Nova Chat with Elise Kennedy - Family Office Chief of Staff

Jeremy · 0:00

Hey, friends, welcome to episode 302 of The Leader Assistant Podcast. You can check out the show notes at leaderassistant.com/302. This episode features another Nova Chat from my friend Maggie Olson. And in this one, she chats with Elise Kennedy, who is a family office chief of staff. And they discuss what it's like holding an integral role with a family office and how Elise helped scale two companies in the past 12 years to a successful exit. I hope you enjoy this Nova Chat feature, and I've got a couple more coming up in the next few episodes. So thanks for listening and enjoy.

Speaker 2 · 0:45

The Leader Assistant Podcast exists to encourage and challenge assistants to become confident, game-changing leader assistants.

Jeremy · 1:03

Hey, Leader Assistants, have you heard the Nova Chief of Staff Certification course is about to see a price increase? But don't worry, you can enroll now, lock in the current rate, and start whenever you're ready with lifetime access. Nova's mission is to give you the ultimate student experience. They've packed the course with dozens of templates, self-paced learning, hands-on practice, multiple instructor touchpoints, peer engagement, and even guest authored assignments. With over 500 students across 22 countries, Nova is the top spot for Chief of Staff Learning and Development. Don't wait, enroll today and join the community at leaderassistant.com/nova.

Maggie · 1:49

Welcome. We've got Elise Kennedy here for our Family Office Chief of Staff Nova Chat. Super excited. We are doing more of these Nova Chats that really dive into specific Chief of Staff areas of support and journeys that are unlike ours or journeys that I'm unfamiliar with that I want to share with all of you. Welcome, Elise. How are you?

Elise · 2:12

I am great. I'm great. It's a beautiful day here in LA, technically Pasadena. I'm so excited to be here and so excited to hear about everyone's experience and what they're looking to do. I'm a little nervous to be among such accomplished people, but I'm really excited.

Maggie · 2:33

I told Elise not to be nervous. We're casual. It's easy. Don't worry at all. We're just thankful for you to share your expertise with us. I'm going to get going here. The goal of our Nova Chats is to really go deeper with industry experts and guests. We chat about job transitions and vulnerable moments, the do's and don'ts along the way, you're finding career alignment, when to move on and all of that good stuff. A little bit about Elise here. Elise is a Chief of Staff with over 12 years experience in consumer tech including two exits. I definitely want to talk about that. Currently, she's the Chief of Staff for a high net worth family office with investments spanning from entertainment production, luxury real estate, gosh, more than that to consumer technology and I think more. In this role, Elise oversees all operations and plays a key role in managing the family's office, basically the diversity of their portfolio. Elise's previous experience is vast and includes being the first hire at Olivia AI. We'll dive into that as well, which was later acquired by Warren Buffett-backed Newbank. She also served as the first business hire and head of product at Keat Health acquired in 2018 and as CEO of her own boutique consultancy firm for high growth startups, which is super, super cool. And she's been recognized in Crunchbase, TechCrunch, Mashable and Cheddar. Good places to be recognized. In 2016, this is fun. Elise was number one of the 27 pitches chosen out of 100,000 applicants on Apple TV's Planet of the Apps, where she pitched the app, Olivia AI, to industry figures, Gwyneth Paltrow, Jessica Alba and Gary Vaynerchuk. So pretty cool stuff. Elise lives in LA. Where outside of work, you'll find her roller skating, enjoying live music and hiking with her partner and their dog. So welcome, Elise.

Elise · 4:31

Thank you. Thank you. I'm so happy to be here.

Maggie · 4:33

Yeah. So fun. Okay. Well, we've got lots to dive into. I'm very excited. Why don't you tell us a little bit about, like let's rewind and tell us about how your early career got going. What were some of the threads like along the way that led you to where you are now? Where did you go to school? What were you studying? And then what was your first job out of school?

Elise · 4:55

Yeah. Yeah. Really good question. And so I'm from a small town in East Texas, where I learned how to code when I was 10. My brother kind of taught me how to code, just really basic HTML stuff. But for me, the Internet was the window to the outside world, to a great beyond. And so I was always just really into tech and the Internet. And so I went to school at Texas A&M, Giga Maggie's, where I majored in IT, Information Operations Management.

Maggie · 5:30

Yeah.

Elise · 5:30

And so right after that, I went straight into a very high growth startup, where there were like three of us, I think account managers did a whole lot of different stuff for at least 20,000 customers. And we provided 24-7 support. And so that's really where I got a boot camp into high growth startups.

Maggie · 5:51

What company was that, Elise?

Elise · 5:53

It was called at the time Columel, but I think it might now be called Textimal. But yeah, so we got on the Inc 500. Yeah. And so it's kind of my boot camp.

Maggie · 6:05

Yeah. Amazing.

