Maya Grossman 💪 Career Success Coach

I will make you VP | Executive Coach and Corporate Rebel | 2x VP Marketing | Ex Google, Microsoft | Best-Selling Author

Hey, I'm Maya 👋
At the age of 27 I hit rock bottom - I completely burnt out trying to overwork my way into a promotion. 
Fast forward 15 years and I gained 10 promotions, worked for companies like Microsoft and Google, landed two VP roles at hyper growth startups, earned high six figures and actually enjoyed my 9-5.

What changed?
I stopped letting my career happen to me, and instead started managing it like a business.
I learned what it really takes to break through to executive roles, stopped making the mistakes that were holding me back, and developed the executive skills that got me noticed.

Today I am an executive career coach and my goal is to help you demystify what it takes to break through to executive roles, and build the bridge between where you are today, and where you want to be in your wildest dreams.

I want to save you the time, effort, and headache of figuring it out on your own and give you the playbook for achieving anything you want in your career.

My mission? To empower 1,000,000 high achievers to build the career of their dreams.


My brag list:

→ International best-selling author. Ranked  #1 new release for career books on Amazon.

→ 150,000+ followers across platforms, 70M views for my daily career advice
 
→ LinkedIn instructor (34,000 + learners, 4.7/5)

→ Named top 50 rising experts (US) and top 12 in Austin in 2023

→ Coached hundreds of high achievers to success on their terms​


If you are ready to level up in your career:

JOIN MY WEEKLY NEWSLETTER: Become VP Ready in 10 Minutes Per Week

Win the corporate game in 2025. Join 50,000+ high achievers receiving weekly actionable guides and proven strategies to level up into executive roles in months not years. 

www.mayagrossman.com/email


SUCCESS BUILDERS: BECOME THE OBVIOUS VP - 3-MONTHS GROUP COACHING PROGRAM

The exact steps to level up from Director to VP in months not years, without an MBA or working 80/h weeks

www.mayagrossman.com/SB


PRIVATE 1:1 COACHING

For senior executives who want to become first time VPs, or crush their first VP role.
I only offer 5 spots quarterly, and they require a 6-months commitment.

DM me for details.

Founder, Maya Grossman Consulting

Maya Grossman

You’re not too quiet.
You’re just being careful and it’s costing you visibility.

If you’ve ever held back in a meeting because you didn’t want to come off as “too much,” this is for you.

You don’t need to be louder. You need to be clearer.

Try this line next time you have a strong POV:
“I see it a little differently, can I walk you through my thinking?”

It signals confidence, respect, and strategic thinking, all without raising your voice.

You don’t get promoted for being agreeable.
You get promoted for leading conversations, not tiptoeing around them.

What’s one phrase you use to speak up with authority? Drop it below.

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Here is the link to the episode:
https://open.spotify.com/episode/6ebCBzi8Hi0uem5UHtzfcZ

This conversation is what happens when two former executives spill the best kept secrets about what it really takes to level up. 

I stopped getting more stuff done at work.
And that’s when my career finally started to move.

For a long time, I thought growth came from being helpful.

Saying yes.
Fixing problems.
Taking on work outside my role.

I was a marketer.
But I was also helping IT, managing company events, and responding to every “can you help with this?” request that came my way.

I was busy all the time.
Exhausted.
And still not getting pulled into bigger conversations.

What I didn’t understand at the time was why all that effort wasn’t translating into bigger opportunities.

The moment everything changed wasn’t burnout.

It was watching other people get promoted.

They weren’t working longer hours.
They weren’t saying yes to everything.

So I started paying attention.

They didn’t jump in to fix everything.
They talked about their thinking, not just what they delivered.
They were selective and intentional with their time.

So I tried it.

I stopped rescuing.
I stopped saying yes by default.
I stopped proving my value through output alone.

And it felt uncomfortable.
It went against everything that had worked for me before.

But here’s what surprised me.

No one thought I was less committed.
No one questioned my value.

Instead, people asked for my opinion.
They pulled me into conversations earlier.
They treated me differently.

That’s when it clicked.

At senior levels, doing more doesn’t help you stand out.
It just keeps you busy.

If you’re delivering results and still not moving up, the answer probably isn’t more effort.
It’s a different way of showing up.

What’s one thing you’ll stop doing to break the cycle?

I stopped getting more stuff done at work

Why Directors in tech get stuck before VP ⬇️

Directors who want a VP role often make the same quiet mistake:
They give updates instead of opinions.

That signals one thing to leadership:
“I execute well but I don’t own decisions.”

You can be sharp.
You can be polished.
You can be delivering real results.

And still disqualify yourself from the room where direction is set.

Because if leadership only hears what happened and never what you think should happen next, they won’t see you as VP-ready.

They’ll see you as dependable execution.

The shift isn’t louder communication.
It’s higher-altitude thinking.

Comment VP and I’ll send you a free masterclass where I break down how to move from reporting work → being trusted with decisions.

Watch how quickly the conversations around you change.

Most people getting passed over for VP are not underperforming.
They're over-performing at the wrong level.

These are the doer habits that look impressive on paper but quietly stall your promotion:

- Saying yes to everything (a.k.a people pleasing)
- Waiting for permission
- Presenting options instead of making calls
- Over-explaining to prove credibility
- Solving problems only inside your lane
- Only offering insights when asked

The truth is none of these are "bad habits."

They're rewarded early in your career.

But at senior levels, they send a very clear signal:
"You're reliable execution. Not leadership judgment."

VPs are not promoted because they do more.
They're promoted because they decide better.

They choose where to focus.
They make calls with incomplete data.
They connect dots across the business.
They influence outcomes without owning every task.

That's why burnout is so common right before the VP leap.

You're carrying Director-level work with doer-level habits.
Not good.

If you want to learn how to retire doer habits and start showing up as an executive decision-maker, I'm breaking it down step by step in my free masterclass.

Comment VP and I'll send you the details.

And yes, this is the work that actually changes how leaders see you.

P.S. How many of these are you still doing without realizing it?

6 Doer Habits That Kill Promotions

If you feel overlooked, there’s a good chance you’re selling yourself short.

Right now, there are people getting noticed, pulled into bigger conversations, and promoted
while doing a fraction of the work you’re doing.

They’re not smarter.
They’re not working harder.
They’re not delivering better results.

They’re just better at communicating their impact.

Meanwhile, many high performers talk themselves out of visibility with thoughts like:
“It’s just my day job.”
“It’s not that impressive.”
“I didn’t 10x anything.”
“I was just doing what I was supposed to do.”

That mindset is quietly killing your leverage.

Here’s the shift I want you to make:

Stop evaluating your work based on effort.
Start evaluating it based on impact.

Two questions to ask yourself about anything you’re working on:

1. What did this make easier, faster, cheaper, or better for the business?
2. And what would have happened if I hadn’t stepped in?

If you’re thinking, “But my work isn’t quantifiable,” let me give you a real example.

One of my clients, we’ll call her Natalie, works in finance.
Part of her role was producing a monthly report for leadership.

When she inherited the process, it required:
three people
working three full days
every single month.

It drove her crazy.

So she redesigned the process.

The result?
The same report now takes one person two hours.

At first, she described this as:
“Oh, I improved the process.”

No one cared.

Then she learned to quantify it.

This new system will save us roughly three full months of work this year,
which frees up budget for an additional headcount
and allows the team to focus on higher-impact work.”

Same work.
Different framing.
Completely different perception.

If you’re not being recognized, don’t assume your work isn’t valuable.
Ask whether you’re underselling it.

Because the people getting ahead aren’t always doing more.
They’re just making the value of what they already do impossible to ignore.

♻️ Share with someone who needs to stop underselling themselves

Let me normalize something about senior leadership.

I didn’t get to VP by being perfect.

In fact, I’ve made mistakes that cost companies hundreds of thousands of dollars.

I’ve backed the wrong campaigns.
Missed targets.
Made bets that set teams back months.

I’ve walked into senior leadership meetings confident... and then completely frozen.

Once I literally couldn’t get a single word out.

I’ve missed deadlines I owned.
I’ve mishandled people.

Not because I didn’t care, but because I didn’t yet know how to lead at the level the role required.

I’ve lost my temper.
I’ve gotten into real fights with my CEO.

None of that looks great on a highlight reel.

But these screw-ups taught me the most.

But here’s what people don’t tell you early in your career.

Executives are not the people who never mess up.

They’re the people who learn how to recover, take ownership, and make better calls next time.

Those mistakes taught me:

- How to make decisions with incomplete information
- How to stand back up after public failure
- How to repair trust when you’ve damaged it
- How to lead people when you don’t have all the answers yet

Perfection never made anyone VP.

Judgment did. Accountability did. Growth did.

If you’re waiting to feel flawless before you aim higher, you’re playing the wrong game.

I break down how senior leaders actually develop this judgment, without burning themselves out or pretending they’ve never failed, in a short, pre-recorded masterclass: https://lnkd.in/gG8GnY4Y

The difference between a Director and a VP isn’t strategy.
It’s where they spend their energy.

