Brett and Joe interview Stacy Brown-Philpot, former CEO of Task Rabbit and founding member of the Softbank Opportunity Fund, on her journey through childhood abandonment to self discovery. Stacy identified that by choosing the path of self-exploration, she was able to feel through difficult emotions of fear and anger to find deeper love and joy. We will learn how her willingness to confront her past traumas has helped her become a more honest and empathetic business woman.
"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 is 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."
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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 is 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.
My name is Brett Kistler. I am an adventurer, entrepreneur and a self exploration enthusiast. I am here with my co-host, Joe Hudson. Joe is a business coach who has spent decades working with some of the world´s top executives and teams developing a unique model of human patterns that underpin how we operate with ourselves, each other and the world. A good entry point into this model is a mindset called VIEW, vulnerability, impartiality, empathy and wonder.
Through understanding and cultivation we learn to easefully drop into the VIEW state of mind, deepening self awareness and increasing our connection with the world around us. To learn more about this podcast or courses, visit artofaccomplishment.com
Brett: All right, everybody, I am really excited today. We have a three-way conversation today. This is Joe and myself, and joining us is Stacy Brown-Philpot. She is the former CEO of TaskRabbit and a founding member of the Softbank Opportunity Fund. How are you doing today, Stacie?
Stacy: I am good. How are you?
Brett: I’m doing well and I’m excited to try this three-way conversational format.
Stacy: Me, too.
Joe: Me, too.
Brett: Tell us a little bit about yourself and what brought you to this work.
Stacy: I came to this work really initially not open minded, but eventually open minded, I would say. 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 four generations of women in the house that basically taught me how to depend only on myself in order to make things happen. 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. 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. It really centers around abandonment and fearing being abandoned because of things that happened in my childhood. Here I am.
Brett: Tell me a little bit more about that abandonment, how you came to recognize that this was something for you to feel into and what’s one pivotal moment of transformation where you started to work through this and experience it in a different way.
Stacy: 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. 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 people.
Overtime and through this work, I realized that the compartmentalization had served me well in terms of being a really good CEO who could operate well, who 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.
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. Because of that, because he just wasn’t around, I never knew how much he mattered to me, or I mattered to him. 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 I had growing up experienced. Just knowing that he mattered to me really would have been everything for me.
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. I told him that, because of how we grew up, I never thought that I mattered, because he was not around. It was a moment where we were going to take a drive, Brett, and go and have this conversation. We actually never left the parking lot, because he just opened up and both of us were in tears just sharing. He said to me you have always mattered to me, and I don’t think I knew what I expected from that conversation.
All I wanted him to know was how he made me feel, but when he said you’ve always mattered to me and in fact there are some things 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. That pivotal moment for me was just a release of 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.
Brett: How did that impact your life as a leader? Looking back on your time as a CEO in the way you just described, being the CEO who was just getting it done, super independent, doesn’t need anybody, how was that negatively impacting your business and your relationship with your team? How much did you notice at that time? How much do you notice it now?
Stacy: 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 am 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 there were only glimpses and moments where I would do that. For example, when George Floyd was murdered, the only thing I could do at that time was show up as a black woman who was in pain. It didn’t matter what title I had. Nothing mattered in that moment.
I could tap into that place, but I wasn’t able to tap into it often and frequently. When I did, it wasn’t often a very scary thing for me to do and not a very easy thing for me to do.
Brett: What happened as you started doing that more scary thing, stepping into who you are with acceptance of that feeling of abandonment?
Stacy: 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, it felt so good. As a CEO, everybody wants you to take care of them, and they come to you with the hardest problems, the most complicated problems, the ones that have the least amount of information to solve, and we take on that responsibility. We forget that somebody needs to take care of us, too, and so who is going to do that? Who is going to take care of us?
Showing up with this is my pain. This is what I am dealing with, and I am now going to see if you are going to take care of me. That used to be a really scary thing to do, because when I did that, it didn’t happen, but it did. 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. It didn’t matter that people were more dedicated or loyal to me. What I really wanted, was for people to be more who they were, and me being more who I was, allowed my team and the people around me to be more of who they are. I think that mattered more than anything else.