Elise · 6:07

Yeah. Yeah. So from then, I've just always been involved in the startup world, doing a variety of different roles, everything under the sun. I always say that I tried to not get too under the hood with code. But everything from operations to product, anything that falls under the umbrella, that's not necessarily the super tech-heavy coding.

Maggie · 6:32

That's me. OK. So and how many jobs did it take for you to then go from that company to Olivia AI? Tell us the story there, the journey there.

Elise · 6:45

Yeah. So I was at Collimall and then I went to work for a non-profit in New York City that a friend had recommended me for. So I was there for four years doing anything from like marketing operations for the college. It was a small college in the heart of New York City. And then I was also doing startup consulting on the side because I still had my foot kind of in that door and in that world. That was just really passionate about what they were doing in the city and love New York. And so eventually, Olivia AI was someone who I had just had a connection with. And then they asked me to come on full time as they were raising their seed round.

Maggie · 7:30

Okay. And at what point in this journey, did you launch your own boutique consultancy as CEO?

Elise · 7:38

Yeah. So that actually came after my second exit.

Maggie · 7:42

Okay.

Elise · 7:43

And so someone else who had a really similar story to mine, but he was on the tech side of things, was a former tech stars. He had his PhD in computer science and had just sold his previous company. So he was doing kind of what I was doing on the side, just freelancing because other high growth startups were coming to be saying, hey, I really need help in scaling this thing. What do I do? And it just kind of turned into this. But there was the tech portion too, and there were a few people I actually trusted with that. And so he came to me and he said, hey, can we join forces? And that's kind of where we started from there. And so I started as a kind of BOO, basically, Director of Operations there. And one of our clients raised their Series A round of funding and then asked him to come on as their CTO. So he asked me to become CEO. And that's when I stepped up.

Maggie · 8:38

Okay. Okay. So I don't want to lose sight of kind of the early in career, the coding aspect. How did coding show up in your day to day in those early foundational roles that you took on for startups? What were you doing?

Elise · 8:52

That's a really good question. So the coding aspect of it, I didn't want to do as much because that required so much focus on that portion. But it was really helpful because there are things that actually ended up being super valuable, like knowing how to code HTML for e-mails, like e-mail marketing, which I'm still a huge fan of because you're not competing against algorithms. Then small edits too, you're not having to bug engineers for edits to a landing page for something or even a customer support page that you're building on your own. Small things like that were really helpful.

Maggie · 9:36

Have you heard? The Nova Chief of Staff Certification course price is going up in January of 2025. Enroll now and with lifetime access, start whenever you please. Here at Nova, it's our mission to provide the very best student experience possible. Our course is chocked full of features and resources designed just for you. Dozens of templates, self-paced online learning, hands-on practice, multiple instructor touchpoints, peer engagement opportunities, guest authored assignments, the list goes on. With 500 students across 22 countries, Nova is the premier destination for Chief of Staff Learning and Development. Enroll today and join us. Okay. Yeah, that makes sense. It's fun to hear a little bit about a unique background. I have a lot of friends who are engineers and deep in coding, and I think there's life lessons that you learn from coding, right? Patterns, systems, organization, the way that you look at the world. Do you feel like that's been impacted by your technical coding background at all?

Elise · 10:41

That's a good question. I think I learned patience because there's so many things that just break all the time when you're coding and so you just have to look things up on Stack Overflow and also learning like, hey, someone else use this template, let someone else use this code. I can copy and paste this into here and I don't have to recreate the wheel.

Maggie · 11:02

Okay. We talk about that a lot as Chiefs of Staff. So that's really...

Elise · 11:05

Exactly.

Maggie · 11:06

Exactly. That checks. All right. So let's get to where you started in Chief of Staff work and eventually Family Office work. So you went from the companies you've been talking about up to this point and then you started in Chief of Staff specific roles to startups. Is that right? Do you want to share a little bit more with us about that?

Elise · 11:30

Yeah. Yeah. So I think my journey's been pretty interesting, kind of working up slowly to the CEO role. And I realized, so I was asked to become CEO in January of 2020. And that's a crazy time to become CEO of a services-based company. And so I did that for...

Maggie · 11:50

For the consulting company, the boutique consulting firm for startups.

Elise · 11:54

For the consulting firm. Yeah. And so I was really proud of how we led the company through COVID, no layoffs, nothing like that. We really worked together to push forward. But I realized in that time frame, I'm going to be real, I was a good CEO. But I was more of a Robin than a Batman. And so I had realized, so my co-founder who had asked me to become CEO, who's formerly CEO, he was now CTO at this other company, there was a chief of staff there. And he said, I think, and it was a fairly new role. I mean, this is still kind of a new role.

Maggie · 12:37

Yeah.

Elise · 12:37

And so he said, I think-

Maggie · 12:38

What year was this, Elise? Sorry to interrupt, but what year was it?

Elise · 12:41

No, no. 2020.

Maggie · 12:44

Okay.

