Inside a 160-Year-Old Family Office: What Seven Generations of Wealth Management Teaches Us

Written By Ryan Morrison

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Introduction

What does it take to manage family wealth across seven generations and 160 years? Most families struggle to maintain wealth past the third generation, yet some family offices have cracked the code on multi-generational stewardship. \

In this episode of Navigating Wealth, we sit down with Ilka Gregory, President and CEO of a seventh-generation single family office that's been operating since 1866, to understand what really happens inside these often-misunderstood institutions.

For successful individuals with substantial assets who are considering whether they need a family office, thinking about setting one up, or simply curious about how ultra-high-net-worth families structure their wealth management, this conversation offers rare insight into an institution that typically operates behind closed doors.

 

Guest Snapshot

Guest Name: Ilka Gregory

Titles:

  • President and CEO of a private single family office

  • Strategic Advisor to Fiat Ventures

  • Advisory Board Member at Rondeivu

Credentials:

  • Two decades of experience across Goldman Sachs, Bessemer Trust, Lazard Family Office Partners, and Third Avenue Management

  • Former Managing Director and Head of Client Relationships at Lazard Family Office Partners

  • Former Head of Wealth Advisory at HQ (Digital Currency Group ecosystem)

Current focus: Leading investment strategy, family governance, and multi-generational wealth planning for an 80+ member family across seven generations

Additional areas of expertise: Alternative investments, digital assets, impact investing, and family office operations

 

What is a Family Office?

The term "family office" gets thrown around frequently, often by people who don't actually have one. Gregory clears up the confusion: a true single family office serves one blood lineage and handles far more than investment management.

"For us, the family office was originally started to manage the wealth of our original patriarch and his family," Gregory explains. "Now that we have four main branches and 80 plus family members, we do everything from investment management of that original source of wealth to tax and estate planning, family governance, and education for the next generation."

The distinction between single family offices and multi-family offices matters. While multi-family offices serve multiple unrelated families and often have minimum investment thresholds, single family offices are dedicated entirely to one family's needs. Gregory has experience on both sides, having worked at multi-family offices before leading a single family office.

Key differences include:

  • Single family offices serve one family exclusively, while multi-family offices aggregate multiple clients

  • Investment minimums at quality multi-family offices typically start around $25 million

  • Single family offices can customize everything from investment strategy to family governance

  • Multi-family offices offer economies of scale but less personalization

 

Multi-Generational Wealth Stewardship

Managing wealth across seven generations requires more than good investment returns. Gregory's family office, which now serves 80+ family members spanning from a 90-year-old matriarch in Generation 4 to newborns in Generation 7, focuses on three core areas:

Investment Management

The office manages the original concentrated source of wealth alongside diversified portfolios for different family branches. "We've had to think about diversification over time," Gregory notes. "There's a lot of emotional connection to concentrated positions—feeling like we always have to have this because it's what made us wealthy. But there's significant risk when you have that kind of concentration."

Family Governance

With 80+ stakeholders, governance becomes essential. The family has established:

  • A board with both family and external members

  • An investment committee that includes spouses and stepchildren who are "truly professionals about it"

  • Regular family meetings to maintain alignment

  • Education programs for younger generations

Succession Planning

Perhaps the most critical function is preparing the next generation. "Back filling that pipeline is something I think about," Gregory says. "Who in G6 and G7 might be good candidates for an IC position one day or for a board position? How do I help prepare them for that?"

 

The Shirtsleeves-to-Shirtsleeves Question

The old adage suggests that wealth moves from shirtsleeves to shirtsleeves in three generations—the first generation builds it, the second enjoys it, and the third squanders it. Is this real or overblown?

Gregory's experience suggests it's more nuanced than the saying implies. She points to education and preparation as the key differentiators. "We had one client who thought maybe 15 million upon her mother's passing, and it was in the hundreds. That responsibility of being a steward was almost paralyzing. She hadn't been prepared for it."

The families that succeed across generations tend to share common traits:

  • They start financial education early, appropriate to each generation's age

  • They don't hide wealth from family members, but introduce it gradually

  • They put governance structures in place before they're needed

  • They balance giving family members opportunity while providing appropriate guardrails

 

When is the Right Time to Start a Family Office?

The question of when to establish a family office came up repeatedly in our conversation. Gregory's guidance breaks down based on both net worth and complexity:

Net Worth Considerations

"I think 25 million might be small for setting up your own family office," Gregory notes. She's seen clients with a couple hundred million who manage everything themselves with a home office, while others with similar wealth prefer working with professionals.

The threshold isn't purely about the dollar amount. Factors that push the need higher include:

  • Whether you want dedicated staff focused solely on your family

  • The complexity of your asset structure (operating businesses, illiquid investments, international holdings)

  • Whether multiple family branches need coordination

  • Your own expertise and interest in financial management

The Professional Advisory Route

For those with $25-100 million, Gregory recommends considering multi-family offices or private banks rather than building from scratch. "It just has to be someone that you really trust," she emphasizes. "What I do think is powerful is then starting to build and create a community and network of peers that you trust."

This aligns with what Long Angle members already know: peer networks provide value that even the best advisors can't replicate. The ability to discuss challenges with others facing similar situations, without sales pitches, creates a different kind of learning.

 

State Tax Policy and Family Office Location

The conversation opened with a discussion about California's proposed billionaire wealth tax, which provided context for how policy affects family office decisions.

Gregory's observations from her network are telling: "We have a few members based in LA and San Francisco, but I haven't heard anything yet about concerns or plans of moving out of state to avoid taxation." These are well-rooted families without immediate plans to relocate.

