Jun 27, 2023 · 37m · we-live-to-build
Our Family's Money Goes In First - Here's Why That Changes Everything
0:00 / 0:00
▶ Watch on YouTube →
gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this episode of the 'We Live To Build' podcast, host Sean Weisbrot interviews Brendan Holt Dunn, CEO of Holden, on the principles of multi-family office governance, co-investing alignment, and multi-generational capital preservation. Dunn shares how Holden combines disciplined investment strategies and modern technology with bespoke, high-touch client stewardship.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Sean holds 25.7% of the talking time here. How this is scored →
Sean as informed peer 3.5 Guest teaching 2.9 Guest disagreement 0.6 Sean pushing back 1.0
speaking balance: gold is Sean, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 35:17 Brendan challenges Sean on trusting life savings to an AI
Brendan directly challenges Sean's argument about AI taking over portfolio management by asking if Sean would personally trust a computer to manage all his family wealth.
Hardest push from Sean ▶ 34:47 Sean counters skepticism about AI management with ChatGPT experimentsSean pushes back against Brendan's skepticism regarding AI financial management by citing real-world examples of people using ChatGPT to trade and build businesses profitably.
Biggest teaching moment ▶ 32:06 Brendan equates crypto custody risks with standard banking vulnerabilitiesBrendan reframes Sean's worry about crypto key theft by pointing out that traditional banking credentials and rogue advisors pose nearly identical structural security risks.
Sean holds their own ▶ 17:29 Sean explains business intelligence architectures and AI automationSean demonstrates deep practical knowledge of modern business operations by detailing how foundational automations and data integration are mandatory before enterprise AI can function.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Sean as informed peer | Guest teaching | Guest disagreement | Sean pushing back | Why |
|---|---|---|---|---|---|---|
| Aligning Interests in Multi-Family Office Wealth Management | 2 | 2 | 1 | 1 | Sean asks exploratory questions about the advantages of a multi-family office and whether Brendan felt pressured to join the family business. Brendan politely dispels pop-culture misconceptions about family offices being cutthroat like the show Succession. | |
| Investment Philosophy, Competence, and Ethical Exclusions | 3 | 3 | 0 | 1 | Sean probes whether the firm enforces specific moral or ESG exclusions when investing. Brendan explains their philosophy of competency first, clarifying that ethical restrictions are tailored to individual client mandates rather than imposed across all portfolios. | |
| Equity Market Track Record and Algorithmic Sports Investing | 3 | 4 | 0 | 1 | Sean asks for typical benchmark figures while acknowledging his lack of precise index data. Brendan details their 33-year track record of beating market benchmarks by 2% annualized and introduces their quantitative sports betting fund. | |
| Managing High-Risk Demands and Defining Investor Profiles | 2 | 3 | 1 | 1 | Sean asks how the firm handles demands for high-risk, hyper-growth investments and seeks wild client anecdotes. Brendan calmly explains their firm is deliberately conservative and rejects clients looking for reckless speculation. | |
| Implementing Operational Technology and Relationship Management | 6 | 2 | 0 | 0 | After Brendan admits client communication is a technological area for improvement, Sean shares a detailed monologue on automation foundations required for operational AI. Brendan agrees with Sean's operational framing before explaining how relationship managers handle client books. | |
| Client Privacy, Discretion, and Capital Onboarding Thresholds | 2 | 3 | 0 | 0 | Sean inquires about peer networking among clients and minimum asset onboarding requirements. Brendan explains the strict confidentiality rules they uphold and outlines the flexible five to ten million dollar baseline for prospective clients. | |
| Marketing Strategies and the Power of Personal Branding | 5 | 2 | 1 | 2 | Sean asks about content marketing and pushes the value of personal branding based on his experience hosting 150 podcast episodes. Brendan remains skeptical that digital campaigns attract ultra-high-net-worth clients but acknowledges branding can build general awareness. | |
| Digital Asset Custody, AI Disruption, and Generational Risk | 5 | 4 | 2 | 2 | Sean questions Brendan on crypto estate custody and the potential for AI disruption in wealth management. Brendan turns the question back on Sean, noting that high-net-worth clients prioritize trusted human relationships over automated algorithms with their life savings. |
Statements from this episode (15)
Holden builds segregated, unpooled client portfolios rather than pooling capital
“What we do is build discretionary portfolios on a segregated basis, meaning we don't pool client capital together, and we build customized portfolios for each client based on their own unique circumstances, risk tolerance, and time horizon.”
Dunn: Holden co-invests family capital into all client recommendations
“As our family office, we act as the anchor client. So if I'm going to you, Sean saying, Hey, I really believe in your portfolio. We should be buying you X number of shares of Apple. You have comfort knowing that our family is going to have that exposure as wel…”
Dunn: Asset managers without personal exposure risk fees, not personal wealth
“Most independent asset management firms, you know, they might be managing a lot of money, but that money is not theirs. It's just client money. So they might lose 20% on a position, and it'll hurt their management fees, it'll hurt their performance fees, but m…”
Dunn: Family offices must support individual passions over forced succession
“The whole goal of a family office is really to support, nurture, and grow, The family members, right? And support them in whatever their passion may like, because they'll, they're going to be successful. Can't really force people into something like into this …”
Dunn: Holden avoids biotech and pharma investments due to lack of expertise
“So we don't have any investments in biotech or pharma or anything like that simply because we don't have a knowledge or understanding where we are confident we can make that investment for our clients.”
Dunn: Holden tailors ethical investment exclusions to individual clients
“So the way we work at it is, is basically on a client by client basis. Each person has their own unique views and values, and it's not us to force our ethical beliefs on each individual client.”
Dunn: Holden equity portfolios beat benchmarks by 2% for 33 years
“So we have a track record of, I believe it's 33 or 34 years now of outperforming the U S index. Or the Canadian index because we keep us portfolio separate from the Canadian because different currencies, but both portfolios have outperformed their market bench…”
Dunn: Holden's algorithmic soccer betting fund averages 15% to 22% annual returns
“So it averages around 15 to 22% a year. What's great about it, it's uncorrelated to anything happens in the world, like interest rates go up and we're still doing well. You know, Ukraine war hits. We're still doing well. You know, there's the risk of the, you …”
Holden rejects clients demanding aggressive options trading or short selling
“If they're expecting us to go and, you know, do a lot of call options or short or do a lot of You know, risky stuff in the stock market to try to hit it like a home run. We would not take on that client, but what we would do is create what we believe is our co…”
Weisbrot: AI in business operations requires prerequisite data automation foundation
“AI is mostly useful for a business in its operations. And the only way that the AI can be useful in its operations is if you've already built a foundation of automation and integration within your operations so that the AI can pull the data from those differen…”
Dunn: Holden will never scale beyond knowing every client personally
“We would never want to be big and so big where. I don't know who you are. I don't know where you live. I don't know about your family. And you just feel like you're just a number at a bank. That's not the way we operate.”
Dunn: Managing a $500K client takes same work as $15M client
“Managing a 500,000 dollar client is the same amount of work as a 10 or fifteen million dollar client, right?”
Holden sets $5M to $10M minimum for inbound clients
“So if you're looking at it, if it's just an inbound option, we're saying five or ten million would be a minimum and we'd look at, but then there's the friends and the individual relationships that we have where there really is no minimum.”