Elise · 12:44

2021, maybe. 21. And I've always been the de facto chief of staff. I'm sure a lot of people here can relate to that. You become like your principal's trusted person and special projects and they know they can hand it off to you and they know that you're going to do a good job and see it from start to finish. And so he told me about the chief of staff role. I was like, oh, that's really interesting. That really does seem up my alley. I started doing informational coffee chats with a few other chiefs of staff. I was like, oh, this is really my friend who was a chief of staff at Dropbox. And I was like, oh, this is really up my alley. Yeah, and so I knew someone in the FinTech space who was looking for someone kind of similar in that role at a company called Quill or Quinn. Yeah, and that's kind of how I officially got started with the title. Again, that was the first official chief of staff title.

Maggie · 13:50

Yeah. And what company were you chief of staff for? And then where did that lead from there to your next chief of staff role?

Elise · 13:56

Yeah. So I was chief of staff for, it was a venture-backed series, a fintech company called Quinn slash Quill. Basically doing a lot of stuff in the credit space for unemployed people. And so, yeah, basically taking that whole company from zero to 15,000 customers in the span of a couple months. And then, sadly, it had to shut down because when FTX happened, the FDIC for new financial products was like, we don't know what we're trying to regulate. We're going to halt all new products for all new financial products in the fintech space for the next at least six months. Like we're not going to do this until then. And so they said that to our banking partners and we're like, well, okay, that's that. And so that's kind of when I shifted to what I'm doing now.

Maggie · 14:55

Okay, so that led you to Family Office, to your role now in Family Office. Okay, we're going to dive deep into that. But before we do, why don't you tell us a little bit about the exits that you went through and the part that you took specifically in those exits in your de facto or actual chief of staff roles?

Elise · 15:14

Yeah, yeah, for sure. So I think the big thing that I always like to tell people who are scaling companies to exit is documentation is key, like absolutely key for two reasons. One is when you're scaling and you're scaling quickly, you find kind of that piece in the market and customers want it, they want it quickly. And being able to scale quickly and get more services out, have more customer service people coming on, creating more materials, creating more business verticals, having documentation so when you recruit the right people that come into your company, they can get on board super quickly. So typically, with documentation, I like to do two things. One is the typical writing out of processes of what exactly you've done from A to B to C on how to get on boarded in Zendesk. Here are how we respond to this. Here's how you get into these different networks and Plaid and all of that to refund money. Just all of these things so you can run smoothly and you can scale quickly. That and then using Loom. So that way, I'm using both the people that are visual learners versus the auditory learners. They can just go through a quick Loom video. So those are two big things. Then the other reason for documentation too, specifically when it comes to exits, is whoever is going to be acquiring you is going to be doing a lot of due diligence. From both the investors, as you continue to scale and do different rounds of funding, the investors and then the company themselves. And so for them to make the most return on their investment, they want to be able to hop in there and really understand what's going on. They want to make sure that when they look under the hood, when they look at your CRM, when they look at your financial modeling, revenue forecasting, all of these things, they really want to say, okay, this is a sound investment and we can trust that these people have their stuff together to where we can easily pick this up, and it's a very clear value add.

Maggie · 17:28

Yeah, that's super helpful. And specifically, what was your biggest part in those exits? Were you documenting? Were you filming looms? Were you the doer in a lot of that?

Elise · 17:39

Yeah, I think with the exits themselves, there's due diligence is a really big part of that, right? And so I think it's also like, typically it's the founders that are actually going and finding the person that's going to acquire it happens just in a few ways of their like networking for that, or if it happens kind of organically, it's happened in a little bit of both ways. And, you know, like IPOs, I haven't taken a company through an IPO since we are when we got acquired by Newbank, they IPO'd, I believe, two weeks after we were acquired.

Maggie · 18:16

Whoa, that's why.

Elise · 18:19

So we knew that was happening too. So that added this like whole other layer of things that I can only say so much about. But yeah, yeah. So that's kind of out in a nutshell.

Maggie · 18:33

Okay. Amazing. Well, super, super interesting. I want to talk about your job now in Family Office. So first of all, did you have your eyes set on Family Office, Chief of Staff work or how did this opportunity come about for you?

Elise · 18:50

No, no. I really, I knew some people who had worked in the Family Office world, but it's not something that I specifically targeted. Frankly, I was just kind of networking and I was looking for my next Chief of Staff role. I knew that's the role I wanted to stay in. And it's sometimes listed as several different things. I think this job might have technically been listed as Director of Operations. And so this role, I actually found online. It's funny because every single role that I've had, my entire career has all been networking, all been networking. But this one, I found through a job board. And it's so funny because I was so unsure of it because, and I'll get more into this later, but with family offices and a lot of these high net worth individuals, they do not have online presences at all. So you're like, what am I getting into? You try to do as much due diligence on your end as you can. But sometimes there's only so much you actually can do and you don't know it until you're into it. So I lucked out. I'm very grateful for that. But yeah, I wish I could have told my past self that it would be okay.

