27+ Years Helping Lawyers Build for Life After Law — Without Sacrificing Today | Clarity • Intention • Legacy | Founder, The Wealthy Lawyer

LET’S BE HONEST.
Law school likely didn’t teach you much about personal finance.

But then you’re thrust into a demanding career — often with a ton of student debt — and suddenly you have a second job:
👉 Managing your money.

Whether you're in your first year of practice or a senior partner, you’re busy building your practice and keeping clients happy.

That leaves little time (or energy) for the things you actually enjoy — time with family, travel, hobbies… let alone planning for your financial future.

And honestly?

Most of the lawyers I speak with have spent more time planning their next vacation than protecting the lifestyle they've worked so hard to build.


That’s where we come in.

Using our Wealthy Lawyer™ Program, we take the guesswork out of financial planning.

We help you:
✅ Protect your family and income from the unexpected
✅ Build wealth intentionally
✅ Prepare for Life After Law


Our clients typically reach out when they:

• Are worried about how their family would cope if they couldn’t work
• Don’t know whether to save or pay down debt
• Feel behind, despite earning well
• Know they need a plan — but don’t know where to start
• Realize they can’t do it all alone — and want trusted guidance


What they’re tired of:

• Being the sole/primary income earner without a backup plan
• Wondering if they’d need to change their lifestyle if a family member got sick
• Stressing about whether they’re saving enough for retirement
• Not knowing how to leave a legacy for their kids or grandkids


After just a few months in the Wealthy Lawyer process, our clients tell us they feel more:

✅ Confident about hitting their financial and lifestyle goals
✅ Prepared to face unexpected life events
✅ Assured that their spouse and family won’t be financially stressed
✅ Clear about the legacy they’re leaving behind


You’re in the business of law — not financial planning.
Let us take the worry off your plate so you can focus on what matters most…

Like that next vacation.

📩 Ready to take control of your financial future?
Let’s connect for a Virtual Coffee Chat —  no pressure, just a conversation

Jeffery M. Lamont

Life hack:

Build a life with a partner who, even if you were both exhausted and broke, you’d still want beside you on the couch eating takeout.


👉 What is the last movie you and your partner in crime watched on a night in?


────
I’m Jeffery, the advisor who helps lawyers build a financial life that supports the moments (and the people) that matter most.

Helping Lawyers Build for Life After Law — Without Sacrificing Today | Founder, The Wealthy Lawyer

Most people think they don’t need insurance…
until life proves them wrong.

That's what I thought at 23.

Six weeks in a hospital changed that.

I’d just come back from playing pro baseball in Europe.
Best shape of my life.

Nothing could touch me…
or so I thought.

Then I got seriously ill.
Six weeks hospitalized.
Three months off work.

It was a wake-up call I never expected.

And it taught me something I’ll never forget:

Life is unpredictable.
And when things flip, they flip fast.

So here’s the real question:

If something unexpected happened tomorrow, do you have a plan to protect yourself and the people who rely on you?

Here’s the blind spot most people never see until it’s too late:
insurance isn’t about fear...
it’s about keeping your life stable when everything else feels shaky.

Here are three ways it does that:

➡️ Life Insurance:
Gives your loved ones financial stability — mortgages, debts, daily expenses covered.

➡️ Disability Insurance:
Replaces your income so your lifestyle doesn’t have to change if you can’t work.

➡️ Critical Illness Insurance:
Provides a lump sum so you can cover medical costs and focus on recovery, not money.

The best time to get insurance?
It’s when you’re young and healthy.

It’s more affordable…
and it guarantees you’re protected no matter what life throws at you.

Don’t wait for a wake-up call like I did.
 
👉 What’s one thing you thought was unnecessary when you were younger that makes a lot more sense now?

Share below 👇
 
────
I’m Jeffery, the wealth advisor who helps lawyers build, protect, and transition their wealth.

☕ If you ever want to talk through your options, I’m always happy to grab a quick virtual coffee.

No pressure. No pitch. Just clarity.

Three years ago, I started on LinkedIn…

And three years ago, I was ready to quit…

I was posting Googleable facts.
Zero personality.
Generic advice.
Safe takes.

And it showed.

