Founder of StrategyBreakdowns.com

TLDR: Worked in strategy consulting → Joined strategy team at Atlassian → Started writing strategy case studies → People liked them, so I left my job and went full-time

Tom Alder

8 things I've learned while living in Valencia for the past month:

1/ The "slow" culture made me realise how much day-to-day urgency you experience everywhere else.

2/ Europe is the best timezone - 4 hours of deep work before US Eastern gets online.

3/ The city is easy-going and beautiful, but not efficient. Restaurants with lines out the door and empty tables, busses show up 15 mins late (or not at all), 'the system is down' is almost a daily occurence.

4/ I love a siesta but find it nearly impossible to refocus afterwards. Better for marking the transition from work → life.

5/ Meeting people as a digital nomad requires more intentionality than I thought. 

6/ Everywhere you look, you see someone's creative touch. Tiles, balconies, door handles. Everything is decorative, even if in a small way. 

7/ I didn't see a single person on a laptop in a cafe. 

8/ Paella is more than just a regional dish. Everyone is quick to recommend their favourite spot, share tips and rules for ordering it correctly, and tell their Paella-based memories. People worship it here (rightly so!)

—

👉 P.S. If you enjoyed this post, you'll love my newsletter - a 3-minute breakdown of the strategy playbooks and growth hacks behind the world’s greatest companies.

Join 100,000+ strategy nerds from companies like Google, Meta, Atlassian, and Netflix: https://lnkd.in/g2FWfXGR

The team at beehiiv just showed me what they're launching next week.

I've analysed hundreds of product releases.

This one I'm gonna join live.

Most companies make tweaks and add tiny features.

beehiiv have been quietly building something that got me absolutely hyped.

Tyler Denk 🐝 and team have cracked something fundamental about how creators grow and monetise.

I can't share specifics (NDA), but here's what I can say:
If you're building a creator/media business in 2025, you should join us at the launch event!

Register here → https://lnkd.in/gh3tKmCZ

People always ask "How did you decide when to quit your job and go all-in?"

3 months after launching Strategy Breakdowns I told my boss I was leaving.

This was my napkin math:

The business was making just under $3k/mo.
~$2.2k from newsletter sponsorship, rest from affiliate revenue.

→ I was publishing 1 newsletter every 2 weeks
→ If I ran them weekly, that'd 2x sponsorship + 1.5x affiliate revenue

→ I had 1 sponsor per newsletter
→ If I had 2, that'd 2x sponsorship revenue again

→ I had 20k subscribers
→ If I grew to 50k, that'd 2x sponsorship + 1.5x affiliate revenue again

Q: If I quit my job, would the extra 40hrs per week be enough to publish 1 extra newsletter every 2wks, sell 4x as many ads, and speed-run an extra 30k subs by reinvesting all revenue into subscriber growth?

Once I laid out all the inputs, it became an easy 'yes'.

I could probably hit $10k/mo within a month or 2, even factoring some contingency if I couldn't sell 100% of my ad inventory.

Then if I kept growing the newsletter, and added new ways to monetise, I figured it wouldn't be too much drama to get to $20k/mo.

Quitting a high-paying tech job for a $3k/mo newsletter = crazy, risky, scary
Quitting a high-paying tech job for a (soon-to-be) $20k/mo newsletter = makes sense

Same business. 
Different frame.

Don't be afraid to math it out.
Goes a long way in building up conviction.

—

👉 P.S. If you enjoyed this post, you'll love my newsletter - a 3-minute breakdown of the strategy playbooks and growth hacks behind the world’s greatest companies.

Join 100,000+ strategy nerds from companies like Google, Meta, Atlassian, and Netflix: https://lnkd.in/g2FWfXGR

Valve makes $50 million per employee.

Microsoft? $18 million.
Apple? $2.4 million.
Meta? $1.9 million.

How does a 350-person gaming company eclipse every tech giant on the planet?

→ They built a 30% tax on PC gaming.

Every game sold on Steam. Every microtransaction. Every indie hit and AAA blockbuster. If it's sold on their platform, Valve takes 30%.

They do develop games themselves, but vast majority of their revenue comes from infrastructure, maintenance, and collecting.

What makes it even more remarkable:

Zero traditional management mechanisms.

Valve operates with a completely flat hierarchy. No managers assigning work. No executives approving projects.

Instead they pioneered several radical workplace practices like choose-your-own team, and peer-reviewed bonuses.

Your colleagues (not your boss) determine your compensation based on your contributions. The entire company votes on your impact.

The result:
336 employees shared $444 million in total compensation in 2021. That's an average of $1.3 million per person.

And the company is on track for $17 billion in revenue in 2025.

They proved something most large corporations forget:
You don't need more people. You need the right structure (business model + organisational model).

—

📖 If you liked this post, you’ll definitely enjoy my newsletter article Why Valve has no managers!

Take a look here: https://lnkd.in/gyDPxJQ5

Imagine you are a marketing manager working for Coca Cola in 1971.

To make your most important decisions, you might have access to things like:
• Sales info
• Customer surveys
• Financial metrics

IF you spend a few days (possibly weeks) digging around the company for them. Remember, no computers back then.

Now, imagine you had instant access to:

→ The 5x highest performing newspaper/billboard/bus-stop ads out of the 10,000’s of ads Pepsi Co are running globally.

→ Real-time dashboards showing the number of daily, weekly, and monthly walk-ins for a McDonalds store that you’re doing a deal with.