Maggie · 20:11

Oh, my gosh. So yeah, tell us a little bit about, I guess, all-encompassing family office work. What's your day-to-day look like? What's your scope? I know that we're going to be confidential around who you work for, of course. But share with us what it's like for you and what the job is like.

Elise · 20:30

Yeah. So a lot of people who are in family offices are interested in going into that. I always say the role can really vary depending on the family. Depending on the family and their net worth, and then especially their investments. Because some family offices almost operate like venture capital firms, and so they take people from the investment and VC space. But as you had mentioned earlier, the way that my family office works is it's basically a wealthy investor and his wife, and they're three different companies of luxury, real estate, consumer tech, and the production company in those day-to-day operations. It could really vary just depending on what the priorities are, and that's something that I know probably everyone here can relate to. But yeah, it's really interesting because you're working a log-side other ultra-high net worth individuals too, and so their priorities are really quickly changing. So it's like, oh, if one of them wants to make an investment or check on this one production, or an NFL player wants to come look at one of our properties, then things need to happen really quickly, but also be really high quality too. So it's balancing that matrix of what's urgent now and really important what's urgent long term and being strategic there. So yeah, it can really vary.

Maggie · 22:11

Yeah. Okay. So tell us that that makes a ton of sense. Tell us about the team. What is the Family Office team look like? We've got several Family Office Chiefs of Staff in the Nova Chief of Staff Certification course, and I get to meet with all the students and hear kind of the structure of their office. And I'm sure it can range hugely from, I'm the only one that's not in the family, to there's 10 or 20 of us. So what is the structure look like? And what are the other roles that are supporting the Family Office that you work with?

Elise · 22:40

Yeah, so really because we're small, we're small and we're lean for the Family Office themselves. So it's basically me and my boss and his wife for the Family Office umbrella itself. And then there's the three different companies, real estate and then the production company and then the consumer tech company. So and these umbrellas, they, I think he's technically the CEO of all of these, of all of these umbrella companies, if you will. And then there's a whole structure underneath each one of those companies.

Maggie · 23:16

Okay. And so you work with the CEO of each of those companies based on the direction and the need of your boss?

Elise · 23:26

Yeah. So my boss is the CEO of each company.

Maggie · 23:29

He's the CEO of each one. Okay. And so are you working within each company for your boss? Okay. And do you do anything outside of those three companies, like personal support or travel or things like that? It's pretty structured within the three categories. Okay. Yeah. And then he has teams, like large teams, small teams of people that also work within each of those companies.

Elise · 23:58

Okay.

Maggie · 23:58

Okay.

Elise · 23:59

Yeah. So the consumer tech companies, like 15 or so. And then the production company, the way a lot of production companies work is you have a lot of freelancers, but you still have some full-time people. But you have a lot of editors and stuff that you're working with. And then the people, the producers that you're working alongside. And then with the real estate too, you have your whole construction team. Without me giving away too much, you have your whole construction team, and then realtors and all of that.

Maggie · 24:30

Yeah. Amazing. Well, this is a good time to share with everybody on that. Feel free to pop questions into the Q&A box. The chat's a little harder for us to manage, but there's a Q&A box down there that you can find. Put questions in there. If you have specific questions, we will totally get to them. We're going to dive into a couple other things here, but we can come back to anything that you guys really want to touch on here. So, Elise, what qualities do you think are essential for success as a Chief of Staff of a Family Office? And then additionally, for people that are like, oh, that sounds pretty cool. I want to work for a Family Office. What kind of advice do you give to those folks?

Elise · 25:12

Yeah, that's a great question. So I think for Family Office life, what I mentioned, it can really vary. So if you're interested in the role, I think I would really narrow down as to what you're interested in doing. Because we're in a place where Family Offices can really vary, and then also Chief of Staff roles can really vary. So finding your own skills. So for me, I'm like an MBA type, consulting type, techie, and that's where my skills lie. Shout out to all the EAs, but I'd be terrible at Calendar Tetris. I'd be terrible at that. So I try to make that really clear in my interviews of where I can provide the most support in a lot of things and getting clear on what the Family Office needs too. So also what I said, getting a really good idea of what the Family Office does and where their investments are, so you can support those best. For me, I didn't know much about real estate when I got into this, and I was always intrigued by it. That was a cool growth opportunity for me to hop in here and really learn a lot about that aspect of investing. It's very different from tech. So I would think that those are for people that are looking into it for sure. It just depends on the role.

Maggie · 26:35

Yeah. I think it's pretty cool that you get to work in real estate, you get to work for production, like media, like that kind of a company. You have so much variety, which was what us Chiefs of Staff loves. We love variety, we love solving problems, we love change every day, doing something new. We love it. I think it's great. Right?

Elise · 26:54

It's so fun. It's so fun. It seems like the common thread I see is that humility and discretion for family offices, because you get to talk to a lot of cool people and interesting people every day, but they're just people at the end of the day.

