From Banking Dreams to AI Realities: How a Goldman Sachs Internship Sparked a Y Combinator Startup Journey

The Investment Banking Illusion

At 23, Raymond Zhao represents a growing cohort of young professionals who are rejecting traditional career paths in favor of the unpredictable but potentially rewarding world of AI startups. What began as a dream internship at Goldman Sachs in summer 2024 became the catalyst for an entirely different career trajectory—one that led him to cofound Structured AI and join Y Combinator’s prestigious Fall 2025 batch., according to technology trends

“Working at Goldman Sachs was my dream, but I quickly realized it wasn’t for me when I interned there as an analyst,” Zhao revealed in an interview verified by Business Insider. The revelation came despite successfully navigating Goldman’s highly selective process, which included online testing, virtual interviews, and intensive superday assessments., according to market insights

The AI Awakening

While his peers demonstrated genuine passion for financial markets, Zhao found himself disconnected from the work culture. “I worked long hours, sometimes staying in the office until midnight and occasionally coming in on weekends,” he recalled. “Other interns cared deeply about financial markets and did research in their spare time, but I didn’t.”

The turning point came during post-internship travels through Southeast Asia, where Zhao contemplated what truly excited him. Returning to Oxford for his Master’s degree, he immersed himself in the university’s venture capital and AI societies, where he discovered a different kind of ambition., according to market analysis

Building the Foundation

Through Oxford’s venture capital society, Zhao met his future cofounder, Isabel Greenslade, and began building a network of investors and entrepreneurs. “I realized I wanted to launch a startup so I could build something myself and steer the boat,” he explained., according to technology insights

The puzzle pieces fell into place when Zhao joined Oxford’s AI society during his final Master’s year. After months of ideation and pivoting, the team discovered their winning concept through third cofounder Brandon Smith, who identified a significant problem in his contracting work that sparked the idea for Structured AI.

Solving Real Engineering Challenges

Structured AI addresses a specific pain point in the preconstruction engineering world. “Engineers spend a lot of time on very repetitive manual workflows, a lot of which are text-based, like paperwork and building forms,” Zhao noted. “We built AI agents to assist them.”

The startup developed a copilot system that automates tedious aspects of engineering workflows, potentially saving countless hours of manual labor while reducing errors in critical documentation processes.

The Funding Breakthrough

Despite initial rejection from Y Combinator’s summer 2025 cohort, Zhao’s persistence paid off in an unexpected way. During his final week at Oxford in June, he skipped classes to attend an AI startup conference in San Francisco. “I hadn’t planned to raise money, but my founder friends encouraged me to try while I was there,” he said.

The gamble yielded remarkable results: within days, they secured approximately $500,000 in funding. This rapid financial validation allowed the team to focus on Structured AI full-time and strengthened their subsequent Y Combinator application.

Life in the Y Combinator Pressure Cooker

Now part of Y Combinator’s Fall 2025 batch, Zhao describes the experience as both intense and transformative. “There are a lot of young founders, some under the age of 21, and some who dropped out of university,” he observed. “It’s an amazing, super-ambitious community.”

The team has converted their San Francisco Airbnb living room into a makeshift office equipped with three monitors and extending desks. Their daily routine reflects the program’s demanding nature: “We wake up anytime between 4 a.m. and 9 a.m., get coffee, and work for the whole day. We’re going to conferences, taking calls, and going to events in the evening.”

The Startup Calculus

For Zhao, the decision to pursue startup life came down to a strategic calculation. “It was a calculation between building something in AI and the returns going directly to me, versus taking a corporate job, where you can wait years for a promotion.”

His advice to aspiring entrepreneurs is straightforward: “If you have an idea for a startup that’s keeping you up at night, I recommend trying to launch it. If you can make it work and have the appetite for risk, startup life can be very rewarding.”, as additional insights

Looking Toward Demo Day

With Demo Day approaching in early December, where teams pitch their progress to investors, the pressure is palpable but productive. “The pressure is real, but good work comes out of it,” Zhao acknowledged.

Reflecting on his journey from aspiring banker to AI entrepreneur, Zhao sees his current position as just the beginning. “YC is one of the most exclusive clubs in the startup world. I’m living a dream—one that came to me later down the line. Now, the next one is to build a massive company.”

His story exemplifies how early career disillusionment, when channeled productively, can become the foundation for extraordinary entrepreneurial success in the rapidly evolving AI landscape.

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