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Home » I Took a Calculated Risk and Left JPMorgan for an AI Investment Bank
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I Took a Calculated Risk and Left JPMorgan for an AI Investment Bank

EditorBy EditorOctober 13, 2025No Comments5 Mins Read
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This as-told-to essay is based on a conversation with Varun Agarwal, a founding employee at OffDeal, an AI investment bank. The following has been edited for length and clarity. Business Insider has verified his employment and academic history.

For a college graduate looking to work in finance, it’s typically a no-brainer to pursue a career in investment banking.

What a career as an investment banker prepares you for is very enticing. You get great pay while working closely with executives from large public companies. You get to brush up on your soft skills while picking up technical skills like financial modeling.

The biggest lesson I learned from my time in investment banking was how to perform a wide variety of tasks efficiently. It also taught me how to ask the right questions when evaluating businesses. Working on deals honed my intellectual curiosity and sharpened my judgment when making investment decisions.

Joining OffDeal was a calculated risk

I considered starting my career at a tech startup instead. What held me back was my own aversion to risk. I studied at the University of Minnesota, where few people would take the plunge into entrepreneurship. Investment banking was the safer and prestigious path to take.

I figured that I didn’t have any tangible skills to offer if I wanted to build or join a startup. Investment banking felt like a good way for me to build up my skills in the event that the right startup opportunity emerged.

I ended up working as an investment banker for three years, first at Piper Sandler and then at JPMorgan. Incidentally, both roles were based in the Bay Area, which helped expose me to the startup culture in Silicon Valley.

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Seeing 21-year-olds start companies and raise millions of dollars was exhilarating. I thought to myself then, “Hey, why can’t I do that too? Why don’t I join a startup and take a big risk myself?”

That’s when I started speaking to founders and investors to map out the next steps of my career. One day, while scrolling through LinkedIn, I came across a post from Ori Eldarov, the founder of the AI native investment bank, OffDeal.

I was drawn to OffDeal’s mission and its use of AI and software to address the exact pain points I faced as a junior banker at JPMorgan.

Their focus on small businesses resonated with me at a personal level. My mom runs her own dental practice and is a small-business owner. Growing up, I saw that most business brokers could not run a proper Wall Street-level process when handling transactions for small businesses. I knew I had to be a part of OffDeal.

OffDeal is like Jane Street, but for investment banking

What’s unique about OffDeal is how each deal we handle is handled by a two-person team comprising one banker and one engineer. So far, I have been working on deals with OffDeal’s founding software engineer, Luis Ruiz Morel. Both of us get to take a cut out of the deals we do.

We also work a lot faster. At bulge bracket banks like JPMorgan, a company valuation could take weeks or even months to complete.

At OffDeal, it can be completed in one to two days at most. I just need to work with Luis to conduct the valuation using our proprietary software. Gone are the days when I had to painstakingly plug my numbers into an Excel spreadsheet.

It’s not just modeling. AI and technology have completely transformed my workflow as a banker.

In the past, I had to take notes manually when I sat in on Zoom calls. Now, AI can transcribe those calls for us.

And when it comes to putting together pitchbooks, I don’t have to spend hours going back and forth with my managing director and clients to polish them. Instead, our AI agent makes those revisions automatically, which saves us a lot of time.

The upside to all this is that our bankers can do more deals and, more importantly, spend less time on grunt work.

When I was at JPMorgan, I usually worked on two to three live deals at once. Here at OffDeal, I can work on 10 to 11 deals at a time. I also get to spend a lot of time out on the road meeting with prospective buyers and sellers.

Now’s the best time to join an AI startup

When it comes to starting your career, you can’t go wrong with a job in traditional investment banking. It’s still a great industry to go into.

But I think it has become less risky to join an AI company like OffDeal. It may have been a bigger risk before, but it is becoming increasingly clear that AI will have a huge impact on our lives.

There’s a very small window of time where you can actually succeed and push your career forward in AI before it becomes a more mature industry. Becoming AI native and learning how to incorporate it into your workflow will pay huge dividends in the future.

Do you have a story to share about your career in AI? Contact this reporter at [email protected].



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