Mark MacLeod

Limitless.ceo

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

Founder

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

SurePath Capital Partners

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.

FreshBooks

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- Closed $30M institutional funding round + other unpublished transactions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

Real Ventures

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

Tungle Corporation

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.

SaaS, E-commerce, Marketplace companies

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

Advisor & CFO

Mobivox

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.

Terrascale Technologies Inc.

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

Hexago

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.

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.

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

The Tokyo Test.

Before I hire anyone or partner with a VC, I ask myself one question:

Would I be excited to sit beside this person on a 14-hour flight to Tokyo?

If the answer is no, I pass.

Life is too short to work with people you don't actually like.

Skills matter. Chemistry matters more.

Use the Tokyo Test.

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

The most senior person in the room uses the fewest words.

Junior: 10 slides to explain the problem
Mid-level: 5 slides with bullet points
Senior: "We have a cash flow issue. Here are three options."

Brevity isn't about being short. It's about being clear.

It means you've done the hard work of:
- Cutting through the noise
- Identifying what actually matters
- Removing your own confusion first

If you can't explain it simply, you don't understand it yet.

Watch how the best CEOs communicate:
- They get to the point
- They don't hedge with qualifiers
- They don't need jargon to sound smart

The CEO who says "Revenue is down, we need to cut 15% of headcount by Friday" is more senior than the one who sends a 2000-word memo about "organizational optimization initiatives."

You earn seniority when you stop needing extra words to feel credible.

Complexity is easy. Clarity is hard.

If you want to level up, start cutting.

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

Bryn Jones grew PartnerStack for 4 straight years at 100% growth.

Most founders dream of that problem.

He told me it nearly broke him.

His insight: "Growth solves everything. Except it solves everything by letting you ignore problems.

You can only pave over so many cracks before the whole thing collapses.

The wildest part? Fixing those problems after Tech Winter hit was the most fulfilling work of his career. More than the hypergrowth years.

If you missed my podcast with Bryn, here is the interview. We cover:
Also in this conversation:
✅  How being on Canada's national swim team prepared him for 10 years as a CEO
✅  Why most partnerships fail despite their potential
✅  The one question that determines if a partnership will work
✅  Why he ignored his instinct and what happened next

Read it here:

Open article: PartnerStack's CEO Bryn Jones on 10 Years of Building B2B Partnership Networks and Why Growth Nearly Broke Him - Mark MacLeod by markmacleod.me

PartnerStack's CEO Bryn Jones on 10 Years of Building B2B Partnership Networks and Why Growth Nearly Broke Him - Mark MacLeod

Work hard. Play hard. Sleep hard.

This is my mantra.

Work hard: Anything worth doing is never easy. You need to push.

Play hard: Play makes life worth living. Most CEOs think this is a post-exit luxury. I disagree. For me, "play" is music and yoga. Non-negotiables.

Sleep hard: Another thing many CEOs skip. To show up as your best self and crush without burning out, you need to sleep like it's your job.

You are a mental athlete. Athletes sleep like it's their job.

Nobody is thinking about you.

Seriously.

Your competitor? Too busy with their own problems.

Your team? Thinking about their own issues.

Your board? Looking at the numbers, not judging you as a person.

The brutal truth: You're not the main character in anyone's story but your own.

So why are you making decisions based on what "they" might think?

❌ Holding back on that bold strategy
❌ Overthinking that honest conversation
❌  Not sharing your real challenges

Your anxiety about perception is burning energy that you need for  building.

The CEOs who scale fastest realize that only results matter. Not optics. Not opinions. 

Make the call. Say the thing. Take the risk.

They're all too busy worrying about what YOU think of them.

If your direct reports drain you, you have the wrong people.

Or you're doing their job for them.

I see this constantly with the CEOs.

❌  They finish a day of back-to-back 1-on-1s and they're exhausted.

❌  They spend more time fixing their team's work than doing their own.

❌  They dread certain meetings because they know it'll be them solving problems again. Or a certain team member just saps them of energy.

Here's what should happen instead:

✅  Your direct reports should energize you.

✅  You should leave your 1-on-1s thinking "damn, I'm glad they're on this team."

✅  You should feel excited about what they're building, not anxious about cleaning up their mess.

✅ You should get ideas from them, not just give them.

If that's not happening, there are only two reasons:

1. You hired wrong
2. You're not letting go

Hiring wrong is fixable. Make the change.

