In 1762, Rousseau wrote:

In 2026, highly educated Gen Zs are experiencing a moment of reckoning.

• AI is cutting 16,000 U.S. jobs a month, with Gen Z taking the brunt;

• Gen Z is the first generation in modern history to be (accused of being!) “cognitively less capable“ than their parents.

By 2030, current family leaders also face a $5.8 trillion dollar challenge.

• Is the family business a legacy to be preserved or an asset to be sold?

• Is purpose worth pursuing at the expense of profit?

• Is a worthy successor present inside the family?

According to Rousseau, the struggle for survival is the ultimate teacher.

For current family leaders, many are concerned with stewarding their family wealth & legacy.

For future family leaders, many are struggling to pursue meaningful careers.

the Totemic thesis

I am someone who has:

• served as an Investment Manager at a single family office and a Manager at a family foundation for the past six years, with both firms established by my family;

• curated a community of 100+ single family office principals, rising gen, and investment professionals for a multi family office, with no relation to my family;

• documented ways of building trust across generations within different family businesses and family offices.

I believe that

• receiving wisely from our current family leaders is increasingly a strategic imperative for our careers;

• giving wisely by our current family leaders is becoming a critical component of their succession planning;

• our goals and those of our families’ may converge in more ways than we expect.

I am very close to announcing to something exciting that I’ve been working on for the better part of this year.

If you are either a current family leader or a future family leader, please reach out. I’d love to get you involved.

values that matter

In September 2025, I played a card game.

I picked the ten values that mattered the most to me.

Here’s how I interpret each value in my own words:

1. Integrity

   • Living truthfully to myself

   • Being capable of being entrusted greatly

2. Self Knowledge

   • Understanding my strengths and weaknesses

   • Uncovering my blindspots, making my unknowns known

3. Communication

   • Listening well

   • Speaking only if my words are true, necessary, and kind1

4. Open Mindedness

   • Staying curious no matter how strong my views are

   • Asking great questions

5. Trust

   • Empowering people near or below me

   • Standing by their decisions even if unpopular

6. Self Respect

   • Knowing my worth

7. Family

   • Expressing love towards those closest around me

8. Faith

   • Cultivating a close relationship with God

   • Discerning my calling

9. Health

   • Preventing chronic illness from hindering my quality of living

10. Belonging

    • Contributing to communities I care about

    • Developing pride for being part of such communities

values that inconvenience

In 2026, it’s not been easy to:

• hold my tongue when I want to be right

• delegate tasks to teammates without intervention

• listen to dissenting views on how I should run my business

• act when I should be learning, or learn when I should be acting

• balance the incessant grind of entrepreneurship against family, faith, and health commitments.

Some days, I feel on top of the world. Most days, I’m just grateful to be alive.

Every day however, I feel at peace.

So long as I am getting better at living in line with my values. One day at a time.

dear reader

What are your values? Do you share any of mine?

Pick one of your values that has inconvenienced you.

How have you benefited as a result?

Subscribe now

We watch for the legendary fights. We weep for the soaring scores.

But have we weighed the cost of their crowns?

Kagaya Ubuyashiki. Itachi Uchiha. Eren Yeager.

Each of them created their own blueprint to build, redeem, or redefine their lineage.

Even if it meant losing themselves.

Kagaya Ubuyashiki (Demon Slayer)

Family Legacy: A multi-generational curse binds the Ubuyashiki bloodline.

• A Nemesis is Born: Over 1,000 years ago, a man called Muzan was born into the wealthy and powerful Ubuyashiki lineage as a weak, terminal human. Doctors predicted he would die before the age of twenty. Stumbling upon a cure for his medical condition, Muzan began to consume human flesh, achieved functional immortality, and spawned legions of demons.

• The Family Business of Slaying Demons: Every male child born to the Ubuyashiki family has since died by the age of 30. A priest told the Ubuyashiki family that the only way to save their bloodline was to dedicate themselves to killing the Demon King they had created. Hence, the Demon Slayer Corps was established to eradicate Muzan and atone for an original Ubuyashiki family sin.

The Blueprint of Succession: Kagaya built the way for his son Kiriya to break the cycle.

• Moral Leadership: Inheriting leadership at age four, Kagaya earned the absolute devotion of the Hashira, the nine elite and battle-hardened warriors who serve as the top-ranking Demon Slayers. He then devised a strategy to trap Muzan by using himself and his wife as bait, consummating his moral fortitude as the ultimate sacrifice.

