Building Your Board Portfolio

Brandon (00:29) Okay, this is gonna be a good one. I I'm super excited to welcome my friend, a a living legend. I mentioned before we before we got on the call that she is on the Mount Rushmore of of board directors. OG, you know, just things that were side projects for her have kind of changed the the complexion of Silicon Valley in many ways. And we're gonna dive into that story. Miss Stacy Brown-Philpot, thank you so much.

or taking your time and joining the Owner Mode Summit and sharing your journey with with a lot of other folks who are hungering to hear how can they get, you know, could just get an ounce of the impact that you've been able to make in your career on the field and off the field as a board director. Thank you, Brandon. It's so good to see you, friend. And I'm proud of everything that you are building, including Owner Mode. So well done. I appreciate it. And we're gonna talk about what you're building because, you know, most people have a good phase, you know.

A a lucky person is maybe two or three. You're on like, you know, phase four. And in a lot of ways, this is kind of the the biggest, the biggest bet, the biggest impact. You know, we're gonna, we're kind of we're gonna get into that. But we have to at first kind of start with your journey and and I'm a Chicago guy, you're a Midwest Roots person, and and you know, a lot of people will say the the the environmental change, the shift alone is is a lot.

Right, for a lot of people and and you not only made that shift from Detroit to Silicon Valley, but you were able to really emerge as one of the the leading voices in Silicon Valley. So we used to understand the ingredients, you know, that that were mixed in the pot to get you to the to the place where you were in the forefront of what became obvious to a lot of people but was less obvious at the time where you kinda got into tech. So tell us a little bit about, you know, your your your backstory. Yeah, I

Growing up in the Midwest is, you know, we were not a flyover state. I guess we are, right? Like everything was happening in the East Coast and then California. but what I where I grew up, and I'm sure you had this too, Brandon, in Chicago, is we were taught to believe in something and stand for something. And I grew up in a house with like four generations of women, all of whom were taught, you know, taught me, taught my brother.

You've got to stand for something. This is what we believe. And whatever you believe in, you hold true to your belief. And I'm a Christian by faith. And so I believe in God and my faith has guided me in a lot of ways. and it it's helped me stay grounded, particularly as you come to the world of Silicon Valley and recognize that so much is happening so fast, and what your role is and what it should be and could be is always changing.

but Grammy, you know, who passed away last year, just really taught me the importance of just keep living. Good things will happen, like the highs are gonna be high and the lows are gonna be low. And through it all, you just gotta keep on going. and I think a hallmark of an entrepreneur is that they gotta keep on going. And it's it's the DNA that I think that I was raised at with when I grew up in Detroit.

And and I I've been fortunate enough to meet your f your family and and they are very grounded people. And I I do think that grounding, I can see that through line across the generations. But you had the grounding, you also had incredible timing, right? You know, on the tech front. You happen to put yourself in position. I I arrived to Silicon Valley around 2013. It was it was late compared to you, but still relatively early in terms of like it being very obvious that the value creation and market cap.

was was going to be driven by the Silicon Valley companies. How did, you know, what was your journey into tech, into Silicon Valley? It was a decis my decision to go to Stanford for business school brought me into tech. When I grew up in Detroit, I went to high school at a high school where there was a woman who went to Stanford for college and I was in the same calculus class as this woman.

I was a junior, she was a senior, and everybody went around and said where they were going to college. And she says, Stanford. I was like, that's interesting. And I hadn't thought about Stanford. I was a business person. I wanted to study business. And so I did. I went to Penn. I went to Wharton. I got that degree. But after a couple of years of being in public accounting and going to work in investment banking at Goldman Sachs, I started to see where was wealth being created? How was it being created? And this was in 1999.

when there was the dot-com boom, which everyone was like out here capturing the value. And I was really trying to understand how does this how does these companies really create this much value? And I was an MA analyst. So I was doing the math and the numbers and the numbers weren't quite adding up like they do for a traditional acquisition. So I got really interested in understanding that. And that's what I focused on when I got to Stanford. What is this Silicon Valley place? How does this place really

Create so much value, how does entrepreneurship really work? And I spent two years thinking I was going to be a VC, president of the Venture Capital Club, got a summer internship in VC, that was the plan, and got some advice after my internship to get some operating experience because I'd be a better investor if I did. And having not

worked in a company, I'd worked in professional services and public accounting and banking. I said I'm gonna go get some operating experience. That's how I ended up at Google. I was gonna take a couple years, get some operating experience, and then go back and become an investor. But Google became this wild success story that you can't predict, you couldn't anticipate. And if I would have said back in 2002

you know, this was like the next biggest wave of technology. It felt like it, but it wasn't clear until you look back, say, yeah, wait, this wave of technology was so important. So I rode that wave at Google for almost 10 years and became, you know, a tech executive that took me on to to TaskRabbit and then ultimately back to Venture Capital at Cherryrock Capital. I learned something there. I I didn't realize your initial game plan was was VC, which I could argue