Not letting go is also fixable, but it requires you to change.

Stop jumping in to save the day. Stop being the one with all the answers.

Build systems. Train properly. Then trust.

Sometimes you need to watch things break to learn where the system needs fixing.

You can't scale a company where everything runs through you.

And you definitely can't sustain it.

Your team should multiply your energy, not divide it.

If they're not doing that, something needs to change. 

P.S.
This was my all star team at SurePath Capital. Each and every team member gave me enery and leverage.

This is the story of how a tax law professor built a $30M ARR company while still teaching classes.
 
Benjamin Alarie is the CEO of Blue J Legal AND a professor at U of Toronto law school.
 
He saw AI coming for the legal profession in 2011. Had a choice: watch it happen or build the future himself.
 
The kicker? He's not a software engineer. His co-founder moved from Australia because of a childhood friendship.
 
They started in 2015. Spent 7 years building with supervised machine learning. Then LLMs hit. They pivoted hard in 2023.
 
Now: 300%+ YoY growth. 10 new logos daily. Approaching $30M ARR.
 
The lesson isn't about AI or tax law.
 
It's about recognizing when your deep domain expertise intersects with massive technological shifts.
 
Ben knew tax research was painful because he'd lived it for thousands of hours. He could see exactly what needed to exist.
 
Most professors would write another paper. He built a company.
 
We talked about:
✅ Managing investors while maintaining an academic career
✅ Enterprise sales when your TAM is basically the Big 4
✅ Why LLMs changed everything
✅ The $500B tax compliance market nobody thinks about
 
Link in comments.

The new CEO flex: Your sleep score.

Remember when pulling all-nighters was a badge of honour?

That doesn't scale. It just makes it harder for you to build your company.

Elite performers know: sleep is performance.

8 hours. 90% sleep score. REM cycles optimized.

That's the real flex.

You're a mental athlete running a company worth millions.

Sleep like your business depends on it.

Because it does.

No small plans.

It takes the same effort to hit "achievable" targets as it does for "crazy" targets.

Same meetings. Same strategic planning. Same team-building.

The only difference? Your ambition.

Most CEOs set targets they know they can hit. Safe. Predictable. Boring. They do this so they can tell their investors they are "on plan".

As you get ready for 2026, consider setting seemingly impossible targets.

Google was famous for this with it's moonshot thinking.

Hitting 60% of a moonshot target may be much better than hitting 100% of an achievable target.

Early stage VC: "We make 30 bets a year. Let's take a shot."

Growth stage VC: "We make 3 bets a year. Prove everything."

This is the shift founders don't see coming.

Seed investors are building a portfolio. If 1 in 10 works, they win. They can afford leaps of faith.

Growth investors are making concentrated bets. If 1 in 3 fails, their fund is cooked. They can't afford to be wrong.

So they need:
✅  Three years of consistent revenue growth
✅  Proof of unit economics
✅  Evidence of repeatability
✅  Clear path to exit

They're not being difficult. They're being rational.

Your Series A took 20 conversations.
Your Series C will take 200.

The math is simple:
- Early stage: high volume, high failure tolerance
- Late stage: low volume, low failure tolerance

Build your pipeline accordingly.

If you're raising growth stage capital with a seed stage pipeline strategy, you're going to run out of runway before you find your lead. Growth investors want to track you for a long time before they invest. No FOMO decisions.

Don't get bitter. Get realistic. 

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

P.S.
here's a random photo of me at the Calgary Stampede back when I was a VC. Cowboy hats are underrated

You can't see the system when you're inside it.

Your best thinking happens when you step out of the environment that created your current thinking.

Today I am joining Adrian Salamunovic to kick off the first Limitless Unconference in Tulum.

A group of ambitious humans are arriving. All builders. All on the go.

The goal is to reset. Take a breath. Take stock of what’s working and not. In our companies and our lives.

To engage in healing breath work and movement. To gain clarity and set our commitments and dreams for 2026.

I use retreats as a way to recharge, reset and recommit every year. My goal is to have one big retreat per year and 3 small ones.

This gives me perspective and direction. I slow down to speed up.

CEOs who build for the long term don't just work hard. They build in time to step back. Quarterly. Monthly. However often you need it.

Because perspective isn't found in the grind.

It's found when you finally stop grinding.

When you lose your health, you realize nothing else matters.

