Seth Yakatan

Raising & Selling 📈 $1B+ Raised 💰 22 Companies Sold 🤝

Are you struggling to communicate your vision to the capital gatekeepers?

Are you exploring selling your business but don’t know anything about:
✘ Due diligence
✘ Term sheets
✘ Earnouts

Friend, you're lucky you found me...

I'm Seth Yakatan.

I have 30-odd years experience as a corporate finance professional.

My specialties are:
💰 Raising money
🤝 Selling companies

And I’m f**king good at it.

I’ve raised over $1B and sold 22 businesses.

My career has mostly been supporting small-cap and major corporations seeking capital to grow, or
to find strategic acquirers.

Most of these companies are in: 
— biotech
— cannabis
— pharmaceuticals
— DTC consumer goods

I’ve been on boards, taken companies public, gone up against multinational corporations, raised from VC and PE funds.

All of it. 
Many times over.
Whatever your problem is, I’ve seen it before.

But let me level with you:

What I REALLY love is helping people to get to the finish line.

Talking to entrepreneurs excites me.

But in my experience, entrepreneurs are mostly s**t at raising capital and selling companies.

** They just don’t understand investors **

And that’s where I come in.

Together, we workshop: 
✔ Your pitch
✔ Your deck
✔ Your strategy 

And help you raise the capital to GROW and SELL your business.

If you need this help—and almost every business does—send me a DM.

Like, now.

Don't lose another potential investor or acquirer with the wrong pitch.

Seth ✌️

Co-Founder

Merchant Bank / Advisory / Family Office

While politicians are arguing about hemp, Kratom is being sold as a “natural wellness supplement.”

But let’s STOP pretending.

This is NOT chamomile tea.

This is NOT “plant-based stress relief.”

This is an unregulated opioid analogue with street-corner quality control.

And it’s ending up in gas stations, smoke shops, and TikTok “self-care” feeds.


>> Whats Happening?

Kratom is being sold everywhere with little to no restrictions.

And, IMO, it is DANGEROUS.

It contains mitragynine and 7-hydroxymitragynine, compounds that we know:

→ Bind to mu-opioid receptors
→ Produce opioid-like euphoria and sedation

And it creates tolerance and withdrawal patterns basically indistinguishable from low-grade opioid dependence.

California’s Department of Public Health just issued a formal advisory (NR25-016) warning that:

Kratom products are ILLEGAL to manufacture and sell in the state.

Claims about pain, anxiety, or withdrawal treatment are unproven.

And that multiple fatal overdoses have already been linked to kratom in Los Angeles County

This is not “maybe dangerous.”…this is DOCUMENTED harm.


>> Why This Matters?

OxyContin addiction didn’t start because people wanted to get high.

It started because people were in pain, desperate & were told something was safe and “less addictive.”

We have seen this movie before and I know exactly how it plays out.

Kratom is unregulated, inconsistently dosed and frequently adulterated.

And marketed using the same language pattern that launched the opioid epidemic:

“Natural”, “Safer than pharmaceuticals”, “Helps with withdrawal”

The result is people self-dosing their way straight into dependency.

Not because they’re reckless.

But because the product is designed to look harmless.

And the supply chain knows exactly what it’s doing....


>> What Am I Watching?

The pattern is repeating: 

Normalization via wellness marketing (“It’s just a plant.”)

Distribution concentrated in deregulated retail (Vape shops, convenience stores, social media DMs.)

Dependence masked as “daily routine" (Users don’t realize they’re sick until they stop.)

Regulators reacting only after deaths accumulate.

If we wait for “more data,” we are doing nothing more than running the Purdue Pharma playbook in slow motion.

This is not a supplement it’s an unregulated opioid with branding.

Kratom should not be sold.
Kratom should not be normalized.
Kratom should not be framed as “self-care.”
Kratom should be STOPPED.

When you want to push the boundary, what do you do?

TRY HARDER.
 
So I am honored to announce my latest collaboration with Fat Nugs Magazine x Seth Yakatan: A New Live Industry Series

>>> WHAT ?
I'm teaming up with Fat Nugs Magazine to launch a brand-new live discussion series spotlighting cannabis products and brands. 
 
And to start we're tackling pre-rolls - a category whose growth cannot be denied.

>>> WHO ?
Andrew Wells
Cesar Angobaldo
Courtney Zalewski
Fernando Bent-Mullings
Mei-Ling Campbell
Timeka Drew
Catherine Sidman
Luna Stower, MAT, CG ✨

>>> WHEN ? 

