Stacy Brown-Philpot on Reclaiming Abandonment

What? You want to really work on yourself that deeply to process emotions like fear and anger, and on the other side of it is love and joy? How does that happen? The answer is it's a journey, and my journey is very different than what someone else's journey might be. But the important thing is to be willing to take a step, one step.

Welcome to The Art of Accomplishment. Where we explore how deepening connection with ourselves and others leads to creating the life we want with enjoyment and ease. All right, everybody, I'm really excited today. We have a three-way conversation today. This is Joe and myself, and joining us is Stacy Brown-Philpott. She is the former CEO of TaskRabbit and a founding member of the SoftBank Opportunity Fund. How are you doing today, Stacey?

I'm good. How are you?

Yeah, I'm doing well, and I'm excited to try this, uh, this three-way conversational format.

Me too.

Me too.

Yeah. All right, so tell us a little bit about yourself and what brought you to this work.

I, um, came to this work really initially not open-minded, but eventually open-minded, I would say. Um, I grew up in Detroit, Michigan, and grew up in a house of independent women who taught me the importance of independence. My parents got divorced when I was very young, and there were 4 generations of women in the house that basically taught me how to depend only on myself in order to make things happen. And that has served me so well in my career. What brought me to this work is that I learned that while the things that served me well in learning how to be independent also didn't serve me well in other areas, which was learning how to depend on other people. And when I realized I didn't spend a lot of time waiting for other people to do things for me, I learned through this work to get to the core of what that looked like, and it really centered around abandonment and fearing being abandoned because of things that happened in my childhood. So here I am.

Tell me a little bit more about, about that abandonment, about how you came to recognize that this was something for you to, for you to feel into. And what's one pivotal moment of transformation where you started to work through this experience in a different way?

The abandonment, it wasn't like all of a sudden I realized, oh my goodness, I've been abandoned. I think what I realized is that I compartmentalized a lot as a leader and as a person. And the compartmentalization was a coping mechanism for me to handle my emotions. And what I realized was that I was trying to not show certain emotions because when I did, I was abandoned by those emotions, by those people. And over time and through work, through this work, I realized that the compartmentalization had served me well in terms of being a really good CEO who could operate well and could get things done, who could hire good people and who could really just muscle through success. But I hid a lot of how I truly felt about people and how I wanted people to see me and especially depend on them. And so a pivotal moment for me in thinking about what that abandonment meant was just realizing that my parents got divorced when I was a kid. And so I didn't grow up having my dad around all the time. And because of that, because he just wasn't around, I never knew how much he mattered to me or I mattered to him. And while he did lots of good things like bring us Christmas gifts and bring us toys and sometimes come see us on the weekends, I never felt really the love on an ongoing basis that other friends that I had growing up experienced. And just knowing that he mattered to me really would have been everything for me. And so this year, fast forward 40-something years later, I had a conversation with my dad. And I went to Detroit this past July 2021 and said I wanted to talk to him about my childhood and really open up. And I told him that because of how we grew up, I never thought that I mattered because he was not around. And it was a moment where we were going to take a drive, Brett, and go and have this conversation. And we actually never left the parking lot because he just opened up and both of us were in tears just sharing. And he said to me, you've always mattered to me. And I don't think I knew what I expected from that conversation. All I wanted him to know was that how he made me feel. But when he said, you've always mattered to me, and in fact, there are some things that you did when you were a kid that helped me change my life for the better that I never knew about, that helped me see not only can I just make this statement to the person who I felt abandoned me and just feel the release, but also get information about what his experience was that just totally flipped everything I thought about what was happening to me as a child. And so that pivotal moment for me was just a release of like, freedom and knowledge that the one person I thought didn't care about me as much actually really did. And it changed my perspective on how I saw basically everybody else. Everybody else.

How did that impact your life as a leader? And looking back on your time as a CEO in the way that you had just described, being the CEO who's just getting it done, super independent, doesn't need anybody, how was that negatively impacting your, your business and your relationship with your team? And how much did you notice it at that time? And how much do you, do you notice it now?

I don't think I noticed it that much at the time because it worked. And when I was leading the company and now helping to run a venture fund and serve on a number of boards, people valued my efficiency, ability to get things done. And I'm pretty good at talking to people and being empathetic and understanding their perspective. But what I wasn't good at was really being truly vulnerable and showing all of who I am. And so what happened is, is there were only glimpses and moments. Where I would do that. For example, when George Floyd was murdered, the only thing I can do or could do at that time was show up as a Black woman who was in pain. Didn't matter what title I had. Didn't matter. Nothing mattered in that moment. So I could tap into that place. But I wasn't able to tap into it often and frequently. And when I did, It was often a very scary thing for me to do and not a very easy thing for me to do.

