Podcast Summary: Top Advisor Podcast

Episode #101: Becoming the First-Call Advisor – Insights from Family Office Expert Rich Wolkowitz

Host: Bill Cates
Guest: Rich Wolkowitz, Attorney, Family Office Advisor, Founder of Xylogenesis
Release Date: November 5, 2025

Episode Overview

This episode explores what it takes to become the “first-call advisor” for ultra-high-net-worth families and family offices. Bill Cates hosts Rich Wolkowitz, a multi-generational family member, attorney, and founder of Xylogenesis. Rich shares insights drawn from his experience in law, the White House, running his family enterprise, and serving as an external CEO and consultant for major family offices. Listeners gain actionable advice on building trust, creating meaningful relationships, and serving families across generations.

Key Discussion Points & Insights

Rich Wolkowitz’s Unique Journey

• Family Legacy: Grew up part of a fifth-generation family in St. Louis, learning early about the nuances of family culture and business ([04:08]).
• Speaking Truth to Power: Work in the White House as an attorney ingrained the importance of giving honest advice—even when it’s not what leadership wants to hear.

  “I was asked to speak truth to power and we got results as a result of that...always speak the truth.” — Rich Wolkowitz [04:35]

• Shift to Family Enterprise Focus: Transitioned from practicing law for public/private companies to specializing in family enterprises, eventually leading his own family’s business and, after a liquidity event, serving as a non-family CEO for other family offices ([06:30]).
• Consulting with Xylogenesis: Now works as an independent consultant to multiple family offices, leveraging his multidisciplinary background.

The Nature of Service in a Family Office

• Holistic Needs: Advisors are called upon for both technical and deeply personal requests—solving medical emergencies, managing family disputes, discreetly resolving conflicts ([09:27]).
• Right Brain & Left Brain Work:

  “There’s the quantitative...and then there’s the qualitative...we often forget about our heart.” — Rich Wolkowitz [09:35]

• Examples of Unusual Requests:
  • Helping a child with a rare disease
  • Navigating the firing of a family member for harmony
  • Dealing with pets’ health crises

Becoming the “First-Call Advisor”

• Definition: The go-to, trusted advisor for any family need—whether technical, personal, or emotional ([11:13]).
• Mindset Shift:

  “You want to position yourself to be that first call. And so I help work with advisors of all types to really understand how to have that breakthrough…” — Rich Wolkowitz [11:40]

What Advisors Get Wrong (& Right)

Common Mistakes

• Misaligned Motivation: Placing compensation model and personal KPIs above true service ([13:41]).
• Transactional vs. Relationship Focus: Clients see through self-centered advice; avoid becoming territorial or “siloed.”

  “Your advice...is always on what's good for me instead [of] what's good for the client. And clients eventually see through that.” — Rich Wolkowitz [14:06]

• Failure to Involve/Respect All Family Members: E.g., ignoring heirs with relevant financial knowledge means losing the next generation ([15:59]).
• Statistics:

  “85% of next gen leave their parents’ advisor...because advisors just talk about performance.” — Rich Wolkowitz [18:50]

• Overlooking Teamwork: Not collaborating with co-advisors (tax, legal, investment) can harm client outcomes ([17:48]).
• Underestimating Technology & Fee Compression:

  “If you’re charging...and you’re not providing value beyond the performance...you’re going to fall to that 85% statistic.” — Rich Wolkowitz [19:40]

Winning Strategies

• Servant Leadership: Put the client’s family and legacy ahead of self-interest ([13:41]).
• Givers Gain: Generosity with wisdom, time, and connections creates long-term value ([15:16]).
• Team Collaboration: Recognize and incorporate the entire advisory community; be proactive in creating unity for the client ([17:48]).
• Value Beyond Investment Performance: Offer relationship guidance, succession planning, and family governance ([19:55]).