→ A system that tracks every soft drink consumer in the world, showing you exactly what magazine they are most likely to get their beverage news from, and accurate trend data showing you a spike in conversations about “sugar-free”.

All entirely for free, fully self-serve, without ever needing to contact any Pepsi staff, McDonalds partners, or magazine analysts.

That is the world we live in.

But most people don't fully appreciate this. 

Every internet user and interaction leaves digital footprints. These footprints (if you know where to find them) reveal insights that make traditional ‘strategy theory’ feel like guesswork.

Not leveraging an 'information advantage' for your most important decisions, projects, products etc today is like voluntarily boxing yourself into a cubicle at Coca Cola HQ in 1971.

My vote: let’s use the tools available to us!

That's why I created 'Websites & Traffic' - a training that transforms you into a modern data-driven strategist.

If you want to skyrocket your persuasiveness, impact, and progression (but you’re looking for a modern-day approach that doesn’t involve slugging through more abstract ‘strategy theory’), this is for you! 

→ https://lnkd.in/gcWA7dyd

POV: You launched something and 1500+ people show up at once.

No paid ads. 
No viral post. 
Just an organic launch email.

Here's what the hype is all about:

Yesterday I launched 'Websites & Traffic'.

It's a training bundle for strategic professionals who need to back up their ideas with persuasive data. 

In just 5 days, you'll master 28 specific tactical skills that let you reverse-engineer any company's digital strategy - whether that's:
- Your #1 competitor
- A potential customer you're trying to close
- The market leader in your space
- Your highest-risk vendor
- Or simply a company whose strategy you want to learn from.

This isn't old school 'competitive analysis'.

These data-driven strategy skills are must-haves in today's age for just about any strategic use case:
- Preparing for customer interviews
- Increasing your own company's reach
- Analysing any player in your market
- Evaluating partnership opportunities
- Researching prospects before sales calls
- Investigating a trend you want to capitalise on

It works even if you've never heard of SimilarWeb, don't know what a UTM parameter is, and think "organic traffic" just means the line at the farmers market.

If you want to walk into your next big meeting as 'the person who always has the data', check it out → https://lnkd.in/gcWA7dyd

Why change fails. Brilliant. 

Source: Lippitt-Knoster Model - The 5 Components of Organisational Change.

Amazon website from every year since 1997, in chronological order.

—

👉 P.S. If you enjoyed this post, you'll love my newsletter - a 3-minute breakdown of the strategy playbooks and growth hacks behind the world’s greatest companies.

Join 100,000+ strategy nerds from companies like Google, Meta, Atlassian, and Netflix: https://lnkd.in/g2FWfXGR

The Amazon website every year since 1998

AI NEWS: Fyxer AI ($1→25m ARR in 12mo) just dropped the biggest upgrade to their core product since launch.

Here's everything you need to know:

Fyxer's core product "Drafts" lives inside Gmail/Outlook, and it auto-drafts email replies in your voice for you to review, edit (if needed), and send.

They just released "Drafts 2.0" with a wall-to-wall revamp of product improvements:
→ better context searching (remembers past conversations to reply how you would)
→ dynamic tone detection (adapts to who you're emailing - client, manager, colleague etc)
→ smarter call scheduling (handles time zones automatically and finds times that suit everyone)

The result: users are now sending *twice* as many email drafts without edits.

Check out the draft it wrote below.

For anyone spending an hour+ on email: this is one of the apps that actually saves me tangible time + focus on a daily basis. 


For the product-led-growth nerds - onboarding is slick too. Starts working in 30 seconds with Gmail or Outlook signup. Automatically learns your voice. Zero setup or learning curve.

I love startups like this - simple idea with perfect execution.


Oh and I convinced the Fyxer team to give my readers a special signup offer https://lnkd.in/gsuYEPQP (Partner link)

This is how you print $$$ by running ads in newsletters:

(And no, it's not generic copy + CTA to 'sign up now')

I've run 100s of ads in my 100k reader newsletter.

Worked with the best growth marketers in the world at companies like Atlassian, Clay, Vanta etc and I think I might have the highest renewal rate in the industry.

Here is the no-fluff playbook for getting results from newsletter ads:

1/ Less is more.
Longer ad copy (and longer sentences) ALWAYS perform worse. This may seem counterintuitive, I know it's tempting to write paragraphs about your product, but the quicker readers can internalise your message the more likely they'll read it in full. Aim for ~3 sentences / bullets total.

2/ Scannable format
Our best performing ads have the following characteristics:
- Start with a catchy, intriguing, spicy headline in *bold*
- Short punchy lines/lists with line breaks for breathing room
- Button with unique CTA ("Show me my security score", "I want the free playbook")

3/ Specific objectives.
Don't assume the newsletter knows what you want. People default to impressions/clicks, but every time I dig deeper there's a more important goal: "I want our founding story going viral", "I want a pretty report with data and community screenshots to share with my boss (my promotion is coming up)", "I want to run an isolated test to see if a waitlist/free trial/free plan works for us". 

4/ Don't just run 1 ad. 
I'm not saying this because more ads = more spend. There are 3 reasons you NEED to test with multiple ads: a) it takes multiple touchpoints for decision-makers to take action (when was the last time you saw a brand for the first time and 30s later you're on a $99/mo plan?), b) you test multiple angles to learn what resonates, c) most newsletters do bundle discounts so its cheaper per ad/open/click. 1 ad = throwing money away.