A Director puts their energy into getting things done.
A VP puts their energy into shaping what gets done and how.

That took me a long time to learn.

Early in my career, I genuinely believed my value came from output.

From doing more.
From being indispensable in execution.

Spending time thinking, networking, or stepping back to shape direction felt irresponsible.

Almost lazy.

If I wasn’t doing, how was I adding value?

I see the same belief with a lot of high achievers.

They assume that if they stop being the one who carries everything, they’ll matter less.

The opposite is true.

The Director:

→ Jumps in to solve problems
→ Personally drives key initiatives
→ Fixes issues when things go sideways
→ Is deeply involved in execution
→ Becomes the person everyone relies on

They’re effective.
They’re trusted.
They’re also at the center of everything.

The VP:

→ Decides what deserves attention and what doesn’t
→ Sets direction before problems show up
→ Builds leaders who can make calls without escalation
→ Creates clarity so execution happens without them
→ Is comfortable not being in the middle

Here’s the shift that changes how you’re seen:

Directors add value by doing.
VPs add value by deciding.

What to prioritize.
What to deprioritize.
What tradeoffs to accept.
What problems not to solve.

Letting go of “doing” doesn’t make you less valuable.

It makes room for the kind of value senior leaders are actually looking for.

That’s when the conversation changes.

And if you’re not sure what they’re looking for in a VP, I break it down here: https://lnkd.in/gG8GnY4Y

Never take a promotion without a raise sounds smart. 
It isn’t

On the surface, it feels like a strong boundary.
It sounds fair.

But it also ignores how leverage actually work.

Of course, in a perfect world, more responsibility comes with more pay.

And long term, I don’t want anyone doing expanded work without compensation.

But...
If you’re offered a promotion without an immediate raise, the real question isn’t:

“Is this fair?”

It’s:
“What does this unlock?”

Because a few things matter here.

First, momentum.
When leaders offer you a promotion, they’re moving forward.

If you say no, the odds of them coming back later are low. 
They don’t sit around waiting.

Second, signal.
The title, scope, and visibility change how you’re seen.

Internally and externally.

That signal is powerful.
Especially if you want to get a new job that pays your worth instead of moving latterly. 

Third, leverage.
Once you’ve operated at the higher level for a few months,
you’re no longer negotiating as who you were.

You’re negotiating as the leader you’ve already proven yourself to be.

That’s going to unlock 5 and 6 figure raises.

This is how senior leaders think.

Not, “Is this fair today?”
But, “What does this position me for next?”

The mistake isn’t taking a promotion without a raise.
The mistake is taking it without a plan.

“Never take a promotion without a raise” sounds smart on the internet.
In real careers, it’s incomplete advice from people who don’t think past the next paycheck.

Senior leaders don’t win by waiting for fair.
They win by being strategic.

P.S.
The people who use this strategy don’t stay underpaid for long.

“I want to move from Director to VP, so I’m focusing on job search.”

Every time I hear this, my heart sinks.
Because I know what usually follows.

Resume updates.
Applying on LinkedIn.
Waiting to be picked.
Hoping a new company will change how you’re seen.

That’s the lie we tell ourselves to stay comfortable.

Calling it “job search” makes it feel familiar.

Like there’s a clear process.

But moving from Director to VP is rarely a job search problem.

It’s an identity shift.

VP roles aren’t won by resumes.
They’re won by positioning, credibility, and presence.

The people making the decision have to see you as ready.
And no amount of keywords can replace that.

Last year we’ve had 15 client promotions.

More than half were leaders leveling up while changing companies and getting new jobs.

None of them applied online.
None of them updated their resume 23 times.

They followed a different strategy:

They got clear on their VP-level value.
They learned how to talk about it strategically.
They pressure-tested it with successful VPs.
They built real relationships with senior leaders.
They showed up as peers, not candidates.

And got the job even though their resume said “Director”.

One client reached out after 8 months of “job search.”

No traction. No momentum.

She was ready to give up and move latterly.
But instead we changed the strategy.

We worked on her positioning.

Her story.
Her network.
Her presence.

A few months later, she landed her first VP role.

Because it was never about job search.

It was about becoming ready.

I talk about this all the time and yet...

So many high achievers still choose the same “job search” approach
and stay stuck.

That’s the part that breaks my heart.

Because their effort isn’t the issue.
Their talent isn’t the issue.

The strategy is.

If you’re a Director aiming for VP and all you’re doing is applying
you’re playing the wrong game.

There are 3 shifts that position you as VP-Ready and you can learn all of them in the next 25 minutes.

Start here: https://lnkd.in/gG8GnY4Y

"She can handle anything" is not a compliment.

It feels flattering.
It also keeps people stuck.

Let me tell you about a client - I'll call her Lina.

Every big, messy initiative eventually landed on her plate.

New product launch that slipped three times?
Lina will fix it.

Cross-functional project with fifteen stakeholders and no owner?
Lina will take it.

Leader going on parental leave, team in chaos?
Lina can step in.

Her reputation was simple:
"She can handle anything."

Then promotion season came.

Her VP said the words that cut the deepest:
"You're incredible. I don't know what we'd do without you. Let's revisit promotion next cycle."

She was everywhere, doing everything...
and still not seen as "ready for more."

When we unpacked it, the pattern was obvious:

She was solving everyone’s problems, not driving her own charter
Her impact stories were about rescue missions, not business outcomes
Leaders were afraid to move her because she was too useful where she was

Sound familiar?

If the story people tell about you is "we would fall apart without them,"
it feels like praise.

But it's actually a trap.

Here's the reframing exercise I gave Lina.
Do it yourself this week:

Write down three major projects you led in the last 12 - 18 months.

For each one, answer:

1. If I vanished tomorrow, what measurable result would disappear with me?
2. How did this project change the business in ways leaders actually care about?

Now rewrite your story of the project using only those answers.
Not the chaos you survived.
Not the hours.
Not the crisis management.

Your goal is to shift from:
"I held everything together"
to
"I moved this metric and this outcome."

That is the language of VP decisions.

If you want to learn how to take the work you're already doing and turn it into a real promotion case, I cover it in my free masterclass: https://lnkd.in/gG8GnY4Y

Becoming a VP wasn’t about confidence first.
It was about action first.

Every career-changing move I made felt uncomfortable when I made it.
Asking for feedback I wasn’t sure I could handle.
Being explicit about my ambition.
Letting go of work I was good at so I could take on work I wasn’t.

None of that felt “ready.”
All of it changed my trajectory.

If you are doing excellent work but still waiting to be seen as VP material, this is your sign to stop waiting.

I teach exactly how to make these moves without burning bridges or blowing up your reputation inside my free masterclass: https://lnkd.in/gG8GnY4Y

Rating the hard things I did to become a VP

When I first started working on my executive presence
I made the same mistake most high achievers make:

I thought it meant becoming someone else.
I tried sounding more polished.
Rehearsed every sentence.
Softened my personality so I could “fit” the leadership mold.

And it was miserable.

I kept thinking,
“If I can just act like a typical exec, maybe they’ll finally take me seriously.”

But all it did was make me frustrated, disconnected, and tired.
Because executive presence isn’t about faking polish.

It’s about learning to lead as yourself.
With clarity, conviction, and impact.

My turning point wasn’t some glamorous leadership epiphany.

It was burnout.

The kind where you’re lying on the floor wondering why you’re trying so hard to be someone you’re not.

That’s when I made a decision:
If the only path to leadership required pretending, I didn’t want it.

So I stopped performing and started aligning.

I leaned into the strengths that were already there:

→ Direct communication
→ Real, trusting relationships
→ Calm when things went sideways
→ Clear strategic thinking instead of jargon

I wasn’t the “typical” executive and that’s exactly why things started working.

Once I showed up as myself with presence, not pretense, everything shifted:

→ Two VP roles
→ A high six-figure salary
→ Teams who trusted me
→ Leaders who backed me

Because when I communicated with clarity instead of corporate-speak,
and led with authenticity instead of acting...

People finally saw what I actually brought to the table.

Here’s the real lesson:
Executive presence isn’t a costume.
It’s embodied leadership.

And the moment you stop trying to fit in?

You finally stand out.

If you’re wondering: Am I making this mistake? Watch this 25 min breakdown to get your answer: https://lnkd.in/gG8GnY4Y

My nervous system used to run my career. Now, I run it.
Because I started doing these 3 things (and you can too):

For years I thought I needed more skills to get promoted.

More training. More experience. More credentials.

But the truth was surprising:
I didn't rise just because my capability expanded.

I rose because my capacity did.

I could lead a team.
I could deliver results.

But in the moments that mattered most, my body shut me down.

My voice shook when I needed it steady.
My mind blanked in front of senior leaders.

I stayed quiet in rooms where I should have owned the conversation.

Not because I wasn't ready.
But because my nervous system was in overdrive.

Once I understood that, everything changed.

Here are the 3 practices that helped me step into real executive presence:

1. I trained myself to sit in discomfort instead of escaping it
I used to avoid anything that made my chest tighten or my stomach drop.

Now I sit with it for 60 seconds.