So many CEOs that come to me for coaching are killing themselves and can't keep up.

In this video Robbie Bent co-founder and CEO of Othership gets real about his journey. See comments for the full conversation.

P.S.
If you want to build a market-leading company without sacrificing your health, come join us at Limitless (see my featured post for the link)

Open video: ✂️ The CEO role will kill you on youtube.com

Want to 10x your company? Start by 10x'ing your capacity.

You can't scale what you haven't built in yourself first.

I see CEOs obsessing over growth hacks, fundraising strategies, and hiring plans.

But they ignore the most important variable: themselves.

Your energy. Your focus. Your ability to handle stress. Your decision-making under pressure.

Most founders hit a ceiling not because their market is too small or their product is wrong.

They hit a ceiling because they've maxed out their personal operating system.

The tree grows tall because its roots go deep.

Your company will only rise as high as your foundation is solid.

This means: sleep, exercise, mental health, relationships, nervous system regulation.

The boring stuff that everyone skips.

The biggest outcomes are founder-led. Always have been.

Zuck. Bezos. Jobs. Musk.

They didn't just build companies. They built themselves into people capable of leading those companies.

Stay grounded while you build.

Invest in your foundation as aggressively as you invest in your business.

That's how you become limitless.

Here's why meditation feels scary (at first)

The moment you sit down, the noise starts. Not around you—inside you.

You suddenly notice how busy your mind is. Thoughts. Loops. Worries. Stories.
It’s a lot.

But here’s the truth: that chaos was already there. You’ve just been working so hard to think clearly through it. This is why you're so exhausted. Why you can't think clearly.

Imagine how much energy you’d reclaim if your mind was actually clear.

Meditation shows you the mess then helps you clean it up.

Yes, it’s uncomfortable at first.

But on the other side? Clarity. Presence. Power.

Sit anyway.

The peace you’re seeking is already within you.
✨

Ryan Rouse

MALK Organics

President

Self Employed

Growth Advisor

HighKey 

Chief Executive Officer (acquired)

Board Member

Chief Marketing & Ecommerce Officer

Tasseo Consumer Ecosystem

Operating Partner

Serenity Kids

Head of Growth

Factor_

Co-Founder (Acquired by Hello Fresh)

Chief Marketing Officer

Chief Operating Officer

Merrill Lynch

Vice President of Sales

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. 

We've normalized something insane.

Two people typing at each other for 35 minutes.

Typing gives us time to be clever. To craft the perfect comeback. To sound right while being wrong.

Talking forces us to be human.

No edit button. No screenshots for later. No audience watching you perform.

Just two people working it out in real time.

The friction you feel before picking up the phone and calling?

That's your ego protecting itself.

It knows the keyboard is safer.

But relationships aren't built in safety.

They're built in the messy, unedited moments when you actually hear someone's voice.

Next time you're about to send that long message?

Pick up the phone instead.

You'll be shocked how fast "enemies" become teammates when you remove the screen between you.

~~~~~~~~~~~~~

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Never Been on a Forbes List | President at MALK Organics | Daddy at Rouse House | Previously: Co-Founder & CMO at Factor_, CEO at Highkey

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The startup world worships charisma.

Big personalities. Bold promises. Slick pitches.

But I've watched too many charismatic founders flame out.

And too many quiet operators build empires.

Here's what I learned:

Charisma opens doors. Character keeps them open.

Charisma raises the round. Character delivers the returns.

The market rewards charisma in the short term. But it pays character in the long run.

Use your charisma to sell the vision.
Use your character to build the business.

I'm curious: Think about the best leader you've ever worked with.

Were they the most charismatic person in the room, or did they have something deeper that made you follow them?


~~~~~~~~~~~~~

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The more polished your corporate language, the less your employees believe a word you say.

Early in my startup career, I'd craft these perfect all-hands emails. 

"We're excited to announce strategic realignment initiatives that will optimize our organizational effectiveness."

Translation: We're laying people off.

My team saw right through it.

And it created distrust and disengagement.

So I changed my approach.

Instead of "pursuing growth opportunities," I started saying "we're trying something new and honestly, we're not sure if it'll work."

Instead of "navigating headwinds," I said "this quarter sucked and here's why."

It was uncomfortable at first.

But the team started asking real questions instead of nodding politely.

And they started to trust me more when things got hard because they knew I wouldn't sugarcoat it.

