Building Out

Owner

Founder

Heanton House Property

Property Investor

Urgent Care GP

NHS Appraiser

Portfolio GP

Macfarlane Wealth Partners

Partner

Royal Navy

General Practitioner

Doctor

As a doctor, former financial advisor, and property investor, I'm sharing the lessons I learned from being a busy, time-poor professional to building a life of time and financial freedom. 

My journey to financial freedom began with the standard advice of getting a great job, working hard, and hoping the system would take care of me.  After 20 years of service in the Royal Navy and as a doctor, I realised this was a myth.  This standard narrative will only take you so far, and I have started to seek better ways to build time and financial freedom for myself and my family. This realisation inspired me to share my journey and the lessons I've learned with you. 

My journey led me to earn my MBA, work as a financial adviser in London, and eventually transition into entrepreneurship. Investing in property and sharing financial lessons through our financial education start-up Building Out.  

I hope that sharing these lessons will help you on your path to Building Out a life of time and financial freedom.  The journey can be challenging, but it's certainly worth it!

Sign up for our free weekly newsletter at: 

www.building-out.com

Good luck on your journey!

Nothing on our website, blog, socials or newsletter is designed to provide financial advice and is for educational purposes only. For individual financial advice on your circumstance, please seek the advice of an FCA-approved advisor.

Diarmaid Mcmenamin

I asked 50 busy professionals what stops them from building wealth.
This is what they said: 

Nobody said "lack of money."

They said:

"I don't know where to start."

"It feels overwhelming."

"I'll figure it out later."

Translation: Comfort feels safer than action.

But here's the brutal truth:

Waiting for certainty is the most expensive strategy you can choose.

While you're "figuring it out," compound growth is working for someone else.

The move? One uncomfortable action:

→ Open the investment account

→ Schedule the financial review

→ Automate £100/month

Perfect clarity comes from movement, not meditation.

What's your one action this week?

As a doctor, former financial advisor, and property investor, I’m sharing the lessons on the path from being a busy, time-poor professional to building a life of time and financial freedom.

I ran the numbers on lump sum investing and the truth is uncomfortable.

Here's what the research actually shows.

Lump sum beats Dollar cost averaging (DCA) most of the time – not all the time, but most. If your goal is maximum long-term returns and you can handle the roller coaster, getting invested sooner usually wins.

Why? Cash drag reduces your compound growth. Performance matters more than perfect timing. Every month, waiting costs you potential returns.

So why is everyone still doing DCA?

Because the real risk in investing isn't volatility. It's you freaking out and doing something stupid. DCA shines in that anxious window right after you decide to invest. It keeps you from panic-selling when fear takes over.

Bottom line: Pick the strategy you'll actually stick with when markets drop 20%.

Want more straight-talking money systems? Join the newsletter at www.building-out.com

Motivation is a terrible business partner.

It shows up late.

Leaves early.

Disappears when things get hard.

But consistency?

Consistency is the reliable partner that builds wealth.

Think about it:

→ £100/month invested consistently = £60K in 20 years

→ £0/month invested when "motivated" = £0

→ One property viewed weekly = 52 opportunities/year

→ Property viewing only when "ready" = 2-3 opportunities/year

→ Daily 30-min skill building = 182 hours/year

→ Learning only when "inspired" = maybe 20 hours/year

The professionals achieving time and financial freedom aren't the most talented.

They're the most consistent.

What system can you commit to regardless of how you feel?

You don't need to be perfect with money. Just intentional.
Here's how: 

Pick a system, tweak it to fit your life, and ignore the rest.

Start with 50/30/20 if you need structure.

Add values-based habits as you grow.

Combine the two for long-term clarity.

You don't have to choose a side. You just have to choose you.

Your budget doesn't need to impress anyone. Just work for you.

I spent 6 months researching UK founders who built life-changing businesses. Here's what the data actually shows:

What I found completely shattered my assumptions about "the right time" to start. 

The myth we believe:

Founders are either brilliant 22-year-olds or wealthy 45-year-old executives with safety nets.

The reality:

- Tech founders average 30
- Fintech founders: late 20s-early 30s
- Healthcare founders: early 40s-mid 50s

Ben Francis started Gymshark at 19, delivering pizzas.

Anne Boden launched Starling Bank at 54.

Ali Parsa built Babylon in his 40s as a former refugee.

The pattern?

None of them waited to feel ready. They started with what they had, where they were.

If you're thinking "I'd love to build something but..." — you're already past the starting line. Most people never even get to the thinking stage.

The only barrier isn't your age, your job, or your circumstances.

It's waiting.

What's one small action you could take this week toward building the life you want?
What I found completely shattered my assumptions about "the right time" to start.