Being on that back then was still kind of forward thinking because even today, right, like the idea of launching your own VC firm is is perceived to be this really daunting task. You know, we're talking about 15, 20 years ago, you know, and so this pioneering kind of mentality is something that shows up a lot. And we're gonna dive into your your time at Google because there was some some other pioneering, you know, that that happened there. But

You know, when I kind of reflect on what I heard, really the ingredients for you was doing your own math, right? You weren't following the herd. You were you were keeping your your your ears open, meeting people, and then deciding for yourself what you thought was an interesting opportunity. It was an ongoing consulting. I went to Ward I want to go. You did banking, but you know, to a large degree, you were kind of moving on, you know, at at the speed of your own drone. And so, you know, I arrived to Google. What what employed do you remember? Did Google used have this thing? It was like,

go slash percent and you could see how many people join the company after do you you were early old I forgot I know it was like around a thousand people in the company when I joined. We were around around a thousand. It was like fifty thousand when I left. So was like around a thousand people somewhere. Which is insane. That is insane. And so when I landed in twenty thirteen at Google, I was already like wow. You know, I was coming from like New York finance. There were no perks. I just it was it was like

Disneyland, right, professionally. You know, it was sli literally it was a slides and colorful bites, pinwheel hats, and and it was it was crazy. But within that space, you created a space that I enjoyed, right? Which was when I came to Google, we had all the perks, but there was not a lot of people that looked like me. And the Black Googler Network was a subset within Google's kind of ecosystem that really

made me feel comfortable and at home coming from a different city, you know, just everything really changed for me. And BGN was was largely driven by your vision. Am I am I on target here? Yeah, it was I actually had the same feeling you had the years before you when I was there, I was like, wait a minute, I felt like a little bit of a fish out of water. There weren't that many black people in Silicon Valley, and therefore not that many at Google.

So I I got lonely. I said, well, what can I do to change that? And I started collecting us, you know, see somebody go into a meeting, like, hi, how are you? And eventually we became a group that became the Black Googler Network that really set out the mission of identifying and creating a space for black people to succeed at Google. And so we started with attracting and recruiting.

Because it just wasn't that many of us. And we created a plan around recruiting from different colleges and universities. We expanded it through Larry and Sergey's support to HBCUs. We really got David Drummond involved in making sure that those candidates got a fair shot at the roles and just changed the way you thought about what it meant to be a diverse person, you know, in the company. So by the time you showed up,

It was exactly what like when you said that, that made me feel so good, Brandon, because that was the goal in two thousand five when we created BGN, we wanted people to show up and feel like they could find community. And when you described your f experience, I was like, Yes, that it worked. No, it was it was it was a huge, huge factor in me feeling comfortable like in in in in this space. And and I I'll never forget, I remember David Drummond was the was the executive sponsor.

The Treyvon Martin situation happened and that TGI Friday, he had a hoodie on. He walked on stage. He had a trail of people behind him. And I was like, you know, this representation really was, again, like this idea being pioneering, not to mention how many other tech companies ended up emulating that model, creating a space for, you know, twenty, thirty other companies who saw that space was necessary. So I have to shout you out because, you know, I think.

This goes under the radar, but you know, to get people comfortable in the environments that are driving a lot of the wealth creation and opportunity for us to participate in in tech, right? That is a major, major, major you know, factor, you know, for for wealth creation. So I can tie that directly to wealth creation. So this is in addition to you navigating. And another thing I, you know, I'm aware of and I want to hear this story is that pioneering again, you

Did an assignment abroad at your time at Google. This was a time again where that seemed, at least to me, radical. And also the country you went to, India, right, was early, right? And now we're hearing, you know, a lot more. And you know, you were early on that. So tell us a little around how you navigated your time at Google. And I would imagine that experience abroad differentiated you in a great way. So when when the board conversation started materializing.

You could point to some experiences that really, you know, allows you to stand out even beyond being an early employee at Google. Yeah, it it it turned out to be much more important for the board than I thought it was going to be. I didn't go to India thinking I wanted to join a board. My time at Google was I started in the finance team. I was working with this team called online sales and operations and doing a lot of great finance work, which involved launching in new.

countries and building operations teams in new countries, large ones. Like we built a large one in Dublin and we built a large one in Hyderabad, India. And we had a leader in place. That leader left and they needed somebody to go on an interim basis to run the operation while we were finding the new person to be in the permanent role. And I've gone at that point from managing 200 to over a thousand people. So

From a leadership standpoint, it just changed the inflection point of the scale at which I would lead and could lead and the nature of how to lead at that scale. And so it taught me a lot about inspirational leadership. It also gave me a chance to really operate in another market and understand the cultural dynamic of what does it mean to be a black woman to show up in a different country and how do they receive you.

Also, what about this culture do I need to embrace so that I could be successful? And I remember there was a day when my apartment flooded. It was the monsoon season and it rains and the rain just it just happens. And I come in and I'm like panicking. It's like water everywhere. And I'm like lifting stuff up, picking up pillows and like things. And the people who were there to help take care of the apartment were like, Yeah.

