Ryan Rouse

Growth advisor to consumer businesses with a focus on every line of the P&L | Previously, Co-Founder at Factor Meals (acquired), CEO at Highkey

Growth-minded CPG leader with deep experience across finance, brand building, and operational leadership.

After more than a decade in finance—culminating in an eight-year tenure at Merrill Lynch—I co-founded Factor_, a ready-to-eat meal delivery company that went on to be acquired by HelloFresh for $277M in 2020.

I joined HighKey Snacks as Chief Marketing Officer and later CEO, guiding the low-sugar snack brand through rapid expansion and an acquisition in 2024.

I'm currently the President of MALK Organics, a fast-growing, near nine-figure brand redefining the plant-based milk category with its commitment to clean, organic ingredients and uncompromising quality.

And I write a newsletter about what it really takes to grow—your company, your mindset, your tolerance for chaos:
​
​• The unfiltered truth about building a brand
• Why “strategy” isn’t always strategic
• What to do when everything feels on fire
• Mindset shifts that keep you sane(ish)​
• Founder mistakes, market moves, and lessons I’m still learning​
​
​Part playbook, part perspective shift.
For anyone trying to grow something—and keep their head on straight.

Sign up using the link here (or below my profile pic above): https://ryanrouse.me/

Vice President | Partner

Data driven investors in early stage consumer brands. 

Watched someone's face light up yesterday. 

I'd just told them their bonus number.

Not a polite smile. Not a professional nod.

Their entire face changed.

After a killer 2025 at MALK, I got to sit down with my team over the last few days and share what they'd earned.

These conversations are my favorite part of leadership.

Not because I'm handing out money. Because I'm watching bets pay off.

Every hire is a bet. Every promotion. Every time you give someone more responsibility than they've had before, you're betting they'll rise to it.

Most of those bets don't feel safe when you make them.

You're trusting people before they've proven they can handle it. Giving them room to fail. Hoping like hell they don't.

And then you get a year like this one.

Where chaos turned into wins. Grind turned into growth. And the people you bet on delivered more than you imagined.

That's the payoff.

Not the revenue. Not the milestones.

Watching someone realize their work mattered (and was recognized).

Never been on a Forbes list // President @ MALK Organics // Follow for posts about the highs and lows of building consumer brands from 13+ years in the trenches actually doing it

MALK made the Bain 2026 US Insurgent Brands list 👀 

What I love about this list is it's numbers based (i.e., not a popularity contest.)

• Greater than $35MM in revenue
• Grown at least 10x faster than their category average over the last 5 years
• Maintained positive growth over the past 2 years

A couple other stats that stand out. 

- While the overall market grew less than 2% in 2025, the insurgents captured 36% of market growth.

- Insurgents grew volumes by approximately 55% year over year in a market where overall volumes were largely flat, demonstrating that their growth reflects real consumer demand, not just price inflation.

- Insurgent brands continue to be at the forefront of where consumer demand is accelerating with 44% of the brands featuring natural or organic claims. 

I'm proud of what we're building at MALK. 

And honored to sit alongside the other amazing Brands on this list. 

Let's get after it once again in 2026!

We’re debuting our new Cleaner Creamers at Expo West.

Organic, dairy-free, and made without gums, oils, or natural flavors. 

One thing we all need at Expo is coffee (duh), so come have a cold brew on us at our Cleaner Creamer Coffee Bar outside of Hall E (S21). 

Or explore the full MALK lineup (and more) at our main booth N322.

Lastly, we're also hosting a happy hour on Thursday 3/5, from 4-5PM — where MALKtinis will also make their debut :)

See you there!

(Full details in the link in the comments)

I turn 47 today.

Five years ago, I wrote a post on my 42nd birthday about entering my prime.

Looking back, I was right. But I underestimated what was coming.

Because every year since then, I've finished even stronger than I started.

Not older. Stronger.

Mentally. Physically. Emotionally.

Patience made me stronger mentally.

I stopped needing everything to happen right now. The urgency that used to consume me is more controlled. The more I let things unfold, the quieter my mind gets. Clearer. 

Acceptance made me stronger emotionally.

I stopped fighting what I can't control. The setbacks, disappointments, and other people's opinions that used to stunt me... I learned to let them pass through instead of take up residence.

Balance made me stronger physically.

I stopped treating my body like it was separate from everything else. Sleep matters. Recovery matters. I'm in better shape at 47 than I was at 37 because I finally stopped grinding myself into the ground.