Here's what the data actually shows:

The myth we believe:

Founders are either brilliant 22-year-olds or wealthy 45-year-old executives with safety nets.

The reality:

- Tech founders average 30
- Fintech founders: late 20s-early 30s
- Healthcare founders: early 40s-mid 50s

Ben Francis started Gymshark at 19, delivering pizzas.

Anne Boden launched Starling Bank at 54.

Ali Parsa built Babylon in his 40s as a former refugee.

The pattern?

None of them waited to feel ready. They started with what they had, where they were.

If you're thinking "I'd love to build something but..." — you're already past the starting line. Most people never even get to the thinking stage.

The only barrier isn't your age, your job, or your circumstances.

It's waiting.

What's one small action you could take this week toward building the life you want?

You send an important email to a potential clientand get no response:


Three days pass. No response.

Your brain immediately fills in the blanks:

They're not interested.

They think my price is too high.

They found someone better.

I blew it.

You feel defeated. You don't follow up. You move on, convinced it's a lost cause.

Two weeks later, they email apologizing. They'd been traveling with spotty internet. They want to move forward.

How much anxiety did you create for yourself by assuming you knew what they were thinking?

This is what Ruiz calls the third agreement: Don't make assumptions.

We're all guilty of this. We assume we know what people are thinking. We assume we know why they did what they did. We assume we know how things will turn out.

Most of the time, we're wrong.

And here's the kicker: our brains are wired for negativity bias. When we don't have information, we tend to assume the worst.

This is catastrophic when you're trying to build wealth.

You assume you're not qualified for that opportunity, so you don't apply.

You assume your prices are too high, so you don't charge what you're worth.

You assume your partner will be upset if you invest money in yourself, so you don't have the conversation.

All these assumptions become self-fulfilling prophecies. Not because they were true, but because you never tested them.

Here's what this looks like in practice:

You're unclear about a client's expectations. Instead of assuming you know what they want (and potentially delivering the wrong thing), you ask clarifying questions. You confirm. You get on the same page.

You catch yourself thinking, "I could never earn six figures doing what I love." That's an assumption. You don't actually know that. So you research. You talk to people who've done it. You test the waters.

The result? You start living in reality instead of in the anxiety-inducing stories your brain creates.

Stop making assumptions. Start asking questions. Start seeking clarity. Start testing your theories.

You might discover your assumptions were completely wrong.

What assumption are you operating under right now that you haven't actually tested?

The question everyone asks is "Dollar Cost Averaging (DCA) or lump sum?" but that's the wrong question.

Here's what you should actually be asking.

The real question is: "Which strategy will I actually follow?"

I've seen both approaches work brilliantly. I've seen both fail spectacularly. The difference? Not the strategy. The person.

Lump sum wins when you have strong emotional discipline, can ignore 20% drops, are optimising for expected returns, and won't check prices daily.

DCA wins when you're building an investing habit; you'd freeze without a process. Peace of mind has real value, and you're actually new to this.

But here's what always loses: Waiting for the perfect moment, sitting in cash for years, letting fear make your decisions, never starting at all.

Pick one. Commit to it. Stop second-guessing. Then build the life that money is supposed to enable.

Because here's the real secret: The difference between DCA and lump sum over 20 years is noise compared to the difference between investing and not investing.

What's stopping you from starting? Build wealth without it taking over your life: [www.building-out.com](https://lnkd.in/ePYPd5tB)

I spent 15 years building a successful medical career while dreaming of freedom. Then I read about the Crystal Merchant and realised I was making his exact mistake.

In The Alchemist, there's a character who dreams of a pilgrimage to Mecca his entire life. He talks about it constantly. Plans it meticulously. But he never goes.

Why? Because as long as it remains a dream, he doesn't have to face reality.

Here's what I see with busy professionals constantly:

- Dreaming of starting a business but never taking action
- Planning property investments but never making an offer
- Talking about freedom but never leaving the secure job

The hard truth? As long as your freedom remains a comfortable dream, you'll never face the risk of actually building it.

Achieving time and financial freedom requires action, not just aspiration.

What dream have you been protecting by not pursuing?

When I work with professionals who want financial freedom, there's this myth that you need to make a dramatic leap — quit the job, go all in, burn the boats.

Sometimes. But usually? You need a smarter approach:

The Three-Step Freedom Build:

1. Keep your day job (your foundation)
2. Build your freedom engines (property, business, investments)
3. Transition when ready (move forward stronger)

This approach gives you:

- Capital for the next phase
- Skills you didn't have before
- Confidence in unfamiliar territory
- Proof you can succeed

My property portfolio was built exactly this way. NHS shifts funded the deposits. Financial advisory knowledge guided the investments. Small, consistent action while maintaining income.

Not dramatic. Not Instagram-worthy. But effective.

