Culture shift, Performance Improvement, Leadership Coaching, Management Development, Business Performance through people. 

With a huge emphasis on outcomes and culture, I am completely obsessed with human beings and human performance. A wise man once said: “Organisations don’t change unless teams do. Teams don’t change unless people do.” And this is my passion!

Steve Bent 🔓🟣

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- Closed $30M institutional funding round + other unpublished transactions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

Your startup feels like your entire world right now.

It's not.

The average startup lasts 7-10 years.

Then it's acquired. Or it shuts down. Or you move on.

Either way, 10 years from now, this all-consuming thing will probably be history.

But your marriage? That's supposed to last 50+ years.

Your kids? They'll remember whether you were present.

Your health? You'll live with the consequences of how you treat your body today.

When I was CFO at FreshBooks, I had regular "freshmares" (FreshBooks nightmares). I would  be solving business problems in my sleep. Not very refreshing.

I've watched too many founders sacrifice everything for a company that became a footnote in their biography.

The tragic part? The sacrifice didn't even make the company more valuable.

Exhausted founders make worse decisions. They miss opportunities that fresh eyes would catch. They build cultures that burn people out.

Here's what I tell the CEOs I coach:

Your startup is a chapter. An important chapter. But still just a chapter.

Your life is the book.

Don't write a book where the best chapter destroys all the others.

Set boundaries. Protect your relationships. Take care of your body.

Not despite building a valuable company.

As the path to building one.

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

We had the first Limitless Unconference in Tulum 2 weeks ago.

I showed up with high hopes but no expectations. After all, this was a first time event. Events are hard to run. A lot could go wrong.

I was blown away.

I had 2 success criteria for this event:

1.) The CEOs left committing to put themselves first. A commitment to put physical, mental and spiritual health first. 

Why? Because this gives you more energy and mental clarity to unlock revenue growth. When you do that everything becomes easier.

2.) I wanted each CEO to leave with one unlock for their business.

This was the first time that I allowed "business" Mark and "spiritual" Mark to merge. I don't hide my spirituality, but I also don't waive it in front of people.

Big thanks to Philippe LeBlanc and Mark Homza for calling me out and encouraging me to not hold back.

Also massive thanks to my partner for the event Adrian Salamunovic & his partner Andrea. It was Adrian who pushed me to do this. Andrea and her team take care of all the little details so that Adrian and I could focus on the CEOs.

We will definitely be doing this again. If you want to know how to put yourself first AND build a bigger company, make sure you're on my mailing list. 

Past attendees get first dibs on future events. After that, it's the mailing list. Spots are limited to keep it intimate and real.

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

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.

Your voice is the loudest in the company.

Whatever you talk about becomes an instant priority for your team.

This is powerful. And dangerous.

Here's the problem:

You live in the future. Your team lives in the present.

You're thinking about next year's product roadmap. They're trying to hit this quarter's targets.

You muse about future possibilities. They start dreaming instead of executing.

The risk? They miss current goals. Your future becomes less inevitable.

CEOs work ON the business. Assembling the team. Setting direction. Providing resources.

Teams work IN the business.Building. Selling. Executing.

When your team is distracted by tomorrow, today's execution suffers. Speed drops. And speed matters, especially when VC-backed competitors are chasing the same vision.

So what do you do?

Put future context in a box.

Share the long-term vision. Give them strategic context. Then bring them back to today.

Be explicit: "Here's where we're heading. Now, here's what we need to execute this quarter to get there."

Be selective about what you share.

Transparency builds trust. But constant future talk kills focus.

Your megaphone is always on. Use it to reinforce current execution, not just future dreams.

What you focus on, they focus on. Choose carefully.

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

"Everyone wins when I put myself first."

This was an insight from one of the CEOs who attended our recent  Limitless retreat in Tulum.

The breakthrough: putting yourself first isn't the opposite of leadership. It's the foundation of it.

Your capacity = your company's ceiling. Protect it ruthlessly. Your company is only as strong as you, the CEO.

Martyrdom doesn't scale. Your health is your strategy. Period.

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

In over 80 episodes of The Startup CEO Show, these are the top 10 best practices for CEOs that my guests recommended.

As you get ready for 2026, rank yourself against this list.

Which aspects are you nailing?

Which ones do you need to start?

Build a roadmap for yourself leveraging the hard-won insights of 80 proven CEOs.

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

This is my last week posting in 2025. My theme this week is energy.

It takes massive energy to take an idea and turn it into a market-leading company.  Energy deployed over years (and, if you're lucky, decades).

Most founders & leaders waste energy. As a result, most startups fail.

As Naval Ravikant says: "startups die when founders run out of energy".

As you will see when I am back in 2026, the focus of my Limitless.ceo program is energy. The two step thesis is simple:

Step 1:

✅ Prioritize physical, mental and spiritual fitness. This will give you more energy, mental clarity and inspiration.

Step 2:

✅ Direct that increased energy, focus and inspiration to unlock revenue growth. 

This creates a virtuous cycle of energy, progress and momentum.

To get us started on energy, it's helpful to establish a baseline. Where is your energy today?

In tomorrow's newsletter I will be sharing a CEO Energy Assessment.

Sign up to get tomorrow's newsletter and see where you energy is (see link in bio).

And be sure to tune in here all week for energy tips and stories.

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

At our recent Limitless Unconference one CEO made this commitment: To treat himself like his best client.

For most us, we would never treat our best client the way you treat ourselves

Think about it:

Your best client emails you at 11pm? You wait until morning to respond.

Your best client looks exhausted? You suggest they take a break.

Your best client skips meals and runs on coffee? You'd be concerned.

Your best client never exercises? You'd worry about their health.

But you? 

You answer emails at midnight.

You work through lunch.

You skip the gym because you're "too busy." 

You run on adrenaline and caffeine.

Here's the thing:

You ARE your company's most important asset.

If your best client collapsed from burnout, you'd lose revenue.

If YOU collapse from burnout, the whole thing stops.

So start treating yourself like your best client:

Block time on your calendar that's non-negotiable.

Protect your sleep like you protect client meetings.

Take breaks without guilt.

Say no to things that don't serve you.

Your company doesn't need a martyr.

It needs a CEO who's sharp, energized, and sustainable.

Treat yourself accordingly.

taplio

The Battle

Steve Bent 🔓🟣

Mark MacLeod

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Mark MacLeod

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