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

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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

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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

Ex-VC of early stage startups. Then founded FounderProject, a venture fund run by students investing in student startups. 

The problem? The fund didn’t materialize as I’d hoped, and that hit hard. 

Yet, amidst the disappointment there was real impact. Hundreds of startups took flight, thousands of startup jobs were created, and the VC world took notice.

It became clear to me: while the right funding matters, the right talent can make or break a startup. That insight led me to create StackedSP, a talent firm for venture backed startups.

Fast forward a decade, StackedSP has helped founders and their startups hire thousands - from founding employees, to leaders. Today, those startups are industry leaders and have raised billions from top investors.

But it's not just about the hires. I actively invest in tech startups, and am a limited partner in venture funds. And, building community is crucial. 

Enter Unstacked Startups – a hub for startup founders and talent. There's a podcast, live events, and a newsletter called FounderMail.

My mission? Empower founders, and startups to build a better future.

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Mark MacLeod

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