And what happened as you started doing that more scary thing, stepping into, stepping into who you are with acceptance of that feeling of abandonment?

I felt so much love, and that was joyful. Because to really feel seen was just amazing. And so to be able to stand up in front of people and talk about who I really was and to feel the shared empathy, the shared understanding, the shared pain felt so good. As a CEO, sometimes you— everybody wants you to take care of them. And they come to you with, like, the hardest problems, the most complicated problems, the ones that have the least amount of information to solve. And we take on that responsibility. And we forget that somebody needs to take care of us too. And so who's going to do that? Who's going to take care of us? So showing up with, hey, this is what— this is my pain. This is what I'm dealing with. And I'm now going to see if you're going to take care of me used to be a really scary thing to do because when I did that, it didn't happen. But it did. And so I felt a sense of joy and a sense of love and a sense of truly being seen. And in fact, it translated into a higher sense of— commitment and dedication to the company, what we were trying to create, and more importantly, to themselves. Like, I don't think— it didn't matter that people were more dedicated or loyal to me. What I really wanted was for people to be more of who they were. And me being more of who I was allowed my team and the people around me to be more of who they are. And I think that mattered more than anything else.

That seems like a common theme when people have, haven't avoided abandonment trauma, they'll, they'll feel like others aren't there for them even when they are, because they're just not letting it in. And something that you just described is that having worked through this, you want people to be there for themselves. And in that way, you're there for them even more. And the extent that they are with you, you, you allow that in and allow that to impact you. And I'm curious to go back to that moment with your father. What led up to this moment where after 40-some years, you were able to approach him to speak about this, became aware of this feeling that you had with him and then approached him in such a way that you had the conversation where you never even left the parking lot and it was just, you know, tears and heart-opening conversation. Wow.

Well, Joe hasn't said anything yet in this conversation.

I'm just enjoying listening. Goodness gracious.

But I give him a lot of credit for pushing me to go deeper into understanding myself. And I've learned that there are layers of trauma that I've dealt with and layers of abandonment that I've dealt with. But at its core, that was really it. And so what allowed me to realize that It was a journey. My first conversation with Joe was like, I think I have some daddy issues that I need to work on. That was like 2 and a half years ago. It was really like more facetious and true at the same time. But it was just a recognition that I knew I could be a better person. I could show up better as a mother, as a wife, if I process some of the things that happened to me as a child. And over the course of 2 years, as I unpacked what really was holding me back and what I was fighting for, I think I spent 2 years of really working with Joe on understanding why I was always trying to prove something to somebody. And fight for something. And I was the one who would get out there. Like, if we need to take this mountain, we will take the mountain. I will be the first one up there. Like, you're coming with me. And we're going to do whatever it takes to win. And I was always trying to prove something. And that could translate into ambition. And so people saw that ambition and said, wow, she's really ambitious. Like, we're going to work with her because we're going to get there because she wants get there. But underneath it was this desire to prove and this desire to fight. And what I realized was that the proof and the fighting was— something was underneath that. Underneath that was this feeling that I needed to prove something because if I didn't, I would be abandoned again and again and again. And as I went back to the original source of where that started, that's really where it started. It is the case for me, and I know it's very cliché, that the things that happen to us as children often shape who we are. And that's ultimately what happened. So I had to now say, well, I can't just worry about some manager that I had who didn't promote me. And so, they abandoned me because I didn't get promoted, right? All these things go back to abandonment. At one point, I had to go back to the original source, which was the relationship with my father. And we had— Dad and I had developed a really good relationship over the last 10 years. So, we weren't at odds with each other. We didn't hate each other. We loved each other. And yet, that conversation hadn't happened. And so, I decided that this year, I wanted him to know all of who I am because I had changed. And I wanted him to see me for who I really was. And in order for that to occur, I needed to say these words to him. It was so scary. I wrote— I had a script. I wrote it down. I took many notes. Joe is laughing because he knows. I practiced. I practiced all possible scenarios, like how this conversation could go. It could go really good. It could be really bad. He could reject me again. I don't know what was going to happen. But what I did know was that I wanted to say it. And I became OK with any outcome, meaning if there was no watershed moment, if he did pretend like nothing ever happened, I became okay with that possible outcome. And so because I think because I was okay with any outcome, I just freely spoke. And I spoke from a place of empathy, understanding, but also wanting him to know my truth and how I was feeling and not expecting anything but wanting an apology. And the first thing he said was, "I'm sorry." And I, I just— that was it. So it was wonderful.

