Will Montague

What I post is my opinion and not my employer's.

[Will Montague @PathTo99th]

Pick Your Game Early. Be Humble About How You Win It.

I just listened to an episode of the The Interview (from The New York Times) titled “Simon Cowell Is Sorry, Softer and Grieving Liam Payne”. I highly recommend you check it out.

Simon Cowell knew he wanted to be in music earlier in his life than most people start thinking about how to get their first internship. Not long after, he found himself in financial ruin, and have to move back in with his parents. Things were bumpy for a while as he even when he started signing acts, the industry openly mocked him. But eventually, things finally started to work.

Because he stopped caring about looking smart.

He stopped chasing credibility.
He chased survival.
He chased whatever kept him in the room long enough to build real judgment.
Robson and Jerome.
Wrestlers.
Cartoon soundtracks. 

The “uncool” stuff that kept the lights on.

That shift is the part young advisors never hear about.

Many aspiring wealth advisors are fixated on finding the perfect lane. They want a role that gives them optionality. They want clients who make you feel important. They want the path to also look good on LinkedIn so their peers think they’re “moving up.”

The job early on is none of that.

The job is to pick a game you can play for 30 years and then get humble about how you earn your reps. The job is eating dirt until your instincts sharpen. The job is staying in the arena long enough to earn the judgment that multi-generational families actually hire.

Try this:

Pick your game. Multi-gen families, business owners, AM Law 100 lawyers, whatever. Stop hedging.

Say yes to the unglamorous work. Small accounts. Complicated family dynamics. Administrative cleanup. That is where judgment gets built.

Get fifty reps. Stop waiting for the one “high-profile” opportunity that almost never arrives.

Check your ego. If Cowell could sign Robson and Jerome, you can pick up the phone when a client’s son wants to talk about his Roth IRA.

Stay in the room. Most people quit before their talent compounds.
The advisors who eventually lead the most complex client engagements are usually not the ones who looked impressive at 28. They’re the ones who refused to leave the game at 38.

So be honest with yourself. What game are you actually trying to win, and what are you willing to do to stay in it?

[Will Montague @PathTo99th]

For anyone who wants to dig into the underlying data, here are the primary sources behind the stats in this post.

Sources

1. Growth in $30M+ segment (6.2% in 2024)
Capgemini Research Institute, World Wealth Report 2025 – global HNWI trends and ultra-high-net-worth (UHNW) population growth; UHNW individuals grew by 6.2% in 2024.

https://t.co/aUCFdAyTh8

Press release summary:

https://t.co/Ux00Ayxpy7

2. Advisor-managed HNW assets projected to surpass $30T by 2028, growing ~9.3% annually
Cerulli Associates, “Client Service Offerings Will Be Key Differentiator for HNW and UHNW Practices” (Aug 26, 2025) – projects the total advisor-managed high-net-worth (HNW) industry will exceed $30 trillion AUM by 2028 at roughly 9.3% annual growth.

https://t.co/uIQpi9rR8m

3. $124T wealth transfer in the U.S. through 2048
Cerulli Associates, “Cerulli Anticipates $124 Trillion in Wealth Will Transfer Through 2048” – U.S. wealth transfer estimate through 2048 (The Cerulli Report — U.S. High-Net-Worth and Ultra-High-Net-Worth Markets 2024).

https://t.co/Yq97aIOS6V

4. Global asset management AUM at ~$128T
Boston Consulting Group, Global Asset Management 2025: From Recovery to Reinvention – global asset management industry AUM reached about $128 trillion in 2024.
Press summary:

https://t.co/IYKOoB59io

5. Wealth concentration at the top end (context for ~$100–120T figure)
UBS, Global Wealth Report 2025 – analysis of global personal wealth distribution, including very-high-net-worth segments that anchor the ~$100–120 trillion estimate for wealth held by the top tiers.

https://t.co/R0ufHjx9Tk

[Will Montague @PathTo99th]

The segment of global wealth management serving ultra-high-net-worth families is on fire.