It's just water. And I was like, whoa, it is just water. Right. And there was just this moment of like total crisis. And they were like ready to deal with it. there was a snake in the building. One time there was a snake in the building. And I'm like, my God, it's a snake in the building. Like, we're just gonna go get it. And so it taught me like not everything is as much of a crisis as it you portray it to be. And when you're somewhere, like it sometimes it's just water and you will get through it and it will be fine.

so it taught me a lot about leadership and having that leadership and at a global scale helped with the profile of what makes a good board candidate. How do you stand out and what boxes do you check for a board that's looking for somebody like you? And I can go into more details whenever. No, we will. We absolutely will. and I want to ask you really two questions. But the first one, it might take

30 minutes. if you can remember them all, can you just list the boards that you have been on? And then I wanna I wanna go back to your to your first opportunity. But this this list for us so we can appreciate how much you've been around the block. Okay. This is gonna be hard. I might I'm I feel like I'm gonna leave some out because I've been on some nonprofit boards. I've been on Black Girls Code, the Urban Institute. I was on the GSB.

Stanford GSB Alumni Association Board and Advisory Council. I am currently on the Stanford Board of Trustees. On the for profit side, I'm on the HP board. I'm on the StockX board. I used to be on the Noom board and the Nordstrom board. I also serve on the board of a company called Joy, which is an early stage startup that you use to do event planning.

and then I'm on the board of some of my portfolio companies, namely Coactive. and then finally I'm on the board of advisors for Aerial Alternatives, which is a private equity firm that is focused on advancing equity in diverse communities, with Les Brun and Melody Hobson. So that's the I think I got everything. I I don't know. Let me think of my timer here. Okay.

And again, I have to, you know, this is this is Mount Rushmore, right? You know, level. And so we have to reverse engineer. And this was kind of leads me to my question, which is you mentioned it seemed like your approach was like, I just want to create value and I'm going to go, you know, if I want a team and we're opening up new, you know, let me learn, right? You're kind of optimizing for learning. Was there a a an intention at at the earlier stages of like a true north of let me put a portfolio of skills and experience together?

Was it what what was kind of your your compass that you were using to to make certain moves? Yeah, I I there is a portfolio of at one point I was gonna be a CFO, right? So I was building that portfolio and then I said, Maybe not CFO. I think I wanna be a COO. And so then the question became what is how does who who is a CFO? What skills do I need? And that's really what took me out of finance and into

Sales and operations and ultimately into India or to India. And then you look up after the C level and you're like, well, what's next? It's the CEO and it's the board. And I said, wait a minute. I hadn't thought about that before. I should aspire to the next level, which is getting on the board of a company. What does that take? And then and then I did start intentionally talking to people about.

What does it mean to be on the board of a company? a nonprofit, a for profit company? What skills do board members look for? And how do I position myself with the skills that I have? So a lot of the portfolio of skills for boards isn't so much about strategically targeting the board. It's more about understanding what your skills are and how does that fit with what

A particular board might be looking for. So at the time, my skills were early technology, digital, native, C level executive, because at that point I'd moved on to be the COO of TaskRabbit, who had operated at scale with global experience. Right. And I bring those phrases up because every public company board has a matrix and they have.

the nominations and governance committee, I serve on that committee for HP, you can look at our annual report and see the matrix and you can see the little dots for each board member who fills what bucket. And those tend to be the boxes that they want to check when they're trying to round out the board or replace someone who's rolling off of the board. Those are some of the skills that they're looking for.

And you just dropped a really, really big insight there, which is again kind of this idea of reverse engineering. If you look at boards, they have specific profiles that they are filling. You need to connect that to what your current expertise is and also identify what other, you know, elements you can bolster that with to tell a story that's going to align with where they're going to fill a need at a certain point. So let's let's talk about this first. If you remember, this is a long time ago, you've been on lot of boards.

This first time where this opportunity actually, you know, came into your orbit. What was the opportunity? How did it arrive? You know, walk us kind of through that journey. I want to talk about the HP opportunity. It wasn't my first board, but it's the first for-profit board. And I would say that being on a nonprofit board, the Stanford GSB Alumni Association, I was chair of that board and I had leadership roles.

So I could talk about having had leadership roles on a board when I was being considered for a for-profit board. When HP came up, I had already put out the feelers. I told people I wanted to join a public company board. I created a board bio, which Egon Zehnder used to have something on their website that would walk you through how to turn your resume.

into a board bio and the difference between the two. I'd sent notes to people who I knew very closely, but I wanted to specifically say if you get an opportunity to join a board that you're not excited about, please think of me. Attached is my is my bio. And I told everybody that I knew. And there was CEOs who were on public company boards already,

And recruiter. So it it was the full gamut. And I bring up that full gamut because you have to kind of spray the message out because you never know how it's going to come back and who's going to think of you for a particular opportunity. I I did something that was very strategic, which was to aim for a big public company board, because once you do that, then you can be considered for smaller companies.

I also recognized that as the COO of a early stage company, I could only do one. And so if I was going to do one, I really wanted to focus on one that was going to be very different than what I was doing already. So these are like the seed planting pieces that I wanted to make sure I talked about. Cause it doesn't just happen. And I'm going to tell you what happened, but it doesn't just happen, right? There's like a lot that goes on in the background.

