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

Give me $10 on Pump #6 and a case of THC Bevs!

WAIT WHAAAAAAT??

This is Circle K 2026 baby!


>> What’s Happening?

A Circle K franchisee in DFW started selling hemp-derived THC beverages.

This is the 1st major C-Store in Texas to stock THC drinks on shelf.

Lots of SKUs and get this…in-store tastings planned throughout 2026!


>> Why Does This Matter?

This ain’t a trial folks. This is mainstream retail entry.

Circle K is as mainstream as it gets. A roadstop brand with millions of daily customers.

Regulatory limbo? Who cares… make money when consumers buy drinks.


>> What I’m Watching

Can THC drinks outperform impulse staples like coffee and Red Bull?

How do Texas policymakers respond to non-dispensary THC sales?

Who’s next to join the party…Flying J??


The future of THC is in the cold box next to your protein shake.

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Is this the FIRST MAJOR ON PREMISE shot fired for THC beverages??

WELCOME to the 2026 Stadium EXPERIENCE!

THC Drinks are coming soon to an ARENA NEAR YOU!


>> What’s Happening?

Chicago’s United Center just announced its serving hemp-derived THC drinks.

Concerts/Sporting events/Big shared moments.

In case you didn’t know, that’s alcohol’s home turf….

THC is showing up more and more, without asking ANYONE for permission.


>> Why Is This Important?

Booze vs. THC is not the point.

The point is THC is now competing for share of occasions.

Normalization comes from repetition in trusted environments.


>> What Am I Watching?

The first league, venue group, or national operator that treats THC beverages in the same way ?

Who puts up the first THC Beverage advert in a stadium? (Remember USC/ Cookies?)

What major sports/food/airport group jump in next ?


5 beers or 5 2MG THC Beverages??

Same night, VERY different morning

A long held belief just got UPENDED last week:

Vapes just eclipsed FLOWER in terms of sales in CA.

YUP. WILD.

So, ask YOURSELF why…


>> What Happened?

In CA, vape products overtook flower as the #1 seller in licensed dispensaries.

This is a HISTORIC first in the U.S. legal market.

In 2025, vapes pulled ahead, with higher monthly sales and widening share


>> Why Does This Matter?

Flower has been KING forever.

Economics, culture, product…it was Michael Jordan.

Now the consumer wallet has shifted its preferences.

And upended norms (hello Gen Z!)


>> What Am I Watching?

Is Gen Z the demand anchor we should be trying to reach?

Does margin in vapes continue if this trend sticks?

Does quality and testing MATTER, or is price #1?

How does this change the retail plan-o-gram??


Flower has to take off its crown, for now…

But let me be clear: I don’t think flower is losing its heritage or dominance, YET….

I do think that consumer choice and pricing show us how the market is shaping the future…

Little more love from the MJ BIZ scene...
Shout for Rectitude Partners LLC
and my man Nicholas Bowers

thanks to the squad at 

Fat Nugs Magazine
Puff Creative

for a great night....4 Grams...COMING!!!!!

Guess who just figured out how to crack the Show Me State:

My guys at Jeeter - a DreamFields Brand + Elevate.

Keep telling me cannabis is a commodity business….

Jeeter just walked into MO and reminded everyone what a REAL BRAND looks like.


>> What’s Happening?

Jeeter, the No. 1 pre-roll brand in the U.S., just launched in Missouri.

They hit the ground running with a smart partnership with my guys from Elevate (GREAT TEAM) and hit 70 %+ day-one coverage of doors

These guys are going to CRUSH.


>> Why Is This Important?

Brand dominance via culture, community and premium perception.

Missouri is a BEAST with 4-6 groups there KILLING IT and MAKING MONEY.

Jeeter + Elevate treated this one like a brand build, not just a SKU drop.


>> What I’m Watching

Does Jeeter’s lifestyle strategy expand average ticket or just front-load hype?

Can culture from places like California translate to Show-Me economics?

Does this push a pre-roll war in the Show Me State?


Missouri didn’t “get” Jeeter. Jeeter chose Missouri.

Pre-rolls are crowded. Brands aren’t.

Jeeter + Elevate = WINNING.

So did you REALLY think the ban was about hemp??

No no no.

It was about ALCOHOL.

And now the numbers are in:


>> Whats Happening?

Alcohol is done watching hemp from the sidelines.

In Q4 2025 a bunch of companies files highlight lobbying disclosures tied to intoxicating hemp:

Moët Hennessy
Bacardi
Diageo
Brown-Forman
The HEINEKEN Company
Sazerac Company

Hmm….read the tea leaves and follow the money.


