Business_news 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



  • While some entrepreneurs take on investors to get their companies started, others bootstrap it — like these eight women.
  • All of them are now successful business owners, but they looked for creative sources of income to stay afloat while growing their companies.
  • Below, they offer a behind-the-scenes look at how they did it — from doing voice-overs in commercials to selling jewelry from old boyfriends on eBay.
  • Visit business Insider’s homepage for more stories.

As anyone who’s started a business — or wanted to — knows, those early days are tough financially. Aside from the cost of getting a company off the ground, you’ve got to pay your own bills while you wait for your first clients to come in.

While some entrepreneurs take on investors, others bootstrap it — like these eight women. All of them are now successful business owners, but what not many people know is that they looked for creative sources of income to stay afloat while growing their companies.

As it turns out, those side gigs not only brought in extra cash but also gave them surprising benefits they carry with them today. Here, they give a behind-the-scenes look of those early days — and some serious inspiration for other aspiring entrepreneurs.

Business_news The networking expert using her skills in all kinds of ways

Stephanie Thoma.

Courtesy of Stephanie Thoma

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.

Business_news The employee whose boss gave her a push

Shubham Issar.

Courtesy of Shubham Issar

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.

Business_news The bookkeeper by day, bartender by night

Kelly Gonsalves.

Courtesy of Kelly Gonsalves

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.”

Business_news The busy baker with a sweet voice

Katherine Sprung.

Courtesy of Katherine Sprung

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!”

Business_news The dog walker who wore Prada

Rhonda Moret.

Courtesy of Rhonda Moret

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!”

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Business_news The scrappy travel blogger who had a lightbulb moment

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Shabrina Koeswologito.

Courtesy of Shabrina Koeswologito

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.

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Business_news The maker who built her business on the job

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Lauren Egge.

Courtesy of Lauren Egge

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 // Doersmission 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.


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Dreamers // Doers

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