But what happened with HP was someone that I knew got contacted about the HP board, shared my name with Meg Whitman, who was chair at the time of the company and CEO, and HP was splitting into two. So they needed to hire a number of new board members, I think twelve, in total, which created a lot of slots.

Typically a company will look for one person, maybe two, if you're going public, but really it's rare to have that many spots open up. And so my name was added to the slate. They were contacted by a recruiter. That recruiter knew me, had been reaching out about working with our firm to on executive hire. So we talked in that context. And I had met Meg Whitman at another event.

randomly, like not even thinking about the board. But because those interactions had happened, I became one of the candidates that was sort of on a shortlist for this board. And then I had to go through the process of interviewing. And I that's the important part. The interview process sort of took care of itself and we can talk about what is it like to interview for a board, but all of the steps of networking, knowing who the recruiters are,

The particular recruiter for HP is a woman named Bonnie Gwynn, who at the time was very focused on bringing more women onto boards. And now we know we should have women on boards, but at that, this was in 2015. At that time, we were not doing well in that department. And there were a few recruiters out there, her being one of them that was leading an effort to be intentional about the slate.

So that if you're intentional about the slate, you have a higher chance of selecting a woman for the board. And so it was a very diverse slate of which I was one of the the people to be considered for that board. So all of those things matter in the selection process and how you show up as a candidate for for for a board. And, you know, it's the epitome of, you know, luck is preparation meets opportunity, right? Because Yes.

Knowing Stacy, and if you've ever heard, you know, her talk, and we'll we'll get to this in a second as well, the authenticity and kind of like the vibe is is very calming, I guess you could say. But you just walked us through the greedy work of how you said, look, this is a goal of mine. I'm gonna get busy. And you and you got busy, right? You kind of laid out basically for people, this is how it really works at the end of the day, right? You gotta let people know.

You gotta come prepared, send them a note, send them the resume with the note, let everybody know. And then also be in a position where when they come to you, you already know where you slide in, how it, you know, potentially can can complement what they already have. You had done that work. And so then when the event of twelve, you know, seats open up for this extremely prestigious company, you had enough points that worked in your favor to get you on a short list, and then you kind of close the deal. And we do want to get to into the interview process, but

Let's talk a little bit around HP, right? This is, you know, no matter how much preparation you do, when when the brand HP lands as a as a possibility, you gotta take your glasses off and say, wow, I can't believe I'm at the table for an opportunity like this. So now you're in the, you're in the process, you're on the short list. What was your this is like Jordan Game Seven. What was your, your, your, your preparation process? What was your mentality? How did you make sure I'm going to seal this deal?

Yeah, I I was so excited. HP is an iconic brand. It, you know, just most people when they hear of it, they have some good feeling. Something happened to them or they were around something around it. So I was like, wow, this would be amazing. I reached out to a mentor, Ken Coleman, who had been on boards, who I'm gonna see very soon and excited to talk to him again.

and said, Look, I'm interviewing for this board. You know, what advice do you have? And one strong piece of advice that he that I he gave me that I carried into the interview process and even joining the board was like, stay in your lane. And I said, What does that mean? He's like, they want you for a specific reason. Understand what that is, and show your strength in that area. So

For me, it was everything was becoming more mobile. The company was going through a digital transformation. I was in a generation that could understand the next generation, millennials. I was at a consumer company. So I understood how the next generation of consumers were thinking. And HP sells printers and laptops. Right. So, you know.

They sell through partnerships, but in the end, this thing is something that's sitting in your house or at your company and the the end user is a is a consumer. And so I really focused on that in the in the interview process. And so I came with my questions too. I came with, you know, real questions on what the strategy was. How did how would I fit into the strategy and ask strategic questions throughout the process? There was this one moment.

That I'll share because it was this moment of like, am I gonna get this board? Zuri, my youngest daughter, was a baby at the time. And I was set to have an interview with someone on the board as part of the process by phone. And Zuri was crying in the next room. And I thought that I had timed it so that it would be between feedings and she would be.

napping and she wasn't. She did not go back to sleep. so I get on the interview and the woman who's interviewing me, I said, you know, we start and I think I'm gonna push through and do it anyway. Because I'm thinking like none of these people have kids, have babies. They have like maybe they have grandkids, but their kids are grown. I'm like really young compared to other candidates. And at some point I said, look,

Mm my baby's crying. I don't think I can finish this interview. I'm so sorry. And she laughed and she's like, that's okay. I have grandkids. She's like, we'll just do it tomorrow. And I hung up thinking, I am not going to get this port seat. It's not going happen. Because they can't like they want me serious people who can't, you know, who don't have time to deal with like their babies at home. And so the next day I do the interview and then I get.

when I do finally get the offer to join the board, she really appreciated that decision because she's like, look, family matters and and you're the exact person we want on this board because you're in the life of the person that we want to use HP products in the future. So I never even knew how that problem actually was part of the decision to to actually to get the seat on the board.

