Rather than guessing what the market wanted, Jacqueline DeStefano-Tangorra decided to test it. The result surprised her: $33,000 in her first month in business — before hiring a single employee. Today, she has scaled her firm to more than six figures in monthly revenue.

In her twenties, she was immersed in complex data and AI work, including time as a Big 4 technology consultant advising large organizations on enterprise systems, executive decision-making and technology at scale. The work was demanding and formative. But alongside it, she began asking a different question: could her expertise create value outside a traditional, structured role?

Instead of overplanning or making a dramatic move, she turned to Upwork to test her assumptions about demand.

“At one point, I saw the market shifting dramatically in the expertise that businesses were seeking,” DeStefano-Tangorra says. “Upwork gave me a live market. If clients paid, renewed and referred, I knew something was there. If not, I adjusted.”

Rather than scaling quickly, she focused on patterns. Which problems appeared repeatedly? What clients were willing to invest in solving more than once.

“Most founders fall in love with ideas,” she says. “I wanted to fall in love with tangible evidence.”

As the signals became clearer, DeStefano-Tangorra shaped her offerings around consistent demand. She built repeatable frameworks, shifted from selling time to delivering outcomes and focused on long-term partnerships. Those early tests evolved into a consulting firm that has now worked with more than 200 clients, from national franchise operators to Fortune 500 enterprise organizations navigating data and AI solutions.

“I didn’t want a business that relied on constant personal output,” she says. “I wanted one that could absorb demand without breaking.”

Her background in high-pressure consulting environments proved foundational, but she was intentional about what she chose to carry forward — and what she left behind.

“My values and faith gave me permission to say no,” she says. “To certain clients, growth paths, and definitions of success that didn’t align with how I wanted to lead.”

But that conviction came with tradeoffs. As the firm grew, she had to walk away from clients who only wanted to work with her personally rather than the business she was building, as well as partnerships that conflicted with the standards and legitimacy she wanted the firm to represent.

At 29, after nearly 10 years in a consulting role, she committed fully to entrepreneurship. The decision felt grounded rather than impulsive.

“It wasn’t fearlessness,” she says. “It was trust. Trust that I had tested the market responsibly and, most importantly, trust that God would meet me in the step I was taking. And, spoiler alert, he did.”

Within months, her firm gained national attention for its early, practical adoption of generative AI, earning media coverage from CNBC, The Wall Street Journal and other outlets. She was invited to speak at events hosted by organizations including Young Presidents Organization, NASDAQ and the Tory Burch Foundation.

“Technology moves quickly,” she says. “But wisdom moves deliberately. We focused on where data enablement and AI services actually created value and where restraint mattered just as much as innovation.”

For DeStefano-Tangorra, entrepreneurship was never about escape. It was about alignment.

“Every business is built on a set of beliefs,” she says. “Mine were shaped by faith, a deep responsibility to produce results and the idea that success should strengthen your life, not fracture it.”

Today, she continues to scale her data and AI firm while advising organizations on how to adopt AI responsibly and effectively. The approach that built the business still guides every decision: test before committing, let real demand speak louder than assumptions and design systems that can grow without losing their integrity.

“The market is always talking,” she says. “The discipline is learning how to listen, and having the courage to build what it’s actually asking for.”

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