Maggie · 27:11

Yeah.

Elise · 27:11

So that's really fun.

Maggie · 27:14

Good. So along those lines, what do you find is the most rewarding part about your work in family office and what's the most challenging?

Elise · 27:22

Yeah. So I guess the most rewarding part is I'll say, it's really cool being able to work for a principal who is wonderful, who's also personally invested in you, both literally and figuratively. And so that's really special. And so like yesterday, I was having a rough day. So he's like, let's go on a walk and grab coffee. And that was really special. And his, and since it's a family thing, and he and his wife, they have small children. And a lot of times just when schedules align, they'll come to the office and we still need to finish something. And so I'll pop them popcorn, we'll put on Disney Plus. And my boss and I will talk strategy at the conference table while they watch TV. So it's really sweet to like have that kind of relationship.

Maggie · 28:18

Yeah. Yeah. Okay. So happy Admin Day to everybody on the call who's an admin. I've never been an EA. I work closely with them. I advocate for them, but you guys are the real heroes. So happy, happy Admin Day to all of you. Do you work with an admin, Elise, in your current role? Does your CEO have an admin across the family office? Does he have an admin within each business? How does that work?

Elise · 28:40

So he has kind of an admin within each business, but that is something that's kind of a hot topic in our office right now, is working on getting that. Because it's really interesting because it's like, I'm always happy to do it. I'm a sweep the floor kind of girl. I'm like, if you need me to send a calendar invite, I'm totally fine with that. But at the same time, especially with the tech company, if I'm being positioned as a certain title in a certain area and trying to step into that power. But then if he asks me to send a calendar invite, people are like, wait, what's her role again? I'm confused. And so that's something that's on our like quarterly goals, is getting an admin type in there to help with that, even if it's part-time. Just with a lot of those, I don't know, just things like entering expenses and like my budget spreadsheet. And keeping track of those because when we have an admin, I know it won't just be like in the words of Chip Gaines, one plus one equals two. When you add that, it's one plus one equals 20. It's like a force multiplier.

Maggie · 29:46

I'm so surprised that you guys don't have an admin even across all three, like sharing the responsibility across the businesses.

Elise · 29:53

Yeah, exactly. And so, and since like a lot of it, I have such a great relationship with our accountant who does a lot of, a lot of the like really nitty-gritty. So when it comes to the day-to-day stuff, but yeah, hopefully we can get someone in there soon.

Maggie · 30:09

Cool. Okay. That's amazing. So with this, this is very relevant to our next question here. Usually there's admins, there's teams, there's people to do all the things, but you are in a way kind of like an office of one, and then you are within the three business categories as well. So when you don't have someone to call on or an expert to rely on, you did mention that you're a sweep the floor kind of girl, you're going to do it all. But we know that you aren't able to stay in the strategic space when you do that, and the positioning is difficult. So do you phone a friend a lot? Are you Googling, finding resources? Are you just doing it all? How do you find the answers that you don't have when there's so much and such a widespread of responsibilities to get done across all the businesses?

Elise · 30:58

Yeah, always phoning a friend, always. Always texting, hey, do you know this? Do you know someone that can help with podcast ad sales, like for post-read ads, because our contract with Audible is up and we don't want to continue with them. Just stuff like that, right? Where you're like, I don't know that and Reddit.

Maggie · 31:18

Yeah.

Elise · 31:19

Right. Yeah.

Maggie · 31:20

You're just finding resources. It's like part. It's like one of the chief of staff job descriptors. It's like resource finder.

Elise · 31:26

Exactly. Exactly.

Maggie · 31:29

Oh, my gosh. OK, so I think, you know, my last specific question into like the categories of the family offices and how do you how do you structure your day? I know that it kind of depends on the priorities, but there's a three very, very different businesses. And I imagine that it could be a little bit whiplash if you're constantly moving across the different files or folders or projects or conversations. Are there strategies or tactics that you use to stay focused? Time block? How do you like move across all these different businesses easily?

Elise · 32:05

Ooh, that's a great question. And it's funny because for me, specifically, it's hard for me to time block because my boss is also Jin X. And so he loves to pick up the phone and have someone pick up the phone right then. He's not like demanding in that way, but if he has that time, then I need to make myself available. So I think like A, having a project management system, for like the small task where I need my boss's input. Like, hey, can I reach out to this podcaster about this? Or can I reach out to this producer? Like, where are we with this pitch deck? What do you need from me? So that way, because it's also like organizing my boss's time, right? Of trying to decide like, okay. So that's been really helpful as I implemented Monday because I can break things down to the subtasks and like pink him there so that way he can just go through that list.

Maggie · 33:04

Yeah.

Elise · 33:04

So that's one thing. And the other thing too is because sometimes it could be a little bit more, a lot of things become urgent quickly, right?

Maggie · 33:14

Yeah.

