Mark MacLeod

I help startup CEOs go from $5M in revenue to a massive exit

Since 1999, I have sat at the right-hand side of the leaders of high growth technology companies as either a CFO, VC or deal maker. I served as CFO for software companies including Shopify (NYSE: SHOP) and Freshbooks. 

I was a General Partner in Real Ventures, one of Canada's largest and most active seed stage funds. My investments there include the fund's largest cash on cash and highest IRR returns to date. 

Most recently, I founded SurePath Capital Partners the leading investment bank for SMB SaaS companies where we did hundreds of millions in financing and exit transactions.

The thing I loved most about these roles was the one on one coaching and advisory conversations I had with CEOs. 

Since 2020 I have been coaching, investing in and advising CEOs + helping them execute game-changing deals.

I am a semi-active angel investor with a portfolio of 22 investments, 2 highly positive exits and counting.

In my spare time, I am a passionate CrossFit athlete and electronic music producer/ DJ. I also run Deep Down Music, a record label.

Founder

I coach, advise and invest in the CEOs of high growth technology companies & help them execute game-changing deals.

The best CEOs I've worked with all have one thing in common: They're blunt.

Not rude. Not cruel. Not careless with their words.

Blunt.

They say what needs to be said in the room where it needs to be said.

They don't soften feedback until it loses its meaning.

They don't wait three months to have the conversation everyone knows is overdue.

They don't hide behind politeness when clarity is what the team actually needs.

Most founders confuse being nice with being kind.

Nice avoids the truth to protect feelings.

Kind delivers the truth because the stakes are too high not to.

Your team doesn't need you to be comfortable.

They need you to be clear.

Bluntness with respect is one of the highest-leverage leadership skills you can develop.

Subscribe to my newsletter and get a 22 page presentation on the secrets of Limitless CEOs https://lnkd.in/gWqQBd-n

Helping ambitious CEOs & founders scale world-changing companies without sacrificing their health, happiness, purpose, or humanity

No alternative text description for this image

I don't think I will ever fully retire.

Retirement is a concept built for a world that no longer exists.

It assumed you'd grind for 40 years, then stop.

Trade your health for money, then try to buy it back.

But what if you could work forever?

Not because you have to. Because you want to.

Because building still lights you up at 60, 70, 80.

That changes the entire equation.

You can't run this game like a sprint.

The founders who burned out at 45 didn't fail because they lacked talent. They failed because they built a pace they couldn't sustain.

We're going to live longer than any generation before us. The question isn't when you stop.

It's how you build a life and a body and a mind that lets you keep going as long as you choose.

That means sleep isn't optional. Recovery isn't weakness. Energy isn't something you sacrifice for the next milestone.

It's the asset that makes every future milestone possible.

Retirement is what happens when you run out of energy.

Sustainability is what happens when you never do.

Subscribe to my newsletter and get a 22 page presentation on the secrets of Limitless CEOs https://lnkd.in/gWqQBd-n

I am leaning into my weirdness, and it feels good.

I have never been a stereotypical CPA. When I was in undergrad, I designed my life around raves. Classes were Tuesday - Thursday. This enabled me to go dancing all night Saturday and recover. 

While I love to serve, I hate having a boss. So, while my peers went the “Big 4” route, I joined a small firm serving founders. I have only ever been or worked with founders. 

I have always leaned into what I love. I love to write. When I look back, all of my most important relationships came from my writing. Tobi from Shopify. Mike from FreshBooks. The guys starting Real Ventures. All came in part because they read my thoughts.

Then there’s yoga. Starting casually in my late 20s, yoga has evolved to become the foundation of my life.

The stretches offered in most North American yoga studios are a tiny fraction of what yoga is. In fact, the word “asana” (that’s what these postures are called) is barely mentioned in the Yoga Sutras.

Yoga is a complete system for living your life. My goal is to live every minute in accordance with yogic practices and values.

I discovered kundalini yoga in 2012. I got serious about it in 2019. And I teach it now.

Kundalini focuses on building and directing energy. We all have dormant energy at the base of our spine. Through these practices (called “kriyas”), we activate and direct that energy. 

Studies have shown that this practice turns on dormant parts of your brain. It unlocks our potential.

All of this mix of yoga, breathwork, meditation, and human optimization has co-mingled with my startup experience to create Limitless. 

My mission is simple: to redefine how founders build companies by putting their energy, health, and inner alignment first. So they can scale without limits and lead from a higher state.

