“Privilege is also like underrepresented. It's kind of turned into negative. Privilege is a thing that you have. Everybody has some privilege in some way. I mean it's just a fact.” Arlan Hamilton CEO, Backstage Capital

ROB: Welcome to Disruption Now. I’m your host and moderator, Rob Richardson. It's an honor to have Arlan Hamilton on the show. She's moving fast but she's had a long way to get here though. From the outside looking in, it looks like it's been a fast success but as you're going to hear, it really hasn't been. It's been a struggle but she's grown and learned every part of the process.

She has built a venture capital fund to invest in. And I like the way she says this -- “Underestimated founders.” I think, sometimes, when people say…
ARLAN: “Underrepresented.”
ROB: …“Underinvested, Marginalized,” those are terms that people sometimes align with “not worthy of investment.” -- So I like the way you say “Underestimated” because I think that's the right way to say it.

She has her own podcast, “Your First Million.” And of course, we're here a lot to talk about her book, “It's About Damn Time” because literally, it's about damn time to have real equity. That's what we talk about on this show -- “Black equity, black and brown equity, equity for everyone.” But we know that's not where we are now. But Arlan Hamilton has been working with her own venture capital fund, “Backstage Capital,” to change that.

We're going to learn about her journey, her struggle, and how she's gotten to this point. -- Arlan, welcome to the show.
ARLAN: Thanks so much for having me.
ROB: Well thanks for coming on. You know, as I read into your story… I read your whole book and I recommend everybody to get the book. It's a great book. You do a great job in telling your personal narrative and how you got here. And you're just extremely, I think, vulnerable, humble about your experience and I think a lot of people will relate to it once they read the story like I did.

We have a lot of things in common. Just very quickly, you absorb knowledge the same way I do. I have read books. I've done that before but I love Audible. So I get up and I listen to so much Audible while I take notes. So we have that in common.

Also, I know your brother has a learning disability. I do, too -- ADHD. And you'll appreciate this story as I… It'll be one of my first questions. The reason I started Disruption Now is about empowering people to not be stuck in these narratives that people say we have to be stuck in. It's about disrupting those, what I say, “common narratives” as constructs.

I was told in school I was never going to go to college. I was in learning disability classes and those remedial classes until about eighth grade. And then the light bulb went off. I said, “Okay, I know I can do more. I want to do more.”

And my teachers and counselors gave me their motivation of a speech. They said, “Look Rob, you've struggled with school. You're not going to college. It’s not meant for you.” I’m like, “Okay.” I’m like literally in tears at this moment. Luckily, I have a strong black woman who is my mother who said, “Look, you don't have to accept any of that. You define yourself for yourself by yourself.”
ARLAN: Absolutely.
ROB: I want to tell you that your story, your brother's story really spoke to me. I didn't have the same level of struggle in terms of economics but I do understand what it's like to be underestimated, to be told you can't do something; for someone to put you in this box and how deflating that can be in that moment and how you have to really learn how to reject the narrative and really create your own. So I just want to let you know that your book spoke to me in that way. It really helped me and so I want you to do what you've done best -- you help others.

I want you to think about your younger self at whatever point. It could be pre-Backstage Capital. You had a really interesting experience on the road when you were just getting into, really, the music scene. Let's get your younger self at one of your critical pivotal moments. Knowing everything you know now, what advice would you give your younger self and what advice would you ignore?
ARLAN: I would say ignoring anyone, including myself, who would say that they know what my path is going to be or that there is a certain age that you have to… you know, once you get to that age, there's no future for you. None of that is good advice.

Some advice I would take, I would tell my younger self to be better. This is kind of boring but it's true so it'll be helpful to people -- to be better at keeping track of the conversations that you have, so your CRM.
I talked about in the book, I reached out to a hundred people when I wanted to get my touring gig, and a hundred tour managers and production managers. And I also did something similar in venture. So I go into it in the book and you can read about it there.

But I needed to have kept better notes of the first conversations that I had and how I kept up with them. If I had that today, all of that data would be really helpful to me today because it becomes dozens and then maybe hundreds and maybe even more than that. For me, it's thousands of people. And I think you can kind of treat it like… You know, you treat your networking a little bit.

