Hey Founder: The Hunt for Happy Accidents

My entire career has been about innovation and change. Literally. From the moment I first walked up to 7200 Johnson Drive in Pleasanton, California—where Clorox’s R&D building used to be (it’s tragically my local Costco now)—my job has been inventing new things and convincing other people they mattered.

Ideas. Concepts. New ways of doing old things. And then the harder part: getting others to buy in.

Along the way, I’ve helped my managers succeed. I’ve supported executives and, at times, been the executive supporting others across the organization. I’ve served as a Chief Evangelist (twice!) and spent years helping markets understand why we were different and why that difference mattered. I’ve been a consultant, lending my energy to other people’s visions, products, and strategies. And finally, I’ve been a founder—doing all of the same things, but this time for myself, building something new and asking others to believe in it.

So why wax poetic about my journey? Is this just arrogance from someone who thinks of themselves as an innovator or change agent?

No. Honestly, being an innovator isn’t a choice I made. It’s just in my DNA.

In fact, I tried to escape it. At one point, I went to Silicon Valley determined to get a “normal” job. You know—sales, customer success, something sensible. And as I like to say, they still put me in the crazy box.

Here’s how that happened. After consulting with NetBase, I was told they wanted to hire me. Naturally, I assumed it would be for a sales role or maybe head of customer success. But when I walked into the room to get my official offer from the chairman of the board, he slid a piece of paper across the desk. Four sentences. A salary. And the title Chief Evangelist.

I looked at him and said, quite literally, “What the fuck is this?”

He didn’t flinch. He just looked at me and said, “You were born to do this. It’s the perfect job for you.”

And that was the moment it finally clicked. My journey in innovation and change wasn’t something I chose—it was something I kept trying to outrun and couldn’t. No matter how hard I tried to be normal, they kept putting me in the crazy box. Forever destined to be a change agent.

So eventually, I stopped fighting it. I embraced it. Fully.

The reason for all this preamble—this diatribe, really—is simple. The harder I tried to avoid who I was, the more entropy pushed me right back to it. And frankly, when I look back on it now, my career is kind of a happy accident. Which is exactly what this post is about.

Happy accidents are wonderful things. But only if you’re paying attention.

They’re not passive moments. You have to notice them, understand them, and be willing to grab them when they show up. Too often, we march relentlessly toward what we think we’re supposed to do, only to find the universe quietly—or not so quietly—resisting us. We label those moments as deviations or obstacles.

But what if they aren’t?

What if they’re invitations?

Living freely means staying alert for the happy accident. They’re gifts. And not just ones worth embracing—but ones worth actively hunting for.

Defining Happy Accidents

So what is a happy accident?Honestly, it’s pretty much what it sounds like.

A happy accident is something you don’t expect to happen, but when it does, it produces an outcome that’s better than the one you were originally aiming for.

Simple enough, right?

But definitions are easy. Recognition is hard.

That’s why it’s worth going a level deeper before we talk about how to find happy accidents—or better yet, how to hunt them out. If you don’t really understand what they are and how they behave, you’ll walk right past them thinking they’re just noise, failure, or bad luck.

So what actually lies beneath the definition?

Point 1: Happy accidents are accidents — and if you’re not careful, you’ll miss them.

An accident, by definition, is an outcome you weren’t expecting. And here’s the catch: when you’re expecting something else to happen, your brain is usually busy reacting instead of reflecting. You’re trying to fix, correct, recover, or push harder—anything but stop and ask whether what just happened might actually be better than what you planned.

It sounds obvious, maybe even dumb, but think about it for a moment.

How many times has something you wanted to happen not happened—and your immediate reaction was to double down? Push harder. Go faster. Try to force reality back onto the rails of your original plan.

That instinct is one of the fastest ways to miss a happy accident.

Here’s a concrete example. Let’s say you believe your ICP is security startups. You’ve got a big fish on the line. Everything looks right. The deal feels inevitable. Because of that signal, you start pitching more of that same ICP, convinced that landing this one customer will unlock scale.

Then something happens. The deal dies.

What’s the typical reaction? Panic masked as urgency. Rather than slowing down to really understand why the deal fell apart, you push harder to close more deals just like it because, well… you need the revenue.

And this is where things go sideways.

Too often, our desire to drive things forward robs us of the space to step back. As founders, we are wired to scale. But that very drive to scale is also what creates unforced errors. We barrel forward when we should be listening.

The happy accident in this situation isn’t landing another deal. It’s the nuance hidden inside the loss. It’s the uncomfortable insight about why the deal didn’t close in the first place. That information is often far more valuable than the revenue you didn’t get—if you’re willing to see it.