>> Why Does This Matter?

Lobbying is balance-sheet-based muscle memory for alcohol.

They have been doing it since 1950 and they are GOOD at it.

Make no mistake, the alcohol industry is acknowledging something BIG:

THAT intoxicating hemp is already part of the adult-use landscape.


>> What I Am I Watching?

Which alcohol players move from lobbying to minority investments?

Or does alcohol flex harder to push hemp off the shelves?

Can cannabis incumbents realize they were out gunned (and outspent)?


Not sure how this plays out but I am going to crack 10mg bev and grab the popcorn!

The hemp ban is coming annnnnnnd it's going to be unenforceable. Full stop.

Everyone screaming "shutdown" is missing the point.

The math just does not math…

>> What's Happening?

Lawmakers have stuffed an effective intoxicating-hemp ban into federal language.

On paper, it tightens THC limits and nukes most hemp-derived products.

In reality, it hands enforcement to agencies that already can't enforce federal cannabis prohibition today.


>> Why Is This Important?

We already ran this experiment.

Cannabis has been federally illegal for decades and yet here we are with regulated markets in most states.

The federal government does not have the manpower, political appetite, or operational clarity to police every convenience store, DTC website, and warehouse in America.

A ban without enforceability isn't regulation ? Just funny…


>> What Am I Watching?

States quietly filling the vacuum with their own rules while Washington argues with itself.

Hemp operators adapting structures, formulations, and channels instead of disappearing.

Cannabis incumbents cheering a "win" that may actually strengthen the very gray market they hate.


You don't fix consumer demand with a memo and you can't kill markets with paperwork.

If lawmakers actually want control, safety, and tax revenue, there's only one answer:


Regulate it and LEGALIZE IT…


Don't pretend you banned it.


If this sounds familiar, it should. We've been here before….

Guess who’s messin’ with Texas?? Cann, that’s who.

Cann is fixin’ to dominate the Lone Star State.

Here’s what’s going down:


>> What’s Happening?

Cann secured Texas distribution with Spec’s.

Spec’s, for those that don’t know, is THE LARGEST beverage retailer in Texas.

Full SKU set in one of the biggest alc retail channels in the USA.


>> Why Is This Important?

This is not a test, a dispensary, one franchisee gone rogue, or a limited run.

THC drinks are moving via mainstream beverage infrastructure.

Spec’s has 200+ doors statewide.

Say what you want, I AM seeing a distribution shift...


>> What Am I Watching?

What other brands can howdy on down to distribution?

What other retailers jump on board now that we have Target, Circle K and Spec’s?

Is there movement on the regulatory side in Texas? (Remember a few months ago they tried to BAN HEMP??)


Want to make sure we give a big congrats to the Cann Team!

Jake B. and Nick Fasano 👏 👏

Feels like Danny Stepper and the LA Libations team left their fingerprints all over here, cause this ain’t my first rodeo…

Want to LEARN MORE? Get your spurs to The Beverage Forum April 2026.

Hang 10 and hit the dispo??

Adult use cannabis may be coming to the Aloha State…


>> What’s Happening?

Hawaii lawmakers filed legislation that would put rec cannabis to voters in November 2026.

If passed by a two-thirds vote in both chambers, Hawaii voters would be asked whether to amend the state constitution to legalize adult-use cannabis.


>> Why Does This Matter?

Ballot initiatives are cool but they are NOT a guarantee.

This was not brought forth by the electorate but by elected officials…

Not sure this get traction or mahalo…


>> What Am I Watching?

Do MSOs even bother modeling Hawaii as a near-term market?

Is capital ready to fund something in one of the worlds largest tourist economies?

Do voters notice they’re being asked to decide a policy?


Feel like another version of Pele’s curse.

Cannabis style…I will just grab a shaved ice.

Why can’t an MSO be successful in one of the BEST markets in the US?

Missouri is quietly becoming one of the most attractive cannabis markets in the country — WITHOUT the MSOs.

Go figure.


>> What’s Happening?

Curaleaf exited Missouri.

Not cut back. Not paused. EXITED.

And they are not alone. No major MSO has meaningful exposure to Missouri.

Yet MO is consistently ranking among the healthiest AU markets in the U.S…


>> Why Does This Matter?

Missouri breaks the MSO playbook.

Limited license structure, strong retail economics, rational competition.

Not race-to-the-bottom pricing.

This is the rare cannabis market where operators actually make money (REALLY).


>> What Am I Watching?

