The improbable rise of America’s hottest VC

Arlan Hamilton is changing the face of Silicon Valley, whether you like it or not.
Arlan Hamilton is changing the face of Silicon Valley, whether you like it or not.
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In the tale we’re sold of Silicon Valley, meritocracy flourishes. Those who grind the hardest, hone the best ideas, and make the most connections become billionaires. Class, race, and gender melt away, and those who deserve success seize it.

Some see Arlan Hamilton as proof that this romance is reality.

As of 2015, Hamilton was broke, homeless, and sleeping on the floor of the San Francisco International Airport. By day, she pitched investors across the Bay Area. Her dream: To change the face of Silicon Valley by creating a venture capital fund that invests in “underestimated” founders.

Despite having no college degree, no formal investment training, no industry connections, and being a black, queer woman, Hamilton has materialized her vision. Today, she’s the founder and CEO of Backstage Capital, a seed-stage investment fund that’s invested in 80 companies, all of which have at least one founder who is a woman, person of color, or LGBTQ. Backstage’s portfolio spans various industries and companies based across the nation, from tech-enhanced fashion and jewelry to virtual augmented reality, distributed energy management, and pleasure education. She’s a sought-after speaker, hosts her own podcast, and is the subject of Gimlet Media’s newest season of “Startup.” Backstage Capital’s general fund manages over $5 million, and, as Hamilton announced, is launching a $36 million fund that invests only in black female founders, $1 million at a time. “They’re calling it a ‘diversity fund,’” Hamilton tweeted. “I’m calling it an IT’S ABOUT DAMN TIME fund.” In 2017, women founders received just 2.7% of VC funds and from 2012-2014 women of color just 0.2%.

Hamilton quite literally made it from the bottom, but she’ll call bullshit on anyone who says her journey epitomizes meritocracy. I spoke with her on April 24 at a Quartz event in San Francisco. She describes her unexpected rise from being self-taught and without connections to where she is today.

When Hamilton began learning about Silicon Valley around 2012, she had $12 in the bank, was in her thirties, and lived in an apartment with her mom. She left a successful career in the music industry, working as production coordinator and tour manager, to pursue venture capital, a career she knew nothing about—inspired by music managers like Troy Carter, Lady Gaga’s manager, who was an early investor in Uber. 

“I have a blowup bed, and a white board with ‘venture capitalist’ written on it. How do I go from this to putting money into a company?” she asked herself. “To become a VC, most people go through four years of school, or get an MBA. I thought, I can figure that out. So I just did that at home.”

To begin, she learned as much as possible, as quickly as possible, spending countless hours online.

“Everything you need is on the internet if you have the willpower to find it.” She watched VC videos and interviews on YouTube and Vimeo. She also took online VC classes, including one class taught by early-stage investor and entrepreneur Brad Feld. “In Brad’s videos, it’s mostly white dudes in the class, but I was right there with them,” she recalled, smiling. “I stuck with it, and I read a ton of books, all written by white men—which I’m going to change soon.”

Beyond self-educating, Hamilton reached out to countless tech startups, asking to help on any project. 

“Anytime I saw a video or read something that I thought was interesting, I would just find a way to get in touch with them,” she says. “I saw Jason Calacanis talking to Chris Sacca online, and I got in touch with both of them. I saw Brad Feld talk a lot, and I read his books, so I got in touch with him. Sometimes it was just finding an email or a phone number, and sometimes it was being really clever on LinkedIn.”

Hamilton spent hours reading about Sam Altman, the 32-year-old president of Y Combinator, arguably the most successful startup incubator in the world and angel investor who has backed Airbnb, Reddit, Stripe, Pinterest, and more.

Aware she couldn’t easily wrangle Altman, she decided to figure out who “his people” were.

“So I found this dude named Jack on LinkedIn—I don’t know anyone named Jack who’s an asshole—and I reached out to Jack, and I said ‘Hey Jack, I’m this girl you’ve never heard of, and I’m in Paralant, Texas. Can I talk to your brother?'”

