The rise of the 20-something VC

Alana Goyal opened her own VC firm three years ago. Today, she has a total of $99 million under management across three funds, and investments in more than two dozen startups. She has no partners. She works alone. And she’s only 28.

Welcome to the age of the 20-something venture capitalist.

Goyal is one of a growing number of Gen Zers and younger Millennials who are bypassing the traditional route into VC. No long years of analyst work for them. No rising to partner at an established firm, before perhaps striking out on their own at 40. Instead, thanks to shifting dynamics in the tech world, some younger investors are hanging out their shingle from jump.

These fresh-faced VCs each have a different edge. In the case of San Francisco-based Goyal, whose Basecase Capital specializes in working with technical founders to flesh out ideas for enterprise, infrastructure, and AI companies, it’s because she’s built a deep network among young techies whose lives don’t organically intersect with older VCs. “I’m quite good at finding really amazing people and building long-term relationships over time,” she says, “so that when they do [start fundraising], I’ve been there all along, and I’m the obvious first phone call.”

Alana Goyal [Photo: Courtsey of Basecase Capital]

Paige Finn Doherty, the 25-year-old founder of Behind Genius Ventures, meanwhile, taps into her Gen Z sensibilities for unique insights about what tomorrow’s workers and consumers will want. Her San Diego-based second fund just raised $8.9 million to put toward early-stage investments in gaming, wellness, fintech, and dev tools.

“Work and play will be very different, generation by generation,” says Youngrok Kim, the founding partner of the GREE LP Fund, which has invested with Behind Genius. “I really look to [Doherty] to find some new business models and companies in those spaces.”

Rex Woodbury, who brainstormed Daybreak Ventures on the eve of his 30th birthday, owes his entry into the traditionally rarified world of venture capital to the emergence of new media technologies. The name he’s built through his tech newsletter facilitates deal flow. “Content is a powerful way to build relationships at scale,” he says.

Red Woodbury [Photo: Samuel Pickart]

The fact that young people can take a leap that wouldn’t have been possible less than a decade ago also reflects how big and unwieldy the startup ecosystem has become. It’s no longer as hub-and-spoke as it once was. No firm, even the most prominent, can extend their reach into every interesting corner. And the largest are juggling so much money that it doesn’t make sense, operationally, to deal with small sums like the kinds sought at the high-risk—but also potentially high-reward—pre-seed stage. Instead, some choose to capture those returns by becoming limited partners with the savviest of the new managers.

Meanwhile, newer founders are increasingly sophisticated about the breadth of challenges that startups face as they grow. While those founders still appreciate the importance of brand-name backers, they’re willing to expand their cap tables to lock in commitment from a wide range of supporters, irrespective of their venture track records.

“Founders are seeking out the person that they want to work with,” Woodbury says. “The firm still matters, of course, but it often comes secondary to finding the person who has expertise in your domain and who you’ve built the relationship with.”

Generation Shark Tank 

Venture has traditionally been an apprenticeship business. “Younger people would work with more senior people to get a good understanding of how venture works and develop their pattern recognition for amazing founders,” says Michael Kim the founder of Cendana Capital, a fund of funds that invests in seed and pre-seed funds, including ones from Behind Genius and Comma Capital, another firm founded by 20-somethings. 

But this cohort of investors grew up on Shark Tank, Silicon Valley, Hacker News, and TechCrunch. They grasped the concept of venture capital much earlier than previous generations. Just as the movie The Social Network launched a wave of 20-something-founded startups, the tech world’s proliferation into mainstream culture is similarly luring a new generation into investing.

Take Adarsh Bhatt and David Ongchoco, both 28, who met as undergraduates at the University of Pennsylvania. Four years ago, they launched the New York-based Comma.

Adarsh Bhatt and David Ongchoco [Photo: Courtesy Comma Capital]

Ongchoco, who grew up in Manila, started researching hackathons in high school, and then met Bhatt, the son of an engineer who’s worked at Intel and Oracle in Portland, Ore., their freshman year of school. In the early 2010s, as founders became ever-younger, some VC firms developed new programs to extend their reach beyond their usual, more mature networks. Bhatt, a computational biology major, and Ongchoco, who studied computer and cognitive sciences, began learning about venture through the college tours that Y Combinator organized for its partners and portfolio companies, to teach students about startups.

Ongchoco also worked with First Round Capital’s Dorm Room Fund, which tapped college students to seek out, and make small investments in, their fellow student entrepreneurs. “The experience made us realize we could be valuable partners to founders,” he says.