When do private equity and strategic buyers re-rate “boring” markets?

Does the next consolidation wave starts OUTSIDE the MSO universe?

Who comes out of this market as a winner?


Missouri didn’t fail the MSOs but the MSO model failed in Missouri.

Not every great market wants a national flag planted in it.

Sometimes the best markets are the ones Wall Street ignores.

Where do hemp beverages belong?

Well, what do we know:

1. They sure found a way to enter traditional distribution channels

2. Alcohol use is declining

3. Consumers are driving demand

With the hemp ban looming I'm not sure which way is UP.

So you tell me?

Thank you to my friend Peter Su, PBC-CP, CTP, CCBP, CRS, GRCP, GRCA, IDPP, CBE for having me on...

Why do you keep doing this LinkedIn thing ???

BECAUSE THE POWER OF PERSONAL BRANDING IS YOUR FUTURE.

Here's a case study:

Few years ago met Lisa Williams via LinkedIn.

She reached out.
We got to know each other
We have supported each others' collective journey.

Lisa Williams is: 
— A working mother
— An entrepreneur
— Who owns two businesses
— Keeps up with her content 
— And is a TOTAL badass!

About 2 years ago she purchased a product SHE believed in. 

Hello Again...Something to help female health, specifically menopause.

She started putting some videos on TikTok...

And guess what... last week SHE WENT VIRAL.

1,000,000 views
122,000 likes
5,000 comments
21,000 saves 
59,000 forwards

AND SO MANY SALES SHE COULD NOT KEEP UP.

NEVER QUIT. 
NEVER question if you should be posting.

And buy some Hello Again!

And check the video here: https://bit.ly/4qCX4sq

When you fail 3 times, why not try for a 4th??

That’s what PA is doing right now as the state makes its FOURTH attempt at a move to Adult Use.

Sure, why not??


>> What’s Happening?

My guy Shapiro gave his fourth budget address.

Increasing overall spending by 6% without broad-based tax hikes.

Oh and he put adult-use BACK on the table…AGAIN.


>> Why Does This Matter?

PA is surrounded by NJ/NY/MD/OH, all of which are pumping REC.

The budget conversation shows how much $ PA is leaving on the table staying medical.

How ELSE can you spend more and NOT tax the general public?


>> What Am I Watching?

This is now #4. Can it REALLY HAPPEN this time?

What will be the policy tradeoffs if this happens? Who loses?

Is THIS a state surrounded by AU finally admitting leakage is a tax policy?


Adult-use didn’t magically reappear…

It reappeared because PA needs the $$$.

Politics and budgets are not based on morality…

Bet your butt they are based on COLD HARD CASH.

And AU seems like a magical cash machine.

Everything's BIGGER in TEXAS? Well, Texas Original just bet the ranch.


>> What's Happening?

Texas Original just opened the largest medical cannabis facility in Texas.

They’re expanding cultivation and processing capacity to meet rising patient demand.

No change in law…no ballot initiative.

Just cash, concrete, steel, and CONFIDENCE.


>> Why Does This Matter?

Well son, you don't go build the largest facility inside one of the most restrictive medical programs in the country…

THIS is what early movers look like in medical states.

And might signal that regulators are comfortable enough to let serious operators scale.


>> What Am I Watching?

Does demand absorb this build?

Does the program allow for success?

Who’s the next operator is to break ground?


Texas ain't first.

It won't be loud.

But when it moves, it will move at TEXAS SCALE.


Cowboy UP y'all.

This will make some people uncomfortable.

Good. Read it anyway.


>> What's Happening?

A new study from the National Bureau of Economic Research suggests that legal marijuana access is associated with lower suicide rates among older adults.

Particularly once dispensaries actually open.

Not legalization on paper.

Real access. Real products. Real use.


>> Why is this Important?

Older adults deal with chronic pain, sleep issues, anxiety, isolation.

And guess what? They're also the group with the highest suicide risk.

When legal cannabis becomes available, suicide rates in this cohort go down.

Let's not pretend this is nothing while we happily prescribe opioids, SSRIs, and booze like Tic Tacs…


>> What Am I Watching?

How long policymakers keep saying cannabis has "no proven benefit" while data quietly stacks up.

Whether public-health conversations finally acknowledge harm reduction instead of moral panic.

Who actually cares about outcomes and who just cares about optics…


No one is saying cannabis is a cure.

But dismissing data because it challenges the norms is bad science and worse policy.

If legal access helps even a subset of people feel less pain, less despair, or a little more okay, maybe that's worth taking seriously.

