How to Decide Whether to Join a Start-Up

How to Decide Whether to Join a Start-Up

Ashley Louise

As a Girl Scout growing up on Long Island, Ashley Louise, co-founder and CEO of Ladies Get Paid, learned a thing or two about budgeting during cookie season. Each year, an 18-wheeler would roll up to her house.

“We’d move the cars out of the garage to fill the space with cookies—that’s how big our sales were every year,” says Ashley, 31. “My mom worked full-time, but cookie sales were her thing. She taught us how to track money, how to organize finances, and how to think about sales.”

In fact, this early focus on money management inspires Ashley today in her role as co-founder of Ladies Get Paid, which  provides the tools, resources, and community to help women negotiate for equal pay—and power—in the workplace. To date, the company has nearly 40,000 members as well as  communities in 19 cities around the country.

Ashley worked for several nonprofits, but while heading up business development at Vimeo, a video-sharing company, she attended a Ladies Get Paid meet-up. It was a revelation.

“I was feeling restless, and seeing all these women talking about money and how they felt stalled in their careers spoke to me,” she says.

In September 2016, when Ladies Get Paid was still in its infancy, Ashley began volunteering, organizing monthly panels and meet-ups. For a full year, she kept her day job, helping out at night and on weekends.

“It took me a year to be okay to make the jump and get the company to a place where we had enough money coming in,” she says.

Referring to herself as a “reluctant entrepreneur,” Ashley says she felt compelled to leave the corporate world.

“Leaving my job to join this venture threw a grenade into my professional and financial life,” she says. “But I had to do this—it’s that important to me.”

Here, Ashley shares three tips for other women considering joining a start-up:

Make sure the venture you’re joining is solid.

“Before I made the decision to join Ladies Get Paid full-time, it was important for me to know that this ‘thing’ could work. I knew it could, because we did a big conference in the fall of 2017, and so many people responded that I could see that we were building something really important.”

Be okay to move forward without benchmarks.

“It’s often hard to figure out our blueprint. Even benchmarking is hard because how do you know if you’re doing well or not? There aren’t that many companies that you can look to [and] see if you’re on track or not, so it’s important to be confident and keep moving forward in the best way possible.”

The bottom line begins—and ends—with you.

“When you’re running an organization, you’re the one who is on the hook when it comes to hiring. We’ve had a couple of people we thought we were going to be able to bring on full-time, and then it looked like we couldn’t. Even though we really liked having them on the team, it was a rough conversation to have … but this is something big that comes with the territory.”

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