I remember the first time I told my team "I don't have a good answer for that yet" in a meeting. 

Someone was brave enough to say "thank you for not making something up."

People don't want perfect messaging from their leaders.

They want honest communication about what's really happening and how it affects them.

Even if you don't know. 

Your team can handle the truth. 

What they can't handle is being treated like they're too naive to see through corporate BS. 

Every euphemism you use is a withdrawal from the trust bank.

And that account doesn't have overdraft protection.

There's no finish line where suddenly you feel like you made it.

No magic number that makes the doubt disappear.

No age where you finally stop comparing yourself to the 28-year-old who just raised $50M.

We're all out here pretending we're on schedule while secretly terrified we're falling behind.

The woman who sold at 32 thinks he peaked too early.

The guy grinding at 50 thinks she started too late.

The kid raising millions thinks he's a fraud.

None of us know what we're doing.

We're just making different mistakes at different speeds.

Your career isn't late.

It's not early either.

It's just yours.

And the only way to lose is to stop showing up because you think you missed some imaginary deadline.

Keep building.


~~~~~~~~~~~~~

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The biggest sales job you'll ever make isn't to your customers.

It's to yourself.

Because it's the stories in your head determine the stories you tell the world.

If you're telling yourself you're an imposter, that's exactly what you'll project in every meeting.

If you're telling yourself you're not a "numbers person," guess what? You won't be.

If you're telling yourself you need one more certification, one more mentor, one more anything before you're ready...

You're right. You'll never be ready.

Because readiness isn't something you acquire.

It's something you decide.

The most successful people I know aren't the ones with the best credentials or the smoothest pitch.

They're the ones who changed their internal narrative first.

From "I'm figuring it out" to "I know my shit."
From "I hope this works" to "Watch me make this work."
From "I'm not that type of person" to "I'm becoming that type of person right now."

Your business can only grow as fast as your self-concept allows.

Change the story. Change everything.


~~~~~~~~~~~~~

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Every morning at 5:30 AM, my alarm goes off.

And I have a choice.

Hit snooze and skip my workout, or get up and move.

That's the first battle of the day.

Success isn't some climactic moment where everything falls into place.

It's winning thousands of these small fights. Day after day.

The decision to kill a product you spent 18 months developing because it clearly doesn't work. 

The discipline to skip the third glass of wine at dinner so you can think more clearly in tomorrow's meeting.

The courage to fire someone who's good but not great.

There is no one final battle.

No last job.

No riding off into the sunset.

These micro battles never stop.

And the moment you accept that?

The pressure to "arrive" disappears.

You stop waiting for some future version of success.

You start finding it in the discipline of showing up when it's hard.

In choosing the right move over the easy one.

In winning today's battles so you're ready for tomorrow's.

~~~~~~~~~~~~~

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What if choosing not to be offended was the most powerful decision you could make today?

Most leaders don't realize they're handing control of their day to people who don't matter.

I've spent 15+ years in executive roles. Built teams. Navigated acquisitions. Raised 3 kids.

Many years ago, someone's criticism would completely derail me.

I'd stew on it for hours.  

But that person? Living their life. Completely unbothered.

The only person suffering was me.

It made me recognize that offense is a choice.

Not a reflex. A choice.

Now when someone tries to push my buttons, I pause and choose whether or not to engage. And how to engage if I choose to. 

I'm protecting what matters: me.

Your reaction gives other people control over your day.

Your non-reaction or calm reaction gives you back your power.

So here's my question:

Who are you letting live in your head that doesn't deserve to be there?


~~~~~~~~~~~~~

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Being late to every meeting isn't a personality quirk. 

It's a character flaw. 

And it's costing you more than you think. 

It's like your friend who couldn't handle their alcohol and had to be baby sat every night. At first everyone's like "Oh, that's just Jeff/Julie."'

But you know what happened over time? Less and less people hung out with Jeff and Julie. 

Same goes here. 

Every time you're late to a meeting, you're showing showing people you can't be trusted with the small things.

Trust with the small things leads to trust with the big ones.

The opportunities that require trust:
- Leading a team
- Managing a budget
- Representing the company
- Taking on a big project

None of those happen if people don't trust you with the basics.

