Mar 10, 2025 · 1h 4m · capital-allocators
Shannon O'Leary – Relationship Capital Investing at St. Paul & Minnesota Foundation (EP.435)
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this episode of Capital Allocators, host Ted Seides interviews Shannon O'Leary, Chief Investment Officer of the St. Paul & Minnesota Foundation, exploring her relationship-driven investment philosophy, radical candor in manager selection, and strategic governance overhauls. O'Leary details how she leverages roles-based asset allocation, deep cultural due diligence, and authentic stakeholder communication to steward a $1.8 billion community endowment.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Ted holds 21.3% of the talking time here. How this is scored →
Ted as informed peer 3.6 Guest teaching 3.3 Guest disagreement 0.4 Ted pushing back 0.1
speaking balance: gold is Ted, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 42:50 Blunt Confrontation Over Disrespectful Committee Presentation
O'Leary describes explicitly telling a senior fund co-founder that he embarrassed her, wasted the committee's time, and ruined confidence in his succession plan by talking over his successor.
Hardest push from Ted ▶ 46:15 Challenging the Definition of Manager Value Beyond FeesThe host nudges O'Leary past table-stakes economics, gently teasing her about smaller ticket sizes and prompting her to define the foundation's non-monetary value.
Biggest teaching moment ▶ 36:25 Exposing Jargon and Hidden Risk Management DeficitsO'Leary demonstrates how bringing a non-finance person into meetings stripped away obfuscating jargon and exposed that a hedge fund had an unempowered risk manager.
Ted holds their own ▶ 53:10 Validating Private Market Pacing and Commitment CliffsO'Leary cites the host's own newsletter analysis on 2025 private market pacing and mark freezes, validating his perspective on uncalled capital overhang.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Ted as informed peer | Guest teaching | Guest disagreement | Ted pushing back | Why |
|---|---|---|---|---|---|---|
| Guest Overview: Introducing Shannon O'Leary | 0 | 0 | 0 | 0 | Host monologue introducing guest Shannon O'Leary, outlining her background in family offices and the St. Paul & Minnesota Foundation, alongside housekeeping remarks about video podcasting. | |
| Early Life, Family Roots, and Formative Adversity | 3 | 3 | 0 | 0 | O'Leary shares her formative childhood experience coping with her father's early-onset dementia and how it forged her rapid honesty and acute sense of mortality. The host provides an empathetic space with brief, open prompts. | |
| College Exploration and Broad Academic Horizons | 3 | 2 | 0 | 0 | O'Leary recounts her college experience at UW-Madison, exploring a diverse curriculum spanning physics, economics, and humanities. The dynamic is purely biographical and conversational. | |
| Early Career in Asset Management and Fast-Track Responsibilities | 4 | 4 | 0 | 0 | O'Leary explains how she built executive presence early in her career when thrust into client presentations. She breaks down tactical body language and voice habits like eliminating uptalk and taking up physical space. | |
| Transitioning to Family Office and Allocator Career Trajectories | 4 | 4 | 0 | 0 | O'Leary describes moving to a family office and learning to translate investment jargon for non-financial family members. She emphasizes mirroring body language and advocating for non-financial stakeholders in meetings. | |
| Reading People and Assessing Manager Authenticity | 4 | 4 | 1 | 0 | O'Leary outlines how she reads manager authenticity and tests long-term cultural alignment. She highlights using relationship capital to deliver constructive feedback when presentations falter. | |
| Joining St. Paul & Minnesota Foundation and Philanthropic Mission | 3 | 3 | 0 | 0 | O'Leary explains the recruitment process and mission of the St. Paul & Minnesota Foundation. She details balancing social grantmaking, concessionary loans, and traditional endowment investing. | |
