𝗧𝗿𝗮𝗻𝘀𝗳𝗼𝗿𝗺𝗮𝘁𝗶𝘃𝗲 𝗚𝗿𝗼𝘄𝘁𝗵 𝗖𝗼𝗮𝗰𝗵𝗶𝗻𝗴 𝗳𝗼𝗿 𝗙𝗶𝗿𝘀𝘁-𝗧𝗶𝗺𝗲 𝗙𝗼𝘂𝗻𝗱𝗲𝗿𝘀
It’s not just about scaling your business.
It’s also about scaling you.
From Fortune 500 companies to fast-growing startups, I’ve coached leaders at every stage. Today, my mission is focused: helping first-time founders scale themselves as fast as they scale their companies.
 
𝗠𝘆 𝗙𝗼𝗰𝘂𝘀
Your startup can only grow as fast as you do. As a first-time founder, you’re under pressure from investors, your team, and your family—all while learning on the fly skills that others spend decades mastering. Whether you’re raising capital, hiring your first team, or pushing toward product-market fit, I help you close the gap between where you are and where your company needs you to be.
 
𝗪𝗵𝘆 𝗠𝘆 𝗔𝗽𝗽𝗿𝗼𝗮𝗰𝗵 𝗪𝗼𝗿𝗸𝘀
I bring 20+ years of coaching 10,000+ leaders, founder experience, and cutting-edge insights from neuroscience and behavioral psychology. The result: a proven path to accelerate both personal and company growth. My frameworks help you:
• Transform self-doubt into clarity and influence
• Build and inspire high-performing, durable teams
• Raise capital while staying true to your vision
• Create sustainable success without burnout
• Leverage your existing strengths while closing critical skill gaps
• Grow yourself as fast as your company 
 
𝗪𝗵𝗼 𝗜 𝗦𝗲𝗿𝘃𝗲
My one-on-one clients are founders who:
• Want tailored, responsive coaching that meets them where they are
• Care deeply about building strong teams and cultures
• Aim to create both impact and enterprise value
• Refuse to accept that success means sacrificing their families, health, or lives outside the company
• Are willing to grow personally and professionally to become the leader their company needs 
 
𝗥𝗲𝗮𝗹 𝗜𝗺𝗽𝗮𝗰𝘁
From doubling revenue to unlocking fundraising rounds to transforming team dynamics, my clients consistently achieve breakthrough results—while building lives they actually want to live.
 
𝗪𝗮𝗻𝘁 𝘁𝗼 𝗖𝗼𝗻𝗻𝗲𝗰𝘁?
Visit www.andrewpoles.com/contact or DM me here.

Andrew Poles

We use the word “complete” all the time.
But most people confuse it with “finished.”

They’re not the same.

You can end a relationship and still be carrying it.
You can be in an ongoing partnership and feel fully clear.

Completion is a function of how you relate to reality - not a status update.
In this clip (from my conversation on the Sleep Is A Skill podcast with Mollie), I break down what I mean by being complete - and why it has real implications for how you live, lead, and even sleep.

Coaching first-time founders to grow themselves and their companies | 3x Founder | 22+ years coaching partners like NASA, Dell, Schwab + 10,000 people worldwide

What does insomnia have to do with integrity?
More than most leaders realize.

I once worked with a man who had slept 1–2 hours a night for years. His health was at risk. After doing deep completion work in his relationships and life, he slept 8–10 hours for the first time in decades.

There’s a connection between how complete you are and how well you sleep.
And more than that - your sleep may be a lagging indicator of how powerfully you’re living and leading.

If this resonates, I unpack it further on the Sleep Is A Skill podcast with the amazing Mollie Eastman, episode linked below.  

Sometimes it’s not a sleep issue.
It’s a leadership issue.

#Leadership #ExecutiveCoaching #SleepIsASkill #FounderHealth #Integrity

This is the part of leadership most spreadsheets can’t capture. When behavior stops making sense, there’s almost always unseen pressure in the room.
What stands out here is the refusal to confuse kindness with lowering standards. Real leadership is keeping the bar high AND removing shame from the climb.
Culture isn’t what you say you value - it’s how safe it feels for people to be human while doing hard work.

