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Shannon O'Leary

lines on the record: 83
first: 2025-03-10
most recent: 2025-03-10
sittings or episodes: 1
sources: podcast

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“Way the strategic allocation was put together. Very defined buckets, very narrow parameters on what Count says what. And the complexity of that. 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. Again, it gets back to people's discomfort. I think people are just naturally uncomfortable when the money people come in and start talking. Money and fear, like right next to each other and everyone's amygdala, apparently. And so my job is to change the language so we're open and inclusive. We're inviting board members in to have these conversations. At the same time, when you're doing that, you're building that relationship capital same way you would with a manager. Same way you would with a colleague or a staff member. The approach that I took was very hands-on, and I don't think there would have been any other way to do it.”
2025-03-10 · Capital Allocators · Shannon O'Leary – Relationship Capital Investing at St. Paul & Minnesota Foundation (EP.435) · IDENTIFIED FROM THE TRANSCRIPT · source
“And extremely busy lives. And how do you get their attention effectively? How do you keep their attention? How do you ensure that they feel safe and comfortable while they're getting informed enough to make a hard decision? And then you also need to pay attention to the dynamics of the committee or the board itself. So how do we put this group of people in the best position so that the dynamics are favorable to them successfully making decisions together? So from an internal and immediate board and committee perspective, my role was really to go on a mission of trust and grace. You're spending time one-on-one. You're being a keen observer of how folks are operating in the room. Watching the committee have a very hard time on the decision making front because of the”
2025-03-10 · Capital Allocators · Shannon O'Leary – Relationship Capital Investing at St. Paul & Minnesota Foundation (EP.435) · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, I like the challenge. Folks ask me, oh my gosh, this is a total shift for you. You're in philanthropy instead of in private wealth. The skills are exactly the same because all of it is talking to the human instead. 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 the same toolbox to re-engage both parties. I like to tell my team a lot of what our job is with investment committees is putting people who are fiduciaries in a great position to make amazing strategy and governance decisions. How do you do that? Here you have these individuals. They're parachuting in four times a year for board meeting, four times a year for an investment committee meeting from their regular.”
2025-03-10 · Capital Allocators · Shannon O'Leary – Relationship Capital Investing at St. Paul & Minnesota Foundation (EP.435) · IDENTIFIED FROM THE TRANSCRIPT · source
“Which is what we've done. And as part of that, we got to work through a whole series of governance and strategy steps with the committee that put us all on a better footing to make better decisions”
2025-03-10 · Capital Allocators · Shannon O'Leary – Relationship Capital Investing at St. Paul & Minnesota Foundation (EP.435) · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, it was a little bit of a bumpy ride, Ted. So I came in after the investment team had essentially turned over 100% twice when those kinds of things happen. There's relationship capital that is fundamentally broken and in need of fixing. And so upon my arrival, my highest priority was really building and fixing those relationships internal, external, boards, committees, structure, and then getting to know the different committees and understanding sort of what their needs are was a really high priority for me because very substantially informs what your next steps are as the head of the investment team. What I came into was functionally a very consultant driven model. And we had an opportunity to shift from that consultant driven model to the team.”
2025-03-10 · Capital Allocators · Shannon O'Leary – Relationship Capital Investing at St. Paul & Minnesota Foundation (EP.435) · IDENTIFIED FROM THE TRANSCRIPT · source
“Intentional and active in that portfolio about ensuring that the investments and the managers that were choosing there are not invested in ways that are in conflict with our grant making.”
