The Many Hats Hypothesis

There’s a seductive vision of entrepreneurship that goes something like this: you have the idea, you assemble the team, you manage the strategy, and other people handle the details. You’re the visionary. The CEO. The person who sees the big picture while others execute. This is how you build a company you don’t understand.

The founders I know who’ve built something real—something that actually works, that they actually control, that they can actually manage—took a different path. They did everything themselves. Not forever. But first.

The Case for Doing It All

When you do a job yourself, you learn things you can’t learn any other way.

The Insulation Problem

When someone else handles a function—accounting, customer service, operations, whatever—you get reports. Summaries. Filtered information. The raw experience becomes processed data by the time it reaches you.

This isn’t necessarily bad. You can’t do everything forever. Delegation is essential for growth.

But if you delegate before you understand, you’re building on a foundation you can’t see. You’re trusting that the processed data accurately represents reality. And often, it doesn’t.

The Customer Contact Imperative

This matters especially with customers.

When you’re the one answering support tickets, you hear things directly. Not summarized in a weekly report. Not aggregated into trends. The raw, unfiltered experience of someone trying to use what you’ve built.

You hear the frustration. You see the confusion. You understand the gap between what you thought you were offering and what they actually experienced. This feedback is gold—the most direct signal you can get about whether your business is working.

I’ve watched founders become completely disconnected from their customers. They look at NPS scores and churn rates—lagging indicators, abstractions. Meanwhile, their support team has been fielding the same complaint for months, but it never bubbled up because it didn’t fit neatly into a report category.

Do your own support. At least some of it. At least sometimes. The direct contact is irreplaceable.

The Books Don’t Lie

The same principle applies to your finances.

When you’re the one doing the books—categorizing expenses, reconciling accounts, tracking cash flow—you see where the money actually goes. Not a summary someone else prepared. The actual line items. The actual patterns.

This is uncomfortable. Sometimes what you see isn’t what you want to see. But that discomfort is information.

The classic small business failure mode is the owner who “doesn’t have time” for the financial details. They hire a bookkeeper, maybe an accountant, and they look at the summary reports. Revenue is up. Expenses seem reasonable. Everything’s fine.

Then it isn’t. The bookkeeper was making categorization decisions the owner didn’t understand. The accountant was optimizing for taxes, not cash flow. The “reasonable” expenses included things the owner would have cut if they’d noticed. And sometimes—this happens more than people admit—someone was stealing.

The Business Plan Exercise

People push back on this. “Why should I do all these things myself when I could hire someone better at them?”

It’s the same objection people raise about business plans. Why build financial projections when every number is going to be wrong? Why map out a detailed plan when reality will force you to change it?

The answer is the same in both cases: the point isn’t the output. The point is what you learn by doing it.

When you build a financial model for your business, you’re not predicting the future. You’re understanding relationships. You’re learning that if this number changes, that number has to change too. You’re discovering the unit economics that spell profitability versus the ones that spell doom.

The model will be wrong. Every number you put in will be wrong. But you’ll understand the machine. You’ll know the inputs and outputs. You’ll know what has to be true for this to work.

Doing every job yourself teaches you the same thing about your operations.

The Hiring Advantage

Here’s the practical payoff: when you hire for a role you’ve done yourself, you’re operating from a completely different position.

This advantage compounds. Every role you’ve done yourself is a role you can hire for effectively. Over time, you build an organization where you genuinely understand every function—because you’ve done every function.

Company of One Is More Possible Than Ever

The tools available now make this more achievable than at any point in history.

Accounting software that handles complexity you used to need a bookkeeper for. Customer service platforms that one person can manage efficiently. AI tools that augment your capabilities across every function. No-code tools that let you build things that used to require developers.

The Real Point

Let me be direct about what this is and isn’t.

It’s not about proving something. You don’t need to do everything yourself to earn legitimacy as a founder.

It’s not about saving money. Sometimes hiring is the smart financial move, even early.

It’s about learning. Understanding your business at a level you can only achieve through direct experience.

A business is a machine. Inputs lead to outputs through a series of transformations. Money comes in, products or services go out, customers are acquired and served, operations happen.

You can manage this machine from the outside, looking at dashboards and reports. But if you want to truly understand it—if you want to know why it works when it works and what’s breaking when it breaks—you need to have operated each part yourself.

The Long-Term Return

This investment pays off for years.

When problems arise, you have intuition about where to look. When opportunities appear, you understand whether you can actually execute on them. When people give you advice, you can evaluate it against your own experience instead of just trusting that they know your business better than you do.

You become harder to fool, harder to mislead, harder to surprise. Not because you’re paranoid, but because you understand the territory from having walked every part of it.

This is what it means to really run a business. Not to own one, not to manage one, but to run one. To know it so well that you can see the problems before they become crises and the opportunities before they become obvious.

The path to that knowledge is through the work. All of it. At least once. At least at first.

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There’s no shortcut to understanding your business. Reports and dashboards can tell you what’s happening, but only direct experience teaches you why. The founders who do every job themselves—not forever, but first—build a foundation of understanding that pays dividends for as long as they run the company. It’s harder than delegating. It’s also how you learn what you actually need to know.