09: Arlan Hamilton, Knowing When to Pivot, Being Grown, and Leaving Well
Arlan is the Founder and Managing Partner of Backstage Capital, has raised more than $30M, and has invested in over 200 companies led by people of color, women, and/or folks from the LGBTQ community.
In today’s episode, Arlan shares her take on fear, change, and courage, and how to manage this trio of realities we all face. We also discuss making decisions on how we want our life to look, and the importance of spreading light everywhere it’s possible.
“There is change in transition that you can then control. When I think about that I think about the change I wanted to see in venture capital and the investing ecosystem. I wasn’t seeing as many faces writing the checks and influencing decision and behavior the way I wanted to. I envisioned the future, it was only five years ahead and in that five years, I thought so much can change if I just dare to keep going.”
Additional quotes:
“Being able to withstand change is what sets people apart.”
“People have a really interesting view of other people’s time, or what you should be doing: ‘you can’t step down, you can’t change jobs, you can’t leave your job to start a company, you can’t leave your company to go back to corporate.’ If that’s what you want to do, then you do you. You’re grown.”
“Leaving well is leaving on your terms, in your own time. Leaving for what the next chapter of your life is, even if the pages are blank.”
Resources from this episode:
Books by Arlan Hamilton:
Your First Million (pre-order)
To learn more about Leaving Well, click here.
My Bookshop.org Leaving Well library has many resources to support your workplace transition journey!
To support and contribute to the production costs of this podcast:
This podcast is produced by Sarah Hartley.
Transcription:
There is change in transition that you can then control. When I think about that I think about the change I wanted to see in venture capital and the investing ecosystem. I wasn't seeing as many faces writing the checks and influencing decision and behavior the way I wanted to. I envisioned the future, it was only five years ahead and in that five years, I thought so much can change if I just dare to keep going in, in my idea here.
This is Leaving Well, where we unearth and explore the realities of leaving a job, role, project, or title with intention and purpose. And when possible, I'm Naomi Hattaway, your host. I will bring you experiences and lessons learned about necessary endings in the workplace, with nuanced takes from guests on topics such as grief, confidence, leadership, and career development.
Braided throughout will be solo episodes sharing my best practices and leaving well framework. Expect to be inspired. Challenged and reminded that you too can embed and embody the art and practice of leaving well, as you seek to leave your imprint in this world. Arlen Hamilton is the founder and managing partner of Backstage Capital, has raised more than 30 million, and has invested in over 200 companies led by people of color, women, and or folks from the LGBTQ community.
Arlen, how would you describe your relationship with change and transition? Uh, intimate change and transition happens so often in my life that it's the new norm, I guess. And I've become very adaptable to it doesn't mean that sometimes it, you know, doesn't rock me, but I've just become adapted adaptable to it.
In fact, there is a study that was created that was about, um, adaptability quotient, you know, you have and and and then there was and that study used me as an example. To make its point, because of all the things that are thrown my way personally, but mostly through my company's backstage, capital, higher runner, et cetera, the different initiatives and and movements and in some ways that I've been able to be a part of.
Yeah, so that's a really interesting point. When you think about change and transition is something that. It sounds like sometimes you're the one, maybe not in control of or, or, um, I don't know, at the, at the helm of you're the one that is reacting and responding to market to what the world needs. So does that change at all how you advise the folks that you work with around change and transition?
Yeah, of course. Being able to withstand all of that is what sets people apart. It's, I did an interview with Mark Cuban right at, as COVID was hitting. And so this interview was live in front of several hundred, I believe, entrepreneurs who were scared and he and I were scared. And the first thing we started talking about, and you can still find that on YouTube, actually.
The first thing we, we started talking about was like. That we're both human. He and I, I was surprised by what he said. I was surprised that he was scared because he has billions of dollars. I would think he would be like, um, I'm secure in my, in my castle, um, even though I know him to be a very grounded, uh, individual and caring individual.