2025-03-10 · Capital Allocators · Shannon O'Leary – Relationship Capital Investing at St. Paul & Minnesota Foundation (EP.435) · IDENTIFIED FROM THE TRANSCRIPT · source
“So same poem and stone foundation is one of many community foundations in the state. We are the largest. We are statewide, which is a bit unique. The role of a community foundation is to we play a critical coalition building role with charitable capital where we aggregate charitable capital and then we help it get invested in the community. Investments can be things like grants, which are an investment that has a purely social return and no financial return. Investments can also be things like concessionary loans, where you're looking for a modest financial return while also amplifying your social impact as an organization to think of your traditional multi-asset endowment portfolio, which we do manage on my team, where you're looking for the financial return in order to support that 5% spending policy while offsetting inflation over the long term. And we are also very...”
2025-03-10 · Capital Allocators · Shannon O'Leary – Relationship Capital Investing at St. Paul & Minnesota Foundation (EP.435) · IDENTIFIED FROM THE TRANSCRIPT · source
“And they offer you the job, you don't say no. Plus, it's St. Paul Foundation. St. Paul, Minnesota Foundation has been in my life and community. And we've seen and benefited from the work of the organization over the many years. And so it's an honor to serve my community so directly.”
2025-03-10 · Capital Allocators · Shannon O'Leary – Relationship Capital Investing at St. Paul & Minnesota Foundation (EP.435) · IDENTIFIED FROM THE TRANSCRIPT · source
“So I had thought maybe I would go work in philanthropy at some point in my career. I was planning to work in the for-profit space for the duration of having to put my four children through college. And so I was not looking, I had an ownership stake in the firm, a friend of mine who knew I would potentially be interested in working in philanthropy in the future. Showed me the job posting and it was like, hey, isn't this your dream job that you thought about doing in the future? I was like, well, yeah, I am tot. But I'm a big believer and I tell my staff this all the time. You have to interview. It's a skill. So following my own advice, I submitted an application. And I think 11 interviews later and a full day trip to the shrink.”
2025-03-10 · Capital Allocators · Shannon O'Leary – Relationship Capital Investing at St. Paul & Minnesota Foundation (EP.435) · IDENTIFIED FROM THE TRANSCRIPT · source
“Issue is too can I have a conversation with this person who you've probably had this conversation with 16 times because it might be slightly more effective coming from a different lens.”
2025-03-10 · Capital Allocators · Shannon O'Leary – Relationship Capital Investing at St. Paul & Minnesota Foundation (EP.435) · IDENTIFIED FROM THE TRANSCRIPT · source
“That long term partnerships make it safe. When things go wrong The first call. That is of an enormous amount of value. It also puts us in the position, especially as firms go through founder transitions, transitions with underlying staff. Maybe they weren't particularly good at hiring people early on. They get a little bit better at it, but then they forget how to do the succession planning piece, or they just choose not to. Being able to go in and say to them, like, hey, look, we need to have a really serious conversation about how you just presented to my investment committee because you totally have egg on your face. And having the relationship there allows you to have that conversation in a more effective way where it's not necessarily confrontational. 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 the”
2025-03-10 · Capital Allocators · Shannon O'Leary – Relationship Capital Investing at St. Paul & Minnesota Foundation (EP.435) · IDENTIFIED FROM THE TRANSCRIPT · source
“Constantly have a pretty good radar for when I'm being lied to. I have a high attention to detail to when someone is repeatedly answering a question that I did not ask, but something that they would prefer to answer instead. And you can still pick it up in the body language, especially in person. It's also super helpful when you're establishing some of these long-term relationships. Most folks in my seat were looking at a 10-year relationship with a manager. I want to like you. I want to want to spend time with you because we're going to be spending a lot of time together. And 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 sign of.”
2025-03-10 · Capital Allocators · Shannon O'Leary – Relationship Capital Investing at St. Paul & Minnesota Foundation (EP.435) · IDENTIFIED FROM THE TRANSCRIPT · source
“So, if you transfer over to the investment side of those two disciplines, so reading people, understanding when people are listening, and then knowing what questions to ask if other people don't, how did you use that in your interviews with money managers?”