Brett: That seems like a common theme when people have avoided abandonment trauma, they will feel like others aren’t there for them even when they are, because they are just not letting it in. Something you just described is having worked through this, you want people to be there for themselves. In that way, you are there for them even more. The extent they are with you, you allow that in and allow that to impact you.
I am curious to go back to that moment with your father. What led up to this moment where after 40 something years you were able to approach him to speak about this and became aware of this feeling you had with them and then approached him in such a way that you had the conversation where you never even left the parking lot? It was tears and heart opening conversation.
Stacy: Wow, Joe hasn’t said anything yet in this conversation.
Joe: I’m just enjoying listening. Goodness gracious.
Stacy: I give him a lot of credit for pushing me to go deeper into understanding myself. I’ve learned that there are layers of trauma that I’ve dealt with and layers of abandonment I’ve dealt with, but at its core, that was really it. What allowed me to realize that it was a journey. My first conversation with Joe was like I think I have some daddy issues I need to work on. That was like two and a half years ago. It was really 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 processed some of the things that happened to me as a child.
Over the course of two years, as I unpacked what was really holding me back and what I was fighting for– I spent two years really working with Joe on understanding why I was always trying to prove something to somebody and fight for something. I was the one who would get out there. If we need to take this mountain, we will take the mountain. I will be the first one up there. You are coming with me, and we are going to do whatever it takes to win. I was always trying to prove something, and that could translate into ambition. People saw that ambition and said, “Wow, she is really ambitious. We are going to work with her, because we are going to get there, because she wants to get there.”
But underneath it was this desire to prove and this desire to fight, and what I realized was that the proof and fighting, 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, again and again. 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 is very cliché that the things happened to us as children often shape who we are. That’s ultimately what happened. I can’t just worry about some manager I had who didn’t promote me, and so they abandoned me, because I didn’t get promoted. All of 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. 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. 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. In order for that to occur, I needed to say these words to him.
It was so scary. 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 of how this conversation could go. It could go really good. It could be really bad. He could reject me again. I didn’t know what was going to happen, but what I did know was I wanted to say it. I became okay 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.
I think because I was okay with any outcome, I just really spoke. 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. The first thing he did was I’m sorry. That was it, so it was wonderful.
Brett: It’s fascinating what you describe here. In this moment of coming to him and sharing this. You had some fear. You had a script. You were prepared, in a way, but also you had done the internal work so that even if he did abandon you then, then that was an acceptable outcome. You also allowed yourself to want the connection with him. Having those two things at the same time, I see, is really important here.
I am curious how having that when you show up in your team, when you show up as a CEO, how does that interact with the history you had of showing up with a lot of fight and with a lot of something to prove? How does the way you showed up with your father impact the way you show up with others now?
Stacy: 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. I want all of them to be successful, but we are not going to be the company that provides the capital. When we pass on a deal and it is someone I know, I talk about wanting to stay connected with you. I want you to be successful, and here’s why we are not going to invest right now. It is a very different conversation.
Almost always the response that I get is a thank you, which is weird, because I am basically saying we are not going to give you money or someone on our team has said we are not going to give you money. Then they want to know why, and they ask me. I tell them, and then they say thank you.
Brett: You are abandoning them.
Stacy: 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. Even if that truth doesn’t get the founder the outcome that they want, it comes from a place of love and a place of wanting connection, which I think sets us apart as a fund, but it is very different from how I would have gone into those situations in the past.
Joe: You came into this work hesitantly and with some skepticism. Just recently you were talking to a friend about the work, and you said to me something like, I don’t know, she probably thinks I am crazy when I was talking about the work. I just got an email from her saying, I talked to Stacy. I am totally motivated. When can we start? Go, go, go.
Tell me about your journey about accepting doing the work. It can feel crazy and expressing that work to other people. What has that been like for you?