I would think that he would not be as scared as he said he was, but he also said this is the moment that leaders are made. This is the moment where you can, you can, if you choose to, rise to the occasion, um, and if you're able to. So when I'm speaking to entrepreneurs, whether it's directly or through my books or other means, I'm always trying to give them that, those breadcrumbs of like, This is, this is not only how I got here was through change and being able to kind of withstand that, but it's not going to stop.
It still happens. It's the thing. It's like you never get to a point where you're like, Oh, I've made it. I've so quote unquote made it. And therefore I no longer have to worry about change coming at me. Now you think you alluded to though, there is change in transition that you can then control. And that becomes really interesting to when I think, when I think about that, I think about the change I wanted to see in venture capital and the investing ecosystem for startups a decade ago, I wasn't seeing as many faces writing the checks.
And influencing decision and behavior the way I wanted to, I mean, to say the least, and although there were some there who led the way and laid the foundation, it was very quiet. It was a very quiet movement. If at all, I. Envisioned the future, and this in this case, it was only 5 years ahead. I only looked 5 years ahead and in that 5 years, I thought so much can change if I just dare to keep going in in my idea here and you look back a decade.
Not only did things change so much in five years, but they've changed even more so in 10. And what's going to happen in another decade when we look back at, at the, what, at the tentacles of what this, what this was. And that gives me hope for the people and entrepreneurs I speak with and the leaders and the career professionals that I speak with is like, can you imagine what the world will look like five years and 10 years from now, if you do the thing.
Yeah. So you talked a little bit about some things, some things, fear and courage, and then also immunity. I think you were talking about Mark Cuban thinking, Oh, he's not immune to being scared. He's not immune to having fear that that kind of weaves through his work. What do you think is the relationship between fear and courage and change?
Are they do they all have to go hand in hand? Or can you kind of Broach one and then master a little bit more of the other. You're encouraging change. Yeah, I think you they all go hand in hand. It's varying degrees something. Some changes. And that's scary. Some changes is exciting. But if you're able to identify fear, identify it, that's a big deal.
And then, if you're able to identify it, then you can sort of, you can have control of it rather than it having control of you. It reminds me of Jesse Williams. He Webby award, I guess. And I think when you win a webby award, I should know because I'm on the on the judging panel. So I should know this, but I think when you win a webby award, you only get a few, like, a few words to say, like, 5, maybe it's 4 words or 3 words or whatever.
And his was. Maybe it's five words. His was scared. Okay, do it scared. Five words. That sums it up. And that was so, that's so powerful. That's so powerful. I thought that was so clever for him to do that. Yeah. So on the topic of leaving and change and transition, is there a recent experience or a moment that comes to mind for yourself about when you needed to leave something?
Yes, I needed to leave the idea and vision that I had for myself prior to it. Meaning, I think this is where a lot of our work would overlap is. I have been working on backstage capital for a decade and as they said before, it is a movement. There's a, there are a lot of moving parts and there are a lot of people affected.
And in the past, when I have tried to step away to have even do a sabbatical or just step away to change where people. Or in the in the organization, so I can have a little less on my plate. I have received absolutely public messages, but then private messages from people. You would not believe saying, don't go.
You know, don't you can't leave and. Then hits and then things happen where it's like, I actually can't if I want the company to keep going and thriving, I actually can't step away in any capacity. And so I had sort of wrestled with the idea or wrestled with the under the challenge of. Am I who I am, if I don't have.
This title, or this responsibility, or this figure headness of what I'm doing and not necessarily for me, but am I, is that going to disappoint too many people that I can that I can stand and then something beautiful thing happened and I turned 40 and almost 3 years ago and I stopped caring as much about.
That and I started thinking, and then we went through Covid and it just kind of gives you, once you're in it and passed a little bit of it, it gives you so much clarity. So many people PA perished, and I know we all know that, but do we know that? Do we think about that enough? So many people lost their lives, all ages beyond Covid.