Just a thought…

Montana, the Gold and Silver State, is going GREEN.

Montana’s cannabis market just put up a number…which I found very interesting.


>> What’s Happening?

AU retail in Montana threw up a record $327M in sales in 2025.

AU represents roughly 90 % of Montana purchases.

AND this growth came DESPITE falling retail prices per gram.


>> Why Does This Matter?

Pattern recognition: price compression + volume growth = real consumer demand.

Out of this, the state grabbed $60 million in tax revenue, underscoring how important this product can be.

Medical markets seems to vanish in the face of AU. Unclear how this moves in S3…


>> What Am I Watching?

Montana works because it’s not drowning in licenses or over-financialized.

Its relatively open licensing structure and modest population make it a unique case, but can it last?

It’s also a NO MSO Zone…proving that you don’t need MSOs for a sold adult-use market.

Low population, controlled rollout, limited speculation.


Markets like this don’t scale nationally, but they do expose what broke elsewhere.

Record sales are nice, but structural market health is the REAL story.

We’ll see what prevails here.

Best advice for a bad outcome: Let someone ELSE pick your dose.

Or worse still, let someone who knows NOTHING about dosing pick your dose…

Because that’s what’s going on


>> What’s Happening?

Food & Beverage put out an article on the “perfect dose” for HEMP Beverages.

At 2.5MG

2.5MG??

REALLLY???


>> Why Is This Important?

It reveals a gap between cannabis reality and every outside stakeholder.

2.5mg ain’t a “sweet spot”. It’s a training wheel AT BEST.

Alcohol didn’t scale on near-beer.

Cannabis won’t scale on microdoses dressed up as safety or wisdom.

Low-dose has a place. (THANK YOU Cann)

Calling it “THE PLACE” is telling me you don’t understand the market.


>> What Am I Watching?

How much mainstream “acceptance” does this get?

Is this the way Bev/Alc gets comfortable?? (You sure sell more cans at 2.5mg…)

How many consumers do not “feel” an effect at this level???


2.5mg is not the right dose.

If your entire thesis starts and ends there, you’re throwing darts blindfolded.

While congratulating yourself for hitting something, anything.

Think your business is HARD?

Try this:

1. Every state (and city) has a different set of rules

2. The Government taxes you at an exorbitant rate 

3.  Capital flow is weighted to larger and later-stage operators

4. There is very little capital to begin with...

Now tell me you product is not Federally legal...WELCOME TO C@NNABIS!!!!

Appreciate the love from Alex D. and the squad from The High Index for the spot!

Failing to raise capital in c@nnabis ?

Get yourself to where the decision makers gather in ONE ROOM
Hyped as always for another sesh with my folks from IgniteIt Cannabis
thats right...

I AM COMING DOWN THE PIKE...
February 10th, 2026
Westin Jersey City

I heard The Boss is playing a set....

Register HERE: https://bit.ly/49pHgUF

and use my CODE: SETH20

Patrick Lane Elliot Lane Javier Hasse

It’s NEVER a good idea to let government run a business.

Right??

Anoka, Minnesota is set to cut the ribbon on the Anoka Cannabis Company.

The first and ONLY city-managed dispensary in the U.S.

What could possibly go wrong??


>> What’s Happening?

A city running retail cannabis is like a turtle teaching people how to fly…

Bad idea for government to staff, regulate, and be accountable to voters.

This seems like a BIG departure from the usual “license it and pray” model.


>> Why Is This Important?

This city just decided licensing WASN’T enough.

Screw regulating private operators, Anoka wants to own the P&L too.

This is a fundamental shift for government FROM oversight TO asset control.


>> What Am I Watching?

How soon till every cash strapped municipality gets in the game?

Does this model work financially?

How does a city deal with illicit markets?

How long until they start growing weed and creating their own brand…??


Cannabis didn’t normalize…

It went on the city Balance Sheet.

Government is best which governs least, PERIOD.

Mark MacLeod

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.

Founder

I coach, advise and invest in the CEOs of high growth technology companies & help them execute game-changing deals.

I bought more shares of Shopify last week.

Shopify stock is already the single largest portion of my net worth.

Despite it being down 26% YTD, I doubled down.

Why?

The stable foundation of SaaS is going away. The idea that you can build a business with long customer lifecycles and zero marginal costs is gone.

SaaS isn’t gone. But the easy times of SaaS are gone.

I have always invested in founders. The thesis is simple: Get the founder right, and they will figure the rest out.

Tobias Lütke is a once-in-a-generation founder.

His technical depth and passion for the mission make him unstoppable.