The series kicks off with its first episode Thursday, November 20th at 11AM EST/ 8AM PST.

FNM Presents: Voices of the Plant w/ Seth Yakatan
Preroll Edition 
Business. Culture. Community.

 
Sign up here: https://lnkd.in/geV4jVmy 

& MARK YOU CALENDARS for Thursday, November 20th at 11AM EST/ 8AM PST.

You want your 15 minutes of fame?

Then find me and my man Lance C. Lambert ✓ in VEGAS....

My friends at Fat Nugs Magazine have made the questionable decision of giving me a camera and a microphone (LOOK OUT!!!)

Fat Nugs Magazine  x PufCreativ event, Light Up Las Vegas, is going to be 🔥 

Me + Lance, badass activations, the food, infused beverages, live art, live music from John Shute's band, Bubala, the Faces of Cannabis, and I GOT A MIC!!!

Fat Nugs Magazine
John Shute, MBA
PufCreativ

Well folks, I have to admit that I was WRONG… I know, SHOCKER 😱

About 3 months ago I put up a post on AYR Wellness.

I said RIP…

But suddenly, AYR has come back from the dead…

Last week AYR Wellness Inc. announced that it was going to initiate CCAA proceedings. 


>> What's Happening?

On November 17, core assets of AYR’s subsidiaries will be transitioned to a newly formed acquisition vehicle (NewCo) owned by certain AYR senior note holders.

Basically this means that the lenders are going to run the company to try to get a recovery.

This is the same thing we’ve seen with several other companies…


>> Why is it Relevant?

1. Note trend
2. See #1

Just another case of investors taking the keys and trying to operate…


>> What Am I Watching?

This is about the fourth version of this flavor, will see if it tastes any different.

This industry has now become an SOP for the ‘equitization of debt and operate’ strategy…

Grabbing popcorn….

Hit the Debt Wall Jokes in the comments please.

Getting pumped for earnings season ???

WELL I AM...

Talking about Q2 a while back with the squad from 

The Dales Report

How do you think that that Q3 is going to look ???

Hit me in the Comments....

and thank you Shadd Dales + Anthony Varrell

BIG SCANDAL in NY this past month…

Omnium Health just found out the hard way that renting your license isn’t the same as running a business.


>> What’s Happening?

NY state says Omnium was renting out warehouse space to unlicensed operators and then moving products through its own distribution channels.

The regulators are moving to yank Omnium Health’s permits and hit them with 7-figure fines, and recall $10M worth of product.


>> Why is This Important?

This is the first major enforcement under the state’s new crackdown.

It signals a shift from “we’re building the market” to “we’re cleaning it up.”

And now the fallout is real:

Multi-million dollar recall.
Permanent ban on participation.
Dozens of brands hurt.


>> What Am I Watching?

I have called out that New York’s cannabis roll out experiment has been chaos from DAY ONE.

Slow licensing, illegal stores on every block, and bureaucrats chasing their tails.

But this move finally shows they’re willing to go after the suits, not just the bodegas.

It’s a warning shot.

Maybe, just maybe New York will clean up its act?

You enjoy your freedom ?

Then thank a VETERAN...

I am honored that members of my family have proudly served to ensure that my butt can. go get a burger fries and a coke...

Lets give it up for a REAL AMERICAN HERO...

Evan Hunt

Evan is a:

— Decorated 20-year veteran and combat aviator
— Community and business leader
— Texas family man
and has NO AGENDA other than his SERVICE !

He's running for U.S. Congress in Texas as a Democrat. 

He's taking on MAGA extremism and wants to recapture the House in 2026.

You can donate to help his cause here: https://lnkd.in/gQana6Wu

Who keeps me bullish?

Wyld & Aaron Morris

In ANY other industry, THAT'S A ROLL-UP PLATFORM.

General Catalyst (CALL ME)

Thanks to the gents From the Weeds to the Clouds - Michael Krefman + Michael Peterson

Do you have a functioning company?

i.e. Are you generating CASH FLOW??

Then consider yourself SUCCESSFUL, because you are in the MINORITY
in c@nnabis.

So what advice do I give you....???

Well with 5 companies over $150M in revenue in receivership...

1. STAY IN IT
2. STAY IN IT
3. STAY IN IT!!!

And thanks to my friend Scott Greiper for moderating a great panel....

The 5 Stages of Grief: Cannabis Edition


Stage 1: Denial

For everyone: The initial shock and disbelief that loss has occurred, acting as a buffer against overwhelming emotions.

