A Cold Email, 4 Hours of Coding: How a Penn Student Broke Into Polymarket and a16z from Wall Street?

Author: Dhruv Gupta

Translated by: TechFlow

TechFlow Summary: In the fintech industry, which heavily relies on prestigious school pedigrees and insider referrals, "outsiders" often can't even reach the interview threshold. After experiencing the inefficient bureaucracy at major firms, Dhruv Gupta, a University of Pennsylvania student who previously secured quant internship offers from Morgan Stanley and Jane Street, made a sharp pivot. In just eight months, he charted a completely different path to break through.

From shooting TikTok videos that attracted an offer from Kalshi, spending four hours coding his way into Polymarket, to proactively joining the a16z media program and joining MTS on its third day of launch, he ultimately partnered with Erik Torenberg to build Cosign around a vision for talent discovery, detailing a practical playbook for outsiders to leverage top-tier teams.

How I managed to leave Morgan Stanley and Jane Street, and force my way into roles at Kalshi, Polymarket, MTS (@mtslive), and a16z within just eight months.

Leaving Morgan Stanley: Fed up with Big Corp "Corporate Theater"

When I first entered the University of Pennsylvania as a freshman, I didn't even know there were other career options beyond the FAANG tech giants.

While walking down the main campus thoroughfare, Locust Walk, I accidentally caught eyes with someone standing in front of the GRC club booth, and that was my first time hearing about the consulting industry; as for the glamour of investment banking and hedge funds, I knew absolutely nothing back then.

Before I had even secured a summer internship for my freshman year, I somehow accidentally landed a sophomore-year summer quant internship at Morgan Stanley.

I was frantically mass-applying to 2024 summer roles on the university recruiting platform Handshake, and casually clicked on a 2025 summer position. Against all odds, I passed three rounds of interviews and received an offer.

But this very role made me realize how much I despised corporate bureaucracy. During the final weeks of my internship, I tried to request an LLM API key for some experiments, only to be told: "If you apply two months before your internship starts, maybe we could approve it when you officially join full-time later."

The work pace was slow, expectations were incredibly low, and it felt like everyone had perfected the art of "corporate theater" while completely losing interest in the actual work.

Opening Kalshi's Door with Short Videos, Breaking into Polymarket with Four Hours of Coding

In my final year of high school, I started making TikToks to catch a girl's attention (who knows why I thought that would work). A few early videos unexpectedly went viral (Video 1, Video 2, Video 3), after which I developed a habit of posting regularly, mostly updating during summer breaks.

Over time, I became what others saw as a niche influencer focusing on engineering and quant content.

From the perspective of economic utility, I've always been interested in prediction markets. So when I received the DM above from @salmanso_, I felt like I had been chosen by destiny.

After shooting a few uninspired videos, I quickly realized what I actually wanted to do was build product from the ground up. Long story short, Kalshi didn't have a suitable product role for me at the time, so I sent a pretty blunt email to the only Penn alum working at Polymarket.

Although I initially got a reply from @wasabiboatresearch, they quickly went silent. So I spent four hours furiously coding and built these two slightly crude little projects below.

It was these two projects that successfully caught Will's interest. He commissioned me to develop software for news.polymarket.com that he had long wanted.

This eventually naturally expanded into me assisting in building the polymarket.com/polygraph companion tools, developing thespread.news, and conveniently writing a few articles along the way (Article 1, Article 2, Article 3).

During my time at Polymarket, I also almost end up co-founding two companies in this space due to a series of coincidences.

One was with the talented Augur and Gnosis co-founder @no__________end, and the other was partnering with a Wharton School statistics professor who is a leading expert on Markov chains globally and loves teaching probability theory using prediction markets.

Although neither startup attempt ultimately materialized, I gained a complete understanding of fundraising logic, how to read people, and several cutting-edge niche technologies. (If you want a sneak peek at the small projects I've honed around this topic, you can check them out here details).

Joining the a16z Media Program, Rushing to San Francisco to Co-build MTS

Just as my second startup was about to close its pre-seed round and required my full-time commitment, I suddenly realized I actually wanted to build products in the media sector, something I truly loved.

Luckily, a16z had just opened applications for its second cohort of New Media Fellows, spearheaded by then-partner @liangsays (Brent Liang).

We met and kept in touch. Later, when Brent left Andreessen Horowitz to found the new media platform MTS, he wanted to find someone to build a product system similar to what I had done at Polymarket.

My contract at Polymarket was conveniently about to expire. I've always loved journalism and the American drama The Newsroom, so the idea of getting real-world experience like the tech-savvy reporter played by Dev Patel in the show was incredibly tempting.

On the morning of the third day of MTS's live broadcast launch, Brent and I first discussed me joining the team.

Before the day was over, I had negotiated with all my professors to take finals online, packed all my belongings, said goodbye to graduating seniors early, boarded a flight to San Francisco, and booked a month-long Airbnb in the Tenderloin district.

At first, I was only responsible for building the mts.now/situations page, but I quickly realized MTS had the opportunity to fill a critical gap in public discourse. After our initial tracking of the Musk v. Altman trial went viral, I had even more motivation to continue building the product.

In today's era where Opus 5.5 and Astra are widely available, producing a high-quality daily explainer graphic seems effortless, but it was a completely different landscape in April 2026.

During that period, I enjoyed breaking down topics like the data center construction boom, the UFO phenomenon, and startup hiring for everyone on the feed.

In those early days, the outside world basically roasted us relentlessly. Working 12-hour days, seven days a week, non-stop in the war room with Brent and @netcapgirl, was one of the most worthwhile experiences of my life.

Even today, I deeply regret leaving them back then to finish my summer internship at Jane Street.

Here is a representative tweet MTS posted back then: “We built a tool to access all submitted evidence from the Musk v. Altman trial proceedings, including Greg's diary, text exchanges between Elon and Sam, the OpenAI LP agreement, and more—all now live at evidence.mts.now.”

Above all the noise, only we knew who the team was, what we were doing, and why we were doing it.

It turned out that grinding hard and striving to improve by 10% each day eventually paid off handsomely for the team, and I am incredibly bullish on every single step they take moving forward.

From Self-Built Talent Lists to Cosign, Productizing "Audacious Initiative"

After this summer ends, I'll only have six courses left to graduate. The sensible choices are limited to two: either take them all in one semester and graduate in December, or take fewer classes in the fall while balancing work.

I had already been chatting with Erik Torenberg (@eriktorenberg) during my time at MTS. Come summer, he painted a product vision for me, which eventually materialized into what is now @cosign.

Globally, I doubt there's another product that aligns more closely with my core values than Cosign. Recently, a friend reminded me that over the past year, I've actually been quietly maintaining a "top talent list," constantly sharing it with founders and VCs, hoping to help undergrads I mentored land internships at startups.

I hope Cosign can become a platform where friends and mentors can bring true go-getters, enthusiasts, fighters, and even obsessive talents to the forefront.

Looking back, it has indeed been a wonderful journey. Moving forward, I look forward to continuing to improve Cosign by 10% each day. It's time to start building!