• Proactive Succession Planning: When he died in the ambush of Muzan, Kagaya’s eight-year-old son Kiriya seamlessly took over central command. His tactical precision and composure after his father’s death led the Demon Slayers to victory over Muzan. Kagaya trusted his son to finish the job because he brought up Kiriya with one goal: Lead the Demon Slayer Corps to victory.

Itachi Uchiha (Naruto)

Family Legacy: A genetic gift condemns the Uchiha clan.

• Curse of Hatred: Serving as a founding clan and the military police of the Hidden Leaf village, the Uchiha clan posed a longtime threat to Hidden Leaf leadership due to their unique ocular abilities. The Sharingan endowed the Uchiha clan with a powerful weapon to perceive, mimic, and manipulate reality. This biological weapon gradually fueled the Uchiha’s ambition to overthrow the administration.

• Hidden Leaf Coup: After a Tailed Beast attack on the Hidden Leaf village, the village leadership scapegoated the Uchiha clan and placed them under increased surveillance. The Uchiha clan began to plot a coup to reclaim their honor from a government that feared and suppressed their natural gifts.

The Blueprint of Martyrdom: Itachi redeemed the legacy of his clan at the expense of his soul and the strength of his might.

• Unrivaled Prodigy: Itachi graduated the Shinobi Academy at age seven and led the Hidden Leaf Secret Police by thirteen. Capable of defeating even the most seasoned shinobi with his Sharingan and his intellect, Itachi struck a deal with Hiruzen, the Third Hokage and leader of the Hidden Leaf.

• Uchiha Scapegoat: To maintain the honor of the Uchiha clan and the peace of Hidden Leaf village, Itachi murdered his entire clan (except his younger brother Sasuke) in a single night before fleeing the village as a publicly denounced criminal and traitor. In return, the village elders agreed to spare Sasuke’s life and preserve the Uchiha lineage.

Eren Yeager (Attack on Titan)

Family Legacy: A tale of unrequited love enslaves the Eldian race.

• Titanic Heritage: The tragic devotion of Ymir Fritz to a tyrant king tethered her descendants to a supernatural cycle of suffering. As Subjects of Ymir, the Eldians are born with the biological capability to transform into Titans. This genetic trait shackled Eldians into tools of war for centuries. Eventually this leads to their exile to Paradis Island, where they lived in ignorance of their persecution by the rest of the world.

• Shattered Sanctuary: Once a restless child who viewed the stagnant peace of the Walls as a gilded cage, Eren’s life was turned upside down when Marleyan Titans breached the boundaries of Paradis Island. This invasion fuels Eren’s obsession with freedom and radicalises him to reclaim his people’s honor from a world that sought their total extinction.

The Blueprint of Villainy: Eren forged a path of liberation at the expense of his humanity and the world’s blood.

• Relentless Vanguard: Eren inherited the Attack and Founding Titans, becoming the spearhead of the Survey Corps. Possessing the unique ability to perceive and manipulate memories across time, Eren used his superior tactical momentum to orchestrate his own destiny, striking a deal with the Paths to secure his people’s future. As a metaphysical dimension connecting all Eldians across time and space, the Paths is a realm allowing Eren to transcend linear reality and manipulate the very history that had enslaved his race.

• Monstrous Devil: To preserve the Eldian lineage and the lives of his friends (including his closest companions Armin and Mikasa), Eren initiated the Rumbling to flatten the world. By intentionally becoming the ultimate villain, he forced his allies to stop him, ensuring they emerged as the heroes who saved humanity while breaking the cycle of the Titans forever.

From Kagaya’s strategic succession, Itachi’s silent martyrdom, to Eren’s catastrophic villainy, each paid the heavy cost of their crown.

To what extent should we sacrifice ourselves while contributing to our family’s legacy?

How have you navigated this tension on your nextgen journey?

‘My fool of a son thought he was the hunter. He didn’t realize the leak was an elaborate ruse.’

‘Hasn’t his nightclub been a reliable source of alpha?’

‘Not this time. I suspect even the nightclub management was behind it. By this morning, the short squeeze was all over the news.’

‘Look on the bright side. You only had to pay a quarter’s worth of profit for a lesson your son will remember for the rest of his life.’1

Rarely do luxury items or expensive experiences land nextgens in financial ruin.

Wrongly betting the farm on a trade or a project, however, could put a meaningful dent in their portfolio.

All because they succumbed to the power of persuasion.

Having spent five years working for my family, I constantly parry persuasions that come my way while applying my own efforts towards my family.

It often boils down to Cialdini’s seven principles of persuasion.

Let’s explore how they work, how others use it for their benefit, and how we can too.

