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- Closed $30M institutional funding round + other unpublished transactions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

Greg Moran

Evergreen Mountain Equity Partners

Evergreen Mountain Equity Partners is an early stage (seed and series A) venture firm focused exclusively on future of work and HR related technologies. Our mission is to be an active partner to great founders trying to find a way to achieve their vision.

Serve as board member or board observer to Truvelop, Ceipal, Conquer, Chatterworks, Hitch and Spacebands.

Managing Partner & Founder Coach

Conquer

At Conquer we are making selling smarter through our enterprise sales enablement platform. Our comprehensive solution combines automation, advanced analytics and AI-driven insights to empower sales teams and drive revenue growth. 

By leveraging our platform, sales professionals can optimize their strategies, enhance customer engagement, and close deals more efficiently.

Chief Executive Officer (Interim)

Conquer provides sales enablement software to large sales teams.

Board Member

Interim Chief Revenue Officer

Outsorcy

Outsorcy connects businesses with top-tier global talent to drive efficiency and growth. Specializing in outsourcing solutions, we help companies build dedicated teams, find world-class professionals, and streamline operations across marketing, technology, and business support. With a focus on flexibility, cost-effectiveness, and quality, Outsorcy empowers organizations to access diverse, skilled professionals worldwide, enabling them to scale efficiently and achieve their goals.

Camden Partners

Serve as an Operating Partner to Camden Partners. Since our founding in 1995, Camden Partners has focused on investing growth equity in lower middle market companies. We actively partner with strong management teams leveraging our domain expertise, operating experience and extended network of resources to help growth companies reach their full potential.

Operating Partner

Outmatch (now Harver)

Harver (formerly OutMatch) is a leading HR technology company that is transforming the way organizations hire and assess talent. 

Our innovative platform combines advanced data science, AI-powered assessments, and interactive pre-employment tools to help companies make smarter, data-driven hiring decisions. 

With Harver, companies can streamline their recruitment process, identify top candidates efficiently, and reduce bias in the hiring process. Our mission is to revolutionize talent acquisition by providing organizations with the tools they need to build high-performing teams and drive business success.

OutMatch makes people decisions more scalable, predictable, and personal with an end-to-end talent decision platform. The world’s most recognized brands rely on OutMatch to scale recruitment, understand their talent, and personalize candidate and employee experiences. Over 1,000 global companies trust OutMatch technology to process millions of candidates annually, and to achieve 25X return on investment through better people outcomes.

OutMatch is a portfolio company of Rubicon Technology Partners (headquartered in Boulder, Colorado) and Camden Partners (headquartered in Baltimore, Maryland).

President and CEO

Chequed.com

Oversight of all aspects of this emerging growth technology company. Provided vision and direction to the initial and ongoing product development. Raised outside equity based capital. Negotiated strategic partnership with major academic institution for R&amp;D. Initiated, negotiated and completed the acquisition of leading industry player to incorporate into Chequed. Ongoing responsibility for capital raising, recruitment of management and board level hires, acquisition integration as well as general management responsibilities.

Founder / President & CEO

Talent Management Group / W Business Books

Author of two books on recruitment strategy for the field hiring manager:

1.) Hire, Fire & The Walking Dead, W Business Books, May 2006 (http://www.amazon.com/Hire-Fire-Walking-Dead-Recruiting/dp/0832950017/ref=sr_1_1/105-7883773-0736465?ie=UTF8&s=books&qid=1181612256&sr=8-1)

2.) Building the TalentEdge: A Manager's Guide to Recruiting the Best, AuthorHouse, October 2005

Consultant, Author and Speaker

Talent Technology Corporation

Created a channel sales/partnership program and oversaw the initial phases of execution for this provider of human resource component technology. Responsibilities included partner identification, outreach, screening, contract negotiation and initial marketing of new partner relationships. Served as front line for acquisition identification culminating in successful completion of PeopleFilter Technologies in April 2008. In addition, oversaw the Industry Sales group focused on sales of the Resume Mirror product line to the top 500 staffing firms worldwide.

Director, Industry Sales and Partnerships

Better People, LLC

Better People provides technology-driven recruitment process outsourcing to emerging growth and established companies throughout North America.

Chairman

PeopleAnswers America, LLC

Acquired the rights to build the sales distribution channel for this web based behavioral assessment one-demand software company. Created and executed upon direct, partner and dealership strategy throughout North America resulting in multi-million dollar sales growth within 3 year period.  Provided direct enterprise sales (quota carrying) as well as sales executive support. Utilized full-time dealership and direct strategies as well as a traditional reseller relationship as primary methods of growth. Responsible for the creation of all channel start-up and ongoing training and development programs as well as internal communication and marketing initiatives. Created recruitment, evaluation and performance appraisal process used for management and development. Successfully sold distribution channel back to PeopleAnswers, Inc. of Dallas, Texas.

Vice President of Sales/Founder

Multi-Exit Founder & CEO, Advisor, Investor, Board Member | Posting daily insights to help you scale to $100m+. Host - The Founder’s Journey Podcast

Founders often face isolation, burnout, and the “now what?” stage after their first taste of success. I’ve been there—and I’m here to help you scale smarter and faster.

Over the past 20+ years, I’ve launched and exited multiple companies with valuations exceeding $100M, completed a dozen global acquisitions, raised nearly $500M in capital, and advised dozens of high-growth founders to do the same.