| Rebuilding Governance and Transitioning from Consultant-Led Model | 4 | 4 | 0 | 0 | O'Leary details repairing organizational trust and shifting governance from an outsourced consultant-driven framework to an internal staff-led model. She outlines methods for empowering committee fiduciaries through clearer decision framing. | |
| Roles-Based Asset Allocation and Degrees of Freedom | 4 | 3 | 0 | 0 | O'Leary breaks down her roles-based asset allocation approach into growth, diversifying, and real assets buckets, highlighting built-in degrees of freedom using an ag credit investment example. | |
| Aligning Manager Capabilities with Portfolio Needs | 3 | 3 | 0 | 0 | O'Leary discusses how managers should engage allocators outside of active fundraising cycles to establish complementary fit rather than purely transactional sales pitches. | |
| Conducting Multi-Layered Diligence and Evaluating Culture | 4 | 4 | 1 | 0 | O'Leary shares an unconventional diligence experiment where bringing her teenage daughter to meetings disrupted rehearsed manager jargon and forced transparent answers regarding risk management shortcomings. | |
| Addressing Industry-Wide Succession Planning Challenges | 3 | 4 | 1 | 0 | O'Leary comments on industry-wide founder succession vulnerabilities, pointing out how frequently aging founders stumble through succession planning despite strong junior talent. | |
| Case Study in Constructive Feedback: The Investment Committee Debrief | 4 | 4 | 1 | 0 | O'Leary recounts a direct debrief with a veteran founder whose poor presentation and talking over his designated successor embarrassed her in front of her committee, showing how blunt feedback preserved the relationship. | |
| Managing Performance Lapses and Termination Protocols | 5 | 4 | 1 | 1 | The host gently probes what managers want beyond capital, prompting O'Leary to explain how honest allocator communication and willingness to facilitate open staff discussions bridge the allocator-manager divide. | |
| Leveraging Capital Stickiness at the Two-Billion-Dollar Scale | 4 | 3 | 0 | 0 | O'Leary explores how mid-sized foundations offer sticky capital that appeals to managers diversifying away from consultant concentration, alongside the foundation's reputational value. | |
| Sourcing Emerging Talent and Building Network-Driven Pipelines | 4 | 3 | 0 | 0 | O'Leary explains how she sources emerging and niche managers using peer allocator networks while anchoring portfolios with established core managers before branching into specialized satellites. | |
| Public Market Benchmark Distortions and Donor Education | 5 | 4 | 1 | 0 | O'Leary laments benchmark distortions created by tech mega-cap concentration and explains the difficulty of educating non-profit partner CFOs and donors about illiquid mark lags. | |
| Assessing Market Volatility, AI Capex, and Opportunity Sets | 4 | 4 | 1 | 0 | O'Leary critiques AI capex requirements and past private market 'volatility laundering', expressing appetite for renewed market volatility to uncover genuine alpha opportunities. | |
| Pet Peeves, Family Surprises, and Raising Teenage Boys | 3 | 2 | 0 | 0 | The interview concludes with lighthearted reflections on calendar-invite pet peeves, raising teenage boys, and upcoming foundation leadership transitions. |
Statements from this episode (42)
O'Leary: Professionals often mistake rapid honesty for bluntness
“I think that people mistake Rapid honesty with bluntness. And my goal in communication is let's not beat around the bush. We don't know what's going to happen next. We're planning for a long-term relationship with manager ABC. We're planning for these assets t…”
O'Leary: Closed body language in presentations makes audiences uncomfortable
“Take up more space, and the smaller you are, the more space you need to take up, because you're making the audience uncomfortable, even if you don't know that you are.”
O'Leary: Eliminating uptalk is essential for projecting authority
“And so if you want folks to trust you and take what you're saying authoritatively, can't have the uptalk. Got to salt that out of there.”
