What I Would Tell Someone Starting Out in Finance Today

The Question Behind the Question

People who ask me this usually want a shortcut. A reading list, a certification, a network to join. I understand the impulse. But after four decades moving between investment banking, building a software company, running a bank, and now managing a fund, the honest answer is not a shortcut. It is a short list of things I wish someone had told me plainly instead of letting me learn them the slow way.

Pick the Skill, Not the Title

Early on, it is tempting to chase the most prestigious title you can get. I would chase the skill instead. When I was doing financial modeling and due diligence work early in my career, the title was not glamorous. But the skill, the ability to take a messy set of numbers and tell a true story about them, has followed me into every room since. Titles change with every job move. Skills compound.

If you are choosing between two offers, one with a better name on the door and one where you will actually learn to do something hard, take the second one. You can always trade a skill for a title later. It rarely works the other way around.

Learn to Read a Business, Not Just a Spreadsheet

Finance trains you to read numbers quickly. It does not automatically train you to read a business. Those are different skills, and the second one matters more over a long career.

When I built a software company, I learned things about how a business actually survives that no amount of time on the banking side had taught me: how clients really decide to buy something, how a product succeeds or fails after the sale, what it costs in time and attention to keep a client past the first renewal. None of that shows up on a balance sheet. All of it shows up eventually in the numbers, just late.

If you are starting out, find a way to sit close to an actual operating business for at least a few years, not just the financing of one. It changes how you read every deal afterward.

Do Not Specialize Too Early

There is pressure, almost from day one, to pick a lane and stay in it. I understand why firms want that. Specialists are easier to slot into a desk. But a narrow specialty early on can close doors you have not yet discovered you want open.

My own path moved through investment banking, a founding stake in a community bank, a software company, a large institution, and eventually a fund I run myself. I did not plan that sequence in advance. Each step gave me a different way of seeing risk, and that range is what I now rely on most. If I had locked into one specialty at twenty-five, I doubt I would have built any of what came after.

I am not telling you to avoid depth. Depth matters. I am telling you not to mistake an early assignment for a permanent identity.

Build the Habit of Walking Away From a Deal

The hardest skill to teach a young analyst is not valuation. It is the discipline to say no to something that looks good on paper. Every deal that gets presented to you has been shaped to look attractive. Learning to ask what is missing from the pitch, rather than what is in it, takes longer to develop than any technical skill and matters more.

I would rather hire someone who has walked away from three good-looking deals for the right reasons than someone who has closed three deals without asking hard questions first.

Give Yourself Permission to Step Away

This one surprises people. After years running an investment banking division, I took a long period away from finance entirely, traveling and working on philanthropic projects across dozens of countries. It was not a break from the work in the sense of doing nothing. It reshaped how I thought about capital, about what development actually requires on the ground, and about what I wanted the second half of a career to look like.

You do not need to take seven years off to benefit from this. But build in room, at some point, to step back from the immediate next deal and ask what you actually want the next decade of this work to look like. Most people in finance never budget time for that question. The ones who do tend to make better decisions once they come back to the desk.

Start With the Long Game

If there is one thread through all of this, it is patience with your own development. The people who burn out fastest in finance are the ones trying to arrive somewhere in five years that should reasonably take fifteen. Build the skill. Read the business. Keep your options open longer than feels comfortable. The rest tends to follow.