Change your life so you can change the world!

Hard to think of something more motivating to work on!

Subscribe to my newsletter and get a 22 page presentation on the secrets of Limitless CEOs https://lnkd.in/gWqQBd-n

undefined undefined

Certified Personal & Business Performance Coach

Chartered Professional Accountant (CPA)

An exclusive community of VC and PE-backed CEOs who want
to scale themselves and their companies without limits.

Limitless is an exclusive community of VC and PE-backed CEOs who want
to scale themselves and their companies without limits.

I coach startup CEOs to grow themselves and their business all the way to a massive exit

SurePath Capital Partners is the premier strategic financial advisor to the global SMB Software market. With offices in Toronto and San Francisco, we aim to be the #1 advisor in this space globally and the one call CEOs and board make when they need to make a deal happen.

I led finance and corporate development at FreshBooks - the #1 cloud accounting specialist for small business owners. Since 2004, over 5 million people have used FreshBooks to track time, organize expenses and invoice clients online and in the cloud.

Accomplishments:
- Closed $30M institutional funding round + other unpublished transactions
- Led the process to find a partner to backstop a new product line
- Sourced and closed other key revenue-generating partnerships

CFO + Chief Corporate Development Officer

Venture Partner

Parter at Real Ventures where I focus on SaaS, freemium, e-commerce and digital media seed investments

Director, Fabric Technologies
Director, Context.io (sold to Return Path)
Director, Frank and Oak
Observer, Rewardli Inc.
Investor, Thinknear.com (sold to Telenav)
Investor, Localmind.com (sold to Airbnb)
Investor, Massive Damage Inc.
Director, Sweet IQ (sold to Reachlocal)
Observer, Unbounce.com
Investor, Engagio (sold to Influitive)
Investor, Origin.al Internet Company General Partner

General Partner

CFO for Tungle - a great solution for meeting coordination.

Raised a $5M "A" round. Served as CFO through the successful sale of the company to RIM.

Interim CFO, Shopify
Advisor, Well.ca
Advisor, Cakemail 
Advisor, Dok Dok Inc 
Advisor, Raymark
Advisor, Sitezoogle 
Interim CFO, Status.net Inc.

Advisor & CFO

Led finance, operations, legal, HR, strategic planning functions for this mobile communications startup. Raised an $10M B round led by Flybridge. Raised an additional $1M in China. Made major improvements to execution, ops, key metrics, etc.

Led finance, operations, customer support, IT and manufacturing for this venture-backed networked storage vendor. Negotiated the sale of Terrascale to Rackable Systems (NASDAQ: RACK) in a deal returning 10x on invested capital.

VP, Finance

Prepared this 15 person IP networking startup for commercialization & ‘B’ round funding. Responsibilities included financing, all back office operations, investor + board relations and negotiation of all  agreements. Towards the end of my term, I was given increasing responsibility for OEM sales and strategic relationships.

Strategic consulting assignments: 
•	Advised on the sale of two software companies and the purchase of an education services company
•	Led the successful restructuring of an insolvent retailer. The company is now thriving and expanding
•	Enabled the restructuring & strategic refocus of a new media company that resulted in a 3x growth in revenues and 5x growth in profit & cash flow

President

Was responsible for Finance, Alliances and Corporate Development functions. Raised $19M in equity over 2 rounds + oversaw growth to over 100 people. Established many key partner relationships

Director, Finance + Corporate Development

Helping VC-backed CEOs scale themselves and their companies without limits. 
| Host of The Startup CEO Show podcast

Marie Chevrier Schwartz spent 10 years building Sampler. Raised venture capital. Grew it to real scale. Then the business went bankrupt.

Most founders go dark when that happens. Marie did the opposite. She went on social media and told everyone.

The thing she said that stuck with me most: The day she accepted it was over, she felt relief. Not defeat. Relief.

Because she finally separated who she was from what she built.

That's the hardest thing in entrepreneurship. Not the fundraising. Not the product. Not the market timing.

It's realizing you are not your company.

Marie was late in her pregnancy when she learned the business wouldn't survive. She had a newborn when it officially ended. And instead of shutting down, she used that moment to rebuild her identity entirely.

She's went on to runTechTO, Canada's largest tech community, serving 60,000 founders. Different chapter. Same energy. More clarity.

If you missed the podcast, the full conversation is on my blog → link in the comments.

