I’ve spent my career building technology. Now I’m questioning the rules we’ve built around it.

I’m Jake Woodward.

For more than 25 years, I’ve worked inside the technology industry. I’ve founded and sold a business, held senior executive positions, led product and engineering organizations, and helped companies build and scale products used by real people.

I’ve seen technology from just about every angle. As the person building it, the executive responsible for it, the entrepreneur betting on it, and the customer trying to make it actually work.

I’ve also lived through enough technological change to know that the biggest consequences often aren’t the ones we initially expect.

Then AI changed the equation.

Over the past two years, I’ve spent more than 3,000 hours building software with modern AI tools.

That experience has fundamentally changed how I think about what’s possible, especially when it comes to who gets to build technology, what it costs, and how much power individuals and small businesses can have.

But it’s also raised some much bigger questions.

What happens to the value of expertise when knowledge becomes widely accessible? What happens to careers when software starts performing the work rather than helping us perform it? What happens to economic opportunity when the traditional paths to a stable life stop working the way they used to?

And perhaps most importantly, who gets to make the decisions that will shape what comes next?

Today, I’m also an educator.

I’m a member of the founding faculty at the Buffalo campus of Golisano Institute for Business & Entrepreneurship, where I help students understand and work with AI.

Teaching has added another dimension to how I see this moment.

It’s one thing to experience a technological revolution midway through your career. It’s another to look at the students entering the workforce and wonder what kind of world we’re actually preparing them for.

I don’t believe preparing people for the future simply means teaching them how to use today’s tools.

It means helping them learn to question assumptions, think critically, adapt, and recognize opportunities that previous generations couldn’t have imagined.

And it means being willing to confront some uncomfortable possibilities about what comes next.

Why The Great Reversal?

I started this publication because I think we’re having too many conversations about what AI can do and not nearly enough about what it means.

Technology is changing the economics of software, the value of expertise, the nature of employment, and potentially the foundations of economic opportunity itself.

Some of these changes could create a more accessible, equitable world. Others could deepen the divide between those who control technology and those whose lives are shaped by it.

I see tremendous reasons for optimism. I also see reasons for genuine concern.

And I don’t think either side of that conversation deserves to be ignored.

I want The Great Reversal to be a place where we challenge conventional wisdom, examine what is actually happening, and explore the implications without pretending the answers are simple.

I’ll share what I’m seeing firsthand, what I believe is coming, and where I think the conventional thinking gets it wrong.

I’ll also tell you when I’m uncertain, because anyone claiming to know exactly how this all plays out probably isn’t asking enough questions.

The rules are changing. I want us to understand those changes while we still have a chance to influence what comes next.

That’s what The Great Reversal is about.

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