And I know some people who do this, actually, who are really good at this early on because you don't necessarily know why you may need that certain connection or to know that one person who does this one thing. And you don't want to do it too mechanically. You don't want it to make it such a transactional experience.
ROB: Sure.
ARLAN: It is good to go back and say, “Seven years ago, I remember kind of ambiguously, that person would be perfect to talk to right now about this topic.”
ROB: Yeah. You talked about that a lot in your book. Again, I want people to read it. And I also want to get into at least some of what you were saying in your book.

I remember you had a goal that you wanted to meet -- I believe 10,000 people -- and have an intentional conversation. Although you didn't keep that data like you wanted to, to the level that you would have wanted, I would say you're far above most people because you went out with the goal of getting to know people.

Tell people about your process and really wanting to know and understand where people are coming from. You hinted at it but I want you to get more into it. It wasn't transactional in your approach but it was intentionally in your approach which sometimes led to greater results. Can you comment about that?
ARLAN: Yes. The original idea though was that it would be pretty fast because I knew 10,000 people was a lot of people. So originally, this was probably, I would say, 15 years ago, something to that effect, where it started.

So mid-20s, I had a music magazine -- and this was before I was able to get it off the ground -- and I needed to raise $10,000 in order to launch this magazine. This was what I needed at that time.
So I had originally this idea: If I meet 10,000 people over, let's say, three months that I thought I could do this in, I’ll take a picture with each person… And I seriously go pretty fast. I just get their name. And I put that picture of them every night on a website. They go to that website because they have the URL and then I sell a t-shirt. And if I could sell a 10th of that -- I did all the math -- maybe I’ll get that $10,000.

So it was a lot of jumping through hoops and mental acrobatics. But I thought that would be the case and it would be interesting.

First day, I go out which was in Houston, Texas -- it was the first day -- I ended up meeting 30 people. I was trying to meet 300 people a day. I ended up meeting 30 people. And the reason I met 30 people is because--

Starting with the very first person -- I remember clear as day -- she was a girl at a coffee shop. Starting with the very first person who I got the nerve to go up and talk to, once I told her what I was doing… And she wasn't weirded out by it. It was a conversation. I got to know her. I got to understand her.

Then I went to the next place and I said, “Okay, I got to go a little bit faster than this so I’m going to go in a group. I’m going to talk to a group and get them all to kind of do this.” Well don't you know, each person in that group had something to say. Because we all are individuals, we all have something that we want to say.

So this 10,000 people, quick vibe in three months, turned into… I got to about 500 people in about a two-year period. And I still one day will do it again especially when we have Covid in the far rear view mirror.
ROB: Yeah. I am curious to see… You are an introvert. You admit to being an introvert yet you have to do a lot of things that are “extroverted.” You have to step out, really, in a zone that you're not very comfortable with -- I think that's pretty safe to say -- speaking in front of a lot of people, doing things like this. These are things that people consider “extroverted” type of things.

But you talked about overcoming your insecurity with information. Can you walk people through that because I think there's a lot of people right now that are like yourself, right? They're introverted, thinking that, “Okay, for me to do this, I have to go out there. I have to speak in front of people. That's not what I’m good at. That's not something I can do.”

Advise those folks, if you can, about how you go about it. I know it's different for everybody but I think hearing someone like yourself who is not a person who wants to just say naturally, “I’m going to get up and speak in front of 10,000,” that's not your default go-to but yet you've been very successful in doing that.
ARLAN: Yeah. So today, I can do that but up until I was 36, up until March of 2017, I had terrible stage fright -- and I mean “Terrible.”

One time, I was invited and hired to be a host at a Pride event in Colorado Springs and I hid behind a tree because I was so scared. I was so bad.

Any time I had anything in school that I had to do public speaking, I would skip that day and say I was sick. I was just terrified. I think 50% of the population apparently has stage fright.

When I got into what I do now with Backstage Capital and making these investments and being more front-facing, I made a decision. I said, “I’m going to be quiet. I'll talk online all day but I’m not going to go out in front of people.”

And a couple of things happened at the end of 2016 that changed my mind. One thing was I was given an award. And in order to receive the award in person -- there's this big gala -- I had to give a 5-minute “Thank You” speech. I couldn't do it so I had to turn down the award.

