Inside Aaron Levie’s AI Playbook: What Every Entrepreneur Can Learn from Box’s “AI-First” Shift

In an era where many companies still debate the merits of AI, Aaron Levie is already ten steps ahead. The co-founder and CEO of Box is not only transforming his cloud content platform into an AI-powered intelligence engine, he’s offering a roadmap for how enterprises (and entrepreneurs) can do the same.

Appearing on the Rapid Response podcast with Bob Safian, Levie painted a vivid picture of AI’s breakneck acceleration, the dawn of intelligent agents, and why true AI transformation is about unleashing new capabilities you never had time or budget for before.

“This is the fastest I’ve ever seen tech move… by 5 to 10X.”

Levie isn’t one for hyperbole, but even he sounded awestruck by the velocity of AI development. From weekend Slack explosions over surprise model releases to 10PM group chats filled with “AI friends,” Levie described a world where staying relevant means being perpetually wired in.

And it’s not just about speed—it’s about vision. “Our ChatGPT moment came when we realized we could finally talk to our unstructured data,” Levie said, referencing contracts, invoices, and marketing assets stored in Box. “Now, we’re building AI agents to act on that data asking questions, checking answers, applying judgment.”

The Rise of AI Agents: “This isn’t just automation. It’s augmentation.”

Levie is particularly bullish on AI agents, multi-step, tool-using systems that mimic how humans work. He likens this shift to the evolution from instant AI chat answers to deep research capabilities. “I want to know the pricing strategy of 100 competitors. Today, AI gets me a research report in 15 minutes at midnight.”

These aren’t theoretical use cases. Box’s new AI Studio lets customers build their own agents. The result? “We’re hearing ideas from customers we never whiteboarded,” Levie said. And notably, 80% of the use cases involve work that wasn’t done before. “Not because we didn’t want to, but because we couldn’t afford it.”

This, he emphasized, is the hidden promise of AI in business: enabling projects that were once impossible or uneconomical.

AI-First Culture: “If you can prove AI helps, that’s when you get more headcount.”

Unlike Duolingo or Shopify, which require staff to justify non-AI methods, Box flips the script. Levie’s model: reward teams who do leverage AI with more resources. “We want dollars going to the highest ROI areas, and those will be the ones accelerating because of AI.”

He also warns against common traps, like confusing AI adoption with job cuts. In his view, the productivity gains from AI should be reinvested to drive faster growth, not banked as margin. “If a sales rep can sell 5% more thanks to AI, we’ll reinvest that to grow faster, not cut costs.”

Why the “AI Hype” Complaints Are Misguided

Levie rejects the notion that AI hasn’t lived up to its business promise. “Look at Cursor—arguably the fastest-growing enterprise software company in history—because of AI agents that help you code.”

He sees early movers in marketing (like Windsurf) and design (like Figma) already benefiting. The lag? It’s a rollout curve, not a failure. “GitHub Copilot preceded chatGPT by two years. The same thing is happening now with AI agents, they’re just ahead of the curve.”

A Decade of Change in 12 Months?

Looking ahead, Levie predicts the next wave is about widespread agent adoption. “We’re at the start of a decade-long enterprise AI journey. But this year? This is when agents go mainstream.”

And for startups, the advice is clear: don’t wait. “You want your organization running more AI experiments, faster, than your competitors. That’s how you stay ahead.”

Levie’s Advice to Entrepreneurs:

• Start small, but start now: Use AI to solve one frustrating bottleneck in your business. It doesn’t have to be perfect.
• Measure speed, not just savings: AI is a force multiplier. Look at how much faster you can move through decisions and actions.
• Let AI expand your ambition: Don’t just automate old tasks, dream up the ones you couldn’t afford before.

Aaron Levie doesn’t just see AI as a tool. He sees it as a mindset. One that will divide the companies that thrive from those that fall behind.

“Technology’s a gift,” he said. “If you’re energized by it, you’ll stay ahead. If it drains you, you’ll get left behind.”

It’s a wake-up call. For CEOs. For founders. For anyone who’s ever said “we’ll look into AI later.”

Later is already here.