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Welcome to the emotional whiplash of starting a business.

Matthew Webb·3 min read·Feb 2025

Nobody warns you about the strange parts of starting a business.

The least glamorous rite of passage

Insurance, for one. Who knew you needed so much insurance? Not me. But apparently you do, and so you spend an afternoon buying protection against things you genuinely hope never to use. It is the least glamorous rite of passage imaginable, and nobody puts it in the founder highlight reel.

Then there is the messaging. I have rewritten my website at least five times. Tweaked the logo. Changed the tagline. Refined my positioning more often than I can count. Why? Because when it is your own business, it is not a marketing task, it is personal. You want it to be right in a way that borders on the irrational. And here is the spoiler: it never feels finished. I am already planning the next change, because what I have still is not quite it.

The part no one prepares you for

But the real shock is the emotional whiplash.

One minute you are on top of the world, riding the high of a brilliant conversation, certain this is going to work. An hour later you are staring at a quiet inbox, convinced the whole thing is falling apart. Unstoppable and completely out of your depth, sometimes in the same morning. That swing is not a sign you are doing it wrong. It is the tax you pay for caring this much about something you built yourself.

What I would tell a new founder

So if you are thinking about starting your own thing, here is what I would tell you:

  • The first weeks are the hardest: the highs are unreal and the lows are brutal. Expect both. Ride them out. They level off.
  • It will not be perfect, so launch anyway: perfect is a moving target you will never hit from the sidelines. Ship it, learn, and refine in public.
  • You will deal with things you never imagined: accountants, insurance, tax returns, and a hundred small admin jobs nobody mentions. It comes with the territory.

I am writing this having just started my first venture, and I can already tell the journey will look nothing like I pictured. To everyone who has built something from nothing and come out the other side: I see now what it took, and I take my hat off to you.

What is your most ridiculous "I genuinely did not sign up for this" moment as a founder?

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