That might be way too much detail. No, no, no, no. I really want to tease out like some of the nuances. Perfect because it gets to kind of the next question, which is like, and I mentioned this before, the authenticity. So she she was saying, Not only do I understand that you fit into this persona that's important for us to understand, but you had a decision to make. A lot of people would have said, I'm gonna let this baby cry and I'm gonna try to close the door so they can't hear it. I'll deal with the baby later.

You said, excuse me, I my baby's crying. I I just can't do the call right now. And sh that was a values decision at the end of the day, where you said, you know what, like, I'm a mom, right? I'm a mom and that's something that is always gonna come first. And she understood that. She understood the humanity in that, right? And so it gets to this idea of how you show up in certain rooms. And and Stacy, we know you've been in some rooms. you you are always yourself. And I think a lot of people oftentimes

feel the need to not really be themselves because they don't think they're gonna be accepted. They think that they're gonna be penalized. And that's just an example of how you've shown up in rooms. And so I know this is a thing where now you're on the board, you're with all these gray hair folks who who this is their 20th board. and and now you're dealing with or you know, how did you deal with the imposter syndrome of do I belong here? How can I contribute? You had done your homework, but it's different

in theory than it is in practice when you're up against people who are, you know, at least the appearances, potentially intimidating. So tell talk to us about authenticity, showing up in rooms, dealing with being the only, being the first, being the youngest, be being the you fill in a blank, but but not feeling as though you you represent the majority. I'm gonna answer that question and and bring back the values point because you reminded me of something.

When you interview for a board, you should ask what are the like read the values of the company that's public. Don't ask what the values are because you should find that. Don't go in with stuff you can find online. But talk about the values and ask how the board exhibits those values. What are the values of the board? Because it is very true that that value, that trait, was actually really important to this board.

And that was one of the reasons for selection. A great question to ask when you're interviewing for a board is about the values of the company, how the CEO lives the values, how your values match, because then that that's really going to demonstrate what it means to be a true board member and exhibit the levels of governance that's required for a board member. And

So I'll I'll pivot that into the answer of your question, which is like, how did you show up in the room? And you you do bring those values. And part of it was trying to figure out, okay, what's the culture of this board? And everyone says, okay, in your first meeting, you should sit back and listen and watch and learn the culture of the board. And me being younger, I was really like doing that. And at the end of the meeting,

Meg was like, okay, we're gonna go around and everyone's gonna talk about like one thing that they thought was great and one thing that, you know, they want to learn next time. And I was like, wait, I didn't wasn't expecting to talk at all. But because that set the tone and the culture of the board. And and so I had my feedback and I had taken notes and I was ready to contribute. And I stayed in my lane of here's an area that I saw.

you know, in in the mobile strategy and here's something that I think we could do next time. And that really shifted one, my confidence, which was wait, I said something that no one else said in the room. And people had questions. And I I didn't notice that. And I'm thinking to your point, that this is their twentieth board. They've been CEOs of whatever for a number of years and they know everything. But they didn't know that. And and so it really helped shift

The dynamic of I feel like an imposter, but no, no, actually I belong here and there's a reason that I'm here. I'm bringing up issues and topics that are relevant for this company that no one else, all these high powered, much older people had thought of. Got it. I love that. So let's let's talk about haters. So you now are on the HP board.

You know, your coworker from five years ago opens up, you know, the news. Stacy is on the board of HP. And, you know, some people are are are celebratory. Other people say, I'm hated, basically, right? how do you deal with kind of breaking these barriers, getting into these spaces, and then now the perception you have to deal with by doing

by being excellent, people taking shots, chipping away, you know, taking away from the merits of what you've done and how much of an accomplishment to be applauded that is. How do you deal with that? Because that's something that anybody who's ambitious, if they actually achieve their goals, are going to have to deal with.

I my grandmother always taught me that there's always gonna be somebody who doesn't like you, as a young kid, just growing up in Detroit, and that was always true. And so you but you have to move forward. I I don't even pay attention to the noise. I don't read my own press on the positive side or the negative side. I just focus on what I'm doing, what I'm trying to accomplish.

And if some people can see that and see the truth in what I'm trying to bring and the value that I'm trying to create, that's all that I can think about. The other thing that I've learned, you live long enough and you realize that a lot of people's reasons for hatred and jealousy is because of something they haven't achieved in their own life that has nothing to do with you.

And I can't spend my energy worrying about someone else's issue. I pray that they decide to work on it themselves and work on their issues, but I have to I have to keep moving forward. I'm also from Detroit. So very few people come to me in that way, Brandon. You know. I hear you.

Let's talk about balance because now you mentioned before, at the time when you joined HP role, I mean board role, you I believe were COO for Towers Right, but you became CEO. You have a major on the court, and then you have now HP off the court, and you have an older baby, but also a new baby that you're you're you're trying to figure these things out. Balance. How did you navigate doing these things and and ideally doing these things well?