3 Exits | Founder @ Humble | Strategic Partner @ Loud | Follow for Self Improvement, Growth Strategy & Being A Better Human | Entrepreneurship Coach & Mentor

You have no idea what people are dealing with.
Not even close.
And that’s ok.

Because you just have to be kind.

The person who snapped in your meeting might have a kid who’s struggling.

The one who “doesn’t care anymore” might be keeping a marriage together with duct tape.

The quiet one who missed a deadline might be dealing with a parent who’s fading, fast.

Work makes it easy to pretend everyone is a machine.

Metrics. Output. Deadlines. Slack green dots.

👉 But leadership is what you do when the spreadsheet stops explaining the behaviour.

Bad leaders get this part wrong: 

They think kindness is a personality trait.

It isn’t.
It’s a professional skill. 
And it’s different to being NICE.

Kind isn’t soft.
Kind is controlled.

Nice avoids the hard chat.
Kind has it, without making the person feel small.

Nice lowers standards so nobody feels uncomfortable.
Kind keeps standards high and removes the shame from getting there.

I learned this the hard way building companies from nothing.

⚠️ When you’re under pressure yourself, your instincts get ugly, and you start to:
Push harder. Watch closer. Assume the worst.

It feels “productive”.

It’s usually expensive.

Because people don’t leave jobs first.
They leave the feeling of being misunderstood.

So if you want a practical way to lead like a grown up, try this:

Before you judge the performance, check the pressure they are under.

BUT, a simple “You alright?” is not leadership.
Anyone can say that.

📌This is leadership:

1.	Ask a better question
“What’s taking up headspace right now?”
It gives them a door that isn’t dramatic.

2.	Offer a real option
“Do you want time, help, or privacy?”
Most people just need one of the three.

3.	Separate the person from the work
“You’re not your output. Let’s fix the work.”
That one sentence changes everything.

4.	Adjust the load, not the standards
“What do we de-scope for 7 days?”
Pressure without control creates mistakes.

5.	Protect them in public, coach them in private.
If you correct someone publicly, you teach the whole team to hide.

None of this is “being nice”.

It’s how you keep good people good.

Your culture isn’t your values on a Notion page.
It’s how safe it feels to have a bad week around you.

So yes, you seriously have NO idea what people are dealing with.

Lead like you know that.

-
♻️: Repost to inspire.
➕: Follow Charlie Lass.

Most founders don’t get stuck because things are hard.
They get stuck because of the story they tell themselves about why things shouldn’t be this way.

Loss. Missed signals. Bad hires. Broken trust.
The pain is real — but the suffering is optional.

This week I'm sharing about how leaders unknowingly trap themselves after setbacks, and how dropping one word can unlock clarity, resilience, and forward momentum.

If you’ve been carrying something heavy lately, I hope this offers you some needed clarity.

Sadness: Yes. Suffering: No. Over the last few weeks, several founders I coach have been moving through loss. Not just personal loss — though that’s b

Open article: The “Should” Trap in Leadership by Andrew Poles • 4 min read

When Ken Cox and I were talking recently on the Clicks and Bricks podcast, we kept circling back to something that doesn’t get talked about enough in business:

Your company grows at the speed of your own growth.

Not just revenue.

You can still be making money and feel something in the business has stalled.

Energy drops. Culture gets stale. Decisions feel heavier.

I’ve lived that.

In my first business, I thought learning business meant learning tactics. Strategy. Sales. Operations.

And yes — you do have to learn the “game.”

But what I didn’t understand then was that every ceiling I hit in the business was connected to a ceiling in me.

Fear I hadn’t dealt with.
Conversations I didn’t want to have.
Identity I hadn’t owned yet, or hadn't generated the courage to let go. 

Ken asked me about authenticity and about “next right actions.”

