Positioning for Your AI Moment

This is tmrw — a weekly note on money, decisions, and what tends to matter over time.

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I am at the New Media Summit in Austin right now.

500 writers, creators, and operators are getting together to talk about how modern people, you and I, consume media and how to better reach them. I can tell you one thing from the conversations happening here. It is about AI and what it means not just for their businesses, but for them as people.

I wrote about this last week but the feeling in the halls of the Hilton is palpable. I walked into a conversation where the group was discussing the viability of Salesforce’s business model… at a media conference.

Wall Street has a magnifying glass on companies right now. Nvidia just blew it out of the water. But what is really happening is whether a company has had its “AI moment” yet.

C.H. Robinson, the long-tenured logistics company, is the perfect example of what is going on. On February 12th, the stock fell off a cliff. A karaoke company turned logistics startup said its AI product would disrupt freight brokerage in America. The market looked at that story and decided C.H. Robinson was suddenly worth 24 percent less.

Here is what did not change for CH that day:

• Their customers did not disappear.

• Their trucks did not stop.

• Their systems did not break.

What changed was the story about what AI might do to their moat over the next few years.

You are seeing versions of this in other places. IBM had a moment tied to its legacy COBOL exposure. Salesforce and Adobe have both had AI fear days where investors suddenly priced in a world where native AI tools chew into their margins. A small team launches an AI tool aimed at an incumbent. Wall Street imagines that tool working perfectly and investors sell first and think later.

The question that matters is simple. Is that actually true? Does AI really mean that decades of work connecting shippers and customers is suddenly worth a quarter less? Probably not. But then again, who really knows?

I am not interested in turning this newsletter into an AI commentary blog.

I am interested in what this means for actual families. People who gather at Thanksgiving and Christmas, who want to take their kids or grandkids to Europe, who are trying to retire without wondering if the floor is going to drop out from under their career or portfolio.

That is where my work lives. In between investing capital in this new age and helping real families navigate the complexity that comes with it.

We have all lived through tech changes. I remember as a kid talking with my dad about whether the world was going to break during Y2K. It did not. The internet did not put everyone out of business. It created a wealth flywheel and many new industries. TurboTax did not kill accountants. It changed how we file and pushed CPAs into different, higher-value work.

What is different now is who is in the crosshairs, not what. You can realistically imagine replacing a 200,000 dollar a year software engineer with a 20,000 dollar a year AI agent that never takes a lunch break. A developer I talked with last night spends five hours a day coding with AI. You can imagine a small team using AI to do the work that used to require a floor full of people. That is not simply a better mousetrap. It is a different labor market.

Let’s bring in the complexity curve.

The complexity curve peaks in your 50s. You are squeezed between aging parents and expensive kids. You are in the high-earning part of your career or running a business at full throttle. You are probably never making more and never spending more. It is the stretch right before retirement when everything is in motion. It’s key to avoid mistakes here.

What is different about the complexity curve heading into 2026 is the shifting of risk. Knowledge is becoming a commodity. Large language models are taking the kind of knowledge many Americans get paid for and making it cheap and abundant. If you own a business or have seven years left before retirement, and you are a 50-year-old with a mortgage, kids, and a career built on being smart, the game has changed.

So the question becomes, how do you compete and stay ahead as AI rolls through the economy and more companies and individuals have their own C.H. Robinson moment?

I am not sure where exactly this ends, but here is what I am focused on personally, with our clients, and in our business.

I believe these are reliable places to focus and build competitive advantages.

Infrastructure. Relationships. Taste.

Infrastructure: stress-testing your financial engine

If you are in your 50s, the infrastructure of your financial life is built. Income is coming in. Spending habits are set. There is how you invest and the system you use to manage risk. You have been using your own infrastructure for decades at this point. Meanwhile, the foundation of how you retire is also being built.

These AI moments are stress tests of infrastructure.

C.H. Robinson’s business did not vanish in a day. The market is saying that AI might connect suppliers and customers more cheaply than a traditional broker, so the long-term value of their financial engine gets marked down.

The same thing can happen to you, your business, or the business you work in. It just will not show up as a stock chart.

If you were a publicly traded stock and worked in logistics, software, or law, the market might look at the AI stories in your industry and quietly mark down what it believes your earnings power will be three years from now. Nothing changes in your life this week. The kids still need braces. The property tax bill still shows up. But the long-term value of your income stream might have shifted down and to the right.

What is difficult is that you may not know it.

That is career risk.

