Arlan Hamilton: From Homeless to Venture Capitalist

Hey yeniverse!

It’s been a crazy week so I took a break and decided to catch up on a few podcasts that I’ve been backlogged for too long (and you know what I’m talking about…!) and one of them was via Justin Kan’s new podcast, The Quest, with Arlan Hamilton who we recently mentioned in a recent deep-dive!

My notes might be a bit different in type and tone, but, I tried to pull out many of the thoughtful and insightful things that Arlan shared, especially if aligned with the more fundamental values of building relationships and communities.

Arlan’s story is touching and powerful; you really should listen to it if you can spare the ~80 minutes โ€” worth every second.

To infinity & community,

โ€” john


From the show notes:

Arlan Hamilton, the founder of Backstage Capital, a VC firm focused on backing underrepresented minority founders, and one of the most determined people Iโ€™ve ever met.

Five years ago, knowing nothing about the technology industry she set out to become a VC no matter what โ€” even spending time homeless and living out of the SF airport to make it happen.

We talk about her new book, resilience and determination, what sheโ€™s learned from being an investor in over 150 companies, overcoming alcohol addiction, and more.

Let’s jump in.


How Did You Get To Become the Manager of Norwegian pop-punk band “goldenboy”?

Part of Arlan’s process that she shares was simply taking chances and learning new things, as she continues to experience new things.

It’s crazy-simple in both attitude and approach, but, for many entrepreneurs, this is how we begin: Experimenting with things that we were interested and following where those interests wherever they may lead.

For Arlan, she knew that the music scene (especially the “behind the scenes”) was where she wanted to be โ€” I even found a 7+ year-old interview with her:

When I was 13, I went to my first concert. It was Janet Jackson and it changed my life. I had a lawn ticket but was handed a front row ticket by a crew member. I remember looking back at thousands of people of all races, ages, and backgrounds singing along to every word.

It was the most amazing thing Iโ€™d ever seen and I made a decision that night to find a way to be part of whatever THAT was for the rest of my life. I didnโ€™t know at the time that it would lead to working on tours, but ultimately it did.

She continued to follow this path, growing in the size and scope of the live events, eventually scoring gigs with some of the biggest stars:

She shares much, much more about the path, of course. But, the story behind becoming the manager was that she simply loved their music, hustled to bring them stateside, and earned the right to serve them.

She still does this, by the way โ€” it’s built-in to who she is.

What about losing the Magazine Startup?

After working in the highly-produced events, like Warped Tour, she wanted to start a magazine that featured artists that she and her brother would love. It would also be a “luxury” version of magazines that used quality materials (which wasn’t the norm at the time).

She started building community in and around the print magazine by not only getting deep-dive interviews with artists but also creating a safe space to talk about the more difficult topics, like drug abuse (and recovery).

This created lasting resilience for her, despite how hard the 5 years were:

I do not let current “failures” get to me โ€” I understand when you pull back the lens, what hindsight really is. It’s not all perfect. Everyone’s going through something.

Arlan Hamilton

Justin shares his own thoughts about how he’s struggled in difficult times and how internalizing failure can totally wreck you. Startup success isn’t mostly outside of our control โ€” preach.

For all of us who are building new projects, new businesses, new communities… keep going! Our community of yenizens know what this is like; it’s worth the hardship and you’re not alone!

How did you get into VC?

Arlan’s strategy was simple: Start doing research and outreach, asking questions, engaging with folks, and making herself available.

And, instead of going to folks who already have the money and power, she went to folks who didn’t, the folks who are under-served and under-represented. She started with a simple plan of raising $1.0M โ€” then, she increased the size and continued to execute against her simple strategy of connecting with her growing community while serving them well.

She had some really tough lessons, as we all do, she shares an experience of having to say “No” to the money, despite her need for it (really bad relationships and shitty behavior).

In terms of her first fund, she had been working on it for 3+ years before she got into a Stanford course, a two-week bootcamp, and Chris Sacca was one of the first folks to contribute to her crowdfund campaign.

During that course, she met her first investor and she was able to stretch the first two tranches of $25k each and make it count. The introductions continued to come as she continued to perform and pinch pennies.

The results have been telling as she shares that the trust she’s developed through her relationships have created a growing deal-flow pipeline, maximizing what she’s amazing at providing:

  1. Capital
  2. Confidence
  3. Connections

She continued to work on her craft, refine her pitch, narrow her value propositions and value differentiators, to become a “brand” that could help elevate and “go before” one of her investments, a’la Andreessen or YCombinator and other top-tier venture firms.

What have you learned from sourcing under-estimated founders?

I love Arlan here:

People who are under-estimated do not wait around to be “saved” โ€” they think about not letting their competition get away and I’ve seen folks leap-frog incumbents because they aren’t going to wait around for the “funds” to deem them worthy.

There’s a lot going on behind the scenes and it’s Arlan’s goal to reveal and support these folks. I think that’s also a similar mission that we all have as community leaders and builders, highlighting what needs to be given more light in our broader relationships and communities.

There’s much, much more in this podcast and my notes and reflections can’t replace how Arlan articulates her own story, even about becoming sober and alcohol addiction (!!!) as well as a few notes on being homeless; what I love, though, is that she redirects this attention to not just about her journey but also what is possible for others as well (and the long way that we all have to go for equality and access in venture capital and entrepreneurship.

I’ll end my notes with a final, positive quote from Arlan:

Life is so short and we’re so fortunate to be alive during this time and to have the access that we have.

Amen and amen.

Oh, and of course, her book:

Have a good one folks.

%d bloggers like this: