AI is coming for us (here's my plan)

Last week, I found myself in a packed room in New York City at the OOO Conference, hosted by Ankur Nagpal and Andrew Yeung.

The event brought together some of my friends like Sahil Bloom and Nathan Barry, and people I've admired from afar for years, including former presidential candidate Andrew Yang and writer Packy McCormick. Add in 500+ successful entrepreneurs, and you’ve got one awesome event.

During many of the interviews and panel discussions, a common question kept coming up.

"How are you thinking about AI?"

What struck me most wasn't the variety of answers, but the similarity among them. Almost everyone shared a conflicted perspective.

Most speakers expressed real excitement about AI's potential. They talked about increased productivity, automation of boring tasks, and new creative possibilities.

But the excitement always came with a caveat.

Sahil captured my sentiment when he questioned what kind of work will be available for his 3-year-old son when he grows up. His comment articulated something I've been feeling but hadn't fully processed.

I'm excited about AI. And I'm terrified of AI.

Both feelings can be true in tandem.

The coming disconnect

We’re witnessing the beginning of a profound shift in how humans create and capture value.

AI is already reshaping every industry I'm familiar with. Content creation, programming, design, customer service, and more. These fields are feeling rumblings of change that are impossible to ignore.

I've watched friends who built careers on skills that are suddenly being automated. They're not losing their jobs overnight, but the ground beneath them is starting to feel shaky.

And AI is coming for my work, too. Stuff that took me hours two years ago can now be done in minutes. That makes the barrier to entry pretty low all of a sudden. That's liberating in a way, but also concerning.

What happens when more complex pieces of our work become automated? And what happens when businesses realize they can get 80% of the quality for 5% of the cost? Or effort?

This isn’t me being pessimistic for the sake of engagement. It's just where I think things are headed.

The human hedge

During the OOO conference, I was interviewed on stage by Andrew Yeung. He asked me what I’m doing in the AI age to ensure I don’t get impacted as hard as others already have.

And my answer is simple. I'm hedging against AI by doubling down on being human.

This means focusing on the things that AI will struggle to replicate for the longest period of time:

• Building authentic relationships
• Creating spaces for genuine connection
• Making intuitive judgments based on decades of experience

As AI gets better, I think the value of authentic connection will increase. Sitting across from someone (in the same room), having an actual conversation, feeling that energy, and building trust will become more appealing than ever.

I'm not rejecting AI here. I’m using it every day, and I’m having a lot of fun with it. But I'm also making conscious investments in the human side of my work and my life.

What does this mean practically?

For my business, this human-first approach translates to several shifts:

I'm prioritizing community.

I’m focused on in-person events and interactions over purely digital growth.

I'm focusing on depth rather than scale. It’s better to have deep relationships with fewer people than shallow engagement with many.

I'm spending more time developing relationships with people I genuinely connect with, rather than "networking" broadly.

The irony isn't lost on me that I'm writing this in a newsletter, a one-to-many, relatively impersonal format. But I'm sharing my experiences and personal perspective, and lots of you care what I have to say. So here we are.

How to find your human edge

If you're worried about AI, here are some questions to ask yourself. They're not easy to answer, but they're important to consider.

• What parts of your business require human qualities like intuition, judgment, and emotional intelligence?
• Where do you provide value through relationships and trust instead of just knowledge?
• What experience do you have that is so contextual and personal that it'd be nearly impossible to simulate?
• What part(s) of your business would benefit from a stronger human connection?

Your answers to these questions should illuminate some important parts to focus on in your business, and maybe some new opportunities you haven’t considered.

The community connection

My own desire for human connection is the reason I launched Unsubscribe a couple of weeks ago. I created a private network of 800+ entrepreneurs who are building businesses with the specific intention of having their businesses improve their lives.

My mission was to have a space where entrepreneurs could get support and perspectives from people who have actually done something. Where we can share struggles and wins, and build real relationships. We’re even having IRL events to meet each other, sit across from each other, and have real conversations. I’m so excited for that.

Because AI is coming for more of our work than most of us realize. And that's not fear-mongering. It’s just acknowledging reality.

But being human will always matter. And I think it will matter more than ever.

So while I'll continue using AI tools to amplify my work, my big bet is on people. On the value of connection, judgment, and shared experience.

The entrepreneurs who will win the next decade won't be the folks who use AI 100% or the people who reject it altogether. The winners will understand how to use AI to augment their businesses and build real relationships at the same time.

And these winners certainly aren't going to do it alone. They'll do it alongside other folks who understand and appreciate the challenges and opportunities of this crazy, interesting moment.

And that’s all for today.

See you next Saturday.

P.S. If you're looking for a group of entrepreneurs to connect and build with, check out ​Unsubscribe​. On Thursday, we had Daniel Vassallo come in and give a 60-minute workshop on an Introduction to Small Bets, his strategy for building companies that work.

Next week, we have former SPI Media CEO Matt Gartland talking about new ways to nurture revenue, followed by Dan Koe showing us how to use AI more efficiently in life and business. And if you're in the UK, we have our first social event on June 1st.

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