"I would get programming books from the Salvation Army without knowing that they were already massively out of date," Evan Cummack says.
Kiwi ex-pat Evan Cummack was recently named chief executive of Fin - an early-stage Silicon Valley firm that has just raised US$20m ($32m) in a series led by Coatue, with Coatue partner Arielle Zuckerberg joining its board.
The raise was also supported by First Round Capital, Accel, and Kleiner Perkins.
It's not Zuckerberg's first Kiwi connection. Her first job out of university was working for Wildfire Interactive, the San Francisco-based social media marketing company co-founded by New Zealander Victoria Ransom.
And during the early days of his tenure as Fin CEO, Cummack has created a Kiwi connection for the firm, recruiting Wellington's Psychoactive Studios to build the company's website.
He says he'll be sending more work down under because New Zealand software developers offer good bang-for-buck.
And more, broadly, Cummack is a believer in remote contractors and remote staff. In part, that fits Fin's brief. The startup's software is designed to make it easy for companies to keep tabs on how their staff are using different pieces of cloud-based software (he says its main competitor is managers "walking around the office to see what their staff are doing"). Marquee early customers include Coinbase and Airbnb.
But he was already an advocate for a scattered workforce - a trend that has of course been accelerated by Covid, which has forced change
"Building a distributed company is a hard thing to do, like eating your vegetables," Cummack says.
"You don't want to do it, but it is the right thing. It's like it forces you to write everything down. It forces all your management processes to be asynchronous and data-focused. It allows you to use the best talent from wherever it is around the world."
Zuckerberg (the youngest of four siblings that include Facebook founder Mark) and Fin founder Sam Lessin headhunted Cummack from his senior role Twilio - the cloud communications company the New Zealander joined when it was a scrappy startup and he had to literally share a desk. Today, Twilio - where Cummack was in charge of hundreds of engineers - has a market cap of US$68 billion. As a stock option holder, the Kiwi was one of 100 early Twilio hires who attended the bell-ringing when the company listed on the Nasdaq in 2017.
Cummack's life in technology started in much scruffier fashion.
He tells the Herald that when he was growing up as a teen in Paraparaumu, it wasn't pre-internet, but it was before high-speed broadband and ubiquitous how-tos were readily available. So he often turned to other sources.
"I would get programming books from the Salvation Army without knowing that they were already massively out of date," he says.
But that actually taught him a broader lesson, even if he didn't appreciate it at the time. "I think actually, there's, there's a lot of virtue in understanding previous generations of technology, even when they become sort of functionally irrelevant - because themes tend to repeat over and over."
Grateful that @cummack took our call and stoked to partner together on this! Congrats to @betterwithfin! https://t.co/Zimb52REsU
— Arielle "AZ" Zuckerberg (@ariellezuck) September 9, 2021
"And I remember one time, a friend of mine, and I were walking past an office building in Coastlands Mall and there was an office that was getting rid of 20 or so 386 computers. And we were like, 'Yeah, we'll take them' - not knowing they were already out of date. And I just remember my mum coming home, and they were stacked up in our living room. And she's, like, 'Get them out of here, immediately."
Regardless, he managed to pick up some skills. As Napster hit the mainstream, he built some software for his mother's 1950s dance club, which automated the process of mixing fast songs and slow songs when it staged a 'hop'.
He and a friend created QBASIC video games (if you're of a certain age, think Gorillas), then made them available through a website.
And after studying information systems and marketing at Victoria, he landed a job with NEC, which put him to work on the design and implementation of the Aphis fingerprint scanning and automation system.
Cummack upped sticks and moved to California in 2011, with a rough plan to land a job in Silicon Valley.
"It just seemed like Hollywood for technology," he says.
And like an ingenue getting off the bus in LA, the Kiwi only had the sketchiest of ideas after de-planing in San Francisco.
"I didn't even really know where Silicon Valley was," he says.
But he knew the scene.
"What I would refer to as like the second dot-com boom was happening - Web 2.0, as it was referred to at the time. A lot of companies were emerging that were delivering a lot of real value as startups and the fundraising situation was heating up.
"I was really obsessed with like companies like Digg and Reddit and Dropbox and a lot of the Y Combinator companies.
I wanted to know, "Can I run with these people, at the same speed?"
It turned out he could, although the early days were not very Hollywood. He joined Twilio as the startup's first solutions engineer. Although a team of one, he had to share a desk with another staffer - and we're not talking hotdesking but literally sharing.
Twilio became a multi-billion powerhouse over the next nine years, and Cummack became director of product and engineering and GM of the company's IOT (Internet of Things) division before being plucked to run Fin last December.
Fin was co-founded by Lessin with Andrew Kortina, best-known as a co-founder of Venmo - a payment app that's wildly popular in the US.
One Fin snider says Cummack credits his management style, personal drive and success to his upbringing in New Zealand. "I've heard him talk about 'number eight wire mentality' more than once," she says.
What led Lessin and key funding partner Zuckerberg to headhunt the Kiwi?
In skills terms, it was Cummack's success in B2B software, Lessin tells the Herald.
And, more fundamentally, "We saw that Evan was fundamentally a 'doer' who knew what it took to win and how to roll up his sleeves and lead from the front," the Fin co-founder says.
"We also saw him as a deeply strategic thinker, who saw Fin's potential and cared about the opportunity to build a great business as opposed to a 'good' business. He also was just an honest, smart, straight shooter who we believed the Fin team would trust and learn from, and we could trust with the company."
Did Zuckerberg and Lession and co use shares to lure Cummack from Twilio?
On this point, the Kiwi, is coy, though he does say, "If you join a [US technology] company at a certain level. at a certain time in the history of the company, you're going get a certain amount of stock."
Although he's generally a fan of software coming out of New Zealand, and plans to send more Fin work in our direction, his love doesn't extend to the developers who put our MIQ online booking system together - or at least the policymakers who okayed a system that rewards those willing to mindlessly hit refresh for hours.
"I gave up on it," Cummack says.
"It's frustrating. I haven't seen my mum in three years. I'd love to bring her out here. But, you know, even if I can't be there, I'd love to bring her here. We're both fully vaccinated. It's a little crazy."
Like other technology figures overseas, the ex-pat says if it would help free up a regular MIQ spot, he would be willing to pay his own way to add a room to the system.
Does he see himself returning home one day?
Long term, "I'd love to come back," Cummack says.
"I think it would be really fun to try and build, build something there."
And he says the way the world has changed means it would not necessarily be that radical a change for his career.
With hybrid workforces scattered between remote locations, "These days Silicon Valley is more of an idea than a place," he says.
"In the industry we're in, it's possible to spend time in multiple places, I have no family [in the US] so it wouldn't be too hard for me to, for example, spend some considerable amount of time in NZ and still be in San Francisco.
Auditors PwC: Cited disruptions to operations from that IT upgrade.