Reciprocity

How it works: We feel obliged to repay what we have received.

How others use it:

• A fund manager provides exclusive access to a closed event for you, making it harder for you to say no to their next investment pitch.

How you can use it:

• You behave towards your colleagues the way you wish your boss would treat you, so that your colleagues will gradually trust you as their future boss and be willing to work for you.

Commitment and consistency

How it works: We feel bound to our past words and actions, and behave based on commitments we have made.

How others use it:

• A salesperson gets you to agree to a small, easy trial. Once you’ve started, you feel a psychological pressure to follow through with the full deal

• Your dad asks you to come back and help out the family business for a month. Once you’ve publicly stepped into the role, it becomes harder to leave without hard feelings.

How you can use it:

• You keep minutes of conversations with key stakeholders, especially family members who are on the investment committee. Their remarks can be resurfaced at critical junctures to drive towards a conclusion.

Social Proof

How it works: We feel secure in mirroring our peers.

How others use it:

• A developer claims other major family offices are already in on the deal, creating FOMO.

How you can use it:

• You keep track of which industry titans your family leaders look up to and monitor their views. One comment might be enough to engineer the aha moment on a new investment theme for your family.

Authority

How it works: We are more likely to comply with experts.

How others use it:

• Advisors may inflate titles, drop names, or otherwise project themselves as someone of note when they’re not.

• Your dad claims he has pattern recognition honed over decades of doing business that trumps your data-driven findings.

How you can use it:

• You bring in a neutral, third-party expert to present your ideas to your family, leveraging on their authority.

• You build a personal brand for yourself, notching public speaking opportunities or podcast appearances and gradually compound trust with your family.

Liking

How it works: We prefer people similar to us.

How others use it:

• Some bankers use charm, access to rare events, or other methods (footrubs anyone?!) to assuage clients during seasons of underperformance.

How you can use it:

• You bond with family members outside of the family business proactively. The earlier you build common ground, the easier you will get help when you need it.

Scarcity

How it works: We perceive things of limited availability as higher value.

How others use it:

• Deal syndicators create artificial deadlines or limited allocations to force a quick decision, preventing you from performing proper due diligence.

How you can use it:

• You learn from the most prolific family offices. They often reach the decision to invest in a co-invest long before the opportunity presents itself.

Unity

How it works: We yearn for a shared identity and a sense of belonging.

How others use it:

• Private dealmaking clubs foster inner circles, in which inexperienced members co-invest more than they’d like, sometimes with undesirable financial consequences.

How you can use it:

• You frame your new initiatives not as your own quest for legitimacy, but as your contribution to your family legacy.

Which principle of persuasion have you detected others using on you recently?

How about the principles of persuasion you have used on others, especially your family?

Subscribe now

‘I heard my daughter walked out on you last week,’ said Victor with a wry grin.

Frank shrugged.

‘Melissa has delivered on everything she’s been asked to do.’

‘Then why did you turn down her request to be assigned to your biggest deal?’

‘You know how I treat folks when the stakes are high. I don’t want to subject Melissa to that side of me. What if she doesn’t live up to my standards? I can’t mete out the same consequences as I would to a normal hire.’

‘Do you know what she told me?’

Frank gave Victor a long look.

‘She said she doesn’t want me to line up things for her anymore,’ said Victor, as a wistful grin crept across his face.

‘Said she’d rather fail as a jungle lion than succeed as a zoo lion.’1

Do you know what’s more heroic than wanting to prove yourself without any help from your family?

Developing a stewardship mentality. Asking where your greatest abilities meet your family’s greatest needs.

Hate to break it to you Melissa, but the learning curve of remaining within your family’s orbit may be just as steep as stepping outside of it.

Suppose zoo lions describe nextgens still nascent in their ability, understanding, and desire to contribute to their family’s needs.

Then jungle lions likely describe nextgens well equipped to steward wealth and legacy of their families.

As I evolve from a zoo lion to a jungle lion, I often reflect on these questions:

1. What do I want?

2. What does my family need?

3. How can my family and I help each other?

what do I want?

When I started working for my family, I held a set of assumptions that supposedly delivers what I wanted.

Wealth, independence, and respect from those I respected.

Fiercely looking out for myself, it took a few years before a piece of advice my mother gave me decades ago took on a deeper layer of meaning.

‘Be a useful person. Don’t waste the resources you can access.’

I saw a virtuous cycle unfolding:

1. The more I became useful for my family,

2. The more access I got to the family’s intellectual, social, and financial capital,

3. The greater sense of ownership I felt over my responsibilities and initiatives.

Just like my mother predicted, I felt a strong desire to take good care of what was entrusted to me.

what does my family need?