Like there's all kinds of people who leave us and. It's really the older you get, the more you think through, like, what do I want my life to look like, rather than what should I do? And it's not necessarily people pleasing or vanity. It's really like, you don't want to disappoint a lot of times, but I, in the last year made very distinct decisions about what I want my life to look like and what that looks like.
And so I have. I have put people in place that make my day to day less crazy and makes the stability of backstage and runner my higher runner dot com. I, my company, my other company makes the stability of those things that do affect. So many people rock solid. Enough where if I then can, if I then decide, okay, now I want to do this other thing, or now I want to just spend 50 percent of my time here.
I can do that. And that was like, it doesn't happen overnight. You have to kind of plan for it, but that's been really freeing. And it was like, I had to walk away from what you think your life is going to be. Yeah, and that, that touches on so much about legacy. And not only just I think the legacy that we want to build for ourselves, but the legacy that we're inspiring and empowering and enabling for others.
I recently saw Kobe Bryant's wife, the late Kobe Bryant's wife, talk about his own legacy. And there was a, she had asked him at one point, Kobe? When you're injured. And he said, because there might be one person that saved up to see me play. And I think about you and your work so often. It's the same, it's the same kind of energy that you're putting out into the world.
What about the one? Yeah. Yeah. 100%. It's the why it's why I, uh, even leave room for the question of, you know, staying. And what the good thing about it is that I can do my work and I can affect people. People in a way that is just more aligned with what I want in this chapter of my life. Yeah, but yeah, that's something similar to that is when people often come up to me.
If I'm in certain circles, right? Most places, nobody knows who I am, but if I'm in certain circles, people will come up to me or they'll drive in to see me from speaking somewhere and or they'll see me at the airport or on an airplane or something like that. And I have made it a very distinct decision to.
As long as I can help it, um, help them not regret their decision to say hi to me or to drive to see me or to fly to see me. And that can just be in a few seconds of how I react to them. That to me, that's legacy 1, 1 person at a time. And I do that. It doesn't have to be in person. It can be online. It can be in, it can be in group settings.
It can be one on one, but I just, I don't want the person to regret putting themselves out there to say hi, or just to do the thing or spend the money or, yeah. And I got that from a few people, but I got that really growing up in the, in the live music business. Starting to go to concerts at 13 and then, and then working and concerts for a living starting in 21 at 21 and doing that for a decade before I started backstage and I would just see how different artists treated their fans and how different artists treated their friends and their, and the people that worked at the local venue and all the stakeholders, because we're all like the people in the audience are stakeholders to.
What's happening on stage. I think Taylor Swift is a fantastic example of that. So I watched what I liked about things, what I didn't like about things. And then I've also just experienced going up to somebody. I mean, as recently as this year, like going up to somebody and excited to see them and they're just like, they just don't have time.
For you, and it's like, I know people have a bad day and I don't try to just put, oh, that's who they are, but it does. It does have an effect on you. Yeah, you know, so I like to just spread a little bit of light and that in that way. I love that, especially when so much of someone's work is on the behalf of stakeholders.
Then to not have that response when stakeholders come up and say, I really appreciate you. Yeah, that's right. That's right. It's not like, it's not like there's some 1 person on a pedestal. It's like, I really do think of it. Like, when I think of it, it's like, I think of investing. I think of, okay, this company has 100 percent of a cap table and these different people are investors and they're the founders.
They're the employees. They're the customers. They're all part of this. They're all they all affect the life of this company. Yeah, absolutely. So speaking of founders and investors, um, this might be investor speak your answer, or it might be more nuanced to the broader group of creators and entrepreneurs.
But what would be your advice to those listening on knowing when to pivot and when to leave? So that could be an investment. It could be something that they found at a company. It could be a project volunteerism anything. I'd love your answer. Yeah, I think it's not an answer. I give cannot convince somebody overnight to do this, but I do think that planting the seed of that mindset shift of in general, learn before 40, learn before I did, or if you're past 40, start learning today, right?