If anyone can figure out how to transform a business through AI, it’s him.

The day he decides to race cars full-time, I will revisit this thesis. But for now, I am all in.

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Certified Personal & Business Performance Coach

Chartered Professional Accountant (CPA)

An exclusive community of VC and PE-backed CEOs who want
to scale themselves and their companies without limits.

Limitless is an exclusive community of VC and PE-backed CEOs who want
to scale themselves and their companies without limits.

I coach startup CEOs to grow themselves and their business all the way to a massive exit

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.

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

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

General Partner

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.

Interim CFO, Shopify
Advisor, Well.ca
Advisor, Cakemail 
Advisor, Dok Dok Inc 
Advisor, Raymark
Advisor, Sitezoogle 
Interim CFO, Status.net Inc.

Advisor & CFO

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.

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

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.

Strategic consulting assignments: 
•	Advised on the sale of two software companies and the purchase of an education services company
•	Led the successful restructuring of an insolvent retailer. The company is now thriving and expanding
•	Enabled the restructuring & strategic refocus of a new media company that resulted in a 3x growth in revenues and 5x growth in profit & cash flow

President

Was responsible for Finance, Alliances and Corporate Development functions. Raised $19M in equity over 2 rounds + oversaw growth to over 100 people. Established many key partner relationships

Director, Finance + Corporate Development

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

CEO, Shopify

Helping ambitious CEOs & founders scale world-changing companies without sacrificing their health, happiness, purpose, or humanity

I am leaning into my weirdness, and it feels good.

I have never been a stereotypical CPA. When I was in undergrad, I designed my life around raves. Classes were Tuesday - Thursday. This enabled me to go dancing all night Saturday and recover. 

While I love to serve, I hate having a boss. So, while my peers went the “Big 4” route, I joined a small firm serving founders. I have only ever been or worked with founders. 

I have always leaned into what I love. I love to write. When I look back, all of my most important relationships came from my writing. Tobi from Shopify. Mike from FreshBooks. The guys starting Real Ventures. All came in part because they read my thoughts.

Then there’s yoga. Starting casually in my late 20s, yoga has evolved to become the foundation of my life.

The stretches offered in most North American yoga studios are a tiny fraction of what yoga is. In fact, the word “asana” (that’s what these postures are called) is barely mentioned in the Yoga Sutras.

Yoga is a complete system for living your life. My goal is to live every minute in accordance with yogic practices and values.

I discovered kundalini yoga in 2012. I got serious about it in 2019. And I teach it now.

Kundalini focuses on building and directing energy. We all have dormant energy at the base of our spine. Through these practices (called “kriyas”), we activate and direct that energy. 

Studies have shown that this practice turns on dormant parts of your brain. It unlocks our potential.

All of this mix of yoga, breathwork, meditation, and human optimization has co-mingled with my startup experience to create Limitless. 

My mission is simple: to redefine how founders build companies by putting their energy, health, and inner alignment first. So they can scale without limits and lead from a higher state.

Change your life so you can change the world!

Hard to think of something more motivating to work on!

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

A CEO told me yesterday: "I hit $10M ARR and I've never been more miserable."

He's sleeping 6 hours per night. Hasn't seen his 1-year-old son awake in weeks. 

Can't remember his last meal that wasn't at his desk.

He thought this was the price of building something great. It's not. It's the recipe for failure.

Naval said it: "Startups die when founders run out of energy."

90% of startups fail because founders burn out before the company breaks through.

Here's what most founders miss: You are the leverage point:

Your clarity sets direction.
Your energy sets the pace.
Your state sets culture.

A depleted founder creates a depleted company.

The real work isn't optimizing your calendar or finding another productivity hack.

The real work is you.

When you're centred, everything works better: strategy, team, execution, growth.

Your nervous system IS your company's operating system.

This is what we're building at Limitless: founders who scale without breaking. Companies built from clarity, not chaos.

The world needs leaders who can make bold decisions without losing themselves in the process.

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

As Silicon Valley embraces 72-hour work  weeks with 9-9-6, I'd like to remind everyone of this gem from Naval:

"40-hour workweeks are a relic of the industrial age. Knowledge workers function like athletes – train and sprint, then rest and reassess."

Most CEOs I work with don't have a performance problem. They have a recovery problem.

They sprint all day. Every day. For years.

No periodization. No rest cycles. No reassessment.

Just grind until something breaks: Their health. Their marriage. Their company.