However, the tax impact may be more subtle than dramatic exits. As the hosts noted, the bigger effect might be on who decides not to move to California in the first place, rather than prompting mass departures. "If you're living in Texas and thinking about moving to California, then I feel like it seems much bigger," one host pointed out. "That disposable income that you're saving could literally be half of what would now go to taxes."

For established families, the calculus is different. If you have an operating business still running in a state, if your family and social connections are there, if you've built a life over decades—taxes become one factor among many, not the determining factor.

 

The Spouses and Stepchildren Question

One of the more delicate aspects of multi-generational family offices involves how to treat spouses, stepchildren, and those who marry into the family. Gregory's office takes an inclusive approach.

"If you're family, you're family," she explains. "We have folks that serve on the board, serve on the IC. We have spouses. I'm just really grateful to have members of this family that are committed to the mission and available."

Not all families take this approach. Some restrict gifting strictly to bloodline descendants, while others fully integrate anyone who joins the family. The key is being intentional about the choice and implementing it consistently through trust documents and governance structures.

 

Preparing the Next Generation Without Paralyzing Them

Perhaps the most valuable insight from Gregory's experience is how to handle wealth education with the next generation. The risk cuts both ways: tell them too little and they're unprepared when they eventually inherit; tell them too much too early and you risk affecting their motivation or creating anxiety.

Gregory shared a cautionary example: "We had one client who thought maybe 15 million upon her mother's passing, and it was in the hundreds. That responsibility of being a steward was almost like paralyzing. She got introduced to us and a lot of it was just hand-holding."

The client's grandfather had acquired a concentrated stock position that had grown enormously, creating deep emotional attachment. "There's this tie to our family lineage and identity," Gregory notes. "Realizing that there's a lot of risk when you have that kind of concentration" required not just financial advice but emotional support.

Best practices for next-generation education include:

  • Starting conversations early but age-appropriately

  • Focusing on stewardship responsibilities rather than just the size of the wealth

  • Providing education before major inheritance events

  • Using trust structures and appropriate trustees for those who may not be as prudent

  • Creating opportunities for younger generations to participate in governance before they need to lead

 

The Digital Assets Chapter

Given Gregory's experience as former Head of Wealth Advisory at HQ in the Digital Currency Group ecosystem, we asked about her current perspective on digital assets in family office portfolios.

Her approach reflects the pragmatic thinking that comes from actually implementing strategies rather than just theorizing about them. Family offices serving crypto executives faced unique challenges around liquidity, tax planning, and building diversified portfolios when net worth was concentrated in digital assets.

The experience informed how she evaluates digital asset opportunities today, though she stopped short of prescribing specific allocation percentages. The underlying lesson: any asset class that represents concentrated wealth needs careful planning around diversification, regardless of whether it's tech stock, real estate, or cryptocurrency.

 

Building Community Beyond the Balance Sheet

Throughout the conversation, Gregory returned to the importance of networks and community. She describes herself as a "NetworkSommelier" and emphasizes the role of curated peer connections in successful wealth management.

"What I do think is pretty powerful is starting to create the right community," she says. "It takes time." This aligns with the Long Angle approach: verified peers facing similar challenges create value that can't be replicated through expert advice alone.

For first-generation wealth creators especially, finding others who understand your specific situation—whether that's managing through a liquidity event, diversifying a concentrated position, or planning for the next generation—provides both practical guidance and emotional support.

 

Practical Takeaways for Wealth Builders

Based on Gregory's two decades working with ultra-high-net-worth families, several clear principles emerge for those in the wealth acceleration phase:

  1. Don't rush to set up a family office. Just because you can afford one doesn't mean you need one. Many successful individuals with $50-200 million work effectively with multi-family offices or private banks.

  2. Build your network strategically. Whether through formal organizations or communities like Long Angle, connecting with peers facing similar challenges provides value that advisors can't replicate.

  3. Start governance conversations early. If you're planning for multi-generational wealth, establish governance structures before family conflicts make them necessary.

  4. Balance concentration and diversification thoughtfully. Emotional attachment to the source of wealth is natural, but concentrated positions carry real risk that needs active management.

  5. Prepare the next generation gradually. Start financial education early and increase complexity over time. Sudden wealth discovery creates challenges that proper preparation can prevent.

  6. Choose advisors you genuinely trust. At these asset levels, technical competence is table stakes. The differentiator is finding professionals whose incentives truly align with yours.

  7. Consider life factors beyond taxes. While tax efficiency matters, where your business operates, where your family lives, and where your community is rooted often matter more for long-term decisions.

 

The Path Forward

For successful individuals with substantial assets, the question isn't whether to think strategically about wealth management—it's how to do it in a way that serves both current needs and future generations.

Gregory's perspective, shaped by managing one of America's oldest family offices, suggests that success comes less from perfect investment returns and more from thoughtful governance, prepared heirs, and trusted advisors. The families that maintain wealth across generations are those that treat it as a responsibility to be stewarded rather than just an asset to be managed.

Whether you're at $10 million and thinking about your first steps toward more sophisticated wealth management, or at $100 million considering whether to establish a family office, the principles remain consistent: educate yourself, build community, start governance early, and remember that the goal isn't just preserving wealth—it's empowering the people who will eventually inherit it.

 

Memorable Quotes

"If you're family, you're family. We have folks that serve on the board, serve on the IC. We have spouses. I'm just really grateful to have members of this family that are committed to the mission."

"That responsibility of being a steward was almost like paralyzing. She hadn't been prepared for it."

"What I do think is pretty powerful is starting to create the right community. It takes time."

"There's this tie to our family lineage and identity. Realizing that there's a lot of risk when you have that kind of concentration."

"The 25 million, I do think that if you don't want to be completely self-directed, depending on your training background experience, working with a professional probably does make sense."

 
 

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Ryan Morrison
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