Yeah, it's fascinating that what you described there in this moment of coming to him and sharing this, you know, you had some fear, you had a script, you were prepared in a way, but also you had done, done the internal work so that even if he did abandon you, then, then that was an acceptable outcome. And you also allowed yourself to want the connection with him. And having those two things at the same time, I see, is really important here. And I'm curious how, how having that when you show up in your team, when you show up as a CEO, how does that interact with the history that you had of showing up with a lot of fight and with a lot of something to prove? How does that, the way that you showed up with your father, impact the way that you show up with others?

It's very different now. Unfortunately, we can't invest in every company that we see with the Opportunity Fund, but we invest in Black, Latinx, and Native American founders. And I want all of them to be successful, but we're not going to be the person who— the company that provides the capital. And so when we pass on a deal and it's someone that I know, I talk about, I want to stay connected with you. I want you to be successful. And here's why we're not going to invest right now. It's a very different conversation. And almost always, the response that I get is a thank you, which is weird because I'm basically saying we're not going to give you money, or someone on our team has said We're not going to give you money. And then they want to know why. And they ask me and I tell them, and then they say, thank you.

You're abandoning them.

That's weird, right? But they say thank you because they appreciate the honesty. And unfortunately, in the world of venture capital, a lot of times you get ghosted. They don't actually respond. They don't give you the truth. And I can speak from a place of truth and love. And even if that truth doesn't get the founder, the outcome that they want, it comes from a place of love and it comes from a place of wanting connection, which I think sets us apart as a fund. But it's very different from how I would have gone into those situations in the past.

You came into this work hesitantly and with, you know, with some skepticism. And, and just recently you, you were talking to a friend about the work and you said to me something like, I don't know, she probably thinks I'm crazy when I was talking about the work. And I just got an email from her saying, I talked to Stacy. I'm totally motivated. When can we start?

Go, go, go, go.

Right? So, tell me about your journey about accepting, you know, doing the work. It feels crazy, like, and expressing that work to other people. Like, what is that? What has that been like for you?

It's hard to describe because people will ask me, who is Joe? And then, and I'll say, well, he's a coach, but he's not like an executive coach like most people have. Was he a therapist? He's not a therapist because he's not licensed. And anything like that. So he's just this person. And so you start with something like that and everyone looks at you in a weird way like, "What are we talking about here?" So what I try to say is this, working with Joe changed who I am as a person. And he's helped me become a better person. And one of the reasons why is because it's the work that I've put in and not the work that he's done. And so I told this friend that the first time I had a meeting with Joe, I was like, over it. I was like, I'm not going to do this. I don't have time for this. And he was like, OK. And so— and that OK was like, whoa. He didn't try to save me. He didn't try to keep me. He basically was like, if you don't want to do the work yourself, OK. If you do, I'm here. So it was a choice to lean in that had to be completely my own. And that was very different. And then I remember— and, Joe, you may remember this— I asked you going into 2021, I was like, I'm not really sure what I'm going to work on this year. I've done so much work in 2020. And there was a pandemic. There was a social justice. There was all sorts of stuff that happened. I feel like pretty good. And Joe, you said, well, what I do know is that if you don't come up with something that you want to work on this year, you won't work on anything. And it was this moment of realizing that I I still had complete ownership on how deep I wanted to go in my own development and how much I wanted to push myself. And it was, again, my decision. And when I tell people that, it sounds crazy because it's like, what, you want to really work on yourself that deeply to process emotions like fear and anger and pain and hurt and abandonment and trauma? And on the other side of it is love and joy, how does that happen? The answer is it's a journey. And my journey is very different than what someone else's journey might be. But the important thing is to be willing to take a step, one step on that journey, and then the next step on that journey. And even if it gets scary, actually when it gets scary, that's when you really have to take the step, which sounds crazy.