No fixing. No distracting. Just noticing.

This built more emotional strength than any leadership course I ever took.

Try this:

Next time discomfort shows up, pause for 60 seconds.
Name it.

"This is activation."
"This is freeze."

Naming reduces intensity instantly.

2. I rewrote the story my body was telling me
Same physical signals. New interpretation.

Old thought: my heart is racing so something is wrong.
New thought: my heart is racing because my body is preparing me.

Same sensation. 

Completely different outcome.

Try this:
Before a high stakes moment, tell yourself:
"I am not nervous. I am preparing."

Elite performers do this for a reason. It works.

3. I asked one question before every brave action
Fear used to make every decision for me.

Until I started asking:
"What would the leader I am becoming do right now?"

Not the stressed version of me.
Not the overthinking version.

The future version.

That question changed how I spoke, how I led, and the risks I was willing to take.
It changed my career trajectory more than any skill I ever mastered.

Try this:
Use that question once a day.
Let future you lead the moment.

Skills matter.

But capacity decides whether you can use them when it counts.

If this hit you in the gut, save this post and use it.
If you are ready to lead at a higher level, follow me. I teach this every week.

You already have the skills.
If you want help building the capacity to use them when it counts, I put everything I teach my clients into a 25-minute session you can watch on demand. No fluff, just the framework: https://lnkd.in/gG8GnY4Y

She came to me saying she wanted to get to VP.

Her plan sounded familiar:
Take on more projects.
Say yes more often.
Be the person who always delivers.

On paper, it looked like ambition.

So I asked her a question most high performers never stop to ask:

“What do you want to feel differently once you’re a VP?”

She didn’t say “busier.”

She said:
“I want my opinion to matter.”
“I want to influence decisions, not just execute them.”
“I want my work to actually move the business, not just keep it running.”

Then I asked the uncomfortable follow-up:

“Will doing more work get you that?”

She already knew the answer.

No.
It would make her reliable.
Not influential.

We scrapped the ‘more work’ strategy and rebuilt around what VPs are actually paid for:

• Fewer initiatives, bigger stakes
• Clear points of view, not endless updates
• Ownership of outcomes, not tasks

What changed?

She wasn’t working less hours.
She wasn’t coasting.

But she was:
• Asked for recommendations instead of status
• Brought into decisions earlier
• Trusted to shape direction, not just deliver

She told me:
”This is the first time my work feels like it matters at the top”

That’s what happens when you follow the right strategy.

Not more work.
More impact.
More influence.
More fulfillment.

If your promotion strategy is still “do more,” you’re optimizing for the wrong outcome.

Before you take on one more project, ask yourself:

“Will this actually increase my impact?”

Then build your promotion strategy around it.

If you’re not sure where to start, I’ve got you.
Start here: https://lnkd.in/gG8GnY4Y

“My wife says I’m a different man.”
That’s what one of my clients told me last week.

Not because he got a shoutout from the CEO.
Not because the executive team finally sees him as executive material.
Not even because, after three years of waiting, the promotion is finally on the books.

Those things matter.

But that’s not the real transformation.

The real shift was this:

He stopped showing up like someone hoping for a chance.
He started showing up like someone who creates his own.

More confident.
More positive.
More strategic.
More grounded.

A different man.

And here’s what I want people to understand:

My program doesn’t give you a short-term confidence bump.

It doesn’t hype you up for 13 weeks and then drop you back where you started.

It rewires how you think.

How you lead.
How you see yourself.

Because career growth isn’t about learning tactics.

It’s about becoming the person who naturally gets the opportunities everyone else waits for.

This client walked in believing his next decade would look just like the last.

He walked out with executive recognition, a promotion in motion, and a completely different identity.

And that doesn’t fade.

That stays.

If you want external change, you need internal transformation.

That’s the work we do.

Want to take the first steps? Start here: https://lnkd.in/gG8GnY4Y

My client just added $216K to her OTE with one conversation.

And it was the one she really didn’t want to have.

There was no bidding war.
No dramatic standoff.
No leverage from multiple offers.

Just one clear, uncomfortable conversation negotiating the first offer.

Here’s what actually made it work:
This wasn’t about negotiation tactics.
It was about executive confidence.

At the VP level, avoiding hard conversations is a liability.

You’re expected to ask for what you want, hold boundaries, and stay grounded under pressure.

She walked in clear on three things:

1. What she wanted.
Not what sounded reasonable. What she actually wanted.

2. Her red lines.
Knowing exactly where she would and wouldn’t compromise removed the emotional noise.

3. Her proof.
When confidence wobbles, facts don’t. Scope, results, impact.

This is the part most people miss.

If you can’t advocate for yourself and ask for what you want you’re not signaling executive readiness yet.

Negotiation isn’t a special event.
It’s part of the job.

This is what executive confidence looks like in real life.
Not louder. Not aggressive.
Clear, grounded, and willing to have the conversation most people avoid.


P.S.
Not knowing how to advocate for yourself is a leadership skill gap that eventually shows up in your title, scope, and pay. But... anyone, and I mean anyone, can learn it.

I break it down in a free 25-minute training: https://lnkd.in/gG8GnY4Y

No one tells you how your life actually changes when you become a VP.

Everyone talks about the title.
The salary.
The scope.

The biggest shifts are the ones no one sees on LinkedIn.

One client, Shawna, told me she had never been more confident in herself.
Not in a loud way. In a grounded way.

She said it felt like she rediscovered who she really was.

That confidence didn’t just change how she showed up at work.
It opened doors everywhere in her life.
(Including with her daughter)

Another client, Vincent, said something that warmed my heart.
He told me his wife said he is “a completely different person”.

Not because his job changed overnight, but because he stopped doubting what he was capable of.

He learned how to trust himself under pressure.
How to stand behind his decisions.
How to stop shrinking in moments that mattered.

And then there’s the client who negotiated a six-figure increase to her total compensation and told me,
“I will never sell myself short again.”

That sentence matters more than the number.

These are the changes people don’t talk about.
They don’t show up in announcements or job updates.

But this is how real change happens.

Becoming an executive isn’t just about getting the role.
It’s about who you become in the process.

It’s about stepping into the most capable, grounded, confident version of yourself.

That version changes your career.
And it changes your life.

That’s the business I’m in.

I recorded a short masterclass on what actually changes when you step into senior leadership, beyond the role itself: https://lnkd.in/gG8GnY4Y

Meet Ryan. Not his real name, but his story is very real.
He joined my program with one clear plan: get promoted.

Six weeks later there were layoffs.

Suddenly the question wasn’t “How do I get promoted?”

It was “What the hell do I want next?”

And “How do I get it before my family spirals into panic?”

Here’s the part most people won’t admit out loud:

Ryan had spent years as a Director... quietly hoping the VP job would just find him.

He had a great reputation.
A strong network.
A track record that could go toe-to-toe with any VP.

But he never actually declared what he wanted.

Not to himself.
Not to other people.
Not even in his networking conversations.

So guess what his network sent him?

Director roles.
Mid-level roles.
“Safe” roles.

Nothing he actually wanted.

Months passed. His family got anxious. He got anxious.

He started interviewing for Director positions just to make the stress stop.

And then something interesting happened.

Multiple interviewers told him

“You’re overqualified. You should be going for VP.”

That was the moment.

He had to admit to himself what everyone else already saw.

He was ready.

He was just scared.

So he made a decision.

Not “I hope something happens.”
Not “Maybe someone will pick me.”

But: I’m done compromising. I’m going after the job I actually want.

And then he backed it up with action.

- He put himself into real rooms
Community events. Industry meetups. Conferences.

- He built social proof
One thoughtful LinkedIn post a week. Nothing fancy. Just credibility in public.

- He doubled down on strategic networking
Not “catching up with old contacts.”

Actual conversations with leaders doing interesting work.

Peers. Founders. CEOs.

People who open doors that don’t exist yet.

But the biggest shift?

He stopped panicking about not having a job.
He stopped trying to force the next step.
He finally relaxed into the identity he’d been avoiding.

And then something happened that still makes me smile.

On his way to a short vacation, he got a call.
From someone he’d met six months earlier.

“Are you free to meet our CEO? We think you’re the person we need.”

There was no job posting.

No hiring plan.
No formal search.

One meeting later: VP offer.

At a company on the verge of doing groundbreaking work in his field.

When I asked him if the wait was worth it, he laughed.

“Hell yes. I’d do it again. I’d just take action faster next time.”

Here’s the truth his story teaches:
Even in a brutal job market, opportunity shows up fast when you show up first.

He didn’t manifest it.

He created it.
He positioned himself for VP.
He built visibility.
He expanded his network beyond comfort.
He took action when it felt terrifying.

And he landed his dream role.

If you’re a Director sitting on VP-level experience but waiting for permission

2026 is not the year to play small.

Stop hoping. Start positioning. Opportunities follow visibility.

There’s a very specific version of “executive” we’re all taught to copy.

Formal.
Distant.
Buttoned-up.

Careful with words.
Careful with people.
Careful with opinions.