For us: The initial shock that prices are NOT going to stay high forever and act as a buffer against the mountain of debt raised.


Stage 2: Anger

For everyone: A natural reaction to loss, where one may feel frustration, resentment, or rage at the situation.

For us: Manifests in yelling at A/R collections, city counsel meetings, boardrooms, or in the comments on LinkedIn.


Stage 3: Bargaining

For everyone: Negotiate with fate or a higher power to undo the loss, often involving phrases like "If only..." or "What if...".

For us: “Well I can just SELL the license, not pay taxes, not pay suppliers, vendors, employees or investors and get my creditors to amend and extend, plus FEDERAL HAS TO come soon, right??”


Stage 4: Depression

For everyone: Feelings of sadness, despair, and hopelessness set in as the reality of the loss becomes clearer.

For us: This market SUCKS, this industry SUCKS, these people SUCK, this government SUCKS. 


Stage 5: Acceptance

For everyone: Reach a point where the loss is acknowledged and understood, and one begins to adapt to the new reality.

For us: Lower prices, market volatility, hope for “catalysts” and a maybe we never get a Federal “save”.

Plus, all this s**t I’m eating is making my stomach stronger!

Did this resonate with anyone??

Hit those comments.

Want to see me in a SUIT???

Well if you are Inside the Beltway today there is a CHANCE...

You'll find me in my clown suit, all dressed up for my crew at IgniteIt Cannabis.

See you today in the District for my photo opp.

Use my link and get in at a discount: https://lnkd.in/e45zHKrW

I Failed As An Odds Maker
And almost got run out of Vegas as a result !!!

What I Thought ??? 
I used to believe I could predict things. 
I thought outcomes were logical: 
Markets mature THEN prices stabilize 
Regulators see tax revenue AND regulation eases 
Consumers migrate to legal markets WHILE illicit fades 
Capital flows to efficiency LETTING good operators win 
None of that happened.

What I Learned ??? 
Regulation became politics: NOT economics 
Taxation became punishment: NOT policy 
Consumers followed availability: NOT governance 
And capital flowed to the loudest or biggest: NOT the best
So, I tried to be an odds maker and failed..

What Did I Learn ??? 
The cannabis and hemp space is not a market it's a game of unlocks: 
Access unlocks: Who can sell where 
Distribution unlocks: Who gets shelf space 
On-Premise unlocks: Who gets to shape consumer behavior 
Regulatory unlocks: Which side of the line you operate on

The people who win are not the ones with the best products
They're the ones with the best positioning when the unlock happens
I wasn’t wrong about the demand…I was wrong about the sequencing

So I failed as an odds maker, and changed my lens 

I stopped predicting when something will change 
I started positioning for what happens when it does 

I don’t need to guess the date Congress wakes up 
I just need to be on the board when they do
You don’t have to be an oddsmaker… 
You just have to be aligned when the unlock hits. 
And that’s a game I like my odds in.

Today I give THANKS...

That I am not a Turkey...although some of you might beg to differ....

Thats it...

Happy Holidays !!!

And make sure you tell someone you love them today....

Here’s the big thing I learned from the hemp ban:

First, NO ONE has been louder than me about the coming “inflection.”

Well…maybe I’m the dumbest guy on the internet…

Let’s break down why:


>> The Good

The Farm Bill allowed for the ubiquitous distribution of these molecules.

Loophole/Grey Area/ Unintended consequence, I don’t care what you think about that.

Putting the MOLECULES on Main Street and in the mail was NOT the intent.

But guess what, the consumer chose….the MOLECULES. 


>> The Bad

Cannabis is demonized, marginalized and constrained.

Produce, manufacture and sell in limited silos in specific areas in selected states.

Want to purchase? Go to the crappiest part of town where they put airports, chop shops and strip clubs.

Banking? Forget it. Normalization? Sure as soon as there is a dispensary on Rodeo Drive.


>> The Ugly

Once the Farm Bill allowed for the democratization of cannabis to occur, the consumer made a clear choice.

THEY CHOSE THE MOLECULES.

In the mail, in grocery stores, in liquor stores, in big box retail.

When you put the MOLECULES in the normal consumer purchase cycle they CHOSE IT.

and then what happened? Retail adopted. 

And that SCARED THE SH$T OUTTA: 
— ALCOHOL
— BEVERAGE
— CPG
— TOBACCO
— PHARMA

End of the day whether its Hemp or THC we are talking about the same MOLECULES.