Elise · 33:15

And each one of these areas. So I just strap out my boss. I'm like, here's what I think the priorities are. And it sometimes changes throughout the day, right? I'm like, okay, this is what I played on doing. Where are we with this? And should I spend my time here? Is this aligning with your priorities?

Maggie · 33:35

Yeah, it sounds like you, well, you're, you have a great boss. You guys have great communication. You love this person, which is great to hear. Like I always, I love to hear that for people who they work for. And it also sounds like, you know, he's able to direct you in your time and help you figure out, like, what's most important and you're there for them when they need to call you. All the things. And that's Chief of Staff work, right? Like, it's never clear what our priorities are. If you're in helping one business or three, like, there's going to be something that takes your mind and, you know, concentration other other places. So I think it's just a normal Chief of Staff struggle.

Elise · 34:12

It totally is. It totally is. And I also have that project management system there, too. So if he feels a little micromanaging that day, really wants to know what's happening. I like to put all my updates in there. So that way, it's self-service, right?

Maggie · 34:25

Yeah. Is there a software or tool that you guys use that you like?

Elise · 34:30

I just use Monday, because that's what I've used in the past. But I think it's just dependent on what your principal A is using right now or what they can adopt.

Maggie · 34:40

I was just going to say that. Easy and willing to adopt, especially when you're dealing with the principal and you just want to make it easy, it's a big one. OK, so last question for me. And then we've got a ton of questions in our Q&A box here. And I love this question. So you've been working with a high net worth individual for a while. Are there any takeaways you can share with us around kind of how they conduct business that can help average earners grow their wealth?

Elise · 35:09

This is such a good question. If I turn just to the side, it's because I like jotted some notes down.

Maggie · 35:16

Yeah, yeah, that's great. We appreciate it.

Elise · 35:21

So, something that's been really surprising to me is that most wealthy people that I've met in this role have zero online presence, which is fascinating. Zero, none, half of the businesses, you won't have heard of.

Maggie · 35:39

You can't even find the businesses, not just the person in the business. Wow.

Elise · 35:44

Not even in a shady way. It's just like some people are pretty old school, and especially those super high net worth folks. That's kind of on purpose sometimes too. But I feel like that's been really interesting, and also why it felt like a gamble when I first met my boss. I was like, does this line up? I think that's been really interesting because these people invest in or run businesses that people need, that they need, and it's difficult to either exit the service, whether it's, that's why people are into pool cleaning, HVAC, lawn care, residential and commercial lending, a lot of these things. That brings me to my next point is that from what I've seen, it was like the quickest way to wealth is real estate. And, you know, I'm not sure how true that is, but this is just kind of what I've seen from a bird's eye view.

Maggie · 36:53

Yeah. I mean, it's, it's helpful to hear your observations. So people take care, take over what it's worth. Right.

Elise · 37:00

Right. And people, people get really interesting with financing, not in a shady way, but it's like, oh, I'm going to buy this multi-family property and then live in it, and then I won't have a mortgage cost. You know, things like that are really interesting.

Maggie · 37:15

OK, so this is a funny question. Does the average person have no idea what a chief of staff at a family office is, who you talk to?

Elise · 37:23

Right.

Maggie · 37:24

Yeah. Right.

Elise · 37:24

I have family members, people who are my best friends my whole world. They know everything. They're like, so what do you do again?

Maggie · 37:32

I know. I think you mix chief of staff and then you add the very ambiguous like family office term. And it's just like, I don't get it. So you're not alone. One of our one of our attendees here is a chief of staff for a high net worth individual. And she was saying that this is a huge struggle that she has, that nobody knows what she does. It's very hard to explain. And that she she feels feels your pain on the difficulty in like the hiring and the search and figuring out who you're going to work for because there's just no information out there.

Elise · 38:04

Yes. Yes, it's so true. And it's not like you can ask around because you don't know who they know.

Maggie · 38:10

Yeah, absolutely. So is it kind of the who you know game? If you do want to get into the family office world, would it be like, hey, Elise, can you keep your ears open for somebody that's looking for a chief of staff, maybe one of your principal's peers? Like how do you think somebody could get into family office work?

Elise · 38:30

That's a great question. And honestly, you know, I think like for me, I feel like I have a pretty good network, but I did not get this role by networking.

Maggie · 38:39

Right.

Elise · 38:39

So if people want to look it up, like there's a lot of recruiting firms because they, these ultra wealthy people, they take advice from people that they trust, right? So someone's like, hey, I use this one recruiting firm and I love my chief of staff. They're going to use that recruiting firm. And so, yeah, I think like that's kind of nice about this role, right? Is it's pretty, in my mind, it's accessible.

Maggie · 39:04

Yeah. Yeah. Okay. That makes sense. I love that. All right. So I have another question up here I wanted to touch on first. What do you think your most valuable skill is as it contributes to the success of your chief of staff work and your principal's business overall?