Focus made me stronger universally. 

I stopped giving F's to things that don't fill me up. Relationships, opportunities, envy of other's people's highlight reels on social media. 

I'm still a work in progress, but recognize and acknowledge that if I'm going to grow, those are the areas that need to be more developed. So I work on them. 

At 22, I thought 47 was ancient.

At 47, I know the truth.

I'm not declining. I'm compounding.

Every hard conversation. Every failure I sat with instead of ran from. Every time I chose the long game over the quick win.

It all stacks.

So if the 22-year-old version of me showed up today, I'd tell him the same thing I said five years ago:

You have no shot against this version of me.

But now I'd add one thing:

You won't have a shot against the 60-year-old version either.

We’re hiring a Director of Finance.

You’ll report directly to and work closely with our CFO Jay Stone. 

MALK is growing fast with a smaller team which means you’ll have meaningful ownership and impact.

It also means we need a builder. 

Someone comfortable operating in the fast-moving, messy world of high-growth CPG.

You’ll partner closely with Sales, Marketing, Category Insights, and Demand Planning to help us understand what’s driving growth and how we invest to scale the business.

We have a culture we protect furiously. 

A group of humans who are all different, but who have common traits. 

Self motivated, open minded, intellectually curious, and cool. 

Last thing I’ll say is this.

This place is special. And will be one of the most fun and rewarding work experiences of your life if you’re the right fit. 

I don’t just believe that. I know it. 

If you’re interested, or know someone great, email hr@malkorganics.com. 

Or text me if you know me.

I've never met a happy person in a hurry.

Last week I looked down and realized I'd eaten an entire lunch without tasting a single bite.

Fork in one hand. Slack in the other. Eyes on the next call starting in 4 minutes.

I couldn't tell you what I ate. I was already somewhere else.

And I thought: what am I actually racing toward?

Look, I get it. Speed wins. 

I've built my entire career on moving fast. I preach it constantly.

But there's a difference between moving with urgency and living in a constant state of hurry.

Urgency is a choice. Hurry is a disease.

Urgency says "this matters, let's go."
Hurry says "this moment isn't good enough. I need to be somewhere else."

Every time you're rushing, you're basically telling yourself: I don't want to be here. I want to be there.

"There" is always some future moment. When the deal closes. When the launch is done. When you're "further along."

You know what you'll find when I got there?

Another "there."

Happiness isn't waiting for you at the finish line.

It's not in the next milestone or the cleared inbox or the lunch you inhaled at your desk.

It's here. Right now. 

Even if "here" isn't where you thought you'd be.

If you can't get your arms around that, happiness will always elude you.

—

I write emails. Unfiltered takes from 12+ years building brands.

It's free. Subscribe (or don't):

https://ryanrouse.me/

Stop trying to be Steve Jobs.

He's the exception, not the rule.

An entire generation of founders watched the turtleneck tantrums and thought that was the playbook for great leadership. 

It's not.

I've watched brilliant people flame out because nobody wanted to work with them.

Being easy to work with is a competitive advantage.

Nice people make more friends.
Nice people create more loyalty from colleagues.
Friends and loyal colleagues expand your network.
Your network brings more opportunity.

The math is simple.

Be decent.

—

I write emails. Unfiltered takes from 12+ years building brands.

It's free. Subscribe (or don't):

https://ryanrouse.me/

There’s nothing like putting your skills to the test.

I say it to the team all the time. 

No doubt they’re sick of hearing it. 

But getting the chance to put your hard work to the test is a privilege. 

Full stop. 

I’ve worked really hard on my jiu jitsu since picking it up 3.5 years ago. 

And love to compete in tournaments because what better way to test skills than that?

This is me getting a choke submission in the gold medal match at the Austin Open last week. 

Stoke Level = Off The Charts

Really proud of the work I’ve put in regardless of the outcome. 

But winning is pretty sweet.

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I used to think good leaders had an opinion on everything.

Every deck. Every decision. Every damn detail.

If someone brought me something, I had to weigh in. That was my job, right?

Wrong.

I was exhausting my team and myself.

Not everything demands your judgment.

You're actually allowed to say "I trust your call on this."

You can sit in a meeting and just listen. You can let your direct report run with their idea without inserting yourself into every corner of it.

The best leaders I know? They're selective about where they spend their opinion capital.

They know the difference between:

• Things that need their input
• Things that need their approval
• Things that need neither

When you comment on everything, two things happen:

Your team stops thinking for themselves. And you become the bottleneck.