O'Leary: Presentation skills differentiate career analysts from senior leadership
“Things that differentiate individuals who are gonna be a perfect analyst forever do include that presentation ability, that executive presence, and frankly, that desire. Managing people is hard. Managing sideways to your executive leadership peers is work. Man…”
O'Leary: Jettisoning investment jargon engages non-financial stakeholders
“And probably the most successful thing I ever did was attempt to jettison as much of the investment industry lingo as I possibly could, because it was really clear to me that when the investment person comes in and starts talking, people get out their phones b…”
O'Leary: Manager behavior reveals investment process and partnership fit
“If you don't spend a little of that time getting to know folks, understanding how they think, how they operate, that not only informs their investment thought process and how they treat their staff, how they approach their underlying assets, it's a really good…”
O'Leary: Direct LP feedback to founders relieves internal IR teams
“And generally what I find with those tough conversations is that this is a huge relief for the IR staff and the business development professionals is they know what the issues are. They would rather they have an allocator come in and be like, hey, I know what …”
O'Leary: Saint Paul Foundation is Minnesota's largest community foundation
“So St. Paul Minnesota Foundation is one of many community foundations in the state. We are the largest. We are statewide, which is a bit unique.”
O'Leary: Foundation ensures endowment investments align with grant making
“And we are also very intentional and active in that portfolio about ensuring that the investments and the managers that we're choosing there Are not invested in ways that are in conflict with our grant making.”
O'Leary: Foundation investment team turned over 100% twice before her arrival
“I came in after the investment team had essentially turned over a hundred percent twice.”
O'Leary: Foundation shifted from consultant-driven to team-led investment model
“What I came into was functionally a very consultant-driven model, and we had an opportunity to shift from that consultant-driven model to a team-led approach. Which is what we've done.”
O'Leary: Engaging disengaged boards requires private wealth management communication skills
“The skills are exactly the same, because all of it is talking to the human's head. Whether you're in a board member who tunes out when the investment person starts talking, or you're the non-financial spouse, those are the same responses, and I'm going to use …”
O'Leary: Philanthropic foundations often disconnect grantmaking from endowment investments
“At the time, too, there was also not a lot of connective tissue between the grant side of the house and the investment side of the house, and I think that's pretty common in philanthropy to see.”
O'Leary: St. Paul Foundation uses a roles-based asset allocation framework
“We ended up shifting from the bucketed model to a roles-based allocation, which is almost like a total portfolio approach. And so we've got our growth allocation, we have our diversifying assets, and then we have a real assets allocation.”
O'Leary: Foundation allocates 65% to growth assets to fund 5% spending
“On the gross side though, because we're trying to support at five percent spending policy while offsetting inflation over time, that's always going to be the biggest chunk of this portfolio. It is a big risk budget. So, 65% where we're seeking higher return, a…”
O'Leary: Foundation maintains a fifty-fifty liquid to illiquid asset split
“We don't have the flexibility of, say, a college endowment, so you've got to have enough liquidity built in there, and then obviously we're looking for that return. That bucket is probably fifty-fifty in terms of liquid versus non-liquid.”
O'Leary: Meeting allocators outside fundraising enables non-transactional relationships
“What I appreciate is when folks come in when they're not fundraising, it sets up a fundamentally non-transactional relationship, or can, obviously not always.”
O'Leary: Foundation manager diligence takes at least six months
“A diligence process from when we meet you to when we make an investment decision at the fastest is six months.”
O'Leary: Allocators learn most about firms from non-executive staff
“And we learn a lot by interviewing not the top brass. You can learn a lot about a firm by how they treat the staff.”
O'Leary: Having managers pitch a teenager exposes their true character
“What was so interesting to me was the shift in language, the shift in how they talked about the strategy, the degree of care and interest in explaining it to a seventeen-year-old revealed A lot about the nature of the people that I was meeting with, some of wh…”
O'Leary: Hedge funds must have empowered risk managers to discipline traders
“You need a risk manager at a hedge fund, someone who oversees all of it and understands positioning and is willing to take trader's To task. One, you need to have the right person. Two, you have to empower that person.”
