The AI Agent That 'Lives in Your Texts' and Wants You to Have Fun

After years of building a traditional business centered on helping people get out of the house and find fun stuff to do, John Peterson, the CEO of The Nudge, just launched an agentic AI version of its “planner friend.” This new AI agent, which is now live across dozens of U.S. markets, proactively plans, recommends, and books things to do in your city, informed by your likes and dislikes, plans others are making locally and chats from other users. “Once you sign up, you start receiving texts directly on your phone a couple of times per week – each ‘nudge’ includes a brief itinerary, cost, and deadline to take action,” according to the company.

Peterson recently connected with Entrepreneur to share his thoughts on pivoting to AI without sacrificing quality, the key to connecting with Gen Z and the main question any leader needs to constantly be asking themselves as they explore new ideas.

Give us the elevator pitch of The Nudge.

The Nudge is the AI agent that runs your free time and lives in your text messages. It’s a subscription that tells you what to do on the weekend, helps you plan it, and can book things for you. Our vision is for The Nudge to handle all your free time one day.

Please tell us one “holy @#$!” moment about running your business — an unexpected problem you faced and how you overcame it.

One day in 2020, we arrived in the office and found out that due to COVID, our entire value prop of “we text you things to do in your city” was not going to work for a while. “Holy @#$!” indeed.

I remember bringing the team into our tiny basement office and telling them what I always say when @#$! hits the fan: “Don’t let a crisis go to waste.” Every catastrophe has opportunities if we can see them.

So we got to work on finding those opportunities. We realized that our value prop was not “we text you things to do in your city” but rather “we help you live your best life.” We started texting people how to do Zoom trivia nights with friends, which Mexican foreign film to watch on Taco Tuesday at home, and how to support local restaurants. We were able to think bigger and redefine how we help people.

What’s something small, like a daily routine or mindset shift, that changed the way you lead or perform?

Every day when I arrive in the office, before I begin my work, I write the answer to two questions in a Google Sheet: 1. When I really zoom out, I realize ____________. 2. Therefore, today I will ____________.

This helps me constantly put things in perspective. The biggest risk as a founder — both to our company’s and our personal well-being — is that we get stuck in the weeds. We spend too much time working on the wrong thing. We view ourselves as failures because something didn’t go well that week. I’ve found the solution is daily zooming out and reframing. It’s made me a better and, far more importantly, happier leader.

How do you pivot a traditional business to agentic AI?

My main suggestion is not to focus on this question: “How can AI make our product more efficient?” But focus on this one: “How can AI make our product better?”

Efficiency is a given, but I think the biggest risk for businesses pivoting to AI is that they are thinking about cutting costs, which can lead them to a cheaper, inferior product. I’m not optimistic about where this takes you in a competitive landscape.

If you focus on how agentic AI can elevate what you do, I think you’re more likely to apply the technology right. How can agentic AI make your customer 10x more satisfied? The answer to that question will take you a long time to build, but it will more likely guide you to something great.

What is your best advice for standing out to Gen Z?

Your mantra with Gen Z should be “don’t be boring.” Gen Z appreciates authenticity, values uniqueness, and doesn’t respect monoculture (everyone marketing/branding in the same way). I think a good rule of thumb is to ask yourself, “What’s a way to do or explain this that has never been done before?” If you’re just adding to the monoculture, you’re missing an opportunity to stand out to Gen Z.

And to connecting to customers in local markets?

That’s much more straightforward – you just need to prove that you understand the local POV. If you’re trying to expand your business to Chicago, people in Chicago don’t care that you’re big in LA. You need to speak to them like a business that only exists in Chicago would. This is not easy for scalability reasons, but we’ve found repeatedly that it has a big impact on acquisition costs and customer satisfaction.

What has been your strategy for using text messaging for customer communications and marketing?

Texts have higher open rates, higher read rates, and can now support things like in-text payments and advanced ways to interact (buttons, calendars, etc). That being said, the bar for texting customers is very high. My advice is to completely turn off your marketing brain and turn on