Limitless CEOs operate differently:

They train like athletes:
→ Intense sprints followed by real recovery 
→ Energy management over time management 
→ Strategic rest as a competitive advantage

Your output is a function of your energy. And energy requires recovery.

The industrial model rewarded hours logged.

The knowledge economy rewards quality of thinking. You can't think clearly when you're running on fumes.

Rest isn't the opposite of performance. It's the foundation of it.

You don't have to grind. You don't have to sacrifice health and happiness. There is a better way. Members of the Limitless.ceo community are learning how.

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

Limitless.ceo

Botkeeper raised $90M+ and just shut down after 11 years. It's a cautionary tale we all can learn from.

Raising capital is not a sign of success. It just means someone gave you a shot.

We celebrate fundraising like it's the finish line. It's not. It's the starting gun.

And sometimes it's the thing that kills you.

More capital means more pressure, higher burn, bigger expectations, and less room to figure things out.

Botkeeper never nailed product-market fit with accountants. But they kept raising anyway. I don't blame them. But this happens a lot with VCs overfunding.

$90M later, the outcome was the same as if they'd run out of money at $5M.
Except that more people got hurt.

The founders I work with who build lasting companies treat capital as fuel for what's already working. Not a substitute for what isn't working.

I used to work less, but was stressed out more. One year ago, I was coaching and running a record label, and trying to become a yoga teacher.

At its peak, I was spending half of my time on music. Either making it or growing the label.

I didn't realize the stress that this distraction was causing me until I focused. At the start of 2025, I gave the label to one of my artists to run. I still teach yoga, but as a hobby.

It hit me a year ago that I was diluting myself. The best coaches are just focused on that. The best athletes are maniacally focused on being the best. I needed to do the same. So, I let the label go.

My sole focus is on being the best version of myself so I can be the best coach I can be.

It is only in this new focused state that I realize I was actually stressing myself out before. I had no idea I was causing stress. I thought I was having fun and living my best life. 

I share this as an invitation for you to reflect on the level of focus in your life.

You are likely running one company. But within that, can you focus more? Do you have one clear strategic priority this quarter?

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For decades, I've watched founders kill themselves for their companies.

I know a founder who wanted to sell an organ to keep his company afloat. He later developed shingles from stress.

I've watched founders gain weight as cortisol spiked. Founders who can't sleep. Founders who are trying to be productive while running on fumes.

I wasn't immune. At FreshBooks, I had "freshmares", solving business problems in my dreams. I was physically home with my family, but mentally still at work.

When I ran my investment bank, I made fitness a priority. Daily yoga. CrossFit 4x/week.

It still wasn't enough. My first marriage ended during that time.

I loved the work. It was stimulating. Rewarding. But my company was everything.

Sound familiar?

Last year, I studied 11 CEOs who built companies collectively worth $11 trillion. I wanted to understand how they sustained and grew for decades while most founders burn out or plateau.

Here's what I found: They didn't just get lucky with product-market fit. They learned to scale themselves as they scaled their companies.

They made health a strategic priority, not an aspiration.

Most founders do it backwards. They sacrifice health for growth. Then wonder why they plateau.

Limitless founders flip the script:
Health → Energy → Clarity → Revenue growth → More energy.

It's a virtuous cycle.

Hustle creates short-term velocity and long-term damage. I've watched this story play out hundreds of times.

There's a different path.

If this resonates, check out limitless.ceo.

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Harry Stebbings says fundraising has changed.

According to Harry, SaaS founders growing 2-3x have two choices:

Use AI to accelerate to 8-10x growth. Or cut burn and never raise again.

The reality is more nuanced.

The real question isn't "which path." It's "how do I build OPTIONALITY so I can choose either, on my terms?"

Optionality has never been more important than it is now.

Optionality means:

✅ Your can get to cashflow break-even in runway if you are not there already.

✅ Your growth rate & unit economics let you raise if and when you want to.

✅You are known to your most natural buyers and can enter into a warm, qualified exit process at any time.

And a personal consideration here: 

✅ As founder, your energy and clarity let you make that strategic call from strength, not panic.

The founders who win in this market aren't picking door 1 or door 2.

They're building a company, and a version of themselves, that can walk through whichever door makes sense, whenever it makes sense.

That's not simple. But it's the real game.

Founder @ 20VC

I asked a CEO client to rate his happiness. He said 6 out of 10.
I asked what would make it a 10.

His answer wasn't more revenue. Wasn't a bigger team. Wasn't closing a round.
It was spending more time on things that create energy.

He already knew the answer. Most founders do.

The gap between a 6 and a 10 isn't more success.