The two graduated into regular jobs at high-growth startups, but soon found themselves on the receiving end of perpetual requests from peers seeking advice on fundraising. “They were more comfortable talking to us before talking to institutional funders,” Ongchoco explains.

That led to invitations to invest in “friends and family” rounds. In turn, Bhatt and Ongchoco began pulling in other young operators as additional angels. “The founders really liked the types of people we were bringing to the cap table—software engineers, product managers, strategists—all people who could help post-investment,” Bhatt says.

When COVID hit, the two created an online community for about 75 people they pegged as either potential future founders or great candidates to become first hires. Suddenly, the pieces began to gel. Why not take it to the next level?

A few calls later, and their first, $5.5 million fund was born with LPs from well-known VC firms, tech company executives, and smaller family offices. This past year, they raised a second, $10 million fund that Cendana is anchoring, to invest in digital health, edtech, fintech, and SaaS companies—of the kind their New York peers are launching.

Today, Bhatt and Ongchoco nurture an 800-person network of potential founders and current operators—hosting events, happy hours, and small dinners. “Comma is a linchpin of different communities that exist in New York,” Bhatt says. “The credibility we’re driving comes from being a good central hub for knowledge exchange.”

The view beyond Sand Hill Road 

Other new VCs earn their way in by bringing something to the table few others have.

CiCi Bellis, 25, is a former professional tennis player who grew up in Silicon Valley. “Venture always interested me,” she says. “Going to dinner or a coffee shop, you’d overhear conversations about various startups.”

CiCi Bellis [Photo: Aaron Alvares Mendoza]

After injuries sidelined her pro career, Bellis leveraged her athletic experience into a job at a small sports-tech venture firm in Florida, where she lived while on the tournament circuit. She spent four years working directly with the chief investment officer on everything from sourcing, to diligence, to closing deals. 

“I never would have been able to do this in Silicon Valley,” Bellis says. With no professional work experience, and without a top-tier school on her CV (she’d turned down Stanford to play professionally), she wouldn’t have gotten in the door at a typical Bay Area firm.

But she also wouldn’t have gotten as much experience had she undertaken a traditional VC apprenticeship. “I got so much responsibility at the firm in Florida,” Bellis says. “I had led deals from start-to-finish multiple times. I felt I had all the tools to do it on my own.” 

Last summer, she opened her own shop, Cartan Capital. With $12 million raised from sports and healthcare executives and a focus on early-stage sports and health technology, Bellis says her value-add comes from sitting at the nexus of two important communities. Her sports connections make her interesting to major investors like Tim Draper, with whom she’s shared deal flow. And her tech connections make her attractive to LPs in the sports world who wouldn’t normally be able to invest alongside top tier VCs.

“I’m able to get involved in those deals because these larger firms want relationships with pro athletes, teams, leagues, and organizations,” Bellis says. Athletes, after all, are in demand to promote new products and services. Bellis is connected to them in droves, not just in tennis, but in other sports as well, via her former agency, IMG.

“I’m able to get involved in deals I never should be able to get involved in, just because I’m leveraging the athlete side of things,” she says.

From New Media to New Mogul

One barrier to entry used to be the ability to build reputations and networks. Limited partners (the institutions and individuals that provide capital for funds) won’t hand money over to an investor they aren’t confident can pick winners or get in on the juiciest deals.

The advent, a decade ago, of new investing platforms like AngelList and Carta began to chip away at the ‘old boys club’ nature of VC, making it easier for newer investors to access interesting startups and build track records. But some members of this latest wave of VCs have been able to make a name for themselves simply by using the brand-building power of new media.

The most prominent of these media-savvy investors is London-based Harry Stebbings, who started his Twenty Minute VC podcast at just 18, back in 2015. Through tenacity, meticulous research, and masterful networking, Stebbings convinced top figures in tech to appear on his show long before anyone knew who he was. He gained so much traction that, a year later, he dropped out of his undergraduate law studies to pursue the work full-time.

Nine years later, 20VC is one of the most popular venture podcasts in the world. But more important is how Stebbings has translated the reputation, network, and expertise he’s built into a venture operation. Three years ago, Stebbings launched his first micro-VC fund. Less than a year later, he raised another, larger fund, accumulating an astonishing $140 million war chest. His LPs include MIT’s endowment, Sequoia Heritage, and RIT Capital Partners, an investment firm originally founded by the Rothschild family.