Some stats that every early career advisor should take note of:

* The global population of individuals with $30 million or more in assets grew by 6.2% in 2024.

* Advisor-managed assets for high-net-worth clients with $5 million or more are projected to surpass $30 trillion by 2028, compounding at 9.3% per year.

* In the United States alone, around $124 trillion is expected to change hands in the great wealth transfer by 2048.

***

But you do not really see how fast the opportunity set is shifting until you break these down.

1. The number of $30 million plus individuals grew by 6.2% in a single year

That is impressive on its own.

What matters more is the scale of wealth now concentrated in this group. Depending on the definition and data source you use, individuals with $30 million or more control on the order of ~ $60 trillion in wealth worldwide.

If you are an ambitious associate, it is plain to see where gravity is pulling the brightest career opportunities in this business.

2. Advisor-managed assets for wealthy families are growing at 9.3% a year

Advisor-managed assets for U.S.-based high-net-worth households with $5 million or more, including today’s $30 million plus families and those most likely to join them, are projected to surpass $30 trillion by 2028.

At that pace, the pool roughly doubles in about eight years.

The last time the industry saw compounding like that at scale was in fintech in the mid-2010s, when a handful of players used a structural shift to become category owners. The same thing will happen here. A small subset of advisory firms will learn how to serve first-generation and inheriting families facing a very specific set of opportunities and threats. These firms and their lead advisors will not be easily displaced.

3. The $124 trillion wealth transfer

That number is so large that it is abstract until it is put into context.

In the United States alone, $124 trillion moving between now and 2048 is on the order of buying every residential home in the country twice. Or giving roughly $15,000 to every person on the planet.

That capital will either be well advised or it will not. It will not sit in a vacuum.

My guess?

Wealth management is on track to sit beside global retail banking in revenue and influence, much the same way it has already outgrown old-line insurance brokerage in many markets. If current growth holds, that shift is a 2030s story, not a distant future one.

If you are in your twenties or early thirties and anywhere near this industry, that is your window.

The only real question is whether you play a role supporting other advisors when the wave crests, or you are the person that the family calls first.

[Will Montague @PathTo99th]

Good advisors grab the fire extinguisher.

Great advisors let it burn long enough to find the source.

Here's the trap: A client shows up with a painful tax bill or a cash crunch. The instinct is to fix it immediately. But when you numb the pain too fast, you kill the feedback loop. The lesson never lands. The behavior never changes.

That's how "good" advice becomes a time bomb.

Consider the dynasty trust that saved 40% in estate taxes and destroyed a family. The heirs spent years begging a corporate trustee for distributions. The math was perfect. The relationships were rubble.

I've seen liquidity 'save' a business owner from a cash crunch--and block the hard pivot that would've actually saved the company.

The pattern is the same:
Solve today's pain.
Create tomorrow's monster.

Before you accept any fix, ask one question:

What second-order behavior does this solution create in 10 years?

If the answer makes you uncomfortable, the plan isn't ready.

[Will Montague @PathTo99th]

You Can Stand by a Decision and Still Owe Someone an Apology

That distinction took me years to learn.

Early in my career, when a colleague felt wronged by something I'd done, my instinct was to defend the decision.

Here's why I made that call.
Here's what you're not seeing.
Here's why, if I had to do it again, I'd do the same thing.

I was usually right about the decision. And I was almost always wrong about what the conversation actually needed.

Because the person across from me wasn't asking me to admit I was wrong. They were asking me to acknowledge that something I did, even something defensible, cost them something.

Time.
Trust.
Face.
Peace of mind.

The apology that actually repairs things sounds like:
"I'm sorry I put you in that position. You deserved better communication from me."

You're not apologizing for your judgment. You're apologizing for the experience.

That's not weakness. That's the kind of self-awareness that makes a client or a colleague think, "This is someone I can be honest with when something goes wrong." With multi-generational families, with real complexity and long memories, that's everything. They don't stay with you for decades because nothing ever went sideways. They stay because of how you handled it when it did.

