Having a side job is not stealing from your employer, but can actually make you a better employee, said April Underwood, vice president of product at workplace collaboration company Slack.
One of the unique things about Silicon Valley is that there is a real culture around having a career that — at any given point — looks more like a portfolio, said Underwood.
"The men who have been leaders in our industry have been doing this for quite some time, so I think there's certainly something to it," she said.
When not steering Slack's product strategy in her "day job," Underwood invests in and advises startups through the investing group she co-founded called #Angels. She is also Board Director of home buying service Zillow and helps run Slack's $80 million startup fund.
"There is a little bit of a hidden expectation there that having a role like the one I have here is so all-encompassing that it takes literally every waking hour of the day," said Underwood. "It certainly warrants that, but there are many other great operators out there — male and female — that, beyond what they're doing in their operating role, are also investing, advising and taking board seats."
By building a strong team at Slack, elevating co-workers and "working smarter," Underwood has been able to pursue all these interests and have a personal life (she's also step-mom to a 19 year old).
Underwood launched #Angels along with five female colleagues from her former employer Twitter in March 2015. The women — who invest individually — have since backed more than 50 companies and put almost $3 million to work, with investments ranging from as low as $10,000 "just to join along for the ride," up to $100,000.
It's not a classic VC fund: there are no limited partners, but rather each woman invests her own money. This allows them to make all their investing decisions themselves.
"Because of that, we have really been able to just pick the founders and teams we feel most excited about," she said.
Startups have been eager to capitalize on their operational experience at successful, fast-growing startups, said Underwood, who draws on her experience at Slack, Twitter and Alphabet's Google.
"It actually ends up being a mentorship that I like to do anyway, and help really promising founders, but I also get to be a part of the team and participate in the upside, assuming they're highly successful," she added.
Most of the deals come through the women's extensive Silicon Valley network.
"Angel investing is so networked that a lot of the deals, you find out about them either through the other institutional investors -- the seed firms -- or other angels," she said. "The word of mouth has gotten out about us, which has been amazing and so we've been lucky to have a lot of inbound interest from founders."
The team isn't necessarily looking for hit products, since they invest at the very early stage of a company's inception, said Underwood. Their investments include healthcare startups Color Genomics, Nurx, Carrot, Hale Health and Forward, whose co-founder and CEO is an ex-Googler.
"You look at Adrian Aoun at Forward, who had a really great run at Google X, so much so that Eric Schmidt is an investor in Forward as well," she said. "That's a really strongly positive signal about the leadership, the project vision, the ability to execute."
The group does not intentionally seek out companies run by women to invest in, but has more women founders than the industry average, Underwood said. A third of the companies backed by #Angels had at least one female founder and a quarter of their portfolio companies had a female CEO as of April 2016, the most recent numbers available.
"Across our portfolio, we feel like we have a good start in terms of diversity, but we always feel like we could be doing more there," said Underwood.
To that end, #Angels has also partnered with venture capital firms to co-host invite-only dinners for women in operating roles at some of Silicon Valley's biggest tech companies, who are interested in investing in early stage startups and sitting on boards.
"I am seeing a lot of female operators who are hungry and who have a bit of that — I don't know how else to describe it — but, that 'hustle,'" she said.
Underwood has been encouraged by the number of women who are not afraid of the potential pitfalls of taking on too much and are interested in finding ways to "have their hands in a few different things." Over time, the industry will see more stronger well rounded excellent female leaders as a result, she said.
Underwood also noted that women in early-stage startups often take on another duty: leading the way in establishing workplace policies and benefits to support women and other minorities.
"It's an interesting set of responsibilities you take on in addition to doing your job," she said.
The key is starting early, as they did at Slack, said Underwood.
"From some of the earliest days there was a desire to make sure that we considered diversity in our hiring processes," she said.
For example, Slack typically does not specify the number of years experience required in job listings.
"There's a lot of evidence that women and underrepresented minority candidates don't apply for jobs if they don't meet that criteria, and then sometimes white men that have less than that number of years experience end up getting those jobs," she said.
As of February 2016, the most recent data available, 24 percent Slack's global engineering organization identified as female, the company reported. Across the entire workforce, that number rose to 43 percent. Slack is continually reevaluating its policies and drawing on empirical studies to try to improve, said Underwood.
"We turn a self-critical eye to how we do everything, including should we do whiteboard exercises on the wall if we know that those sometimes particularly put at a disadvantage people of a certain population, whether it's women or another group," she said.
This approach is something that the angels talk to the founders they work with about, said Underwood.
"We try to be helpful and help them get candidates for key roles as early as possible that will help them have that foundation for diversity because then it's never forgotten, it's on the table from the very outset," she said. "Talking about things, bringing them to the surface, is probably the best cure for the ills."