I tried that version early in my career.

And it never felt like me.

So I did the opposite.

I wore jeans and a t-shirt.
I knew my team deeply, personally, humanly.
I said what I actually thought instead of dressing it up in jargon.
I moved fast when things felt slow and political.

I didn’t wait to be “ready” before deciding what I wanted next.

And yes, that made some traditional corporate executives flinch.

But here’s what surprised me:

I didn’t lose credibility.
I gained it.

Because leadership isn’t about fitting a mold.

It’s about trust. Judgment. Clarity. Results.

I didn’t become a VP by changing who I was.
I became a VP by owning who I was and letting my leadership speak for itself.

That’s the part no one tells you.

If you think you need to become more polished, more corporate, more performative to get promoted... you don’t.

I break this down in my free masterclass:
how promotions actually work, how perception really shifts, and how to lead at the next level without selling out your personality.

https://lnkd.in/gG8GnY4Y

Things I did as a VP that will make traditional corporate executives run for the hills 

For years, I avoided self-promotion.
Because the only version I’d seen was:
Loud, ego-driven, and inauthentic.

And I didn’t want to be that person.

So I did the opposite.

I kept my head down.
Let my work speak for itself.
Assumed results would be enough.

They weren’t.

Avoiding self-advocacy didn’t make me humble.
It made me invisible.

And I learned very quickly that invisible people don’t get promoted.

The turning point was realizing there was another way.
I didn’t need to brag or sound cringe worthy.
I could frame my impact in a way leaders actually understand it.

Once I figured it out - it was like magic.
I turned everyday moments into mini self promotion opportunities.

- Meetings
- Emails
- Slack
- 1:1

And by dropping small self advocacy hints all the time...
My trajectory changed without me becoming someone else.

If self-promotion makes you uncomfortable,
the problem isn’t that you’re bad at it.

It’s that no one taught you a better way.

Let’s change that: https://lnkd.in/gG8GnY4Y

Avoiding self

Christopher Nelson

Helping You Build Wealth with Tech Equity and become the Founder of Your Financial Independence

In the early 2000s,  my focus was on growing my skills, climbing the ladder, and being where I needed to be to get the job done. 

In 2009, I burned out hard. 

My new plan was to work for equity in tech start-ups and become financially independent.

Swing and Miss, the first start-up company I chose to work for, was going nowhere (equity worth zero). 

What happened? Did I screw up everything?

I chose the company because I was passionate about its mission, but I had not examined it further. I had no real plan.

My next step was to call people that I knew had been successful in working for equity in tech and see what was different in their "playbook."

Key lessons learned after first dead-end tech startup:
 -In trading my time and talent for equity, I need to think like an investor
 -Create a rigorous due diligence process
 -Don't fear failure, stay in the game
 -Keep learning

May 2011, Started at Splunk Pre-IPO

April 19th, 2012 Splunk had a break-out IPO

April 20th, 2012 feelings of anxiety and fear creep in about how to manage the newly generated wealth. 

I had to figure out how to get real income (real estate) into my portfolio. I needed something sending me checks.

Key lessons learned after the first IPO:
 -How to invest in private equity real estate
 -Set up my family for generational wealth
 -Own the result (don't put my future in someone else's hands)

New Mission: Be the Founder of a Micro Family Office to become Financially Independent.

Strategy:
 -Live within paychecks
 -Bonuses for extras
 -Invest all of our equity

I climbed the ladder to become a CIO. 

At the peak, I realized I wanted to build my DIY Family Office more than climb the ladder.

I changed roles and reduced my scope. 

On August 26, 2022, I graduated from my W-2 job to live a lifestyle by design.

I founded WealthOps in 2023 to equip technology professionals with the skills to build and run their portfolios.

My Portfolio:
 -3  Start-Ups I worked for IPOed (SPLK, YEXT, GTLB) <-Traded Time
 -Replaced paycheck with $200k+ of portfolio income
 -Built my Micro Family Office
 -Running a company structured around my life

My Results:
 -Highly Diversified Portfolio - Stocks, PE Real Estate, Debt, Businesses, and VC. 
 -$223 Million AUM with investors
 -7 Investments  gone full cycle with an Avg 19.4% IRR to investors
 -1000+ tech employees being educated on Managing Tech Millions
 -20+  and growing Portfolio CEOs

My mission - 1000+ Portfolio CEOs

Learn more about how I did this, join our free live workshop  →  https://dub.sh/wealthops-linkedin

Founder

Tech Careers and Money { }, a media and education company whose mission is to elevate Tech Professionals' finance knowledge through unmatched and unbiased education in career and personal finance to equip them to make their best decisions. 


Subscribe to learn about career growth, tech equity,  portfolio income, investing, budgeting, student loans, and more.

I built my own family office from scratch.

Here's how.

I didn't need $100M in assets. 
I didn't hire a $500K/year staff. 
I didn't wait for permission from a wealth manager.

I spent a decade studying how Single Family Offices operate.

The ones managing $500M+.

And I stripped them down to their core operating system.

Here's what I found: 

𝗘𝘃𝗲𝗿𝘆 𝗼𝗻𝗲 𝗼𝗳 𝘁𝗵𝗲𝗺 𝗿𝘂𝗻𝘀 𝗼𝗻 𝘁𝗵𝗲 𝘀𝗮𝗺𝗲 𝟳 𝗰𝗼𝗺𝗽𝗼𝗻𝗲𝗻𝘁𝘀.

1) Vision
2) Structure
3) Protection
4) Process
5) Data
6) Advisory Partners
7) Governance

That's it. 

Doesn't matter if it's $500M or $5M, the operating system is the same. 

The scale is different. 
The architecture isn't.

I call this scaled down version the 𝗠𝗶𝗰𝗿𝗼 𝗙𝗮𝗺𝗶𝗹𝘆 𝗢𝗳𝗳𝗶𝗰𝗲.

Most wealthy families have 1-2 of these components partially in place. 

Maybe a financial advisor (Advisory Partners). 

Maybe a basic portfolio (Structure). 

But without all 7 working together, you're running a business with missing departments.

The families who get this right don't outperform because they pick better stocks. 

They outperform because they run better operations.

The infographic below breaks down all 7 components and how they connect. 

Screenshot it. 

In a few days, I'm hosting a live workshop on how to set up components 1 and 2 in your own Micro Family Office.

𝗬𝗼𝘂 𝗰𝗮𝗻 𝗿𝗲𝗴𝗶𝘀𝘁𝗲𝗿 𝗵𝗲𝗿𝗲: https://dub.sh/mN0g8tK

Here is what attendees from last month's workshop said about it:

𝘐𝘵 𝘸𝘢𝘴 𝘳𝘦𝘢𝘭𝘭𝘺 𝘴𝘵𝘳𝘢𝘯𝘨𝘦 𝘵𝘰 𝘧𝘪𝘯𝘥 𝘴𝘰𝘮𝘦𝘰𝘯𝘦 𝘪𝘯 𝘺𝘰𝘶𝘳 𝘱𝘰𝘴𝘪𝘵𝘪𝘰𝘯 𝘵𝘰 𝘥𝘰 𝘵𝘩𝘪𝘴. 𝘐𝘵'𝘴 𝘵𝘩𝘦 𝘧𝘪𝘳𝘴𝘵 𝘵𝘶𝘵𝘰𝘳𝘪𝘢𝘭 𝘐 𝘤𝘢𝘯 𝘵𝘩𝘪𝘯𝘬 𝘰𝘧 𝘵𝘩𝘢𝘵'𝘴 𝘢𝘤𝘵𝘶𝘢𝘭𝘭𝘺 𝘴𝘢𝘺𝘪𝘯𝘨 𝘴𝘰𝘮𝘦𝘵𝘩𝘪𝘯𝘨 𝘶𝘴𝘦𝘧𝘶𝘭 𝘢𝘯𝘥 𝘶𝘯𝘣𝘦𝘭𝘪𝘦𝘷𝘢𝘣𝘭𝘦.
– 𝗠𝗮𝘂𝗿í𝗰𝗶𝗼 𝗛.

𝘠𝘰𝘶 𝘫𝘶𝘴𝘵 𝘨𝘢𝘷𝘦 𝘮𝘦 𝘵𝘩𝘦 𝘧𝘳𝘢𝘮𝘦𝘸𝘰𝘳𝘬 𝘵𝘩𝘢𝘵 𝘐 𝘸𝘢𝘴 𝘮𝘪𝘴𝘴𝘪𝘯𝘨, 𝘢𝘯𝘥 𝘐 𝘥𝘪𝘥𝘯'𝘵 𝘬𝘯𝘰𝘸 𝘵𝘩𝘢𝘵 𝘐 𝘯𝘦𝘦𝘥𝘦𝘥.
– 𝗖𝗵𝗿𝗶𝘀𝘁𝘆 𝗪.