For me, performance really comes down to that:

What is the next right action of integrity here?
Not the most comfortable action.
Not the one that protects your ego.
The one that’s actually right.

That’s where growth happens.
And when that shifts, the business shifts.

If you’re a founder, especially early-stage, I think you’ll appreciate how deep this conversation goes. 

I'll put the link to the full episode in the comments.

Most founder tension isn’t about strategy.

It’s about what no one is saying.

When something is clearly impacting performance–but everyone is pretending it’s not–trust erodes, capacity drops, and the team feels it.

This is about how to name the “boulder in the room” without creating drama, shame, or overcorrection.

If you’ve ever:
-Avoided a hard conversation at the top
-Worried about overstepping vs. under-supporting
-Felt silent tension on your leadership team
-Tried to protect the business without adding pressure

This is for you.

A founder asked me this week how to support a co-founder going through a deeply disruptive personal situation. You know the kind. Sleep off. Nervous s

Open article: The Boulder in the Middle of the Room by Andrew Poles • 5 min read

Your calendar is lying to you.
Not because you’re incapable - but because it’s built on optimism, not reality.
If your day assumes you’ll get everything done, with no interruptions, no fatigue, no tradeoffs… that’s a fantasy, not a system.
You don’t need better memory.
You need a structure that maps real work to real time - and forces honest choices.
High performance starts with a calendar that tells the truth.
Where is yours overpromising right now?

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

Should you share runway with your team? For a long time I was so certain I knew the answer to this.

Years ago, we had about six months of runway left. I didn’t tell the team.

Not because I was lying, but because I believed it was my job to handle it.

If they knew, they’d panic. If they panicked, productivity would drop.

So I carried it alone.

Around that time, we were in a product planning meeting.

We had a big, ambitious roadmap - something that would realistically take a year or two to build. Way more time than we had.

In the meeting, I pushed hard to dramatically narrow the scope.

Fewer features. Faster delivery. A few months instead of years.

Everyone nodded.

After the meeting, one of our engineers pulled me aside and said:

“This makes no sense. This is the biggest load of bullshit.”

He was right.

What I hadn’t shared was the most important piece of context: the runway.

Without that, my decision looked arbitrary. Almost careless.

That was the moment I saw it.

By hiding the runway, I thought I was protecting the team.
What I was actually doing was making it impossible for them to understand or challenge my decisions.

Thankfully, that conversation forced me to do the harder thing.

I shared the runway.
We talked openly about the clock.
And instead of panic, something else happened.

People stepped up.

Once everyone could see the constraints, we built a plan that actually fit inside them. Decisions improved. Alignment improved. And the company recovered.

People don’t get scared when you share reality early.
They get scared when they sense something’s wrong but don’t know what.

If you’re running a venture-backed company that’s losing money, there is a clock.

You can’t ask a team to win the game if they can’t see it.

Leadership isn’t about looking certain. It’s about giving people enough truth to actually help.

Ryan Vaughn

No alternative text description for this image

Most leaders don’t fail because they lack talent. They fail because success slowly blinds them.

Leadership has an uncomfortable paradox: The more authority you gain, the less accurate your self-awareness becomes.

Research backs this up. In multiple studies, the least effective CEOs consistently rated themselves the highest, while their teams rated them the lowest. The most effective leaders showed the opposite pattern.

So what gets in the way?

After years of working with founders and CEOs, I’ve seen four barriers show up again and again.

1. You don’t look.

Running a company is all-consuming. Many leaders spend their days focused entirely on the work “out there” - product, sales, execution, without ever examining how they are shaping the results they’re getting. 

Leadership style feels fixed. “That’s just who I am.” It isn’t.

2. You don’t ask.

Even leaders who are self-reflective often avoid feedback. Not because they don’t value it, but because they’re afraid of what they might hear. Feedback activates old patterns around criticism, approval, and worth. So leaders choose comfort over clarity, often simply by being passive and not asking.

3. You don’t listen.

I still remember the first time someone told me that once I made up my mind, I stopped listening. My reaction wasn’t curiosity. It was defensiveness.

