The pre-AI founder vs. the post-AI founder

What got easier, what got harder, and what I’m still figuring out as we build in the AI wave.

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Hey folks. I’m sure, like many of you, AI has crept into my workflow to the point where I almost forget what it was like before it.

But I’ve been thinking about it lately because I founded a company pre-AI (Iteratively, acquired by Amplitude in 2021), and I’m building one now in the middle of this wave. The contrast is hard to ignore.

Here’s what I’ve noticed:

Building got easier, distribution got harder

Pre-AI, starting a company was just harder. A good idea wasn’t enough. Getting something into customers’ hands took longer, required more people, and burned more runway before you learned anything.

Now you can get an MVP out the door in a fraction of the time.

That sounds like a win, and it is. But it changes the game. Because if building gets easier, more things get built. More things get built, more noise gets created. More noise makes it harder to stand out.

The first question still matters: are you building the right thing? Now a second question runs right alongside it: can anyone tell what it is and why it matters?

This is less of a product question and more of a positioning question. And it’s harder than it looks.

In a crowded market like CRM, you feel this immediately. You have to be ruthlessly crisp about what you’re solving, for whom, and why you’re the right answer. Not in a branding exercise way. In a “can you explain it in one sentence to a skeptical buyer” way.

I can do more now, but it doesn’t feel easier

I didn’t expect this one.

I was talking to my wife about this recently. I asked her: am I more stressed now than I was in 2020? Is my anxiety higher or lower?

She didn’t hesitate. “You were stressed out back then too. It was hard.”

She’s right. The effort hasn’t changed. If anything, there’s less downtime now than there used to be.

What has changed is output. I’m probably doing two to three times the volume of work I was doing back then. The tools give you real leverage.

So the difference isn’t that things are easier. It’s that AI lets you do more. Then you have to decide what to do with that.

That decision is the hard part.

Hiring and org design are open questions

The old way of building SaaS companies came with a pretty standard playbook: hire engineers to build the product, hire a GTM team to help the world learn about it, scale headcount in a roughly linear way, hire managers, and build a hierarchy.

I’m not sure that’s right anymore.

Do you want managers managing people, or people managing agents? Do you hire for experience or AI literacy? What does “AI-native” actually mean in practice? If someone isn’t willing to embrace these tools, are they the right fit for the company you’re trying to build?

Any way you shape it, orgs will become more “fluid” as Dharmesh articulated here a year ago.

And more practically: what skills are going to matter a year from now, two years from now, three years from now? What should we be training on internally?

Honest answer: I don’t know yet. I’ll let you know when I do.

Company shapes are going to be more extreme

I also think we’re heading toward a world where startups are either:

• really small teams doing a lot with very few people, with high revenue per employee, or

• really big swings going after ambitious problems and trying to build the next generation of big companies in this era.

Everything in the middle feels like it’s getting squeezed.

Part of that is just how crowded SaaS is getting. Part of it is that the “old math” of operating a company is changing, and the “old math” of investing is changing too.

VCs are all over the board on what they’re looking for. We’re all still trying to figure it out.

If you’re building today, a few things feel true to me:

1. Building fast is not the advantage anymore. A lot of people can build fast.

2. Being right about the problem matters more than ever.

3. Being clear about what you do and who it’s for matters more than ever.

4. Your approach to hiring probably needs to change because the tools changed.

In the end, I don’t have a clear answer on which way was better or worse. It’s just different now. It’s easier to ship, harder to stand out, and there’s less of a playbook than there used to be.

But we’re all figuring it out together — which, honestly, is one of the things I like most about being a founder right now.

For founders that have gone on this journey before AI and with AI, would love to hear in the comments what has changed for you.

Until next week,

Patrick

Additional reads

1. The agentic organization - McKinsey

2. Lenny’s podcast with Brian Halligan - Why it’s never been easier to start a company, and never been harder to scale one