Sean Kelly

Founder & Investor. Building companies at the intersection of health, media & founder performance.

Hey there, I’m Sean. I play at the intersection of investing, media and human performance.

I’m a three-time INC 500 founder & entrepreneur with businesses in eCommerce, SaaS, media and B2B services that have collectively generated hundreds of millions of dollars in revenue.

Right now, I serve as a General Partner at The Family Fund and am the CEO of Significant Publications, a B2B digital media holding company.

I'm particularly passionate about our brand FounderIV in support of today's founder-athletes. We help today's top entrepreneurs achieve breakout performance in their personal and professional lives.

I co-founded and led multiple other companies, including SnackNation, a health-centric foodservice and brand discovery platform that served 20,000 businesses across the US. 

Under my leadership, SnackNation was honored as one of the country’s Best Workplaces by Inc. Magazine, recognized for Top Company Culture by Entrepreneur Magazine, and certified as a Great Workplace by Great Place to Work®.

Forbes listed me as one of the top 30 leaders under 30 and one of America’s most promising CEOs under 35. Comparably also ranked me among the country’s top 50 small-to-medium sized business CEOs multiple years in a row. 

Outside of the business world, I’m a two-time national medalist in freestyle snowboarding, hold an advisory role at the growth capital firm, Meaningful Partners, have a degree in Biomedical Engineering from Columbia University and am an avid sports fan of all Michigan sports teams (especially the Wolverines).

I currently live in Venice, CA with my wife and college sweetheart, Shannon, and our goldendoodle, Jameson.

Chairman

We built the first Founderland in 10 weeks.

And almost died.

This past year we gave ourselves 6 months and built an external team to do it and it still wasn’t enough time.

So for next year’s event we decided to make the build a year-round affair…

And are focused on making Founderland a brand that lives throughout the year, not just as once-every-October event.

It’s funny to see how random ideas become full-time jobs lol

Took a quick trip to NYC this week to discuss Founderland ‘26 with one of our top partners J.P. Morgan  

The verdict?

It’s going to be big. 

Perhaps not as big as JPM’s new $3B global HQ at 270 Park Ave (most spectacular office I’ve been in w/ a Warhol or Jasper Johns around every corner)…

But still pretty big and lots of fun with a yuge amount of deals commenced (misspelling intentional)

Thanks for the tour Michael Conte you’re a legend and friend.

And glad to see you’re carrying Ancient Crunch Inc. MASA chips in all of your shops!

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Current health travel stack:

Zoomed off to NYC, Philly and Austin this week.

Back to back meetings all day, late dinners and sports games at night, and planes trains and automobiles like we all know.

Seems like 1/2 of the people I’ve met have a cold.

Here’s what I take on the road to feel good while away…

and do my best to arrive home feeling not-dead to the fam. Works most of the time ;)

 - Sinus rinse bottle filled with filtered water, betadine and salt/baking soda (use after every flight, likely illness prevention tactic #1)

- Zinc acetate lozenges if I’m feeling worn down or fatigued

- KetoneIQ every morning when I wake up to get that cognitive boost

- Momentous whey protein, plant protein, and creatine (10g) + Supergut fiber blended 1-2x per day to supplement diet

- Momentous Sleep pack + medical mouth tape + sleep mask every night

- Metal shaker bottle that doesn’t get gross

- Some type of hydration packets 2x/day minimum (right now using Dry Water)

- WIP 100mg energy pouches for a little boost early in the day usually before workout

- Another ~20 or so supplements in my vitamin case that I pre-fill for each day prior to the week

Sure, sleep/nutrition/exercise are essential and the most  important…but it’s near impossible to not sacrifice them a bit while playing the part of road warrior…so at least for me, travel supplementation is key.

Momentous Ketone-IQ DryWater Supergut

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

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.

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.

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.

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.

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

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.
✨

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.

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The Battle

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