So now I ask myself: Does this actually need me? Or do I just want to feel important?

Most of the time, it's the latter.

Shutting up is a skill. And it might be the most underrated one in leadership.

—

I write emails. Unfiltered takes from 12+ years building brands.

It's free. Subscribe (or don't):

https://ryanrouse.me/

Nothing will advance your career faster than being able to connect with other humans.

It trumps every other skill by a country mile.

This starts with you making everything less about you and more about them.

Ironically, even though it's the most important skill to get you into a leadership position, it's actually more important once you get there.


—

I write emails. Unfiltered takes from 12+ years building brands.

It's free. Subscribe (or don't):

https://ryanrouse.me/

The best leaders don't announce themselves.

Sure, you can feel their presence.

But when they're with their team, there's no performance. 

No need to remind everyone they're the boss.

Their authority comes from how they listen. How they ask questions instead of giving orders. How they make space for others to shine.

The insecure ones do the opposite.

They interrupt. 
They dominate conversations. 
They make damn sure you know they're running the show.

But real leadership shows up in the room without saying a word. 

People lean in when they speak. 
Decisions get made faster. 
The team moves with confidence.

That's the tell.

If someone has to constantly remind you they're in charge, they probably aren't.

Your best relationships aren't built in the good times.

They're forged in the shit storms.

When revenue's down. When you're making layoffs. When the product launch flops and everyone's pointing fingers.

That's when you find out who's really on your team.

I've watched partnerships crumble during growth phases that should've been celebrations. And I've seen teams get tighter during crises that should've torn them apart.

The difference?

How you communicate when it's hard. 

Whether you protect respect even when you disagree. If you can trust each other when the path forward isn't clear.

You can't go back to the early days when everything felt simple. When the stakes were lower and disagreements didn't matter as much.

And honestly? You shouldn't want to.

Because every hard conversation, every tense board meeting, every moment you chose trust over ego made you stronger.

The relationships that survive the pressure are the ones worth keeping.

Everything else is just networking.

Self reflection is in short supply.

Most people are so damn sure they're right.

I get it. Confidence feels good. Certainty is comfortable.

But what I've learned in nearly 47 years on this planet is the most dangerous thing you can do is stop asking yourself one simple question:

Am I wrong?

Not once in a while. Regularly.

Pick something you're convinced of and argue against yourself. Make the best case you can for the opposite view.

You'll either strengthen your position or realize you need to change it.

Either way, you win.

The people who do this consistently? They make better decisions. They build stronger teams. They avoid costly mistakes.

The ones who don't? 

They get blindsided by their own blind spots.


—

I write emails. Unfiltered takes from 12+ years building brands.

It's free. Subscribe (or don't):

https://ryanrouse.me/

People who tell you to "enjoy the journey" have already finished theirs.

They're not wrong. They're just not useful.

When I was grinding 90-hour weeks at Factor_, people would say "enjoy the process!"

I wasn't enjoying anything. I was trying not to go bankrupt.

You can't enjoy drowning while you're drowning. You're just trying to breathe.

Here's what actually helps:

• Permission to not love every moment
• Knowing survival mode is temporary
• Understanding gratitude comes later

Stop beating yourself up for not loving the grind.

The appreciation comes when you've got bandwidth for it.

Right now? Just keep climbing.

—

I write emails. Unfiltered takes from 12+ years building brands.

It's free. Subscribe (or don't):

https://ryanrouse.me/

Intelligence isn't why leaders fail.

They fail because they can't connect.

I watched a VP with all the talent in the world lose his team in 6 months. Not because the plan was wrong. Because no one wanted to follow him.

He couldn't read a room. Couldn't give feedback without destroying morale. Couldn't build trust.

The gap between good and great leadership isn't IQ. It's EQ.

You can be the smartest person in the building and still create a vibe people don't enjoy.

Because leadership isn't about being right. It's about bringing people along with you.

Your direct reports. 
Your counterparts. 
Your boss. 

The hard skills get you in the door. The soft skills determine how far you go.

If you're stuck at a certain level, ask yourself: Is it really your capabilities holding you back? Or is it how you make people feel?

Start there.

The hardest workers at startups aren't always the ones who get promoted.

I've watched this play out dozens of times across three companies.

Everyone's grinding. Everyone's busy. That's table stakes.

The difference? It's not who works the most hours.

It's who takes ownership of their own growth.

Take two different people. Both talented. Both working their asses off.