The infrastructure you have built, your career, might be worth less than you think, and there is no press release to let you know.

Investing in your own infrastructure in this environment means getting honest about a few things. You need to understand where your income comes from and how durable it is if your industry has a karaoke-to-logistics moment. You need systems in place so that if your job or business hits an AI air pocket, you are not making panicked decisions in the middle of a crisis.

That might look like more cash than feels efficient on paper. It might look like diversifying income sources sooner. It might look like taking skill building seriously instead of assuming the current job will roll along for another fifteen years.

Infrastructure is boring until it is everything. A bridge is taken for granted until it collapses.

Relationships: business still runs on people

As AI takes more of the monotonous and analytical work, something should open up. There is more room for humans to be human.

Businesses will still be led by people. Even in a company filled with AI agents, someone is choosing direction, setting priorities, selling, and deciding who to work with. That is where relationships come in.

If a big company decides it needs thousands fewer employees, most of those people will not get to choose the timing. You do not get to schedule your own C.H. Robinson moment. I do not either. When that happens, how do you get the next job or opportunity? Most of the time it is not because your resume beat an algorithm.

It is because someone you know is willing to make a call.

We are even seeing this reflected at firms like McKinsey. The CEO recently described their headcount at 60,000, split between 35,000 people and 25,000 agents.

Personally, I have been treating this environment as a midlife refresher course in what makes a quality relationship. Not sleazy networking. Actual friendship. How to be someone people are glad to know. How to show up in ways that are useful and kind. To be a pleasant, uplifting person of value in any room I enter.

In an AI-heavy world, being the person others want on their team is an asset that defends your income. It is soft on the surface, but hard in its impact when things go sideways. Your relationships shape your opportunity set. Relationships create luck.

So part of upgrading your infrastructure is upgrading your relational infrastructure. Accruing relational capital. Calling old friends. Getting involved in your community in a different way. Being known for doing good work and being trustworthy. The things that used to sound like nice-to-haves now have a direct line to your resilience.

Taste: choosing the right problems

The last piece is taste.

Imagine a French chef and a line cook at a busy chicken drive-through. They are both cooking the same animal. It is still protein on a plate. It might all taste great. Your local chicken spot might even beat the fancy place.

What is different is the interpretation. The choice of what to do with the same raw ingredient. That is taste.

In this AI world, information is abundant. Tools are cheap. You and I could build a software project in a weekend that would have cost hundreds of thousands of dollars a decade ago. There is an abundance of possibility.

When everything is possible, what you choose to work on matters more.

Taste is your filter for that. It is how you decide which problems are worth your time and which ones you let pass by. It is how you decide whether to keep chasing hierarchy in a role that AI might hollow out, or move toward something that aligns with where the world is going. It is how you decide which businesses to own and which ones to avoid.

Inside our firm, I am looking at our software stack differently because of this. The default used to be to find a vendor for everything. Pay a subscription. Live with the compromises of big-box software. Now, with the tools we have, it can make more sense to build exactly what we need in-house in some areas. That is a taste decision. It is choosing not just how to solve a problem, but which problems we want to truly own.

In your life, taste might mean deciding to really learn how AI works in your field instead of dismissing it. It might mean encouraging your kids to think differently about career choices. It might mean spending time with people 25 years younger than you to understand how they see the changing world. It might mean retooling your business in a different direction.

Taste is subjective, but it is also a competitive advantage, just like it always has been.

Positioning for your own AI moment

The world that got us here is fading into history. There are twenty-something founders building native AI companies that are reimagining entire industries. That matters for you, for me, and for everyone.

The dreams have not changed. You still want to care for your kids and grandkids, travel, give, and retire with confidence. The path to get there has changed. Even if you are retired, the path is different for your children and grandchildren.

The risk now is assuming that what got you here will get you there. It will not. This is not about panic. I am as excited about the future as I have to ever been, even if it feels unnerving some days.

It is about positioning for the inevitable.

You and I will not time our own AI moments. What we can do is prepare. We can build the right kind of infrastructure so our personal financial engines are durable for the world we are going to live and invest in. We can deepen relationships. We can sharpen taste so we are working on the right problems and owning the right kinds of businesses.

Complexity is not the enemy. Complexity just makes the real risks easier to see.

Thanks for your time this week.

If you’d like to talk through how this applies to your own financial life, you can learn more about our work at Fjell Capital here.

And if you found this edition useful, let me in the poll below or reply with a quick note—I read every response.

More next week.