One caveat: this only works if you mean it. A hollow apology, one you offer just to smooth things over or make yourself feel better, does more damage than silence.

But if you're genuinely willing to hear their perspective and own your part without defending yourself?

Sit down.

Have the conversation.

Say the words.

[Will Montague @PathTo99th]

Every Sunday after church, I walk into the Red Dragon with Roy to help coach about twenty junior players.

The room fills up fast.

Some kids have never held a cue. Some were taught a few things by a parent. Some are somewhere in the middle.

There’s one kid I’ve been watching for months.

His bridge hand is always turned backward. Roy and I have both corrected it again and again. When I walk by, I’ll say, “Still backwards.” He smiles, shrugs, and keeps shooting.

He’s not disrespectful.
He’s not defiant.
He just believes his version is good enough.

And as a result, his progress moves inch by inch.

Then there was a kid who walked in about six weeks ago with a stroke that was completely broken.

No foundation.
No stability.
Nothing about it lined up.

But he listened.

Every correction, he tried. Every drill, he worked at. He practiced on his own during the week, and you could see it the moment he walked back in. Today he’s competing with players who have been here for years. His progress is real, and everyone in the room can feel it.

Same environment.
Same coaches.
Very different trajectories.

That’s where the lesson sits for early-career wealth advisors.

A lot of people think their experience is their advantage. Sometimes it is. But just as often, it becomes a set of habits they’re reluctant to let go of. They prepare client meetings the way someone once showed them. They communicate the way a prior manager framed things.

They cling to approaches that feel familiar, even when they’re not effective.

Hiring managers see this more clearly than candidates do. Given the choice between someone with “experience” and someone new who is willing to learn, they often take the person with the cleaner slate. It’s easier to build strong fundamentals than to unwind bad ones.

The advisors who grow the fastest are the ones who can say, “Maybe the way I’ve been doing this isn’t the best way.”

They listen without getting defensive. They try the adjustment before they question it. They stay open enough to let better habits replace weaker ones.

Coachability isn’t passive.
It’s active.
It’s the willingness to set aside what you think you know so you can pick up something better.

Back at the Red Dragon, the kid with the backward bridge is still shooting the way he arrived. The kid who showed up with a broken stroke is now pushing the more experienced players.

And it has nothing to do with talent.

It’s the difference between holding on and letting go.

[Will Montague @PathTo99th]

Ego is useful.
Until it starts using you.
Lead with it when conviction matters.
Set it down when listening matters more.

[Will Montague @PathTo99th]

The Most Practical Career Advice I Know

A lot of people in their twenties and early thirties feel the same quiet frustration.

They're capable of more. They're not in the right role yet. They can see the path they want, but they don't have the opportunity to step into it.

Here's the truth: You control your decisions. You don't control your opportunity set.

So the practical move is simple.

Wherever you are right now is the perfect place to start.

Not because it's ideal. Because it's real. Because it's what you can influence today.

When I was a bank teller and then a customer service rep, investment banking wasn't an option. It wasn't even possible. But commercial lenders walked through our doors and used our spare offices every week. They were in my orbit. So I learned from them. I asked questions. I showed I was serious. I made it clear that if they ever had an opening, I wanted a shot.

Eventually I got one.

Not because of some brilliant plan. Because I acknowledged my reality and put one foot in front of the other. I worked hard. I showed up well. I asked for advice. I went to grad school at night. I made my intention known to the right people. When the door cracked open, I was ready.

That's the practical path.

If you're not where you want to be:

Pick your head up. Look around. Assess who is in your orbit.

Then show up as the best version of yourself -- pride in your work, energy, humility, curiosity, and a clear desire to grow. When people see that combination, they help you. Opportunity compounds around people who make it obvious they want more.

Career change isn't one big leap. It's a stack of small, intentional steps taken from exactly where you're standing.

Start there.

[Will Montague @PathTo99th]

The Associate's Dilemma: Playing It Safe vs. Making It Count

You volunteered. Congratulations – you’ve cleared the lowest bar in professional life.

