You Need to Be More Afraid of Wasting Your Life Than Embarrassing Yourself

“You need to be more afraid of wasting your life than embarrassing yourself.”

I have thought about this sentiment a lot recently because being a founder right now is fucking weird.

There has absolutely never been a better time in history to build something. There has also probably never been a worse time to expect anybody to care that you did.

AI has made building absurdly cheap. I can do things myself now that would have required an actual team a few years ago. Engineering, design, research, content, outbound, analysis. Whatever. Everyone else figured this out too.

So now there is just... a lot of stuff.

More software. More startups. More people building in public. More AI tools for building AI tools. More cold emails written by the same models to the same people. More founders explaining how they hit $1M ARR in 11 days. More advice. More launch videos. Much more noise.

You can spend six months obsessing over a problem and discover somebody recreated 80% of your product over the weekend because they saw a tweet about it.

This fucks with you.

I don’t mean competitively because competition is fine. I mean much deeper than that:

• You start asking whether any of this is actually durable.

• Why build this if the models will just do it?

• Why ship that feature if Anthropic or OpenAI can wipe it out in three months?

• Why start another SaaS company when software itself increasingly feels abundant?

• Why write when everyone is generating content?

• Why sell when everyone’s inbox is already full of AI generated bullshit?

And if you are actually trying to make a company work rather than cosplay as a founder there is another less philosophical question underneath all of this:

How the fuck are we going to make money and keep making money?

I feel this acutely.

We had real success early with SpecStory. A lot of people installed it. A lot of people used it. That felt incredible.

Then you learn the realest of lessons: people using something and people paying you enough money to build a company around it are not remotely the same thing.

We built Stoa. I thought there was something important there. We couldn’t make the market care enough.

I launched Hardcore Agentic Engineering on Maven and people paid for it immediately.

Now we’re building RunStory around something I believe very strongly: agents are going to do more and more of the actual implementation of software and the interesting and important problem becomes how the hell you confidently verify all of that work without sitting there reading every line yourself.

I believe it.

That doesn’t mean it works as a business yet.

You don’t get points for conviction.

Stripe does not accept conviction.

This is where being a founder gets hard in a way I don’t think I properly understood before doing it.

Every product is a little claim about reality.

You are saying: this problem exists. It matters. I understand something about it. I can build something people want. Eventually some (and hopefully many( of them will pay me.

Then reality gets to answer.

Sometimes reality answers very slowly.

That period in between can make you insane.

Especially right now because you are surrounded by what appears to be everyone else’s success.

• Someone raised $30M.

• Someone hit $10M ARR.

• Someone launched the thing you were thinking about.

• Someone has 100,000 GitHub stars.

• Someone you have never heard of posts a Stripe screenshot that looks like the GDP of a freaking island.

And you’re sitting in your office wondering why the button on your landing page isn’t converting.

I have had plenty of moments recently where I thought: what exactly am I doing?

I used to have an extremely good job.

There were many things I didn’t like about that life, but nobody looked at the results of a week and decided whether my entire existence made sense.

“You could leave life right now. Let that determine what you do and say and think.” — II. 11

Founding a company is different.

The work gets into your head because the feedback is so direct.

Nobody bought it.

They stopped using it.

They didn’t respond.

The launch went nowhere.

The competitor is growing faster.

You were wrong.

Or maybe you weren’t wrong and your message sucks.

Or your distribution sucks.

Or your product is too early.

Or the market just doesn’t care yet.

Good luck sleeping!

And yet...

I fucking love it.

I really do.

I have never felt more alive professionally than I have during the last two years.

There is something wonderful about having nowhere to hide.

You made the thing.

You put it in front of someone.

Did it work?

Did they care?

Would they pay?

No amount of strategy language can save you from the answer.

It is embarrassing sometimes.

Good.

Embarrassment is remarkably survivable.

This is something I did not understand when I was younger. I thought the risk was looking stupid. Failing publicly. Leaving a very successful career and having people wonder whether that was such a good idea after all.

That stuff barely matters.

Time matters.

I am 41 now.

The two years since I left my old life went insanely fast.

Another two will go just as fast.

Then five.

Then ten.

This changes my calculations.

Would I rather spend those years attempting things that might fail, occasionally getting my ass kicked, launching products nobody wants, changing my mind in public and feeling a little stupid?

Or would I rather protect the appearance that I could have done something interesting if I had really tried?

That second possibility scares me much more now.

The market is absolutely saturated.

AI is absolutely making it harder to stand out.

Most products probably are easier to copy.

Distribution is harder.

Buyers are exhausted.

A bunch of software businesses that looked wonderful five years ago probably aren’t wonderful businesses anymore.

All true.

Build anyway.

Not because everybody deserves to win.

You don’t.

Not because following your passion magically works out.

It often doesn’t.

And definitely not because failure is secretly success or whatever other bullshit people put on LinkedIn.

Build because this is your life.

If there is something you can’t stop thinking about, go find out.

Actually find out.

Make it. Sell it. Get rejected. Change it. Kill it if you have to. Start another one.

The reward isn’t that eventually the universe recognizes your bravery and deposits $10M into your bank account.

The reward is getting to spend some portion of your absurdly short time here completely engaged in something whose outcome you do not know.

That is rare.

And despite everything happening right now and how hard it can feel, I still can’t believe we get to do it.