It was not easy. And I I later joined the Nordstrom board and I c and and having done that and had two public company boards plus a CO role that turned into a CEO role and then parenting two children's and a husband, right? Like it was a lot and I can understand why the recommendation is to serve on

One board if you're in a CEO role, because your major is your company and it has to be. And that works fine if you're on a board where there's nothing going on. But when something happens, then you have to dive in and you have to spend time and the board has to meet. HP had an activist stuff. We had to stop what we were doing. We had to bring in a new CEO. We had to stop what we were doing. And so

You sort of go in cycles. The board meets every three months. So there's a cycle of preparation for that meeting. There's a I used to get Google News feeds just to stay abreast of what was going on in the company and use my weekends to read that. So you come up with little tactics to stay on top of the board while you're running the company. And you also and I also did

what I think a lot of CEOs should do, no matter whether you're on a board or not, which is to have a great team in place so that if I need to take some time away because there's a crisis with one of my boards, I can do that because I've got a great leadership team in place that can step up. Got you. And so board portfolio is a name of this particular talk. You mentioned casually, Nordstrom too, right? Which obviously is an iconic brand that many of us

you know, working as a kid, saving up our allowance to buy something in Nordstrom, and now you're sitting on the board of a s you know, of a store that kind of represented the epitome of luxury. you know, at a time where I would argue with like it's heyday, right? and so when you thought about board portfolio, and I've had this conversation with with a few folks where they would say, kind of what you said, I'm gonna wait until the right opportunity comes along. Other people were like,

Look, if I can get on my first board, I'm gonna I'm gonna take whatever's coming my way. And then then I can talk about, you know, I'm in there. Now I can talk about a board for board portfolio conversation. What is your take on it? And obviously the HP thing, you had kind of mentioned before that you wanted to make sure you were on a public board, like you were intentional about it. But how did you think about portfolio construction? How would you advise someone who is who is do I take the first opportunity or do I, you know, or do I really hold out, you know, for something that

Worst case scenario never comes. What I I've been on the HD board for ten years. I served on the Nordstrom board up to the time when they were going through the process of being of going private. So that was seven years. I always tell people, do not join a board that you don't want to be on for ten years. Because it's a long it's it's hard to get off of them.

And so taking the first thing that comes along is not a good idea if you if it's something that you kind of don't really want to do. Cause for me, it was like I just said, it was my weekends. It was my Saturdays and my Sundays, catching up, getting prepared, which took away time from my kids. And it needs to be an industry, a sector that you're excited about because you're going to be reading and spending time. And it needs to be with people who

That you want to spend time with because you're going to spend a lot of time with those people. So I do not advise taking the first thing that comes along. I advise really scripting out what your criteria is. Do you want to be on a board that's in the US only or outside the US? Are you willing to travel for this board? What sectors matter to you that you're interested in learning more about? What stage of company is interested? Like all of these things.

Write that down so when something comes up, see how many boxes it will check for you. After you get on the first board, you're right, there is a little bit of construction to this sense that you can actually construct a board portfolio. When you're running a company, it's pretty hard because you're running the company, you can't really get on any more boards. But I thought about my next boards. I'll tell you how I thought about them and what the construction was like.

For Nordstrom, like you, I grew up, I grew up dreaming of being able to shop there and, you know, getting the chance every Easter to get one thing from Nordstrom. So when someone who was on the board approached me about the opportunity, I I said yes, because it was this great opportunity to be on a board of a company that I admired from afar for so long, even as a little kid. And it was on the West Coast.

So I didn't have to travel very far as a parent. HP is in the Bay Area, which is where I live. And it was consumer focused, which is what I was doing at TaskRabbit. And their focus was on how do we become a more digital business? We have these great stores, but lots of people are shopping online and apps where, you know, proliferation was happening. We've got an app, but we really want to create a great digital experience.

For the Nordstrom customer and bring them into this new generation, which was something that I was doing already in my in my day job. So there was a lot of alignment there. And that's how I thought about that construction of really playing towards the skills that I had and the ones that I wanted to continue to build. With StockX and Noom, I was interested in those spaces. I was interested in health and wellness.

I was interested in this concept of a marketplace for culture and curated items, having had a marketplace background. And so when those came up, yes, there were people who reached out to me, but why would I say yes? It really fit the portfolio of knowing about new sectors and new spaces I wanted to learn about, and then pursuing those opportunities.

And as a recovering sneaker addict, you know, have I've I've stock X has done some damage on my on my personal credit card. So I I get the idea of you're spending time, you're committing your life force into these things. They really have to resonate because, you know, excitement needs to be a part of what's going on. Okay, let's this is kind of like a a bundle of questions that you can unpack however you want. there is a difference between running a pu you know, being

on the board of a public company versus a private company. I would love for people to understand the nuance and trade-offs and to the degree, right, that a lot of people, again, because we're hearing a lot about your motivations, which is growth, learning, associating yourself with things that you believe in, right? But a lot of people say, you know, the income of a board, the, or the income diversification that comes with a board is a big plus. I don't, I don't have to have one check that I'm dependent on.