At the time, I thought we were just disagreeing. What I didn’t see was the real consequence: after that moment, that person never gave me honest feedback again. Leaders don’t lose feedback because people agree with them. They lose it because people learn it’s unsafe to speak.

4. You don’t interpret.

Power distorts reality. People compliment you more. They soften criticism. Leaders live in a bubble, not because they’re bad people, but because hierarchy changes behavior. If you don’t account for that, you’ll misread what’s actually true.

Self-awareness isn’t about becoming someone else.

It’s about aligning how you see yourself with how others experience you, so you can adapt intentionally instead of running blind.

The uncomfortable truth is that leadership success depends on overcoming forces that constantly push you toward self-delusion.

And the more successful you become, the more deliberate you have to be to stay awake.

---

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.

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

Most leaders don’t fail because they lack courage. They fail because, when consensus disagrees with them, they stop trusting themselves.

One of the hardest parts of leadership isn’t making decisions.

It’s making decisions when consensus is pointing in the opposite direction.

Most leaders are taught - explicitly or not, that the safest move is the one everyone agrees with. 

Clear logic. Strong validation. Plenty of nods around the room. 

Consensus feels like evidence you’re doing the right thing.

But the decisions that actually change outcomes rarely feel that way at the start.

They feel uncomfortable.
They invite skepticism.
They make other people nervous.

History is full of examples of this tension.

Steve Jobs resisted giving people more features when everyone else believed “more” was better.
Henry Ford ignored requests for faster horses and bet on a completely different model.

At the time, these choices didn’t look visionary. They looked wrong.

Not because those leaders were trying to be contrarian, but because they were willing to trust their own judgment over collective agreement.

This is where leadership gets psychologically hard.

When you go against consensus, you lose immediate validation. You don’t get reassurance. You don’t get certainty. All you have is your own internal sense that this is the direction worth committing to, even if you can’t fully prove it yet.

And that’s the part most people struggle with.

It’s far easier to be aligned than to be right.
It’s far easier to be approved of than to be trusted later.

But if you want outcomes that are meaningfully different, you can’t rely on consensus as your compass. Consensus optimizes for safety. Leadership, at its best, optimizes for truth.

This doesn’t mean ignoring data or dismissing other perspectives. It means recognizing that the most important calls often emerge before the data is obvious, and before agreement catches up.

If you find yourself facing resistance, confusion, or disbelief around a decision you feel deeply committed to, it’s worth asking:

Am I avoiding this because it’s wrong?
Or because it asks me to stand without validation for a while?

That tension isn’t a signal you’re failing.

It’s often the price of doing work that actually matters.

---

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, one trait has defined me more than any other: When I say I’m going to do something, I do it - No renegotiation. No backing out.

Once I give my word, I move heaven and earth to keep it.

That habit has built companies, shaped teams, and driven a lot of my success. And I still value it deeply.

Recently, though, I ran into its edge.

A month ago, I told myself I’d write every day.
No strategy. No goal. Just a commitment.

And I followed through. Every single day. Including very early mornings.
The writing came back online — which, in hindsight, was probably the point.

But something familiar showed up alongside it.

I noticed how quickly my sense of self had attached itself to being perfect at the commitment.

Miss a day → something is wrong with me.
Keep the streak → I’m okay.

That’s when it clicked.

It’s unavoidable to attach some identity to the things you care deeply about. Integrity included.
The problem isn’t caring. The problem is when that identity becomes all-or-nothing.

When your sense of worth depends on never missing, that identity becomes brittle.

One slip isn’t information, it’s catastrophe.

What I’m learning now is something subtler.

I still care deeply about keeping my word. I’m still intentional about it.
But when I miss once, I don’t collapse the whole identity anymore.

I clean it up. I recommit. I keep going.

At first, that felt like slacking.
Now, it feels like progress.

More resilient. More humane. More relaxed.

I’m still writing.

Just with space for imperfection, so the work comes from expression, not self-punishment.

