The Angel Chronicles: Cyan Banister

You’ve landed to our new weekly series - The Angel Chronicles, welcome!

In this weekly blog we explore the backgrounds, portfolios, and stories of successful angel investors. For our first edition we’re shining the spotlight on someone you may not have heard of, but that played a major role in Peter Thiel’s Founders Fund. We're talking about Cyan Banister.

You won’t see her too much in the public eye, but she is one of the most prolific female angel investors with over 100 personal investments and over 42 exits.

‍Who is Cyan Banister?

Cyan might be extremely accomplished but she did not come from an Ivy League school or a rich family. She is nothing less than 100% self-made. When she was just 15 years old she experienced homelessness and soon after she dropped out of high school, but her curiosity, mentors, and passion for capitalism led her to success.

She is a self-taught engineer who first worked in non-executive positions at NBCUniversal (and as a writer for TechCrunch!). Her first high-level position was at IronPort in 2003. The company later got acquired by Cisco and that’s when she found herself with an extra chunk of money that she debated whether to invest in stocks, land, or startups. 

As you may have guessed, she decided to invest in startups - and what a good choice that was because it turns out she has a natural knack for identifying high impact technology companies in their very early stages. She is now a partner at Long Journey Ventures and she co-founded Zivity, an adult-themed social networking app. 

Cyan and Founders Fund

Cyan was the first female investing partner at the iconic Founders Found, where she led seed and early-stage investments with an interest and passion for augmented reality, fertility, and businesses that help people with basic skills find the right work. She ultimately left FF because she realized her superpower was investing in early stage startups rather than later stage investing, which was a critical part of Founders Fund.

"I’m dyed in the wool early stage. I’m addicted to the hunt and to the passion that comes with the optimism of what is possible and I’m not cut out for later stage investing. I tried. I really tried. I gave it everything I had. FF was always supportive, however they are also stage agnostic and generalists and hoped I would be able to do all stages and I can not. I just can’t."

– Banister, on leaving Founders Fund in 2020 (Medium)

Cyan and her husband Scott Banister won the Angel of the Year Crunchie award at the 2016 TechCrunch ceremonies. Scott had a major influence on her angel investing journey. He was a successful entrepreneur and angel himself, and he started his angel career with PayPal, where he was the first investor and board member.

A look into her portfolio

She’s made over 100 angel investments and 42 exits. 

Some of her investments include: Uber, Thumbtack, SpaceX, Postmates, eShares, Affirm, and Niantic, Superplastic, LeadGenius, HotPotato, and more. 

Her most notable exits: Zappos, Uber, Upstart

Her latest investment: Her latest investment was in Series A round by TipTop on May 12, 2022, when TipTop raised $23M.

Her advice on how to pick angel investments

‍Dive deep into people: Cyan says products and strategies are likely to change, so angel shouldn't don’t focus too much on that. What matters most is the long-term relationship with the founders and whether or not you believe in them. Ask yourself if that is the right person to tackle the problem they are trying to solve, and would you drop everything to work for them? Cyan also notes she never ever Googles founders before meeting them as she wants to have the most unfiltered version and judgment as possible. 

Dive deep into market discovery: Cyan doesn’t just evaluate markets according to stats and data, she experiences them. What typical VCs would consider a waste of time, Cyan sees as her secret weapon. If she wants to invest in VR, social media, gaming, or whatever it may be, she immerses herself into the apps first hand and speaks directly to as many founders as possible. Her goal before investing in a market is to be the user and understand the users of that market. In fact, that's one of the reasons why her husband Scott suggested she get into angel investing, because of her inherent ability to be an early adopter and spot the trends before others.

But not everything is a win…‍

One of Cyan's biggest failures and disappointments was her $250,000 investment and loss in GameCrush, which paired paying male users with female gamers to play board games and video games. 

Although Cyan noticed some red flags between the founders before making the investment, she chose to stick with her commitment. Other investors tried to get the company to go mainstream and limit the role of female gamers, which Banister was not too thrilled about and the whole experience changed some of her investment rules going forward. Angel investing is after all a learning experience.

Another investment that affected her majorly was her was her involvement with Ecomom, a marketplace for environmentally friendly products. The founder and CEO, Jody Sherman, tragically took his own life when the company started failing.

This made her realize how important it is to look out for warning signs and make sure that founders get help when they need it, because the impact that running a startup can have on their well-being can be very negative.

If you're inspired by Cyan's story, make sure to read her full life story in this incredible article.

How to pitch Cyan

This one is for all the founders out there!

Cyan on her journey from angel investing to becoming a venture capitalist

Cyan and Jason Calcanis, another top investor in Silicon Valley, talk about her early investments, her investing journey, and what makes a great founder. A great watch!

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