I had now have a broader portfolio of things that give me ownership, which is the theme of the Owner Mode Summit. We are no longer in a place where the W-2 employee is as secure, AI is disrupting, and people are trying to figure out how do I not put all of my eggs in one basket. So help us understand the nuance between public and board and to the extent the financial considerations and how meaningful that is overall. Yeah. It's it's certainly meaningful. You get

A small amount of compensation, cash compensation on a public company board, all this stuff is public and it tends to be around the same amount because no board wants to look like they're overpaying compared to other public companies. And then you get some equity, you know, some grants, some stock grants in the in the company. Typically with a private company, there's no cash compensation. It was very, very little. and then there's a lot more equity because ideally the company.

has an exit and you know your you along with the management team is aligned with you know creating a good outcome and being a great board member that can help from a governance perspective shepherd that company into a good outcome. So is does board income create diversification? Absolutely. is it passive income? No, not exactly. Because you have to show up at the meetings

The meetings are when they are. So you have to plan your vacations around the meetings. Right? No one's gonna you want to go on vacation this summer and everyone's like, we have a board meeting in July. Well, you gotta come back. You can't go. So it's not totally passive, but it is in the sense that you're not showing about a nine to five every day. You could build a portfolio of three or four companies that could create, you know, an annual income for you that supports your lifestyle, that doesn't require you to be.

at one company every day, you just have to kind of rotate around to these board meetings over a period of time. So you can have a flexible lifestyle. And to the extent that the company performs well, particularly for the private companies, there's an opportunity for wealth creation. And so again, taking the first board that comes along, I wouldn't do that either. I would evaluate does this company have the potential to generate, you know, financial

outcome for me because if I'm not going to take cash as a private company, then of course this sort of financial opportunity becomes a factor in whether you take this board or not. Because you're still going to have to put the time in no matter what. It's a good company or a bad company, you're still going to meet every three months. It's still going to be two days. And if you fly somewhere, you still got to go. You know, so really doing the diligence around that potential. And if it's important to you that there's a wealth building opportunity there.

then evaluating that in your decision making process is quite important. I think something kind of being implied in what you're saying is this idea of really belief, right? The same thing that allows you to be authentic in these rooms. If someone approaches you with a bored opportunity, it's because you have something of value. And so belief that something else will come along that resonates with you is something you're saying is actually the smarter bet versus let me just lock in whatever comes my way. Kind of like dating, right?

Give whoever wants me. I'm not gonna be selective. I'm gonna just get in bed and and hopefully you know, hope for the best. You're saying, look, you know, take the long view on this thing. All right. So in the board portfolio conversation, we got to talk about committees a little bit, right? You know, once you kind of get into the board game, there is a there is an art and a science of the committee thing. what is Stacy's orientation on on committees? Yeah, I am a CPA by training. People find that out and they automatically want me to be.

on the audit committee, which I have done. And what I think I would say originally it was reluctantly, because you hear the audit committee is like the hardest committee, is so much work and they meet more often, and it's true, and the meetings are longer, and that's true, but you will learn so much from being on the audit committee and for a public company.

Because everything financial runs through that committee. Typically all legal matters and things like that run through that committee. And so really getting into how the company works is an an important skill to develop as a board member. And being on the audit committee will teach you that. So I'm a fan of if you have interest in skills around, join the audit committee.

The other standard committees that boards have is nominations and governance and HRC, so human resources and and compensation, compensation committee. compensation is a great committee to be on. It's basically the CEO package that you really deal with every year. And then anything around executive compensation for key officers, board officers in the company. that committee also tends to

Deal with other HR issues that might come up. And then nominations and governance committee is about, excuse me, the process of bringing new board members in. So a lot of times being on the comp committee, you can you actually learn as a CEO, if you're one, like how this works at another company, great skills for that. For nominations and governance, it's it's selecting new board members. So if you want to be part of the process of bringing in new board members,

This is the committee to be on. So a lot of times when you're really advocating for diversity on a board, getting on that committee, you can be in the seat that is determining where in the matrix, right? Do we need to fill buses? Who is the firm that we're working with on this search? What does the initial slate look like? What are our requests for what the initial slate looks like? All of those things go into the process when you're serving on that, on that committee. So that's also a good committee.

To serve on. Excellent. Masterclass. let's talk relationships. Stacy, and and I I've been able to to be privileged to kind of be in in in spaces with you. And your relationships go deep, they go wide, but they all feel really organic. And I remember one time you had something at your place and it was like in your backyard, and and I'm going through you you're obviously an OG, so they get value. I'm like, that's whoever. that's whoever. Right. And these are people that are just sitting down eating chicken, you know.

You know, in your backyard. And so what is Stacy's philosophy on relationships? And obviously a lot of opportunities are driven by relationships, but the goal is not to be transactional. What is your philosophy around relationships and how do you execute that philosophy? Yeah, I I don't know if I have a f a philosophy per se on relationships, but I I do believe that relationships matter. And a lot of times

When I was growing up, I was so focused on getting a good grade. And we were taught if you get good grades, good things will happen. And they do, right? You get picked for opportunities, you get scholarships, you may get into a program and you may get into a certain school. It they do matter. But over time, what I learned is that beyond just the grades and the transaction is how you connect with people that

matters more. And the reason why it matters more is because you want people to remember you for something. And people will always remember how you make them feel. So creating a relationship is what I try to do is a connection of, I want this person to remember how I made them feel. Did I help them? Did I support them? Was I listening? Did I pay attention? I try to bring that into every connection that I have.