Stop waiting for the perfect moment to leap. Start building your freedom engines right now, even if it's just 10 hours a week.

I used to wait for perfection before sharing anything.

Here's what that perfectionism cost me:

→ 6 months building in silence

→ Zero feedback until launch

→ A product nobody wanted

→ Complete restart required

The shift that changed everything:

I started sharing before I was ready.

Messy first drafts. Half-baked ideas. "I don't know what I'm doing" moments.

The result?

Real-time feedback. Course corrections. Community validation. Faster iteration.

The lesson:

Consistency over perfection. Always.

3 ways to start before you're ready

1. Share your outline before writing the content
2. Post your framework while it's still rough
3. Announce your goal before you have the full plan

Your audience would rather see regular, authentic updates than wait for the "perfect" post that never comes.

Perfection is procrastination in disguise.

Movement beats meditation.

Do you have an idea for a business but don't know how to pitch it? Here's one way to be unforgettable!

I speak to people about building a life of time and financial freedom and hear the same excuses: not enough time, not enough money, and it's too late 

Open article: How To Be Unforgettable When Pitching Your Business by Diarmaid Mcmenamin • 5 min read

How To Be Unforgettable When Pitching Your Business

People rarely buy on logic alone.
They buy:

- Belonging
- Identity
- Story
- Emotion

Your product is just the vehicle. The feeling is what people are really buying.

Think about the brands you're loyal to. Is it really because their features are 10% better than the competition?

Or is it because of how they make you feel? What being associated with them says about you?

The coffee shop that makes you feel like part of a community. The tech brand that makes you feel innovative. The car that makes you feel successful.

That's what drives purchase decisions.

Features tell. Feelings sell.

When you're building your business, ask yourself: What emotion do I want people to feel when they use this? What identity does choosing my product reinforce for them?

Because if you only compete on features and price, you're in a race to the bottom.

But if you compete on meaning? You build loyalty that transcends logic.

People will pay more, wait longer, and defend you fiercely—not because you're objectively better, but because of what you represent to them.

What feeling does your product or service create? And are you leading with that in your messaging?

I used to treat money like a checklist.
Here’s the problem with that:

Pay bills. ✓

Save money. ✓

Don't go into debt. ✓

Joyless. Mechanical. Something to get through rather than feel good about.

Then I started tracking micro-wins, and progress became genuinely motivating:

Cleared that lingering credit card? Acknowledged it.

Emergency fund hit three months of expenses? Celebrated it.

Increased pension contribution by 1%? Marked it.

These aren't life-changing amounts. They're small victories that prove the system works.

But here's what I'd missed for years: discipline without rewards is just punishment.

If your financial journey is all restriction and zero celebration, you'll eventually rebel against your own system.

The brain needs evidence that effort leads to progress. It needs dopamine hits from wins, not just the absence of losses.

Behavioural psychology is clear on this: what gets celebrated gets repeated.

So I keep a simple list. Nothing fancy. Just a note in my phone where I log financial wins. Small ones count. Consistency counts. Progress counts.

Looking back at that list after six months is surprisingly powerful. You see accumulation. You see momentum. You see proof that the boring, daily decisions add up to meaningful change.

This isn't about being materialistic or obsessing over money. It's about acknowledging progress in an area of life that's easy to take for granted until something goes wrong.

Most people only notice their finances when there's a problem. But what if you trained yourself to notice when things are working?

What's one financial win from the past year that you haven't stopped to appreciate?

Maybe it's time to mark it, even briefly. Progress deserves acknowledgment.

Even when I was earning well, I felt guilty spending on myself.
Here's why:

That dinner out? Should probably cook at home.

Those concert tickets? Maybe save the money instead.

New running shoes when my old ones still work? Feels frivolous.

Every purchase came with a side of anxiety: "Should I be saving this? What if I need this money later?"

The irony? I could afford all of it comfortably. The problem wasn't my finances—it was my psychology.

Then I set up a separate "Spending" account. 60% of my income, allocated purely for living and enjoying life.

Same salary. Same expenses. Completely different mental framework.

Here's what shifted: the decision was made before the money even hit my main account.

If it's in the Spending account, I have permission to spend it. No guilt. No second-guessing. No mental gymnastics.

Want to upgrade my coffee? It's allocated spending.

Grab dinner with friends spontaneously? Allocated spending.

Book a weekend trip? Allocated spending.

Meanwhile, my emergency fund and long-term investments were automatically being topped up from separate accounts. Future me was taken care of without current me having to sacrifice enjoyment.

This isn't about reckless spending. It's about intentional enjoyment within a structure that protects your future.

Guilt-free spending isn't irresponsible. It's a feature of a well-designed system.

The alternative—constant anxiety about every purchase—is exhausting. That mental taxation probably costs more than any financial mistake you could make.

