From walking dogs to bartending, these 8 founders share the business lessons they learned from the side hustles that helped them survive while bootstrapping their startups

Tiffany Yu

CEO and Founder, Diversability

When Tiffany Yu started Diversability, an enterprise that aims to rebrand disability through the power of community, she knew she didn't want to raise outside funding. But given the organization's social mission, she also didn't want it to be her sole source of income.

"A few of my friends joke that I created the side hustle," shares Tiffany. "Even before I was a full-time entrepreneur, I was trying to think of ways to make a little extra income" — including selling jewelry through a direct sales company, listing items on Craigslist and eBay, and Airbnbing extra space in her house. One really fun job? Being cast as an extra in commercials.

All of those gigs gave her experience wearing lots of different hats — a crucial skill for an entrepreneur. "They made me a bit of a Swiss Army knife and taught me that I could figure out things on my own if I needed to," she says.

Stephanie Thoma

Networking Strategy Coach and Founder, Networking for Introverts

When Stephanie Thoma launched her coaching business to help introverted people build confidence, unlock their in-person networking potential, and establish authentic relationships, she knew she wanted to help the right people, rather than be desperate for clients. So, she got creative with multiple income streams.

"I've been a market research recruiter and moderator with an emphasis on finding hard-to-find niche participants in their natural habitats (think Catholic priests or moms with newborns) and having them take part in market research focus groups," Stephanie recalls. "I've also been a ghostwriter for an entrepreneur podcast and event producer in the real estate space."

As it turns out, each of those gigs has helped her in her coaching practice. "All of these projects have woven into one another with shared values, and I've built skill in rapport-building, human connection, and overall grit needed to run a business," she says.

Shubham Issar

Co-founder, SoaPen

When Shubham Issar and her cofounder came up with the idea for SoaPen, a colorful product that makes hand-washing fun for kids, they knew they were onto something. Others did, too, and they won a UNICEF challenge for the concept. Their prize money went entirely to R&D, so they needed income to support themselves and get the product to market. "As an immigrant founder, moving back to my parents' basement wasn't an option," Shubham adds.

In college, she studied industrial design and furniture fabrication, so she looked for jobs in that field. "I worked with an amazing design and build firm and got to work on awesome projects for companies like Macy's, Chanel, and some interiors in the West Village," she says. "Fabrication requires a lot of attention to detail, deep focus, and endurance — qualities that have definitely helped me on my entrepreneurial journey."

Plus, the job had an unexpected result: She gave her boss a SoaPen prototype to try with his daughter, who loved it so much that he told Shubham to quit her job to pursue SoaPen full-time.

Kelly Gonsalves

Founder, Totally Booked

Kelly Gonsalves describes her decision to start her company, a virtual bookkeeping firm for small businesses, as a bit last-minute. "I had just left a hostile work environment at a newly funded startup," she explains. "I didn't have a lot saved and needed to make money fast."

She deferred her student loan to have some wiggle room in her budget, then started looking for ways to make cash that didn't interfere with taking on clients — like waiting tables and bartending at night. Plus, "I signed up for every paying survey and focus group I could, I cashed in my literal piggy bank full of coins, and I sold off jewelry from past boyfriends that had no meaning," she says. "I was determined to make it work."

That determination paid off, but those scrappy times remind her to stay lean today. "Those days shape the way that I now spend my business' money," she says. "They taught me to operate on less."

Katherine Sprung

Owner, Squish Marshmallows

Katherine Sprung's company makes small-batch, handcrafted marshmallows, focusing on unique flavors and confections. While she loves the business, she admits that being a bootstrapped company without investors means not bringing in much those first few years.

To supplement her income, Katherine works as a commercial voice-over artist. She even set up a home studio so that she could do her side gig any time she wants. "Even if I work 12-to-15 hour days, I'm able to record commercials here and there," she says.

Some may think it's a totally unrelated field, but Katherine disagrees: "It actually helps a lot when it comes to press opportunities on TV and video, being comfortable speaking clearly, candidly, and concisely!"

Rhonda Moret

Founder, Elevate For Her and Elevated Diversity

Rhonda Moret was a successful marketing executive, working on high-profile brands such as Nike Golf, the PGA, and Universal. When she left to found her business, she realized she needed to have some money coming in quickly, but wanted to make sure it was flexible and low-stress. "I needed to find a way to earn money which didn't distract from my goal of building a purpose-driven brand dedicated to empowering women and elevating diversity," she explains.

The gig that fit the bill? Becoming a dog-walker. She loved it, though it was a far cry from the glamour of her marketing days. "I was humbled by the experience, but it only reinforced my commitment to make my new business a success." As she puts it: "I like to think of that phase of my life as 'the dog walker wore Prada' chapter!"

Shabrina Koeswologito

Content Creator/Founder, Slow Travel Story

Shabrina Koeswologito was trying to build her travel blog while pursuing a master's degree — no small feat. She also needed to pay for business expenses like website maintenance, but as an international student, there weren't many ways she could earn a regular income.

So she turned to a handful of flexible odd jobs: "I've done babysitting, participated in study lab research programs by universities, participated in an online survey, and worked as a part-time office cleaner and a clothing store receptionist," she notes.

Of course, while doing all these gigs, she couldn't travel and create new content. And that's when an idea struck: highlighting real women who work in the travel industry. "It turns out, this new #Powerwomenintravel content receives the most traffic on social media and helps me get more clients," she says.

Lauren Egge

Founder and CEO, Noka Supply

When Lauren Egge decided to quit her corporate job and launch her company — a line of everyday accessories that help you take better care of your health — she not only needed income but also a way to build prototypes for her products.

Fortuitously, she found a gig that let her do both: working at a local maker space doing machine maintenance and member support. The downsides? "The job paid a fraction of my previous salary, and the only shifts available were Friday to Sunday, 4 p.m. to 1 a.m., so my social life took a serious nosedive," she recalls.

But she also had access to the space's equipment and could spend her free hours working on her own projects. "I was able to 3D print and test dozens of designs … a process that would have been prohibitively expensive otherwise," she says. "That job ended up being critical to the success of my company."

Dreamers // Doers mission is to increase the number of successful ventures launched by women. It consists of Collective, a high-impact community reaching over 25,000 women globally, and Onyx, a highly curated private members' collective for value-driven female founders, trailblazers, and change-makers.