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A millennial who left her full-time job at PwC when her freelance side hustle took off shares the 3 ways to build a new business

Allie Kelly   

A millennial who left her full-time job at PwC when her freelance side hustle took off shares the 3 ways to build a new business
  • Jacqueline DeStefano-Tangorra left her corporate job to freelance and build her own tech business.
  • DeStefano-Tangorra used AI, including ChatGPT, to streamline work and grow her business.

Jacqueline DeStefano-Tangorra was working as a financial auditor at PwC when she started freelancing, and a few years later, the 30-year-old became CEO of her own firm.

When the pandemic hit, DeStefano-Tangorra joined the freelancing platform Upwork, pursuing technology and data analysis projects.

In 2021, as her client base grew, she launched Omni Business Intelligence Solutions. Soon after, she left her corporate job to work full-time with clients on their data and intelligence strategy.

"I always knew I wanted to do something where I either own my own business or I was in a leadership role position," she told Business Insider. "I decided, because my business started doing really well on the Upwork platform, that it was no longer a side business."

In the three-and-a-half years that OBIS has been operating, the business has booked 131 new contracts and nearly $470,000 in earnings on Upwork, according to documents reviewed by BI. DeStefano-Tangorra also makes money from clients outside the freelancing platform, but declined to disclose those earnings.

Side hustles and freelancing have gained traction since the pandemic as more people look for remote and higher-income job options outside the traditional 9-to-5. Last year, there were 64 million Americans who freelanced for part or all of their income, making up 38% of the US workforce, per Upwork data. That's a 2% increase from 2020.

For other professionals thinking about a career pivot, DeStefano-Tangorra encourages them to lean into freelance and emerging technology.

Identify your transferable skills

DeStefano-Tangorra said her accounting background translated well to her new career in data analysis. She was already well-versed in skills that helped her build her OBIS portfolio — scrubbing data and developing insights.

"I was always looking for anomalies," said of her career previous career at PwC. "My mind was trained for that."

She advises other freelancers to think about the industry knowledge they already have, and how it can be carried over into a side hustle or full-time job pivot.

Leaning into skills she was already good at gave DeStefano-Tangorra the momentum she needed to be a successful freelancer. Career changes can be daunting, she said, so it's important to choose a field where you have existing interest.

Use technology to your advantage

Building a business in the tech industry put DeStefano-Tangorra at the forefront of tools like ChatGPT. And, becoming experienced with generative AI has given OBIS a competitive edge, she said.

New technology has the potential to disrupt businesses and the job market, but DeStefano-Tangorra said it could also lead to opportunities for entrepreneurs.

"'How can we make this work for us?' is my mindset,'" she said.

DeStefano-Tangorra said she "wears so many hats" as a founder, and embracing technology has helped her scale her business. She has previously used AI to help organize complex data, write blog posts, and help market her firm.

"I'm not just doing one thing for a company," she said. "I'm a salesperson, I'm a marketing person, I'm an accounting person, I'm a technology consultant."

Build your network

DeStefano-Tangorra said she initially emphasized profile growth and positive client reviews on Upwork over money. As she began to take on more clients, her income grew naturally.

Freelancers in the tech and AI space should not only deliver high-quality work, she said, but be open to how the field is evolving. She has taken opportunities to attend and speak at events, and continues to learn how her industry is changing, she said.

"Build your networks of people and resources that you can lean on that are going to keep you sharp," she said. "Any time you're going into technology — especially now — the pace of change is so fast, that you will need everything you have in you to keep up with it."

Have you left your traditional 9-to-5 job for a side hustle or freelance gig? Are you willing to share how you make and spend your money? Reach out to this reporter at

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