More than any amount of success, I want to be free.

Most founders say they hire people smarter than them (many even believe this). But after coaching 100s of founders, I can say unequivocally that most don't.

Instead, they keep building teams that can’t truly challenge them. This isn’t a hiring problem. It’s a psychological one.

One of the most reliable patterns I see in leadership is this: the dynamics in our companies usually mirror something unresolved in us.

High achievers often grow up learning that being “better” earns safety, approval, and a sense of worth. Over time, that pattern becomes fuel. It drives ambition, discipline, and results.

It also comes with a cost.

When achievement becomes the way we feel okay, being the most competent person in the room stops being a role and starts being an identity.

Consciously, leaders want great people.
Unconsciously, many still want to feel admired, needed, and secure.

So they hire people who look impressive but not so strong that they threaten the leader’s sense of value. The team functions, but it never fully stretches. Innovation slows. Challenge disappears.

When those hires eventually fall short, it feels frustrating. But at a deeper level, the system is working exactly as designed.

The leader remains indispensable.

This is why “hire people smarter than you” isn’t just operational advice. For some founders, it’s deep inner work.

If your team can’t challenge you, it’s worth asking: Not what’s wrong with the talent market, but what part of you still needs to be the strongest one in the room.

Real leadership begins when your worth no longer depends on winning the bike race
 
---

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.

Why founders keep choosing certainty, even when it hurts:

When things get uncertain, founders don’t reach for what’s most true.
They reach for what feels most controllable.
Even when that certainty quietly pulls them away from reality.

I see this pattern over and over again.

Uncertainty lights up something deep in the nervous system. It feels unsafe. And when outcomes aren’t clear, many founders respond by tightening the story.

Clear plans.
Confident narratives.
Strong projections about where this is all going.

Certainty feels grounding.

There was a study years ago that stuck with me. 

Lab rats were given a choice between two environments. One in which they'd be shocked at a 7/10, every once in a while.

The other in which they'd be shocked constantly at a 10/10.

They overwhelmingly chose the second.

Not because it was better. Because it was certain.

We’re not that different.

Here’s the problem: certainty is almost never the truth.

Reality is nuanced. It’s complex. It’s more like an old Buddhist parable about blind men encountering an elephant for the first time.

One touches the trunk and insists it’s a snake.
Another grabs the leg and says it’s a tree.
Another holds the ear and swears it’s a fan.

Each person is experiencing something real.
None of them are seeing the whole thing.

Business works the same way. No matter your role, you only ever see part of the elephant. The moment a leader presents their partial view as certain, they simplify what’s actually happening, and make it harder for others to contribute the missing pieces.

Certainty is comfortable. It calms the nervous system. It sells well.

But it comes at a cost.

When leaders optimize for certainty, they stop listening deeply. Teams learn which truths are welcome and which ones aren’t. Complexity gets flattened before it’s understood.

You get clarity, but not accuracy.

The capacity to stay present when the picture is incomplete - without rushing to false confidence, is one of the most important leadership skills there is.

Not because it feels good.

But because it keeps you connected to reality.

Big news! I'm so excited to welcome Derek Haswell to the team as a Partner and Founder Coach! 

I met Derek early in my coaching journey, and have wanted to conspire together in some way for years. He's amazing. And now I'm eager to see what we get up to together at IO. 

In 2013, Derek accidentally co-founded a meditation company. He helped build an award-winning product, scaled to 8-figure ARR, and worked with some of the best meditation teachers in the world, including the Dalai Lama.

Today, Derek blends outer work (strategy, goals, accountability) with inner work (self-awareness, resilience, what's actually driving the stuckness).

In his own words:

“I've lived that trade-off as a founder and it sucked... for everyone. Then I discovered they could be part of the same path, and it changed everything. Now I help founders make the same shift.”

I’ve known Derek for years, as a coach, a builder, and a wonderful human being, and I’m so excited to co-create Inside-Out with him, and support our founders in scaling consciously.

Check out Derek's full story in the comments. It's worth the read.

