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Interviews

Inside the Life of a High-Earning Internet Banker – Caveman Circus

Last updated: October 4, 2025 11:15 pm
Published: 5 months ago
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I work in a corner of Wall Street that most people only see in headlines — the Internet and Interactive Entertainment group of a major bank. We’re the people who sit behind the big “XYZ dot com merges with ABC” stories. When you hear that a streaming service is swallowing a rival or that a video game publisher is issuing billions in new bonds, it’s likely someone like me is in the background, building models, arranging financing, and whispering to CEOs about what’s possible.

In simplest terms, I’m an investment banker for internet and gaming companies. My job has two main parts. The first is raising capital — helping these companies tap public markets or issue corporate bonds so they can grow. It’s a little like getting a mortgage, except instead of a house you’re financing an entire company, and instead of hundreds of thousands, it’s billions of dollars. The second part is M&A — mergers and acquisitions — those labyrinthine deals where one company swallows another. We’re the brokers, the go-betweens, the architects of billion-dollar courtships. Despite the title, we don’t “invest.” We don’t sit around playing the markets. We sell. We advise. We make deals happen.

On paper, it’s a dream. I’m expecting to pull in about $1.2 million this year, which still stuns my younger self. But the price is brutal. I work about 100 hours a week. That’s not hyperbole. Younger guys actually sleep in the office. It’s seven days a week, and you’re expected to drop everything — yes, even your brother’s wedding — for the job. The city never closes, and neither do we.

The hardest part isn’t the lack of sleep; it’s the mornings. Waking up after you’ve stumbled in at 4 a.m., knowing you’re heading back to do it all again, is punishing. My fiancée and I basically see each other in passing during the week — mornings only. Weekends are sacred, but even then, work intrudes. We don’t have kids yet, and frankly I’m not sure how this would work if we did. I don’t want to be the kind of dad who only exists in the margins of his child’s life. We think we can last another two or three years, but there’s a clock ticking.

People ask how I don’t burn out. The answer is that I live like a man trying to outrun it. I take extravagant trips to wild places — backpacking through the Rockies, crossing two mountain passes a day, getting battered by storms. Some guys train for marathons or mountain expeditions. It’s a counterbalance. The intensity of the outdoors is the only thing that matches the intensity of the office.

I won’t pretend I’m immune to envy. When you’re in an environment where some people earn 20, 30, even 50 times what you do, it’s hard not to look at them and think, “I’m doing the same thing. Why not me?” I’m sure someone at the bank thinks the same thing about me. It’s by design. They keep us hungry, competitive. That absurd fire in your belly is what keeps you grinding year after year.

My path here was textbook: top undergrad school, engineering degree, strong GPA, technical work experience, then an MBA from a top-five program where I pulled a 3.8. Summer internship at the bank. Hired full-time. It’s competitive as hell, but not impossible if you start early. The real differentiator isn’t your GPA — it’s how badly you want it. Meet people at the bank. Call them. Get to know them. Show them you’re obsessed. Then ace the interviews. Be supremely prepared.

At the entry level, you live in PowerPoint and Excel, building pitch books and discounted cash flow models. As you rise, you move from spreadsheets to boardrooms — fewer numbers, more clients. At the end of the day, investment banking is sales. The guys with the deepest relationships win. It’s like being a professional athlete. To be a starter for the Yankees, you train year-round, travel constantly, and sacrifice everything. This is no different.

People think trading is rougher. Maybe by a hair. They scream more, write emails in all caps, misspell everything. It’s a different culture. But both worlds are unforgiving.

Yes, I save, but my expenses have grown with my income — nice apartment, high-end travel. The real pressure is time. When you haven’t had a single day off in three months and you finally get five, you’ll spend absurd amounts of money to make those five days count. My money is professionally managed because compliance rules are strict. The SEC monitors us and even our families for insider trading.

The motives in this industry aren’t just money. Money matters, of course. It makes the hours tolerable. But there’s a real thrill to it too. Every day, the things I work on make front-page news. CEOs call me for my opinion. The scale, the stakes, the access — it’s intoxicating. The worst kind of banker is the one who came for the lifestyle but can’t stomach the downside. You’ll burn out fast if you’re in it for the wrong reasons.

People assume we’re all blowing our money on strippers. Not me. I’m a geek, a numbers guy, an outdoorsman. My idea of a splurge is a backcountry ski trip, not bottle service.

If I’d inherited a trust fund after college, I’d be a mountaineer, a ski instructor, a backcountry guide. That’s my third act. Maybe I’ll open a heli-ski operation or a mountain gear shop someday. Banking, for me, is a means to an end — earn big, retire early, build a life in the mountains, raise a family.

If I died tomorrow, would I be happy? Honestly, yes. I have an amazing, beautiful, brilliant fiancée. I’m proud of what I’ve accomplished. I’m optimistic about the future. This job isn’t for everyone, but it’s been a hell of a ride.

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