One finishes a project and asks "what's next?" before you even have time to think about it. She spots gaps in your process and just... fixes them. Builds skills you didn't even know you needed yet.

The other does his job well. Really well. But he waits. Waits for you to assign the next thing. Waits for feedback. Waits for someone to tap him on the shoulder and say "here's your growth opportunity."

Guess which one gets promoted?

Here's the reality at a startup: No one has time to manage your career development for you.

Your boss is putting out fires. Your company is trying not to die. There's no HR department building you a nice little development plan.

If you're waiting for that, you're already behind.

The people who make it aren't necessarily the smartest or most experienced.

They're the ones who look at their current role and ask "what's next?" without being prompted.

They find the gaps. They raise their hand. They build new skills before they need them.

The others? They're always surprised when growth opportunities go to someone else.

Stop waiting. Start owning.


—

I write emails. Unfiltered takes from 12+ years building brands.

It's free. Subscribe (or don't):

https://ryanrouse.me/

I used to think confidence was more correlated to competence.

That the person dominating the conversation must know what they're talking about.

I was wrong.

Tens of thousands of meetings over the decades taught me this lesson the hard way.

The pattern is always the same.

Someone walks in with all the answers. Voice loud. Presence commanding.

Most people defer to them because of the volume and presence.

But...

The quiet ones. The people who didn't fight for airtime. Who wait until everyone else has spoken before they say anything at all.

They aren't quiet because they have nothing to say.

They're quiet because they were actually thinking. Processing.

Connecting dots that everyone else misses while they're busy talking.

I've watched entire strategies shift because someone who barely said a word for 45 minutes finally raised their hand and pointed out the one thing everyone else overlooked.

The flaw in the logic. The customer insight we missed. The operational reality that would kill the whole plan.

But here's the thing.
If you're not paying attention, you'll miss it entirely.

Because those voices don't demand space. They don't interrupt. They don't repeat themselves three times to make sure everyone heard.

They say it once. Quietly. And if you're not listening, it's gone.

The quiet people aren't always right.

But when they're wrong? They're wrong in interesting ways.

Ways that make you think differently. Ways that open up new angles you hadn't considered.

Real insight doesn't need volume.

It needs space. And attention. And someone willing to create room for it to surface.

If you're leading a team, this matters more than you think.

Because the breakthrough idea you're looking for? It's probably already in the room.

It's just not screaming at you.

It's sitting quietly in the corner, waiting for someone to notice.

Pay attention to the people who don't fight for airtime.

Ask them what they think.

Then shut up and listen.

You might be surprised what you've been missing.

Momentum is the most powerful force in business.

It's intoxicating. And finicky as hell.

When you have it, deals close faster. Hiring gets simpler. Problems suddenly have solutions.

That part is obvious. The part that isn't... 

Your team doesn't feel it the way you do.

They're in the weeds. Focused on tasks. They don't see the pattern you're seeing.

So when momentum's on your side, your job isn't just to ride it.

It's to make sure everyone else feels it too.

Point it out. Celebrate wins. Connect the dots between their work and the results. 

So you can get the most out of it when the winds are at your back. 

Because it can disappear as fast as it arrived.

Consuming content doesn't build confidence.

Doing does.

I spent years thinking I needed one more book, one more course, one more framework before I was ready. Spoiler: I was never ready.

The confidence I have now didn't come from any of that.

It came from:

• Launching things that flopped
• Making calls I wasn't sure about
• Building Factor_ with no roadmap
• Getting it wrong, then getting it right

You can watch every YouTube video on swimming. But you don't learn to swim until you're in the water.

Same with business. Same with parenthood. Same with life.

The reps are the education. The failures are the curriculum. The wins are just proof you survived long enough to figure it out.

Stop waiting until you feel ready. You won't.

Start before you're confident. That's how confidence actually gets built.

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

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.

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.

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.

Have had the pleasure and privilege of getting to know Ryan, and +1 to all this

Founder/CEO at HealthBar | Healthcare Delivery & Payor Model Innovator/Entrepreneur/RN

If you don't know Ryan Cummins, you absolutely need to make it a priority!


Having Ryan close our 'Health'care 2026 conference with a keynote address is going to be engaging and empowering

The work he's doing is absolutely incredible 

His curiosity to learn is unmatched

And his focus on future generations is inspiring.....


Don't miss an opportunity to hear from, and meet Ryan at 'Health'care 2026!

healthcare2026.com

#health #healthcare #business #ceo #entrepreneurship #events

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