Podcast Summary: How I Invest with David Weisburd

Episode 273 — What the Best Family Offices Do Differently

Release Date: December 31, 2025
Host: David Weisburd
Guest: Alex (co-founder, Endurance Family Office)

Episode Overview

This episode delves into the unique ways elite family offices—specifically Alex’s firm Endurance—approach investing, portfolio construction, and organizational design. Through a candid conversation with host David Weisburd, Alex details how entrepreneurial thinking, a “principals only” mentality, and sharp behavioral awareness enable their family office to outperform institutional peers. The discussion covers everything from the genesis of Endurance and its investment philosophy to practical lessons on asset allocation, manager selection, decision-making psychology, and information diet.

Key Discussion Points & Insights

1. Founding Story & Entrepreneurial Approach

• The Origin of Endurance

  • Formed by three serial entrepreneurs with backgrounds in investing (00:06).
  • Initial structure: a holding company for startup incubation, serving as "insurance" against high startup failure rates.
  • Outperformed expectations: 5 out of 6 incubated companies succeeded, providing significant liquidity (00:48).

• Building a Family Office from First Principles

  • Developed their own investment office, eschewing expensive third-party solutions.
  • Saw most commercial options as “beta trackers” while believing small outperformance compounds vastly over time (01:35).
  • Emphasized aligning interests: “the partners’ personal balance sheets are the thing that matters” (05:10).

2. Portfolio Construction Philosophy

• Endowment-Style Allocation with Personal Risk Appetite
  • Asset mix: 40% public (beta), 12.5% each to PE, VC, and real estate, 5% idiosyncratic (company building), 6% digital assets, 10% private credit (05:50).
  • Evolving allocations: annually reassess capital market assumptions, building increasing confidence in certain asset classes (06:59).
• Vintage Discipline & Market Timing Skepticism
  • Use of “annual vintage funds” to ensure consistent exposure—prevents ill-timed market swings (09:20).
  • Core belief: “Market timing is really hard… every time I forget it, I get burned.” (42:06)

3. Avoiding Institutional Pitfalls

• No Principal-Agent Problem; Full Alignment

  • Every investment committee decision is made with the explicit intent of personal outperformance—not reputation management (05:06).
  • “It is encouraged in our investment committee for partners to pound the table and say, I do not want this in my personal… portfolio.” (05:18)

• Diverse Views & Groupthink Antidote

  • Contrarian views are valued: investment committee avoids groupthink by debating personal capital at risk (05:26).

• Contrast with Endowment Mindsets

  • Claims principal-agent, groupthink, misaligned incentives, and risk-averse culture pervade even top endowments (13:25).
    • “I care a heck of a lot more about my kids’ trust funds than I do the school’s endowment.” (14:10)
  • Institutions slow to embrace high-conviction investments (e.g., digital assets) despite personal beliefs of decision-makers.

4. Lessons from Mistakes and Evolution

• Brand Name Trap & FOMO

  • Early mistakes: investing with “big brand” funds for defensibility, not conviction (19:09).
    • “Our biggest mistakes have come when we… had fear of missing out because… we felt lucky to get into a big brand.” (19:24)
  • Learning: as funds’ AUM grew, returns inversely correlated; now more methodical about manager selection and wary of increasing manager size (20:50).

• Refinement of Manager Allocation

  • Approach: Target “a third, a third, a third” across market leaders, breakout managers, and emerging managers for each asset class (22:07).
  • Emphasis on early conviction and reallocation as managers’ fund sizes grow and alpha potentially declines.

5. Behavioral & Structural Edge

• Decision Making & Information Flow

  • Leverage investment products (“Lego blocks,” e.g., 25 internally created funds) to customize allocations (03:55).
  • Value of being a major LP/anchor: increases access to information, flow, and economics (30:25).
    • “Doing more diligence doesn’t enhance expected return—it just decreases the volatility.” (30:51)

• Lean Team & Reluctance to Scale Headcount

  • Noted tradeoff: conservative hiring can limit ability to scale conviction even when more resources could improve outcomes (26:40).

• Negative Alpha & Information Diet

  • Avoids negative information by limiting news, social media, and seeks high-quality, curated content (38:39).
    • “I don’t read news. The important things will get to me… it actually filters out a lot of bad news and noise.” (38:45)
    • Heavy use of podcasts for curated, thoughtful insights (40:41).

6. Memorable Quotes & Moment Highlights

On Investing Your Own Money vs. Institutions

• “We make an investment because we want our personal money into it or not.” — Alex (05:15)
• “I care a heck of a lot more about my kids’ trust funds than I do the school’s endowment.” — Alex (14:10)

On Portfolio Construction & Market Timing

• “We are targeting the highest possible expected return with the highest possible Sharpe ratio… managing toward the efficient frontier is the underpinning of every decision that we make.” — Alex (07:10)
• “The maxim of—market timing is really hard. Every time I forget it, I get burned.” — Alex (42:38)

On Behavioral Biases in Committees

• “That’s one of the problems with committee-based decision making… the psychology of committees I think is interesting.” — Alex (34:05)
• “You should never have to defend any one manager selection...if your portfolio is delivering 15% for 15 years no one should question that one manager.” — David Weisburd (33:44)

On Information Diet & Decision Quality

• “Some of the worst things that you’ll ever do… is by getting bad advice from people. It is certainly not positive or neutral.” — David Weisburd (40:00)

Notable Segment Timestamps

| Timestamp | Segment Description | |-----------|--------------------| | 00:06 | Origin story: Endurance’s hybrid entrepreneurial/investment approach | | 03:55 | Creation of 25 bespoke fund products—“Lego blocks” of allocation | | 05:06 | Investment committee: alignment, absence of principal-agent problem | | 09:20 | Avoiding market timing—annual vintage discipline | | 13:15 | Institutional principal-agent issues summarized | | 19:09 | Analysis of mistakes: overconfidence in “big brand” managers | | 22:07 | “A third, a third, a third” framework for fund selection | | 26:09 | Shift to collaborating with outside capital for anchor investments | | 30:25 | Information & deal flow benefits of anchoring managers | | 38:39 | Alex’s information diet—news abstinence and podcasts | | 42:06 | His biggest investing mistake: attempted market timing during COVID |

Final Note of Advice

Timeless Advice from Experience

“Don’t try to market time… Market timing is really hard and every time I forget it, I get burned. Vintage discipline is deeply built into our structures because it’s such a natural human emotion to think that you know something. But very rarely can people do market timing well.” — Alex (42:06)

Tone and Language

The conversation is candid, practical, and behavioral—eschewing jargon or posturing for authentic, under-the-hood insights. Both guest and host combine thoughtful skepticism with a willingness to question mainstream investing norms.

For Listeners: If You Missed the Episode

This episode is a must-listen for anyone interested in how top-tier family offices succeed by thinking and acting differently than institutions—eschewing groupthink, embracing true diversification, seeking authentic information flow, and keeping their incentives ruthlessly aligned with outcomes. The actionable lessons on portfolio construction, manager selection, and information hygiene are directly applicable to private investors and institutional stewards alike.