The whole tree planting thing was either 20 years ago was the best time to plant a tree or today. And that mindset, yeah. shift of, well, depending on what you believe, I believe you have this one time in this body to do the thing, to, to live the life. And I was looking at a photograph. I was looking at was a photograph.
I think it was a photograph and it was it was 5 years ago. And my wife and I were looking at this and we were like, that was 5 years ago. It seemed like it was maybe 6 to 12 months ago. If that. And life just passes you by. It just goes by so fast. And we all grew up hearing that. We all grew up hearing older people say that.
And we didn't pay attention. How were the older people? How were the older people? And guess what? One day we'll be the ancestors. Yeah. I don't know if you know, uh, Jaya John's work, but he has a quote that says, we are ancestors today in what we create. It's so powerful. Yeah. What would you say that we risk when we miss the opportunity to quit or when we wait too long to make a decision?
Is there such a thing as waiting too long? Yes, there is. And it just reminded me, there's a woman who wrote a book about this whole topic a couple years ago, and I can't think of her name at all or the book at all. But it was all Hmm. It's a couple of years ago, and I remember listening to a podcast that she did, and it was just so freeing.
It probably subconsciously had something to do with my. My mindset shift to, yeah, it's there can be a too late. That's the point. It can be a too late again, though. There's always hope. There's always I'm all I can't help, but be optimistic, even in a cold, hard world. So there's always hope. So maybe you did miss a certain opportunity, some certain boat, but maybe that there's a, there's another ship that will come in, but.
I think now, in this moment, if you haven't been already, now is the time to start thinking about it, start thinking about what you really want out of your life, what you really want to spend your hours doing on a day to day basis. Some things are not in our control or within our control, and many things that we don't even think are, are.
This, this might be a short answer. You might just say no, but is there anything that you have to say about change or transition that people might be shocked or surprised to hear? You're pretty transparent with what you have to say. I mean, it's not shocking, but just remember, for the most part, most people listening to this, you're grown, just remember that, just, you're grown, you get to, you know, if you have any children, they say, why?
You say, because I'm grown, and you can do the same thing for other adults. Why? Yeah, I think people have, some people have a really interesting View of other people's time or what you should be doing or all of those things or oh, you can't step down or you can't change jobs or you can't leave your job to start a company or you can't leave your company to go back to corporate.
That's like, so taboo, like, you're selling out in some way. If that's what you want to do, do you maybe it would be shocking to hear that. I am not someone who believes that everybody should have a company. And be a founder, even though I've invested in 200 companies and deal with companies day to day.
It's because of that, that I believe that there are so many people who are responsible for making companies what they are, and they are employee 2 through 1000 plus. And so, whether you are in corporate your whole life, or you're you went and dabbled and came back. None of that should I don't think should be judged.
So you're ready for your webby awards because you're five you do you you're grown? That's it. You do you you're growing a t shirt. That's it. Let me forget. That's the next I won't I love it. It's perfect. So as we wrap up Arlen, what what would you say that leaving? Well the concept of that what does it mean to you leaving on your terms?
Leaving in your own time, leaving for what the next chapter of your life is, even if the pages are blank. I love that. Thank you so much. We'll have all of the ways to connect with you and the things that you're putting out into the world in the show notes with links for everyone. I appreciate you. Sounds awesome.
Thank you. Thank you to learn more about leaving well and how you can implement and embed the framework and culture in your own life and workplace. Visit naomihattaway.com. It's time for each of us to look ourselves in the mirror and finally admit we are playing a powerful role in the system. We can either exist outside of our power or choose to decide to shift culture and to create transformation until next time.
I'm your host. Naomi Hattaway, and you've been listening to Leaving Well, a navigation guide for workplace transitions.