𝘐 𝘵𝘩𝘰𝘶𝘨𝘩𝘵 𝘵𝘩𝘢𝘵 𝘸𝘢𝘴 𝘨𝘳𝘦𝘢𝘵. 𝘈𝘯𝘥 𝘐 𝘵𝘩𝘪𝘯𝘬 𝘪𝘵'𝘴 𝘴𝘰 𝘧𝘶𝘯𝘯𝘺 𝘣𝘦𝘤𝘢𝘶𝘴𝘦 𝘵𝘰 𝘮𝘦, 𝘐 𝘸𝘪𝘴𝘩 𝘐 𝘩𝘢𝘥 𝘵𝘩𝘪𝘴 𝘱𝘳𝘦𝘴𝘦𝘯𝘵𝘢𝘵𝘪𝘰𝘯 𝘭𝘪𝘬𝘦 𝘧𝘪𝘷𝘦 𝘺𝘦𝘢𝘳𝘴 𝘢𝘨𝘰.
– 𝗣𝗮𝘀𝗰𝗮𝗹 𝗪.

I Run My Own Micro Family Office and Teach Others to Do the Same | Founder @ WealthOps

The 7 components of a Micro Family Office.

Family offices aren't about the money.

They're about the operating system.

Most people think family offices are for billionaires.

But thats just not true.

A Single Family Office ($100M+) has a full staff managing investments, estate planning, tax strategy, and philanthropy.

A Multi Family Office ($30M-$100M) pools resources across multiple families sharing advisors.

But here's what nobody tells you:

The 𝗽𝗿𝗶𝗻𝗰𝗶𝗽𝗹𝗲𝘀 that make these structures work have nothing to do with the dollar amount.

They work because of:
→ Systematic decision-making
→ Coordinated advisory teams
→ Integrated tax strategy
→ Operational cadence
→ Clear governance

These aren't "rich people things."

𝘛𝘩𝘦𝘺'𝘳𝘦 𝘣𝘶𝘴𝘪𝘯𝘦𝘴𝘴 𝘰𝘱𝘦𝘳𝘢𝘵𝘪𝘰𝘯𝘴.

And if you've built wealth to $1M-$30M, you already know how to run operations.

You've ran a P&L.
You've managed teams. 
You've shipped products. 

You possess the skills. 

You're just applying them to a new domain.

That's the Micro Family Office.

Not a watered-down version of what the ultra-wealthy have.

A lean version built on the same 7 components—scaled for portfolios our size.

𝗦𝗮𝗺𝗲 𝗽𝗿𝗶𝗻𝗰𝗶𝗽𝗹𝗲𝘀. 𝗦𝗰𝗮𝗹𝗲𝗱 𝗲𝘅𝗲𝗰𝘂𝘁𝗶𝗼𝗻.

The question isn't whether you qualify for family office infrastructure.

It's whether you're willing to build it.

On Feb 25th, I'm hosting a 𝗹𝗶𝘃𝗲 𝘄𝗼𝗿𝗸𝘀𝗵𝗼𝗽 to help you architect the foundation for your Micro Family Office.

𝗬𝗼𝘂 𝗰𝗮𝗻 𝗿𝗲𝗴𝗶𝘀𝘁𝗲𝗿 𝗵𝗲𝗿𝗲: https://dub.sh/mN0g8tK

Here's what attendees from last month said:

𝘐𝘵 𝘸𝘢𝘴 𝘳𝘦𝘢𝘭𝘭𝘺 𝘴𝘵𝘳𝘢𝘯𝘨𝘦 𝘵𝘰 𝘧𝘪𝘯𝘥 𝘴𝘰𝘮𝘦𝘰𝘯𝘦 𝘪𝘯 𝘺𝘰𝘶𝘳 𝘱𝘰𝘴𝘪𝘵𝘪𝘰𝘯 𝘵𝘰 𝘥𝘰 𝘵𝘩𝘪𝘴. 𝘐𝘵'𝘴 𝘵𝘩𝘦 𝘧𝘪𝘳𝘴𝘵 𝘵𝘶𝘵𝘰𝘳𝘪𝘢𝘭 𝘐 𝘤𝘢𝘯 𝘵𝘩𝘪𝘯𝘬 𝘰𝘧 𝘵𝘩𝘢𝘵'𝘴 𝘢𝘤𝘵𝘶𝘢𝘭𝘭𝘺 𝘴𝘢𝘺𝘪𝘯𝘨 𝘴𝘰𝘮𝘦𝘵𝘩𝘪𝘯𝘨 𝘶𝘴𝘦𝘧𝘶𝘭 𝘢𝘯𝘥 𝘶𝘯𝘣𝘦𝘭𝘪𝘦𝘷𝘢𝘣𝘭𝘦.

𝘔𝘢𝘶𝘳𝘪𝘤𝘪𝘰 𝘏.

𝘠𝘰𝘶 𝘫𝘶𝘴𝘵 𝘨𝘢𝘷𝘦 𝘮𝘦 𝘵𝘩𝘦 𝘧𝘳𝘢𝘮𝘦𝘸𝘰𝘳𝘬 𝘵𝘩𝘢𝘵 𝘐 𝘸𝘢𝘴 𝘮𝘪𝘴𝘴𝘪𝘯𝘨, 𝘢𝘯𝘥 𝘐 𝘥𝘪𝘥𝘯'𝘵 𝘬𝘯𝘰𝘸 𝘵𝘩𝘢𝘵 𝘐 𝘯𝘦𝘦𝘥𝘦𝘥.

𝘊𝘩𝘳𝘪𝘴𝘵𝘺 𝘞.

𝘐 𝘵𝘩𝘰𝘶𝘨𝘩𝘵 𝘵𝘩𝘢𝘵 𝘸𝘢𝘴 𝘨𝘳𝘦𝘢𝘵. 𝘈𝘯𝘥 𝘐 𝘵𝘩𝘪𝘯𝘬 𝘪𝘵'𝘴 𝘴𝘰 𝘧𝘶𝘯𝘯𝘺 𝘣𝘦𝘤𝘢𝘶𝘴𝘦 𝘵𝘰 𝘮𝘦, 𝘐 𝘸𝘪𝘴𝘩 𝘐 𝘩𝘢𝘥 𝘵𝘩𝘪𝘴 𝘱𝘳𝘦𝘴𝘦𝘯𝘵𝘢𝘵𝘪𝘰𝘯 𝘭𝘪𝘬𝘦 𝘧𝘪𝘷𝘦 𝘺𝘦𝘢𝘳𝘴 𝘢𝘨𝘰.

𝘗𝘢𝘴𝘤𝘢𝘭 𝘞.

Tiger21 members have a minimum investable net worth of $20M.

𝗛𝗲𝗿𝗲'𝘀 𝗵𝗼𝘄 𝘁𝗵𝗲𝘆 𝗮𝗹𝗹𝗼𝗰𝗮𝘁𝗲 𝘁𝗵𝗲𝗶𝗿 𝘄𝗲𝗮𝗹𝘁𝗵...

30% Private Equity
25% Real Estate
15% Private Credit
20% Public Equities
10% Other

Notice what's missing? 

The standard 60/40 portfolio your advisor keeps recommending.

The ultra-wealthy don't build portfolios to track the market. 

They build portfolios to 𝗴𝗲𝗻𝗲𝗿𝗮𝘁𝗲 𝗶𝗻𝗰𝗼𝗺𝗲.

And when you model it out, the math is compelling.

If you allocate $3M of your portfolio to income-focused investments there is a clear path to $250K+ in yearly portfolio income.

The opportunities for tax optimization are significant.

And when we apply them, effective rates of 3-5% aren't unrealistic.

That's ~$240K after tax -- with principal intact.

Compare that to the traditional drawdown approach: 

$120K gross, $90K after tax
(and your principal shrinks every year)

Same $3M starting point-- radically different outcome.

The difference isn't access. 

You've been legally qualified to invest in these assets for years. 

The difference is 𝘪𝘯𝘧𝘳𝘢𝘴𝘵𝘳𝘶𝘤𝘵𝘶𝘳𝘦.

Four pillars have to work together: 
- asset selection
- tax optimization
- risk management
- operational cadence

Miss one, the system breaks.

This is what we teach at WealthOps — how to build the infrastructure that makes this possible.

In a few days, I'm hosting a live workshop on how to architect the foundation of your own Micro Family Office.

𝗬𝗼𝘂 𝗰𝗮𝗻 𝗿𝗲𝗴𝗶𝘀𝘁𝗲𝗿 𝗵𝗲𝗿𝗲: https://dub.sh/mN0g8tK

Here is what attendees from last month's workshop said about it:

𝘐 𝘵𝘩𝘰𝘶𝘨𝘩𝘵 𝘵𝘩𝘢𝘵 𝘸𝘢𝘴 𝘨𝘳𝘦𝘢𝘵. 𝘈𝘯𝘥 𝘐 𝘵𝘩𝘪𝘯𝘬 𝘪𝘵'𝘴 𝘴𝘰 𝘧𝘶𝘯𝘯𝘺 𝘣𝘦𝘤𝘢𝘶𝘴𝘦 𝘵𝘰 𝘮𝘦, 𝘐 𝘸𝘪𝘴𝘩 𝘐 𝘩𝘢𝘥 𝘵𝘩𝘪𝘴 𝘱𝘳𝘦𝘴𝘦𝘯𝘵𝘢𝘵𝘪𝘰𝘯 𝘭𝘪𝘬𝘦 𝘧𝘪𝘷𝘦 𝘺𝘦𝘢𝘳𝘴 𝘢𝘨𝘰.
- 𝗣𝗮𝘀𝗰𝗮𝗹 𝗪.

