Brian Nichols is one of our Venture Partners at Hustle Fund and the GM of Angel Squad. 

He’s also a prolific angel investor who co-founded and leads Uplyft, the syndicate of 3,500+ angel investors (many of whom are Lyft alums) who’ve deployed over $30 million together across 70+ startups. 

We sat down with Brian to jam on how Angel Squad came to be. We dive into: 

1. How Hustle Fund became the home of Angel Squad
2. Realizing just how inaccessible angel investing is
3. The magic in the diversity of every Squad cohort

“If we put education from the pros and real investment practice into one program, we could create a special experience that you really can’t find anywhere else.” 

The early days: inaccessible angel investing communities

The basic premise of Angel Squad came to Brian when he realized, through running Uplyft, that there are millions of people around the globe who want to access angel investing. 

Yet, even if they’re able to try it, most of them discover they just don’t know how to do it well. 

He imagined it'd be cool to see a well-respected fund (like, let's say, Hustle Fund) give radical transparency into the fund’s approach to teach these eager non-investors about their best practices. 

Though, of course, that education alone could only go so far. These participants would also need to learn through doing. Investing requires repetitions to truly figure out what works. 

Instead of spraying checks into cool startups and realizing your mistake years later, you could attach yourself to a fund that reviews 700 deals per month to learn their battle-tested frameworks. 

The firm could share only their best leads with you and walk you through their analyses. To lower the barrier to entry, investment checks would start as low as $1,000. 

“A leap of faith” that worked out — really well

If they could roll all of these experiences into a program for people who are notably passionate about learning to invest, Brian knew it'd be something truly special in the space. 

He connected with Elizabeth Yin, one of the GPs and Co-Founders at Hustle Fund, whom he describes as “one of the best investors in the whole ecosystem.” 

After quitting a job he really enjoyed at On Deck, they took a classic, Silicon Valley-style “leap of faith” into trying this idea through the Hustle Fund network. 

In retrospect, says Brian, whenever a venture fund attempts to spin up an initiative like this, it usually just does not work. But Angel Squad has thrived. 

“We’re nearing 1,000 people who’ve joined Angel Squad in a year and a half. We couldn’t be happier. We never could’ve dreamed that this would grow so quickly.” 

Defining Angel Squad’s ethos of community support

When Brian first brought his early ideas for Angel Squad to Elizabeth, she replied with an extensive Google Doc in which she’d already brainstormed extensively about this very topic. 

Her end goal? “We’re going to bring 10,000 new people into this angel ecosystem.” 

This cemented his understanding of Elizabeth as someone who “lives and breathes startups. She’s just so sharp in how she evaluates and supports them, and I love working with her.” 

Her next contribution wound up becoming a crucial pillar to Angel Squad. 

Brian summarizes it: "The way capital is deployed today means that, when people are enabled to invest, they invest in people who look and feel like them." 

If you're unable to bring historically overlooked and underrepresented identities into the investing space, you're also far less capable of supporting the founders of these identities. 

Until they’re represented on the other side of the table, they’ll continue to be locked out of most significant fundraising opportunities. 

So, they resolved, “Let’s go find anyone who’s an accredited investor and wants to learn this. And then let’s bring in more folks and help them on their path to getting accredited by paying for their Series 65 exam fees” 

Angel Squad — at its core and to this day — is oriented to develop a more diverse network of angels, who are actually representative of the modern world we see and live in. 

“We’re intentional when we say Angel Squad isn’t an elite group. There’s no status assigned here. We want to welcome everybody who wants to learn to invest.” 

How Angel Squad improves with each cohort

Since the first Squad kicked off in January 2021, the Hustle Fund team (as well as industry observers) have watched each new cycle grow better and better as investors. 

So much has changed since then, Brian explains. And almost all of these new initiatives can be traced back to ideas from people within the community. 

To produce sharper, stronger investors, you have to listen to your Squad members. 

Strengthening the community & network

One common piece of feedback from Angel Squad participants is a point of pride for us: 

They're most surprised by just how unique and high caliber every one of their fellow Squad members is. It makes sense that they'd want to connect with one another in greater depth. 

They launched Squad Pals, a program that matches participants in the same time zone each month based on similar interests in industry trends, approaches to investing, etc. 

A fascinating network effect appeared, especially as angels began sharing what they discussed in their Squad Pal conversations to their broader online community for others to read. 

For instance, Joe could read that Jane and Jill talked about Jill’s time as one of the first PMs at Airbnb. Joe loves Airbnb’s impact on the industry, so he makes sure to reach out to Jill. 

That happened time and time again, and more and more people took initiative to form mutually positive connections. In a word, Brian describes this kind of community as "magic." 

Empowering Squad members to support founders

Ultimately, every Squad member is passionate about becoming a stellar investor. And all of the best investors are unequivocally dedicated to supporting their investments. 

The Hustle Fund team began linking up Squad members to support founders in their portfolio. 

There are a number of prolific designers in the Angel Squad community, including a senior UX designer at Apple and a designer at Google, who offered their time through open office hours. 

Many small teams (<10 members) with Angel Squad funding came in to get invaluable feedback on their app or site mock-ups from true professionals before pushing those out to production. 

For Brian, everything about Angel Squad comes down to connecting the dots between aspiring investors and early-stage founders to accelerate both parties’ growth. 

“We’ve built a lot of experimental initiatives on this front because Angel Squad is all about connecting angels and tactically supporting the founders we invest in.”

Learn, network, support founders and invest alongside Hustle Fund.