Stebbings invests across a range of industries and at all stages of growth. Like many of his 20-something peers, however, he doesn’t have a conventional investment thesis. Rather, as he spelled out recently on Twitter, he mostly looks for markets where there’s little competition, where legacy companies persist in using antiquated technology, and that aren’t able to attract the best talent. In other words: Markets ripe for disruption.

An interviewer recently asked Stebbings if he minded that many still think of him as a teenage podcaster. “I love it,” he answered. Being underestimated, he said, is a kind of superpower. “Keep on thinking I’m a podcaster, and I’ll keep on writing $75 million Series B checks.” (Stebbings didn’t respond to Fast Company‘s request for an interview, perhaps because he is reportedly in the middle of raising a third fund, possibly as big as $400 million.)

Daybreak Ventures’s Rex Woodbury similarly forged a reputation via new media: namely, his four-year-old “Digital Native” newsletter about the intersection of technology and society, which now boasts 60,000 subscribers. After working in finance and founding Worthy, a mentoring app for LGBTQ+ people, Woodbury launched Daybreak in New York last year to invest in consumer and business apps with the potential for viral adoption, especially in health, education, job creation, and community-building.

“Venture capital is about [creating] serendipity: How do we stay top-of-mind for the next generational entrepreneur when she goes out to raise her round?” he explains. “If we can appear in 60,000 people’s inbox each week with long-form thesis pieces, there’s a good chance that a talented entrepreneur will read that piece and reach out. Or, someone in our network might say, ‘You’re interested in this topic? You’ve got to meet so-and-so.’”

A Challenging Environment

Not everyone is unequivocally bullish on this new crop of VCs.

“When the line is moving up and to the right, it’s easy and fun” to invest, says Chris Douvos of Ahoy Capital, a fund of funds that specializes in identifying emerging managers. Ahoy spotted the potential of the now-power player First Round, for example, back when it was just a glimmer in founding partner Josh Kopelman’s eye. “But when things get challenging and your LPs start complaining that their portfolios aren’t doing that great, the job kind of loses its luster.” Indeed, there’s been a shakeout of new firms since the economic downturn.

“In the bubble, you saw a lot of ‘tourist fund managers,’” says Michael Kim. “They saw a friend starting a little fund, so they decided to start one too. But ultimately, a lot of those tourist fund managers have been flushed out of the market. They weren’t able to raise, or they raised a small amount, and they can’t raise their next fund.”

Plus, venture is a long game. “The average venture fund lasts twice as long as the average American marriage,” Douvos points out. It’s difficult to expect a young person to stick it out for 15 or 20 years, until their funds close or investments exit, while they’re watching peers hop from job to job, or take time off to travel the world. “It’s a lot to ask of somebody who’s young and dynamic to commit to something that will last half to two-thirds of their [working] lifespan,” Douvos says.

Meanwhile, these new managers remain mostly untested in terms of the kinds of returns they can generate. The ecosystem won’t know for at least a decade, after enough exits have accumulated, what these younger VCs are actually capable of.

Peer-to-peer investing

Even with those caveats, LPs acknowledge 20-something investors still have unique advantages in tech’s ever-morphing world.

“Younger founders generally don’t want to work with their fathers’ friends,” Michael Kim says. “They want to work with peers, or people who are more empathetic to the founder journey.”

People like Goyal. She’s not just an investor. She’s also an engineer who writes code every day. She tells a story about another engineer who contacted her last year after seeing an open-source project she’d posted about on Twitter. “He said, ‘We should grab coffee,’” Goyal says. They did. As a former founder whose startup had been acquired by his current employer, the man seemed to be itching to start something new.

“At this point, most other investors would be like, ‘When you actually leave, let me know,’” Goyal says, “But I’m like, ‘Let’s meet up next week and keep talking.’” They continued like that for about three months, tinkering with an idea he’d been chewing on. “He became more sure about wanting to leave and build it,” Goyal says. When the man announced he was finally ready, “I said, ‘Great, I want to invest,’” Goyal says. The founder accepted her offer for a pre-seed investment.

Just days later, one of Silicon Valley’s behemoths gave the founder a seed-level term sheet that doubled the company’s valuation. 

“That’s the kind of [return on investment] LPs are looking for,” Goyal says. “If I weren’t there, putting in the work, week after week, when he wasn’t actually even starting the company yet, there’s no way that I would have been able to invest.”

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