𝘠𝘰𝘶 𝘫𝘶𝘴𝘵 𝘨𝘢𝘷𝘦 𝘮𝘦 𝘵𝘩𝘦 𝘧𝘳𝘢𝘮𝘦𝘸𝘰𝘳𝘬 𝘵𝘩𝘢𝘵 𝘐 𝘸𝘢𝘴 𝘮𝘪𝘴𝘴𝘪𝘯𝘨, 𝘢𝘯𝘥 𝘐 𝘥𝘪𝘥𝘯'𝘵 𝘬𝘯𝘰𝘸 𝘵𝘩𝘢𝘵 𝘐 𝘯𝘦𝘦𝘥𝘦𝘥.
- 𝗖𝗵𝗿𝗶𝘀𝘁𝘆 𝗪.

Tech Careers & Money Talk

𝗪𝗮𝗻𝘁 𝘁𝗼 𝗮𝗰𝗰𝗲𝗹𝗲𝗿𝗮𝘁𝗲 𝘆𝗼𝘂𝗿 𝗙𝗶𝗻𝗮𝗻𝗰𝗶𝗮𝗹 𝗜𝗻𝗱𝗲𝗽𝗲𝗻𝗱𝗲𝗻𝗰𝗲?💸

Join here 👉 techcareersandmoneytalk.com

Tweet Follow-up

Even Justin Welsh chimed in: https://twitter.com/thejustinwelsh/status/1628168298947919878?s=20

Post Follow Up

On the off chance you *do* want financial freedom — do these 11 things instead. 👇

- Ignore the above
- Buy back your time
- Start investing today
- Build a simple budget
- Learn personal finance
- Destroy credit card debt
- Work for equity AND salary
- Diversify w/ passive income
- Align your finances with goals
- Build a team of financial experts
- Join techcareersandmoneytalk.com

What did I miss?

50 - 50 Link

🧠 - Bonus Tip:  For Monday - Do A Brain Dump to Prevent Overwhelm 

Monday means mental overwhelm for Many. 

Objects in your head can be more stressful than they appear! 

Take piece of paper, 10 min and write down all the things you need to get done, work, life etc. 

Once you see them written down identify 3 things that have to get done today. 

Get to your base! 

TCMT Pod Page

𝗟𝗶𝘀𝘁𝗲𝗻 + 𝗦𝘂𝗯𝘀𝗰𝗿𝗶𝗯𝗲 𝘁𝗼 𝗠𝘆 𝗣𝗼𝗱𝗰𝗮𝘀𝘁 👇

🎧 Tech Careers & Money Talk 💸

www.podpage.com/tech-careers-and-money-talk-1/

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Actionable tips for growing your career, building wealth and living a life of impact. 
Always 3 minutes or less.

https://www.techcareersandmoneynews.com/

Find Rest 

🧠 - Bonus Tip:  Your Momentum is Fuel for your Mentors.  As your mentor sees you taking their input and iterating, they will be excited and want to participate more.  

Momentum breeds momentum.   

Hindi Video

Want all the details?   

Check out my origin story here on Audio : https://bit.ly/cnoriginstory

Watch it on YouTube! : https://youtu.be/7Hw-Y2hDtF8


From Equity to Exit 

Momentum for Mentors

wealthward-capital

tech-careers-and-money-talk

careercadre

MC Hammer made $33 million in 1991 alone.
By 1996, he was bankrupt.
𝗛𝗲𝗿𝗲'𝘀 𝘁𝗵𝗲 𝘄𝗶𝗹𝗱 𝘁𝗵𝗶𝗻𝗴𝘀 𝘄𝗲 𝘀𝗽𝗲𝗻𝘁 𝘁𝗵𝗲 𝗺𝗼𝗻𝗲𝘆 𝗼𝗻:

- Helicopter
- Private jet
- 17 luxury cars
- 21 racehorses (some valued at $1 million each)
- Staff of 200 people ($500,000-$1,000,000 per month)
- 40,000 sq ft mansion in Fremont, CA ($12 million purchase)
- Mansion renovations ($30 million+):
->-> Gold toilets
->-> Gold hot tub
->-> Gold-plated front gates inscribed with "HAMMER TIME"
->-> Pool shaped like his parachute pants
->-> Marble statues of himself
->-> Italian marble floors
->-> Bowling alley
->-> 17-car garage
->-> Tennis courts
->-> Two swimming pools
->-> Recording studio
->-> Basketball court

Within 5 years of his peak, he filed for Chapter 11 bankruptcy.

𝗔𝘀𝘀𝗲𝘁𝘀: $9.6 million. 
𝗗𝗲𝗯𝘁𝘀: $13.7 million.

Most people see this list and think the problem was the gold toilets.

The real problem? 𝘕𝘰 𝘴𝘺𝘴𝘵𝘦𝘮𝘴. 𝘕𝘰 𝘭𝘰𝘯𝘨-𝘵𝘦𝘳𝘮 𝘷𝘪𝘴𝘪𝘰𝘯.

Now, I know you're not buying gold toilets. 

But if you're sitting on $1-30 million without systematic wealth operations, you're making the same mistake at a different scale.

Building wealth and preserving wealth require completely different systems.

The wealth you earned doesn't come with the frameworks to protect it. 

That's what separates people who stay wealthy from people who rebuild from zero.

Hammer eventually recovered as a tech investor.

Early positions in Twitter and Square were his saving grace.

𝗖𝘂𝗿𝗿𝗲𝗻𝘁 𝗻𝗲𝘁 𝘄𝗼𝗿𝘁𝗵: ~$2 million.

But he had to start over.

The whole point of building wealth is so you don't have to.

In a few days, I'm hosting a live workshop on how to architect your own Micro Family Office.

𝗬𝗼𝘂 𝗰𝗮𝗻 𝗿𝗲𝗴𝗶𝘀𝘁𝗲𝗿 𝗵𝗲𝗿𝗲: https://dub.sh/mN0g8tK

Here is what attendees from last month's workshop said about it:

𝘐𝘵 𝘸𝘢𝘴 𝘳𝘦𝘢𝘭𝘭𝘺 𝘴𝘵𝘳𝘢𝘯𝘨𝘦 𝘵𝘰 𝘧𝘪𝘯𝘥 𝘴𝘰𝘮𝘦𝘰𝘯𝘦 𝘪𝘯 𝘺𝘰𝘶𝘳 𝘱𝘰𝘴𝘪𝘵𝘪𝘰𝘯 𝘵𝘰 𝘥𝘰 𝘵𝘩𝘪𝘴. 𝘐𝘵'𝘴 𝘵𝘩𝘦 𝘧𝘪𝘳𝘴𝘵 𝘵𝘶𝘵𝘰𝘳𝘪𝘢𝘭 𝘐 𝘤𝘢𝘯 𝘵𝘩𝘪𝘯𝘬 𝘰𝘧 𝘵𝘩𝘢𝘵'𝘴 𝘢𝘤𝘵𝘶𝘢𝘭𝘭𝘺 𝘴𝘢𝘺𝘪𝘯𝘨 𝘴𝘰𝘮𝘦𝘵𝘩𝘪𝘯𝘨 𝘶𝘴𝘦𝘧𝘶𝘭 𝘢𝘯𝘥 𝘶𝘯𝘣𝘦𝘭𝘪𝘦𝘷𝘢𝘣𝘭𝘦.
— 𝘔𝘢𝘶𝘳𝘪𝘤𝘪𝘰 𝘏.

𝘠𝘰𝘶 𝘫𝘶𝘴𝘵 𝘨𝘢𝘷𝘦 𝘮𝘦 𝘵𝘩𝘦 𝘧𝘳𝘢𝘮𝘦𝘸𝘰𝘳𝘬 𝘵𝘩𝘢𝘵 𝘐 𝘸𝘢𝘴 𝘮𝘪𝘴𝘴𝘪𝘯𝘨, 𝘢𝘯𝘥 𝘐 𝘥𝘪𝘥𝘯'𝘵 𝘬𝘯𝘰𝘸 𝘵𝘩𝘢𝘵 𝘐 𝘯𝘦𝘦𝘥𝘦𝘥.
— 𝘊𝘩𝘳𝘪𝘴𝘵𝘺 𝘞.