The needs of families with operating businesses are diverse.

Yet the needs of families who have divested their business and now sit on liquid financial assets usually face the same formidable task.

How do we manage our wealth and legacy for generations to come?

Five years into working for my family’s single family office and family foundation, I guess I’m really blessed to be able to say this:

There’s no place I’d rather be than helping my family both invest and give like the best.

(… unless I find new arenas to accelerate my evolution from a zoo lion to a jungle lion!)

how can my family and I help each other?

Five years ago, my family thought crypto was just for money laundering, buying drugs, and moving money offshore.

Since I needed accredited investor-sized dry powder to access higher quality investment opportunities, I decided to borrow money from family and be held accountable for the gains and losses I make in crypto.

Investment became my first leap to build trust with my family.

Last year, my family published a book about my grandfather, cementing his legacy as a Pioneer, Patriot and Patriarch.

Legacymaking was a second step that drew the family closer.

This year, my sister and I are taking a more active role in our family foundation, recalibrating our giving based on family feedback and a new vision.

Philanthropy might be the third layer to reinforce the family’s sense of belonging.

I’m always on the look out for more ways to build trust within multigenerational families.

Are you a jungle lion? Teach me your ways.
Are you a zoo lion? Welcome to the pride.

Subscribe now

‘It’s my last day.’

The veteran gatekeeper flicked his lighter, the flame dancing in the high-altitude gusts.

‘I wonder why this GP snitched. No one else I brought to IC had an issue with my 20% take rate. Guess it was a good run while it lasted.’

He glanced at his young protege. Her gaze wavered.

‘It’s also my last day.’

They fell silent.

‘I tried to tack on another 20%.’

The wind howled.

‘I guess I won’t be working for my father again.’

Burning bridges with family over short term gain is tragically short sighted, yet surprisingly common.

Every nextgen leverages their family for personal gain. Some just do it more honorably and tastefully than others.

I apply the following litmus test:

Making money is not the only way to contribute. Here are three additional forms of capital nextgens should cultivate for their family:

1. Human Capital

2. Social Capital

3. Intellectual Capital

Subscribe now

human capital

Nextgens underestimate the role they play in helping their siblings figure out when is the right time to go back and work for family.

Last year, my sister worked as an architect for over half a decade and wanted a change of scenery.

What if I could encourage my sister to come back to the family office where

• the family benefits from another pair of capable, trusted hands, and

• my sister benefits from leveraging the family resources to pursue her dreams?

For the past five years, I have solely focused on helping my family invest like the best.

Preserving and growing the family wealth felt like the highest and best use of my time.

Until I walked alongside my sister throughout last year, addressing her concerns about working in the family office and sharing my personal experience.

My sister has since joined the family and taken an active role in our family foundation. She is redefining what philanthropy means for our family.

Empowering my loved ones to establish their legitimacy within the family legacy has now become a serious contender for the highest and best use of my time too.

social capital

Nextgens underestimate the influence their network can exert on their family.

When I first told my family to invest in crypto, it was met with blank stares.

Isn’t crypto for money laundering, buying drugs, and moving money offshore?

It took me the better part of 2021 to find someone who I felt might legitimise crypto in the eyes of my family.

I chased down every weak tie and showed up at industry conferences I had no business attending.

It was all worth it when I found a crypto VC that helped my family finally arrive at their aha moment.

My relentless search for our next family office whisperer continues.

intellectual capital

Nextgens underestimate the intellectual capital they can help their family accumulate.

I meet professionals, practitioners, or professors to monitor emerging investment themes such as space, longevity, nuclear, and wealthtech.

After each meeting, I ramble into my phone, record a voice note, and throw it into Gemini to create a one pager transcribing and summarising key takeaways.

Not all of these one pagers are worth sharing with my family, especially when the topic is too controversial, the follow-up action too inconsequential, or the pool of comparison too thin.

Every one pager, however, helps me gradually construct a mental model of how I should prioritise my attention across different themes.

Now over to you.

How are you leveraging your family to pursue your dreams?

In return, how are you contributing to your family’s needs?

Are you compounding not just wealth, but also trust within your family?

‘I don’t give a damn about AGI arriving in 2032.’

My mentor leaned back, a mischievous twinkle in his eye.

‘If I asked my kids to take over my business now and they told me their plan was to—what was that fancy term you used?’

Sheepishly, I replied: ‘Orchestrate autonomous AI agents.’