Elise · 39:22

Oh, that's a great question. So I would say mine's like two-fold. One is, I call it untangling the cords, just like the process of things. If there's anything that's not automated, there's not a process, I will find a process. We did not have good financial modeling, though I'm going to become best friends with the accountant and the CFO, and we're going to figure out exactly what our cash flow is. We are going to have automations and QuickBooks through Zapier. We're going to get W9s in a different way. That's probably just automating things. Then the second is empathy. Empathy is my superpower because I'm sure you can relate to this. Half the time, you're just refereeing conflict between different people. You're like, we're all wanting the same thing here. Let's all get on the same page, and you're listening, and you're trying to understand what people's motivations are, and you're refereeing between co-founders or different executives. That's a responsibility I don't take lightly, and I used to think it's to get vulnerable, starting out in tech where it was only men, and being empathetic was seen as this thing to hide, or it was more of a, what's the word, liability than a skill. Now I'm like, oh wait, this is my superpower. What a cool gift.

Maggie · 40:59

Yeah, lean in.

Elise · 41:02

Right, exactly.

Maggie · 41:04

I love that. Okay, so this comes up a lot, and I would love to hear your answer. How do you and your principal measure your success as the Chief of Staff? Then do you.

Elise · 41:16

Yeah, that's always a question I ask him, because his personnel, like his goals are always changing, right? Like shocking, it's like new shiny things. I'm always trying to like kind of be like, hey, what about this? What about this?

Maggie · 41:33

Like I know, I know this is a good thing. This is a good thing. We want CEOs and principals in that vision space. So we kind of joke about it. But like our role as Chiefs of Staff is to support them staying in that shiny thing space because they are the idea people. So I'm just going to put that in there because we were kind of laughing about that.

Elise · 41:52

Yes, yes. And I was just talking about this with a friend yesterday. It's like every successful business has a vision or what about it's like, what if we could do this or this or this, which is great. And I have the have you thought about person.

Maggie · 42:08

And the capture, manage, prioritize, like placed for them to land.

Elise · 42:13

Yeah, exactly, exactly. And so it depends on the organization, right? To where like you can gather more KPIs, because like I love a KPI, I love an OKR. And that's something like almost in every role I've had to manage up and kind of like teach executives the importance of those and kind of keeping us all to this like North Star. Right. And so I mean, at the end of the day, though, for what we do, it's, I mean, profit margins and margins and money. Yeah, that's kind of like that at the end of the day.

Maggie · 42:45

And sometimes chiefs of staff are responsible for that and measured on it. And I think more often it's a lot of soft side feedback for chief of staff roles. Like I think when I, in my last corporate chief of staff role, when I knew I was doing a good job, it was when multiple executives on my principal's team came up to me and said, we've never been this organized. So I've never known what was going on. We've, you know, those kinds of things. And it just sort of like, oh, okay, I'm doing this right. You know, back when there's no resources for chiefs of staff and you don't know if you're doing your job, like there's a bit of that. It's just soft side feedback sometimes. If your role isn't directly relating to performance or scorecards, at least early on or yet.

Elise · 43:26

Exactly. And that's something where I had to relearn and retrain myself because I can be so KPI and OKR focused. And in reality, all that matters is his opinion of how I'm doing. Am I bringing value? And if I keep pushing him to quantify that, then he might get annoyed. So sometimes I need to stick to that soft side feedback, right? And so, yeah, I try to be a little bit more flexible now with that.

Maggie · 43:54

Yeah, that makes a ton of sense. So let's go back for a minute to your story around moving from CEO into your first Chief of Staff role. What, how did you know that was the right decision? What specifically made you realize that Chief of Staff might have been a better fit than CEO for you?

Elise · 44:17

That's a good question. I think just looking at the job description and what people did, there's a book that I really like called Pivot, which gives really, have you read Pivot before?

Maggie · 44:30

I think I have it. I think it's on my list in my Audible library.

Elise · 44:34

On the shelf, yeah. But in between every career break, I always read that because it helps you map out exactly what you want, what your dream day is like, and talking to people I knew on the role and looking at the different responsibilities. I was like, this is my favorite part of my day when I get to do this stuff. Cool. I am the what about person, have you thought about? I don't always like to be the visionary.

Maggie · 45:00

Yeah. You were able to realize that during that transition. It's good.

Elise · 45:05

That self-awareness is key. Also, I ask people around me too, of people that I worked with, of just like, where do you think my skills lie? Because I want to make sure that I have the right assessment of where my skills lie.

Maggie · 45:20

Yeah. Totally. We've got a question around how did Elise find her family office job. She mentioned that it was actually the first and only time that it was not through networking, that it was a job board. Then I think the second, the follow-up question to this from someone else is, you couldn't find a lot of information, there wasn't a big online presence. What made you say yes?

Elise · 45:46

Yeah. I think it was the vision and then the conversations I had with my boss too.