2025-03-10 · Capital Allocators · Shannon O'Leary – Relationship Capital Investing at St. Paul & Minnesota Foundation (EP.435) · IDENTIFIED FROM THE TRANSCRIPT · source
“I could then provide, I'm with you, I'm on your side. I'm going to ask that question that you're not going to ask because you don't think you know the language and you don't want to feel dumb. I'm going to ask that question.”
2025-03-10 · Capital Allocators · Shannon O'Leary – Relationship Capital Investing at St. Paul & Minnesota Foundation (EP.435) · IDENTIFIED FROM THE TRANSCRIPT · source
“When I was at the family office, I found myself on the side of the table as the non-financial spouse in a number of meetings And I began paying attention to sort of the vibe, what's going on there, you can tell when someone stops listening. You can tell when someone feels excluded or disengaged. It's not just a feeling. You can see it in their body language. And so if you sit and mirror that body language, it informs you that it's time for you to make a shift in your presentation and your behavior in order to re-engage this person. And the other thing that I would do is pre Identify a series of questions that I thought that the non-financial spouse should ask or might want to ask but didn't feel like they had the words. And so by sitting on the side of the person who feels the least informed when talking about investments.”
2025-03-10 · Capital Allocators · Shannon O'Leary – Relationship Capital Investing at St. Paul & Minnesota Foundation (EP.435) · IDENTIFIED FROM THE TRANSCRIPT · source
“Having a very high emotional quotient is extremely helpful. So, in all situations where you're dealing with individuals, whether or not they are foundation board member, foundation committee member, an individual family, a couple inevitably folks that you encounter are going to be the non-financial individual in the room. 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 there phones because they feel like this language, I don't understand this language. This is the part where I check my email because I'm not comfortable understanding what this means for my family. And so exiting that language and then inviting people to stay engaged is the secret sauce there.”
2025-03-10 · Capital Allocators · Shannon O'Leary – Relationship Capital Investing at St. Paul & Minnesota Foundation (EP.435) · IDENTIFIED FROM THE TRANSCRIPT · source
“So, there's sort of two aspects to succeeding in these environments. One is how are you dealing with the dynamics of the family or the client and then the other is the investment side? What did you learn about what it took to be successful in working with your clients in those environments?”
2025-03-10 · Capital Allocators · Shannon O'Leary – Relationship Capital Investing at St. Paul & Minnesota Foundation (EP.435) · IDENTIFIED FROM THE TRANSCRIPT · source
“After about five years there, I took a role at one of the large family offices in the Twin Cities area, so in Minnesota. There's an evolution that comes with moving from baseline roles in the industry towards the higher level allocator roles. There are some folks that I have managed that are going to be terrific analysts and associates forever. That's the right role for them. And things that differentiate individuals who are going to 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. Managing up to boards and committees isn't everyone's secret sauce.”
2025-03-10 · Capital Allocators · Shannon O'Leary – Relationship Capital Investing at St. Paul & Minnesota Foundation (EP.435) · IDENTIFIED FROM THE TRANSCRIPT · source
“I cannot stand up talk. So, a lot of folks have a little up at the end of every sentence. And so a lot of sentences then sound like questions like that. And they're not. And so if you want folks to trust you and take what you're saying authoritatively, can't have the uptalk. Gotta salt that out of there.”
2025-03-10 · Capital Allocators · Shannon O'Leary – Relationship Capital Investing at St. Paul & Minnesota Foundation (EP.435) · IDENTIFIED FROM THE TRANSCRIPT · source
“Observation and direct feedback, I think that combo is the most effective. So if I'm watching you present on a panel, if you use small body language, so you're hunched in the chair, you're slouched over, you're talking with your chin up, you're using closed body language, so you're holding your arms to your sides or together, your legs are crossed way too many times. My feedback for you is take up space. 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.”
