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The hardest part of building something is overcoming the embarrassment of trying

There is a particular kind of embarrassment that comes with trying to build something before there is any evidence that it is going to work.

I have spent the past while building Chinwag, a marketplace for paid one-to-one video conversations. The product is live, the technical work is largely complete, and I have now reached the stage where progress depends much less on building and much more on persuading real people to use it.

That transition has been more uncomfortable than I expected.

When nobody has signed up yet, the weeks are passing, and the scale of the task is becoming clearer, it is difficult to project unwavering founder confidence. You are asking people to believe in something whose current lack of traction is plainly visible.

There is also something culturally uncomfortable about openly promoting your own idea. I am Irish, and we are often much more comfortable criticising ambition than encouraging it. I have certainly been guilty of that myself in the past. It is easy to be sceptical when somebody else puts themselves forward. It feels very different when you are the person asking others to take the idea seriously.

Chinwag is a marketplace, so its earliest progress depends heavily on people being willing to join before there is much activity already there. That means approaching friends, former colleagues and people in my wider network and asking them to create profiles, test the platform and give honest feedback.

They are an invaluable resource, and I am fortunate that some of them are willing to help. But I still find the process strangely uncomfortable.

These are people I have known for years. I do not want every conversation to become a sales opportunity. I do not want friendship to feel transactional. And whenever I find myself explaining the vision or encouraging someone to sign up, a small part of me wonders whether I sound persistent and committed—or simply slippery and self-interested.

Intellectually, I know that this is probably unavoidable. Nobody else is going to create the first momentum for the business. Early-stage founders cannot outsource belief in their own product.

But emotionally, there is still a gap between knowing that promotion is necessary and feeling comfortable doing it.

Perhaps that is one of the less-discussed challenges of starting something. Before you overcome product risk, market risk or financial risk, you first have to overcome the social risk of being seen trying...and possibly failing.

For those who have built something from nothing: did you find this stage difficult?

How did you ask friends, colleagues and early users for support without feeling as though you were constantly selling to them?

And did the embarrassment eventually disappear, or did you simply learn to act despite it?

on August 4, 2026
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    The shift from building to asking people to participate is a very different kind of uncertainty.

    It’s no longer about whether the product works, but about being willing to expose it before the evidence exists.