That was, until I met Holly Crawshaw Joyner
She called me out…
then helped me find MY voice.

That was a little over year ago.

Since then, things shifted in a way I never expected.
Here’s the difference: 2023 vs 2025 (to date).

📈 Impressions: 100K → 2.2 Million
📈 Engagement rate: 1.1% → 5.1%
📈 Comments: 125 → 16,600

This year I’ve had 6 posts get more impressions — individually — than all of 2023.

But the numbers aren’t the part I’m most proud of.

It’s this:

→ People messaging me saying “It felt like you were talking directly to me.”
→ Real conversations with lawyers and professionals who feel seen — not sold to.
→ And the part I never saw coming: actual friendships with people in parts of the world I never imagined I’d be connected to.

If you’d told me three years ago that LinkedIn would introduce me to people I genuinely care about — mentors, peers, friends — I probably would’ve laughed.

But it has.
And it’s one of the best parts of this whole thing.

This reality is, this stopped being “marketing” a long time ago.
Now, it’s turned into a mission.

A mission to help people build wealth with more clarity…
less noise…
less shame…
and a whole lot less stress.

If you’ve been reading, commenting, DM’ing, supporting, or even just quietly lurking…
thank you 🙏

You helped me turn something small and uncertain
into something meaningful.

And if you’re still in the early stages of your own thing?
Stay with it.

Most good things don’t look good at the beginning.
But they become good because you stayed.


 👉 what’s one surprise you’ve experienced as a result of being on LinkedIn?


────
I’m Jeffery. I help professionals build wealth intentionally so they can live with more freedom and peace.

If you want more clarity heading into 2026, let’s grab a Virtual Coffee ☕

Find the “Become a Wealthy Lawyer” link in my profile.

I write your LinkedIn™ posts + your books || Top 20 LinkedIn™ Expert [Favikon, 2025] || New York Times + USA Today Bestseller

The real flex isn’t making $1M a year.

It’s making $1M a year without:

→ Missing every family milestone
→ Sacrificing your health
→ Living life on autopilot

That’s the real flex.

Jeffery M Lamont

I thought I understood gratitude… until one day changed everything.

As we head into American Thanksgiving, I’ve been thinking about what gratitude actually is.

It’s not comfort.
It’s not ease.
It’s not the good years.

It’s perspective.

I didn’t understand that until 2019.

That was the year I lost my mom
and our house flooded
on the very same day.

One morning changed everything.
And it marked the start of one of the hardest chapters of my life.

But it’s incredible what living in a hotel with your wife, three kids, and a dog will teach you.

In the middle of the chaos, I found myself grateful
not for what was happening… but for what I still had.
My family.
Our safety.
And the lessons my mom left behind.

That’s when it finally clicked:

Gratitude isn’t a reaction to things going right.
It’s the anchor that gets you through what isn’t.

So today, I’m grateful for:

• Quiet mornings with Colleen and the kids (even if the house is a little quieter these days)
• Family, baseball, and the memories that outlast the seasons
• Clients who trust me to help them simplify and protect what they’ve built
• And this community — the conversations, connection, and support

Thanksgiving is a time to hit the pause button.
A moment to look around and realize that even in the mess…
there’s still so much to be thankful for.

From my family to all my American friends — Happy Thanksgiving.


🦃Who or what are you grateful for this week — even if life isn’t perfect right now?


📸 Our family’s tradition of writing what we’re grateful for on pumpkins. I’ve included a photo with one of my mom’s final inscriptions.

Simple. Honest. Lasting.

You earn $330,000 and still feel broke.  Here's why...


Meet a client of mine who faced this exact challenge.

→ 34
→ newly engaged
→ student debt finally paid off
→ $285k annual salary
→ $45k-ish annual bonus

Despite his earnings, he was struggling to plan for his future.

He had three main goals:

 1. Save for the wedding
 2. Buy their first home
 3. Retire early-ish

Here's the kicker:

His bonus isn't always guaranteed.

That uncertainty made long-term financial decisions more difficult to make and brought anxiety to him.

 When he came to us, he had:

 → $14,000 in his savings account
 → $27,000 in his TFSA
 → $42,000 in his RRSP

I'd call this a good start for where he's at, but he felt unsure how to manage his finances most effectively each year.