Here’s the truth nobody tells junior advisors: raising your hand isn’t the hard part. Showing up isn’t the contribution. The gap between “I’ll help” and actually moving the needle is where careers are made or stalled.

While in sports like pro football, availability may be the most important ability, it pales in comparison to someone who both shows up AND brings utility.

Your calendar says you’re in the meetings.

Your actions between the meetings determine whether your attendance mattered.

I once worked with a finance vet who came up through consulting and some of the most elite firms on Wall Street. His philosophy? It’s infinitely better to grab the bull by the horns and get tripped up stepping on your own toes than it is to sit around waiting for an engraved invitation to act.

You’ll make mistakes.
You’ll draft and send the email wrong.
You’ll schedule the call at an inconvenient time.

As Jocko Willink says, "Good."

That’s data.
That’s movement.

The only unforgivable error is inertia – watching opportunities evaporate because you were too cautious to act.

Being a co-pilot on a project doesn’t mean nodding along in meetings. It means taking the pen. Drafting the memo before you’re asked. Scheduling the follow-up before your boss remembers it needs to happen.

Big wins – the kind that define careers in this business – require big initiative.

They require stick-to-itiveness.
They require what old-school operators call “hutzpah.”

When you sign up for a Big Hairy Audacious Goal, you’re committing to drive the outcome, not just occupy a seat.

Your leadership doesn’t want passengers. They want drivers who occasionally bump into curbs while learning to navigate. So take the risk.
Step on your toes. Own the outcome. 

That’s how you stop being “helpful” and start being indispensable.

[Will Montague @PathTo99th]

Your Managing Director Is Keeping Score. Just Not the One You Think.

You just walked out of a prospect meeting. 

Multigenerational family. $50M+. They're unhappy with their current advisors—too reactive, no one acting as the center of gravity for their financial life.

You're a fourth-year associate. You did everything right. Analyzed the trust structures. Built the deck. Didn't fumble a single technical question.

As you settle into the back of the black car to head to the airport, you turn to your MD and ask: “How did I do?”

What you think you’re asking: “Did I perform well?”

What your MD actually hears: “I need validation for something that’s already over instead of coaching for what comes next.”

That question – “How did I do?” – just told them everything they need to know about whether you think like an analyst or an advisor

Here’s why:

Your MD already knows how you did. They were sitting right next to you.
They know you nailed the technical details. They know the family liked you. They know you didn’t embarrass yourself or the firm. 

That’s Your First Score. It’s already been graded. It’s already in the books. 
Your Second Score is how well you respond to it.

What they’re actually evaluating – what determines whether you’re on the partnership track or plateauing as a senior associate – is your Second Score. 

When you ask “How did I do?” you’re asking your MD to look backward and judge you.

When you ask “What’s the one thing I should do differently next time?” – you’re asking them to look forward and coach you. 

That small shift changes everything. 

It changes you from someone who needs validation into someone who demands growth. 

It changes your MD from a judge to a mentor. 

And it changes the conversation from evaluation (which is uncomfortable and political) to development (which is generous and collaborative). 

The next time you walk out of a client meeting, try this instead:

“I know there’s something I could have done better in there. What’s the one thing I should focus on next time?”

Then shut up and listen. 

Don’t defend. Don’t explain. Don’t rationalize. 

Just absorb it like you’re being handed the blueprint to the next level. 

Because that’s exactly what’s happening. 

Your MD isn’t keeping score on whether you’re good. 

They’re keeping score on whether you’re getting better.

The fastest way to lead your firm’s most strategic engagements isn’t being the best analyst in the room.

It’s being the most relentlessly improvable.

[Will Montague @PathTo99th]

Why I Write About Wealth Advisory

Financial services found me at exactly the right moment.

I needed work. A friend extended a hand. What followed wasn't a straight line (it never is) but with curiosity, consistency, and one deliberate step after another, this path has given me more than I could have imagined: meaningful work, fascinating people, clients I care deeply about, and the ability to provide for my family.