Yeah. Something really, really interesting there is that you described that before in your life you were a fighter, you would really push, you would— you were the CEO, right? You were the one who was just going after it and pushing yourself. And then the way that you're describing pushing now is a very different kind of push and The first kind of pushing is one— if it's coming from an abandonment wound that's being avoided, then it's actually abandoning yourself in, in the driving and in the pushing. And I think this, this can occur often when people do self-work. They'll push themselves without letting themselves be ready for what they're pushing themselves into. And it's more of an invitation. And the way that you're describing it now is that, you know, you, you see the invitation. You spoke with Joe. Joe gave you an invitation and you decided how much you wanted to move into it. And in that way, you were abandoning yourself less than you previously had. And this process of going in and doing the work isn't one of pushing yourself into it, but one of just letting yourself do it, letting yourself naturally follow what's next for you and have a question come up to work on.

That's true. And I like to say that I don't have to prove anything to anyone anymore. And there's a freedom that comes along with that because I don't have to step outside of myself. I can just stay all of who I am and show up with all of who I am. And whatever presents itself is what's there. There's an element of comfort, calm, peace that I have now that I didn't have 2 years ago, 3 years ago, or 5 years ago.

Looking back on yourself 2, 3, 5 years ago, how do you feel towards that version of yourself at that time?

I love her. I love that little girl who was like sad when her dog died. You know, who was 14 and wanted a Coach bag and so said she was going to, like, make as much money as she could so she can buy as many handbags as she wanted, who was, you know, terrified to talk to her father and then she did, and who built a great company and hired lots of people and motivated and inspired lots of other little Black girls. To pursue careers in technology. I love all of who she was because I couldn't be who I am today if she hadn't been who she was 5 years ago. I love her. I keep her. I don't want to lose her. She's like a part of me.

One of the things that I get a lot when I work with people, particularly for the first time, is I get some sort of version of— they see the thing and then they ask, how do I keep the thing? They see through the abandonment, for instance, and then they're like, the first thing is, how do I keep this recognition? Or how do I stop acting like I was when I was in abandonment? Or some version of like, now that I see it, what do I do? And I'm wondering what advice or what thoughts do you have on that for those people? Because it's like so many people are just like, what do I do next? What do I do next? What do I do next so that I can be out of this emotional state or so that I can not have this pain in my life anymore? And it's something that I just noticed doesn't come up very much with us. That's never the case. It's somehow you, you see the realizations differently. So I was curious, what's your, what are your thoughts there?

I have a sense of awareness and I'm more comfortable, I think, knowing that I don't always have to feel everything all the time, but I know over some period of time, I'm a different person today than I was some time ago. And so reminding myself of that has really helped me want to think about what could be next. I'm also a person of faith. Joe, you know I'm a Christian. Brett, you don't know me, but I'm a Christian. And my faith has really guided me throughout my life. I mean, God has carried me at times when I couldn't carry myself. He's been there for me when I didn't think that I needed the Lord. I've prayed to God for things that I've needed, and he's blessed me in so many ways. And so I'm grounded in that faith, Joe, that helps me know that even when I don't feel like I'm making progress, somewhere, it's for a reason too. And there's probably something on the other side of that, that wall or that barrier or that seeming obstacle that's going to be okay, that's going to be good. And just sometimes I gotta wait for it, or sometimes I gotta jump over it. I just gotta pray about it, you know. So that, that helps me, um, sort of deal with the process of doing the work.

I'm curious how your relationship to your faith has shifted from having done this work and how, how having something to prove or abandonment might have shown up in your relationship to your faith prior to having these self-reflections.