Now, I’m focused on “Scaling Together” through The Founder’s Collective—a curated membership community for ambitious entrepreneurs seeking strategic coaching, actionable resources, and meaningful peer connections. Through monthly coaching sessions, playbooks, live Q&As, and in-person events, members gain a powerful ecosystem to overcome isolation, lead effectively, and accelerate growth. If this resonates, apply today:
https://www.thefounderscollective.com/apply-to-join

I also take on a limited number of personalized coaching clients who want to supercharge their trajectory. If that’s you, DM me.

Beyond business, investing, and coaching, I’m a dedicated traveler, an avid home cook (inspired by Julia Child!), and a lover of the outdoors—especially fly fishing, hiking, and skiing in Colorado and Montana. Most importantly, I’m a proud husband and father of two amazing kids, each on their own unique journey.

At Conquer we are making selling smarter through our enterprise sales enablement platform. Our comprehensive solution combines automation, advanced analytics and AI-driven insights to empower sales teams and drive revenue growth. 

By leveraging our platform, sales professionals can optimize their strategies, enhance customer engagement, and close deals more efficiently. 

Today’s the day. And it all starts here.
Launch day for Scaling Across Borders: Season 1 – Kosovo.

This has been one of the most meaningful projects of my life.

When we started, I had no idea what to expect. I just hoped we could tell a different story about Kosovo… that it’s not a war-torn country, but a young, energetic nation full of talent, ambition, and grit.

It did more than that.
It touched a nerve. It showed a side of this place that the world rarely sees. The response here has been overwhelming.

Kosovo is an underdog story, and it’s been the honor of a lifetime to help tell it.
This country deserves to be seen, taken seriously, and invested in.

Somewhere along the way, I realized Scaling Across Borders wasn’t just a storytelling experiment for me or Outsorcy. It became a mission.
Because Kosovo isn’t the only misunderstood place.

There are founders everywhere, building world-class companies in overlooked corners of the world, whose stories never get told. They’re not chasing hype or creating videos to announce their latest raise. They’re building the future of their nations.

That mission continues beyond Kosovo.
It’s about authentic stories of grit and resilience, where travel meets entrepreneurship.

But it all starts here, tonight, in Pristina.

To the incredible team at Outsorcy  and my partners (Jim Trimarco Demian Costa Blendrit Elezaj Rilind Elezaj Ira Grossman  Siddharth Sehgal ), to Wanto Studios, my family (Allison, Olivia and Jackson) . and, of course, to the great people of Kosovo who trusted me to tell a small part of your big story ... thank you.

This experience changed me.
And it’s only the beginning.

🎥 Join us live from Pristina tonight at 6 PM CET / Noon EST / 9 AM PST on YouTube for the global premiere.

👉 Subscribe today to follow the journey. Link in comments.

Kosovo! Let’s go!!!!!

No alternative text description for this image

Scaling Across Borders - Kosovo episode now live! Link in comments.

This chapter is all about the people who left Kosovo, built their careers around the world… and chose to come back.

And the ones who arrived by accident ... and stayed on purpose.
Founders. Educators. Builders.

A generation turning Kosovo into a global hub for talent, tech, and opportunity. 🇽🇰

Featuring:
• Blendrit Elezaj — connecting Kosovo’s talent to the world
• Gent Dedushi — from Google + NYC to building at home
• Albina Balidemaj, PhD — shaping future leaders at RIT Kosovo
• Alejtin Berisha — bringing world-class education systems to Kosovo
• Zach Dowd, Ethan Allan & Dion Berisha — building Techatlon inside ICK

🎬 Episode 2: The Ones Who Came Home

📍 Now streaming! Link in comments.

Watch the full episode, drop a comment, and tell us what part of their story hit you the hardest.

New episodes every week. Don’t forget to subscribe.

Scaling  Across Border Episode 3 is Live! 

This one is about the people building Kosovo’s new economy from the ground up… not with factories or resources, but with pure intent and zero permission-seeking.

You’ll meet:

Gentrit Gojani and the KODE Labs 
Mergim Cahani 
Dorina Grezda and Shpend Lila at Innovation Centre Kosovo (ICK) 

Watch Scaling Across Borders — Episode 3!
Link in comments.

We're live in Kosovo! Join our livestream for the Scaling Across Borders premiere! 🇽🇰 

https://lnkd.in/enyiKVHf

Open video: Scaling Across Borders Premiere! on youtube.com

I’ve had days where it felt like nothing was moving.
No big wins. 
No breakthroughs.

But here’s the truth founders hate admitting:
The days that look quiet are often the ones that compound the most.

What kept me moving wasn’t some dramatic reinvention.
It was the small, almost boring actions done consistently.

So today, don’t go hunting for the perfect plan.
Pick one small move and execute it.

Momentum isn’t magic, but it’s built.

Subscribe to my newsletter for weekly insights: https://lnkd.in/e8wJrt5A

taplio

The Battle

Mark MacLeod

Greg Moran

Followers

Posts

Engagements

Likes

Performance ScoreMark MacLeod's LinkedIn Performance

Performance ScoreGreg Moran's LinkedIn Performance

Ready to grow your LinkedIn presence?

taplio

The Battle

Mark MacLeod

Greg Moran

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 ScoreGreg Moran's LinkedIn Performance

Ready to grow your LinkedIn presence?

Performance ScoreMark MacLeod's LinkedIn Performance