That’s hard to do. It requires restraint. And humility.

But if you want to leverage happy accidents, it’s non-negotiable.

Point 2: The gap in time between the event and the happy accident is not always immediate

Letting your amygdala take over—as I mentioned earlier—is a surefire way to miss a happy accident.

When things go wrong, we react. And those reactions come in many flavors. Sometimes it’s the obvious freakout where you just lose your shit. Other times it’s more subtle—you double down, push harder, and try to force the thing that didn’t happen to magically happen anyway. Or you overcorrect entirely and sprint in the opposite direction from where you originally thought you should go.

All of these are overreactions. And they are perfect examples of what not to do when bad stuff happens.

It’s the same dynamic as the email that pisses you off. You know—that email. You know you should wait 24 hours before responding, but you don’t. You fire something back fueled by emotion, and once it’s sent, you immediately regret it. Happy accidents work the same way. If you react too quickly, you rob yourself of the chance to see what’s actually unfolding.

This is where the “things happen for a reason” mindset starts to matter—not as some woo-woo platitude, but as a practical tool. It’s about letting things flow long enough to understand them. Moving from the back of your brain, where overreaction lives, to the front of your brain, where rational thought resides, is one of the best ways to let the game come to you instead of forcing your way into bad decisions.

And here’s why that calm matters.

Happy accidents are often delayed.

There’s a reason they’re called happy accidents. Most of the time, you don’t immediately realize that what went wrong actually went right. It just happens in slow motion. The very nature of a happy accident is that you believe something terrible just happened—when in reality, good fortune may already be unfolding a few steps ahead of you.

This sounds obvious. But it isn’t. Not even close.

Let’s make this concrete with a very real founder scenario: raising money.

We’re taught to believe that raising capital to drive scale—and ultimately get rich—is the end-all, be-all. More money equals progress. Full stop. But in our case, there were multiple moments where raising more money would have been a mistake. We would have burned resources foolishly, convinced we had everything figured out when we absolutely did not.

Some of the biggest happy accidents in our market development came directly from the disappointment of not raising money.

That pause forced discipline. It forced learning. It forced us to see what we didn’t yet understand.

And that’s the point.

When you don’t get the outcome you wanted, staying calm long enough to ask why—beyond the frustration—is often where the happy accident is hiding.

Point 3: Happy accidents are points of divergence, not convergence—and they must be treated as such.

Ironically, one of the biggest enemies of happy accidents is something most leaders are actually very good at: convergence.

Great leaders are praised for being decisive, action-oriented, and relentlessly focused on next steps that produce value. That sounds like an accurate and admirable platitude, right? And most of the time, it is. But happy accidents don’t live in the land of convergence. They live somewhere else entirely.

This is where a metaphor my good friend Helen Eckmann taught me becomes incredibly useful—the idea of living on the balcony versus the dance floor.

When you’re on the balcony, you can see the entire dance floor. You can observe patterns, movement, collisions, and empty spaces. But when you’re on the dance floor, it’s a congealed mess of bodies. You can only see what’s directly in front of you.

And here’s where convergence sneaks in.

When you’re on the dance floor, you’re often trying to get others to notice you. You’re moving with purpose, convinced you’re a great dancer, hoping that if you execute well enough, people will pay attention, follow you, or copy your moves. That’s convergence. It’s performative. It’s decisive. And it’s focused on being seen rather than seeing.

Happy accidents don’t happen there.

Happy accidents are all about being on the balcony—but more importantly, about diverging when something goes wrong and taking the time to figure out what it actually means. They require widening your purview instead of tightening it. Expanding the frame instead of collapsing it.

Divergence is about stepping back and asking: What just happened? Why did it happen? And just as importantly—what do I not want to do next?

This kind of divergence means letting things ride for a bit. It means resisting the urge to immediately get back on the dance floor and perform your way out of discomfort. It’s about optioning—creating space to form a new hypothesis that you might test, explore, or simply think about before acting.

Happy accidents need room. They need time to develop. And they are often born not from decisive movement, but from thoughtful expansion—considering wider ideas that help you see a new direction that’s far better than the original one. Sometimes, even better than the path you were on before the failure that forced you to hope for a happy accident in the first place.

Convergence will always be there waiting for you.

But if you want to find happy accidents, you have to be willing to step off the dance floor—and spend some real time on the balcony.

Point 4: Happy accidents are not single events—they often stack on each other and build toward something way, way bigger.

Happy accidents are rarely one-off moments. They don’t just happen once and call it a day. More often, they show up repeatedly—sometimes back-to-back, other times spaced out just enough that you don’t immediately connect the dots.