The public WANTS it. So let’s keep making that case and stay united.

When something that NEEDS to exist but doesn't, what do you do?

YOU CREATE IT.
 
So I am honored to announce my latest collaboration with Fat Nugs Magazine

A new series of LinkedIn Live sessions to educate, spotlight and discuss critical issues around PRODUCTS.

Why? 

Because Instagram is NOT a safe space and LinkedIn seems to have critical mass for OUR INDUSTY.
 
I'm teaming up with Fat Nugs Magazine to launch a brand-new live discussion series spotlighting cannabis products and brands. 

Expect we will amplify voices from every corner, deeply knowledgeable professionals to everyday consumers.

Episodes will stream across multiple platforms, giving an unfiltered look at the products, stories, and people behind them.
 
And to start we're tackling pre-rolls - a category whose growth cannot be denied.

Expect 8 panelists to break down the good, the bad, and the ugly of pre-rolls,

Panelists will also get the chance to sample prerolls LIVE, bringing real-time reactions and insights to the conversation.

This isn’t just another panel, it’s the start of an honest, wide-open dialogue about the products that define our industry.

The series kicks off with its first episode Thursday, November 20th at 11AM EST/ 8AM PST.

FNM Presents: Voices of the Plant w/ Seth Yakatan
Preroll Edition 

Business. Culture. Community.
Welcome to Voices of the Plant - the new Fat Nugs Magazine LinkedIn Live series that brings real conversations from the heart of cannabis.
 
Sign up here: https://bit.ly/3LpTDXd

& MARK YOU CALENDARS for Thursday, November 20th at 11AM EST/ 8AM PST.

You doing anything today??
 
Fat Nugs Magazine x Seth Yakatan present: The Plant Panel

We're hosting a new LinkedIn live with some of the sharpest minds working in cannabis.

Andrew Wells
Cesar Angobaldo
Courtney Zalewski
Fernando Bent-Mullings
Mei-Ling Campbell
Timeka Drew
Catherine Sidman
Luna Stower, MAT, CG ✨

TODAY: November 20th at 11AM EST/ 8AM PST.

FNM Presents: The Plant Panel w/ Seth Yakatan

Episode one is the Preroll Edition 

Business. Culture. Community.

Sign up here: https://lnkd.in/geV4jVmy

Believe it or not, I continue to hear from people that c@nnabis is NOT efficacious.

“Cannabis doesn’t really work for pain, sleep, or anxiety.”

I hear this from people who have:
— Never read a single clinical data table
— Never treated a patient
— Still think weed = teenagers + Bob Marley poster

Meanwhile, the SCIENCE is right there.


>> What’s Happening?

Recent clinical evaluations show consistent, measurable benefits:

Pain: 
→ Patients report statistically significant reductions about 0.5cm on a 10cm scale across populations. 
→ No placebo, that’s real analgesic effect at scale.

Sleep: 
→ Cannabis improves subjective sleep quality. 
→ If you’ve ever actually not slept, you know that you feel in the morning matters more than what your polysomnography printout says.

Anxiety: 
→ At appropriate dose and context, cannabinoids produce reliable anxiolytic effects, especially CBD.
→ THC requires respect and calibration yes. But to pretend it “doesn’t work” is just LAZY.

These effects are real, repeatable, clinically observed, and patient-reported across thousands of data points.

This is evidence!!!


>> Why Does This Matter?

There is a massive cultural blind spot around what counts as “meaningful efficacy.”

We are conditioned to think only in miracle outcomes:

— Erase all pain
— Cure insomnia
— Eliminate all anxiety

That’s not how real medicine works.

Real medicine is incremental improvement that accumulates into quality of life.

And cannabis delivers exactly that.


>> What Am I Watching?

The brands, operators, clinicians, and researchers who will win the next decade are the ones who:

1. Respect the evidence
2. Respect individual response and dosing
3. Position cannabis as a meaningful tool in the therapeutic toolkit
4. Communicate in clinical, human terms

Because here’s the TRUTH:

Cannabis works. It’s medicine. PERIOD.

So when someone dismisses cannabis because it’s not a miracle cure…

They’re telling you they don’t understand patients, medicine, or reality.

(and if you don’t know who is with me in the picture DO YOUR HOMEWORK)

I’m in a New York State of Mind right now.

I’ve been spending some time in the Empire State recently.

I’ve put together a few observations and suggestions…

Take them with a grain of salt.


>> Lessons From The Future

New York is currently a $1.7B market and will certainly grow.