Most founder interviews are about fundraising, growth hacks, and exits.
This one was different.

I sat down with Tonya Papanikolov, founder of Rainbo, one of the leading functional mushroom brands. She's a holistic nutritionist, a Kundalini yoga teacher, and someone who built her company from a meditation download, not a pitch deck.

What struck me most was how she thinks about success.

Not revenue targets. Not market share.
Alignment. 

Is what she's building aligned with her deeper purpose? And when the answer is yes, everything else follows.

She also said something that stopped me: when she feels the urge to escape and retreat from the work, that's usually a sign she's avoiding the next level of growth, not that she needs rest.

That's a distinction most founders never make.

We talked about building a CPG brand from scratch, getting into Whole Foods, running a company with her husband, and why her morning practice is the most important thing she does for the business.

If you missed the podcast, the full conversation is on my blog

Botkeeper raised $90M+ and just shut down after 11 years. It's a cautionary tale we all can learn from.

Raising capital is not a sign of success. It just means someone gave you a shot.

We celebrate fundraising like it's the finish line. It's not. It's the starting gun.

And sometimes it's the thing that kills you.

More capital means more pressure, higher burn, bigger expectations, and less room to figure things out.

Botkeeper never nailed product-market fit with accountants. But they kept raising anyway. I don't blame them. But this happens a lot with VCs overfunding.

$90M later, the outcome was the same as if they'd run out of money at $5M.
Except that more people got hurt.

The founders I work with who build lasting companies treat capital as fuel for what's already working. Not a substitute for what isn't working.

The true test of your values isn't when you fire a low performer.
Everyone can do that.

It's when you exit a high performer who violates them.

The person who is hitting their numbers. The one the board loves. The one your team depends on.

But they're toxic. They undermine trust. They treat people like collateral damage.

And you know it.

Most CEOs tolerate it because the results are too good to lose.

That's not pragmatism. That's a signal to your entire company that values are negotiable when the numbers are right.

The moment you exit that person, two things happen.

First, it hurts. Revenue might dip. There's a gap.

Second, your culture becomes real. Every person on your team now knows the values aren't a poster on the wall. They're the operating system.

And that's worth more than any one performer.

Harry Stebbings says fundraising has changed.

According to Harry, SaaS founders growing 2-3x have two choices:

Use AI to accelerate to 8-10x growth. Or cut burn and never raise again.

The reality is more nuanced.

The real question isn't "which path." It's "how do I build OPTIONALITY so I can choose either, on my terms?"

Optionality has never been more important than it is now.

Optionality means:

✅ Your can get to cashflow break-even in runway if you are not there already.

✅ Your growth rate & unit economics let you raise if and when you want to.

✅You are known to your most natural buyers and can enter into a warm, qualified exit process at any time.

And a personal consideration here: 

✅ As founder, your energy and clarity let you make that strategic call from strength, not panic.

The founders who win in this market aren't picking door 1 or door 2.

They're building a company, and a version of themselves, that can walk through whichever door makes sense, whenever it makes sense.

That's not simple. But it's the real game.

Founder @ 20VC

The biggest risk of AI isn't losing your job. It's never being able to stop working.

The people burning out fastest right now aren't the ones resisting AI.
They're the ones who embrace it most.

A new Harvard Business Review study followed a tech company for eight months and found that when people genuinely adopted AI, they didn't work less. They just did more. 

To-do lists expanded to fill every hour that AI freed up, then kept going. 

Work bled into lunches and late evenings. Not because anyone was pressured. Because the tools made it more doable.

This is the trap nobody's talking about.

AI doesn't create boundaries. It removes them.

And without boundaries, more capacity just becomes more work.

This is why health, energy, and inner clarity aren't nice-to-haves in the AI era.
They're survival tools.

The founders who thrive through this won't be the ones who squeezed the most out of every AI tool.

They'll be the ones who knew when to stop. Who protected their sleep. Who built recovery into their operating system. Who had the self-awareness to say 
"I can do more," and the discipline to say "but I won't."

Being able to call it a day and feel good about what you accomplished will become a superpower (it always was..).

AI is the most powerful accelerant founders have ever had.

Without boundaries, it accelerates burnout just as fast as growth.

Your job as CEO isn't to do more. It's to remove friction.

Friction is everywhere. It's the slow approval process. The unclear ownership. The meeting that should be an email. The hire you haven't made. The conversation you've been avoiding.

It's not one big thing. It's a hundred small things quietly dragging your company down.