5/ Keep a swipe-file.
Seems obvious but not enough people do this. Collate your highest-performing social posts. Your competitors' best FB ads. Your best-converting landing page. Leverage these for your ad copy - don't ever start from scratch.

6/ You want partnership, not just sponsorship.
If your 'partner' isn't actively helping you tighten your copy, learn from the data, leverage their high-performing assets, investing their own money + time + resources into ensuring you win, you need to run.

7/ Backend funnels are magic.
This might be the most important alpha of all. The sponsors that are ripping right now do some variation of: run ads to a lead magnet/webinar → capture email → survey to segment (optional) → email nurture with education + social proof + objection-handling → sales handoff to book a demo/whiteglove/welcome offer. 1 person can build this in 1 day with AI, and it gets >10x better results per ad.

I have just 3 ad slots in my newsletter left this year, then I'm increasing prices for '26. 

If you're targeting strategy nerds (founders, PMs, devs), DM me!

5 unconventional tactics I learned at Atlassian (your company should copy these):

1. Everyone reads customer feedback (literally everyone)

Every week, every employee gets an automated email with 3 randomly selected verbatim quotes from customers. Bug reports, success stories, feature requests.

Over time you start spotting patterns. You develop intuition for customer sentiment. When you're proposing something, you can back it up with qualitative data you rememeber reading.

2. No PowerPoint allowed, only memos

Good writing is good thinking. You can disguise terrible ideas with pretty slides.

Every idea, every meeting, every project, every roadmap lives as a Confluence page. Writing out your ideas forces you to get specific about what you actually want to say (and why it matters). 

3. Every team has visible KPIs

Based on your team and role, you always knew exactly what metric mattered most. OKRs aren't perfect, but they create MASSIVE clarity of direction.

You also always knew what your KPI was driving at the division or company level (ie. what it "rolled up" to). Month commentary from owners explaining movements makes it easy to tell what matters to teams across the whole company. 

4. Open by default

Jira boards and Confluence pages have full organisational sharing permissions toggled on by default. This is a small but hugely significant product design choice.

Unless you actively close it off, everyone in the company can find, read, and comment on your work. Google Docs and Word don't do this – which means every new doc feels "yours" instead of "ours." 

5. Roll out to employees first

When I worked there, Atlassian had over 10,000 employees. That's a pretty sizable testing ground, and every mature product team would roll out changes to Atlassians first (who were using these tools every day).

This lets you catch bugs and bulletproofs ideas before paying customers see them, and creates a friendly space for candid feedback.

The pattern: make transparency and feedback the default (not the exception) for every product, decision, and idea.

Happy building.

—

👉 P.S. If you enjoyed this post, you'll love my newsletter - a 3-minute breakdown of the strategy playbooks and growth hacks behind the world’s greatest companies.

Join 100,000+ strategy nerds from companies like Google, Meta, Atlassian, and Netflix: https://lnkd.in/g2FWfXGR

Strategy & Finance Executive | Scaling Impact-Driven Companies Beyond $10M | Strategic CFO | Certified Scaling Up Advisor

Scaling Founders Beyond $10M with Strategy, Financial Clarity, and Leadership Expansion

Most companies stall not because of lack of effort—
but because the founder has outgrown the systems, strategies, and financial models that once worked.

At Ascend Growth Ventures, we partner with CEOs of $3M–$10M companies to implement Scaling Up, strengthen financial infrastructure, and elevate leadership teams—building businesses that scale profitably and predictably, without burning out the founder.

By integrating Scaling Up, Exponential Organizations, and CFO-level financial insights, we deliver a complete, battle-tested system for sustainable, high-performance growth.

🔹 We Work With CEOs Who Want To:
✔️ Scale revenue and profits without chaos
✔️ Build self-managing leadership teams
✔️ Unlock hidden cash flow and improve financial decision-making
✔️ Sharpen their strategy for exponential growth
✔️ Prepare for capital raises, acquisitions, or exits

🔹 Our Core Focus Areas:
  * Strategic Scaling Up Implementation

  * Financial Strategy & Cash Optimization

  * Leadership Team Development

  * Systems for Predictable Growth

  * Valuation Prep and Exit Strategy

✅ Why Work With Me?
25+ years of experience scaling businesses from the inside out:
➡️ Regional CFO, GE Gas Power (LATAM, +1.5GW record year)
➡️ Strategic finance and underwriting leadership at GE Capital
➡️ Business/project development for 8-figure ventures
➡️ Trusted advisor to founders scaling past $10M and beyond

✅ Industries We Specialize In:
✔️ Clean Energy & Decarbonization
✔️ Industrial Goods & B2B Services
✔️ Impact-Driven Companies
✔️ Scaling Coaching & Consulting Firms

🧠 If You're Ready to Scale Intelligently and Sustainably

Let's have a strategic conversation about where you are—and where you can go.

Easiest way to work with me?

Book a private power hour call and let's create your vision.
https://calendly.com/cruzagamboa/90-min-power-hour

Cruz Gamboa

Some companies don’t stall because of strategy.
They stall because of perception.

You can have the right model, metrics, and playbook—
and still struggle to scale
because trust isn’t in the culture.

We think scaling is about systems, KPIs, and offers.
But it’s really about energy, alignment, and belief.

Teams don’t reject initiatives.
They reject inconsistency.
They sense when the leader says one thing
and embodies another.