This is what collapse looks like before anyone notices.

My company was dead.
The data screamed surrender.

What surprised me wasn’t the failure.
It was how much of my identity went down with it.

Businesses can be rebuilt.
Egos take longer.

I remember going to bed at 6:30 pm that night, crying about my business, feeling like the whole thing was f***ed.

We were running out of cash, over 70 employees and their families were counting on me to find more cash, and even though the business was meeting its objectives, fundraising was going terribly. The $10M funding round we were expecting had evaporated in a single phone call. The investor who had spent dozens of hours with us pulled out, citing market concerns.

I knew the next step was to open my laptop and get back to work, but it all seemed pointless. We were going to run out of money, I was going to let down everyone who had believed in me, and I personally would be branded a failure and run out of town as a result.

I forced myself to look up when my wife, Laura, came home. She tried to empathize, to help, even. But I didn't want to hear it. All our options sucked. We had banked everything on one investor, and now it was all going to blow up. Our business was gone, and I wanted to crawl into a hole until I died.

So I slept. When I woke up, the investor was still a pass.

We would run out of money, and it would be all my fault.

In the middle of that spiral, I got a call from one of my investors, Avram Grant, a man who speaks in parables. 

"Ryan," he said, his voice calm against my panic. "You might give this business everything you have. You might sacrifice every part of yourself to it, and it still might not succeed. Life offers no guarantees." 

"But," he continued, "there is exactly one way to ensure that it doesn’t succeed. And that is to stop." 

At that moment, sitting in my kitchen, every shred of logical data told me to quit. If I had made a pros/cons list, the Cons column would have physically tipped the paper over.

But I chose to keep going.

Three months later, we secured the financing. We launched the 2.0 version of our product, which led the market and the company to an exit.

Most of us spend our lives trying to optimize for certainty. We want a sign from the universe that the path is "right" before we take the next step. We wait for the data to tell us it's safe to be brave. 

But there is far more to leadership than simply following the data - it requires holding the vision when the data has gone dark. 

The universe doesn't present "good choices" or "bad choices." It presents invitations. We build the rightness of the path through our actions, through our willingness to keep showing up honestly, and through our commitment to the outcome we want, not the one that's statistically likely.

If you are facing a moment where the data screams one thing, but your soul whispers another, take it from Avram: 

The only way to guarantee failure is to walk away.

Enough. The most elusive word in an entrepreneur’s life.

In the first half of life, that word is fuel. “Enough” is something you measure against growth, metrics, valuation, achievement. And the world reinforces it.

Every ambitious system does this. Religions. Institutions. Startups. They hand you a vision of what is good and right and tell you, “Become this. Sacrifice for this. Be better than everyone else at this.”

Then what happens?

You push. You optimize. You stretch yourself thin running toward a non-existent finish line called “enough.”

Then comes the second half of the journey. And it doesn’t arrive gently. It arrives as a crucible. Burnout, disillusionment, the sense that the ladder you’ve been climbing no longer feels like yours.

You realize you’ll never do 99% of what you could do.

The cold reality sets in. Time an energy are finite. 

And the question changes from “How much can I achieve? to “What actually matters to me?”

In the second half, “enough” stops being something you prove. It stops being a comparison or someone else’s definition.

It becomes inherent. A way of moving through your life and work.

The first half of the journey is about expansion.
The second half is about authorship.

What half are you currently in?

For most of my career, creativity came from pressure. From big problems I had to solve. From outcomes I needed to hit. 

But there's a different kind of creativity that lives underneath all of that. It comes from joy. From play. From love. I call this place presence. And it's where the most interesting work happens.

I see this all the time working with post-exit founders. During the scale-up, every identity shift serves the company. But after the exit? When that crutch is gone and you're staring at a blank page, wondering what's next?

That's when the real work begins.

Because now you're not choosing who to be based on what needs to get built. 
It's terrifying. And it's also the most creative place I've ever been.