Most founders tolerate them. They work around them. They get used to the drag.

Limitless CEOs have a different habit.

They remove one piece of friction every single day.

It sounds small. But compounded over a quarter, that's 90 obstacles gone.
Over a year, you've fundamentally changed how your company operates.

Not through a big reorg. Not through a new strategy deck.

Through the daily discipline of making things a little easier for your team to win.

That's the real job.

Find and remove one piece of friction every day.

AI made you faster. It didn't make you better at stopping.

Every CEO I speak with has the same problem right now: the tools keep getting better, but the days keep getting fuller.

So I teach them a simple boundary protocol: Block one hour a day that is completely analog.

No screens. No Slack. No AI. No input at all.

Walk. Breathe. Sit. Think. Or do nothing.

This isn't a wellness hack. It's an operating decision.

Because the quality of your leadership is determined in the space between inputs. Not during them.

The founders who protect that space make sharper calls, see further ahead, and last longer than the ones running at full capacity every waking hour.

Your brain needs time offline to process what it's taken in. Without that, you're not thinking. You're just reacting faster.

AI gives you speed. Analog time gives you clarity.

You need both. Most founders only have one.

I asked a CEO client to rate his happiness. He said 6 out of 10.
I asked what would make it a 10.

His answer wasn't more revenue. Wasn't a bigger team. Wasn't closing a round.
It was spending more time on things that create energy.

He already knew the answer. Most founders do.

The gap between a 6 and a 10 isn't more success.

It's less of what drains you and more of what fills you up.

The hard part isn't knowing this. It's giving yourself permission to act on it.

Energy isn't a reward for building something great. It's the requirement.

Design your role, company and life around energy and you become limitless!

Every startup's 2026 budget is already wrong.

Not because someone made a mistake.

Because AI is changing the cost structure faster than anyone can model.

Roles you planned to hire for in Q3 might not be needed by then.

Tools that cost six figures are being replaced by agents that cost hundreds.

Runway is quietly extending at companies that are paying attention.

And the ones that aren't are still hiring against a plan that was outdated the week it was approved.

This is the new reality for founders:

You can't forecast spend the way you used to.

The old was was full of certainty. Full of proven formulas. 

The founders who adapt fastest aren't the ones with the best financial models.

They're the ones willing to revisit assumptions every month, rather than every quarter or every year.

Rigid budgets were already dangerous. In the AI era, they're fiction.

Subscribe to my newsletter and get a 22 page presentation on the secrets of Limitless CEOs https://lnkd.in/gWqQBd-n

Most founders optimize their GTM funnel. Almost none optimize the machine that runs it all.

I recently sat down with Greg Newlands, a fitness coach who works with founders.

Full disclosure: Greg is my coach and also works with several of our Limitless founders.

One thing he said stuck with me:

"If I'm not sleeping well, not exercising, not rested, I just don't perform the same in life or in business."

That's not a wellness quote. That's an operating reality.

Greg trains entrepreneurs the way athletes get trained: 
Strategic breaks throughout the day. 
Resistance training as a non-negotiable. 
Tracking four daily KPIs for energy and performance.

The part that hit hardest: he burned out multiple times before he stopped treating rest as the enemy of progress.

Sound familiar?

This is one of the most tactical conversations I've had on health as a founder strategy.

Full episode on my blog → link in comments.

From your biggest → the best shape of your life | Helping ambitious, driven men rebuild their body & confidence after letting things slip

Jack Dorsey, founder of Twitter and Block, just gave us a lesson in making hard decisions.

Often, when faced with decisions like layoffs, the temptation is to do the minimum necessary. To avoid as much pain as possible. 

Jack did the opposite. He leaned into the pain. He cut 40% of Block's workforce. Over 4,000 people. In one move.

Not because the business is struggling. Gross profit grew 24% last year.

He did it because he saw where AI is heading and decided to get there first. He leaned in.

Dorsey said it clearly: “Repeated rounds of cuts destroy morale, focus, and trust.” He'd rather take one hard, clear action than manage a slow bleed toward the same outcome.

You can disagree with the decision. But the leadership principle is worth studying.

The hardest decisions aren't hard because you don't know what to do. They're hard because you don't want to feel the pain of doing it. They're hard because you resist.

So you delay. You half-measure. You spread the pain out over months, hoping it hurts less.

It doesn't. It just hurts longer.