For further context…

He's finding practicing law to be a grind.

Despite being a high performer, the demanding nature of BigLaw has made early retirement a goal of his.


 Here’s what we did:

 → Covered him and his (soon to be) fiancée with the proper insurances in case something happens to him.

 → Created a financial plan to make his bonus work for him, treating it as the game-changer it is when/if it comes next Feb.

→ Implement a cash flow management system that will help ensure he lives comfortably on his salary alone.

→ While not expected to pay for it all, he and his fiancée want to contribute to the wedding, so we upped their short-term savings

→ We've set up FHSA accounts for his fiancée and him so they can take advantage of that opportunity.

The result?

→ As they prepare to start their new life together, both he and his fiancée have peace of mind with the various insurances (life and Critical Illness) we put in place.

→ He feels much more comfortable with his month-to-month cash flow

→ They will have enough saved for what they feel should be their share of the wedding annnnnnd a down-payment on a condo.

→ His retirement plan projects he can retire by 58 (provided he maintains his savings percentages)

We’re little more than a year into his journey with us.

He's told me he already feels more in control and less anxious about his financial future.

Hearing the relief in his voice when we chat is priceless.

It's incredible what a customized financial plan, and his taking action, can do.

No more sleepless nights worrying about where his money is going.

Instead, he now has a clear path to achieving the life he desires.



👉If your money could talk, what do you think it would say about you?👇


────
I'm Jeffery, the wealth advisor helping lawyers take control of their finances and achieve their biggest goals.

🔗 Let’s connect for a Virtual Coffee Chat ☕️ to create a clear path toward your financial future—no more sleepless nights, just a plan that works.

No pitch.  No pressure.  Just clarity

If you feel behind at 41, you’re in good company...

Your income rises quietly…
and then, your lifestyle outruns intention even faster.

On my way home from the F1 in Austin a few weeks ago, I ended up in one of those easy airport conversations that starts as small talk… 
then goes a little deeper than you expect.

I was in the lounge half-working when the guy next to me noticed my F1 bag and said he was there for the race too.

We did the usual recap:
the heat, the crowds, the traffic.

He said he was heading home to NYC.
I said I was making my way back to Toronto.

Then he asked what I did.

I gave him the short version:
I help lawyers simplify their financial lives so money feels less chaotic and more intentional.

He nodded and said:

“Well… I practice at [he named a Top100 firm.]”

That opened the door.

We talked about the pace of practice, the hours, the pressure…
and how hard it is to juggle time and money when both feel scarce.

Then he hit me with something I wasn't expecting:

“This is my first full year as an Equity Partner. Still not making a ton yet, but definitely more than I ever thought I’d be making at 41.”

He paused, then admitted:

“And the worst part is… I still can’t get ahead. I thought by now I would be. But I'm not.”

No blown-out budget.
No crisis.

Just the quiet lifestyle upgrades that sneak in when income rises:

• a nicer hotel
• a faster flight home
• Paddock tickets because “why not?”
• and a handful of conveniences that feel harmless in the moment…

But they add up fast.

Then he said the line most lawyers eventually reach:

“I don’t think mine is a money issue…"

And he’s probably right.

Most lawyers don’t run out of money.
They just let lifestyle outrun the planning that’s supposed to support it.

Which is why tomorrow’s 1% Shift is all about timing…
and the tiny change that helps you finally feel ahead before life expands — not after.

More tomorrow.

☕ If you’ve ever hit that “I’m earning more… so why doesn’t it feel like it?” moment, let’s grab a Virtual Coffee.

You’re not the only one — and clarity comes fast once you have a structure.

Most lawyers don’t run out of money…
They just let their lifestyle outrun their structure.

And a conversation I had recently brought it right back into focus.

The partner I met wasn’t being reckless.
No blown-out budget.
No splurges.
No crisis.

Just the same quiet drift I see every single week:

A nicer hotel.
A quicker flight home.
Paddock tickets because “we might as well.”
Conveniences that feel harmless in the moment… and heavy later.