I went to the event with my mother who flew in to California for it, just to be my sidekick there, and I had to watch somebody else get the award. And I was like, “Man, that could have been me and I could have made my mom so proud.” And so that got me thinking.

And then I had an opportunity to speak at an event that Richard Branson was going to be speaking at right after me if I was to take it. I originally said “Yes” but then I got so nervous, I had to cancel it.

I went to that event and I watched as the person who was taking my spot walked off stage to where Richard Branson was, and he had been an entrepreneurial hero of mine since I was 13 years old.

Those two things happened within a month of each other. I said, “Look, I got to figure something out if I want to go to the next level here. I can't be stuck in this cocoon. I have to figure it out.”

So 2017, at the top of the year, I said, “I will say “Yes” to three speaking events, big and small, this year and I will do them no matter what, even if I’m scared. At the end of it, if it doesn't work out, at least I can say I tried. And maybe it'll work out.”

A few things have helped me. And I’ll say this as to kind of wrap it up, to put a bow on it. Today, I've spoken at, at least, 300 events. I have Headline events. I have Keynote events. I’ve spoken in front of 20,000 people in person a couple of times and I don't have that same fear. I’m definitely introverted still. Those are maybe two different things but I don't have that same fear.

A few things helped. One thing was realizing that it wasn't about me. That was really helpful because once I realized, “Wait a second. It's not about me and “What if I fail or what if I fall off the stage or say something stupid…” because that's what I was worried about. It's about the people who came to see you and the people who maybe didn't come to see you but are listening and they hear that and they're in the back of the room and they're just taking that in and something clicks for them. And because I want that in my life, I was like, “I got to do it just for that alone.” And the more I did it, the better it was.

People talked about that. They said, “You know, you just got to try it and then it'll get better” and I was like, “Yeah, right.”

One big piece of advice I will say… and there's a lot more I go into in the book about it. But one thing I will say is, “Don't let anybody tell you that it's your time to speak” if you have stage fright. Don't let anybody force you into doing it because that's not necessarily going to be fruitful.

But have a personal conversation with yourself on your own time, in your own space, and start mapping out maybe a plan of, “This is when I want to try to give it a shot.” And what helped me so much is to say, “Even if--”

My biggest fear is -- I had to break that down -- where I would say something wrong or stupid and it would be forever there or even worse, maybe--
ROB: Yeah, the imposter syndrome thing.
ARLAN: Yeah. And another thing I thought was, “What if I get so scared that I can't speak” -- so I’m on the stage and I can't speak and it's just dead air and I have to leave. So what I did was I said, “That can be okay.”

So the first one you do, you don't do it in front of 20,000 people. You do it in front of 60 like I did. And you say to the host, “I may not make it through this conversation because I have such bad stage fright” and they’ll have a B plan. And you inch your way towards normality where it does feel normal to you. And I promise you, at least half of you who feel this way right now -- at least half of you -- will not only be good at it and be able to do it, you will enjoy it and crave it.
ROB: Yeah. That's great advice.

So you had a very diverse background, to say the least. You grew up a Jehovah’s Witness. And I know that you don't believe in a lot of things Jehovah stand for now but you grew up that way. And you talked about a little bit being in that experience, being LGBT, being a black woman -- all those things together played a role as an outsider -- and being underestimated and looked at differently, having to go door-to-door and having a bunch of people say “No.” Can you talk about that experience, how that experience of your background, in general, led to your current success now because--

I’m sure a lot of people do know this but you were homeless for a period of time right before you started Backstage Capital which is quite amazing. My guess is your experience, not only as a Jehovah Witness growing up and taking “No” all the time, being an outsider, but also your experience with the music industry probably prepared you for what you needed to give you that certain level of preparation.
ARLAN: Yeah. I was separated, too.
ROB: Okay, separate too from?
ARLAN: The differences being a Witness. I have very strong opinions about it. And to me, it's giving credit to an abuser for making you tougher.
ROB: Oh, all right.
ARLAN: I think it's a cult and I think it was very damaging. It did, of course, put me in a situation where I had to hear “No” a lot.