‘Right. That.’ He shook his head.

‘Unless you show me how AI instills in my kids:

• an entrepreneurial drive to be great;

• a desire to contribute to the family legacy; and

• how to build my trust in them by balancing these two at all times.

‘Otherwise, I don’t see how AI is going to help me with my succession planning.’

Millennials like me always pick fights with boomers.

Allow me to make a case for how AI shapes succession planning via:

1. Investment

2. Philanthropy

3. Entrepreneurship

4. Family Governance

Subscribe now

AI in Investment

The more money you make for your family, the more they trust you to manage the family wealth.

(I don’t make the rules here)

AI ruled private markets in 2025, where LLM household names experienced significant markups.

Paper gains, predatory fees, and a generous suspension of disbelief around these multi-billion valuations aside, investing in these companies probably gave you a decent credibility boost as your family’s AI expert.

(Note: Especially Anthropic in 2026. Last week they just closed a $30 billion Series G round, at a $380 billion post money valuation. This bumps the markup multiple to a cool 21x.)

Luckily, even the most diversified of exposures in public equities also benefitted from AI tailwinds in 2025.

Will AI still make money for you in 2026?

Ask your trusted investment professionals (and certainly not me).

AI in Philanthropy

The more you ask your family to give away money, the less they trust you to manage the family wealth.

(I’m just joking. Or am I...?)

It’s a long shot to make AI part of your theory of change that underpins your philanthropic strategy.

Funding AI alignment and related AI safety research is usually out of mandate for most private family foundations.

If you know any, please point them my way.

AI in Entrepreneurship

The more you build with AI, the more they trust you to navigate the future.

You may care a lot about whether your project

• aligns with or diverges from the family business;

• monetises or not; or

• might become obsolete.

But your family probably cares more about how building this business shows your:

• entrepreneurial drive to will it into existence;

• willingness in getting your hands dirty to sell this solution; and

• moral fortitude to take risks while bearing the family name.

AI in Family Governance

The more self work you put in with the help of AI, the less trauma hindering you from believing in the value of building trust with your family.

A senior family governance advisor at a leading Swiss Bank once described to me the most common activity she performs for his clients.

It’s not setting up legal trusts. Nor is it drafting family constitution documents.

Instead, she spends most of her time

• running workshops to get families articulating their values

• facilitating dialogue between parents and children to address intergenerational trauma

• mapping the spiritual capital, human capital, and other forms of non financial capital that defines the family.

To be fair, this advisor’s decades long track record of working for large billionaire families is the primary reason why patriarchs and matriarchs are willing to become this vulnerable. For boomers, AI agents simply don’t have the level of credentialing and social proof.

What about us the rising generation? Are we ready to conduct our own emotional due diligence with the help of AI? Is AI able to deliver the advisor’s work at a fraction of the cost?

Perhaps we can take the first step towards cultivating the emotional literacy needed for a family to flourish across generations.

A senior private banker once told me his client started paying his son a handsome monthly salary.

‘Congratulations, he must be doing great things for the family business. Sounds like you have found your successor!’

The client didn’t smile. She just stared at her drink for a moment before looking up.

‘Quite the opposite actually. I pay him HK$1,000,000 a month so that he can keep his hands off my business.’

Money solves many problems, but rarely the ones that matter the most.

The succession planning of the family business often runs roughshod over the hopes and dreams of each nextgen.

Whether recently returned or dutifully toiling within the family ranks, many nextgens share a common anxiety.

It’s not even about whether they think they are the designated successor or not.

“I worry I’ve lost my edge.”

“I feel less financially independent than ever.”

“I fear I may never amount to anything.”

Let’s unpack how a nextgen’s quest for legitimacy may be usurped by their family in these subtle ways.

Subscribe now

losing your edge

Who holds the nextgen accountable for growth?

Customers, suppliers, and other external stakeholders usually bring the heat in an operating family business. Nextgens either survive or wither under the pressure.

It gets tricky when the family exits the business and transitions to a single family office.

Without external stakeholders, it falls on the family leaders to set expectations for their nextgen.

Should a family business be run like a high performance sports team, where there is no room for mediocrity?

An iron fist with unrealistically high standards, however, can sap the desire to be productive.

Or should a family business be run like a kindergarten, where there is plenty of room for experimentation and little expectation to perform?

Again, a long leash to experiment without oversight may breed complacency and entitlement.

(Writer’s note: At the single family office I work at, we value stability and loyalty. Most of our staff have been with us since my grandfather’s days. They are likely working the last job of their lives.