Then he said the line almost every lawyer eventually reaches:

“I’m earning more than I ever imagined…
but I still can’t get ahead. I thought by now I would be. But I’m not.”

And he said it quietly...
the way people talk when they’re tired of carrying it.

Here’s where most people get it wrong:

It’s not a money issue.
It’s a timing issue.

He wasn’t saving too little.
He was saving what was left after living life the way he wanted.
And that will always feel like you’re chasing something that keeps moving.

Savings before lifestyle?
That’s when things finally flip in your favour.

THE 1% SHIFT FOR TODAY

Set up one automatic transfer (15–20% of your net pay) that leaves your account the same day you get paid.

Put it in a TFSA, your RRSP, or a non-registered account
It doesn’t really matter.
The magic is in the automation.

When your money has a job,
your stress drops,
your decisions get cleaner,
and your lifestyle stops silently stealing your progress.

Tiny shift.
HUGE difference.

If you’ve ever asked yourself why you’re not ahead yet…
you’re not alone.

If you want the exact setup I walk clients through,
DM SHIFT.

No pitch.  No pressure.  Just clarity — and the feeling of finally getting ahead again.

Some weeks don’t hit you until Sunday night...

Not because anything dramatic happened.

But because you spent a week managing work, family, pressure, expectations…
and all the little things no one notices unless they’re the ones carrying them.

By the time Sunday night rolls around, the weight finally shows up.

If that’s you tonight, you’re not alone.

Here’s what I remind myself before a new week starts:

Most of us underestimate how much we're carrying…
until we stop long enough to feel it.

Progress rarely feels fast.
Most of the time it’s quiet, steady… almost unremarkable.

And here’s the part we forget:
Those quiet days —
the ones where you just keep showing up —
they’re the ones that move you forward.

Take the quiet win.
You handled more than you realize…
and you’re still here.

Let tonight be the reset.
Not the end of a long week...
but the chance to set yourself up for an even stronger one.


How do I get myself ready?
I keep it simple:

Three “result priorities” — the three things that, if I do nothing else, will make it a great week.

Three “activity priorities” — the actions that help me hit those results and move me toward my year-end goals.

Six lines.
Ten minutes.
A calmer Monday.

Tomorrow’s yours to set the tone.

Walk into it with clarity, conviction,
and a refueled tank, ready to win the week.


👉 What is one thing you want to accomplish this week to make it a real winner?


If financial clarity is something you want more of as we head into 2026, grab a quick Virtual Coffee using the link in my profile.

Protect your income first…
Everything else depends on it

If you read my post from yesterday,
you saw how quickly life can flip…
and how painful it is to discover you’re underinsured at a time you need it most.

Every lawyer wants to build wealth…
but almost no one starts by protecting the thing all else depends on:

Your ability to earn an income.

If that stops, everything downstream gets shaky fast.

And the cracks usually show up in the same places:

• Group disability that barely covers half the lifestyle
• No critical illness plan
• Life insurance that was “temporary”… a decade ago
• Partners assuming success = invincibility

Here’s your 1% Shift for today:

→ Action: Review your insurance — or ask an advisor to run a quick Insurance Audit.

That’s it.

One audit.
One hour.
Massive clarity.

You’ll know what’s locked in…
and what needs attention before life forces your hand.


💭 When did you buy your first insurance policy?


If you want a quick check-up,
DM “Audit” and I’ll walk you through it.


No pitch.  No pressure.  Just clarity.

There’s a moment I see all the time with lawyers.

It usually happens right after we walk through the numbers...
the real ones.

They exhale.
Their voice softens.
Their shoulders drop.

And they say some version of:

“I didn’t realize how much this was weighing on me.”

Not the savings.
Not the insurance.
Not the tax structure.

The uncertainty.

I saw it again this summer.

A 41-year-old partner I first had a Coffee Chat with a couple years ago.
Back then, he was DIY’ing through a robo-advisor and felt he was “doing fine.”

Then July hit.
And suddenly “fine” wasn’t fine anymore.

Cash flow felt tighter.
Taxes were starting to mount.
And the gap between what he thought he had and what he actually had started to widen.

That’s usually when clarity becomes non-negotiable.

Because optimism works…
until it suddenly doesn’t.