And when you zoom out, the real point of happy accidents is this: they force you to embrace failure when bad things go down.

One of my favorite strategy analogies helps frame this. Imagine you’re sailing a ship. You have a true north, a clear direction. But every time you make a bad decision, you drift two degrees off course. Two degrees doesn’t feel like much. You barely notice it. But stack enough of those decisions together and, at some point, you wake up sailing east without realizing how the hell you got there.

Now flip that idea on its head and layer in happy accidents.

Happy accidents often feel like moments where you’ve been knocked off true north. Something didn’t work. A deal died. A plan failed. But when you look at them collectively, the piling up of happy accidents may actually be keeping you closer to your true north—or pushing you toward a much bigger horizon than the one you originally aimed for.

Each happy accident tends to deliver a better outcome than you expected. And every time that happens, something else shifts too. You start seeing more clearly. You begin stitching your strategy together with more calm and less panic. You stop reacting and start working the problem.

That’s the quiet gift of happy accidents.

They take the edge off leadership. They teach you how to operate with positivity, hope, vision—and most importantly, rationality—when things don’t go according to plan. Over time, they sharpen your leadership chops not by eliminating failure, but by reframing it.

Happy accidents are about trusting that when things go bad, there’s something useful hiding inside the wreckage. They’re about seizing the good from bad situations and not letting disappointment blind you to what’s emerging.

In many ways, this entire post is really about teaching you, as a leader, to smile at failure—and then figure out a new way forward, even when that path isn’t obvious yet.

Because being a founder isn’t for the faint of heart. Failure is for breakfast most days. And learning how to make it taste even remotely edible depends on your ability to look for the why behind the failure—and then run that failure straight into a triumph you didn’t even know existed.

That only happens when you’re willing to see the glass half full. When you can spot opportunity hiding in something else—something unexpected—that emerged from the trough of despair you wrestle with each and every day.

A Happy Accident Story

Enough pontificating. Let’s apply this idea to my actual reality.

We are founders who have been forced to bootstrap. Yes, we’ve raised some money. And yes, we are selling a concept—but more importantly, we’ve built a business. We have a product. We have sales. We have a team. We have renewing customers. We have product/market fit. We have real use cases people care about. We have a ton of customer feedback.

And we are still very early in our journey.

I have more happy accident stories than I could reasonably share. But the truth is, I didn’t invent this concept in theory—I learned it by living it. This post is really about articulating something that has been drilled into my head over and over again… so far.

To make the idea of happy accidents concrete, I’ll walk through a few of them using a simple structure:

• What went wrong

• What we thought it meant

• What happened that actually turned out to be better

  
  

Let’s start with the first one.

Happy Accident 1: The Pivot

This happy accident isn’t really about the pivot itself. In many ways, it was just good market research.

The happy accident wasn’t what we learned. It was what that learning led to.

What went wrong?

When we started the business, we had what we believed was a strong idea based on our experience at our previous company. The insight was straightforward: companies wanted to understand how things moved through their supply chains.

We had been using trucking data to map supply chains—showing where goods moved, who was doing business with whom, how flows changed over time, and a lot of other valuable signals. And to be fair, we knew the idea had flaws. But we believed it was solid enough to build around.

Then we did the market research.

What we heard—over and over again—was that the idea was… just okay.

As we listened more carefully, something interesting emerged. While people did want to understand where goods flowed, that wasn’t the pain keeping them up at night. The real problem—one almost everyone shared—was much more basic: there was no good way to find companies to do business with.

We heard it again and again. Across 40–50 hour-long interviews, the message was consistent. People didn’t just want insight into supply chains—they wanted a fast, reliable way to identify and understand companies in the first place.

So we pivoted.

We asked a new question: how could we help someone find any company in the world and understand everything important about it in five seconds or less?

What we thought it meant

We thought it meant we needed to scrap the original idea and build something new to solve this clearer, more universal problem. On the surface, it looked like a straightforward pivot—old idea out, better idea in.

What happened that actually turned out to be better?

The problem we decided to solve was a good one. Actually, it was a great one.

But the happy accident wasn’t the problem.

It was how we went about solving it.

To tackle this new challenge, we combined two things we knew deeply: our background in geospatial intelligence and our experience in social listening. That combination pushed us toward an approach that was bigger than we initially realized.

We ended up building a business knowledge graph—a massive, interconnected database of business information stitched together from fragmented signals across the web. That approach allowed us to solve the discovery problem we heard loud and clear from the market.

But it did something else.

As AI exploded around the same time we were building the company, we slowly realized we weren’t actually a business search engine. We were a knowledge graph company.