But price compression has not yet begun to occur…

Jarred 1/8ths are amongst the highest price per gram of any legal state.

Most pure retail operators are not businesses but borderline not-for-profits.


>> Where the Pitfalls Are

Regulators in New York have already showed their hand, so HOPEFULLY they won’t continue the clown games.

A/R issues are coming, bank on it.

More brands are coming, and so is more high quality flower.

Retailers are going to feel the pinch of high rent, overbuilt stores and lack of profitability.


>> Who Can Win?

1. Those willing to study and learn from the past to avoid the inevitable future

2. Brands and those who are both entrenched and currently profitable

3. Anyone with one of the 10 RO licenses

4. Those currently there and in the lead


>> Who Can Lose? 

1. Consumers and investors

2. Anyone who is currently unprofitable - because it AIN’T gonna get easier.

3. Anyone without one of the 10 RO licenses.

4. Those eyeing the market from other states thinking it’s a gold mine...

Agree? Disagree?

Hit those comments.

So Ohio just issued a BAN on THC drinks, gummies, other hemp products…

Is this just another domino to fall in the ever changing Hemp landscape?

I’ve seen this movie before, pretty sure I now how it is going to end…

Alcohol lobby keeps making it RAIN!!


>> What’s Happening?

Ohio Gov. DeWine just dropped a 90-day ban on intoxicating hemp products — drinks, gummies, the whole lot.

The justification? Predictably it was to “protect the children…”

The reality is this is just another political move after months of legislative inaction.


>> Why It Matters?

Let’s be clear: This isn’t about safety. It’s about control.

Hemp beverages have been sitting on shelves for years — in gas stations, grocery stores, and yes, maybe even in a few PTA moms’ purses. 

But now they’re suddenly dangerous candy? Please.

What’s really happening is that regulators are scrambling because hemp is moving faster than their tax codes and licensing frameworks.

Meanwhile, the consumer is left wondering why they can buy 1.5L of vodka at Target but not a 5mg seltzer.


>> What Am I Watching?

I’m watching who profits from the pause. Follow the money and, more importantly, the LOBBYING.

Does this becomes a blueprint: ban first, regulate later? (n=2 Ohio and California?)

How do brands now pivot? On-premise and licensed retail just became the only legal outlets for 90 days.

I hate watching growth and innovation get punished for outpacing bureaucracy.

And Ohio just told every hemp company: “Thanks for the R&D, we’ll take it from here.”

So your cannabis company “got international distribution?”

Well….let’s look a little more closely here shall we:


THE REASON PEOPLE ARE RUNNING OVERSEAS

Domestic cannabis margins are garbage right now.

Wholesale prices down 40–70% in key markets in 24 months.

Effective tax rates north of 60% because 280E is the IRS’s medieval torture device.

45%+ of “multi-state operators” are over-levered and drowning in debt like college kids with their student loans.

So everyone says the same thing:

“We’ll just go international. Less competition. More upside. Cleaner markets.”

Yes. But also NO.

International IS an opportunity… it’s just not the one you think it is.


THE ACTUAL RISKS (THESE ARE NOT THEORIES)

Currency risk
— Mexico, Colombia, Israel, Thailand have all experienced 5–35% currency swings in the last 18 months. Your “15% margin” becomes a rounding error.

Political volatility
— Governments change & cannabis policy gets rewritten in the hallway on the way to the vote.

No brand memory
— Your U.S. brand means nothing to a consumer who has never seen THC sold legally… ever.

Supply Chain Reality
— “We have a distributor” ≠ you have distribution. You have a person with a PDF and enthusiasm. Ask anyone who has done cross-border THC/GMP transport.
The paperwork alone can send a grown adult into silent prayer.


SO WHEN DOES INTERNATIONAL WORK?

When you stop trying to export identity and start importing infrastructure.

The winners will be the ones who:

1. Partner with local operators who already own distribution
2. Don’t show up loud but show up boring
3. Aren’t dependent on the U.S. capital mood swings
4. Understand on-premise unlocks will take years, not quarters
5. Oh and you know…have a grown-up strategy!


WHEN DOES IT FAIL?

When you think: “We found a supplier and a buyer… we’re global now.”

No, you’re not.

You just created a customs liability and a future LinkedIn apology tour.

I am bullish on international markets. 

There is real opportunity.

But don’t confuse “different” risk with “less” risk.

International is not your lifeboat.

It’s a rope bridge in a windstorm.

Still walkable.

Just don’t do cartwheels on it….

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.
✨

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The Battle

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