Ep. 198 – Arlan Hamilton, Founder of Backstage Capital & Author of It’s About Damn Time: How to Turn Being Underestimated into Your Greatest Advantage

Ep. 198 – Arlan Hamilton, Founder of Backstage Capital & Author of It’s About Damn Time: How to Turn Being Underestimated into Your Greatest Advantage

Arlan Hamilton is the founder of Backstage Capital, and author of the new book, It’s About Damn Time. This episode was recorded live as part of our IO live event series.

Inside Outside Innovation is the podcast that brings you the best and the brightest in the world of startups and innovation. I’m your host Brian Ardinger, founder of InsideOutside.IO, a provider of research events and consulting services that help innovators and entrepreneurs. Build better products, launch new ideas, and compete in a world of change and disruption. Each week we’ll give you a front row seat to the latest thinking, tools, tactics, and trends, in collaborative innovation. Let’s get started.

Interview Transcript

Brian Ardinger: Hey, Arlan. How are you?

Arlan Hamilton: Oh yeah. I’ve only been using Zoom a million times a day.

Brian Ardinger: Thanks for coming on the show here.

Arlan Hamilton: Yeah, thanks for having me.

Brian Ardinger: How are you handling the quarantine? Everything going well, relatively speaking?

Arlan Hamilton: Not everything, but you know, it’s the day-to-day that everybody’s saying. It’s very true. It’s getting me by. I feel pretty optimistic even though there’s some incredible things going on right now.

Brian Ardinger: Let’s get started. With me we have Arlan Hamilton.  She’s the founder of Backstage Capital and author of the new book called It’s About Damn Time. I am so excited to have you on the show. The question I wanted to start with is last week at this time, you’re talking to Mark Cuban and a week later you’re talking to us here in the middle of the country in Lincoln, Nebraska, and some other places.  What is your impression of the world that’s been disrupted? How do you see the world changing and how is that affecting yourself and your portfolio companies that you’re working with?

Arlan Hamilton: It’s something we’ve never seen before, and I think a lot of people are, are trying to figure it out. I think a lot of people are giving out some advice and trying to have it all figured it out. And I don’t know if we will yet. You know, I think we’re still in it. I think we’re still dealing with the trauma of it, even though a lot of us don’t even realize that’s what this is. And so I think for me it’s a slow and steady. It truly is a day-to-day. And personally, I feel at my best being a bridge to communication or connecting people, and that’s why I’m having so many conversations with people around the world during this time just to kind of keep my sanity and keep me feeling like I’m useful.

Brian Ardinger: I totally understand that. And I’d imagine for a person like yourself who is probably on the road a lot, I know you’ve been out in the marketplace, not only meeting with startups, but also talking about what it’s like out there in the real world. It’s probably more challenging to do that from a remote location, but we’re all on the same boat. You’ve got a new book coming out fairly shortly. It’s called, It’s About Damn Time. Can you give the audience a little bit of background on what the book’s about and some of the key stories or benefits that you hope people get from reading it?

Arlan Hamilton: Yeah. It’s about Damn Time: How to Turn Being Underestimated into your Greatest Advantage. I wrote it because I get hundreds and hundreds of inbound messages per day across multi-platforms. The number one thing I’m asked is, will you invest in my company or my idea? The second most frequently asked question is, will you be my mentor? And that doesn’t scale very well. But the way that it can scale is by writing this book and all of the things that I try to do on a daily basis online with all the resources that we give.

The book is my way of giving to someone, and I always try to imagine the person, right. Believe in myself in some cases, but given the person that may need it, the same thing that I received when I picked up Brad Feld’s book, for instance. Venture Deals 101 in 2013 or so, and all of these books that I’ve read along the way in my journey from going from broke and homeless on food stamps to raising more than $10 million and investing in more than a hundred companies. There’s so much in that journey and packed into the last five years that I think is relatable, believe it or not, relatable to a lot of people, because I’ve had all kinds of jobs and all kinds of obstacles, and it’s a relatable story.

It’s that, and it’s also the fact that when I was looking for these types of resources. They were mostly from white men in the business sections of these bookstores at the airport.  And the information was fantastic, and the people were fantastic, and I even know Brad now, which is such a wonderful journey. But it’s the same thing that drove me and still drives me to invest in underrepresented founders, is there should be better representation in business books that are written for multiple people and profiles, but by a black woman.

Brian Ardinger: Tell us a little bit about that journey. I know a lot of folks are familiar with your story. Tell us a little bit about, it really has been an amazing five years. I don’t know if you remember, but you and I actually met via Twitter probably about four or five years ago when we were spinning up the IO Summit, which was our first event. It’s been going three years.

Arlan Hamilton: I do remember, yes.

