🤝Teaching the Next Era of Angel Investors - Brian Nichols, Co-Founder of Hustle Fund’s Angel Squad

Who are the leading VC Fund/Syndicate GP’s and how do they think about allocating capital via Funds, SPV’s and the like?

Today, we are excited to present an awesome interview with someone who has experience across the board as a founder, operator, angel investor, and syndicate lead. For those of you looking to break into VC and may not have the “prototypical background” or who are interested in starting your own alumni syndicate, this one's for you!

The objective of this interview is to showcase many of the leading VC fund and syndicate GPs and provide them with an opportunity to delve deeper into their identities and investment philosophies.

Our GP guest today has done what feels like everything in the startup ecosystem from founder, to early employee for a company that went public to angel investor to alumni syndicate lead and to co-founder of an investor/educational platform for angel investors.

Let’s share more on this GP…

GP Profile:

Our GP spotlight is Brian Nichols, Co-Founder of Hustle Fund’s Angel Squad & Lead for Lyft’s Alumni Syndicate, Uplyft. Prior to Angel Squad, Brian was Co-founder of RewardTag, the First Market Manager on the West Coast for Lyft (oversaw 50%+ of all Lyft rides at the time), Operations Manager @ Zoox, part of First Round’s Angel Track, Head of BD @ Blackbird, and Head of Partnerships @ On Deck.

For context, we have done a few deals with Angel Squad and Uplyft and continue to be super impressed with their ability to grow & educate their angel community on the art of angel investing in recent years and select amazing companies to invest in.

Check out our interview with Brian below:

1. Tell us about your early days as an entrepreneur + working at Lyft?

I ended up working at Lyft after starting my own company right out of college. I ran my company, bootstrapped it for about three years, and then sold it.

After that, I moved back to the Bay Area and was looking for a new job. I was hired to run the California markets in 2014 for Lyft. This was back in the days of the pink mustache and fist bumping your driver when you sat in the front seat. I was responsible for growing the markets in balance, looking at supply and demand levels on a market by market basis for all of California, which accounted for over 50% of Lyft's rides at the time. My role eventually grew to helping our local general managers that we hired in 25 different markets, hire them, and help them get connected to the right teams at headquarters so that they could grow their markets in balance.

2. How did you get started in angel investing/running SPV’s?

I got started in angel investing in 2019 when, to put it bluntly, nobody in VC would hire me. My VC friends recommended I start a Lyft alumni Syndicate. I invited 200-300 of my friends from Lyft to join me in investing in the startups that I was able to source and share.

3. How did your operating experience at Lyft make you a better investor if at all?

My operating experience at Lyft made me a much better investor because when I was just getting started I really tried to focus on investing in marketplaces. I felt like I deeply understood the pain points of growing marketplaces from the early days, and so that helped me with evaluating which startups to invest in.

4. What do you love most about running an alumni syndicate?

There are a few things I truly love about running an alumni syndicate. The Lyft alumni syndicate has now grown to almost 4,000 people. We've let in people who are not Lyft alumni, but there are still hundreds of Lyft folks who are investing in companies. Number one, I love supporting the founders that leave Lyft to start their own companies. We've invested over ten times in ex-Lyft founders and have invested millions of dollars into their startups. I also love how helpful the early Lyft employees are when it comes to helping the startups that we invest in. Early Lyft folks are super high caliber and super scrappy. So their skill sets match up really well to the needs of startups that we invest in.

5. What’s one of the most promising investments in the Lyft alumni portfolio – how did you meet them, and was it obvious early on they’d be successful? If so, how?

One of the most promising investments is Contra. Contra is a marketplace of freelancers who are working on project-based work for clients. It's a new take on what contractor marketplaces should be in this post-COVID remote and hybrid work world that we're in today. We invested in the seed round and they've gone on to raise a Series B, and they are doing incredibly well.

6. Have you helped other alumni syndicates come to life after starting the Lyft alumni syndicate? If so, which ones?

In late 2019 to early 2020, I helped people at Airbnb, Square, Stripe, DoorDash, and Pinterest get their alumni syndicates off the ground. I think this was an interesting moment in time for the startup investing ecosystem where we were collectively empowering big groups of operators to become angel investors, a development which had not happened up until that point.

7. Tell us about the On Deck Angels program you started? What inspired this?

I was one of the first employees at On Deck in early 2020 when we were solely focused on helping founders start companies. At that time, we really viewed YC as our closest competitor. Then I came up with the On Deck Angels program. The idea was that we had all these amazing founders in the On Deck founder community but we hadn't yet connected them with high quality angel investors who were experienced at investing and could really help them get to their next stage. On Deck Angels was focused both on connecting them to our founder ecosystem and connecting them to each other.

8. What are you currently doing at Hustle Fund? Why did you make this move and what are some key learnings from this experience?

I left On Deck to co-found Hustle Fund's Angel Squad. Outside of my two kids and my wife, this is my obsession. Our program aims to teach professionals from all walks of life, from all corners of the globe, how to make investment decisions based on our fund's approach, and then give them access to invest alongside our fund into our top performing portfolio companies. I made this move because, after running the Lyft alumni syndicate and the On Deck Angels program, I realized that there is a huge opportunity to focus more on an overlooked segment of the startup investing ecosystem, which are all the people who are not yet in it. 

At Angel Squad, we create educational content like deal review sessions where we actively make investment decisions in real time while our squad members have the ability to learn why we are making that decision. We've built an amazing community of people from over 25 different countries all of whom share the same general interest in learning more about how to become a smarter early stage investor.

9. How is Angel Squad going?

It's going unbelievably well, better than we could have ever imagined when we launched it back in January 2021. To date, over 1500 members have joined. We've invested in over 60 companies to the tune of close to $25M. Many members have gone on to find full-time roles at venture funds or have even started their own funds. The majority of squad members have benefited from both the educational experience, the investing exposure, as well as building their network of high caliber professionals. We're super proud that we are empowering so many new people from different pockets of society to participate in this space that has largely been opaque and exclusive to date.

10. What would you recommend to prospective or experienced investors who want to get involved in venture capital or syndicates?

One piece of advice I would give to prospective investors is to develop a framework that you firmly believe in when you're assessing a startup investment, and stick to it. Be disciplined.. Consider all the inputs that matter to you when forecasting the success of a potential company and then score the companies you review based on this framework. This approach helps avoid the trap of feeling any FOMO, enabling you to focus on the aspects you believe in.

If you're trying to make venture capital a full-time job or if you're considering starting a syndicate, I’d suggest building a proprietary channel of high-quality deal flow and start sharing those deals with the investors you admire. If you do this well, they’ll start bringing you into deals, and the flywheel starts to spin.

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✍️ Written by Alex and Zachary 

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