Somewhere along the way, I caught the teaching bug.

Maybe it came from the coaches who stayed late, the bosses who invested time they didn't have, the mentors who saw something in me I couldn't yet see in myself. Whatever the source, I've spent years wanting to do for others what they did for me.

That's what drives this writing.

By sharing what I've learned, I learn it again, both more clearly and more deeply. The lessons that shaped my career are sharpened anew when I put them into words. And if even one of those lessons helps someone else find their footing, accelerate their journey, or see the path ahead with more clarity, then this work matters.

Wealth advisory isn't just lucrative. It's a calling. It's the privilege of guiding families through their most important decisions. It's the craft of mastering complex planning. It's the honor of being trusted with what people have spent lifetimes building.

I want more people to choose this path. Not just for the career, but for what it makes possible:

* service to clients,
* contribution to communities,
* the deep satisfaction that comes from doing hard work well.

If what I share here plays even a small part in helping someone build a rewarding career in this space, then every post is worth it.

That's why I'm here. That's what I hope to accomplish.

[Will Montague @PathTo99th]

I've spent years trying to calibrate this balance.

Too little ego: you disappear when people need you.

Too much: you confuse your authority with your worth.

The people I respect most can hold the tension between confidence and humility.

[Will Montague @PathTo99th]

5 Lessons Advisors Learn When Building a Lasting Advisory Practice

Advisors who want to build something durable (something that matters over decades) tend to learn the same lessons. Often later than they wish.

1. You can’t serve everyone well.
Most of us start broad. It feels practical. But the advisors who gain real traction narrow their focus. Tech founders. PE partners. Multi-generational families.
Specialization doesn’t make your world smaller. It sharpens your judgment. And that judgment compounds.

2. Strong relationships outperform constant activity.
A handful of thoughtful COI (center of influence) relationships will do more for a practice than a year of scattered outreach. One trusted CPA or attorney partner often changes the slope of a career. Growth becomes steadier when referrals come from people who know exactly where you add value.

3. Technical depth is a quiet advantage.
Products are everywhere. True expertise is rare.
Families trust the advisor who understands GRATs, QSBS, liquidity planning, and taxes well enough to see the implications before anyone else does. The people who keep advancing carve out real time for study. It shows in the conversations. That said, you don't have to be the expert in all areas, but you must surround yourself with people who are.

4. Systems protect you from burnout.
No one sustains a serious practice from memory and a crowded inbox.
The advisors who build durable careers put structure in place early: onboarding, review cycles, communication rhythms, delegation. It feels slow at first. Then it becomes the reason clients stay and the work stays manageable.

5. Retention determines the trajectory.
New relationships create momentum. Longstanding ones create stability.
A high retention rate compounds quietly in the background. A low one keeps you rebuilding what you already built.

Bottom line: A meaningful advisory practice isn’t built through force. It’s built through clarity: choosing a focus, deepening relationships, strengthening your craft, and putting systems under the work.
When those pieces are in place, the practice becomes something you can be proud of for a long time.

[Will Montague @PathTo99th]

The hardest part of wealth advice isn't the math.

It is helping clients avoid future regret.

Early-career advisors focus on getting every detail of the analysis right.
Senior advisors focus on something different.
They focus on helping clients make decisions they can live with, especially when the outcome is uncertain.

I once watched a client hedge a concentrated stock position.
The analysis was sound and the risk reduction was clear.
Then the stock tripled.
He didn’t see the protection he gained. He only saw the upside he missed.
The relationship did not survive it, even though the advice was technically correct.

The issue was not the recommendation.
It was not understanding what mattered most to that client.
For him, the discomfort of missing upside was greater than the fear of downside.
The strategy did not match how he saw himself as an investor.

This is why one question separates information from real advice.
“If this outcome disappoints us, what will you tell yourself about why you made this choice?”

Clients who can answer that question usually stay confident in their process.
Clients who cannot almost always end up feeling misled.

Your job is not just to optimize a portfolio.
It is to help clients make decisions they can stand behind, no matter what the market does next.