O'Leary: Diligence pauses immediately if a manager dodges a question
“The experience gets baked into the process by us ensuring that if I don't get an answer, There's two other folks on this relationship that are gonna ask the same question, point out that it hasn't been answered, and it basically empowered us to be a lot bolder…”
O'Leary: Getting managers to reveal concealed truths is 90% of diligence
“I think holding people's feet to the fire on tough stuff, like the conversation around the succession planning, those conversations where this is a safe venue for us to talk about hard things and really having managers understand that, and then feeling empower…”
O'Leary: Many aging fund co-founders lack robust succession planning
“There's a lot of co-founders out there in their sixties and seventies. Some have done robust planning. Many have not. A few have attempted some planning and then had to back up the truck and start over again a few times.”
O'Leary: Founders talking over new CIOs destroys succession confidence
“And I said, when you do that, zero LPs in the room believe that you have a succession plan.”
O'Leary: LPs should stick with founder issues if next-gen leadership is better
“The reason you decide to work through that situation is the next tier of leadership is excellent. Their overall investment process is actually even better than the original co-founders.”
O'Leary: I have ordered fund CIOs to stop talking during diligence
“There's been meetings where I've invited the chief investment officer of an organization to stop talking because he's being significantly less effective than I think if I heard from the staff.”
O'Leary: A communication void exists between allocators and managers
“There's a communication void between, I think, the allocator community and the managers. The IR folks generally are pretty well aware of what that gap is. It's that they have a hard time, I think, sometimes solving for X with whoever the investment professiona…”
O'Leary: Many allocators refuse to share pacing schedules with managers
“So I bump into allocators who do not provide managers with any information of any kind. They don't want to say what they're looking for this year. They don't want to tell a manager that your category is a priority or not a priority this year. They're not inter…”
O'Leary: Fund managers seek endowments for stickier capital
“They're looking to add endowment and foundation, which tends to be sticky, and particularly organizations that have an in-house team. Because then you're building the relationship directly with the client as opposed to going through an intermediary.”
O'Leary: Nonprofit LPs act as reputation laundering for investment managers
“Having nonprofits and squeaky wheels like myself on your cap table is a little bit of reputation laundering”
O'Leary: Foundation secures core anchor managers before adding satellite positions
“We're going to do some of the standard seasoned managers that are going to be In a lot of cases, core positions in most portfolios will have some of that, and I think that's a fine strategy to have, especially in some of the slices of the portfolio where we're…”
O'Leary: St. Paul Foundation will reduce commitment sizes in 2025 and 2026
“Obviously, our ticket size is going to be smaller in 2025 and probably 2026 as well.”
O'Leary: Private markets won't move until buyer-seller standoff resolves
“And I just think, until we resolve what still looks to me like a standoff between buyers and sellers, it's not gonna move.”
O'Leary: Forced liquidity will drive down private market marks
“I don't know that that's going to be the reality that gets experienced, and at a certain point, you're going to have to create liquidity. And it may mean that you're going to see marks coming down. It may mean that you see folks willing to show their hand on w…”
O'Leary: Big tech concentration affects global equity indices beyond the US
“In these large technology securities in the public markets that impacts all of the indices. It's not just the U.S. Indices. It's worked its way all the way through ACQUI-IMI.”
O'Leary: St. Paul Foundation manages assets for 200+ nonprofits
“We also manage assets for more than 200 nonprofits. We're effectively their outsource CIO.”
O'Leary: Foundation shifting to negative consent to access fast-closing funds
“One of the things that we're bringing through our committee is a shift from affirmative consent to negative consent.”
O'Leary: Foundation had zero access to constrained managers in 2019
“We did not have any access to constrained managers in 2019.”
O'Leary: I would love market volatility despite board aversion
“It's not a popular opinion that I would say to say like a board or a committee, but I would love some volatility.”
O'Leary: Private market outperformance in 2022 was merely volatility laundering
“Anybody with a private book looks like a genius, but really you're just a volatility laundering.”
O'Leary: AI is bubblicious and could trigger public market volatility
“AI is a little bubblicious. We started to see a little bit of the potential fall that can happen if it turns out the thesis of AI is that you have to spend a hundred and eighty billion dollars on chips every 18 months. If that's not correct, maybe some of that…”