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On a Business Insider interview, what AI actually did to startups, and why "who cares" might be the most rational response to 2026.

A few weeks ago I got on a call with a correspondent from Business Insider. Nothing published yet, just a conversation, the kind of exploratory interview where a good journalist is essentially trying to figure out what you actually think before deciding whether any of it is worth printing. It's not the first time a publication has come knocking. Over the past few years I've been referenced or consulted by a handful of notable outlets trying to get a read on millennials, personal finance behavior, and what it actually looks like to build a consumer fintech company targeting a generation that is notoriously skeptical of the financial services industry.

What's notable isn't that they call. It's that they keep calling. And the questions are getting more urgent. The media is genuinely trying to understand something right now, which is how a generation that is by most measures doing fine keeps producing data suggesting it feels like it isn't. The paycheck to paycheck studies. The anxiety surveys. The polling on whether people expect to be better off than their parents. The answer keeps coming back worse than the fundamentals would predict, and I think journalists are starting to sense that the explanation isn't purely economic.

This particular conversation wandered across AI, young families, social media, the future of work, and what it's like to operate a startup in 2026. And somewhere in the middle of it I found myself saying things I hadn't quite articulated before, which is usually the sign of a good interview.

The correspondent, Tim, was skilled in the way that good journalists are skilled. He wasn't trying to trip me up exactly, but he was precise. He'd let me run on something and then circle back with a question that quietly put pressure on an assumption I'd made ten minutes earlier. The kind of conversation that makes you realize, in real time, that you've been carrying a belief you hadn't fully examined.

What he kept returning to was this: given everything you've seen, given the thousands of conversations and the millions of people you've reached through content, how do you actually get by? How do people navigate a moment this noisy, this uncertain, this relentlessly stimulating?

And my honest answer was that you just do. You wake up and try. With every good period comes a bad one. There are stretches of survival and stretches of thriving and the trick, if there is one, is not confusing either for permanent. That's not a profound insight. It's just what living inside uncertainty actually looks like from the inside, which I think is different from how it reads in a study or a headline.

But then Tim asked about Habits specifically, and that's where the conversation got interesting.

If you've been following what we're building, you know the broad shape of it. Started in a bedroom, moved to an office in New York, went fully remote. We compete with companies that have raised tens of millions of dollars and with legacy financial institutions that have been around longer than most living people. Every day something is breaking, someone wants their money back, someone has a question we haven't answered well enough yet. The wins don't get celebrated the way you'd expect because you slowly develop this orientation where problems are a privilege and the absence of problems just means you haven't found them yet.

What I told Tim is that we also got genuinely lucky in terms of timing. In 2021 and 2022, more was the only strategy anyone talked about. More capital, more headcount, more lines of code, more products, more surface area. And then ChatGPT arrived and within about eighteen months the entire calculus shifted underneath everyone's feet.

Here is what that actually means practically. Everything we have built at Habits over the past three to four months would have previously required somewhere in the range of five full time engineers across backend, frontend, DevOps, design, and QA. Nine months of work, conservatively. Somewhere between $500,000 and $750,000 in annual salaries before you account for bugs, vacations, sick days, and the general friction of human beings working together under pressure. What we're doing now takes a fraction of that, because the tools have compressed the timeline in ways that are genuinely hard to overstate.

I described it to Tim with a story that I think captures it better than any abstraction. A random Saturday, bad weather, basketball on in the background, laptop open. I'm going back and forth with a model trying to build a workflow I'd been putting off for months because it always felt too technically complex. A script that automatically scrubs new users and advisors, identifies which content or paid channel brought them in, and drops a clean report into our Slack channel every Monday morning. In the past that was a 30 to 45 minute manual process, assuming I even knew how to set it up, which I mostly didn't. Now it exists and I built it on a Saturday afternoon while watching basketball.

Speed and scale used to be competitive advantages. They're table stakes now. The question is what you do with the time that frees up, and most companies haven't figured that out yet.

But I want to be clear about something, because I think the AI conversation gets distorted in both directions. It is a feature, not a solution. It hallucinates. It tells you what you want to hear. It has genuine gaps in self-awareness about where it's wrong, which means the person using it has to be sharp enough to know where to check it. It should not be your primary source of financial advice or legal guidance or medical information or really anything where being wrong has meaningful consequences. The value is in augmentation, in compressing the time between an idea and a working version of it, not in replacing the judgment that has to live on top of it.

What Habits stumbled into is a specific combination of advantages that I don't think we fully appreciated until Tim started asking about it. Strong distribution built before everyone decided they wanted to be a content creator. Long relationships with users and advisors developed before AI made it cheap to acquire them. And a lean enough operation that we could pivot into this new environment without the institutional weight of a larger company slowing us down. We got lucky with the timing. I'm not going to pretend otherwise.

But here is where the conversation came back to the thing Tim was really trying to understand, which is the millennial generation sitting in the middle of all of this, making decisions that will compound for decades, inside a noise environment that has no historical precedent.

Should you get an MBA right now or is it obsolete? Should you take the job in a new city or stay close to your people? Should you fly to Japan while you're still unencumbered or is that irresponsible given the economic uncertainty? Should you buy the house in the suburbs even though your friends think it sounds boring? Should you become a Claude power user and a subject matter expert on every new tool that gets posted about on Twitter, or will that be irrelevant in six months anyway?

The honest answer to all of those questions, the one I kept coming back to with Tim, is who cares. And I mean that sincerely, not as a deflection. We are living in an era of such profound noise, such relentless stimulation, such an overwhelming volume of opinions and options and sales pitches, that the framing of most of these questions is itself part of the problem. The optimization culture that tells you there is a correct answer to every life decision if you just consume enough information is the thing making people miserable, not the decisions themselves.

What I keep seeing, both in the data from Habits and in the conversations I have every week, is that people are slowly returning to something simpler. Not naive, not uninformed, just more grounded in what they actually value rather than what the algorithm suggests they should. They're making the decision that feels right for their specific life with their specific people and their specific north star, and they're doing it without waiting for a consensus that is never going to arrive.

That's not a new insight. It's actually how most good decisions have always been made. We just forgot for a while because the firehose made it hard to hear ourselves think.

The most valuable thing you can do in an era of infinite options and infinite noise is get clear on the handful of things that actually matter to you, and then stop asking the internet for permission to pursue them.

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