The Role of Reinvention: VC Veterans Share Why Now Is the Time to Break Things

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March 18, 2025

The Role of Reinvention: VC Veterans Share Why Now Is the Time to Break Things

Venture capital veterans Joel Cutler (co-founder and managing director, General Catalyst) and Paul English (co-founder, KAYAK and Boston Venture Studio) took the INBOUND 2024 stage to break down what AI really means for startups and businesses today: companies that hesitate to adapt are setting themselves up to fail.

With Harvard Business School professor Youngme Moon steering the conversation, they encouraged business leaders to rethink their approach before it's too late.

THE NEW TOOLS ARE ALREADY HERE

"Every once in a while new sets of tools come around that make doing something really provocative possible. Today is the day," Cutler declared early in the conversation. The message was unmistakable: AI is a fundamental shift in what's possible.

The barriers to innovation have dramatically lowered. You no longer need to build foundational technology; instead, you can focus on applying existing tools in ways that transform customer experiences.

"Now is the time where you can really do extraordinary work and the tools are available. You don't have to go out and create the tools," emphasized Cutler. "That's really the big moment that's changed between today and five years ago."

While larger platforms might move cautiously, virtually every other consumer-facing business is vulnerable to AI-powered disruption.

"Every consumer brand is going to be redone," Cutler predicted. "Most of the brands are either going to have to change dramatically or there's going to be a startup that eats their lunch."

Cutler's advice? Don't defend what exists; envision what could be. Don’t wait for technology to mature or become more accessible. The tools are already here and the only question is whether you'll use them before your competitors do.

SMALL TEAMS, MASSIVE IMPACT

If there was one stat that captured the room's attention, it was when Paul English casually dropped his new metric for the AI era: "millions of users per engineer."

English, who founded KAYAK and took it public with just 200 employees generating $300 million in revenue, sees AI completely changing up fundamental economics of building companies.

"I would rather a three-person team that's AI-powered than a 30-person team that's not," English stated, making it clear that the future belongs to lena, AI-first teams. His current venture, Boston Venture Studio, is pushing this efficiency further, focusing on metrics like "millions of users per engineer" rather than traditional scaling benchmarks.

From product development to customer service, English's companies are integrating AI into every corner of their operations. The result? Dramatically smaller teams producing dramatically bigger results.

AI is helping to create more nimble teams and scaling impact despite their size. This will create competitive advantages for organizations willing to rethink their operating models from the ground up.

GETTING OVER THE FEAR HURDLE

Cutler and English kept coming back to one important point: the biggest barrier to AI use for companies isn't technology or budget, but fear.

"You have to abandon fear of change today or you're screwed," Cutler put it bluntly.

Moon took it a step further noting that innovation is often blocked not by a lack of curiosity, but by insecurity: "I actually think there are more people out there that are curious and want to be innovators than manifest as innovators and curious people because there's something in them that is holding them back."

For organizations serious about leading, this means creating environments where experimentation is expected. "Take a risk, break some stuff, be provocative," urged Cutler. Companies that create fearless cultures will consistently outmaneuver those who aren’t willing to risk.

WHEN LEADERSHIP MAKES ALL THE DIFFERENCE

Unsurprisingly, both investors pointed to leadership as the ultimate differentiator in times of massive transformation.

Anytime I see the leader of a large company that's willing to say crazy things and change things in a big way, that's a company I want to follow.

Cutler built on this, highlighting how founder-led companies often have advantages in periods of rapid change. What sets these leaders apart? "Arrogance, smarts, energy, integrity... incredible curiosity, the willingness to be thinking about new stuff all the time. Forget about everything in the past," he said.

In times of technological upheaval, leadership matters more than ever and those who have the vision to reimagine what's possible will be at the front of pack.

GETTING STARTED WITH AI REINVENTION

Ready to put these insights into action? Here are concrete steps recommended by Cutler and English:

Start using AI personally: As English demonstrated, personal experimentation is the fastest way to understand AI's potential. Try tools like ChatGPT, Claude, or Perplexity for research and decision-making.
Let AI teach you AI: "AI is a great teacher and you can use Gen AI to teach you how to use AI," English advised. Ask these tools to help you learn how they can be applied to your specific challenges.
Break something: Both panelists emphasized the need to take risks. Identify a process or approach that's been unchanged for years and reimagine it from scratch using AI capabilities.
Think small team, big impact: Consider how you might accomplish your goals with a dramatically smaller, AI-empowered team. What would change about your approach?

As English put it, "It's an incredible time for people to start new companies." The only question is whether you'll be one of them.

Watch the full session from Joel Cutler and Paul English here.