Whether it's a layoff, a co-founder conversation, or a pivot you've been avoiding, the cost of the slow path is almost always higher than the cost of the decisive one.

Suffering = pain * resistance. If you don’t resist what you need to do, you will not suffer. 

It’s no surprise that Jack took this approach, given his spiritual practice. Jack does long Vipassana retreats. Anyone who has done these will know that they are painful but always worth it.

The way out (of whatever issue you are struggling with) is through. Lean into the discomfort. Make the bold call.

A founder built an AI system that scans everything. It was making him worse at his job.

AI lets you measure everything now. Every Gong call. Every Slack thread. Every data query. Every customer conversation.

One founder I spoke with built an AI system that scans a thousand times more data than his team could manually. Every day, he is briefed on literally everything in his company.

Impressive. Also dangerous.

Because the ability to do everything is not a reason to do everything.

When I dug in, his real bottleneck was one thing. So we cut one of three product initiatives entirely. Narrowed focus to the one thing blocking growth.

More data didn't solve it. Less did.

Here's what I see happening everywhere right now:

AI gives founders superhuman capacity to monitor, measure, and manage.

But capacity without focus is just sophisticated distraction.

The founders who win won't be the ones who do the most with AI.

They'll be the ones disciplined enough to do less.

The mind is a wonderful servant but a terrible master.

For most founders, the mind is running the show.

It wakes you up at 3 am with worst-case scenarios.

It replays the board meeting you can't change.

It tells you that every competitor is ahead of you.

It convinces you that rest is laziness.

The founders I work with at Limitless are learning to think with more intention.

They choose what to focus on rather than letting their minds choose for them.

That's what meditation is. That's what journaling is. That's what a morning practice is.

Not escaping the mind. Training it to work for you, not against you.

You are a mental athlete. You need to train your mind the way athletes train their bodies.

Your mind built your company. Don't let it destroy you in the process.

Every founder has a financial dashboard. Almost none have a biological one.

At Limitless, we think about CEO performance across three dimensions:

Physical → sleep quality, HRV, recovery.

Mental → deep work hours, focus time.

Financial → MRR, pipeline velocity, growth.

(We also go deep on spiritual, but let's park that for now...).

Here's what most founders miss:
These aren't three separate dashboards. They're one system.

✅ Your HRV predicts your decision quality.

✅ Your sleep predicts your deep work capacity.

✅ Your deep work predicts your revenue.

The financial metrics are the output. The biological ones are the input.

Fix the inputs. The outputs follow.

Every playbook you relied on is being rewritten right now.

AI is disrupting how we build, hire, sell, and lead.

The best practices that got you here? Most of them no longer apply.

This is terrifying if you need external certainty to make decisions.
It's freeing if you don't.

When the map is gone, the founder who wins is the one who can navigate without it.

That means first principles over borrowed frameworks. Grounded decisions over reactive ones. Intuition over consensus.

Your own race over someone else's example.

The answers aren't in the latest AI playbook or the hottest thread on X.

They're inside the founder who is clear enough, calm enough, and honest enough to hear them.

This is the era where inner work becomes a competitive advantage.

I meditate every morning before I open my laptop.

Not just because I'm spiritual. Because it makes me a better decision-maker.

When your mind is full of noise, every decision feels urgent. Everything looks like a fire. You react instead of respond.

When your mind is clear, you see what actually matters. You hear the signal through the noise. You trust yourself enough to act without needing five people to validate the call.

The best CEOs I work with are the clearest.

That clarity comes from creating space between the input and the response.

That's all meditation is. Not woo-woo. Not escape.

A daily practice of training your mind to be still so it can be sharp when it matters.

You are a mental athlete. You need to train your mind the way athletes train their bodies.

Ten minutes a day. No app required. Just you and silence. Pay attention to your breath. As distractions arise, keep coming back to the breath. That's it.

It's the highest-ROI habit no one puts on their calendar.

Subscribe to my newsletter and get a 22 page presentation on the secrets of Limitless CEOs https://lnkd.in/gWqQBd-n

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

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.

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

I have big news. But first, a story. 

I talk with founders every day who are in the middle of real inflection points.

Co-founder splits. Post-exit identity crises. Scaling without burning out. The weight of figuring out who they are as a leader.

But I only coach 15 people at a time, which means I can't work with most of the founders I speak with.

That's always bothered me, so we're doing something about it.

Introducing: Inside-Out Virtual Workshops.

