Why Now Is the Best Time to Start a Company—or Work at a Startup

Every few weeks, someone gets introduced to me asking a similar question. They're ambitious, talented, thoughtful, well-networked— the kind of person who could build something meaningful. And they’re at the crossroads.

“Should I make the jump to start a company, or join a startup?”

It often starts as curiosity—“I’ve been noodling on an idea for years,” or “I’ve been helping a team on nights and weekends.” “I don’t feel that I’m learning enough at my current company.” But pretty quickly, the real doubts show up. “I have a good setup right now,” they’ll say. “What if the market turns again? What if funding dries up? What if I fail? What about health insurance?”

I often find myself repeating the same thing over and over again, to the point where I’ve become a bit of a broken record:

This is the best time to start a company, or join a start-up.

Here’s my honest belief: over the long run, there’s more risk in not starting a company—or at least in not working at a startup that’s at the forefront of innovation.

If you’re not getting exposed to the new tools, reasoning models, and intelligence being developed by OpenAI, Anthropic, and others, on a day to day basis, you run the risk of your skills slowly becoming less relevant.

Here’s why.

1. Startups are the fastest way to invest in yourself—and the best way to learn how to apply AI where it matters.

A lot of people think the breakthrough with AI is the technology itself. Yes, the models are impressive, my mind is blown. But, learning how to apply this technology to solve problems you observe, or face on a day to day basis is going to create just as much value.

OpenAI, Anthropic, Mistral—they are not going to build the best tools for every vertical, all over the world. One of the learnings we had in the self-driving world was the last 5% of development takes 95% of the effort. They don’t live inside the workflows of medical practitioners or customer support at an airline company or claims adjusters or home maintenance professionals. They’re not sitting in front of the call center screen at a hospital, navigating a 10-step UI just to change an appointment.

But, what they do is provide the foundation for you to build a product, without spending billions of dollars to develop that layer of reasoning and intelligence. It is just breath-taking to imagine all the problems in the world these technologies can be applied to solve.

There is an enormous opportunity for domain-specific application builders to reimagine the products we use every day—layering AI on top of the complexity that others overlook or don’t understand. And startups, almost by definition, are the best vehicles for this kind of work. No legacy systems. You can try things, fail, adjust, and move faster than anyone else.

Currently, there’s unfortunately an asymmetric learning environment. If you join a startup right now—especially one where you’re building with AI, integrating it into real user flows, shipping things, and watching how they land—you will most likely learn more in 6 months than most people will in 6 years at a larger company. And the skills you develop will keep you relevant for the next few decades.

If you believe the future belongs to people who know how to apply these tools, then investing in your own learning—through building—is actually the safest best you can make.

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2. There’s capital flowing again—especially in sectors people thought were dead.

Let’s reflect upon robotics.

Just a few years ago, it was almost impossible to raise a round of capital to fund robotics startups. After the self-driving bubble popped—Zoox, Argo AI, Drive.ai, a dozen others—it felt like investors ran from most things that looked like hardware. Customers folded, budgets dried up, and the stocks were all crushed.

But in the last 6-12 months? That’s flipped.

There’s been a re-surgence in robotics. Rounds are getting done, with top-tier firms.

It’s because foundation models change what’s possible.

For years, the limiting factor in robotics wasn’t just the hardware—it was hardware and software. It was the complexity of edge-case logic, the difficulties of sensor fusion, the need to spend hundreds of millions to create digital maps with centimeter precision of the real world, the difficulty to scale without writing domain- specific rules.

Now, with vision-language models and multimodal models, robots can adapt to new contexts with far less human coding. You can feed a model an image, a video, and it can describe to you what is happening there, without collecting any real world data and hiring a team of folks to analyze it.

It’s not just an incremental improvement. It’s a step change in what’s possible. And that’s breathing life back into industries that had stalled.

If you’re thinking about starting something in a sector that looked closed off two years ago—it might be time to take another look.

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3. The best talent is out there, and it’s more open to startups than ever before.

In 2017, when we started rideOS, the hardest part of building a company wasn’t fundraising. It was hiring. Great engineers had four offers. Comp was through the roof, and big tech companies constructed offers to price out start-ups. Everyone was indexing for stability, prestige, liquidity.

Now? There’s a different energy.

Job postings for software roles are down significantly. People who used to feel stable at big companies have been through multiple rounds of layoffs. More and more are starting to question the trade-offs of staying on a treadmill that no longer feels secure.

I’m not saying hiring is easy now. It’s never easy. But there’s more openness. More curiosity.

If you have a clear mission, and a real story to tell—especially one grounded in a space you know well—you can recruit people who wouldn’t have picked up the phone in 2017. People who want to build. Who want to grow. Who want to feel the satisfaction of doing hard things, with other people who care.

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What’s the worst that can happen? You go back to what you are doing now in 12 months :) The act of building, learning, exposing yourself to new technologies, is the best investment you can make in yourself.

If you start now, you won’t just be relevant—you’ll be ahead.