2025-03-10 · Capital Allocators · Shannon O'Leary – Relationship Capital Investing at St. Paul & Minnesota Foundation (EP.435) · IDENTIFIED FROM THE TRANSCRIPT · source
“The ability to present with authority in a way that engenders trust and care. There are things that we do physically. With voices that can diminish the value of the very hard diligence work that you may have put into this memo that you're presenting to, say, an investment committee or a portfolio presentation to an individual of significant wealth. And so it's watching for those cues”
2025-03-10 · Capital Allocators · Shannon O'Leary – Relationship Capital Investing at St. Paul & Minnesota Foundation (EP.435) · IDENTIFIED FROM THE TRANSCRIPT · source
“Obviously, there's a little imposter syndrome. At that age, I'm sure what I was doing was faking it till I made it. And then I come, I think, because of my upbringing as an old soul, for better or for worse, informed by all of the things that have happened and then the learning that you get on the job. And I think that allows me come across with, I think, a hefty amount of executive presence.”
2025-03-10 · Capital Allocators · Shannon O'Leary – Relationship Capital Investing at St. Paul & Minnesota Foundation (EP.435) · IDENTIFIED FROM THE TRANSCRIPT · source
“The role was at first primarily focused on public securities. That firm managed both fixed income and equity portfolios. We also at the time had a lot of very large pension clients. And the dichotomy of the different types of conversations you would have with these very, very different clientele was eye-opening to me. At the time had a chief investment officer who was terrified of flying. And when that is your boss and there's a need for folks to be in a different location faster than you can take the train to Arizona. They're sending the junior person sooner. And so coming up that info curve was really hard but very stimulating to me at that age where you need to be able to go to a meeting and present. As if you are the senior person on the investment team.”
2025-03-10 · Capital Allocators · Shannon O'Leary – Relationship Capital Investing at St. Paul & Minnesota Foundation (EP.435) · IDENTIFIED FROM THE TRANSCRIPT · source
“Clearly into the investment industry somehow. I mean, I traded physics for investments. What I really enjoyed about that first role and what kept me in the industry was the intellectual stimulation. You get to look at new things all the time, whether you're analyzing individual securities. There are different ones to analyze. And then things change with them and you have to pay attention to all of that stuff. Then there's the alchemy of putting it all together. Then there's the intellectual adventure of Working directly with a board, a committee, individuals on their own wealth plans and investments, that's a challenge too. That is fun.”
2025-03-10 · Capital Allocators · Shannon O'Leary – Relationship Capital Investing at St. Paul & Minnesota Foundation (EP.435) · IDENTIFIED FROM THE TRANSCRIPT · source
“I feel like my first impression was, oh my gosh, I actually got a really good high school education. I am in a lot better of a position here than a number of my compatriots. And also they're really immature. Sort of the overall feeling. I spent a lot of time running marathons, just processing and running and running and running. I took everything under the sun that I could take that was intellectually stimulating to me. And that's how you end up with all the math classes, all the physics classes, all the econ classes. And then I'm taking a combined course that combines history, art, and language. As a symposium class and then enjoying it so much that I took three more.”
2025-03-10 · Capital Allocators · Shannon O'Leary – Relationship Capital Investing at St. Paul & Minnesota Foundation (EP.435) · IDENTIFIED FROM THE TRANSCRIPT · source
“Could not wait to go to college. And that was really the most immediate response of it was needing to just move on in order to process what had happened. So for me, going to college was the greatest thing that ever happened to me. So I went to the University of Wisconsin-Madison. It was amazing. I learned that I'd worked way too hard in order to get whatever I was getting in high school and I learned that I did not need to work that hard in order to achieve the same grades and then have more room to think and learn more. It was almost the freedom of coming out of that home situation and that degree of anxiety and sadness frees up a chunk of your brain that you didn't know was so occupied with what needed to happen in that moment every day in that situation”
2025-03-10 · Capital Allocators · Shannon O'Leary – Relationship Capital Investing at St. Paul & Minnesota Foundation (EP.435) · IDENTIFIED FROM THE TRANSCRIPT · source
“When you had that mindset. Thrust on you at that age. How did you begin to navigate this blend of wanting to think about your life and career early on need to be very present, need to act now, need to be very blunt because you don't know what's going to happen?”