For all the other hats I wear, I value growth and long-termism. It’s betting on long term secular trends, like the growth of asset management and education industry in Hong Kong, and building long term relationships with key players in these sectors.)

growing less financially independent

A family business is where many nextgens grow less financially independent.

This only becomes a problem when family leaders use money to control other family members.

Many Asian patriarchs, for example, reward their children handsomely for the first grandchildren they produce.

That’s why many nextgens I know prefer not taking a single penny from the family and choose to work outside of their family business because of this.

Morgan Housel’s philosophy of true wealth is relevant here:

For healthy families, however, nextgens ought to balance this spirit of self sufficiency with a sense of belonging to the family.

(Writer’s note: For me, I was blessed to have a family supportive of my aspirations and transitioning to a platform where different family members can pursue their own interests.

The past five years working for the family office has been instrumental in forming a robust network of asset owners, service providers, and investment opportunities. As it turns out, someone outside of my family was willing to pay for it too!)

fearing you don’t amount to anything

A family business is where many nextgens fear they never amount to anything.

Did the founding generation cast a shadow too great and delivered an act too tough to follow?

Thankfully, the tasks for nextgens always looks the same:

1. Protect the wealth

2. Grow the business (until it is sold, which goes back to task 1)

3. Craft the legacy

We as nextgens must pinpoint our unique contributions within these broader needs of the family.

I have previously highlighted four areas that can launch high growth careers inside and outside your family business.

(Writer’s note: For me, I’ve spent the past five years helping my family invest like the best. Here’s to the next five years building businesses serving nextgens like myself.

My mission is simple: empower every nextgen to conquer their quest for legitimacy!)

Suppose US$100m landed in your bank account.1

How would you steward this generational wealth?

How would you unlock financial freedom for not just yourself, but also your kids’ and grandkids’ families?

For me, I would start thinking about three things.2

1. How much gains do I want to make each year?

2. How much losses can I tolerate before I start selling each year?

3. How often and how much do I need to turn part of this US$100m into cash?

truly goated gains

Let’s look at legendary investors who have managed over nine figs for over three decades and did rather well.

I can only marvel at:

1. How good they were for so long at this game (outperforming the benchmark S&P500 for at least three decades, dating back to the ‘80s);

2. How much they have made for themselves.

It also makes me slightly depressed knowing:

1. How much they keep for themselves before making money for others;

2. How they most likely can’t help me turn my US$100m into US$1bn.3

8% over 30 years isn’t too shabby

Now look, what if I just throw everything into something compounding at 10%.

How much can I make?

Within 10 years, I cannot turn nine figs to ten...

Unless my US$100m grows at 25.89%+ on average each year for a decade straight.

Within 30 years, however, I become a billionaire...

Provided my money grows at 8%+ on average each year for three decades straight.

No wonder Investor C once said ‘The stock market is a device for transferring money from the impatient to the patient.’

from grocery stores to trading floors

Most of us haven’t experienced raging inflation before.

Last year, I met an Argentinian who did.

‘By the time I took an item off the shelf and brought it to the cashier, the price was different.’

‘Grocers were literally shouting out prices, like on trading floor, because the Argentinian peso devalued so rapidly.’

Adjusting for inflation is a must.

So how much gains do I want to make each year?

Personally, I’d go for inflation + 4-6%.

At current PCE levels of 2.8%, that’s roughly 7-9%.

I’m not handing a significant sum to anyone promising mid twenties over the long term. There must be a catch.

We discuss risk next week!

Dear nextgen brothers and sisters,

Your family needs more than just an heir. They need someone who will build upon the family’s legacy while pursuing his/her own dreams.

May I suggest four ways to achieve this1:

1. Investment

2. Philanthropy

3. Entrepreneurship

4. Family Governance

Investment

We as nextgens are often our families’ best hope to compound multi-generational wealth by becoming sophisticated consumers of financial products and services.

Most families who remain intimately involved with day to day operations have no time to figure out how to best deploy the healthy cashflows their business spits out.

Some families, having successfully exited their business, are now starting to explore how to invest like the best.

They attract banks, asset managers, and service providers, who call out to them like sirens on the shore.

Philanthropy

We as nextgens are often our families’ best hope to immortalize our families’ legacies by becoming sophisticated givers.

Our founding family leaders thrived in turbulent times and defied the odds to catapult us into prosperity. They are top 0.01% in earning money.

Are they also top 0.01% in giving away money?

Our families fear not the return of poverty, but the prospect of being tainted with infamy or fading into obscurity.