A lot of times, people will say, “Well wasn't that good that you had to hear “No” a lot and that built up your defense of that?” You probably could argue that but it did more damage than it did good.
ROB: Right. So there's better ways to do that. Got it.
ARLAN: Yeah, I try to separate it. But being in the music industry--
ROB: Yeah, let's talk about that.
ARLAN: The music industry, for sure… And you can air all of this. The music industry was great preparation especially with the work I was doing. I was in the live music touring so I was on the road with these people which is different than going into an office or going into a recording studio. You kind of see the good, the bad and the ugly.
I was surrounded by people with all kinds of personalities, all kinds of agendas, all kinds of talents, all kinds of dreams and faults and all sorts of things that were just like a boot camp. And doing all of this while on the road, while it being… You know, the job, it was like a boot camp in learning about human behavior, learning how to treat people, learning about hierarchy.

A lot of times, the artists were the least of my troubles, like the least maintenance there was and it was somebody who just thought that the whole thing was about them. They could gum up the works and that was who… you know, the squeaky wheel. And then sometimes it wasn't the case. Sometimes, it was the artist that I needed to think about -- ego and things.

So I learned how to just be nimble, how to adapt in incredible circumstances on a dime and I learned a lot about just a very exciting adrenaline-filled industry.
ROB: Yeah. And I think that when people look at your story… -- Again, for some folks who want to look from the outside in, she was homeless five years ago” or so. I believe that's right. -- And then now you're managing a huge large multi-million dollar fund. And it looks like the path was there in five years but the truth be told, certainly that period in the music industry… and even your background growing up but certainly that period within the music industry taught you a lot of skills that are directly applicable which is why you called it “Backstage Capital,” right, which is directly applicable to who you are.
ARLAN: That’s right.
ROB: So I tell folks, “Every experience that you're in…” I was in politics and what I learned is how to keep dialing. I mean you have to do it in a tactful way. But I learned how to keep engaging, figure out how to get around, make a “No” into a “Yes.” And then even if it is a “No,” figure out whether anything else can be done with this opportunity.

I remember one time, I was working on getting one person to contribute. I must have called the person 50 times. They never said “No” so I called. They never called me back but they wrote me a $12,000 check. So clearly, this works sometimes.

So you can learn from your experience and I believe your experience in the industry helped prepare you. There are many things transferable -- politics, understanding people, how to build relationships, how to build something from nothing because you have to do that when you have a tour. You don't know who's going to come to this tour. You got to figure out how to connect with people there. I believe all of that taught you.

So let people know like every experience in your life can add and help you to the moment that you're getting towards. And what I appreciated about your story is that everything you did -- from starting blogs to everything else -- helped you prepare for this moment. I think it's important for people to know that.

You talked about privilege. I want to talk about that a little bit in a different way that I haven't heard really anybody discuss “Privilege,” specifically, in this moment where we are discussing, obviously, white privilege, male privilege -- privilege, in general. But you described it as not necessarily in a negative context. Explain that a little bit.
ARLAN: Well privilege is also like underrepresented. It's kind of turned into negative. Privilege is a thing that you have. Everybody has some privilege in some way. I mean it's just a fact. It's a logical wording.

“Privilege” is not necessarily the bad word in most situations. “Entitlement” is usually the bad word in that situation. So you can be privileged because you're a guy. I can be privileged because I’m not disabled. We can be privileged because we live in a country where we are able to show our descent, at least today, without being thrown in jail.
ROB: Yeah.
ARLAN: A lot of things give us privilege even though we are black. So when someone is talking about like sharing their privilege or being accused of having it, a lot of times white people, white men, etc., will get very defensive about it. Like, “I’m not privileged. I had it tough when I was growing up.” Well yeah, you are privileged because you're a white man. When you walk down the street and I walk down the street, I’m going to be looked at as someone who may rob you and you're not necessarily in that situation.” There's different privilege.

Now you can get really defensive as a white person or as a man or this or that. You can get upset about it or you can recognize, “Okay, I do have privilege. Let's use that for our advantage. How do I get more people into this room? How do I do this” and the other.

Another way to take it though is to say, “I’m privileged so I’m going to be entitled about it. I’m owed this. I’m supposed to have this. I’m a white man. I’m supposed to be in this first class lane. Why is this black woman named “Arlan” trying to get my first class lane to get on this flight?”