Brian Ardinger: And you pinged me, making sure that I had representation as far as audience and speakers, and you’ve got me connected with a couple of your portfolio companies to bring into the show.

Arlan Hamilton: I remember where I was sitting when that happened. That’s so crazy.

Brian Ardinger: What I found so interesting about that. You weren’t popular or big or you hadn’t been on Fast Company at the time, but you reached out and you were living what you talk about now, like being engaged in the community, helping your portfolio companies and fighting the good fight. That always impressed me about you, that you were out there telling the stories and making things happen. Even at the very early stages. Why don’t you tell the audience about what that journey has been like over the past five years? Going from quote nothing to being on the cover of Fast Company being at South by Southwest, all these kinds of things people aspire to, that most people don’t have a chance to do.

Arlan Hamilton: It’s funny because as many stories as I tell in the book, I haven’t gotten to all of them. There are many that have happened in the last, and that you just reminded me of one. In 2015, in March, which is like five years back. Right. I slept in a car with my mom, who was in her sixties at the time, so that I could attend the fringes of South by Southwest. Right. And nobody knew it. But that’s what I did. And it was not, because you know, to be kind of cool, it was with my mom. We didn’t have a place to live, but I want it to be there and try to meet people to raise the fund.

And this year, if it had gone on as planned, I would have spoken seven times in keynote positions. It’s just so intense to think about that. And then the Fast Company, I was on the cover of Fast Company, which is still crazy to say, the October, 2018 issue, I was a first non-celebrity black woman to be on it, and Oprah, Serena Williams, and Beyonce had been on it before as black women celebrities.

Brian Ardinger: Not bad company.

Arlan Hamilton: Not bad at all. And I wouldn’t have been able to afford a copy of Fast Company in 2015. I talk about all of the buildup to that and how that was and why that was in the book. Obviously, I am still feeling it. I tend to feel things and understand things logically about a year after they’ve happened, especially when it’s good and I think that’s okay.

I think that’s a good thing that my mind does because it allows me not to get too caught up in things that are too terrible, and also does it have me feeling and believing all the hype. I’m just doing the work and I have been doing that since day one. I did it before anybody knew my name. I did it when I had no money. I’ll continue to do it no matter what happens next. It is what drives me. I don’t know anything better than actually executing on the work.

Brian Ardinger: So, we are experimenting with this Inside Outside podcast. Today’s our first live event. We have a number of people in the attendee’s things. If anybody from the audience has a question, you can go into the Q & A and then type it in there, and we’ll have Arlan have a chance to answer that as well. So, we wanted to make this engaging as much as possible. A couple questions as people throw in their questions. How can our community of innovators, we have an audience of corporate innovators, entrepreneurs, investors that pay attention to this, how can we become more focused and adaptive to both identifying and fostering underestimated founders in our own communities?

Arlan Hamilton: Yeah, I think it’s more about, to be honest and frank, I think it’s more about identifying rather than fostering. I mean what I found, and I’ve been to hundreds and hundreds of events across the country. I’ve been to almost every city I can think of. Still more to go though, when this is over. And what I’ve found is that they’re there. When I go to these events, usually I’m paid to come speak. I am treated very well, and it is very earnest from the host, very earnest we want you to speak.

But what I find when I get there is that the haves, the people have the capital, the resources, the people who are working in corporations, from the government, policy makers, angel investors, fund managers. There is a complete disconnect from the founders of color or women or LGBTQ, et cetera, who already exists within their ecosystems, but they simply either are willfully ignoring or are just missing out on. And they’re there.

And that’s what gets me because I’m like, oftentimes there’ll be a bridge to them. The founders will pull me to the side. They know they can talk to me very candidly. And they’ll say, we’ve tried to get a meeting here. We’ve tried to do this, we’ve done this, and that. They’re just not taking us seriously. And it could be that the people who are in those positions. They don’t know how to recognize it. They don’t understand the value that they’re looking right through. On paper it may seem more philanthropic to them or something less than to them, simply because they’re used to something else being the status quo. That’s simply the point. It starts with like awareness is straight up being in the room wanting to change.

I always say, when I do speak at these events, I look around to the white men who are there. I say to them, the fact that you’re in the room, it’s like, you got my vote. You know what I mean? Like we’re cool because you’re here. A lot of people wouldn’t be here.  I said awareness first, and then it’s like not feeling like you are the savior, the White Knight, so to speak. It’s saying what am I, as this person with some sort of means, what am I missing out on? Where is your competitive spirit? Where’s that competitive nature that I know you have, that curiosity I know you have to dig deeper.