"The moment you doubt whether you can fly, you cease forever to be able to do it."
–J.M. Barrie, Peter Pan

I've played basketball my entire life, and here’s what I’ve noticed. If I step on the court
believing I'm the best player there, I hoop. If I'm uncertain, I play poorly.
Leadership works the same way. If you believe you'll win, you'll win. If you believe you'll lose, you'l lose.
Confidence is king.

But real confidence isn't peacocking. It's not pretending you have all the answers. It's not even earned through success. You can build a great company and still be one bad outcome away from doubting yourself.

Real confidence comes from alignment between who you are inside and how you show up in the world.
The ball’s in your court.

There’s a hidden force behind many “productivity problems.”

It’s not laziness. It’s not discipline. It’s not even time management.
It’s fear.

When pressure, uncertainty, or self-doubt creep in, the brain doesn’t lean into bold work.

It looks for safety. Suddenly emails feel urgent. Slack feels necessary. Small,
controllable tasks replace the ambiguous, high-stakes ones that move things forward.
From the outside, it looks like busyness.
From the inside, it’s avoidance, rooted in fear.
And the insane part? It feels rational.

Understanding how fear quietly reshapes attention, decision-making, and execution is
one of the biggest unlocks for founders and high performers.

Because you’re not always fighting a workload problem.

Sometimes you’re fighting a fear problem.

The most defining part of leadership isn’t certainty. It’s the unknown.
Especially now, when AI and systems increasingly handle the predictable, repeatable, “figured-out” work, what remains for founders and CEOs is ambiguity.

Leadership becomes a cycle:
Enter the unfamiliar.
Navigate the discomfort.
Create clarity.
Hand it off.
Repeat.

The lesson is simple, and I’m trying to follow it myself.
Stop treating discomfort as a warning sign.
It’s usually evidence you’re exactly where you need to be.
Learn to recognize it.

Normalize it.
Build the internal capacity to move forward anyway.

Angry seagulls are going to make you a better leader. Stick with me and I’ll
explain.

You"re in a board meeting. An investor cuts you off. "I don't think you know what you're doing. Your strategy is completely wrong."
Do you fight back or shut down?
When this happened to me once, I made two mistakes.

First, I said "okay" while quietly resenting the investor. That didn't work.
Then I pushed back and defended myself. Also a mistake. It took me years to find the third option. Get curious.

Not the kind of curious where you ask questions to trap them. The kind where you stay grounded in yourself while opening up to what you might be missing.

You're going to run into "angry seagull" investors. It's not if, it's when.
You can fight back. You might win the moment, but you won't grow.

You can blindly agree. You'll lead your company somewhere you don't believe in. Or you can ask questions. Really listen. Stay confident while staying open.

How you react when you're uncomfortable dictates the trajectory of your company and
career.

So…

What angry seagulls are in your life right now?
The investor who keeps pushing back?
The co-founder who questions every decision?

The board member who never seems satisfied?

What would it look like to stop resisting them—or blindly accepting them—and start
getting curious about what they're here to teach you?

https://lnkd.in/gHUzHVcZ

This video has been making its way around the Internet. You should stop and watch before you keep reading.

Most people think reading 900 words per minute is impossible. Until they do it.
What changed?

Not their brain. Not their intelligence.
Their belief about what was possible.

We’ve seen this before.

Same with running the four-minute mile.
And having smart machines.

Entrepreneurs do this constantly.

We build invisible ceilings and convince ourselves they’re real.
Then a crisis hits. Or something else forces your hand.
And you discover the ceiling was never real.

When people read 900 words per minute for the first time, there’s genuine shock. Like they discovered some supernatural ability.
But they always had it. They just never gave themselves permission to use it.

Most limitations are just untested assumptions.

Question the ceilings. Test the assumptions.
You’ll probably discover you’ve had the ability all along.

An interesting question to sit with:
What limitation are you currently living with that is, in fact, just a belief?

The best CEOs I know have shorter to-do lists than you.

A perk of my work is getting an intimate look into the habits and systems of leaders across the world.