Stacy: It is hard to describe, because people will ask me who is Joe, and then I will say he is a coach. But he is not like an executive coach like most people have. Is he a therapist? He is not a therapist, because he is not licensed in anything like that. He is just this person. You start with something like that, and everyone looks at you in a weird way, like what are we talking about here. What I try to say is working with Joe changed who I am as a person. He has helped me become a better person.
One of the reasons why is because it is the work that I put in and not the work that he has done. I told this friend that the first time I had a meeting with Joe, I was like over it. I was like I am not going to do this. I don’t have time for this. He was like, okay. That okay was like, woah, 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, okay. If you do, I am here. It was a choice to lean in that had to be completely my own. That was very different.
Then I remember. Joe, you may remember this. I asked you going into 2021. I was like, “I am not really sure what I am going to work on this year. I have done so much work in 2020. There was a pandemic, social justice. There were all sorts of stuff that happened, and I feel pretty good.” Joe, you said, “What I do know is if you don’t come up with something that you want to work on this year, you won’t work on anything.” It was this moment of realizing that I still had complete ownership on how deep I wanted to go in my own development, and how much I wanted to push myself. It was, again, my decision.
When I tell people that, it sounds crazy, because it is like 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 is a journey. 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. Even if it gets scary, actually when it gets scary, that’s when you really have to take the step, which sounds crazy.
Brett: Something really interesting there is you describe that before in your life, you were a fighter. You would really push. You were the CEO. You were the one who was just going after it and pushing yourself. Then the way you are describing pushing now is a very different kind of push. The first kind of pushing is if it is coming from an abandonment wound that’s being avoided, then it is actually abandoning yourself in the driving and in the pushing. I think this can occur often when people do self-work. They will push themselves without letting themselves be ready for what they are pushing themselves into. It is more of an invitation.
The way you are describing it now is you see the invitation. You spoke with Joe. Joe gave you an invitation, and you decided how much you wanted to move into it. In that way, you were abandoning yourself less than you previously had. This process of going 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.
Stacy: That’s true, and I like to say I don’t have to prove anything to anyone anymore. 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. Whatever presents itself is what’s there. There’s an element of comfort, calm, peace that I have now that I didn’t have two years ago, three years ago, five years ago.
Brett: Looking back on yourself two, three, five years ago, how do you feel towards that version of yourself at that time?
Stacy: I love her. I love that little girl, who was sad when her dog died, who was 14 and wanted a Coach bag and said she was going to make as much money as she could so she could buy as many handbags as she wanted, who was 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 five years ago. I love her. I keep her. I don’t want to lose her. She is like a part of me.
Joe: One of the things 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 I keep the thing. They see through the abandonment, for instance, and the first thing is how do I keep this recognition? How do I stop acting like I was when I was in abandonment? Some version of now that I see it, what do I do? I am wondering what advice or what thoughts you have on that for those people. So many people are just like, “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.”
It is something I just notice doesn’t come up very much with us. That’s never the case. Somehow, you see the realizations differently. I was curious what your thoughts are there.
Stacy: I have a sense of awareness and I’m more comfortable, I think, knowing that I don’t have to always feel everything all the time. But I know over some period of time I am a different person today than I was some time ago. Reminding myself of that has really helped me want to think about what could be next.
I am also a person of faith. Joe, you know I am a Christian. Brett, you don’t know me, but I am a Christian. My faith has really guided me throughout my life. I mean God has carried me at times when I couldn’t carry myself. He has been there for me when I didn’t think I needed the Lord. I have prayed to God for things that I have needed, and he has blessed me in so many ways. I am grounded in that faith, Joe, that helps me know that even when I don’t feel like I am making progress somewhere, it is for a reason too.
There’s probably something on the other side of that, that wall or that barrier, that seeming obstacle that’s going to be okay, that’s going to be good. Sometimes I’ve got to wait for it, or sometimes I’ve got to jump over it. I’ve just got to pray about it. That helps me sort of deal with the process of doing the work.
Brett: I’m curious how your relationship to your faith has shifted from having done this work, and how having something to prove or abandonment might have shown up in your relationship to your faith prior to having these self-reflections.