It's less of what drains you and more of what fills you up.

The hard part isn't knowing this. It's giving yourself permission to act on it.

Energy isn't a reward for building something great. It's the requirement.

Design your role, company and life around energy and you become limitless!

Bad decisions come from bad states.

Most CEOs make decisions from fear, panic, or impulse. Then defend those decisions as if their life depended on it.

The fix is simple: change your state first. Before any major decision, get grounded:

- Breathe
- Calm your nervous system
- Find neutral

A calm mind sees clearly. A panicked mind sees threats everywhere.

A calm mind can more easily access intuition. When that happens, decisions become effortless.

The decision you make from clarity will be better than the one you make from chaos.

And you won't need to cling to it. You'll just know it's right.

State first. Decision second.

Chili Piper co-founder Alina Vandenberghe joined me on The Startup CEO Show recently and dropped some gems.

A few highlights:

Her personal social media drives 50% of Chili Piper's pipeline. She spends 40% of her time on it. And it works because it's authentic, not forced.

She grew up in communist Romania. That resourcefulness shaped how she bootstrapped to $3M before raising.

She co-runs the company with her husband. 150 people across 38 countries. No middle managers. Every decision is documented and transparent.

Her take on personal branding: don't do it unless it brings you joy. If it feels forced, it won't work. Find someone else in your company who loves it.

If you missed the pod, the full interview link is in the comments.

Co-founder & co-CEO @Chili Piper 🔥 Here I talk about lessons I learned to jumpstart my career from intern to SVP. And to grow a company from 0 to almost $1Bn

Most founders optimize their GTM funnel. Almost none optimize the machine that runs it all.

I recently sat down with Greg Newlands, a fitness coach who works with founders.

Full disclosure: Greg is my coach and also works with several of our Limitless founders.

One thing he said stuck with me:

"If I'm not sleeping well, not exercising, not rested, I just don't perform the same in life or in business."

That's not a wellness quote. That's an operating reality.

Greg trains entrepreneurs the way athletes get trained: 
Strategic breaks throughout the day. 
Resistance training as a non-negotiable. 
Tracking four daily KPIs for energy and performance.

The part that hit hardest: he burned out multiple times before he stopped treating rest as the enemy of progress.

Sound familiar?

This is one of the most tactical conversations I've had on health as a founder strategy.

Full episode on my blog → link in comments.

A CEO asked me last week what my superpower as a coach is. I gave two answers:

1.) I have been on every side of the table: CFO, VC, banker. I have raised over $1B in funding and closed over $1B in exits. This is why my 1-on-1 coaching is only for CEOs who have raised VC or PE. You are on a 1-way path that I know well.

2.) Building a company is a spiritual journey. It transforms you. You change every year. You need to break through your limits again and again. 

I bring everything I know from the modern startup world, coupled with ancient yogic wisdom, to help founders transform. This is what we are doing with Limitless.ceo

It’s always a thrill when a client goes all the way to a life-changing exit. This is my goal as a coach. Help CEOs grow faster than their companies all the way to exit.

Massive congrats to Chris Bache on the sale of Hatch to Yelp. He built a capital-efficient machine. Owned his category and created massive value for his customers, staff, and investors.

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Cofounder/CEO @ Hatch | We’re Hiring!

150 years ago, most people were healthy. Today, most people are sick.

Justin Mares, founder and CEO of Truemed, has been on a journey of self-discovery. He doesn't like what he found.

What he has discovered impacts all of us.

Tune into this week's episode of The Startup CEO Show to learn more.

The healthy person has a hundred priorities; the sick person has one: to be healthy.

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CEO, Truemed

I cringe when I think of how underslept I used to be.

It started in my late 20s. I was DJing a lot. Even on weeknights. I was CFO at my 1st startup at the time. My schedule was all over the place.

Then I became a Dad. Any parent of young children knows what that’s like. Our kids are 372 days apart.

When I got serious about yoga, I would wake up at 5am to practice. It was the only way to fit it into my schedule. This was at the cost of sleep.

I still drank a lot. Or I should say, often. Not a lot. This was my wind-down. My ritual. But I now know it came at the cost of sleep.

Looking back, even with a deep yoga practice, I was prone to anger. I was foggy. I couldn’t function without coffee.

This is the default state for most founders. In fact, we glorify this stereotype. We celebrate founders who sacrifice everything to build.

A few years ago, I flipped things. I made sleep the priority. I read Matthew Walker’s "Why We Sleep" and realized everything I was doing wrong. 

I started tracking my sleep and making changes to improve duration and deep sleep.

