Going Dark: How Paul Biggar is building the future of software

2 Jul 2018

Dark CTO Paul Biggar. Image: Startup Grind

Having run the gauntlet of the highs and lows of Silicon Valley’s tech world, Paul Biggar is on his fourth start-up, Dark, which points to the very future of software development.

As I chat with Paul Biggar through the miracle of technology that is WhatsApp – he’s in Iceland where it is a bit bleak and I’m sweating buckets in Ireland on the hottest day in 42 years – we try to figure out where our paths crossed before.

I’m reckoning it was 2005 in Demonware’s offices on Abbey St in Dublin on the eve of the launch of Microsoft’s Xbox 360 games console.

‘Ellen Pao is one of the people who went out on a limb and suffered in order to create that awareness and start everyone moving in the right direction. But we are nowhere near done by any means’

Zoom forward to 2018 and Biggar is an established entrepreneur in Silicon Valley. His previous start-up, CircleCI, where he is still a board member, makes continuous integration tools used by companies such as Facebook and has recently raised $31m in a Series C round.

His newest venture, Dark, which is creating pretty much the Swiss army knife for software development, has just raised $3.5m.

Biggar will be the guest of honour tomorrow night (3 July) at the Bank of Ireland-backed Startup Grind, which will be held at Google Docks on Barrow St, Dublin.

Speaking out

Biggar recently hit the headlines for confirming the details behind a now infamous Silicon Valley drug-fuelled sex party that captured the sense of entitlement and elitism in Silicon Valley as documented by Emily Chang in Brotopia: Breaking up the Boys’ Club of Silicon Valley.

The salacious story of the so-called sex party with faux fur and cuddle puddles was initially revealed in an excerpt published in Vanity Fair. Biggar added credence to the story in a Medium post that also went viral where he revealed that it was actually an official event held by a prominent venture capital company as a summit after-party and that it was attended by some the best-known billionaire entrepreneurs in Silicon Valley.

What Chang and Biggar in fact revealed was the ugly underbelly of the male-dominated Silicon Valley’s tech elite who use their wealth, power and privilege to get what they want.

“Give women access by funding them, by mentoring them, by introducing them, by supporting and advising them,” he wrote.

“Do not create an ecosystem where women are systemically denied access to funding and power, and then exploit that lack of power to coerce women into having sex with you.”

Speaking with Siliconrepublic.com, Biggar said he has no regrets about speaking out.

“I’m highly risk-tolerant. I weighed up the pros and cons and decided that it was probably the best time in my life to do this because I had just raised money and wouldn’t have to raise funding for another few years. On the other hand, ‘Jane Doe’ in the Vanity Fair article was a woman who couldn’t take that risk and I understand why. I had something to spare and it was the right thing to do to highlight the truth.”

Biggar has been in California several years now and left to find his destiny in Silicon Valley after completing his PhD at Trinity College Dublin (TCD).

A decade earlier after graduating from college with a degree in computer science, Biggar and a few friends took the plunge and attempted their first start-up. It fell on its face so badly that he doesn’t want to even recall how, and he took up a job at Demonware, the games tech firm that fellow TCD grads Dylan Collins and Sean Blanchfield sold to Activision in 2007 for $17m.

After Demonware, he undertook his PhD with a focus on software compilers and static analysis.

After giving a talk in Hawaii, Biggar stopped off in California for a week and saw a hacker house being advertised on Hacker News. He literally slept on the air mattress being advertised by a young start-up called Airbnb and found an energy in San Francisco that wasn’t apparent in the Dublin tech scene in 2010.

“In Dublin, no one gave a shit about software or the nerds, everyone was focused on property and finance. But when I got to California, it felt like home and I had found my crowd.”

Little did Biggar realise it at the time that he was about to plunge into start-up number two, three and four.

“I don’t think long-term or plan too far ahead. I’m fairly risk-tolerant and when I did my PhD or decided to go to California, it was against the grain or what people were telling me at the time. But it was an exciting time – Hacker News happened, Reddit happened. A lot of people saw the messaging: ‘an engineer shall inherit the Earth’. Business people didn’t really know shit about technologies and the engineers were finally in charge of building companies.

“We had people like Google chair Eric Schmidt who was a technologist from the start, who also did a PhD in compilers, and the mood was, ‘get out of the way and let the engineers do their stuff’. That spirit is not as pervasive today but for me it felt like a validation.”

Third time lucky

Picture of Paul Biggar

Dark CTO Paul Biggar. Image: Startup Grind

Newly arrived in California, some of Biggar’s roommates attended the prestigious Y Combinator accelerator and were preparing for a demo day after being featured in TechCrunch. “They were building things but there wasn’t any money in it, the funding bubble hadn’t seeped in and it was engineering at its purest.”

This spurred Biggar on to attempt his second start-up, News Labs, and join Y Combinator. Needless to say, the failure of News Labs taught Biggar some valuable lessons that served him well with start-up number three.

While developing News Labs, Biggar was courted by Mozilla and when the start-up wound down, he joined the browser giant to work on its JavaScript engine. After a year and a half, and after the promise of a coveted green card failed to materialise, Biggar ran out of reasons to stay at Mozilla.

“While I was building the browser, the compilers and editing tools they were using were terrible and it was top of my mind to build a better compiler.”

Start-up three was CircleCI, which focuses on creating compiling tools to enable continuous integration (CI) for developers building products.