That is what keeps relationships strong.

[Will Montague @PathTo99th]

The Gift of Proximity

Most early-career professionals don’t realize how rare it is to sit shoulder to shoulder with top-tier excellence.

Early in my own career, I was surrounded by some of the best commercial bankers in New England, the kind of people who could spot a problem in a balance sheet before you’d finished reading the second line. I thought I was giving it my all. In hindsight, I wasn’t. There were more questions I could have asked, and a lot more I could’ve learned just by watching how they made decisions.

Even when you think you’re working hard, it’s worth stepping back and asking if you’re really making the most of what’s in front of you. Talk to people outside your circle. Ask for feedback. Watch how the best prepare, not just how they perform.

Because there are people who would do anything for that kind of access. If you have that seat, hold it like it means something. Otherwise, you’re not just shortchanging yourself; you’re shortchanging your firm too. The person who’s hungry for that seat would bring an energy and attention to detail your team deserves.

Treat proximity to excellence as a responsibility, not a perk.

[Will Montague @PathTo99th]

Your Basic Tasks Carry More Weight Than You Think

Junior advisors often treat core responsibilities like stepping stones to something more interesting. They want special projects without realizing the work already in front of them is where trust is built.

Every task you handle reflects directly on your senior partner.

The families receiving your emails, meeting prep, and follow-up are not thinking about your title. They are thinking about the firm they hired. If the message is unclear, incomplete, or imprecise, it reflects on the senior advisor who put you in a position to represent them.

The family with fifty million dollars on the balance sheet does not know you are early in your career.

They assume the work coming from the firm meets a certain standard. Your job is to uphold it. Most of the time, the difference between a smooth client experience and a concerned phone call comes down to the quality of that day-to-day execution.

This is why senior advisors place so much emphasis on preparation.

It is not because the details are tedious. It is because the details are where problems usually start. The junior who double checks a beneficiary designation, confirms a cost basis, or notices a trust document inconsistency is doing far more than “support work.” They are reducing risk and strengthening the relationship.

Here is the part nobody says out loud.

You earn your real promotion long before the title changes. It happens the moment a senior partner stops wondering if they need to verify your work. When they hand you a client situation and trust that you will handle it correctly, you have moved to a different level. Everything that follows is a formality.

Master the basics.

They are not basic at all.

[Will Montague @PathTo99th]

The hardest questions an advisor faces sound like they’re about money.

They’re really about the people sitting across the table.

Clients aren’t testing your credentials.
Competence is the baseline.
They’re testing your judgment. That is, whether you understand the personal complexities behind the numbers.

Succession. Fairness. Legacy.

Most advisors are comfortable with a balance sheet.
Few are comfortable in the room where unspoken tensions decide what happens next.

Understanding the portfolio is the baseline.
Understanding the people, their history, and their fears is the real work.

It always starts the same way.
With listening.

[Will Montague @PathTo99th]

Why Your Advisor's Ego Matters More Than You Think

Most clients don't want an advisor with a big ego. And they're right to be wary—unchecked arrogance can be expensive.

But they also don't benefit from someone who won't take a position.
Wealth management isn't just asset allocation. It's stewardship under uncertainty. And that requires conviction. The ability to say, "Based on everything I know, here's what I recommend"—and then stand behind it when the headlines get noisy.

Conviction without arrogance is rare. It requires enough ego to trust your judgment, but not so much that you stop listening. It means being confident in your framework while staying humble about what you don't know.

I've learned that my job isn't to be the smartest person in the room. It's to be the clearest. To synthesize complexity into actionable insight. To hold steady when fear is contagious.

That doesn't come from ego as pride. It comes from ego as responsibility.

[Will Montague @PathTo99th]

What sound helps you think clearly?

[Will Montague @PathTo99th]

Some days, focus feels like a fight. Not against the work, but against the noise — both outside and inside your own head.

[Will Montague @PathTo99th]

Focus isn’t built by force. It’s built by tuning the environment until your mind can work uninterrupted.