Starting a company means embracing a strange, often uncomfortable reality: status limbo.

One day, you’re managing a team, earning a solid paycheck, and working in a nice office. The next, you’re back to zero—no salary, no brand recognition, no credibility beyond your own conviction. It’s the most disorienting transition in a founder’s journey, and if you don’t learn to sit with it, it can lead to some really bad decisions.

In my latest Founders & Empanadas episode, I had the chance to sit down with Patrick Rafferty, co-founder of UserHub, to unpack the mental game of startup life, the role of AI in software businesses, and the often-overlooked challenge of communicating across cultures.

Surviving Status Limbo

Patrick calls it status limbo—that awkward, ego-crushing phase where founders suddenly go from “someone” to “who?” It’s a phenomenon I’ve seen play out over and over again.

When you’ve spent years building a career, earning promotions, and leading big teams, stepping into the unknown is painful. The temptation is to recreate the comfort of your past environment as quickly as possible: hiring too fast, spending on a fancy office, or—my personal favorite—sinking tens of thousands into a rebrand before you even have product-market fit.

But here’s the reality: status limbo is a feature, not a bug. It forces you to prove yourself again, to build from first principles, and to make every decision based on what actually matters, not what looks good.

Patrick made a great point: the best founders aren’t the ones obsessed with status; they’re the weirdos, the romantics, the pirates. They’re the people willing to operate outside the usual rules, resisting the urge to mimic big companies before they’ve earned it. It’s a perspective that might make some uncomfortable, but it’s also the difference between those who survive and those who flame out too soon.

AI, Hype, and the Fear of Irrelevance

If status limbo is the first founder trap, the second is AI anxiety.

Patrick and I both had a moment last year where we fell into the same spiral: scrolling LinkedIn, seeing post after post about how AI was about to replace entire industries, and wondering, Is my company doomed?

At a Stripe conference in 2024, Patrick watched a panel of engineering leaders predict that a team of one to five engineers could completely rebuild DocuSign in a year. Think about that—DocuSign is a $20B company with thousands of engineers. And yet, these credible experts were suggesting that AI might reduce the manpower needed to build something similar by orders of magnitude.

Sounds terrifying, right?

But a year later, DocuSign still exists. Their engineers are still employed. AI is making things more efficient, but it hasn’t wiped out entire businesses overnight.

The key takeaway? The rhetoric is always ahead of the reality. If you’re a founder, you can’t afford to let the hype cycles dictate your decision-making. AI is a tool—a powerful one—but it’s not an overnight extinction event.

Patrick’s advice? Don’t get caught in the noise. Instead of doomscrolling, listen to AI researchers (not just the most sensationalist founders), experiment with the tools yourself, and focus on where AI can enhance your business, not replace it.

At NeoWork, we’re leaning into AI-assisted teammates—helping companies integrate AI into their support, ops, and executive assistant workflows—but always with a human layer in the loop. Because as impressive as AI is, it still hallucinates. And when you’re dealing with real customers, “hallucinating” isn’t exactly an acceptable excuse.

The Art of Communicating Across Cultures

Beyond status and AI, one of my favorite parts of our conversation was Patrick’s take on communication in remote teams.

We both learned the hard way that what works in an office doesn’t always work across cultures. Patrick used to fire off Slack messages like rapid-fire texts—no punctuation, no context, just quick bursts of thoughts. But when he started working with global teammates, he realized this was causing a ton of confusion.

What made sense to him felt abrupt, unclear, or even rude to others.

I had the same experience. When I first started working with my team in the Philippines, I noticed some people were hesitant to speak up about inefficiencies. Turns out, pabibo (a Filipino term for drawing attention to yourself) isn’t a positive thing culturally. In the U.S., pointing out flaws in a process is seen as helpful. In the Philippines, it can be perceived as arrogance or overstepping.

That’s why I now over-index on voice notes and casual check-ins. Letting people hear my tone helps them know I’m not upset—I just want to get something done.

Patrick’s big realization? In remote teams, communication needs to be painfully clear. If your Slack messages, Figma files, or documentation don’t tell the full story, you’re setting your team up for failure.

The fix? Be intentional. Be explicit. And when in doubt, say more, not less.

Building for the Future

The best founders aren’t the ones who obsess over their title, their brand, or whether they look impressive.

They’re the ones who get comfortable in the status limbo. They make smart decisions instead of performative ones. They use AI as a tool, not a fear-fueled distraction. And they learn how to communicate across cultures instead of assuming their way is the only way.

Patrick and I barely scratched the surface in our conversation, but these are the themes that keep showing up over and over again—for me, for my team, and for every founder I talk to.

If any of this resonated, I’d love to hear your thoughts. How do you navigate the weird in-between phases of building a startup? And what’s been your biggest lesson in leading remote teams?

Let’s keep the conversation going.

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