From Investment Banking to Entrepreneurship: What Changed in How I Think

The biggest change

In a large institution, decisions sit inside a system. As a founder, they sit with you.

I spent a significant part of my early career inside investment banking and institutional financial services.

Those environments taught me how large organisations make decisions, allocate resources, manage risk and coordinate across geographies and functions.

I worked with institutional investor clients including hedge funds, asset and investment managers, sovereign wealth funds, pension funds and insurers. Later, I moved into investment management, strategic advisory and eventually entrepreneurship.

The transition changed how I thought about almost everything.

Inside a bank, even important decisions are supported by infrastructure. There are policies, teams, committees, budgets, control functions and established processes.

As a founder, much of that disappears.

You still need judgement. You still need process. But there is far less distance between the decision and the consequence.

Speed

I learned that speed is valuable – but only when the decision is reversible.

Large institutions are often criticised for being slow.

Sometimes that criticism is fair. Sometimes the slowness exists because the decision has a large blast radius.

Entrepreneurship taught me to separate decisions by reversibility.

If a decision is relatively easy to unwind, speed can be an advantage. You can test, learn and adjust.

If a decision creates a long fixed-cost commitment, regulatory consequence, major reputational exposure or significant capital risk, moving quickly for the sake of speed is rarely a virtue.

I became much more comfortable making fast decisions when the downside was bounded, and much more deliberate when the decision could materially restrict future options.

Information

Founders rarely get to wait for certainty.

Institutional environments are built around information gathering.

Reports are produced. Data is analysed. Due diligence is completed. Senior stakeholders are consulted.

Entrepreneurs often have to decide before the picture is complete.

That does not mean guessing.

It means understanding which missing information actually matters.

I became less interested in having every data point and more interested in identifying the few variables capable of changing the decision.

That is a useful discipline in business and in lending.

Most decisions do not fail because one minor fact was unknown. They fail because one major assumption was never challenged.

People

I became less impressed by credentials and more interested in whether someone can execute.

Institutional finance places understandable weight on experience, qualifications and career history.

Those things still matter to me.

But entrepreneurship made execution much more visible.

A strong CV does not necessarily mean someone can build from ambiguity. Seniority does not guarantee ownership. Intelligence does not guarantee judgement under pressure.

In a smaller business, you quickly see who can turn an unclear problem into a practical next step.

I became much more interested in reliability, commercial judgement, communication and whether someone takes responsibility without waiting to be managed through every stage.

That does not mean process becomes irrelevant.

It means the quality of the person operating the process matters more than the sophistication of the process itself.

Process

I wanted the discipline of institutional finance without importing the bureaucracy.

One thing I did not want to lose when I became an entrepreneur was respect for process.

Good controls exist for a reason.

Documentation matters. Data matters. Clear ownership matters. Follow-up matters. Risk management matters.

But a growing business can damage itself by copying the structure of an organisation many times its size.

The lesson for me was to build enough process to improve execution, not enough process to create the appearance of sophistication.

A good system should make the right action easier, make information more visible and reduce dependence on memory.

If the process creates work without improving a decision, I question why it exists.

Accountability

Advising a decision and carrying it are not the same experience.

During my advisory years, I worked with founders, C-suites and boards across a range of sectors.

That work taught me a great deal about strategy and implementation.

But building my own businesses changed my respect for the client side of those conversations.

It is one thing to recommend a restructuring, a new market, a change in operating model or a different allocation of resources.

It is another thing to make the decision when the employees, cash flow, clients and reputation are yours.

Entrepreneurship made me more conscious of the emotional cost of decisions.

That does not mean avoiding difficult calls.

It means understanding that the person making the call is often carrying more than the financial logic alone.

What changed most

Seven shifts in how I now think.

Risk

I became less interested in whether something could work and more interested in whether we could absorb it if it didn’t.

This may be the most important change.

Entrepreneurs are surrounded by possibility.

There is always another market, product, partnership, hire or investment that could work.

The question I ask more often now is what happens if it does not.

Can the business absorb the cost? Can we reverse the decision? Does it consume too much management attention? Does it create dependency? Does it narrow our options?

This is closely connected to how I think about risk more broadly, which I explored in What 20 Years in Finance Taught Me About Risk.

I am not trying to eliminate risk.

I am trying to make sure the risks we take are deliberate, understood and survivable.

What I kept from banking

I did not leave institutional finance behind. I took the useful parts with me.

I still value preparation.

I still value governance.

I still believe numbers should reconcile with the story being told.

I still believe reputation is an asset and that risk becomes more dangerous when nobody clearly owns it.

I still believe strong client relationships are built through consistency rather than performance theatre.

What changed was the way I apply those principles.

Entrepreneurship made me strip them back to their practical purpose.

What decision does this process improve? What risk does this control reduce? What outcome does this meeting create? What does this investment unlock?

If I cannot answer those questions, I become suspicious of the activity.

Final thought

The biggest shift was from managing within a system to building the system itself.

Investment banking taught me how complex organisations operate.

Investment management taught me that strong ideas still need strong platforms.

Advisory work taught me how difficult implementation can be.

Entrepreneurship brought all of those lessons together.

As a founder, you do not simply make decisions inside the machine.

You decide what the machine should be.

You decide how fast it moves, where it spends, what it measures, who it trusts, which risks it takes and what it refuses to compromise.

That responsibility has changed how I think more than the freedom ever did.

Use the decision process that fits the commitment

A reversible decision can often be tested within a small budget and a short period. An irreversible commitment needs a different standard of evidence. Signing a long lease, making a personal guarantee or hiring ahead of dependable revenue creates obligations that continue after the initial enthusiasm fades.

Write down what must be true for the decision to work, the evidence available today and the point at which you would stop or change direction. Assign a review date before making the commitment. This keeps speed connected to accountability and makes it harder to rewrite the original rationale after the result is known.