Small (around 8 people). Led by me and the Inside-Out team using the same frameworks and modalities we use with our 1-1 clients, finally accessible to a broader group of founders.

The first workshop is Getting Unstuck. It's for the founder or exec who knows how to do hard things, but keeps hitting the same wall in one specific area.

Most approaches to this work outside-in: Better habits, tighter systems, more accountability. And if that's worked for you, great. But if you've tried all that and you're still stuck, the problem probably isn't discipline.

This workshop works from the inside-out, using IFS (Internal Family Systems), an evidence-based framework that has become one of the most powerful tools in serious executive coaching.

Give me 90 minutes. You'll leave with a new way of seeing the stuckness and a concrete experiment to take into your life.

WHEN: March 23rd. Noon to 1:30pm ET.
COST: Free

Space is very limited. Click the link in the comments if you'd like to apply.

"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.

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.

A client told me: “The single most important thing for my company right now is the fundraise.”

Then he paused. “And it’s the thing I avoid every morning.”

I see founders in inner conflicts like this every day. This type of dynamic can take years to unwind, and kill companies and relationships along the way. 

After nearly a decade of coaching founders, I've found one reliable method for resolving inner conflicts like these: 

Internal Family Systems, or IFS. 

IFS is a leading toolset at the bleeding edge of exec coaching, and is built on the only scientifically proven method to change emotional learnings, Memory Reconsolidation.

It's a core tool in our practice at Inside-Out, and we're teaching founders how to use it themselves live on March 23. 

When we looked inside at this particular issue, we found two competing parts.

One part wanted the company to grow. The other part said, “If this fails, you’ll look like an idiot in front of your investors.” So we work on the problematic part. Once you do that, the system stops conflicting.

This doesn't take weeks of months. The best coaches help clients get unstuck in an hour or less. 

Want to learn how it works? Apply for our first intimate workshop on March 23. Application in comments.

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.

Most people have picked a side on AI.
Either it's the greatest tool ever built, or it's an existential threat we're sleepwalking into.

The binary is comfortable. But the leaders I work with who are navigating this most
effectively have learned to hold something harder: Both.

The fear is real. It lives in the gut. It wakes you up at 3am thinking about the world your kids will inherit. The excitement is equally real. As it should be.

The mistake isn't feeling one or the other. The mistake is collapsing into one becausethe other is too uncomfortable to carry. 

The most important things in life are paradoxical. They resist resolution. And AI may be the defining paradox of our time.

As F. Scott Fitzgerald said, "The test of a first-rate intelligence is the ability to hold two opposing ideas in mind at the same time and still retain the ability to function."

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

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

One late night, I got a call from a board member.

It was around 11pm my time, which means it was probably 3am his time.

What he said stuck with me forever.

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.

Control is the most expensive illusion in your company.

My Zen teacher used to tell me, “Sit down, hold everything still, and watch what moves.”
What moves is everything you don't control. Your thoughts arrive uninvited. Your
emotions surface without permission. The narrative you've built about agency begins to
quietly unravel.

AI is doing something similar at civilizational scale. It moves too fast, builds too
suddenly, disrupts too completely to let you maintain the fiction. But I've come to believe that confrontation is a gift.

The founders who thrive aren't the ones who reassert control in the face of uncertainty.

They're the ones who find a different relationship to power, one that doesn't require control as its foundation.

That's not passivity. It’s a more sophisticated form of strength.

"You have power over your mind, not outside events. Realize this, and you will find strength." — Marcus Aurelius

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

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

Scaling a company means giving away the work you used to take pride in.

Watch and listen to why that moment is harder than most founders expect.

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

taplio

The Battle

Mark MacLeod

Ryan H. Vaughn

Followers

Posts

Engagements

Likes

Performance ScoreMark MacLeod's LinkedIn Performance

Performance ScoreRyan H. Vaughn's LinkedIn Performance

Ready to grow your LinkedIn presence?

taplio

The Battle

Mark MacLeod

Ryan H. Vaughn

Followers

Posts

Engagements

Likes

Performance Score.css-goub6s{font-size:var(--chakra-fontSizes-md);font-weight:500;color:var(--chakra-colors-gray-600);display:block;margin-top:var(--chakra-space-1);}Mark MacLeod's LinkedIn Performance

Performance ScoreRyan H. Vaughn's LinkedIn Performance

Ready to grow your LinkedIn presence?

Performance ScoreMark MacLeod's LinkedIn Performance