Every interaction in a growing company is a mirror—
it reflects the culture that’s actually being built.

Before you refine your next OKR,
refine your presence.

Because the best strategy in the world can’t fix a trust gap.

➡️ People follow clarity before they follow goals.
➡️ Integrity scales faster than intensity.


#leadership #scalingup #growth #trust #mindset

The market tells stories. Your financials & metrics tell truth.

In 2001, Amazon's stock cratered from $113 to $6.

Wall Street declared it dead.

Let's be clear: that had to be terrifying. Even for Bezos.

Watching 95% of your valuation evaporate. Hearing the whispers. Feeling the pressure from every direction.

But here's what separated him from founders who fold in those moments, he kept coming back to his dashboard:

Customer acquisition costs...improving. 

Fulfillment efficiency...improving. 

Contribution margin per unit...improving. 

Defect rates...declining.

The stock price reflected fear. 

The operating metrics reflected reality.

Confidence isn't the absence of fear. It's choosing to trust what you can measure over what you can't control.

This is Financial Intelligence: knowing which numbers actually predict your future, especially when everything around you is screaming that you're losing.

Watch the video. Bezos is calm. 

Not because he wasn't scared, but because he had clarity.

He knew exactly what was true inside his business.

That's how you survive what looks like a reversal, and come out the other side stronger.

That's how $6 becomes $1.7 trillion.

So here's my question for you:

What would it be worth to have that kind of clarity the next time everything feels like it's falling apart?

To know—not hope, not guess—that you're on the right track?

That's the game worth playing.

Check out comments for details

#founder #growth #ceo #scalingup

Helping Founders Break the $10M Ceiling | Strategy, Cash Flow & Leadership Systems | Scaling CFO

𝗙𝗿𝗼𝗺 𝗠𝗶𝗹𝗸𝗶𝗻𝗴 𝗦𝗵𝗲𝗲𝗽 𝘁𝗼 𝗠𝗶𝗹𝗸𝗶𝗻𝗴 𝗠𝗶𝗹𝗹𝗶𝗼𝗻𝘀.

Hamdi Ulukaya didn’t just build a yogurt brand, he redefined an industry.

No investors. No marketing budget. Just purpose, grit, and belief.

In 2005, he saw an ad.
An abandoned Kraft yogurt factory.

Everyone saw a money pit.
He saw possibility.

He didn’t have the money.
So he took a loan.

Bought the factory.
Kept 5 employees who believed when no one else did.

No income.
No sales.
No marketing.
Just faith, and a recipe from home.

Two years later, in 2007, Chobani was born.

No ads. Just bold packaging and pure taste.

Retailers hesitated.
But the people loved it.

Within 5 years, #1 yogurt in America.

Over $1B in sales.
The giants, Dannon, Yoplait, couldn’t catch up.

He stayed private.
Gave 10% of the company to his employees.

Hired refugees.
Put people before profit.

When asked why, he said:

👉 “Business is the strongest force for good, if it puts people first.”

From a shepherd in Turkey…
To a billionaire who still walks the factory floors.

Lesson?
You don’t need investors.
You need integrity.
You don’t need luck.
You need courage.

Because the dream still works, if you do.

Loved this story. Let me know your comments. 

What problem in your business keeps calling for your most creative energy?

#CEO  #FOUNDER #GROWTH #SCALINGUP

Two friends, Ben Cohen and Jerry Greenfield.

One dropped out.
One got rejected from med school.
But both wanted to build something.

First idea: bagels.
Too expensive.
So they pivot to ice cream.

No experience. No investors.
Just a $5 correspondence course from Penn State.
$2.50 each.

They find an abandoned gas station in Vermont.
Borrow $12,000.
Do the renovation themselves.

Ben can’t even taste properly, a condition called anosmia.
So he focuses on texture.
Big chunks. Wild swirls. Bold flavours.

What others saw as a weakness became their edge.

Within months, lines formed outside the door.
Free Cone Day became a tradition.
Word spread fast.

Few years later, they launched Cherry Garcia.
The brand took off across the country.
Soon, Ben & Jerry’s was making over $500M a year.

All from $12,000 and a $5 course.

Lesson?
You don’t need the perfect start.
You need creativity, courage, and the guts to turn constraints into leverage.

#scalingup #ceo #founder #growth

𝗠𝗼𝘀𝘁 𝗽𝗲𝗼𝗽𝗹𝗲 𝗻𝗲𝗲𝗱 𝗺𝗮𝗻𝗮𝗴𝗲𝗿𝘀.
𝗧𝗵𝗲 𝗯𝗲𝘀𝘁 𝗽𝗲𝗼𝗽𝗹𝗲 𝗱𝗼𝗻’𝘁.

Steve Jobs said it best, the greatest people are self-managing.

They don’t need direction. They are the direction.

When you’re scaling, this is the difference between speed and stagnation.

You can’t build a $10M company micromanaging every move.
You build it by surrounding yourself with people who:

➡️ See the problem before you do.
➡️ Fix it without asking.
➡️ Then tell you how they made it better.

That’s who scales companies.
Not followers.
Not “yes” people.
Builders.

If you have to keep pushing your team to move, 
you don’t have a scaling problem,
you have a people problem.

The truth?
The best teams don’t need managing.
They need mission.

Hire those who act like owners.
Give them the target.
Then get the hell out of their way.

That’s how you scale.
That’s how you win.