So much in so many areas. It's Even in feeling abandoned, I always know God is with me. And yet it's not easy to remember that truth when you're in the moment. I was diagnosed with breast cancer and found out about my diagnosis when I was traveling. I was traveling for work. I was in New York. I was by myself and super scared. Didn't know what was going to happen to me. Called my mom, cried. She's like, "Everything's going to be okay." That's what a mom should say. Like, that's it. She's like, "Everything's going to be okay." She was the perfect mom in that moment. Called my husband. He was dealing with the kids. I didn't even tell him because I figured, you know, He's trying to get the kids to sleep. I'm traveling. It's crazy. So I was like, I'm not going to lay this news on him in this moment right now. Hung up the phone. And my pastor called me. And he said, "Hey, Stacy, you know, I'm just checking in on you. I know you had this biopsy. You're waiting on the results. And I don't know if you got the results yet, but I just wanted to call and see how you're going. How's it going? Check on you." And I literally just started weeping because— and I said, hey, I just, you know, I told him. And he prayed for me in that moment. And he said to me, he said, you know, you're gonna cry and you're gonna be sad, but I want you to know that God is with you. And he's like, and that's okay. He was like, you're— and I was like, I'm by myself, I'm in this hotel. And he's like, just 'Just cry all night. Just sit there. Put on some church music if you want to, you know, whatever makes you feel better.' And he's like, 'And I'll call you tomorrow,' after he prayed with me. So I sat, I hung up the phone, I put on some music, and I just like sat in this corner and I just cried and cried and cried until I was done. And there was this emptiness that I felt of like, wow, this is like the bottom of something, but I'm still being held. And in that moment of feeling like I was alone and abandoned, God was there with me. Why did my pastor call me in that moment? Like, I knew that was something. So as I sat in that emptiness I realize I am never, ever, ever alone, ever, because my God is always with me. And so when you ask about my faith, I always get emotional about this. You ask about my faith and abandonment. I know I'm never alone because I know I have my faith. And that has shown up for me in so many ways. And yet, I still have what need to process it in all aspects of my life. So I don't know if this is important for the podcast.

It is.

But it was important for me to tell the story. Yeah.

And I also just love the beauty of that story of feeling your pain, being there. You were with yourself as well.

Yes.

Wasn't just God with you. It was also you being with all of your pain until it had been felt all the way through. And then what happened? You, you reached this, this point of empty— emptiness. And then, and then what?

I was empty, and I felt truly held. And it was the moment that I realized that in my life, I've always felt like I was the one who could do it. Do it myself and make it happen. And in this moment, I couldn't. I couldn't do it myself because I was scared. I didn't know what was going to happen. And I truly had to depend on someone else, in this case my God, to comfort me. And the comfort came. So it felt like this blanket just came over me. It was super warm and cozy and cuddly. And I just relaxed into it and like fell asleep. That's what happened.

What happened when you woke up next?

Woke up in the morning and was— I had this sense of, wow, all right, I can do this. And I needed that sense because it was the opening of the Nordstrom store in Manhattan, the grand opening. And I had to show up as a board member. And they, like, cut a ribbon. And everyone was cheering. So— and I could show up and genuinely be excited about this opening in the face of what just happened the night before. Because I knew God had it. I had it. We had it. It was going to be OK. And I'm so thankful to have my health. Today.

So part of the question that I still haven't fully grokked is if you were just to say how— so there's the time we like when we first start working together to after the talk with your dad, how has, if at all, your relationship with God changed?

I think we have a more open relationship, I would say. That's how I would describe it. My prayer life is really about what God wants for my life, what I want for my life. It's like mutual. And it's not from a, you know, please make this happen for me. It's more like, I want this. If you want it, it'll happen. It's very different. It's very— I feel like I'm walking alongside. He's walking alongside with me all the time and constantly there. So it's conversational. It's open. It's not this sort of hopeful thing. It's more like a knowing that I've got that relationship and it's not ever going anywhere. And I don't have to worry about whether it's going to be there. Or not. It's just, it's just there. And it feels very natural. And I love it.

So there's a whole bunch of young CEOs out there, whether they're part of the Opportunity Fund or otherwise. What is your advice or thoughts for them about doing self-discovery work and business and that, like that intersection? What do you want to tell them? How, what gift would you want to give them around this?

I would want them to know that part of becoming a CEO or founding a company requires a little crazy because you're seeing the world the way other people don't see it yet. And then you're trying to convince them that this is the way the world should operate. And that might feel like you're alone. And, and so I would invite you to do some self-discovery, some learning, to really discover what grounds you, what, what's true for you, what keeps you going, what keeps you motivated, and share that with other people. Because the more you open up about who you truly are The more you continue to discover who you truly are, the more people will want to support your vision and your mission and your goals and all that stuff. None of that really matters unless they see the human and all of the human that you are. That would be my gift.

Beautiful.

Beautiful.

Thank you so much, Stacey. Thanks for joining us, Joe.

Oh, total joy to be with you both. But Stacey, ah, just feels so good to listen to you. Thank you.

Yeah, thank you. Thank you for having me.

Thanks for listening to The Art of Accomplishment. If you enjoyed what you heard today, please subscribe and rate us in your podcast app. We'd love your feedback, so feel free to send us questions or comments. You can reach out to us, join our newsletter, or check out our courses at artofaccomplishment.com.