“We can all relate in some way to being underestimated at some point,” says Arlan Hamilton, founder and managing partner of Backstage Capital, a venture capital firm dedicated to minimizing funding disparities in tech by investing in high-potential founders who are people of colour, women, and/or LGBT.
“As much as we wish it weren’t so, we still live in a world where being underrepresented often means being underestimated,” she says. In her new book, It’s About Damn Time, Hamilton wants to show others that being undervalued simply means that a big upside exists. Because even if you have to work twice as hard to get to the starting line, she says, once you are on a level playing field, you will sprint ahead.
Her story is the proof. In 2015, on food stamps and sleeping on the floor of the San Francisco airport, Hamilton started working on her dream of breaking into the venture capital business. She wanted to invest in the ideas and people who didn’t conform to the stereotype of what a founder should look like. Today, her firm Backstage Capital has invested nearly $10M into 130 startups led by underestimated founders.
Hamilton recently made history as the first Black woman, non-celebrity on the cover of Fast Company. She’s on Fortune magazine’s 40 under 40 list, and Vanity Fair magazine’s The New Establishment List.
In Hamilton’s new book, It’s About Damn Time, she argues that a privileged background, an influential network, and a fancy college degree are not prerequisites for success. Through the lessons learned on her remarkable journey, she inspires us all to defy other people’s expectations and to become the role models we’ve been looking for.
Hamilton recently sat down with Leigh Doyle, Vice President and Co-founder of DJG, to talk about the importance of multiple streams of income, why it’s time to recalibrate what we think work means and how to cultivate resilience.
The transcript below has been edited for clarity.
Leigh Doyle: When we look back on this, what do you imagine will be some of the lessons learned along the way?
Arlan Hamilton: Having more of a runway for ourselves. Having more in front of our feet than a lot of us have [and] the idea of not just having one job as a norm. I’m really, really into multiple income streams. I was before coronavirus and I am now.
I have seven and I was broke five years ago. I had no money. No, no money. So those things were built. There was no privilege added to it — except for the augmented privilege that I feel like I siphoned over the past few years. But, I think it’s more important than ever for us to have multiple [streams] we can pull from. For so long, especially like in the US, it’s about having the one gig. And if you have more than one gig, you’re considered someone who’s not focused, or you don’t care enough for the thing, or you’re working for one person and one mission only and that’s the only thing you can do. I think we’re being caught flat-footed because that’s the way we are.
Along with different ways to work with each other and even socialize with each other, one of those main things will come away from is thinking…is should I have this empire of my own that doesn’t need your rules of how you think things should go, so that I make sure that I’m okay. I can take care of the people that I care about and I can take care of strangers. There’s this multi-layered piece to your empire rather than, well I had the one job and I just lost it and what do I do now?
Doyle: This ties into the idea of, I think you called it, hustle porn in your book, how do we separate the idea of building an empire and having multiple streams of income, but not giving into that hustle, hustle, hustle?
Hamilton: I have a new online course and I just interviewed a friend of mine who was a case study [for it]. I’m trying to tell everybody bootstrap and don’t necessarily go for outside funding. She did a million dollars in revenue last year with a bootcamp to teach you how to build apps without code — it’s called Apps Without Code — and she works two days a week. That gives her the ability now to take a ballet class online. It gives the ability to do a second thing. Or a third thing.
I even sent a text this morning to my team and I said: Remember, work smart not hard. I’m not gonna be checking your hours. I’m gonna be checking your execution. So I appreciate you challenging that because I absolutely don’t want to be represented as someone who’s saying you gotta do everything and be everything. I’m saying there are some interesting ways we can recalibrate and think about what work means, what it means completely taken apart, dismantled and put back together.
Doyle: What can the rest of us learn from women, people of color and those who’ve been traditionally overlooked about how to turn being underestimated and our greatest advantage?
Hamilton: Everyone that you listed is who I invest in and have been working with for the past nearly 10 years, specifically on startups.
We can all relate in some way to being underestimated at some point. Whether it’s walking into a room and someone thinking that you work there rather than you’re about to be the headlining speaker. Or some people are the CEO of the company and they’re mistaken for the secretary because they’re a woman.
There’s a grace and a dignity that the majority of us hold in those spaces even. I call it paper cuts — these micro aggressions. I call them paper cuts because when you get a paper cut it hurts like hell, but it’s not easy to explain or run around and tell everybody about. But it’s real. So there’s this dignity that I think that a lot of us have that really inspires me and it’s easier to pull from that during the harder times. On a day-to-day basis, we go through that, so in the more difficult times, that if we can go through that daily perhaps you can go through something [more difficult] in that moment.
Doyle: Obviously, through your story, embody resilience. So for people reading or watching this video, how do you cultivate resilience?
Hamilton: You have to adapt. You adapt or die, right? It’s scientific or biologic. You have to adapt. I feel like I’ve been swimming in this pool of molasses for most of my life. It has been very difficult to push and pull in a lot of cases. In other cases, it has been wonderful and I’m grateful. But for a lot of the time, it’s been an uphill battle. You develop a muscle for it.
Then, I draw on the strength of other people around me to inspire me. We all do that. Even people who I don’t know. I’ve always said that Oprah has been my teacher. Will Smith has been my teacher. Richard Branson has been my teacher and has been my mentor without even knowing it. Sometimes all you have are the voices of others who have gone before you. Who have left their breadcrumbs for you in the way of books and their words and what they have accomplished.
Doyle: Do you hear from people that you are a source of inspiration for others now?
Hamilton: I’ve heard it. I get this wonderful feedback from a lot of people. It’s incredible and sometimes can be very intense, especially if it’s face-to-face in a meeting. What I do though is compartmentalize. I make sure that I don’t feel like it’s them saying that about me directly. I try to kind of deflect it to what I represent and what purposely represented and gone out and sought out to do. In that case, it kind of feels like their emotion and their gratitude is more towards the work that we’re all doing and that feels really, really powerful to me.
