I have started six companies over the past 30 years. There was one common thread before starting each one. I would feel a familiar pit in my stomach, a fear of not knowing what I was getting into.

You would think that after doing it once or twice, that fear would fade. It never did.

Part of it was the obvious fear of failure. But a lot of it was something more basic. Starting a company meant signing myself up to do a bunch of really hard things I had absolutely no idea how to handle, with no guarantee that all of the hard work and resilience would pay off.

Each company came with a completely different set of problems. Over time, through multiple startups and experience over the years, I found ways to quiet that inner voice that always asked, ‘Can I really figure this out?’

While I knew success was never guaranteed, I definitely built a tolerance for risk and became more accepting of the uncertainty that I knew would come. Looking back, perhaps that fear and struggle weren’t weaknesses, but rather part of my personal development as a founder.

A New Generation Of Entrepreneurs

Now, a new generation of entrepreneurs is emerging.

In less than three years, AI has removed many of the hurdles and unknowns that come with starting a company. It has pretty much democratized entrepreneurship. A recent Harvard Business Review article described AI as increasingly “commoditizing execution,” allowing people with little technical expertise to build functional products and making solo founding more viable and easy to do.

This is a good thing. Even though the pace of AI’s growth can be intimidating, we should celebrate what it has made possible. Today’s entrepreneurs can launch startups faster and cheaper, and get to a surprisingly solid first version with far fewer people, fewer hurdles and way less capital.

Today’s founders have capabilities I couldn’t have imagined 30 years ago, let alone five years ago.

Why AI Shouldn’t Solve Everything

But here’s where things get interesting.

What happens when starting a business becomes so much easier and most of the usual operational hurdles disappear?

For most of my 30-year entrepreneurial career, friction was just something I wanted to eliminate. How would I raise enough money? Who should I hire? How were we going to build this? And when things inevitably went wrong, how would we fix them?

If you had given me today’s AI tools 30 years ago, I would have gladly taken every single one of them.

But now, looking back, I’m beginning to wonder whether some of that friction served another purpose.

Some friction simply slowed us down. But other friction forced us to develop skills we didn’t have. Limited capital forced resourcefulness. Not knowing how to solve a problem forced creativity. Rejection forced you to get better at selling. Failure forced you to adapt. And uncertainty forced you to make decisions without knowing whether you were right.

Maybe there is a difference between unnecessary friction and what I would call productive friction, the type of friction that actually helps you grow.

If AI continues to remove productive friction, there is a question worth asking: Are we just making it easier to build companies, or are we also losing the experiences that ultimately shape an entrepreneur’s DNA?

There are already early signs that this tradeoff is worth paying attention to. Researchers from Microsoft and Carnegie Mellon studied 319 knowledge workers and 936 real-world examples of how they used generative AI. They found that greater confidence in AI was associated with less critical thinking, while greater confidence in one’s own ability was associated with more critical thinking.

That finding might sound obvious, but I don’t think it can be emphasized enough. Critical thinking is a hugely important part of being an entrepreneur. So much of the job is solving problems without clear answers, usually with limited information and often while something important is at stake.

That brings me back to the fear I mentioned earlier.

Sometimes I wonder if the ‘fear gene’ that shaped me as an entrepreneur is still being exercised today. But maybe that’s not a fair question. I don’t think today’s founders are less resilient or less willing to take on tough challenges. What’s different is the environment they’re working in.

When I didn’t know how to do something, I often had no choice but to wrestle with it until I figured it out. Sometimes I got it right. Plenty of times I got it wrong. But going through that process over and over again built my confidence, judgment and resilience.

AI can now help a founder find answers much faster. That’s a huge advantage. But faster access to an answer shouldn’t completely replace the experience of figuring things out on your own.

Because resilience isn’t something you can prompt your way into. Neither is conviction, judgment or the confidence that comes from getting something wrong, picking yourself back up and eventually figuring it out.

The solution isn’t to make entrepreneurship harder again. It’s about knowing which hard parts are worth keeping.

The Things AI Can’t Teach Founders

So what does this mean for today’s founders?

I don’t think the answer is to use less AI. I use it every day and believe entrepreneurs should take advantage of every tool available to move faster, operate leaner and focus on things that actually matter.

AI can already help you write code, analyze markets, build prototypes or review your pitch, and those capabilities are only going to get better. It can probably even tell you how the most resilient founders behave when things go wrong.

But it can’t teach you resilience.

It can’t show you what it feels like when your biggest customer tells you they’re leaving or when you’re trying to figure out how you’re going to make payroll with money running out. AI can help you think through a difficult decision, but it can’t make them for you especially when that decision means firing someone you care about or continuing to believe in something when everyone around you thinks you’re wrong.

You have to live through those experiences. This is why I believe founders should be intentional about how they use these tools. AI can help you prepare for a difficult sales meeting, but you still need to get into the room and hear ‘no’. It can analyze thousands of customer feedback, but that shouldn’t replace actually talking to your customers. And while it can give you a well-reasoned answer to a difficult problem, there is a big difference between getting the answer and developing the judgment to know whether it’s the right one.

I’m saying all this because AI will never be worse than it is today. These tools are going to keep getting better, and founders will naturally rely on them to do more. My concern is that as this happens, the line between unnecessary friction and productive friction will become harder to see. We may increasingly outsource not just the work, but some of the critical thinking and experiences that historically helped entrepreneurs develop judgment, resilience and confidence.

As AI gets better, the easier it will be to get to an answer without going through the process that teaches you important lessons.

Maybe that’s the balance we should be looking for: Use AI to accelerate the experience, not replace the experience.

Let it remove the repetitive work and help you get to better answers faster, but don’t use it to avoid the uncomfortable conversations, difficult decisions and problems that force you to think for yourself. Those are often the experiences that build resilience, judgment and conviction, along with some of the scar tissue that I think every entrepreneur needs.

As these tools get better, founders should ask themselves a simple question: Am I eliminating work, or am I eliminating learning?

The Founder Still Matters

For most of my career, I would have done almost anything to make entrepreneurship a little easier. Looking back now, I’m starting to realize that some of the things I wanted to eliminate may have been the things that taught me the most.

I don’t love the sleepless nights, the mistakes or that pit in my stomach. And I certainly wouldn’t suggest that today’s founders intentionally make things harder just for the sake of it. But I do believe there is value in recognizing that building a company has always been about more than just the company itself.

AI will keep getting better at helping us build, and that should make this one of the most exciting times in history to become an entrepreneur. But the parts of the journey that develop judgment, conviction and resilience still belong to us.

After 30 years, I think that’s what I’ve come to appreciate the most. I spent a lot of that time thinking I was simply building companies. Now I know each of those companies and the adversity I faced while building them helped make me the entrepreneur and the person I am today.

And as AI makes starting a business easier and faster than most of us realize, maybe that’s even more reason to hold on to the parts of the journey that help us grow.

1. https://hbr.org/2026/08/ai-makes-building-easy-choosing-what-to-build-is-harder

2. https://www.microsoft.com/en-us/research/publication/the-impact-of-generative-ai-on-critical-thinking-self-reported-reductions-in-cognitive-effort-and-confidence-effects-from-a-survey-of-knowledge-workers/