I have lived the venture backed startup life for over 30 years now. Besides founding/co-founding several companies myself, I have partnered with, interviewed and otherwise interacted with literally hundreds, if not thousands of founders and founding teams. That is why a recent post by Caleb Sima touched me. Caleb needs no introduction in the world of cyber. He is an accomplished multiple time entrepreneur who has made significant contributions to the state of cybersecurity and one of the smarter people in the industry. His latest company is Whiterabbit. 

In Caleb’s post you can feel his frustration and disappointment in the current state of the industry in regard to seemingly everyone founding a company and their reason—or maybe lack of reasons other than making money—for doing so.

First of all Caleb, if you are an old man here, what does that make me. You are not quite old yet.

But what Caleb describes is a recurring cycle in tech. I have seen this pattern before and can pretty much tell you how it ends.

I also have had a chance to understand what separates the winners from losers in the VC startup roulette game. Not that I can say for sure—if I could, I wouldn’t be writing articles like this… well, not as much anyway.

I was lucky enough to sell the first company I founded to my friend Brad Feld and a roll-up he was heading up at the time. Brad, of course, is one of the biggest friends of founders and startups there is. Today people know him from Foundry Group, Techstars and his books on startup communities. But back then, in 1997, he was a managing director at SoftBank Venture Capital.

And that was prime time for the dot-com era.

SoftBank was early money in companies like Yahoo, E*Trade, Alibaba and about 250 others. They called it a keiretsu. I sold my company into the platform Brad and his team were building. Then he asked me to run business development.

Over the next 36 months, we acquired 30 companies, went public, rode the dot-com wave all the way up—and, unfortunately, all the way down.

Part of my job was meeting the companies in the SoftBank keiretsu and figuring out who we should partner with. Brad would also ask me to evaluate startups they were considering funding.

In other words, I had a front-row seat to hundreds of founders and founding teams.

And what I learned then—and what I’ve seen proven over and over again since—comes down to one thing.

Now picture me doing my best Jack Palance as Curly in City Slickers, holding up one finger.

That one thing is PASSION.

It’s what separates the winners from the tourists.

Let me be clear. I’m not talking about passion for making money. We’d all be fools to pretend money doesn’t matter. But if your primary passion is the exit, the valuation or the lifestyle, sorry Charlie—Starkist wants tuna that tastes good.

Passion for money alone won’t get you through what it takes to build something real.

The founders who make it—the ones who build enduring companies—are obsessed with the problem. They talk about their customers the way a doctor talks about patients. They want to know what hurts, what isn’t working, what could be better. They listen. They iterate. They stay up at night thinking about how to fix it.

They’re not chasing a category. They’re chasing a solution.

And that passion? It’s contagious.

Early-stage startups don’t run on revenue. They run on belief. Your team feeds off the founder’s energy. When the founder cares deeply about the mission, they hire people who care. Culture forms around the problem, not the paycheck.

But when the mission is “let’s ride this wave and flip it,” everyone feels it. The energy is different. The commitment is different. And when things get hard—and they always do—that’s when the cracks show.

Because passion for money doesn’t get you through 2 a.m. customer calls. It doesn’t get you through missed quarters, failed releases or investors asking tough questions. It doesn’t help when you’re pushing the rope uphill and gravity feels stronger every day.

That’s when passion for the mission becomes the mother’s milk of the company.

If this all sounds familiar, it should.

What Caleb is reacting to in cybersecurity—and what we’re seeing across tech right now—is the same pattern we saw in the late ’90s. Back then it was dot-com. Today it’s AI, agentic, autonomous, whatever label is hot this week.

Add the right buzzwords to a pitch deck and suddenly money shows up.

And just like then, it creates two kinds of companies: builders and gold diggers.

The builders are obsessed with solving real problems. The gold diggers are chasing the multiple.

Here’s the thing about cycles: they always correct.

Fools and their money are quickly parted. Investors who fund financial vehicles instead of mission-driven companies eventually learn the lesson. Markets tighten. Customers get more selective. The easy money dries up.

And when the tide goes out, you find out who was building for real.

But this isn’t just a message for founders. This is a leadership lesson for every DigitalCxO out there.

Because the same dynamic is playing out inside enterprises right now.

How many AI initiatives are being launched because “we need an AI strategy”?

How many transformation programs start with technology instead of a problem?

How many teams are being asked to move fast on something leadership doesn’t actually believe in?

Employees can smell the difference between conviction and compliance.

If your AI program is about keeping up with competitors, your team will treat it like a project. If it’s about solving a real customer or operational problem that leadership truly cares about, it becomes a mission.

Passion scales. Strategy decks don’t.

The best enterprise leaders I know talk about their initiatives the same way great founders talk about their companies. They’re not excited about the tool. They’re energized by the outcome. They know who it helps. They know why it matters.

And their teams feel it.

Because leadership isn’t about authority. It’s about energy transfer.

If you don’t believe deeply in the problem you’re solving, your organization won’t either.

That’s the real takeaway from Caleb’s post.

Yes, the industry feels crowded with tourists right now. Yes, there’s too much FOMO and not enough purpose. Yes, investors sometimes fuel the wrong behavior.

But this isn’t new. It’s just another turn of the wheel.

The people building for the wrong reasons will get shaken out. They always do.

The ones who stay—the ones who endure—are the ones who care about the problem more than the outcome.

So if you’re a founder, ask yourself: would you still be working on this if the exit never came?

If you’re a CXO, ask yourself: does your team know why this initiative actually matters?

Because leadership, at its core, is simple.

Not easy. But simple.

People follow passion.

And in every cycle—dot-com, cloud, cyber, AI—the leaders who win aren’t the ones chasing the money.

They’re the ones chasing the mission.

Everything else?

That’s just tourism.