𝘐 𝘵𝘩𝘰𝘶𝘨𝘩𝘵 𝘵𝘩𝘢𝘵 𝘸𝘢𝘴 𝘨𝘳𝘦𝘢𝘵. 𝘈𝘯𝘥 𝘐 𝘵𝘩𝘪𝘯𝘬 𝘪𝘵'𝘴 𝘴𝘰 𝘧𝘶𝘯𝘯𝘺 𝘣𝘦𝘤𝘢𝘶𝘴𝘦 𝘵𝘰 𝘮𝘦, 𝘐 𝘸𝘪𝘴𝘩 𝘐 𝘩𝘢𝘥 𝘵𝘩𝘪𝘴 𝘱𝘳𝘦𝘴𝘦𝘯𝘵𝘢𝘵𝘪𝘰𝘯 𝘭𝘪𝘬𝘦 𝘧𝘪𝘷𝘦 𝘺𝘦𝘢𝘳𝘴 𝘢𝘨𝘰.
— 𝘗𝘢𝘴𝘤𝘢𝘭 𝘞.

Johnny Depp earned $650 million between 1999-2016.
By 2016, he was on the brink of bankruptcy.
𝗛𝗲𝗿𝗲'𝘀 𝘁𝗵𝗲 𝗰𝗿𝗮𝘇𝘆 𝘁𝗵𝗶𝗻𝗴𝘀 𝗵𝗲 𝘄𝗮𝘀𝘁𝗲𝗱 𝗶𝘁 𝗼𝗻:

- 45 luxury vehicles
- Art collection ($75 million)
- Five LA penthouses ($7.2 million)
- Wine collection ($30,000+ per month)
- 41-acre Kentucky estate for his mother
- Hunter S. Thompson memorial (5 million)
- Private island in the Bahamas ($3.6 million)
- 14 homes around the world ($75 million total)
- Full-time staff of 40 people ($300,000/month)
- Luxury yacht ($18 million, later sold to JK Rowling)
- Entire village in France (church, restaurant, multiple houses)
- Private jet ($11-14 million, plus $200K/month operating costs)

𝗛𝗶𝘀 𝗺𝗼𝗻𝘁𝗵𝗹𝘆 𝗯𝘂𝗿𝗻 𝗿𝗮𝘁𝗲: $𝟮 𝗺𝗶𝗹𝗹𝗶𝗼𝗻.

Most people see this list and think the problem was excess.

The real problem was the system.

He had no operational framework for wealth. 

Multiple managers handling pieces of the puzzle with nobody orchestrating the whole. 

He was making money at the highest level while operating wealth like a Fortune 500 with no CFO.

Now, maybe you're not spending $18 million on yachts. 

But if you're a first-gen wealth builder sitting on $1-30 million without a systematic approach to managing it, you're facing the same structural problem at a different scale.

The wealth you built through earning doesn't automatically come with the systems to preserve it.

- Entity structures that creates tax efficiency. 
- Deduction stacking that optimizes operational expenses. 
- Income architecture that generates consistent cash flow.

The frameworks that prevent lifestyle creep aren't about restricting spending.

They're about building visibility and intentionality into every dollar that flows through your wealth operations.

Rango eventually landed on his feet through continued work and a $20 million Dior deal. 

𝗖𝘂𝗿𝗿𝗲𝗻𝘁 𝗻𝗲𝘁 𝘄𝗼𝗿𝘁𝗵: ~$150 million.

But he had to keep working to recover.

The whole point of building wealth is so you don't have to. 

(hopefully the wine was good)

---

In a few days, I'm hosting a live workshop on how to architect your own Micro Family Office.

𝗬𝗼𝘂 𝗰𝗮𝗻 𝗿𝗲𝗴𝗶𝘀𝘁𝗲𝗿 𝗵𝗲𝗿𝗲: https://dub.sh/mN0g8tK

Here is what attendees from last month's workshop said about it:

𝘠𝘰𝘶 𝘫𝘶𝘴𝘵 𝘨𝘢𝘷𝘦 𝘮𝘦 𝘵𝘩𝘦 𝘧𝘳𝘢𝘮𝘦𝘸𝘰𝘳𝘬 𝘵𝘩𝘢𝘵 𝘐 𝘸𝘢𝘴 𝘮𝘪𝘴𝘴𝘪𝘯𝘨, 𝘢𝘯𝘥 𝘐 𝘥𝘪𝘥𝘯'𝘵 𝘬𝘯𝘰𝘸 𝘵𝘩𝘢𝘵 𝘐 𝘯𝘦𝘦𝘥𝘦𝘥.
— 𝘊𝘩𝘳𝘪𝘴𝘵𝘺 𝘞.

𝘐 𝘵𝘩𝘰𝘶𝘨𝘩𝘵 𝘵𝘩𝘢𝘵 𝘸𝘢𝘴 𝘨𝘳𝘦𝘢𝘵. 𝘈𝘯𝘥 𝘐 𝘵𝘩𝘪𝘯𝘬 𝘪𝘵'𝘴 𝘴𝘰 𝘧𝘶𝘯𝘯𝘺 𝘣𝘦𝘤𝘢𝘶𝘴𝘦 𝘵𝘰 𝘮𝘦, 𝘐 𝘸𝘪𝘴𝘩 𝘐 𝘩𝘢𝘥 𝘵𝘩𝘪𝘴 𝘱𝘳𝘦𝘴𝘦𝘯𝘵𝘢𝘵𝘪𝘰𝘯 𝘭𝘪𝘬𝘦 𝘧𝘪𝘷𝘦 𝘺𝘦𝘢𝘳𝘴 𝘢𝘨𝘰.
— 𝘗𝘢𝘴𝘤𝘢𝘭 𝘞.

Excited to be sitting down with Pascal Wagner next week at the Best Ever Conference to discuss all things Micro Family Office. 

Anyone in my network going to be there?

I help accredited investors build predictable passive income with private deals | LP investor ($3.3M in 20+ deals) | Ex-VC @Techstars (Deployed $150M) | Get My Free Starter Kit👇

Headed to Salt Lake City next week for the 10th Annual Best Ever Conference.

If you’re an LP (or want to be) and you’re tired of “trust me bro” underwriting, I’ve got 2 sessions you might care about:

🎙️ Mainstage Workshop – Tuesday Morning

Before You Wire: The LP’s 3-Step System for Vetting Deals & Operators
I’ll walk through the exact process I use before wiring my own money:

→ How to quickly filter deals so you’re not drowning in pitch decks
→ What actually matters in an operator’s track record and structure
→ The red flags that tell you to walk away, even when the story sounds great

🔥 Mainstage Fireside Chat – Micro Family Offices

I’ll also be doing a fireside chat with Christopher Nelson on building a micro family office:

→ How business owners can think like a family office before a big exit
→ Coordinating tax, cashflow, and private deals
→ Why he built a mastermind around this and what he’s seeing from serious operators and LPs

I’ll be in Salt Lake City Feb 17–20.

If you’re going to be there, comment “BEC” or send me a DM and I’ll mark your name down so we can connect in person.

Would love to meet more serious LPs, operators, and advisors who actually care about doing good deals, not just doing more deals.

Your advisor calls it "portfolio management."

I call it what it is: 𝘄𝗲𝗮𝗹𝘁𝗵 𝘀𝘁𝗼𝗿𝗮𝗴𝗲.

In a traditional drawdown portfolio...

You accumulate. 
You store. 
You withdraw. 
You deplete.

That's not a strategy. 
That's a countdown.

But ultra-high-net-worth families operate differently.

They don't store wealth. 

They build wealth businesses around it.

They build businesses that generate income.

They optimize for structured alpha, not just capital gains.

They transfer operating companies, not just account balances.

This isn't about portfolio size. 
It's about operational mindset.

The chart breaks down the 9 dimensions where these two approaches diverge.

- One side is designed for 𝗱𝗲𝗽𝗹𝗲𝘁𝗶𝗼𝗻.

- The other is designed for 𝗽𝗲𝗿𝗽𝗲𝘁𝘂𝗮𝗹 𝗼𝗽𝗲𝗿𝗮𝘁𝗶𝗼𝗻.

Most people in the $1M-$30M range are stuck in the storage model because that's all the industry offers.

You're too sophisticated for a robo-advisor but too small for a multi family office. 

𝘛𝘩𝘢𝘵'𝘴 𝘵𝘩𝘦 𝘴𝘦𝘳𝘷𝘪𝘤𝘦 𝘥𝘦𝘴𝘦𝘳𝘵.

And it's why we built the 𝗠𝗶𝗰𝗿𝗼 𝗙𝗮𝗺𝗶𝗹𝘆 𝗢𝗳𝗳𝗶𝗰𝗲 framework.

In a few days, I'm hosting a live workshop on how to architect your own Micro Family Office.