Jack is Jack Altman, Sam’s brother, who is now CEO and co-founder of Lattice, a performance management platform. The sibling stalk, Hamilton clarified, is not cool. Don’t try this at home. ”I promise you that $39.99 LinkedIn Premium monthly fee is worth it. But it was so hard to get. I was broke, you know … but I figured out the $40,” she said. 

Soon after, Jack replied saying she couldn’t talk to his brother. But Hamilton persisted: “Cool, will you look at my deck and give me some feedback?”

“I thought I’d never hear from him again,” Hamilton recalled. “But he looked at my deck, and he wrote me back, and was like ‘Sam’s got to see this.’ So he sent it to him, and I was on the phone with Sam a couple days later.”

Audacity pays off, if you’re willing to implement it at scale: For every yes, Hamilton received hundreds of rejections. By summer 2015, she’d left Texas and moved to San Francisco, where, having become completely broke, she slept on the San Francisco International Airport floor by night, and pitched Silicon Valley investors by day. She avoided dejection, however, by reminding herself that every cold email or phone call is just another opportunity to refine her pitch. It’s a skill she honed as a child, going door-to-door as a Jehovah’s Witness—a pursuit defined by near constant rejection.

“I did a lot of asking important people, can I be your apprentice? How can I help you? Can I get you coffee? Can I answer the phones?” she explains (admitting she didn’t know how to make coffee, but would learn). She went on:

“A lot of this was not me sitting across the table from VCs, because they wouldn’t give me the time of day. A lot of it was me walking side-by-side with them as they walked out of something, or away from something, or away from me. I don’t think there’s any room that any of us do not deserve to be in. And I certainly thought that for myself. So I didn’t have a problem walking up to someone and talking to them about my ideas.”

Ruthless as Hamilton’s self-confidence seems, her journey is laden with far more lows than the vast majority of entrepreneurs face. As Aimee Growth explains in Quartz, entrepreneurs don’t share a special gene for risk—most come from extremely wealthy families. “The average cost to launch a startup is around $30,000, according to the Kauffman Foundation,” she writes. “Data from the Global Entrepreneurship Monitor show that more than 80% of funding for new businesses comes from personal savings and friends and family.” The comparatively insurmountable doubt, bias, and belittling Hamilton faced—without any personal savings or family and friend investment—is why her journey does not define meritocracy:

“If you know anything about my story, think about the extremes we’re talking about: four years ago, on food stamps; three years ago, sleeping on the floor of the airport while trying to raise. Do I have to be that extreme to have any sort of success here?” 

“Is that what you’re saying? Because that is not okay. That’s very fraught. I would say my success—I don’t feel successful yet—but the journey to it has to do the fact that I see a few years into the future, and I walk towards that path, and I can’t stop. It’s a dogged determination, it’s a resilience that I can’t explain to you why I have it, but I can go through the 99 no’s and one yes, and get back up.”

Hamilton’s resilience doesn’t mean she’s impenetrable. “I cried on the floor a lot, that happened a lot,” she admits. ”I was sad a lot, and I was lonely a lot, but it was like, okay I gotta get back up, here we go.”

Ultimately, Hamilton knew her idea was good, and refused to let go of it. Today, she looks for the same relentless persistence when choosing which entrepreneurs to fund. “I look for founders that remind me of myself,” she said. “Would they have done what I did to get here?” She wants founders who are solving personal pain points, not flipping companies; who want to endure the endless thrills and disappointments, financial spikes and blows necessary to build their dream.

“I’ve always been inspired by a rap lyric that says ‘I came for the cake, not the crumbs,'” Hamilton said. “But my drive comes from the hundreds of people who have said, ‘Oh what you’re doing is so great,’ then turned their back on me. From people not taking the call, or not noticing me, and somehow thinking that I’m there for the little scraps they’ve deemed acceptable to throw at me.”

“Nuh uh,” she concluded. “That’s just not interesting to me at all. I wake up every day and say, how do we grow, how do we get better. This might make me sound like a jerk, but when I hear stories about all these guys who are supposed to be these geniuses in Silicon Valley, I’m just like, ‘well, I could do that. I could definitely do that. Let’s go.'”

This story is part of How We’ll Win, a project exploring the fight for gender equality at work. Read more stories here.