And being on time is the most basic thing there is.


~~~~~~~~~~~~~

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I've watched good companies crumble from the inside out.

Not because of market conditions or bad products.

Because they let weak leadership linger.

Your team sees it before you do.

And every day you wait, they lose a little more belief.

Not just in that one leader.

In you. In the vision. In whether any of it matters.

The damage compounds faster than you think.

And by the time it's obvious to you, half your best people are already mentally checked out.

So when you know someone isn't cutting it, act.

Yes, transitions are messy.

Yes, there will be short-term pain.

But nothing restores faith in a team faster than watching leadership actually lead.

I've never been the smartest person in the room.

But I have been the most dangerous.

Not because I know more.

Because I know less.

My first few months at MALK, I was like a broken record.

"What's the reason for that?"
"Who decided this?"
"What happens if we skip it?"

I've done the same thing at business I get involved with. 

Turns out, most companies run on autopilot.

Someone built a process years ago because they needed something fast.
It stuck.

Not because it was good.

Because it was there.

Your processes aren't best practices.

They're fossils.

Fresh eyes see the waste you've gone blind to.
Here's what works:

Hire people with fresh eyes. 

Give them permission to be annoying.

Let them question everything.

Document every "why?"

Most answers will be "I don't know" or "that's just how it's done."

That's your gold mine.

Each "I don't know" is money left on the table.

Each "that's how we've always done it" is a process begging to be killed.

What process exists at your company only because "that's how it's always been done"?

~~~~~~~~~~~~~

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The cost of handing out fancy titles too soon is real. 

Early on at Factor_, we couldn't afford top talent.

So we did what a lot of founders do.

We gave people VP and Director titles to make up for the salary gap.

Seemed smart at the time.

They got the prestige. We saved cash.

But a title doesn't teach someone how to do the job.

It doesn't give them the reps. The pattern recognition. The instincts that come from years on the job.

And when you realize someone isn't ready for the role they're in, you've got a real problem.

Because now you can't just adjust their responsibilities.

You have to demote them or move them out.

Which is brutal for everyone involved.

The title that was supposed to solve a problem becomes the problem.

Looking back now, I wish I'd been straight with people about where they actually were.

Not where I needed them to be.

Give them a role they can handle today. 

Let them earn the next one.

~~~~~~~~~~~~~

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Everyone's building a personal brand. But personal credibility should be the goal. 

I see it every day.

People obsessing over their LinkedIn banner design while their actual work speaks nothing.

Crafting the perfect thought leader bio while delivering mediocre results.

Posting motivational quotes they don't live by.

Here's what they don't get:

Personal brand is what you tell people you are.
Personal credibility is what you prove you are.

One is manufactured. The other is earned.

You can buy a personal brand. Hire a ghostwriter. Use AI to pump out content. Get those vanity metrics up.

But credibility?

That comes from one place: Doing.

Delivering on promises when nobody's watching.
Admitting when you're wrong instead of doubling down.
Sharing real failures, not just humble brags disguised as lessons.

The most credible people I know barely think about their "brand."

They're too busy actually building things. Solving problems. Creating value.

Their reputation spreads through whisper networks, not viral posts.

Want to stand out in 2025?

Stop polishing your image.
Start delivering results.

Because at the end of the day, your personal brand is just marketing.

Your personal credibility is your actual product.

And people can smell the difference from a mile away.

~~~~~~~~~~~~~

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Being a 6/10 across many functions will serve you more than being a 10/10 in one.

But you typically have to get to a 9/10 in one area to earn the opportunity to oversee the others. 

The hard part for most people is being comfortable going from a 9/10 in something down to a 6/10 in order to create time to go from a 2/10 to a 6/10 in the others.

They can’t let go of being best in class at the one thing. 