#scalingup #ceo #founder #growth

He built a dating site that generated exactly zero activity.
No users. No traction. No revenue.

Most leaders call that a failed model.
I call it an early audit.

Three ex-PayPal employees launched “Tune In Hook Up,” expecting market fit.
What they got was silence.
Operational cost? Rising.
User acquisition? Non-existent.
ROI? Negative from day one.

But here’s what mattered:
They reviewed the data instead of reacting to the emotion.

They noticed users trying to upload videos
Not for dating, but for everyday moments.
Unintended behaviour, but real demand.

So they executed the smartest financial move any early-stage team can make:
A low-cost pivot.

Same infrastructure.
Same upload system.
Zero additional burn.
Just a shift in positioning:
Share any video.

And that decision changed their entire valuation trajectory.

Users scaled exponentially.
Cost per acquisition plummeted.
Engagement skyrocketed.
Suddenly, they weren’t running a dating site…
They were running the internet’s first true video platform.

By 2006, their risk profile had flipped
High growth. High virality.
And high legal exposure.

Enter Google.
They offered $1.65B in stock for a business that still had no established monetisation engine.
From a financial lens?
That’s called derisking the future.

Chad Hurley, Steve Chen, and Jawed Karim accepted.
Smart move.
They transferred operational liability…
And secured generational wealth.

Today, YouTube contributes over $40B in yearly ad revenue
and sits at a valuation north of $500B.

All from a product that started as a complete miss 
until the data told a different story.

Lesson:
You don’t scale perfection.
You scale what the market proves it wants.
Listen to the numbers, not the narratives.
And never underestimate the ROI of a well-timed pivot.

#CFOInsights #Leadership #Strategy #Scalingup

He sold garbage bags at 12.
Not for fun.
To buy basketball shoes his parents couldn’t afford.

At 25, he was broke.
Sleeping on the floor.
Sharing a three-bedroom apartment with six guys.

Then one day, he got fired.
His boss told him
“You’re not cut out for this business.”

That hurt.
But instead of arguing,
He used the commission money from his last deal…
to start his own company.

MicroSolutions.
A small computer consulting business.
No degree. No investors. No fancy office.
Just pure hustle.

He made calls. Closed deals. Got rejected. Repeated.
Slowly, it worked.
Clients came in. Revenue grew.
Then, in 1990, he sold it for $6 million.

Most people would stop there.
Mark didn’t.

He bet everything on a new idea:
Streaming sports on the internet.
Way before the world was ready.

That company? Broadcast.com
In 1999, Yahoo bought it for $5.7 billion.
He became a billionaire overnight.

From selling garbage bags to selling a billion-dollar vision.
From sleeping on the floor to owning the floor on Shark Tank.

Mark Cuban didn’t just build companies.
He built proof, that hustle beats pedigree every single time.

Lesson:
You don’t need permission to start.
You don’t need approval to build.
You just need belief and the courage to act when no one bets on you.

#entrepreneurship #founders #startuplife #scalingup #markcuban #successstory

She sold her engagement ring for $10,000.
Ten years later, Vicky Tsai built a $500M skincare empire.

Most people call that crazy.
I call it commitment.

She walked away from a six-figure job…
Moved back into her childhood bedroom at 30…
Got rejected for 18 months straight…
And kept going anyway.

1,000 units.
Her last $5,000.
No safety net. No backup plan.

Month one? $2,000 in sales.
Most people quit here.
Vicky didn’t.

She packed every order by hand.
Wrote thank-you notes to strangers.
Built trust one customer at a time.

Then the internet found her.
Demand exploded.
Sephora called.
And the bedroom startup became one of the fastest-growing skincare brands in America.

In 2019, Unilever bought Tatcha for $500 million.
The $10,000 ring she sold?
It turned into 50,000x.

Lesson?
You don’t need permission.
You need conviction.
And the courage to burn Plan B. 

#ceo #founder #growth #scalingup

She was 20. A housewife. No experience. No degree.

Just a dream, and a recipe for chocolate chip cookies.

Everyone said it would fail.
“Cookies? That’s not a business.”

Banks said no.Experts laughed.

The market was ruled by Oreos and Chips Ahoy.

But Debbi Fields didn’t care.
She took a $50,000 loan with her husband.

Rented a small store in Palo Alto.

Rent: $800/month.
Failure wasn’t an option.

Opening day:
By noon, not a single sale.
She panicked. Grabbed a tray.
Walked outside.
“Try one. They’re free.”

That one line changed everything.
Crowds formed.

They sold out by evening.

She baked fresh every 2 hours.
Never sold day-old cookies.
If they sat too long, she gave them away.

Advisors hated it.
Customers LOVED it.

Year one: $200,000 in sales.
Then store #2.
Then San Francisco.
Then malls.
Then the world.

By the 1990s:

➡ 600+ stores
➡ $500M in annual sales
➡ And a new category: premium cookies

All from one woman who ignored logic and trusted her gut.

The takeaway:
If everyone says your idea is crazy,
you might just be onto something.

#scalingup #founder #growth #ceo

He got fired.
The company he built said, “We don’t need you anymore.”
Everyone forgot him.

But Steve Jobs didn’t stop.

He poured tens of millions into a failing company called Pixar.
Everyone thought he was crazy.
Most would have quit.

12 years later… that gamble sold for $7.4 BILLION.