2025-03-10 · Capital Allocators · Shannon O'Leary – Relationship Capital Investing at St. Paul & Minnesota Foundation (EP.435) · IDENTIFIED FROM THE TRANSCRIPT · source
“I think it infuses everything. I have a very high degree of constant awareness of my own mortality and that of everyone around me. I'm often accused of being blunt And 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 to be available to the community in perpetuity. But I'm going to tell you what information I need to convey to you or how I feel about it right now because the present can be very, very short.”
2025-03-10 · Capital Allocators · Shannon O'Leary – Relationship Capital Investing at St. Paul & Minnesota Foundation (EP.435) · IDENTIFIED FROM THE TRANSCRIPT · source
“As dementia progresses, you begin to see it. And I remember we saw signs of that eight, nine, ten, eleven years old. He was institutionalized when I was 12 and then passed when I was 17. And the five years in between there were marked by the progressive decline, the loss of himself. He disappeared as a person for us. And there's an inevitability while you're Over that period of time a teenager in high school and then also waiting for your father to die.”
2025-03-10 · Capital Allocators · Shannon O'Leary – Relationship Capital Investing at St. Paul & Minnesota Foundation (EP.435) · IDENTIFIED FROM THE TRANSCRIPT · source
“So, my mom was a science teacher, and my dad was an MD PhD researcher in aging at the University of Minnesota. So very science-y background. I'm not a whole lot of money in either one of those careers. So we lived pretty lean and lots of family in town, which was enormously valuable. Probably the formative experience of my early life is that my dad was diagnosed with and died from over a period of five years a degenerative frontal lobe dementia.”
2025-03-10 · Capital Allocators · Shannon O'Leary – Relationship Capital Investing at St. Paul & Minnesota Foundation (EP.435) · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, I had no interest or knowledge of the institutional investing industry until I got a job in the industry coming out of college. I'm from Minnesota. I grew up in St. Paul. I am one of five girls. So that's a very specific life lens to bring to all of the work. Let's just say that there was a lot of communicating and figuring out the nuances of what was really driving conversation. Also, I'll say that I don't know of many families where it was required that we needed to have the full set of encyclopedia Britannicas available to us next to the dinner table. So we were all aware of what the true facts were.”
2025-03-10 · Capital Allocators · Shannon O'Leary – Relationship Capital Investing at St. Paul & Minnesota Foundation (EP.435) · IDENTIFIED FROM THE TRANSCRIPT · source
“I guess on today's show is Shannon O'Leary, the chief investment officer of the St. Paul and Minnesota Foundation, where she oversees $1.8 billion for the Community Foundation that aspires to create an equitable, just, and vibrant Minnesota. Shannon took the post six years ago after 20 years working with families. She described herself as blunt, comfortably speaking her mind, including in her LinkedIn newsletter entitled Say It Out Loud. Our conversation covers Shannon's relationship-driven approach to investing across families, boards, team members, and managers. We discussed the value of frank communication in every aspect of the investment process, from setting policy to manager access, research, selection, and partnership.”
2025-03-10 · Capital Allocators · Shannon O'Leary – Relationship Capital Investing at St. Paul & Minnesota Foundation (EP.435) · IDENTIFIED FROM THE TRANSCRIPT · source
“Opinions expressed by TED and podcast guests are solely their own opinions and do not reflect the opinion of Capital Allocators or their firms. This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions. Clients of capital allocators or podcast guests may maintain positions in securities discussed on this podcast.”
2025-03-10 · Capital Allocators · Shannon O'Leary – Relationship Capital Investing at St. Paul & Minnesota Foundation (EP.435) · IDENTIFIED FROM THE TRANSCRIPT · source