Family Office Structure & Challenges

• Types of Family Offices:
  • Single-family office: Fully internalized services
  • Virtual family office: Outsourced to trusted advisors
  • Embedded/multifamily models ([23:38])
• Core Challenges:
  1. Lack of Strategic Planning: Many hurry into forming offices without clear purpose or road map ([21:14]).
  2. Budget & Cost Clarity: Is the office a cost center, revenue generator, or something else?
  3. Getting the Right People: Avoid putting beloved but poorly equipped insiders into leadership roles; hire “expert generalists” ([24:29]).

  “At the end of the day, a family office is there to serve people. And yet the number one mistake family offices make: not getting the right people who understand the family culture...” — Rich Wolkowitz [24:33]

The Importance of Alignment & Expectations

• The “Xylogenesis Effect”: Using tree rings as a metaphor, Rich helps families illustrate and discuss their alignment and health over generations ([25:39]).
• Alignment Exercise: Families often lack clear, unified future aspirations—sometimes even basic understanding between spouses ([26:46]).
• Expectations: Every success or failure comes down to setting and maintaining clear, shared expectations ([25:18]).

Toxic Loyalty & Nepotism

• When Loyalty Goes Bad: Multi-generational firms can develop cultures where no one challenges leadership, leading to “toxic loyalty,” apathy, and inherited dysfunction ([28:18]).
• Nepotism Nuance: Not always negative; can be a succession strategy if executed with transparency and capacity-building in mind ([28:33]).
• Staff & Advisor Challenges: Employees and external advisors often fear damaging relationships or careers by speaking uncomfortable truths ([31:28]).

  “How far do I push, how far do I speak truth to power...I could jeopardize the account.” — Rich Wolkowitz [31:33]

• Guardrails: Robust governance and established “permission to speak up” culture prevent issues before they arise ([32:38]).

  “It's easier to do on the front end when you're getting clients...” — Rich Wolkowitz [33:30]

Notable Quotes & Memorable Moments

• [04:35] “Speak truth to power and we got results as a result of that.”—Rich Wolkowitz
• [09:35] “We often forget about our heart...this is a business, a family office is a business for the family.”
• [11:40] “You want to position yourself to be that first call.”
• [14:06] “Your advice...is always on what's good for me instead what's good for the client.”
• [18:50] “85% of next gen leave their parents’ advisor…”
• [25:18] “At the end of the day, a family office is there to serve people. And yet…the number one mistake family offices make: not getting the right people who understand the family culture...”
• [31:33] “How far do I push, how far do I speak truth to power...I could jeopardize the account.”

Timestamps for Key Segments

• Rich’s Background & Philosophy: [04:08–08:29]
• Unusual Family Office Challenges: [09:27–10:43]
• First-Call Advisor Concept Defined: [11:13–12:18]
• What Advisors Do Wrong: [12:59–15:59]
• What Advisors Do Right: [17:48–20:15]
• Challenges in Family Office Formation: [21:14–24:33]
• The Xylogenesis Effect & Alignment: [25:18–27:35]
• Toxic Loyalty and Nepotism: [28:18–32:38]
• Setting Expectations & Permission to Speak Up: [32:38–33:35]

Tone & Takeaways

The conversation is candid, practical, and laden with real-world examples. Rich Wolkowitz communicates with humility, emphasizing the need for self-awareness, courage, and empathy among advisors. Bill Cates reinforces the importance of relational focus and encourages listeners to rethink how they can bring unique, lasting value to high-net-worth and multigenerational families.

Actionable Wisdom for Advisors

• Focus on servant leadership and aligning with the client's family values.
• Foster multi-disciplinary teamwork; know your limits and bring in outside experts.
• Go beyond numbers—help families plan for alignment, succession, and healthy relationships.
• Encourage upfront conversations about expectations and permission to give honest feedback.
• Recognize and guard against toxic loyalty, nepotism, and blind spots in both client and advisor communities.

Connect with Rich Wolkowitz:
Search for Rich Wolkowitz (W-O-L-K-O-W-I-T-Z) on LinkedIn or see the show notes for links.
Learn More About Xylogenesis: The firm and its metaphor for family alignment described at [25:39].

(Note: Intro, ad reads, book promo, outros, and sponsor plugs have been omitted for clarity.)