Entrepreneurship

We as nextgens are often our families’ best hope to anticipate the future by building new businesses.

Perhaps it is hard to understand why our families still need us when we are actively choosing not to return.

Yes, we may have a chip on our shoulder, wanting to prove we are worthy without the help of our families.

Yes, we may sometimes find it tough to deal with shade society throws at us.

Yes, we may wish to dodge emotional damage that our families inevitably inflicts on us (and vice versa).

But more often than not, we have discovered we are compelled to create something out of nothing.

That entrepreneurial spirit is key to greater resonance and eventual embrace of our nextgen identity.

Family Governance

We as nextgens are often our families’ best hope to explore best practices in multi-generational wealth management by equipping ourselves with family governance knowhow.

Every family thinks there’s a more dysfunctional family out there.

“Unlike those basket cases, there isn’t really a burning need for our family to put things in writing.”

“Why tie us down to a particular way of doing things, when trust level is high now?”

It would spare us nextgens a lot of headache if our kids were born into a clear set of rules of engagement.

How About You?

For the past five years, I’ve stuck to investment.

This year, I’m trying to add entrepreneurship to my succession planning toolbox (starting with this newsletter!).

How are you staying true to your dreams while contributing to your family’s legacy?

See you next week!

I used to argue with my dad a lot.

Five years ago, when I first joined the family office, I observed most people around him speaking rather nicely to him.

Very few people around him spoke their mind. Perhaps there isn’t a strong financial or social incentive to do so.

I thought I would take advantage of my status as his son to push the envelope.

I quickly regretted it when conversations began ending like this.

‘You don’t speak to your father this way. Have some bloody respect!’

the 24/7 onslaught

Boardroom discussions carried over to dinnertime conversations that often ended with me in tears.

In the throes of self-pity, frustration, and fatigue, I felt

• trapped by my Confucian conditioning, triggered by this patriarchal trump card.

• paralysed by my work environment, surrounded by emotional landmines.

• drained by these communication breakdowns.

Will it ever change? Do I even belong here?

Subscribe now

stewarding my family’s legacy

The crux of working in any family office is never managing the office.

It’s managing the family.

To my fellow brothers and sisters working for your dads and moms (or are about to!), I find these reminders helpful:

1. stop the self-pity

A trusted family advisor once told me: ‘We can’t choose the families we were born into. All we can do is play the best out of the hands we have.’

It’s no use dwelling on my perceived injustice and feeling sorry for myself.

I am not a victim and my dad is not a villain.

2. remember tolerance is a two-way street

Most of the time, I do a great job tolerating my dad’s temper.

It got too much once, so I complained about his anger management issues.

(Note: never bring up anger management issues to someone while he or she is angry.)

In a remarkable moment of clarity, my dad told me:

‘Why can’t you tolerate my imperfections? Don’t I tolerate your imperfections?’

3. find what is worth fighting for

I say I used to argue with my dad a lot, because I no longer do.

Perhaps I just got a lot better at managing upwards.

(Let’s compare notes on managing our fathers. Or mothers. Or father-in-laws. Or any family elder for that matter!)

But perhaps I started wanting to become more than just an allocator of the wealth passed down from my grandfather.

I want to become a steward of my family’s legacy that will endure across multiple generations.

What does that entail? I don’t really know, to be completely honest.

But that feels like something worth fighting for.

See you next week!

My name came up during a boozy black tie dinner my uncle attended last month.

He was in a group of three, including the host. The remaining gentleman blurted before the host could say anything.

‘That guy? He used to work at my startup, and then went back to work for his family. Haven’t heard from him in a while. Feels like he went into semi-retirement!’

Sheepishly, my host introduced my current boss to my old boss.

past assumptions

I had a bunch of questions when I first joined the family office:

1. What is a family office anyway?

2. What is expected of me here?

3. How is it like working for family?

4. If I join, does this mean this will be my last job forever?

It’s silly to mind read myself five years ago but these are best guess of the assumptions I used to vaguely hold in my mind:

1. A family office preserves and grows wealth.

2. The better investor I become, the more money I’ll make, the more respected in my family and my field will be, the more control I have over my life.

3. I’ll manage my bosses just like I’ve manage other bosses in the past.

4. I need an exit strategy. Again, the more money I have, the more control I have over my life.

I’m a more trustworthy narrator if I tell you my latest assumptions.

But first, let me explain what changed.

Subscribe now

my ABCs of working in family

In these past five years working for the family office, I felt greater autonomy, belonging (aka relatedness, purpose), and competence (aka mastery) now than when I started.

