head of Content Marketing, and it's a super interesting role. 

Outside of working with Randy Stocklin and Santiago (Santi) Jaramillo (which should be enough), this is a super interesting role because it's more than just writing and managing. 

It's about building the content engine for a company helping mid-market organizations actually adopt AI. ADOPT IT! Not just sign up for an account. 😎 

Newsletter, podcast, founder thought leadership, customer stories, sales enablement, and AI-powered systems that turn real client work into media.

You’ll work directly with the co-founder, shape the voice of the company, and help define what “AI transformation” really means in practice.

Fully remote. Early-stage, but already cash-flow positive. Strong founders. Clear point of view. If you’re a senior content leader who likes strategy and execution, this is worth a look.

👉 Pragmatico.ai/careers

Most leaders think rolling out ChatGPT + live training will stretch their already-maxed-out teams.

Here’s why that’s backward.

Last week, I sat across Zoom from two founders running at 100% capacity. 

Team across time zones, crushing client work, about to implement a reorg. 

When I suggested adding AI transformation to their roadmap, I watched them mentally calculate: "We're already at 100%. This puts us at 150%."

Here's what I told them that shifted everything:

The math isn't 100% + AI = 150%. It's 100% + AI = 85% with more output.

For one client, after a 90-minute Level 1 AI training, people reported saving 3-4 hours that same week. By Level 3, they're reclaiming 7-10 hours weekly. 

Their team isn't working more. They're working smarter, on higher-order tasks, while delivering more.

Are you waiting for capacity you'll never have, or are you creating it?

The answer to this question is the best diagnostic for your team’s AI readiness:

"What do you think will happen if you get really good at AI?"

Why this question works:

Your team is having the AI conversation in their heads, whether you're having it with them or not.

This question brings it out into the open and exposes the fear hiding underneath the surface.

Here's how to read the results:

👉🏽 If they say: "I keep my job."
You're trouble.
This means your team believes competence = survival.
They think the goal is to avoid being fired, not to grow.
When people are in survival mode, they don't experiment. They hide. They do the minimum required and keep their heads down.
You'll never get adoption from people who see AI as a threat assessment.

👉🏽 If they say: "The company wins" or "We can grow faster."
Stop. Probe deeper.
This answer is often a deflection.
When someone gives you the "company answer" without mentioning themselves, they're usually hiding their real fear.
Ask the follow-up: "Yes, but what does that mean for YOU personally?"
If they can't articulate their own benefit, they're not actually on board.

👉🏽 If they say: "I don't know" or "I'm not sure."
You have a communication problem.
They haven't connected AI to any outcome, good or bad.
Which means all your messaging about AI transformation is landing as abstract corporate-speak.
They're confused, not inspired.

👉🏽 If they say: "I get promoted" or "I become more valuable and future-proofed."
You're on the right track.
This means they see AI as a tool for advancement.
They believe learning AI will make them more capable, more impactful, more promotable.
These are the people who will experiment, share use cases, and drive adoption.

Most companies talk about AI adoption as a training problem.

It's not.

It's a trust problem.

Employees want to know: "Is this tool here to help me or replace me?"

Until you resolve the fear, all the training in the world won't drive adoption.

This is the loneliest sentence in leadership right now:

"I'm trying to figure out AI in my spare time."

This, from a leader I talked to last week running a 30+ person agency AND managing client work. 

Yet somehow, she’s supposed to become an AI expert between meetings.

I’ve felt that pain.

As a young founder, I spent 10 years believing I had to personally solve every problem.

It eventually burned me out.

And I’ve watched countless founders struggle with the same thing.

But here's the truth:

Your job isn't to figure everything out alone.

It’s to know what to delegate and when to bring in guides.

Not because you can't figure it out yourself, but because your time and energy is worth more elsewhere.

What are you trying to solve alone that you should be delegating?

This is the one AI researcher I’d put in every executive’s feed.

His research fundamentally changed how I think about sustainable AI adoption.

Ethan Mollick is a Wharton professor and author of the New York Times bestseller Co-Intelligence: Living and Working with AI. 

His work (including research with BCG) found consultants using AI completed tasks…

- 25% faster
- 40% higher quality

…but only when they skilfully used AI as a collaborator, not a replacement.

The part that stuck with me most: leaders decide whether these systems increase human flourishing.

Because AI can go one of two ways:

👉🏽 Extraction: squeeze more out of people, burn them out faster, treat AI as a way to pile on work.

👉🏽 Flourishing: automate the mundane so your people can do higher-value work; grow revenue without growing headcount linearly.

Both approaches want more output. The difference is what happens to your people along the way.

The companies getting real results are asking "what could our people accomplish if we freed them from the work that drains them?"

If you're not already following Ethan Mollick, start there.

Then, share this with a leader trying to figure out what AI adoption actually means for their people.

Most people think AI = prompting. But the real gold is Projects.

Here's what nobody will tell you:

Without Projects, you're stuck in Groundhog Day: explaining the same thing over and over. 

With Projects, you build on yesterday's work instead of starting from zero

I spent yesterday teaching 50 executives how to use it within ChatGPT.

One executive set up a shared project: "Client Response Assistant." 

Uploaded 10 sample responses, added company voice guidelines, and wrote custom instructions.

Now every team member uses the same trained Project. 

Consistent tone. Accurate information. No more starting from zero. 

Of course, humans always edit and verify quality!

The best part? They only have to set it up once to use forever.

Stop using ChatGPT like Google. Start using it like a rockstar employee.

What’s a repetitive task in your business? Could you turn it into a trained “AI employee” via Projects?

Mandates create followers. Discovery creates owners.

A CEO I spoke with last week described it perfectly:

“My teams want to discover solutions themselves. They don't want to say 'I'm doing this because the CEO told me to.'"

This is basic human psychology.

When you hand someone a tool and say "use this," you're taking away their sense of agency.

When they discover a tool and bring it to you, they become invested in making it work.

People don't want another mandate from leadership.

They want to feel like pioneers, not followers.

The more you push AI on your team, the more they’ll resist.

The more you let them discover and experiment with it, the faster they run with it.

As a young founder, I built companies by pushing and executing relentlessly. 

But much of life sits outside our hands: other people’s choices, timing, luck, loss, markets, weather, algorithms, moods, history. 

What IS ours to control is smaller and sharper: attention, interpretation, response, effort, integrity, the stories we tell ourselves about what’s happening, and what we choose to do next.

The quiet relief comes in recognizing that “effort” and “surrender” aren't actually in opposition. They're partners.

We can choose the wave AND ride it. 

Plant and water seeds, but let go of the outcome.

What if the most powerful thing you could do this year isn't pushing harder, but finding where the current is headed, and then paddling with it?

If you’re rolling out ANY kind of change in 2026, here’s what you need: 

Vision - Why does this matter? Why now? How does it benefit everyone?

Skills & Resources - What support will I be given to successfully navigate this change?

Incentives - What's in it for me if I do an amazing job with this change?

Action Plan - What specifically do I do to succeed, and when?

Most companies focus only on skills.

But…

No vision = confusion
No resources = anxiety
No incentives = resistance
No action plan = false starts

You can have the best strategy in the world, but if your team doesn't know why it matters, how to do it, what they get from it, or what to do next?

You just have an expensive slide deck.

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Santiago Jaramillo

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The Battle

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