𝗬𝗼𝘂 𝗰𝗮𝗻 𝗿𝗲𝗴𝗶𝘀𝘁𝗲𝗿 𝗵𝗲𝗿𝗲: https://dub.sh/mN0g8tK

Here is what attendees from last month's workshop said about it:

𝘐𝘵 𝘸𝘢𝘴 𝘳𝘦𝘢𝘭𝘭𝘺 𝘴𝘵𝘳𝘢𝘯𝘨𝘦 𝘵𝘰 𝘧𝘪𝘯𝘥 𝘴𝘰𝘮𝘦𝘰𝘯𝘦 𝘪𝘯 𝘺𝘰𝘶𝘳 𝘱𝘰𝘴𝘪𝘵𝘪𝘰𝘯 𝘵𝘰 𝘥𝘰 𝘵𝘩𝘪𝘴. 𝘐𝘵'𝘴 𝘵𝘩𝘦 𝘧𝘪𝘳𝘴𝘵 𝘵𝘶𝘵𝘰𝘳𝘪𝘢𝘭 𝘐 𝘤𝘢𝘯 𝘵𝘩𝘪𝘯𝘬 𝘰𝘧 𝘵𝘩𝘢𝘵'𝘴 𝘢𝘤𝘵𝘶𝘢𝘭𝘭𝘺 𝘴𝘢𝘺𝘪𝘯𝘨 𝘴𝘰𝘮𝘦𝘵𝘩𝘪𝘯𝘨 𝘶𝘴𝘦𝘧𝘶𝘭 𝘢𝘯𝘥 𝘶𝘯𝘣𝘦𝘭𝘪𝘦𝘷𝘢𝘣𝘭𝘦.
𝗠𝗮𝘂𝗿í𝗰𝗶𝗼 𝗛.

𝘠𝘰𝘶 𝘫𝘶𝘴𝘵 𝘨𝘢𝘷𝘦 𝘮𝘦 𝘵𝘩𝘦 𝘧𝘳𝘢𝘮𝘦𝘸𝘰𝘳𝘬 𝘵𝘩𝘢𝘵 𝘐 𝘸𝘢𝘴 𝘮𝘪𝘴𝘴𝘪𝘯𝘨, 𝘢𝘯𝘥 𝘐 𝘥𝘪𝘥𝘯'𝘵 𝘬𝘯𝘰𝘸 𝘵𝘩𝘢𝘵 𝘐 𝘯𝘦𝘦𝘥𝘦𝘥.
𝗖𝗵𝗿𝗶𝘀𝘁𝘆 𝗪.

𝘐 𝘵𝘩𝘰𝘶𝘨𝘩𝘵 𝘵𝘩𝘢𝘵 𝘸𝘢𝘴 𝘨𝘳𝘦𝘢𝘵. 𝘈𝘯𝘥 𝘐 𝘵𝘩𝘪𝘯𝘬 𝘪𝘵'𝘴 𝘴𝘰 𝘧𝘶𝘯𝘯𝘺 𝘣𝘦𝘤𝘢𝘶𝘴𝘦 𝘵𝘰 𝘮𝘦, 𝘐 𝘸𝘪𝘴𝘩 𝘐 𝘩𝘢𝘥 𝘵𝘩𝘪𝘴 𝘱𝘳𝘦𝘴𝘦𝘯𝘵𝘢𝘵𝘪𝘰𝘯 𝘭𝘪𝘬𝘦 𝘧𝘪𝘷𝘦 𝘺𝘦𝘢𝘳𝘴 𝘢𝘨𝘰.
𝗣𝗮𝘀𝗰𝗮𝗹 𝗪.

𝗬𝗼𝘂𝗿 𝗽𝗼𝗿𝘁𝗳𝗼𝗹𝗶𝗼 𝗶𝘀 𝗴𝗲𝗻𝗲𝗿𝗮𝘁𝗶𝗻𝗴 𝘁𝗵𝗲 𝘄𝗿𝗼𝗻𝗴 𝗶𝗻𝗰𝗼𝗺𝗲.
Same $100K of investment returns.
One person pays $10K in taxes. Another pays $37K.

The difference isn't luck. 
It's not tax evasion. 
It's income architecture.

Most investors build portfolios backwards. 

They pick assets they like, then deal with whatever income those assets generate. Dividends. Interest. Short-term gains. Whatever shows up on the 1099.

That's 𝘳𝘦𝘢𝘤𝘵𝘪𝘷𝘦 wealth management.

Here's what changes when you architect income systematically:

You start with the tax outcome you want. 

Then you structure your portfolio to generate that type of income.

Here are some examples of tax-efficient income:

 • Long-Term Capital Gains (0-20% + timing control)
 • Qualified Dividends (0-20% vs 37% ordinary rates)
 • Return of Capital (reduces basis, defers tax indefinitely)
 • K-1 Depreciation (offsets other income, creates real cash)

Compared to tax-inefficient income:

 • Ordinary Interest (taxed at full 37% marginal)
 • Non-Qualified Dividends (no preferential rate)
 • Short-Term Gains (ordinary income, no deferral)
 • Traditional IRA Withdrawals (100% ordinary + RMD penalties)

Same $100K income. 
$10K in taxes or $37K in taxes.

Your portfolio structure determines which types you generate.

This is what I call Game 1: Income Architecture. 

It's the foundation of systematic wealth management. You're not just picking investments—you're designing income at the source.

When you understand this, you stop accepting whatever income your portfolio happens to generate. 

And you start building a portfolio that produces the right types of income for your tax situation.

That's the shift from 𝗠𝗼𝗻𝗲𝘆 𝗠𝗮𝗸𝗲𝗿 to 𝗠𝗼𝗻𝗲𝘆 𝗠𝗮𝗻𝗮𝗴𝗲𝗿.

In a few days, I'm hosting a live workshop where we break down the complete framework for architecting your Micro Family Office.

𝗬𝗼𝘂 𝗰𝗮𝗻 𝗿𝗲𝗴𝗶𝘀𝘁𝗲𝗿 𝗵𝗲𝗿𝗲: https://dub.sh/mN0g8tK

Here's what attendees from last month said:

𝘐𝘵 𝘸𝘢𝘴 𝘳𝘦𝘢𝘭𝘭𝘺 𝘴𝘵𝘳𝘢𝘯𝘨𝘦 𝘵𝘰 𝘧𝘪𝘯𝘥 𝘴𝘰𝘮𝘦𝘰𝘯𝘦 𝘪𝘯 𝘺𝘰𝘶𝘳 𝘱𝘰𝘴𝘪𝘵𝘪𝘰𝘯 𝘵𝘰 𝘥𝘰 𝘵𝘩𝘪𝘴. 𝘐𝘵'𝘴 𝘵𝘩𝘦 𝘧𝘪𝘳𝘴𝘵 𝘵𝘶𝘵𝘰𝘳𝘪𝘢𝘭 𝘐 𝘤𝘢𝘯 𝘵𝘩𝘪𝘯𝘬 𝘰𝘧 𝘵𝘩𝘢𝘵'𝘴 𝘢𝘤𝘵𝘶𝘢𝘭𝘭𝘺 𝘴𝘢𝘺𝘪𝘯𝘨 𝘴𝘰𝘮𝘦𝘵𝘩𝘪𝘯𝘨 𝘶𝘴𝘦𝘧𝘶𝘭 𝘢𝘯𝘥 𝘶𝘯𝘣𝘦𝘭𝘪𝘦𝘷𝘢𝘣𝘭𝘦.

𝘔𝘢𝘶𝘳𝘪𝘤𝘪𝘰 𝘏.

𝘠𝘰𝘶 𝘫𝘶𝘴𝘵 𝘨𝘢𝘷𝘦 𝘮𝘦 𝘵𝘩𝘦 𝘧𝘳𝘢𝘮𝘦𝘸𝘰𝘳𝘬 𝘵𝘩𝘢𝘵 𝘐 𝘸𝘢𝘴 𝘮𝘪𝘴𝘴𝘪𝘯𝘨, 𝘢𝘯𝘥 𝘐 𝘥𝘪𝘥𝘯'𝘵 𝘬𝘯𝘰𝘸 𝘵𝘩𝘢𝘵 𝘐 𝘯𝘦𝘦𝘥𝘦𝘥.

𝘊𝘩𝘳𝘪𝘴𝘵𝘺 𝘞.

𝘐 𝘵𝘩𝘰𝘶𝘨𝘩𝘵 𝘵𝘩𝘢𝘵 𝘸𝘢𝘴 𝘨𝘳𝘦𝘢𝘵. 𝘈𝘯𝘥 𝘐 𝘵𝘩𝘪𝘯𝘬 𝘪𝘵'𝘴 𝘴𝘰 𝘧𝘶𝘯𝘯𝘺 𝘣𝘦𝘤𝘢𝘶𝘴𝘦 𝘵𝘰 𝘮𝘦, 𝘐 𝘸𝘪𝘴𝘩 𝘐 𝘩𝘢𝘥 𝘵𝘩𝘪𝘴 𝘱𝘳𝘦𝘴𝘦𝘯𝘵𝘢𝘵𝘪𝘰𝘯 𝘭𝘪𝘬𝘦 𝘧𝘪𝘷𝘦 𝘺𝘦𝘢𝘳𝘴 𝘢𝘨𝘰.

𝘗𝘢𝘴𝘤𝘢𝘭 𝘞.

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The Battle

Maya Grossman

Christopher Nelson

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taplio

The Battle

Maya Grossman

Christopher Nelson

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Posts

Engagements

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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);}Maya Grossman's LinkedIn Performance

Performance ScoreChristopher Nelson's LinkedIn Performance

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Performance ScoreMaya Grossman's LinkedIn Performance