Autonomy

• I joined my family a few years after my elders sold the listed family business and started investing the proceeds.

• I was spared from specialising into one sector and encouraged to look broadly at new economy sectors and asset classes that could futureproof our family’s portfolio.

• I started in venture capital and ended up spending a lot of time in crypto. It was the best decision I’ve ever made, not in terms of the most money I made for my family, but in terms of the degree trust I’ve built with them.

• Now I’m ready to try something new. Like this Substack!

Belonging

• I could go into all the strategies I use for managing upwards but at the end of the day, it’s realising whether family is worth fighting for. That’s a story for another day..

Competence

• I personally think losing less of the family’s money year after year is nice, but no return comes without risk. Making more money year after year is great, but how sustainable is it?

• I prefer to measure progress based on a few things. Am I explaining new concepts effectively, especially to my family? Am I attracting sophisticated peers and deal flow organically, especially in emerging domains? Am I developing better taste?

• Perhaps the score will take care of itself.

coming out of semi-retirement

So here comes my latest assumptions:

1. A family office is one of many platforms for self actualisation of family members from different generations

2. The more holistic my understanding of skills required to help my family flourish for the long term, the more focused my quest becomes to cultivate those skills, the rest will take care of itself

3. I need to be intentional in what and what not to do to cultivate strong bonds within my family. Relationships can achieve sometimes even the strongest of governance structures cannot.

4. Control is an illusion. Keep my options open but commit to something and give it my best efforts. A portfolio approach applies not only to finances, but also to life.

Should be fun revisiting this in another five years!

I’m not a private banker, nor a family advisor, nor a GP, nor a non-family single family office executive, nor a family business academic, nor an investigative reporter.

As a third generation millennial family member working at a Hong Kong based single family office and family foundation both established by my boomer family elders, however, part of my job is to develop a pipeline of these professionals.

Five years in, embedding myself in this ecosystem - I observe nothing bonds folks quite like gossip about wealthy families, anywhere from salacious rumours to succession sagas.

just doing my job

Some I can’t help being caught up in equal parts schadenfreude and morbid fascination: millennial heirs frittering away generational wealth, boomer patriarchs incentivizing infighting among family branches by awarding bounties for grandchildren.

Others I listen with far more empathy: millennial heirs struggling to earn their family’s respect no matter how hard they try, boomer patriarchs tidying up the mess their enthusiastically incompetent millennials constantly leave behind.

Still, some stories I feel there is something amiss: millennial heirs striking out on their own with so much success they refuse to get involved with the family business, boomer patriarchs deciding to die with zero or to wholly professionalize the family business with no intention of grooming successors within the family.

I know - these are purely first world problems.

Subscribe now

for the record

So it felt hilariously hubristic to be invited to speak at a family business symposium hosted by one of the leading universities here in Hong Kong, back in November 2024.

I brushed my insecurities aside and thought to myself: what did I have to lose?

I feel empowered working for my family and compelled to reciprocate my family leaders’ trust by equipping myself with skills to manage our financial and human capital the best I can.

On 24 Jan 2025, I gave a TED talk style 25 minute sharing in front of almost 200 family principals, executives, and academics.

Boy would that create an unforgettable experience.

Not the talk itself, but what inevitably followed as I experienced in another 11 speaking gigs across Hong Kong, Beijing, London, and Los Angeles during the rest of 2025 when I delivered similar speeches.

Without fail, several strangers would come up to me and open up about themselves in ways I could never imagine.

Most were millennial and gen Zs resonating with my observations on working for our parents.

Some were family advisors and executives sharing about their journey of persuasion, facilitation, and sometimes, painful intervention.

Once, I had a boomer patriarch told me to spend time with his children convincing to go back to work for them. The nerve!

Slowly, these conversations culminated in a thought that just wouldn’t go away.

my bet for 2026

Imagine a platform built by, and exclusively for millennials and gen Zs from business families.

Imagine it hosting conversations on topics like:

• how to utilise entrepreneurship, investment, and philanthropy as tools to build trust within business families

• how to balance access to family resources and independence from family control

• how to mitigate the corrosive effects of wealth

• how to manage family expectations of your personal and professional life

• how to overcome resentment, ennui, and other forms of emotional resistance in working with family

Imagine it helping millennials and gen Zs from business families

• disentangle their families’ succession planning from their own quest for legitimacy;

• know what it is that will make them truly feel at peace;

• pursue it with all their heart, body, and soul;

• support each other through accountability, encouragement, and unconditional acceptance

Now that’s a thought I intend to will into existence in 2026.