Which limits their ability to to lead.

~~~~~~~~~~~~~

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You survived the launch. You got early traction.

So why does year three feel harder than year one?

Because in year one, you'd work 24/7 and love it.

The adrenaline was real. Every win felt like validation.

You didn't need sleep. You didn't need breaks.

You had rocket fuel in your veins.

But years 2-5...

The adrenaline runs out.

And when it does, the grinding reality sets in.

34.4% of founders experience burnout.

Not in year one when you're supposed to be struggling.

In years 2-5, when you're supposed to have it figured out.

Year one, you're running on pure excitement and fear.

That combination keeps you moving even when you're exhausted.

But years 2-5? That's when the wheels come off.

The excitement fades. The fear becomes background noise.

What's left is just the grind.

No finish line in sight.

Revenue looks healthy. Team is growing.

But you're running on empty.

And you don't realize it's happening.

You think you're just tired. You think it's a rough month.

You tell yourself you'll take a break soon.

But soon never comes.

Because now you've got:

• A team depending on you
• Investors expecting growth
• Customers needing support
• A reputation to protect

You can't just stop anymore.

The thing about founder burnout is it doesn't announce itself.

It shows up in small ways first.

You start dreading Monday mornings.

Emails sit unread for days.

Decision-making gets harder.

Your patience with your team gets thinner.

Then one day you wake up and realize: You don't remember the last time you felt excited about this.

The data backs this up.

Founders in their middle years report higher rates of anxiety and depression than in year one.

Not because things are going worse.

Because things are going exactly as expected.

And that's somehow harder to handle than the chaos.

If you're in those middle years right now, here's what I'd tell you:

The 24/7 hustle isn't sustainable.

It never was.

Year one, you could get away with it because the adrenaline covered the cost.

But you can't run a marathon on sprint energy.

And building a lasting company is a marathon.

Take the break. Build the boundaries. Protect your mental health.

Not because it's nice to have.

Because your business won't survive if you don't.

I spend my days analyzing consumer behavior, market trends, etc.

But my wife always points out something I completely missed.

Last month, we were arguing about why the kids kept leaving their water bottles everywhere.

I said it was a discipline problem.

She said it was a design problem.

The bottles were too heavy when full. Too awkward to carry. The lids leaked in their backpacks.

So they just... stopped using them.

I had been so focused on the behavior, I missed the product failure.

We do this in our industry. 

Blame "disloyal" customers instead of asking if our packaging is annoying to open or if our product fits in their pantry.

My wife doesn't work in CPG.

She doesn't know (or care) what a P&L is.

But she sees a ton of things I don't.

The tiny annoyances. The small frustrations. The gap between what we promise and what actually works in real life.

Here’s hoping you all have a "Lindsay" involved in the product development process.

Everyone you know doubts themselves.

No matter how successful or confident they appear.

I know ultra successful people who wonder if they can take the next step.

They worry that they might lose it all.

They worry they won't be able to make it back if they do lose it.

Despite their sucess, they have a lot of self doubt.

It’s normal when you're starting out and when you get more successful.

So if you're feeling the weight of your doubt.

Just know that it's normal.

You're not doing something wrong.

Everyone doubts themselves.

Congrats to all who made the Forbes list. 

I did not. Therefore, my headline remains in tact.

You can't be great at everything.

And that's actually the point.

The bell curve is undefeated. Small percentage who are elite. Small percentage who are terrible. Large percentage in the middle.

It applies to everything - career, relationships, fitness, hobbies.

Where it gets interesting is when you stack bell curves on top of one another.

Elite in one area almost always means average or terrible in others.

The math doesn't lie.

Which means you have to pick.

Which areas of life you want to be on the upper end of the curve?

And how far down that curve do you want to go?

All those choices have trade offs. 

Personally, I want to be in the 90th percentile in family, career, and health. 

That's above average, but not elite. 

Being in the 90th percentile in all of them means I can't be in the 98th percentile in any. 

It also means I can't even be in the 60th percentile in other things that aren't on my list. 

Some people choose differently. They go all-in on one thing. Become truly elite.

They accept being below average everywhere else.

Neither approach is wrong.

What's wrong is pretending you can be elite at everything.

The trade-off is real whether you acknowledge it or not.

So pick your bell curves.

And stop lying to yourself about the ones you didn't pick.


~~~~~~~~~~~~~

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The DTC era taught founders a dangerous lesson.

You could skip the hard work of understanding your category.

Build a brand, tell a story, sell direct.

No need to obsess over shelf placement, competitive sets, or how retailers think about your space.

But shoppers still compare you to everything else in the category.

They always have.

Whether your product sits next to competitors on a shelf or shows up alone on your website doesn't matter.

A lot of digitally native brands tried to move into retail and got crushed. 

Because they never did the foundational work.

They didn't know their category cold.

Didn't understand how it's priced, how it's merchandised, how it's managed, how decisions get made.

That knowledge used to be non-negotiable.

Before DTC, founders had no choice but to become category experts first.

It was the only path to market.

Now it's optional.

And that optionality is killing brands.

You can't win in CPG without being obsessed with your category.

Not just your product.

The entire space you're competing in.

That's table stakes.

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