Interview: Clayton Bryan of 500 Startups
By Angela Tai
Clayton is a Venture Partner at 500 Startups in San Francisco, where he is focused on making media, ecommerce, and frontier tech based investments. His 500 portfolio includes Printify, Public Goods, and BeatdApp.
From 2013 to 2015, Clayton attended Stern and served as a Partner on the Dorm Room Fund team in New York. Clayton worked with and invested in some of the best and brightest student founded startups on the east coast. His DRF portfolio includes Brooklinen and Kitsplit.
Clayton has over 15 years of experience in the tech space. Initially working as a community builder, he transitioned into business development, and over the past 5 years has worked in venture capital. Clayton is also one of the co-founders of the Transparent Collective, a non-profit launched to help founders of color connect with investors and mentors.
Growing up near the SF Bay Area, did you always want to work in the tech space?
I was fortunate to have technology around me in my early years. I can remember playing games on my family’s Apple Macintosh back in the day, and later learning typing using Mavis Beacon Teaches Typing. Technology was woven into the fabric of my every day life. In high school I started to code and going into college I thought computer engineering was the field for me, but ended up taking a different path within tech. To answer the question more directly, yes, but it wasn’t necessarily a conscious decision.
Do you feel that people treat you differently as a black man in tech? If so, how?
While I can’t speak for everyone, I’ve witnessed improvements here. Back in the 2000s it was easy to be labeled the “token”. There were times, more so in social occasions, where things could get uncomfortable (“you must be good at rap karaoke, right?”). I even took part in a photoshoot for a former employer to help promote a cool diverse working environment. Now there seems to be more initiatives both internal and external to some of the leading tech organizations focused on improving diversity the right way. There’s still a lot left to be done, but I’m hopeful. From my vantage point things appear to be trending in the right direction at this time.
What inspired you to launch Transparent Collective?
There was, and still is to a certain extent, a need for groups such as Transparent Collective to bridge the knowledge and access gaps. More specifically with Transparent Collective, we help emerging founders of diverse backgrounds get training on presenting their businesses to an investor audience, understanding growth drivers, and building a successful fundraising strategy. We want to level the playing field, we want to build a better network to disseminate the tribal knowledge that accumulates in Silicon Valley.
What are the 3 mistakes people make when they pitch to early stage investors like yourself?
Not doing their homework. Examples: pitching to an investor that doesn’t cover their sector/model or there is a round mismatch (asking for too little or too much money)
Not knowing their own metrics
Boasting that their product/service has absolutely no competition (This is hardly ever the case)
What are the top 3 qualities you look for when you’re interviewing talent?
When assessing a founder and their team:
Relevant experience - founder/market fit
Problem solving grit
Ability to recruit a world class team
What is your definition of failure?
Not learning from your missteps.
What is the single most important piece of advice you would give to someone who’s just getting into the industry?
Stay curious, stay hungry, persevere.