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justus shaw Seth Herald/WSJ

His $7,000 coffee cart pulled in $100K+ in 8 months — but he still hasn’t made a dime. The challenges of being your own boss

America’s up-and-coming Gen-Z demographic is increasingly souring on the traditional career path and instead striking out on their own as AI continues to swallow up entry-level white-collar jobs.

A recent study from small business services provider Gusto noted that, “for the first time ever,” Gen Z comprised 9% of new startups across the U.S. in 2025, against 5% of baby boomers starting their own companies. According to Gusto, the data indicates a “fundamental transformation” through the U.S. economy.

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“The current job market is leading young professionals to get creative,” Sam DeMase, career expert at ZipRecruiter, told Moneywise. “This is driven simultaneously by economic necessity and Gen Z’s desire for professional agency.”

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That doesn’t mean the entrepreneurial road is easy for new business owners, especially one in their 20s starting a business for the first time.

“It’s maybe even a healthy pressure, like, well, what’s my thing?” Justus Shaw, 25, a former corporate mobile app developer, told The Wall Street Journal.

Moving on from the traditional W-2 corporate world, where he earned about $60,000 annually, Shaw launched a full-time coffee-cart catering start-up in 2025. The coffee cart rollout cost $7,000 to get off the ground, and Shaw said he had to financially support six staffers, who helped him earn $100,000 in gross revenue. But a healthy chunk of that cash is earmarked for current and future company expenses.

“The business has to make a lot more money for me to still walk away with some money,” Shaw told The Journal.

Making the freelance life a good financial fit

Shaw is not alone in launching a startup and almost immediately facing the financial risks that come with business ownership for younger entrepreneurs.

“Necessity founders can still build good companies, but they start with a shorter runway and less room to wait for the right customer,” Kira Shishkin, founder and CEO of informed.now, a San Francisco-based news research company, told Moneywise. “For instance, the risk I’d flag first is that a founder who needs income this month will take any revenue, often at prices too low to ever pay a salary.”

The good news is that with some wisdom, foresight and constant real-world testing, young entrepreneurs can build a career platform with their name on the door. That journey, startup experts say, requires following some hard-earned advice.

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Get a good grip on day-to-day financial realities

There’s often a large financial gap between being traditionally employed and starting as an entrepreneur.

“You lose consistent base salary, bonus, medical coverage, 401(k), employer-shared taxes and paid days off,” DeMase said. “This adds up quickly to $15,000, in addition to the base salary loss.”

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That’s why it’s critical, before pursuing entrepreneurship, to make sure your savings account can cover at least nine months of living expenses. “Then, set aside at least three months’ worth of business costs, including startup and recurring expenses,” DeMase advises.

Figure out if your business can carry a salary, and quickly

Revenue is only a number that founders post online. It doesn’t clarify the amount of cash left after rent, supplies, payroll, taxes and loan payments.

“A coffee cart that grosses $100,000 in eight months can still pay its owner nothing when every dollar goes back into the cart,” Shishkin noted. “I’d tell any founder to pay themselves a fixed amount from the first month, even a small one, so the business has to prove it can carry a salary.”

Don’t lean too heavily on artificial intelligence

While AI can produce a business plan, a logo and a website in an afternoon, a founder may believe the technology can handle the business long before a single customer has paid. That’s not the case, Shishkin said. “AI can’t tell you whether strangers will pay for what you sell,” she noted. “That test, done in person with real customers, is the question I’d want answered before any other.”

Other business experts agree, noting that customer acquisition still requires understanding why someone would choose you, finding a credible way to reach that person and learning from their response.

“Delivery requires setting expectations, checking quality and handling problems,” Dr. Morissa Schwartz, founder of Dr. Rissy’s Writing & Marketing and GenZ Publishing, told Moneywise. “The founder remains responsible for those decisions, even when a tool helps with the preparation.”

A useful habit for any newly minted entrepreneur is to keep two separate lists: assumptions produced during planning, and facts learned from customers or actual work. “Ask AI to help identify what still needs testing,” Schwartz said. “Update the plan when the evidence changes.”

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Brian O’Connell Contributing Writer

Brian O'Connell is a US based former Wall Street bond trader and author of two best-selling books: "The 401k Millionaire" and "CNBC's Creating Wealth". His work is featured on national finance and business platforms like TheStreet.com, CBS News, CNN, The Wall Street Journal and Forbes

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