And when you replace,
“I hope everything is fine”
with
“I know exactly where I stand,”
something shifts.

The noise quiets.
The pressure eases.
You make decisions faster.
Your family feels more stable.
You feel a lot more like yourself.

That’s the real benefit of clarity.
Not the spreadsheets.
Not the projections.
Not the policies.

It’s the calm that shows up once you stop relying on hope...
and start relying on structure.

────
I’m Jeffery, the advisor lawyers call when “doing fine” stops feeling fine.

If you want the same kind of calm and clarity...
find the Become a Wealthy Lawyer link in my profile and let's sit talk.

No pressure.  No pitch.  Just clarity.

Most lawyers don’t have a money problem...
they have a “things won’t happen to me” problem.

Most lawyers I meet aren’t careless.
They’re just, shall we say...
optimistic.

• Optimistic that income will stay steady.
• Optimistic that health will hold.
• Optimistic that nothing unexpected will knock them sideways.

Until something does.

And that’s the moment
“I’ll get to it later”
turns into
“I should’ve done this sooner.”

Because it only takes one thing...
• one phone call
• one appointment
• one test result...
for “later” to become “too late.”

And here’s the part no one likes admitting:

Most lawyers aren’t reckless.
They're busy.
They’re overloaded.

And optimism is what fills the gaps they don’t have time to think about.

You don’t need paranoia.
don’t need perfection.

You just need to replace optimism with clarity.

Because the lawyers who feel calm?

They aren’t the ones earning the most.

They’re the ones who stopped assuming things would always stay the same.


👉 Does this sound at all familiar?

Funny how the right people show up at exactly the right time...

I just got off a long call with a group that’s become one of the best parts of my Wednesdays this past year.

Beyond the Apex — led by Anthony Vicino — has pushed me in ways I didn’t even know I needed.

It’s helped me get clearer on how Lamont Wealth Strategies and The Wealthy Lawyer Podcast can support lawyers at every stage…
from the final stretch of law school to partnership, firm-building, retirement, and life after law.

And with American Thanksgiving tomorrow, it felt right to pause and acknowledge how much this work — and the people in it — mean to me.

While I’m not sharing details yet, I can say this:

2026 will see me expand what I offer so more lawyers — in Canada, the U.S., and beyond — can get the clarity, structure, and support they deserve.

From protecting their families…
to building wealth intentionally…
to planning for retirement…
to creating legacies that outlive them.

I’m excited for what’s coming…
and grateful for everyone who’s been in my corner along the way.

So to my American friends…
Enjoy a meaningful holiday with friends and family, tomorrow, wherever you’re celebrating.


👉 What’s one thing you’re grateful for heading into tomorrow?


—
If you’re a lawyer wanting to simplify your financial world before the new year hits, let’s connect for a Virtual Coffee.

No pitch. No pressure. Just clarity.

Helping entrepreneurs build a business that maximizes their Return on Life. | ADHD is my superpower | Bestselling Author | Keynote Speaker | DM “COACH” if you’re ready to scale.

Lamont Wealth Strategies

The Wealthy Lawyer Podcast

Most lawyers don’t fear money…
They fear not doing it right.

I see it all the time.
That quiet moment when a lawyer stops mid-sentence, looks down for a second, and finally says:

“I make good money…
but I don’t actually know where it all goes.”

And here’s the part no one tells you:

• It’s rarely overspending.
• It’s rarely a discipline issue.
• It’s almost never “not caring.”

It’s the uncertainty.

The sense that you’re one step ahead in your career…
but half a step behind in saving and building.

The uncomfortable feeling that no one ever taught you how to manage money at this level…
and somehow you’re still expected to “just know.”

But here’s the truth:

Clarity doesn’t come from making more.
It comes from understanding the flow of what you already have.

Because almost every lawyer I work with has a similar pattern:

About 10% of their income goes unaccounted for.
Not stolen.
Not wasted.
Just… drifting.

A few quiet upgrades.
Some convenience purchases.
A busy month where “I’ll check it later” turns into later never happening…

And — POOF — and it’s gone!

So we walk through cash flow together.
We find the leaks.