And something I've noticed about the best CEOs isn't what they do. It's what they decide NOT to do.

Most people let their to-do list become infinite. They pack in as much as possible, check off what they can, and roll everything else forward. The list never ends. And they wear it like a badge of honor.

But here's what they're avoiding: The confrontation of choice.

Saying "I'm not going to do this thing" feels permanent and final. Like you're actively choosing failure in that area.

And that's uncomfortable.

So instead, people keep everything on the list. They tell themselves, "I'll get to it eventually" and avoid the psychological weight of consciously letting something die.

The best CEOs do the opposite.

They stack rank their tasks by importance, look at their calendar, and slot only what will fit. Then they consciously move everything else to next week's list, or kill it entirely.

The result? They finish their work most days. And they get exceptionally good at one of the most important skills in leadership, which is saying no to important things.

Because here's the truth…

Your workload never decreases as you grow. You just get better at leading. And having less time forces you to delegate, empower your people, and build your organization instead of just working harder.

Your to-do list is a daily training ground for this.

Every day, you're forced to confront what dies so something more important can live.

That confrontation is the work.

Not the hustle of doing more, not the performance of appearing busy.

The discipline of doing what counts. And ruthlessly eliminating what doesn't.

https://lnkd.in/gbCGxgNW

Open article: Inside Out Leadership — CEO's Personal Management System: Prioritize Deep Work & Self-Care by leadinsideout.io

Inside Out Leadership — CEO's Personal Management System: Prioritize Deep Work & Self-Care

The most comforting and terrifying thing I’ve learned in business is the same truth. Here's the story.

My real education happened inside a startup accelerator. 12 intense weeks, surrounded
by founders, mentors, and Thursday night “fireside chats.”

One moment stuck.
A wildly successful executive paused when asked for his single biggest lesson for
entrepreneurs.
“Nobody knows what the hell they’re doing,” he said.

“The difference between successful companies and unsuccessful companies is that, with the successful ones, you can’t tell.”
That perspective has followed me through every stage of my career.

Do they teach that in school? I wouldn’t know.

https://lnkd.in/g_P32hAy

Grant and Zero are a great company doing important work on one of the world's most pressing problems. So excited to see what you guys are creating over there. Congrats on the success, and here's to many more!

Today we're excited to announce that we raised a $16.8M Series A! 

Led by Prelude Ventures with participation from SJF Ventures, Exelon, and our existing investors VoLo Earth Ventures, FJ Labs, and Overture Ventures. 

With this fresh round of capital, we'll expand our digital-first approach and team to help rebuild communities across the country through affordable, healthy homes. 

Want to learn more? Take a look ⬇️ 
https://lnkd.in/ga77JW4w

Open article: Zero Homes Raises $16.8M to Digitize Home Upgrades for Homeowners and Contractors by zerohomes.com

Zero Homes Raises $16.8M to Digitize Home Upgrades for Homeowners and Contractors

I once heard a story that stayed with me.

A little girl walks through a garden for the first time. It was overwhelmingly beautiful, and
she runs inside to tell her mother.

Her mother smiles. “Those are pretty flowers, aren’t they?”
The next day, the girl returns to the garden… and sees “pretty flowers.”

The label stripped the magic. It flattens wonder into familiarity.

I catch myself doing this in business.
A group of complex, brilliant, unpredictable humans becomes “the sales team.”
Or “engineering.”

And without realizing it, I narrow how I see them.

Abstraction isn’t wrong. It’s essential.
But every so often, a moment of awe — in nature, in conversation, in work — reminds
me:

Reality is always richer than the words we use to contain it.

I’m doing my best to remember that.

https://lnkd.in/gxyzemuH

Most leaders don’t have a strategy problem.
They have a validation problem.

The most dangerous addiction in business isn’t money or power.
It’s being liked.

Applause feels like progress.
Agreement feels like safety.

Slowly, decisions stop being about what’s right and start being about what won’t upset anyone.

That’s not leadership.
That’s people-pleasing with a title.

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