Don Finley: How Can AI Make Work Feel Like Play?

Don Finley is a seasoned innovator, founder and CEO of FINdustries, with a decade of experience in artificial intelligence, holding a computer science degree from the early days of AI’s “winter,” when the math was ready but the tech wasn’t. We spoke about the transformative wave of AI sweeping through businesses, how it’s reshaping work, and why it’s a rare opportunity—akin to the dot-com boom or social media revolution—to ride rather than resist. “You can either get crushed by the wave of AI or you can learn to ride it,” he says, framing the stakes perfectly.

The conversation zeros in on practical AI integration, from a “crawl, walk, run” approach—starting with treating AI as a team member, then building tools that know your brand, to finally handing off outcomes to AI agents. Don shares a jaw-dropping example: a 20-page market analysis for his real estate business, churned out by AI in 30 minutes, that once took weeks. “That would have taken a lot of back and forth, some drafts… but in 30 minutes, my partners and I were able to digest one of these reports.” It’s not just efficiency; it’s about freeing up space for what matters—relationships, strategy, and creativity, the trio he believes AI shouldn’t touch.

What’s most striking is Don’s vision of work as play, inspired by Alan Watts: “The goal in life is to make your work look like play and so that nobody knows that you’re working.” AI, he argues, can strip away the mundane—think customer service bots or automated sales research—so you’re left with the fun stuff: connecting with people, dreaming up strategies, and chasing creative sparks. Yet, he’s candid about the flip side, noting how AI’s rise has slashed freelance jobs in writing and coding by up to 20% in a year.

There’s a personal thread here, too. Don’s trek up Kilimanjaro revealed a deeper truth: “I’m the reason for my own dissatisfaction… That sunrise and all the people that I dearly love are on this journey with me and I can’t find a way to enjoy it.” It’s a raw moment that ties his entrepreneurial drive to a quest for purpose—one AI can support but never define. He sees entrepreneurship as “the best reflection of my own internal state,” a mirror that AI can polish but not replace.

Takeaways:

• AI’s a wave worth riding—think of it as a teammate, not a threat, and start small.
• It can slash grunt work (e.g., a month-long project down to hours), letting you focus on the human stuff.
• White-collar jobs are shifting—copywriting and coding gigs are down, but individual output is soaring.
• Purpose matters more than ever; as Don puts it, “It’s more important that you understand at the core level what drives you.”
• AI won’t save you from yourself—use it to amplify, not escape, your unique value.

Rethinking work, joy, and thriving in an AI-driven world goes beyond just tech. Don’s blend of practical know-how and soul-searching makes it a must-listen.