And usually in most of these cities I’ve been to big and small, there are founders, and there are usually people who are founders and also hosts of things and key makers, as we call them, and collaborators, who have been doing the footwork for years. I don’t think it’s about reinventing the wheel or having to figure out how to completely change the way you act. I think it’s simply opening your eye, going to the first layer of who can I reach out to, but I can just simply ask what they need and how I can be helpful and how that may, if I’m lucky, bring me return.

Brian Ardinger: Flipping the coin, as far as like what do you look for when you start talking to founders? You know, you mentioned curiosity and that grit and that, but what other characteristics make you sit up and take notice when you’re talking to a founder?

Arlan Hamilton: Yeah. I’m always looking for, I’m pattern matching. Well, just like any other investor, I’m looking for someone who feel like they’re made for what they’re building or what they’re running. This, this founder fit that I like. That is just…you feel it. I do at least, and it just makes sense to what they’re doing, and it is part of pattern matching and I don’t think there’s anything wrong with that. I just think that the people who had been pattern matching for so long, we’re very homogenous.

So, I’m pattern matching. I’m also looking for someone that reminds me of myself in that they are, I call it hungry, not thirsty. They have a very specific level to them of what they are willing to do for their company, what their ideals are, what their abilities are, and they won’t cross the line. And there is a professionalism there and there’s this, but there’s also a creativity.  I look for all of those things in a person. I think there’s a question, actually. Should I read it? Are we?

Brian Ardinger: Yeah, go ahead.

Arlan Hamilton: Jennifer says, beyond just being more aware, what are you telling the money folks? VCs, Funders. That they need to do to widen their pipeline to include companies outside their traditional investment lens. I said it starts with being aware. I don’t consider myself a diversity expert, especially in the corporate world. There are a lot of those who exist, but it starts with awareness. Then it goes to a curiosity and an openness. And he willingness to be a little uncomfortable. You can be uncomfortable for a day or for a week, knowing that the people that you’re looking to find may have been uncomfortable their whole life, or their whole professional career, like opening that up a little bit more.

And I try to be really realistic and I think that helps me too, because I’m sitting in these rooms time after time, after time or on these phone calls or in these meetings. I’m trying to put myself in the shoes of the guy. Usually it’s the guy. Who has that kind of role and that kind of power and that those resources or a perceived power in some cases? And trying to think what is an incentive for that dude to get outside of the box? You know, there’s a Pollyanna way of thinking about it and talking about it and like we all should get along.

There’s also this realistic way of like what part of his agenda could we open up. It’s about humanity and talking to the person one by one and figuring out what is helpful to them and their circumstances. It’s also really important to understand that black people, brown people, women, people who consider themselves underestimated, as I call them in my book, they’re not going to sit around forever and wait for somebody come by and get them and understand them and save them. Very few have I seen sit around and wait.

They won’t even wait for the few months that it takes me to raise money to put in my money. Well, they’re certainly not going to wait around for the person who didn’t believe in them to get it. You’re going to be left behind. I’ve been kind of waving my arms for the past nine years saying this, but it’s true. You’re going to be left behind. It’s already starting to happen. If it were me, I’d rather be on the side of, of getting the upside.

Brian Ardinger: You mentioned the pattern magic. Is there a different type of pattern that you see versus what the traditional pattern, obviously you hear about venture capital folks in the Valley and they’re matching to Stanford, white guys and that, but what other patterns do you look for that may be different?

Arlan Hamilton: Well, a few things. I mean, it runs the gamut. Things that I relate to, so I relate to, for instance, overachieving quote unquote women of color. Women who have been giving the guys the answers for a long time. Whether it be them writing over their reports or you know, their tests or not. I didn’t personally go to a great college, but I was accepted into some and was on that path, were it not for resources, but people who are considered gifted and are in those colleges and don’t quite understand how much of a microaggression they had to deal with on a day to day basis in most cases to get into the college, to get through the four plus years in that college. So those types of things.

That woman who walks into the room, who has a company would normally have to spend at least 30 minutes explaining to the traditional quote unquote funder is now able to just be themselves with me and just start by telling me about their company. There’s also another one again, as not directly matching, because I’ve never had a child, but I tend to have a bias towards any person, man or woman or other who is either holding a child, nursing a child, dealing with two children in the background, while they’re talking to me about their company. Because when I look at that, what I see is someone who can multitask, who can lead, who has a lot of drive.

And where that may be like a traditional, again, quote unquote investor running for the hill or asking very uncomfortable questions about their abilities, because they have a child in front of them. At one point about four years ago, I was meeting back to back with women who were pregnant, who were hiding their pregnancy while they’re on the funding, and I couldn’t, I say I couldn’t believe it, but I could believe it.

