Capital Allocators – CIO Greatest Hits: Multi-Family Offices – Jenny Heller 2021 (Brandywine)

Podcast: Capital Allocators – Inside the Institutional Investment Industry
Host: Ted Seides
Guest: Jenny Heller, CIO, Brandywine
Date: August 25, 2025
Episode Focus: An in-depth discussion with Jenny Heller about the evolving investment process, team dynamics, and strategic thinking in the context of managing multi-family office portfolios.

Episode Overview

This episode, part of a summer CIO "Greatest Hits" series, revisits and updates a wide-ranging conversation between Ted Seides and Jenny Heller, CIO of Brandywine, a boutique multi-family office. Heller reflects on how her investing approach, team processes, and philosophy have evolved, emphasizing the importance of a beginner’s mind, deep dives into new asset classes, and balancing creativity with discipline. The episode provides a masterclass in institutional investment research, team management, decision-making frameworks, and the nuanced art of capital allocation for wealthy families.

Main Discussion Points & Insights

Jenny’s “Beginner’s Mind” Approach

• Genius lies adjacent to weakness or eccentricity ([07:10])

  • Heller attributes her strength to “approaching everything with a beginner’s mind,” helping her stay fresh, connect dots in unusual ways across asset classes, and maintain humility.
  • Quote:

    “It allows me to keep fresh and love my work. And I think it also allows me to bring a lot of humility to what we do. Sort of a restless humility where I’m humble about what I don’t know.”
    — Jenny Heller ([07:22])

• However, this humility can backfire as she sometimes hesitates to stand firm in her beliefs or changes her mind late in investment debates, which can be frustrating for her team.

Sourcing and Deep Dive Research Process

• Broad Sourcing with First-Principle Constraints ([08:56])

  • Brandywine uses “gating questions” to focus ideas and maintain innovation within defined parameters.
  • Central to sourcing: clarity of vision, durability of strategies, and preparation for "deep dive" investigations led by team members’ passions.

• Deep Dives—Example: Affordable Housing Bonds ([10:57])

  • Team members explore complex areas in depth ("discovery, connect, identify"), mapping industries, talking to stakeholders, and identifying the investment universe—even if no actionable investment results.
  • Quote:

    “He refers to the research process around a deep dive as discovery, connect and identify.”
    — Jenny Heller ([11:46])

• Balancing Research and Productivity

  • Deep dives must hypothesize a potential investment from the start and are prioritized annually as a team. Most team members do one or two per year. ([13:05])

Case Study: Entering Crypto

• Crypto Deep Dive ([14:33]–[18:47])
  • The team entered crypto research despite initial skepticism, driven by curiosity, evolving team interest, and the logic that to learn, sometimes you must have “skin in the game.”
  • Focus shifted from “store of value” to real-world use cases (DeFi, next-gen payments, Web 3.0).
  • Quote:

    “We just decided that this was like the Internet in the 1990s and we had to dive in at some small level to really fully understand what we didn’t know.”
    — Jenny Heller ([17:48])

  • Brandywine invests exclusively through managers, never directly:

    “We are not experts in many things. I think we are really, really good at picking people to partner with.” ([18:05])

Sizing Investments & Portfolio Construction

• Phased Sizing ([18:57], [29:53])
  • Investments start small, with explicit "Key Diligence Indicators" (KDIs) to justify scaling up. Venture investments remain small by nature.
  • The team once under-sized positions, then over-corrected and over-sized, learning to balance gradual scaling with flexibility:

    “I think when I came to Brandywine, my instinct was to want to size everything too small...I went to the other extreme for a little while...Now...we’ll typically start at a half-size position, even if it’s a manager we know pretty well, with a pathway toward growing that position…”
    — Jenny Heller ([29:53])

Decision-Making, Team Dynamics, and Frameworks

• Learning from Mistakes & Team Composition ([32:04])
  • Lessons learned:
    • Beware overcomplexity: Focus on core factors like alignment, team dynamics, and process.
    • Use frameworks (1–5 scale, no 3s) to force nuanced, data-driven debate.
    • Adapt team composition as the organization matures, focusing on collaboration, humility, and avoiding ossified bureaucracy.
  • Quote:

    “Complexity can be okay. It’s something I am much more wary of than when I started...If we’re going to take on something complex, we can’t forget just about the basics of alignment, team and process.”
    — Jenny Heller ([32:22])

  • Assessment and diligence process includes clear hypothesis testing via KDIs; investment decisions ultimately reside with the MD and Jenny, not a consensus.