Here’s the thing:

👉 He wasn’t chasing money. He was chasing vision.
👉 He embraced risk when others ran from it.
👉 He bet on what he believed in, even when the world said no.

Most people quit right before the payoff.
The real winners? They push through when it’s hardest.
They see opportunity where others see failure.

If you want massive results, you need to do what most won’t.
Step past comfort. Step past doubt. Step past fear.

Because the biggest payoffs live just beyond the point where almost everyone quits.

#scalingup  #growth #ceo

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Steve Jobs

He built pole barns to pay for college.

Decades later, John Menard Jr. built Menards, an $18B home improvement empire.

Most people call that luck.

I call it financial discipline.

He opened a small lumber yard in 1964…

Kept prices rock-bottom by building his own factories…

And built every store with cash, not debt.

No investors. No loans. No noise.

While others chased speed and Wall Street, John chose control.

He knew his margins by product line. He tracked cash flow like a pilot tracks altitude. He made the numbers his single source of truth.

Store by store. State by state. Slow, steady, unstoppable.

When 2008 hit, he didn't scramble; he expanded.

Today?

340+ Menards stores. $13B+ revenue. 3rd third-largest home-improvement chain in America. Still 100% private.

The lesson?

You don't need to grow fast. You need to grow right.

That means: 
→ Knowing your profit margins by service line 
→ Tracking cash flow weekly, not just at tax time 
→ Building systems so the business works, not just you

Financial clarity isn't about being a "numbers person."
It's about building simple, repeatable habits that let you scale with confidence.

Have the courage to own every decision, starting with your numbers.
#founder #growth #businessmindset #financialclarity #scalingup

Most people think success comes from working harder, dreaming bigger, or thinking smarter.

Here's the truth: none of that matters if you don't act.

In one simple test, a $50 bill was up for grabs. 

Everyone wanted it. 
Everyone talked about it. 
Everyone wished they had it…

Except Debbie.

She stood up. She walked forward. She took it.

That's it. 

That's the difference between winners and everyone else.

While everyone else burns time and money chasing online strategies that become less effective every day…

The smartest entrepreneurs thriving in 2025 are walking away from their screens and adding an extra 7-figures through live events.

Real humans. In-person communities. High-profit partnerships.

The ultimate advantage in the age of AI isn't replacing humanity with efficiency; it's experiences that are deep, connective, transformative, and profitable.

Getting face-to-face with your ideal clients AND peers is the most consistent solution to the Trust Recession.

I'll be at Event Profit Engine in Austin (December 10-12)...and I still have 4 discounted tickets.

If you're ready to get clarity on the financial blind spots keeping you from scaling, this is your moment.

Don't sit in the room wishing. 

Be Debbie.

P.S. Stop waiting for perfect timing. The money, the deal, the break… it's waiting for the first person who moves. Will it be you? DM me AUSTIN for ticket details.
#scalingup #CEO #founder #growth

Most founders don't fail because of competition.
 They fail because of the blind spots they never see coming.

Cash looks fine… until it doesn't. Revenue grows… but profit disappears. You hire fast… and spend months fixing mistakes. You work harder… but scale refuses to unlock.

I spent 20+ years at GE Capital navigating these exact challenges at a corporate level.

Closing an $800M+ power plant deal? That taught me cash flow precision. Managing international transactions? That revealed the profit leaks most miss. Building high-performance teams? That showed me the cost of hiring fast vs. hiring right.

Those frameworks didn't just help me lead deals—they gave me the blueprint for scalable growth.

Now I help founders apply these same battle-tested systems to their businesses.

The 7 blind spots in this carousel? They're the ones holding 90% of founders back from predictable, profitable scale.

If you want to go deeper… Download my free ebook in the comments. 

Fix the blind spots. Scale with clarity. Build a business that runs like a pro—because you learned from one.
#scalingup #founder #ceo #growth

7 Blind Spots

𝗛𝗲 𝗵𝗮𝗱 𝘁𝗵𝗲 𝗶𝗱𝗲𝗮.
𝗧𝗵𝗲𝘆 𝘁𝗼𝗼𝗸 𝘁𝗵𝗲 𝗽𝗼𝘄𝗲𝗿.

Most founders know Pinterest.

Almost no one knows Paul Sciarra, the guy who paid early salaries out of his own pocket, skipped taking income, and carried the company when no one else believed.

He wasn’t a “supporter.”
He was the architecture.

And then the quiet part of startup life happened.
Not a blow-up.
Not a fight.
Just… inches.

One meeting he wasn’t invited to.
One decision he didn’t have visibility into.
One board conversation that happened without him.

By the time Pinterest crossed millions of users and raised over $100M…
Paul was out.

He walked away with ~$15M.
Not nothing.
But painful when your original idea becomes a $25B enterprise.

This isn’t a story about betrayal.
It’s a story about leadership, governance, and identity.

𝗙𝗼𝘂𝗻𝗱𝗲𝗿𝘀 𝗱𝗼𝗻’𝘁 𝗹𝗼𝘀𝗲 𝘁𝗵𝗲𝗶𝗿 𝗰𝗼𝗺𝗽𝗮𝗻𝘆 𝗶𝗻 𝗮 𝗱𝗮𝘆.
They lose it when:
 • they stop owning the financial strategy
 • they delegate governance without understanding it
 • they avoid hard conversations
 • they let investors define the path
 • they disconnect from the role of architect

You can build something extraordinary…
and still get written out of your own success if you don’t stay in the seat you were meant to own.

