Meet Silicon Valley power couple Stewart Butterfield and Jen Rubio: he co-founded Flickr and Slack, she co-founded Away – they shared a joke proposal on Twitter and raised funds for Kamala Harris

Feb 3 , 2025

Entrepreneurs Stewart Butterfield, of Slack and his wife, Away’s Jen Rubio. Photo: @jennifer/Instagram

The entrepreneurial couple married in 2020 and welcomed a son in 2021; now they are building an impressive art and property portfolio and hosting political fundraisers

Canadian billionaire Stewart Butterfield is a Silicon Valley icon, famous for being the man behind Flickr and Slack. Meanwhile, wife Jen Rubio is a powerhouse in her own right, making hundreds of millions of dollars as the co-founder of Away, the viral luggage brand specialising in polycarbonate, hard-shell suitcases.

In 2019, the two business minds were called “Silicon Valley’s It couple” by Business Insider after it was confirmed they were engaged. They are now based in Aspen, Colorado, but also spend time in New York and New Mexico. Here’s what you need to know about the pair who are influential in politics, art and technology.

Stewart Butterfield’s road to success

Stewart Butterfield and Jen Rubio attend an exclusive event at New York’s Bowery Hotel. Photo: @jennifer/Instagram

He might have an estimated net worth of US$1.8 billion, but Butterfield, 51, is a self-made man. He made his first foray into the start-up world in 2002 by founding online gaming company Ludicorp with first wife Caterina Fake and a friend, Jason Classon. Butterfield and Fake later co-founded photo-sharing platform Flickr.

Yahoo bought Flickr for US$20 million in 2005, with the couple joining Yahoo in the process. However, both Butterfield and Fake left Yahoo in 2008. The break came amid their divorce, six months after the birth of their daughter, Mint Butterfield.

Stewart helped to establish Slack Technologies in 2009 and became the co-founder and CEO of Slack, the team-based messaging software, in 2013. The company was bought by Salesforce for US$27.7 billion in 2021, though Butterfield left the following year.

Rubio’s wildly successful luggage venture

Jen Rubio co-founded luggage company Away after an incident at Zurich Airport. Photo: @jennifer/Instagram

Jen Rubio, in her mid-thirties, was born in the Philippines and moved to New Jersey when she was seven. She held positions at eyewear company Warby Parker and fashion retailer AllSaints before she started Away in 2015 with business partner Steph Korey Goodwin. Rubio co-founded the company after her suitcase broke at Zurich Airport, reported Vogue. Her friends couldn’t recommend a brand producing quality luggage, so she realised there was a gap in the market.

It’s been widely reported that Rubio and Goodwin have an estimated net worth of US$130 million each, while Away was valued at US$1.4 billion in 2015. Per Inc, the company has had its share of ups and downs owing to the pandemic and crashing sales. In 2021 Rubio took over as CEO and in February last year the company cut its staff by 25 per cent.

Their low-key relationship – and a joke proposal

Stewart Butterfield jokingly proposed to Jen Rubio on Twitter. Photo: @jennifer/Instagram

The couple kept their relationship out of the spotlight, but in 2019, after Rubio confirmed that her company had just raised US$100 million, Butterfield jokingly proposed on Twitter. The official proposal came a few weeks later during a hike in British Columbia, Canada.