Maggie · 45:50

Just a good feeling?

Elise · 45:52

Yeah. I really try to ask, I always ask, what's your management style? How would people describe your management style? The first call with him before I met him in person, which was super helpful here too, is he was on his back patio with his dog. He was like, wait, do you want to see my dog? I was like shifting over.

Maggie · 46:15

A real human.

Elise · 46:17

Just a real human. Yeah. His kids would come say hi and you're like, oh, this is. He really had a clear vision too of what he was building. And so, yeah, there's only so much due diligence you could do.

Maggie · 46:32

But yeah, yeah. And I really do believe in like getting to a place where you really know yourself and you're able to trust your gut and you're able to ask the questions that you think you're going to get as much information as possible, but you might not get all of it. And then just kind of how does it feel? What does it look like if you were to say yes? What does it look like for fear to say no? How is my body feeling in those moments? Like it's it's a lot. And I think those are lessons that some of us probably learn, like down our career journey a bit. Like, I don't think I had that awareness 10 or 15 years ago. But trusting your gut, and I'm glad that it's been working out for you.

Elise · 47:09

Yeah, that's such a good point about trusting your gut and what you feel in your body, because that that has never failed me.

Maggie · 47:16

Good.

Elise · 47:17

Until now, right? Like, yeah.

Maggie · 47:20

Yeah, I love that. OK, so I want to go. A little bit deeper into kind of a couple more questions here. From a planning perspective, are there tools or systems that you guys use that you would recommend other people check out in the Family Office world or just as chiefs of staff? Any platforms, tools? It sounds like you work a lot. QuickBooks, Zapier, you know, all the things. Big automation fan.

Elise · 47:46

Yeah, so I think I would even like drill down and ask what kind of planning specifically.

Maggie · 47:54

Yeah, okay. Well, we'll see if somebody chats back in on that. But okay, well, we're just going to take a couple more minutes here. Elise, advice you have for aspiring chiefs of staff, for people that are looking to get into family office work, what should people be doing to build and grow their career in the chief of staff arena?

Elise · 48:14

Yeah, that's a really good question. So A, I would say like a lot of the MBA level type of stuff I see in a lot of these job descriptions, people are looking for the financial modeling aspect, the consulting aspect where you can really come in quickly, make assessments on where the business needs help and then be really quick to that. So I think a way to do that in current roles, now it's really worked for me in the past, is just ask to sit in on meetings. Yeah. Just to ask to sit in on meetings. That's such an easy ask, especially with someone you've already built just a little rapport with, and I just said like, hey, I just want to sit in this pitch meeting. I'm interested in it. And I like it because if the person is busy or important, it requires nothing on their end. They're just like, I'm going to invite them to the meeting.

Maggie · 49:08

Yeah.

Elise · 49:08

And once you've sat in two or three, you have the contacts. You have the contacts, they ask, what do you think? And you're like, maybe I could help with this one PowerPoint slide. And I think it's such a great way to augment any outside learning that you're doing in addition to Nova or any other courses that you're doing, any other upskilling because that way it's on your resume. And you have a really clear role that you've done. And so that opens up you up to opportunities inside your company. But even if you decide to interview outside, you're like, oh, this is already under my JD. And so it's just a part of your experience.

Maggie · 49:48

Yeah. And this is so relatable to, I think, anybody on this call. It's truly like, EAs, ask your principal to join in on something. Ask to join the meeting. Chiefs of staff, if you're not invited, it could have just been missed, right? Like just ask to go. Invite a peer who's learning. Bring somebody else in. Pay it forward. I think that's such a good advice from you, Elise. So thank you for sharing that with us.

Elise · 50:16

Yeah, yeah, of course.

Maggie · 50:18

Okay, well, we're going to wrap here. I did not mention in the beginning, but one of the cool things that Elise has done for us at Nova Chiefs of Staff is she created a investor market report assignment for our course. Basically, students can research what it's like to dive into real estate investing and the reports that you're supposed to provide for your principal and investors, and you dive into this deeper level of an investment analysis than most categories of jobs that have nothing to do with real estate. Students are really, really loving it. If anybody wants to check that out, just send us a note at hello at novachiefofstaff.com, and we can give you the information for how to access that. But it's been wonderful having you part of our Nova ecosystem, and it's been great to have you on today with our Nova Chat. And thank you so much for being here.

Elise · 51:15

Of course, of course. It's my pleasure, and thank you guys so much for joining.

Maggie · 51:19

Yeah, awesome. Well, thanks, everyone, for joining. We'll let you all go and have a great afternoon, evening, night. Have great dinners tomorrow, all of the things. And let us know if you need anything. You can find Elise Kennedy on LinkedIn. If you follow me, you can find her through me very easily. So we will see you all at our next session. Take care.

Elise · 51:43

Thanks everyone.

Maggie · 51:44

Thanks Elise.

Elise · 51:45

Bye.

Speaker 2 · 51:56

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