In a world where AI equals models plus data, we became the data side of that equation.

Our unique way of solving a very practical business problem positioned us squarely inside the AI ecosystem—particularly in a way that has massive potential to address one of AI’s biggest challenges: hallucination.

That was the happy accident.

Not the problem we chose to solve—but the approach we took to solving it. As the market evolved, we began to see just how big that approach might actually be.

Happy Accident 2: The Bootstrap

Like any startup, we wanted to grow fast. We wanted to scale. We wanted to hire. We wanted to thrive.

But we started our company in 2023—one of the worst funding environments in recent memory. VCs weren’t deploying capital the way they had before. Sure, people like to say money was being thrown at “anything AI,” but between high interest rates and the collapse of Silicon Valley Bank, many firms either disappeared entirely or became extremely gun-shy.

The environment mattered. A lot.

What went wrong?

Like any good founding team, we got started anyway. We built. We sold. We managed. But we also needed to raise money.

As that process dragged on, we found ourselves in bootstrap land—that uncomfortable place where you believe deeply in what you’re building, you have customers and momentum, but you still feel like you’re trying to keep a balloon in the air just long enough so it doesn’t hit the ground.

It’s a frustrating place to be. You can see the business growing. You can feel the idea starting to thrive. And yet, you want the jet fuel that VC money promises because you believe—maybe correctly—that you could go faster if you just had it.

At that point, we had built our business research interface on top of our knowledge graph, and we were convinced product-led growth was our path to the promised land. If we could build a business search engine that anyone could use, we thought we’d be lights out.

We wanted investment so we could hire a killer PLG marketer, build a killer website, and pour money into driving product adoption at scale. But we couldn’t get out of bootstrap land. The resources we thought we needed just weren’t coming.

What we thought it meant

We believed not raising money was slowing us down. Without capital, we thought we couldn’t scale our PLG strategy quickly enough. We couldn’t pour resources into perfecting UI/UX, refining lead gen, and cranking marketing through the roof.

It was a trough of despair, for sure. Everyone hits them. But not raising money made it feel especially hard to execute what we thought was our big vision.

What happened that actually turned out to be better?

Early on, we had talked about two possible paths: selling a SaaS product or selling data.

We had the SaaS product. Customers liked it—a lot. And then something unexpected happened.

One of our happiest customers—who we closed in about seven days and expanded with three months later—started asking if we would sell data to them. They told us we had created data in a way they hadn’t seen before. We had information about companies, people, news, and locations—all interconnected in one place.

What they were really reacting to was something deeper: the unique power of owning the world’s largest living business knowledge graph.

That’s when it clicked.

We realized we had built something much bigger than a seat-based SaaS product. Yes, PLG is still part of who we are. But we suddenly found ourselves able to sell data at much higher price points—because customers could experience its value through the SaaS product first.

And then the insight got even bigger.

We realized that the knowledge graph itself was the missing piece in the AI equation. Our customers didn’t just want dashboards or interfaces—they wanted to dig into the depth of the graph in ways a traditional SaaS product simply can’t support.

What emerged was a much larger vision: a new kind of digital library. A place where customers can curate their own data sets from our knowledge graph and then ask those data sets the business questions they actually care about. Up-to-date, ever-changing business intelligence—using exactly the data they choose—to get the answers they need.

This outcome was far bigger than what we originally imagined.

And it happened because we didn’t pour resources into executing the plan we had promised investors. We let the market come to us. And that only happened because we were forced to go slower.

Ironically, going slower produced a much better result.

So What’s Next?

To be honest, there are many more happy accidents I could share. But these two are the foundation of our growing opportunity. They represent moments of total frustration that ultimately led us to a much better place.

With patience and attention, the things that didn’t happen became opportunities.

Opportunities that would have been incredibly easy to miss had we not stepped back, kept learning, kept digging—and frankly, kept believing in our vision.

So much of our lives are made up of near misses. And many of those near misses aren’t the kind that could kill us—they’re the ones that challenge the story we tell ourselves about what success is supposed to look like. The deal that didn’t close. The money that didn’t come in. The path that didn’t materialize the way we imagined it would.

Happy accidents are a gift—if you have the patience to see them.

And for most founders, patience is not what we are taught to have.

But make no mistake: learning to thrive calmly in an ever-tumultuous sea is part of the job.

At some point, you stop fighting the chaos and start listening to it. You begin to embrace the uncertainty, to hear the song of the maelstrom as it sings—sometimes sweetly—guiding you toward a safer passage you couldn’t see before.

Happy accidents don’t remove the storm.

They teach you how to sail through it.