And unfortunately I can't invite everybody to my backyard or my Sunday dinners. I can't have a Zoom with everybody that I meet. So I try to do as many as I can with as much presence as I can for the ones that I for the for the ones that I can. And then it shows up with you guys moved across the country and we still have a good relationship, which is amazing. It is. so you you were an operator at the highest level.

You've been and can and continue to be a board director at the highest level. Most people will write out into the sunset. You are going to be an investor at the highest level. Your, you know, foray, as now, you know, general partner and founder of Cherryrock, Cherryrock VC, would love to hear your vision. and we are in very interesting times right now. I don't have to say it to you. You're in the middle of it all.

There are mega funds, you know, $15 billion fundraises. There, there is AI disruption. There are AI tools that allow people to build. How have you shaped your thesis at Cherryrock? What was it about this, this calling that brought you into this space? And how, what true north are you using to navigate how you're going to deploy capital? I'm so excited to build Cherryrock.

And because you've heard the story of how I started when I came out here 25 years ago to be in VC, I had I have to complete the the chapter. so there's no sunset. There's no, I mean I do love sunsets, but there's no writing off just yet. Cherryrock Capital is about creating opportunities for underinvested entrepreneurs who are building software companies in the US. And the idea came because

After TaskRabbit, I got involved working with other investors and identified this gap in the market, which is access to capital at the series A, series B stage for entrepreneurs who really want to scale their business and work alongside investors who bring deep operating experience. So I spent 20 years of my career as an operator, and now I'm putting all of that back into the next generation of entrepreneurs.

With the aim to change the face of wealth creation. Gravy is about ownership and wealth creation. How do we find and identify more diverse entrepreneurs who are building real real businesses and help them scale and grow? And so our approach is to lead investment rounds. We write checks seven to ten million dollars. We join the boards of the companies that we back and we really bring our operating expertise to help them. I have seen the playbook.

from my time at TaskRabbit. I've seen scale at Google. I serve on a number of boards and I've built a team that complements me with their own operating and investing experience to do it. And so if we are successful, then we will have many other cherry rock capitals. We ra we're on fund one. We're deploying capital. We raise $172 million and we hope to invest in 12 to 15 companies and we've got

four investments now that we've already made. I l I first of all I love the positioning because coming in and you know at the series A level, you're basically saying, look, we're seeing data, right? We know that there's something there to latch on to, but you're still underinvested, right? We're gonna help you grow to the next level. And I I know we can get into it, but I know how you built your team to build a very specific set of competencies that are really needed at that at that phase. But I think at the core, you know, I know we gotta

Be respectful of your time. The core thesis I would love to get your perspective on for our audience is there's a lot of fear right now, and and folks feel really unsettled. You know, there's geopolitical, you know, unrest in the US. There's a lot of craziness going on. and what used to be secure, right? Google at a time, it was like the ultimate secure place to be, right? And and like,

that's not the case anymore. And so on one hand, there's a lot of fear because folks will either have to disrupt themselves or deal with a much higher probability of being disrupted. On the other hand, building things has never been easier. Right. And so what is your advice to folks around this idea of moving from earner to owner and trying to address the calculated risk elements of this when a time where it's no longer really a choice, you have to really think about this now.

Yeah. I I you laid out the the backdrop very well. I I don't see I don't see the world becoming less complex. it's gonna become more complex and the geopolitical elements will become more complex, the opportunities in technology where I spend all my time will be more complex and as a result

Figuring out where you fit is the most important thing you can do. I am teaching my kids to learn how to learn. At every stage of our lives, we should always be learning how to learn. And never think that you're you know everything, you figure out everything, that there isn't more out there to learn. And be willing to adapt and change. So in that

And so that comes a little bit to your question of okay, what does it mean to go from earner to to to owner? Is there's an adaptation mindset here that is so important right now. How do I adapt? Well, wait, I need to have a portfolio of income streams. I don't just have one. Okay, what does that look like for me? There's my core job, and then there's these other things I'm planting seeds for. There's the learning. Well, how do I how do I go 1% every day? Every day.

What's one thing that I can learn? Increase my knowledge about something by one something new by one percent every day. How do I build that mindset for myself? I think that that's the right way to think about the world that we're in because it's hard for me to say in five years this is the kind of job you should plan for, or you know what, just get on three boards and you'll be okay. Like that there's no there's no way to say that there's one right answer for any person.

What I do know for sure is our ability to adapt and change is always gonna be constant in this much more complex world that you just outlined. The ultimate skill. And and I can make the argument, Stacy, as far as evolving and and and moving and challenging yourself to grow, you're kind of the the poster child of that, right? from Detroit to Silicon Valley to, you know, to being an incredible operator and board director to now changing the face of ownership through funding.

incredible founder. So with that, we're gonna go ahead and close it out. Stacy, give Stacy a round of virtual applause for giving us, you know, really a master class on her journey, board directorship, and a view on the future and how we need to move. So with that, Stacy, thank you so much for joining the Owner Mode Summit. We'll talk soon. Thank you for having me. All right, take care. Bye.