If your financial plan doesn't allow for joy, you won't stick to it long-term. Discipline without rewards is just punishment.

What would your guilt-free fund go toward? And more importantly, what's stopping you from setting one up?

You're successful in your career, but feeling trapped.
Here’s what to do: 

You dream about building something of your own. But every time you think about starting, a voice says: "It's too late. You should have started at 25."

Here's what that voice doesn't tell you:

Anne Boden was 54 when she launched Starling Bank.

Not 25. Not 35. Fifty-four.

After decades in traditional banking, she saw what needed to change. The industry laughed. She kept building anyway.

Today, Starling has millions of customers and has reshaped UK banking.

The truth nobody mentions:

Your years of experience aren't wasted time.

They're your unfair advantage.

You've seen the problems.

You've built the skills.

You understand the market.

The 25-year-old doesn't have that.

So here's my challenge:

Stop treating your age as a liability.

Start treating your experience as ammunition.

What problem have you been watching for years that you're finally ready to solve?

Most people judge their finances by their bank balance.

Here’s the problem with that: 

"Do we have enough to get to Friday?"

"Can we cover the holiday?"

"Will this month break us?"

But that's like judging your health by whether you had a salad once this week.

Here's what they miss:

A bank balance tells you what's happening today.

Net worth tells you what's happening overall.

The Truth:

→ You can feel good in your bank account and still be falling behind

→ You can feel stretched in your bank account and still be building real wealth

Only one number reveals the truth.

The Shift:

When I first calculated my net worth, everything clicked.

I stopped focusing on survival.

I started focusing on growth.

I became obsessed with the gap between income and expenses—the space that gives you freedom to invest, create, and build.

What tracking gives you:

- A reality check (no more self-delusion)
- Early warning signs
- Motivation from measurable progress
- Calm (because you know where you stand)

One review won't change your life overnight.

But it will change the way you think.

And that shift leads to better choices, clearer priorities, and more peace of mind.

Learn more at [www.building-out.com](https://lnkd.in/ePYPd5tB)

Most people think wealth requires a big income.
Here's the truth:

I used to think that too.

Then I met people earning £200K who were broke.

And people earning £50K who were building real wealth.

The difference?

Discipline beats income every single time.

You don't need more money.

You need better systems

What does the autumn budget mean for you? Here are some traps to avoid......

Most of the people reading this blog are well-paid, busy, time-poor professionals who aspire to a life of time and financial freedom. While it's impos

Open article: Autumn Budget 2025: 3 Tax Moves Every £100k+ Earner Should Make Now by Diarmaid Mcmenamin • 10 min read

Autumn Budget 2025: 3 Tax Moves Every £100k+ Earner Should Make Now

Most entrepreneurs don't go broke because their business failed.

They go broke because of one signature.

Here's what I mean:

You set up a limited company.

You think you're protected.

Then a landlord asks you to personally guarantee a loan.

You sign it because you need the deal.

One signature.

That's all it takes to bypass every liability protection your company gave you.

The business sinks?

You sink with it.

I've watched smart people lose their homes over this.

The fix is simple:

→ Refuse personal guarantees unless absolutely necessary

→ Keep business and personal finances completely separate

→ Build a firewall before you need one

Protect your downside before you chase upside.

Here's the problem with some traditional financial advice:

It assumes you're a robot.

"Mathematically, you should invest instead of paying off your mortgage."

But humans don't operate on spreadsheets.

We operate on:

→ Fear when markets crash 40%

→ Panic when redundancies hit our sector

→ Stress when family needs support

The "right" move on paper becomes impossible to execute in reality.

That's why the best financial strategy isn't the one with the highest return.

It's the one you can actually stick to when everything goes wrong.

Because life tests your plan exactly when you're least able to handle it.

Smart finance isn't about optimisation.

It's about durability.

Can your strategy survive reality?

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

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

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

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

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

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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

Passion isn’t happiness.
It’s pain.
It’s grinding when no one is watching.
It’s suffering through every mistake, every rejection, every late night, just to build something nobody thought was possible.

Jensen Huang didn’t follow the market.
He didn’t wait for AI to be big.
He invested 10,000 engineer-years ahead of demand.
He pivoted Nvidia from graphics chips to AI dominance.
That’s vision. That’s first-principles thinking. That’s suffering smarter than everyone else.

Breakthroughs aren’t born in comfort zones.
They’re born when you refuse to quit, when you embrace the grind, and when you’re willing to suffer today for what the world will celebrate tomorrow.

Extraordinary isn’t given.
It’s earned.
Through struggle.
Through relentless work.
Through being willing to do what everyone else won’t.

If you want to be great, get comfortable being uncomfortable.

#scalingup #growth #ceo #founder

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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