“It went well from the start and it has been an incredible journey. Every day presented new challenges but by the time we were just three months old, we had our first customers and they just kept coming.”

The platform became the system of choice for developers working on platforms such as Facebook and Spotify. “It was a runaway freight train.”

Much of the success of CircleCI Biggar attributes to luck and timing. “It was a crucial time and the market was just right. People who tried to do what we did a year earlier had faded away. By the time we arrived, the market was ready.”

Biggar led the company for the first three years but encountered the classical tech founder’s dilemma: he wanted to continue to build things but was impeded in doing so by the realities of running a business, making sales and paying wages.

Fortunately, the experience and expertise of colleagues who had already started and ran companies before this meant that Biggar could take a back seat and focus on developing tech.

“I realised that being in charge meant I couldn’t enjoy my job as much. I was motivated to build product but leaders need to focus on building corporate culture and making sales and attracting key hires.

“There is a sort of myth in Silicon Valley that founders make the best CEOs, but sometimes you have to let others lead and I was happy to let the adults take over.”

However, after six months of giving up the helm to focus on the product, Biggar felt he was getting in the way and decided to take a sabbatical while remaining on the board.

“I travelled for a year, doing road trips across the US. I lived in Costa Rica and New York for a while but I started to get the entrepreneurial itch to start something new.”

Dark matter

That something new is Dark, a set of back-end development tools that combines many of the dev platforms such as hosting, version control, compiling, testing, analytics and more in one place.

‘The only way to do a start-up right is to ruthlessly focus on trying to validate or invalidate the ideas you have as quickly as possible and iterate as cheaply as possible’

In some ways, it pitches a brand new start-up against established players that include giants such as GitHub and New Relic, to name a few.

“It’s a combination of a bunch of things, including a new programming language called Dark, and effectively takes five common areas of software development that are currently separate and packages them into one.

“It’s an editor for code, a hosting platform, version control, databases and automation, and removes all the complexity from a bunch of tools that currently don’t talk to each other but should.”

As Dark’s CTO and co-founder, Biggar is taking all of the lessons and scars from his previous three start-ups and is focusing all of his energies on being an experienced, seasoned leader.

“I am starting from the hypothesis that everything needs to be validated as quickly and cheaply as possible. I am trying to take on the biggest, riskiest things and validate them at the start. Too many tech start-ups don’t build a product first, they take on a load of investment and overinvest in the wrong things.

“I am cutting corners to prove a bunch of hypotheses. Can people build software using a tool like this? The fact that we already have customers who are going to market with apps built using Dark indicates that we are on the right track.

“The challenge is how to get the next 20 or 30 customers and build this out in a way that we are not wasting time on the wrong things.”

Dark has been helped on its way by a $3.5m investment led by Cervin Ventures and private investors who include Silicon Valley CEOs and CTOs.

Time for Silicon Valley to be reborn

Biggar believes Silicon Valley has to change for the better and needs to shake off the tag it has gained for being too inward, parochial, sexist and elite.

“A lot of investors focus on social proof to ensure that their investment will be well spent. If you are an engineer from Stanford, ‘in that case, here’s a bucket of money’. Venture capitalists have historically been white guys who went to elite colleges and hired people from their fraternities. It had been a closed culture and that meant the only people who could get investment were people who looked like them or Mark Zuckerberg. Pattern-matching was a thing, but it keeps people out.

“The whole #MeToo movement showed that this happens in other industries, but it is wonderful that it has highlighted what underrepresented people in general already knew. For guys like me who are white and who look the part and had no problem fitting in, it is important that we recognise those privileges but it is also on us to open it up now to a wide range of people.”

As Biggar said, he has no regrets about confirming the veracity of the infamous sex party story.

“The frictions are mounting up. There’s definitely a sense of exceptionalism that a lot of people in the tech industry have or who believe they got where they did because of their own abilities, instead of luck, confidence or circumstances like where they were born or went to school.

“There is not nearly enough empathy in Silicon Valley for people who don’t have that luck; the people who drive Ubers or clean apartments are on average just as smart, they just ended up with a different life path.”

But things are changing. “One of the things that I’ve heard is that the investors who are putting money into VC funds are asking them when they are doing a new fund if there are any harassment stories likely to emerge, any #MeToo revelations to emerge, and investors are realising we need more underrepresented people to be invested in.

“That movement is currently seeing more of a focus on women than ethnicities but at least it is starting to move in the right direction, especially on the engineering side of things as companies hire more diverse teams. You are seeing conferences with codes of conduct that make all feel welcome. Then there is the backdrop of Trump’s America and the growing feeling that people need to focus in the right direction.

“Ellen Pao is one of the people who went out on a limb and suffered in order to create that awareness and start everyone moving in the right direction. But we are nowhere near done by any means.”

Finally, I ask Biggar what advice he intends to impart tomorrow night at Startup Grind.

“I think the most important thing I can tell people starting businesses is to really focus on validating what it is they are building.

“There are huge mistakes that people make. They have a vision and they go for it but they often don’t think about what is the cheapest way they can prove their idea wrong or right. I am seeing engineers building whole products before getting customers, when they don’t do even the minimum amount of product diligence to figure out if the whole thing will work.

“The only way to do a start-up right is to ruthlessly focus on trying to validate or invalidate the ideas you have as quickly as possible and iterate as cheaply as possible.”

John Kennedy is a journalist who served as editor of Silicon Republic for 17 years