𝗧𝗵𝗶𝘀 𝗶𝘀 𝘁𝗵𝗲 𝘀𝘁𝗮𝗴𝗲 𝗺𝗼𝘀𝘁 $𝟯𝗠–$𝟭𝟬𝗠 𝗳𝗼𝘂𝗻𝗱𝗲𝗿𝘀 𝗮𝗿𝗲 𝗶𝗻.
The product works.
The company has traction.
Teams are growing.

 But governance, capital strategy, and leadership identity aren’t keeping pace.
That’s the real risk.

𝗟𝗲𝘀𝘀𝗼𝗻:
Your idea can change the world,  but only if you stay in the role of architect as it scales.

Own your equity.
Protect your seat.
Upgrade your thinking.
Build with intention.
The threat isn’t being pushed out.
The threat is drifting out of your power.

𝗤𝘂𝗲𝘀𝘁𝗶𝗼𝗻:
 Are you building like the founder…
 or leading like the architect?

#ceo #founder #scalingup #growth

He was dropped at an orphanage at seven.
No food. No money. No choice.

By 14, he was on a factory floor, making metal frames.
One wrong move crushed part of his finger. Permanent injury.

Most people would quit. Most people would settle.
He didn’t.

He watched. He learned.
Every machine. Every process. Every decision.
Night classes. Every penny saved. Knowledge accumulation.

At 26, he opened a tiny eyewear shop in the Italian Alps.
Nothing fancy. No connections. Just him, a few employees, and an obsession with understanding the craft end-to-end.

Most competitors sold parts. He had a different idea: make complete frames. Control the product. Own the market.

By the 1980s, he was making designer frames for fashion houses.
By 1995, he bought LensCrafters—suddenly he controlled both the product and the retail.

Then came Ray-Ban.
Everyone said he overpaid $640 million for a dying brand.
He didn’t see risk. He saw opportunity.

Ray-Ban wasn’t just glasses anymore.
Movies. Celebrities. Fashion statements.
Value multiplied. Brand exploded.

He kept buying. Oakley. Sunglass Hut. Prada. Versace. Chanel. Pearle Vision.
Vertical integration? Check. Market dominance? Check. Monopoly? Almost.

When he died in 2022, Leonardo Del Vecchio had $25.8 billion.
One orphan. One factory worker. One relentless learner.

Lesson:
You don’t need luck. You need mastery, observation, and relentless execution.
Start small. Learn everything. Then own the ecosystem.

#ceo #scalingup #growth #founder

They emailed eBay 200 times.
eBay ignored every single one.
Most people would’ve given up.

But Marc, Oliver, and Alexander Samwer weren’t “most people.”

They cloned eBay.
Launched it in Germany.
Executed with speed and perfection.
Within months… eBay bought it back for $43 MILLION.

Then the brothers doubled down.
They built Rocket Internet, the company that turned cloning into a billion-dollar machine.

They copied.
They improved.
They scaled.
And they sold again, and again, and again.

Here’s the truth:

👉 They weren’t chasing approval, they were chasing execution at scale.
👉 They didn’t wait to be discovered, they created their own leverage.
👉 They mastered the one principle most founders overlook:
Doing it better beats doing it first.

Critics called them “copycats.”
But behind the noise, the Samwer brothers built an empire worth billions.

Most people stop when they hear “no.”
The one who succeed?
They push when it’s uncomfortable.
They build when others hesitate.
They turn rejection into momentum.

If you want outsized results, do what most won’t:
Step past comfort.
Step past doubt.
Step past fear.

Because the biggest payoffs live right beyond the point where almost everyone quits.

#scalingup #growth #ceo #bostonfounders

Mastermind Scaling Dinner 

This past Wednesday night in Boston, twelve leaders got uncomfortably honest about their real constraints.

No pitch decks. No surface-level networking. 

Just the Hero's Journey framework and one question: 

"What's actually stopping you from scaling?"

Three principles guided the conversation:

🪞 Your Business is a Mirror 

The bottleneck in your business is a reflection of a constraint in your leadership. 

Stop fixing symptoms. Fix the leader, and the business scales.

🐉 Constraints are Your Greatest Leverage

 Your biggest constraint is not a problem—it's the dragon guarding your next treasure. 

The right constraint, once identified and solved, unlocks massive, non-linear growth.

⚖️ Not All Success Has the Same Price

 You can build a company that breaks you, or one that fulfills you. 

Alignment + Clarity = Sustainable Success.

🎯 What showed up:

Estate planning. Cybersecurity. Medical devices. Food distribution. Banking. Fractional sales leadership. IT services. M&A law. Green infrastructure. Urban revitalization. Job search acceleration.

Different industries. Same truth: Every business grows until it hits a constraint, then grows no further.

The magic wasn't in solving everything in one night. 

It was in naming the real constraint out loud - not the sanitized version we tell at networking events, but the 2am version that keeps us up.

Some constraints were about capital. Others about people, partnerships, or positioning. A few were about letting go of what got them here to embrace what gets them there.

🤝 The vulnerability created immediate value: Real partnerships forming. 

Actual introductions being made. Problems being reframed. Resources being shared.

Thank you to Adrian Mendoza and the Mendoza Ventures team for hosting us.

And to everyone who showed up: Marco A. Schiavo , Geoffry Gilton, Joshua Sigsworth, PT, DPT, Dominic Endicott, Jacques Cohen, Maud Dentico, Vasant Narayan, Raffi Yardemian, CSL, Paul Smith, Alex Khalarian, and Sam "Butch" Nigro.

