Cloudflare's Matthew Prince still isn't sure he made the right call on The Daily Stormer

Prince explains how he deals with difficult decisions, and offers some advice to fellow entrepreneurs

For a few days in August 2017, Matthew Prince, co-founder and CEO of Cloudflare, was the internet’s public enemy number two. Cloudflare offers security services for websites, including protection against DDoS attacks, and in the tense summer days after the violent clashes between white supremacists and anti-fascist protesters in Charlottesville, Virginia, everyone from Silicon Valley CEOs to the Southern Poverty Law Center was asking Prince to stop protecting neo-Nazi news site The Daily Stormer.

It’s not a scenario Prince had envisioned when he set up the company. A law graduate with experience tracking spam with startups Unspam Technologies and Project Honey Pot, he co-founded Cloudflare in 2009 with Michelle Zatlyn and Lee Holloway. Since then, Cloudflare has raised $182 million (£130m) from investors including Google Capital, Microsoft and Baidu and, in May 2016, fended off the largest DDoS attack recorded so far. It now has more than six million customers, including Uber and Irish public-service broadcaster RTE.

Prince’s policy has long been to work with everyone; he points out that hackers often share and reuse code, so fending off one attack now could help to protect a completely different target in the future. At a town-hall style staff meeting, some employees expressed strong concerns about this policy. In the end, Cloudflare terminated The Daily Stormer's account, but six months later he still feels uneasy. “We’re a content-neutral service for many reasons, the biggest of which is: I don’t think my whims, and those of Jeff Bezos, Larry Page and Mark Zuckerberg should determine what’s online,” he says.

Here, Prince explains how he came to build Cloudflare and shares what he’s learned from dealing with unexpected challenges along the way.

Start with what you love

“I grew up in the mountains in Utah and we’d go walking, looking for moose on these huge plots of land that were public and everyone could use. The freedom was absolute. Then I went east to college and every plot of land was owned by someone, and I realised freedom was worth protecting.”

You’re always your parent’s child

“My dad was a journalist, a restaurant owner, the drivetime guy on local talk radio and a stockbroker. My mum opened six stores that sold gifts, stationery, flowers, coffee and kitchenware. I didn’t really know how to apply for a job – both my parents were making it up as they went along.”

Follow your passions

“When I was seven years old, my grandmother gave me a Macintosh II for Christmas and I just took to it like a duck to water. My mum signed up for computer science courses at the University of Utah so that I could go to the classes, which worked out pretty well…”

Matthew Prince’s productivity tips

What time do you get up in the morning?: 8am

How do you get to work?: I walk. I clear out the inbox on my phone and get focused on the tasks for the day.

When do you do your best work?: In the evening after everyone has left the office and it’s quiet.

What’s your secret to motivating a team?: If you hire people who are really curious and have a high degree of empathy, you can teach them anything, then set them really big problems and they respond.

Do you have an email hack?: Write short, concise replies and empty your inbox every day. If it’s been in my inbox for longer, it either means I’m never going to open it, or I’m not sure of the answer and I probably need to meet the person.

Learn to communicate your ideas

“I studied computer science and English literature at college. English literature helped me write and communicate better, which has proved far more important than my ability to write computer code.”

Don’t always back your hunches if smarter people disagree

“I started an online magazine with college friends that kept crashing the campus server. The school introduced us to a company with a new technology called PDF and some graduates with this thing called a browser. I thought we should double down on PDF but, thankfully, my friends all chose HTML.”

Build a team with different strengths

“I always look just beyond the horizon at where the world is going to be, but I’m not detail-oriented. I had a startup with school friends who were just like me and we almost killed each other. [Cloudflare co-founders] Michelle, Lee and I complement each other. Draw a Venn diagram with founders: you want just enough overlap to communicate and talk to each other, but space for each person to bring something different to the table.”

If you want advice, ask for money; if you want money, ask for advice

“The people who are the best at fundraising are relentlessly curious, and have a high degree of empathy and a low degree of arrogance. It’s tempting as an entrepreneur to come in and say, ‘I know how to do everything.’ It’s more effective to say, ‘I found this problem, this is how we’re thinking of solving it, what do you think?’”

A startup is a pirate ship

“Everyone can’t vote on every battle. You need to be the captain.”

Always know your legal position

“Studying law is an awfully expensive way to learn anything, but sometimes what you learn is priceless.”

Know when to ask an expert

“We got word that we were protecting a Paris organisation with a site written in an Arabic-looking language featuring Middle-Eastern men with beards and guns. We reached out to law enforcement and they said, ‘Don’t take it down, it’s Kurdish rebels. There’s no-one more against Isis [Daesh] than the Kurds.’”

Think hard before making tough decisions

“With The Daily Stormer, the site was bragging that Cloudflare was on its side. There was no way we could have the free speech conversation with people calling us Nazis. [But] it’s now a little bit harder for us to argue against a government pressuring us into taking down a site they don’t like.”

This article was originally published by WIRED UK