Meet a millennial who co-founded a $2 billion company: Scary opportunities are 'exactly how a stellar career is made'

Shadiah Sigala was always a go-getter.

The 38-year-old Mexican immigrant's mom moved her and her two siblings to southern California when Sigala was 7 years old. An honors student in high school, "My No. 1 dream in life was to be the most educated person" possible, she says. But she didn't quite know how to get there.

"My mother and all my aunts and uncles never did go to college," she says.

With help from the guidance counselor in her school, Sigala ultimately attended Pomona College for Latin American studies and later the Harvard Kennedy School for a master's in public policy. Thus, setting goals she wasn't quite sure how to reach and figuring out how to reach them became her M.O.

"One of my superpowers is having the capacity to be very comfortable wading through uncertainty, collecting facts and making decisions," she says. Ultimately, this superpower led her to co-found HoneyBook, a tech platform for financial management for small businesses. HoneyBook was valued at more than $2 billion in 2021.

Here's how Sigala built her career, and her advice for anyone keen to find their own successful career path.

After getting her master's, Sigala was hired to do project management at health insurance company Aetna. "I was getting paid annually more money than any of my family members could ever dream to make," she says of her $80,000 annual salary.

Still, she adds, she knew within the first week that, "I'm going to be so depressed here." She didn't like feeling like just a small cog in a big machine. She stayed in the company for two years, all-the-while saving up and considering her next move.

During her tenure at Aetna, she started learning about entrepreneurship and realized, "I'm a builder," she says. Starting her own company seemed like the best route.

Building on her love of cooking that started with her mom teaching her as a child, Sigala ended up founding a personal chef business in 2010, tapping her Pomona College alumni network for well-to-do alum willing to pay someone to cook their meals.

"And I paid my bills for about a year that way," she says.

As a young business owner, Sigala learned that she could be self-sufficient. But she realized cooking wasn't for her. "My time doesn't scale," she says. Plus, it was a low margins business.

Sigala's then-husband ultimately moved the two to San Francisco in 2012, and it was there that she discovered the world of tech. She began booking informational interviews with anyone in the industry who would talk to her, and asked questions like, "Do you work at a startup? What does that mean? What is tech? What is software? What is hardware? What's consumer? What's marketplace?"

As she learned that entrepreneurs in Silicon Valley build tech, in part, to solve problems, she realized the problem she herself would want to solve is one she'd encountered as a business owner: There was no streamlined way to deal with backend logistics like emails, payments and invoices.

When she met three Israeli entrepreneurs tackling the same problem, they realized, "Why not digitize all these crappy tasks that micro small businesses have to get out of the way so they can actually focus on doing what they love?"

That idea would turn into HoneyBook, founded in 2013 and where Sigala would spend five years in lead sales and HR roles. The company now boasts more than 200 employees, according to LinkedIn.

In 2018, Sigala co-founded her latest venture, Kinside, a child-care marketplace offered as an employee benefit. As a now mother of two, the inspiration for the company came as she tried to navigate the U.S.'s complicated child-care system herself. Kinside gives new parents one single place to find child care in their area.

The company has raised more than $16 million, according to Crunchbase. Sigala is currently serving as its CEO.

When it comes to advice she'd give others looking to find their way in the workforce, Sigala suggests letting fear and excitement be your guide. As you're looking for your next role, ask questions of the people around you and be open to new directions. If an opportunity "feels like it's above your pay grade, that is exactly how a stellar career is made," she says.

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