This is what happens when you build community around truth instead of transactions.

The Mastermind dinner happens monthly ( but we are taking a break in December). If you're a founder or executive in Boston or Greater Boston working on something real and willing to get honest about your constraints, let's talk.

We are going to start hosting Metro West dinners as well. More to come.

P.S. - Curious about finding the constraint for your business? Drop a comment or DM.

Most founders don’t fail because they’re lazy.
They fail because their goals are small.

Small goals keep you grinding.
Big goals force you to rebuild the system.

When you raise the target to 10x, everything changes:
your strategy, your thinking, your standards, your circle.

You stop playing in the crowded middle
and start operating where very few people dare to go.

10x isn’t harder.

It’s cleaner. 
It’s clearer. 
It’s smarter.

Stop playing safe. Start playing big.

I learned this lesson the hard way.

I wanted to grow my LinkedIn presence to 100K in a year.
I had 2k followers. 

A few people said that it would take years and that I was unrealistic.

Maybe they would have been right - if I'd believed them

I tried anyway. 
I took a course to learn from others who were ahead of me.
I showed up here every day.
Continuously improved my content (and my mindset)
Hired people to help me.

Did I accomplish my goal?
NO. 

I am still at 72k followers today, a year into that challenge.
But I am still grateful for the results. 

Can you imagine what would have happened if I had played small?
I may be at 15K followers at best. 

And that's the whole point. 

Even if you miss the 10X mark, it beats linear thinking. 

This same principle is why I help founders identify the 7 financial blind spots killing their scale - because small thinking about money keeps you grinding, while 10x financial clarity forces you to rebuild the system.

Want to apply 10x thinking to your finances? 

I've identified the 7 blind spots most founders miss. 

Download the guide; link is in the comments. 

#founder #ceo #growth #scalingup

10X Thinking = 10 X Results

He bought a bankrupt textile factory for $15 million.
Forty years later, Bernard Arnault built a $500B luxury empire.

Most people call that impossible.
I call it vision.

He didn’t invent anything.
He didn’t design a product.
He didn’t chase trends.
He just saw what others couldn’t.

Buried inside that dying company was a forgotten gem: Christian Dior.
Everyone overlooked it.
Arnault didn’t.

He sold everything except Dior.
Bet the house on one iconic brand.
And rebuilt from zero.

Then he made an even crazier move
He went after LVMH.
Louis Vuitton. Moët. Hennessy.
The crown jewels of French luxury.

The elite hated it.
The media mocked it.
It was the most hostile takeover France had ever seen.
Arnault didn’t blink.

He bought the shares quietly.
Took control boldly.
And turned LVMH into a global machine.

One acquisition at a time.
Fendi. Tiffany. Givenchy. Sephora.
Dozens of brands reborn under one ruthless strategy:

Let creators dream.
But keep the business razor sharp.

While tech giants chased disruption…
Arnault chased timelessness.

While others discounted…
He raised value.

In 2023, he became the richest man on Earth.
Quiet. Precise. Unshakeable.
He outplayed every tech titan without writing a single line of code.

Lesson?
You don’t need to invent.
You need to see the hidden gem
And have the courage to bet everything on it.

#entrepreneur #growth #businessstrategy #founder #scalingup

𝗛𝗲 𝗱𝗶𝗱𝗻’𝘁 𝗷𝘂𝘀𝘁 𝘁𝗮𝗸𝗲 𝗽𝗵𝗼𝘁𝗼𝘀.
𝗛𝗲 𝘁𝗼𝗼𝗸 𝗮 𝗽𝗿𝗼𝗯𝗹𝗲𝗺 𝗮𝗻𝗱 𝘁𝘂𝗿𝗻𝗲𝗱 𝗶𝘁 𝗶𝗻𝘁𝗼 𝗮 𝗯𝗶𝗹𝗹𝗶𝗼𝗻-𝗱𝗼𝗹𝗹𝗮𝗿 𝘀𝗼𝗹𝘂𝘁𝗶𝗼𝗻.

Back in the early 2000s, Jon Oringer wasn’t building empires, he was just trying to find affordable stock photos for his tiny online business.

But what he found instead… was an opportunity.

Stock images back then cost $300+ per photo, a luxury small creators couldn’t afford.

So Jon did something different:

▶ Bought a camera
▶ Took 100 photos a day
▶ Built his own website
▶ Uploaded 30,000 photos
▶ Charged $49/month for unlimited downloads

That’s how Shutterstock was born.

No fancy investors. No marketing team.

Just a subscription model, executed brilliantly.

He wasn’t selling images,
he was selling convenience, freedom, and access.

And the best part?

Every sale cost him nothing to reproduce.Pure passive income.

By the time Shutterstock went public in 2012,
Jon still owned 55% of it.

His net worth crossed $1 billion,
built from a camera, a simple website, and consistency.

That’s not luck.
That’s vision meeting execution.

Because the smartest entrepreneurs don’t wait for an opportunity,
they create it by solving a problem once
and selling the solution over and over again.

𝐋𝐞𝐬𝐬𝐨𝐧:

Stop chasing “new.”
Find one problem.

Solve it better than anyone else.
Then systemize, scale, and sleep while your solution works for you.

#Entrepreneurship #ceo #BusinessModel #founder #scalingup

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