Then we give that money a job going forward,
so it starts working as hard for you as you did for it.

And once that starts to click?

• Stress drops
• Confidence rises
• Life finally feels a little less chaotic

That’s when money finally feels like an ally…
not another pressure.


👉 Where does money feel the most unclear for you right now?
(I ask because your answer helps me shape posts that actually help.)

And if you’d rather sort this out with a guide, you can book a virtual coffee anytime through the“Become a Wealthy Lawyer” link in my profile.

You think everything is fine…
until life proves you wrong.

A few years ago, I sat across from a lawyer who’d been blindsided.

Brilliant woman.
Mother of two.
Partnership-track.
Income only going higher.

But her world changed overnight…
and what hit her hardest wasn’t the diagnosis.

It was the realization that nothing she had in place was actually built to fully protect her family.

Here’s what we found:
• Group disability that barely covered the mortgage
• Life insurance worth maybe two years of income
• No critical illness coverage
• A lifestyle built on today’s income… with no backup plan for tomorrow

And I’ll never forget when she looked up and said:

“I just assumed I’d get to it later.”

That sentence has stayed with me for years.

Because the truth is, most lawyers aren’t reckless…
they’re overwhelmed.

They’re building careers, raising kids, keeping the lights on…
and trusting that whatever they set up ten years ago is probably good enough.

Until it isn’t.

And when that day comes, the reaction is almost always the same:

A sigh.
A shake of the head.
And a quiet, painful…
“Why didn’t I look at this sooner?”

It wasn’t a massive mistake.
It was a 1% blind spot.
The kind that hides in plain sight until life forces it into focus.

Tomorrow’s first 1% Shift for Lawyers is exactly about this:

Why income protection comes first…
not tenth.
Why the foundation matters more than the shiny stuff.
Why one small adjustment can protect everything you’re working so hard to build.

More tomorrow.


💭 Do you know someone who’s had a heart attack, been diagnosed with cancer, or had something else pull them out of work unexpectedly?


☕ If you want to make sure your safety net is actually a net, let’s grab a Virtual Coffee.

What do you really get out of being on LinkedIn, anyway?

That was the question a friend threw at me recently.

Before I could even answer, they followed up with:
"Has it actually been good for business?"

I didn't realize the chat was turning into an interview.

Well… yes. I've met clients here. I've built partnerships here.

But truthfully? That's not the best part.

Connection. That's been the real win.

And I don't just mean clicking the "Connect" button.

I mean real conversations.
Shared experiences.
People I've never met in person who genuinely cheer me on...
and vice versa.

The best clients I work with?
They didn't come from a cold call or a sales pitch.
They came from conversations—real ones—where we connected first as people, then as professionals.

Recently, I had the chance to turn a couple of those online connections into real-life ones.

First was Patti Macdonald, founder of Fit Law LLP , who stopped in from Edmonton on her way to an east coast event.

Having spoken over Zoom and in the comments, sitting down in person felt like catching up with an old friend. We talked about life, LinkedIn, and building professional service businesses—great ideas, lots of laughs, and plenty of energy.

Then, during my trip to Austin for F1, I met Jess Sargus for coffee.

A lawyer turned MMA fighter turned business owner, Jess is a high-performance evangelist and keynote speaker who helps others unlock their inner badass. She also hosts The Legal Athlete  Podcast, where she bridges law, mindset, and performance.

We swapped stories about growth, balance, and how to get beyond your own self-doubt—with her sidekick, Paul Newman, joining us too.

Jess reminded me that high performance isn't about doing more—it's about getting clear on what matters. That hit different when you're building a business and trying to serve clients well.

Two incredible women I have the utmost respect for and am excited to call friends.

My only regret?
We forgot pictures.
But honestly, the best conversations don't need documentation…
they just need to happen again.

So as you scroll through here, remember...
behind every profile photo is a real person...
with a story worth hearing.

That's what makes LinkedIn special.

It's not just business. It's belonging.


💭 When was the last time you turned a LinkedIn connection into a real-world friendship? Tag them so we can all connect.


📸 here's Paul Newman… not quite as into the idea of LinkedIn coffee meetups... especially the ones that go long.

