AI, Automation & the Human Advantage: What a 30-Year Tech Veteran Wants You to Know
There is a race happening right now in tech, in e-commerce, in fashion, in almost every industry you can think of. And according to Liza Day, founder of The Cut Design Academy, it’s a race to the bottom.
Making The Cut with Liza Day and Tom Jensen
In the latest episode of Making the Cut, Liza sits down with Tom Jensen, founder of Chocolate Pocket Development and a software developer with over 30 years of experience building web, mobile, and AI applications for startups and Fortune 500 companies alike. What follows is one of the most honest conversations about AI you’ll hear, no hype, no fear-mongering, just two people who’ve built real things talking about what’s actually changing and what isn’t.
From Atari to AI: How Tom Got Here
Tom’s story starts in 1979, when his father handed him an Atari 800 and told him to learn how to program. “This is the future,” his dad said. Turns out he was right.
From there, Tom taught himself through books on subway rides in New York, talked his way into jobs he was barely qualified for, and built a career spanning the dot-com boom, the crash of 2001, the rise of mobile, and now the AI revolution. He’s seen every major shift in tech from the inside.
His company, Chocolate Pocket Development, now focuses heavily on AI-driven applications, and he has a clear-eyed view of where things are heading.
The Race to the Bottom
Liza draws a direct parallel between what happened to her manufacturing business when trade quotas were removed in the late 1990s and what she sees happening now with AI.
“The race to the bottom was swift,” she says. “My clients were leaving for 15 cents. If you can’t do it for 25 cents less, I’m going down the street.”
She sees the same pattern emerging with AI. Businesses are cutting graphic designers, developers, copywriters, project managers, and anyone they think an AI tool can replace. But Liza isn’t buying it entirely.
“I’d still pay Andy, my graphic designer, because he’s got the graphic design mind. I don’t understand user experience the way he does. That user experience my customer is going to have is what’s going to make them come back. I don’t want to risk that on AI yet.”
The point isn’t that AI is bad. The point is that the race to eliminate human expertise as fast as possible is a slippery slope, and one we’ve seen before.
What AI Actually Does Well
Tom is pragmatic about AI’s capabilities. It’s exceptional at writing and understanding code, which makes it a powerful tool for developers. It can dramatically speed up tasks that used to take hours. But it scrapes the internet for its answers, which means it can be wrong confidently.
“It doesn’t necessarily tell you what is actual,” Liza notes. “Sometimes when you put stuff in there, it’s not always right.”
The key, both agree, is knowing enough to verify what AI gives you. The people who will thrive aren’t the ones who hand everything to AI blindly; they’re the ones who understand the machinery well enough to manage it.
The Career Nobody Is Talking About
Liza makes a prediction that deserves more attention: creative project management is going to be one of the most lucrative careers of the next decade, across every industry.
Think about it. As AI tools multiply, someone has to know which tools to use, how to prompt them effectively, how to quality-check the output, and how to bring it all together into something coherent and on-brand. That’s not a technical skill alone. That’s a creative, strategic, human skill.
“If it’s something that really gets your blood going,” Liza says, “you could be a pioneer. You’re on a horse that is already galloping.”
How to Get Started
Tom’s advice for anyone wanting to get into tech or AI is straightforward, start with accessible, credible learning resources:
Khan Academy — free, solid fundamentals
Google’s online learning programs — growing rapidly
Part-time college courses — great for getting your sea legs without committing to a full degree
General Assembly — Liza’s personal recommendation for short, career-focused courses. She’s seen it triple someone’s earnings firsthand.
The message is consistent: you don’t need a degree. Tom didn’t have one when he started. What you need is curiosity, persistence, and the willingness to keep learning.
The Bottom Line
AI is not going away. The landscape is changing faster than most of us can track. But the human advantage, judgment, creativity, experience, the ability to build relationships and understand context that isn’t going away either.
The question isn’t whether to engage with AI. It’s whether you’re going to be someone who uses it well, or someone who gets replaced by someone who does.
As Tom puts it, the people managing and working with AI are the ones shaping what comes next. That’s where you want to be.
Listen to the full episode of Making the Cut, AI, Automation & the Human Advantage — now on Spotify and YouTube.
Tom Jensen is the founder of Chocolate Pocket Development. Learn more at chocolatepocket.net