And that's when entitlement comes in. And they push you to the side and you're going to say, “Wait a second. Because you're privileged, you've been treated a certain way your whole life, that has made you entitled.” So those are just two things, I think, is important to separate.
ROB: Yeah. You know, I never really fully understood how white people viewed “Privileged” until really -- and I’ll be very transparent. I’m always transparent -- is during the Me Too Movement. I don't agree now but I saw some people, they were like… Well aren't they making a general broad stroke against men saying all men have this?
ARLAN: Every men.
ROB: I was like, “That seems a little bit much.”
ARLAN: Yeah.
ROB: And then somebody said, “Well what's the difference between that and racism?” I said, “Oh.” [Laughs] And then I said, “I get that.” I mean, really, I don't know why the light bulb clicked. But how do we make that light bulb click for a white man who doesn't have any level of… they don't have to go through that level of discrimination that I have.

So I understand why white men -- and white people, in general -- have to be anti-racist. It's not enough. I told people during Martin Luther King as we observed his 92nd birthday, “Dr. King didn't die because he had a dream. He didn't die because he was articulate. He died because he challenged the status quo of white supremacy that made people uncomfortable.”

And making people uncomfortable, some people pivot towards growth and some people pivot towards defensiveness. And I guess, how do we get more people to pivot towards growth? I don't know if you have a good answer to that but feel free.
ARLAN: Yeah. With the three minutes we have, I don't know if I have the answer. But I will say that sometimes, it's not about boiling the ocean. It's not about getting everybody to understand. Maybe it's just about a handful or one or two or the people that you're involved with and then the numbers grow.

And one way is in business. That's what I am doing. I’m not spending a ton of time trying to get white men to believe that black people are valuable partners and collaborators. I’m going to say it. “If you want to jump on, I’ll show you the way. But I’m here for us and I’m here for--“

I think every white man that I’ve met has somebody that they're jealous of or that they feel inferior to. And so that’s one way of doing is making it un-personal. Some people, it's about height. Some people, it's about wealth. Some people, it's about being part of a certain group or the way that you might have been treated as a child or a teenager. And if you imagine that--

I forgot who I was talking to. It was a white man and he was saying, “I live in the same world. I have the same thing I have to worry about. I have to worry about my health. I have to worry about my family and putting food on the table.” And I said, “Yes. But when you go outside and you walk down the street to go find the food for your table, you don't also have to worry about getting shot by a police officer. You don't also have to worry about this white woman thinking that you're trying to steal her purse because you walked on a certain side of the street. And you don't have to worry about xyz.”

And now today, with Covid and everything else, you also have to worry about the doctor not treating you and your symptoms seriously because you are black.

And so that really lights up. Most white people that I know, when you talk to them logically and you give them that kind of breakdown, they get it.
ROB: Yeah.
ARLAN: They just hadn't been presented with it because they didn't have a reason to be presented with.
ROB: That’s a great story.
ARLAN: When I learned about any other culture or anything, I’m like, “Man, I’m 40 years old and I didn't know that this type of utensil was used to make that kind of food.” You feel kind of embarrassed, a little dumb about the situation so you get a little guarded. Then I’m like, “Hey, it's okay that I didn't know that. Am I supposed to know everything?” So it's okay and it's up to me to do better next time.

And that's how I think a lot of white people and men and a lot… You know, all of us can do better is to say, “Instead of getting defensive, let's think about, “It's okay for us to be wrong. Can we get right?””
ROB: Oh that's great. One final question before you leave us, Arlan. If you had a billboard Google ad that summarized your beliefs of what you stand for, what would that say and why?
ARLAN: Ooh.
ROB: I had to get one rapid fire question and then I’d love to have you back over. We’ll get some other stuff, okay?
ARLAN: Yeah. That's a tough one, too.
ROB: I have plenty of tough ones but we'll go through those next time.
ARLAN: I would say something along the lines -- I’m just saying this for the first time -- “Pay it forward and spend it now.” Kind of like, “Do it while we're here.”
ROB: “Pay it forward. Spend it now.” I love that. All right.
ARLAN: Yeah.
ROB: Hey, that's a great one.
ARLAN: Thank you.
ROB: Right off the top, that speaks to who you are. -- Arlan Hamilton, “It’s About Damn Time.” It’s been a pleasure.
ARLAN: Thank you.
ROB: We'd love to have you on again. Thank you so much.
ARLAN: Thank you.
ROB: I appreciate having you.

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