#KindnessAndDecency | Fit Law LLP | Founder | Changemaker | Leader | Innovator | Lawyer & Agent - Commercial Lending and Real Estate

Fit Law LLP

Self-Leadership & High-Performance Evangelist | Keynote Speaker | Certified Mental Performance Mastery Coach | Author of Fierce Agency™ (2026) | Ivy League-trained Lawyer, Undefeated MMA Fighter & Neuroscience Ninja

The Legal Athlete

Black Friday isn’t the danger…
Starting 2026 already behind — that’s the danger.

Every year, I see the same pattern:

Smart, thoughtful people walk into the holidays feeling excited and organized…
and walk into January shocked and already behind.

You worked all year to get ahead.
Don’t let one month quietly set you back.

Not because you’re reckless.
Not because you’re careless.

But because December is the one month where overspending feels “special,” “exceptional,” or “worth it.”

Until Blue Monday hits…
and that credit card bill shows up.

Don’t let the excitement of December’s gift-buying become January’s headache when you open that statement.

Because here’s what holiday overspending silently sabotages:

For most lawyers:
• Savings targets
• Debt repayment rhythm
• Investment contributions

For partners, it derails all of that plus:
• Corporate withdrawal strategy...
and with it, tax planning windows

So today, I encourage every client to do the same thing:

Before you buy anything, decide the number you won’t go past.
That top-line budget is the guardrail that protects next year’s goals.

A few simple rules help:

1. Set the ceiling first.
If you don’t pick the number, December will.

2. Use a spending calendar.
We overspend when all the decisions pile up at once — spread them out.

3. Stick to the list.
If it wasn’t on the list yesterday, it’s not suddenly a “deal.”

4. Decide what you’re not doing this year.
Impulse buys.
“Just in case” gifts.
Last-minute panic shopping.

The holidays feel better when the money part is calm.

You get to enjoy your people…
without waking up from this holiday shopping season with a full-blown January spending hangover.


Quick holiday question:
👉 Re-gifting — yes or no?
(Honesty encouraged. Judgement-free zone.)


────
I’m Jeffery, the advisor who wants to help you stay generous… and financially sane.

If you want help making sure 2025’s holiday spending doesn’t blow up your 2026 plan, let’s have a Virtual Coffee Chat.

📩 Send me a message or grab a spot through the link on my profile.

What’s old is new again.

For years, I had the print Globe & Mail delivered to the house.

Then someone convinced me to “go digital — it’s easier.”

Sure…
Great to have it on my iPad when I'm traveling and don't want to deal with carrying the paper...
but there was one problem:

No puzzles.

And as silly as it might sound, I missed my morning Sudoku and KenKen...
the quiet ritual that gets my brain firing before the day gets loud.

Sure, I was doing them on my iPad... sometimes, bit it just wasn't the same.

I prefer doing them pen in hand.

So this weekend, I went old school and restarted my print subscription.

Today was my first day back.

So, at 5:37am, I went downstairs...
got the paper off the porch...
made an iced coffee (still pretending it’s warm out)...
read through the Business section…
then hit my two favourite puzzles.
(Don’t @ me — crosswords and I have never gotten along.)

Why bring back something so simple?

Because it sharpens me.
It grounds me.
And it eases me into the morning just enough to think clearly before I jump into LinkedIn, and the client calls and problem-solving of the day.

I was a little rusty with them, but it felt good.
It felt familiar...
in a good way...
and as a reminder that sometimes the smallest rituals are all we need to get the day going right.


👉 What’s the thing you do every morning that gets you going?

It’s become almost cliché to talk about ‘1% improvements'...
but what the f*ck does that even mean?

Sure, “Get 1% better” sounds great…
but without direction?
It’s just another Instagram quote that disappears by Monday morning.

So for the next 5 weeks, I’m going to give you:

Small, clear, lawyer-focused shifts you can use immediately.

Shifts that will...
• Create clarity
• Lower financial stress
• Make decisions easier

One new shift every Tuesday.
One tiny action you can take that same day.

Nothing technical.
Nothing overwhelming.
Just the next right move.

See you Tuesday.
Let’s get after it.


💭 It’s Sunday night... how do you get ready for a killer week?