Stacy: So much in so many areas. Even in feeling abandoned, I always know God is with me, and yet it is not easy to remember that truth, when you are 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. I didn’t know what was going to happen to me. I called my mom and cried. She was like everything is going to be okay. That’s what a mom should say. That’s it. She was like, everything is going to be okay. She was the perfect mom in that moment.
I called my husband. He was dealing with the kids. I didn’t even tell him, because I figured– He is trying to get the kids to sleep. I am traveling. It is crazy. I was like I am not going to lay this news on him in this moment right now. I hung up the phone, and my pastor called me. He said hey, Stacy, I am just checking in on you. I know you had this biopsy, and you were waiting on the results. I don’t know if you got the results, but I just wanted to call and see how it is going. I literally just started weeping. I told him, and he prayed for me in that moment. He said to me, you know, you are going to cry, and you are going to be sad. But I want you to know that God is with you. He was like, that’s okay. I was like I am by myself. I am in this hotel. He was like just cry all night. Just sit there. Put on some church music if you want to, whatever makes you feel better, and he was like, I will call you tomorrow after he prayed with me.
I hung up the phone. I put on some music, and I just sat in this corner, and I just cried. I cried and cried until I was done. There was this emptiness that I felt of like, ‘wow.’ This is like the bottom of something, but I am still being held. 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? I knew that was something. As I said in that emptiness, I realized I am never, ever, ever alone, ever because my God is always with me.
When you ask about my faith, I always get emotional about this. You ask about my faith and abandonment. I know I am never alone, because I know I have my faith. That has shown up for me in so many ways, and yet I still have the need to process it in all aspects of my life. I don’t know if this is important for the podcast.
Joe: It is.
Stacy: It is important for me to tell the story.
Brett: I also just love the beauty of that story of feeling your pain. Being there, you were with yourself as well. It 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. Then, what happened? You reached this point of emptiness, and then what?
Stacy: I was empty, and I felt truly held. It was the moment that I realized that in my life I’ve always felt like I was the one who could do it myself, 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. The comfort came. It felt like this blanket just came over me. It was super warm, cozy and cuddly. I just relaxed into it and fell asleep. That’s what happened.
Brett: What happened when you woke up next?
Stacy: I woke up in the morning. I had this sense of, “Wow, all right, I can do this.” I needed that sense, because it was the opening of the Nordstrom store in Manhattan, the grand opening. I had to show up as a board member and cut a ribbon. Everyone was cheering. I could show up and genuinely be excited about this opening in the face of what had just happened the night before. I knew God had it. I had it. We had it. It was going to be okay. I am so thankful to have my health today.
Joe: Part of the question I still haven’t fully grokked is, so there’s the time when we first started working together to– after the talk with your dad, how has, if at all, your relationship with God changed?
Stacy: I think we have a more open relationship. I would describe it. My prayer life is really about what God wants for my life, what I want for my life. It is mutual, and it is not from a please make this happen for me. It is more like, “I want this. If you want it, it will happen.” It is very different. I feel like I am walking alongside. He is walking alongside with me all of the time and constantly there. It is conversational. It is open. It is not this sort of hopeful thing. It is more like a knowing that I’ve got that relationship, and it is not ever going anymore. I don’t have to worry about whether it is going to be there or not. It is just there. It feels very natural. I love it.
Joe: There are a whole bunch of young CEOs out there whether they are part of the opportunity fund or otherwise. What is your advice or thoughts for them about doing self-discovery work and business and that intersection? What do you want to tell them? What gift would you want to give them around this?
Stacy: I would want them to know that part of becoming a CEO or founding a company requires a little crazy, because you are seeing the world the way other people don’t see it yet. You are trying to convince them that this is the way the world should operate, and that might feel like you are alone. I would invite you to do some self-discovery, some learning to really discover what grounds you, what is 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, 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.
Brett: Beautiful. Thank you so much, Stacy. Thanks for joining us. Joe.
Joe: A total joy to be with you, both, but Stacy, it just feels so good to listen to you. Thank you.
Stacy: Thank you for having me.
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