But it was just shocking that they would think they would have, did hide something that is not a bad thing. You know, to be shamed into hiding something that they felt would hurt their chances of raising money for their company while they’re producing life. Just by the way, I’ve seen about 20 live births happen, because I used to be a production assistant for a TV show that was called One Born Every Minute.  In a two-month period, I watched 20 live births happen with 30 cameras. I have so much respect for women. I like I have respect for every person. But I have so much respect for people given birth because I’ve seen it and I’m like, how are you? What’s going on? Oh, how is that possible?

There’re just different patterns that remind me, either of myself or the women, or the people I grew up with, grew up around. Forty-year-old black woman is to me, an expert in most things. And I say that now. I used to say that as a 30-year-old, but now 40 or 50-year-old black woman. That’s what I remember my mom being. Whereas it could be seen as, Oh, that must be someone’s secretary. Or that’s someone’s head of people – HR. That’s a CEO to me.

Brian Ardinger: I think we might have time for one more question from the audience if somebody wants to type in an audience question. The last question I’ll ask is, what are you most hopeful for going into this world of disruption, what are some of the positive things that you’re looking forward to in the next six to nine months?

Arlan Hamilton: I don’t think that everybody has to jump up and be everything to everyone right now, but I am looking forward to the innovation that comes from this. I’m looking forward to what will be the new norm, the new creativity that comes from this. I’m also looking forward to the creative ways and sustainable ways that people figure out to take care of themselves. And in an even better way now, because we’re having to figure that out immediately and right acutely as a species right now. And so, I am not only looking forward to like what new innovations and what new apps and products and this and that come out, but ways that we treat ourselves and treat each other. I think we’ll be interesting.

Brian Ardinger: That’s amazing. And you’ve got some interesting portfolio companies already so I’m excited to see where that goes. One more question from the audience. Lillian asks, thank you Arlan for being outspoken about this. As a black female founder, I totally understand and feel all of the pain points you mentioned. A lot of people don’t take us seriously. I try not to flip and stay calm. Any thoughts on the mental game or mental toughness for black founders who are currently experiencing this?

Arlan Hamilton: Oh yeah. I mean, imagine if you’re not in that position. Every single day of your life. Someone gaslights me. Yeah. Someone trying to make you think you are crazy or imagining. I call it paper cuts, the microaggressions. I call them paper because when you get a paper cut, you don’t run around and say, Hey, look, I got a paper cut on my finger. You know, it’s not the same as slamming your hand in the door or something bigger. But paper cuts hurt like hell.

If you have that happen to you every day, it’s torture. And we are not as humans, we’re not meant to constantly, always be on guard and constantly always be in trauma and mode. Right?  But black people do and are always. And the biggest insult to that injury is in people not believing or thinking we’re overreacting or that we’re aggressive or we’re this or we’re that.

For me, I, I try to use humor. Humor helps me. It’s saved my life, has helped me through things. Just like music has, the arts. Yeah. I try to use humor though to diffuse what can become a tough situation. Doesn’t always work though. Sometimes I do flip. I don’t ever physically flip, but you’ll see me on Twitter cussing someone out because I’m grown, and I can. Also, because sometimes, I deserve it. And I think there’s that fuse. You have to let that steam out every once in a while. You have to. I said, so I think if you can let the steam out on your own terms, on your own schedule by maybe blogging, by having a podcast. That’s why I have a podcast, so I can say my piece without anybody editing me. I’m saying what I need to say.

And have that vent that just helps you out every once in a while. I think that’s the way you do it. And then ultimately, if you have routine your group, play It squad. That you can vent to privately. Maybe it’s every month. You all get on Zoom, you know, together 6-10 of you, you get on Zoom. I think those things help so much too.

Brian Ardinger: Arlan, I know you’ve given us more time than actually we allotted. I appreciate you so much for coming on Inside Outside Innovation. If people want to find out more about yourself or get in contact with you about the book. Yeah. What’s the best way to do that?

Arlan Hamilton: If you go to, Itsaboutdamntime.com you can pick up the book, you can pick up the hardcover, the audio version, eBook. I know there are different ways people are trying to get books these days, but there’s a way to get it. And you can reach me online. Twitter, Instagram. I spend a lot of time on both platforms. I really enjoy connecting with people – ArlanWasHere, on both platforms.

Brian Ardinger: Arlan, thank you so much for being on Inside Outside innovation. Hope to have you back sometime in the future to talk about all the new things that are happening, and I really do appreciate you coming on here and being our first IO Live guest.

Arlan Hamilton: Yeah, it was a lot of fun. Thanks for having me.

Brian Ardinger: That’s it for another episode of Inside Outside Innovation. If you want to learn more about our team, our content, our services, check out InsideOutside.io or follow us on Twitter @theIOpodcast or @Ardinger. Until next time, go out and innovate.


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Episode 198

Ep. 198 – Arlan Hamilton...