Bootstrapping Into the AI Wave

by | May 20, 2025

Software startup founders and SaaS CEOs have always been partly crazy and partly realistic, and we get to choose the mix. This abnormal dualism is needed more than ever as AI rushes into our businesses and products.

I have been in the software product and startup game for a long time. I have seen the change to PCs, from DOS to Windows, to Windows 95, to client-server, to Web 1.0 and Web 2.0, with mobile, social, global, the cloud, and SaaS.

Those shifts were not trivial. They required extreme realism, small bets before big bets, and great timing to surf the next wave and avoid crashing on the rocks.

You bet your company when you made the shift to the next technology wave.

Some made it to the other side, and many didn’t.

There is a lot of AI hype, but this shift will surely be one of the biggest technology waves ever.

We don’t know how quickly it’s coming and or exactly what it will look like in a couple of years.

For CEOs of existing early-stage B2B SaaS companies, you need to find the right mix and timing with:

1) Practical realism to see the AI threats and opportunities for what they are right now.

With all the hype and massive changes coming quickly, this is harder than it looks.

2) Great timing to not be too early or too late for your customers in your market relative to your competitors.

Looking back, this is why most software companies didn’t make it to the next technology wave.

3) Crazy stubbornness about your vision and solving a big problem for customers you care about.

At the same time, there is an unusual level of openness to learning and change for the few big things that need to move in your business.

These are all harder than they look.

Many entrepreneurs get it backward. They get stubborn about the How and flaky about their big vision and their Why.

That doesn’t work too well when markets move and technologies shift.

You used to need to raise a lot of investor money to fund your shift to the new platform, but big funding isn’t the answer anymore.

The right mix of crazy and practical is required, which is usually easier to do without investors and a gun to your head.

That’s how I see it. How do you see it?

Greg Head posted this on LinkedIn on May 20, 2025.

Check out the comments and join the discussion on LinkedIn.

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