Research & Underwriting Process

• Diligence Mechanics ([38:40])
  • Research begins with team or director interest, early reference calls for mosaic-building, and an “issue memo” reviewed by all. Then a tailored research plan follows, often across 15+ meetings or calls, especially with new managers.
  • Decision is collaborative, but not consensus-driven:

    “I am not a believer in consensus decision making. So we aim to have a process that’s highly collaborative, where we can gather as many viewpoints as possible.”
    — Jenny Heller ([41:15])

Market Environment & What Excites Jenny

• Current Outlook ([42:12])

  • “I’m not super excited about all that much right now. What I’m excited about is that we have oriented our portfolio for many years towards quality and… businesses that can compound their earnings through cycle and… have a lot of ways to win...”
    — Jenny Heller ([42:20])

• Contextualizes the uncertainty (inflation/deflation, China, pandemic), re-committing to quality and durable, customer-centric businesses.

Team & Manager Culture

• Evolving Views on Talent ([43:49])
  • Shifted from “rockstar PM” focus to deeply analyzing manager culture, especially founder dynamics and how teams interact under stress.
  • Memorable Moment:

    “It’s an intensely human business investing and the pattern recognition that comes from doing it for a long time is to be able to sort of dive underneath what you see initially… to see how [teams] are behaving towards each other.”
    — Jenny Heller ([44:48])

Notable Quotes & Memorable Moments

• On the value of a beginner’s mind:

  “Sort of a restless humility where I’m humble about what I don’t know. But I also am never satisfied with the status quo.”
  — Jenny Heller ([07:22])

• On sizing errors:

  “When that position does something you don’t expect...it puts huge pressure on the internal process, and a lot of pressure on your relationship with a manager because there’s just no wiggle room.”
  — Jenny Heller ([30:28])

• On decision processes:

  “The MDs hold themselves to an exceptionally high bar...sometimes we’ll acknowledge this is an unknowable that we’re willing to live with and it will impact our sizing decision.”
  — Jenny Heller ([41:15])

Timestamps for Key Segments

| Timestamp | Segment Description | |-----------|-------------------------------------------------------| | 07:10 | Jenny’s “beginner’s mind” and humility | | 08:56 | Sourcing and use of gating questions | | 10:57 | Deep dives—affordable housing example | | 13:05 | Approaching team-driven research deep dives | | 14:33 | Deep dive in crypto – process and lessons | | 18:05 | Manager selection approach; not direct investing | | 29:53 | Sizing investments and learning from mistakes | | 32:04 | Evolving views, team dynamics, communication | | 38:40 | Institutional research and due diligence process | | 41:15 | Investment decision-making framework | | 42:20 | Market environment: excitement and caution | | 43:49 | Team & manager culture, evolving lens |

Closing Rapid-Fire Q&A Highlights

• Favorite hobby: Skiing (outdoor), reading (indoor) ([47:08])
• Most important daily habit: Singing and reading to her kids ([47:14])
• Personal pet peeve: “People forgetting the humanity of others.” ([47:36])
• Investment pet peeve: Misalignment and broken promises ([47:53])
• Biggest career influencers: Bill Peterson and David Patterson ([48:09])
• Key life lesson: Learn to be intentional with time ([49:28])

Takeaways

• Mastery in capital allocation involves balancing creativity and discipline, deep research with clear frameworks, and continuous evolution of team processes and culture.
• Jenny Heller’s willingness to revisit assumptions, embrace risk thoughtfully, and center human factors in both team management and manager selection offers valuable lessons for both institutional and individual investors.

For more: Visit capitalallocators.com for the full episode archive and show resources.