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- Closed $30M institutional funding round + other unpublished transactions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

Level Agency

Chief Executive Officer

Managing Partner & President

President

Senior Vice President of Operations

Developed product and market strategies that positioned the company to achieve long term growth, while meeting annual revenue and profitability goals. Continually identified and assessed new markets, product and technology opportunities and ensured resources were in place to drive marketing strategy and capitalize on opportunities. 

• Served as a key and active member of the senior management operating team
• Provided leadership for the development of global strategic marketing plans including objectives and strategy for targeted markets
• Drove efforts with product and business development to define an overall product and technology portfolio strategy to drive the long term growth of the organization
• Ensured the development of all strategic product roadmaps and corresponding marketing plans
• Continuously evaluated trends and adjusted strategy to capitalize on shifts in the marketplace. 
• Analyzed existing product and markets in terms of the ability to compete, gain market share, grow revenue and sustain or grow profitability
• Monitored business metrics in regard to revenues, profitability, market share and product portfolio mix. 
• Established metrics for the measurement of marketing program effectiveness
• Developed and manage the marketing budget
• Responsible (in collaboration with sales) for the development of the company’s revenue forecast
• Responsible for the overall management of the marketing team providing coaching, leadership and assistance with resources and strategy development

Vice President of Technology and Product

Member

Vistage Worldwide, Inc.

CallerReady LLC

Responsible for developing and implementing a product roadmap for the company that ensures development and testing of high quality, high value products/services that can be successfully marketed to consumers. Also responsible for leading the development of strategies to migrate customer service and sales onto a completely self service platform. 

• Drive the implementation of a Product roadmap within the company.
• Manage the existing stable of products and lead the ongoing development of enhancements to support increased value to customers.
• Gather and analyze feedback from sales, marketing, operations and partners/prospects to set the strategic vision for existing products and development of new products.
• Manage the execution of consumer research to further support rationale for product development and positioning within the marketplace.
• Direct our internal process to define the product strategy, roadmap and priorities.
• Research, develop & implement a best processes strategy for new product development, launch and analysis.
• Develop requirements documents and use cases for new product features.
• Monitor the status of development projects supporting new features
• Become an expert on other products in the marketplace
• Product life cycle & profitability management.
• Provide guidance and direction to the team on developing new products and managing the lifecycle of existing products
• Build a team to support rapid growth expectations.
• Develop & implement strategy to drive product and customer service onto the web.

Director of Interactive and Product Development

EDMC

As a member of EDMC Online Higher Education marketing department, the Search Manager is responsible for leading and executing search engine strategy for all OHE brands. This position entails development & management of search marketing plans, keyword campaigns, SEO, search inclusion and interactive advertising programs; negotiating contracts, monitoring results and making necessary adjustments in order to generate high-quality, cost-effective student inquiries. 

•	Direct and coordinate multiple “cross-platform” projects while working within established deadlines. 
•	Develop and implement strategy for Internet advertising campaigns designed to increase web site visitors, generate quality student inquiries, and strengthen all EDMC online brands. 
•	Manage and administer EDMC brands’ online budgets.
•	Ensure accuracy (BPC compliance) and quality of all electronic advertising and marketing creative.
•	Develops a collaborative relationship with EDMC to assure online marketing initiatives are in sync with EDMC philosophies and procedures.
•	 Adhere to budget constraints and adjustments while continuing to increase inquiries and web site traffic through the respective EDMC brands’ online marketing campaigns. 
•	Remain current with and possess a thorough understanding of available online advertising, SEO and marketing vehicles as well as measurement tools. 
•	Analyzes current procedures and processes to assure optimal utilization of web-based and email marketing initiatives. 
•	Monitor/track results of online marketing vehicles purchased.

HIGHLIGHTS
•	Launched 3000+ page online education directory portal site from concept to completion in 3 months (2010)
•	Directly managed $20+ million marketing budget to drive year over year growth and drive direct response initiatives (2008-2010)

Search Marketing & Display Advertising Manager

• Analyze Web traffic using Omniture, Google Analytics, and other data collecting sources to support the analytic needs of the business
• Lead driving core insights from the data to suggest, create and execute multivariate or a/b/c tests that drive fundamental improvements to the site experience
• Develop and implement data strategy across multiple “listening posts” (websites, surveys, testing, CRM systems, market research etc) to provide a comprehensive view of students, faculty, and prospects across the online web experience 
• Work  with the Web Strategies team to identify gaps in the data capture strategy and implement enhancements  Improve and document processes for gathering metrics and data analysis

HIGHLIGHTS
•	Implemented multiple analytics software packages throughout web experience to facilitate creation of executive dashboards and reports (2007-2009)

Web Strategies Analyst

• Ownership for operational results of recruitment websites.  Personally manage and drive daily performance of metrics against internal requirements as well as competitive positioning
• Web strategy development including ensuring the brand experience by combining the convenience of on-line education with the experience of a top traditional school and making it come to life through our recruitment websites to support a consistent web-based end to end student experience.   Creates web environments to support the student recruitment goals and provide automation that supports growth and scale to the organization. 
• Provide leadership on web solutions development for the OHE organization.  Develop and manage scope, resources and project plans to deliver appropriate web solutions.
• Partner with OHE Marketing organization to implement marketing strategies.

HIGHLIGHTS
•	Introduced Landing Page Optimization and MVT testing to company leading to 100-300%+ increases in conversion across three different brands (2007-2010)
•	Successfully oversaw implementation of new student recruitment initiatives including: marketing site redesigns, microsite launches, online student tours, and admissions tools (2008-2010)

Web Producer, Student Recruitment

Recruit new students to meet new student plan. Develop and maintain positive relationships with students. Provide creative solutions to complicated admissions problems. Contribute to a positive results driven professional work environment. Serve as a job knowledge expert, trainer, and mentor for new hire and veteran ADAs.

Director Of Admissions

The Dinner Pantry, Inc

Developing and executing the go-to-market strategy for a food service startup. Creating and fully developing company network infrastructure and e-commerce website. Responsible for the content and publication of said website by coordinating, designing, and monitoring electronic publications for distribution. Developing and implementing strategies to improve group marketing.

Head of Marketing & Product

In his tenure as president & CEO of Level Agency, Patrick Patterson oversaw its transformation from a pioneering, fast-growing higher education shop into the performance-marketing powerhouse it is today. Under his leadership, the agency’s revenue grew 30% or more annually; its profit margin increased 4X; its marketing spend now tops $50M annually, and its capabilities have broadened to offer more complementary services for more industries.

Great marketing starts with asking great questions. From the outset of his career, Patterson applied his background in computer science and math to the challenge of reaching and engaging audiences (and carefully measuring every result). In an industry increasingly driven by automation and machine learning, he excelled, ultimately managing a $30+ million budget for Education Management Corporation. Patrick then took his passion for creating value to product development, implementing lean methodology at a technology startup that focused on using data to drive efficient sales enablement.

His drive for efficiency, performance, and continuous improvement led him to join agency founder Thomas Donohoe in 2012 to oversee Level’s operations and strategic direction - eventually purchasing the company in 2021 with his partner, Patrick Van Gorder.

Patterson’s vision for Level Agency is to be the go-to performance marketing agency when clients want real, measurable results. Reaching this goal requires an uncompromising commitment to performance: platform excellence, compelling creative, client partnership, growth mindset, and constant innovation. By surrounding himself with talented, adaptable colleagues, he knows he’s set the agency up for success.

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