Why We Left Investment Banking to Build a Program for High Schoolers

We spent years inside real deal rooms at Global Investment Banks - advising on transactions worth hundreds of millions of dollars, sitting through the actual grind of the job everyone glamorizes from the outside.

And somewhere in those years, we both kept coming back to the same realization: neither of us had actually known what this job was like before we committed to it.

We'd chosen finance the way most people do - a mix of good grades, family expectation, and a vague sense that it was a "safe," respected path. It wasn't until we were years into our careers, sitting through our first real all-nighters building pitch books, that we actually found out whether we enjoyed the work itself - not the idea of the job, the actual daily texture of it.

We got lucky. We turned out to like it, or at least like it enough to build careers on it. But we spent years talking to friends, colleagues, and eventually students who didn't get that same luck - who'd committed to a stream, a degree, sometimes years of specialized study, only to discover much later that the actual job wasn't what they'd imagined.

There was a second realization that hit just as hard, a bit later: actually landing that first real internship or job was its own separate battle. Every recruiter wanted evidence we could already do the work - before we'd ever had a real chance to try it anywhere. We spent our own college years scrambling to manufacture some version of "relevant experience" from scratch, with no structured way to actually build it, just persistence and a lot of time spent figuring it out the hard way. It's a strange, almost circular problem: you need experience to get the experience.

That gap - between choosing a career, and ever actually trying it, and then actually being able to prove you can do it - felt like something worth fixing, not just something to accept as normal.

So we built Outset: a way for students, in high school and in college, to do what we didn't get to do until years into our own careers - actually try the work, build something real, and walk away with proof of it, well before the stream is chosen, the degree is picked, or the first internship application is due.

We're both still active in the industries we came from - this isn't something we built from a distance, looking back. It's something we built because we wished it had existed for us.