────
I’m Jeffery, the advisor who helps lawyers build financial clarity one small shift at a time.

☕ Want a head start?  Find the "Become a Wealthy Lawyer" link in my profile and let's talk.

Spend 30 minutes a week setting goals with your partner...
and you'll never argue about money surprises.

Talk. Plan. Align.

Next year?
Grow together.

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

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

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

li_at

JSESSIONID

LinkedIn Login, Sign in | LinkedIn

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

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

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

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

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

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

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

While everyone's fighting over TVs today, I'm fighting for your 2026.

One stage does what 6 months of content can't.

That's why I'm speaking in Austin December 10-12.

Here's what I've learned:

You can spend hundreds of hours posting content, cold DMing event hosts, vetting podcast opportunities, and hoping something sticks...

Or you can walk into one room where the work is already done.

That's Event Profit Engine.

Hosted by Alex Moscow ($130M in client results) and Eben Pagan (built 10 seven-figure companies, 3 over eight figures).

200 founders doing $500K-$2M+ in one room.

The kind of people you'd normally pay $25K to join a mastermind just to meet.

But this isn't networking. It's deal flow.

On Day 3, they run facilitated sessions where they literally pair you with:

→ High-caliber stages for 2026 
→ Aligned promotional partners 
→ Sponsors for your events (I am one of the sponsors for this event)

Not "hope you meet someone cool at the cocktail hour."

Strategic. Intentional. Partnerships that lead to revenue.

The stages you actually want to be on in 2026? They're in this room. The relationships that would take 6 months to build? Done in 3 days.

I'll be speaking on why most founders are operationally excellent but financially blind—and how to fix it.

This is for you if:
→ You're a founder doing $1M-$10M 
→ You want stages and partnerships locked in for 2026 
→ You're tired of cold outreach that goes nowhere 
→ You'd rather be in the right room than grind online for 6 more months

This is NOT for you if:
→ You're just getting started (under $500K) 
→ You're not ready to invest in growth 
→ You think "networking" means collecting business cards

Here's my Black Friday deal for you:

$1K tickets (normally $4K, goes to $5K on Monday).

I only have a few left. First come, first served.

You can fish with a pole for the next 6 months.

Or you can grab a net and walk into this room.

Comment "AUSTIN" or DM me and I'll send you the code before they're gone.
This is the only deal worth buying today.

See you in Texas.
#scalingup #CEO #founder #growth

He started with $5,000 and a pizza shop paycheck.
Nobody cared. Nobody believed.

Most people would’ve stayed broke.

Dan Gilbert didn’t.

He looked at a broken mortgage industry slow, complex, full of middlemen and said: “There’s a better way.”

He worked 18 hours a day. Seven days a week.
He studied every inefficiency.
He simplified the impossible.
He moved online when the internet was “just a fad.”
He ignored the naysayers.

It all started with Rock Financial. 
And eventually
Rock Financial became Quicken Loans.
Applications went from weeks to minutes.
Rates went from hidden to transparent.
Customers went from frustrated to obsessed.

Then he didn’t stop.
He bought the Cleveland Cavaliers, poured money into the city, and turned it upside down.
Downtown boomed. 
The team won a championship. 
The city transformed.

Here’s the lesson most people miss:

👉 You don’t need a perfect idea.
👉 You don’t need permission.
👉 You need to see broken systems, fix them better, and move faster than everyone else.
👉 And then, reinvest the wins into something that actually matters.

From pizza shifts to $28.5B, Gilbert’s story isn’t luck.
It’s obsession, timing, and execution.

Most people quit at “too hard.”
The few who succeed? 
They see the gap, go first, and keep building while others sleep.

If you want outsized results, do what most won’t:
Step past the “impossible.”
Step past the doubters.
Step past comfort.

Because fortune isn’t at the starting line, it’s at the point where everyone else stops.

#growth #scalingup #entrepreneurship #CEO #execution

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The Battle

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Performance Score.css-goub6s{font-size:var(--chakra-fontSizes-md);font-weight:500;color:var(--chakra-colors-gray-600);display:block;margin-top:var(--chakra-space-1);}Jeffery M. Lamont's LinkedIn Performance

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