This has been a life-changer. I have more energy, clarity, and happiness than ever.

I tell my CEOs all the time: Sleep like it’s your job, because it is.

Today’s performance began last night, based on the quantity and quality of your sleep.

Your sleep quality and duration determine what you can accomplish today.

Rather than being the 1st thing to sacrifice to create more work time, sleep is your top priority.

Don’t work until you can’t, then crash. Have a wind-down routine that enables you to drop into a deep, restorative sleep.

If you want better results and a better life, make sleep your focus.

You will be a better founder. You will be a better human.

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Every founder has a financial dashboard. Almost none have a biological one.

At Limitless, we think about CEO performance across three dimensions:

Physical → sleep quality, HRV, recovery.

Mental → deep work hours, focus time.

Financial → MRR, pipeline velocity, growth.

(We also go deep on spiritual, but let's park that for now...).

Here's what most founders miss:
These aren't three separate dashboards. They're one system.

✅ Your HRV predicts your decision quality.

✅ Your sleep predicts your deep work capacity.

✅ Your deep work predicts your revenue.

The financial metrics are the output. The biological ones are the input.

Fix the inputs. The outputs follow.

Revolut CEO Nikolay Storonsky nailed the metaphor for the senior leader you want.

For Nik, he wants leaders that are heat-seeking missiles.

You point them at a target, give them a problem, and they go. They complete the mission.

This is leverage. This is the bar for your talent. 

Too many CEOs compromise on senior leaders. Either they are too busy to notice. Or, more often, they know a change is needed. But it’s going to take time, so they wait. And hope the person will keep up with the company's growth.

If you are not surrounded by heat-seeking missiles in your company, you know what you need to do.

Make the change. Never compromise. Your leaders are your leverage. Your leaders set the bar for culture and performance.

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Jack Dorsey, founder of Twitter and Block, just gave us a lesson in making hard decisions.

Often, when faced with decisions like layoffs, the temptation is to do the minimum necessary. To avoid as much pain as possible. 

Jack did the opposite. He leaned into the pain. He cut 40% of Block's workforce. Over 4,000 people. In one move.

Not because the business is struggling. Gross profit grew 24% last year.

He did it because he saw where AI is heading and decided to get there first. He leaned in.

Dorsey said it clearly: “Repeated rounds of cuts destroy morale, focus, and trust.” He'd rather take one hard, clear action than manage a slow bleed toward the same outcome.

You can disagree with the decision. But the leadership principle is worth studying.

The hardest decisions aren't hard because you don't know what to do. They're hard because you don't want to feel the pain of doing it. They're hard because you resist.

So you delay. You half-measure. You spread the pain out over months, hoping it hurts less.

It doesn't. It just hurts longer.

Whether it's a layoff, a co-founder conversation, or a pivot you've been avoiding, the cost of the slow path is almost always higher than the cost of the decisive one.

Suffering = pain * resistance. If you don’t resist what you need to do, you will not suffer. 

It’s no surprise that Jack took this approach, given his spiritual practice. Jack does long Vipassana retreats. Anyone who has done these will know that they are painful but always worth it.

The way out (of whatever issue you are struggling with) is through. Lean into the discomfort. Make the bold call.

Want to learn how to build and scale a marketplace?

Mark Bordo has done it three times over 25 years.

His latest company, Vetster, became the leading pet telemedicine platform in North America. In this interview, he shares the playbook:

→ Why you build supply before demand
→ How data drives every decision at scale
→ Why most marketplace founders focus on the wrong metrics
→ The regulatory battles that almost killed the business
→ How persistence beats strategy every time

If you're building a two-sided marketplace or thinking about starting one, this conversation is packed with tactical lessons.

Co Founder, CEO at Vetster Inc.

Nick Mehta built Gainsight into a $235M revenue company and essentially created the customer success category from scratch.

Tier-one investors. Best place to work on Glassdoor. Sold to Vista Equity.

But the part of our conversation that stuck with me most had nothing to do with any of that.

It was Nick talking about detachment.

About reaching a point where the fundraising milestones, the lists, and the external validation just stopped mattering as much. 

Not because he failed. Because he succeeded and realized it wasn't the point.

He talked about holding two ideas at once: being all-in on what you're building while accepting that, eventually, it all fades.

That's a rare kind of clarity from a sitting CEO.

We also dug into how he created a category with almost no TAM, how he navigated tier-one VCs like Bessemer and Lightspeed, and why he structures his time around what gives him energy rather than what drains him.

If you missed our podcast, here is the interview.

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