By Chris Heivly, Managing Director at Build The Fort and Startup Community EIR @ Techstars

As Thanksgiving rolls around, I find myself reflecting not just on gratitude, but on the mysterious forces that shape our paths — especially in the world of startups. There’s one question I keep coming back to:

Is it better to be lucky or good?

When people look at successful founders, they often attribute their rise to one of two things: raw talent or pure luck. But like many things in life, I’ve come to believe there’s a third, more nuanced force at play — fortune.

What’s the Difference Between Luck vs. Fortune?

Luck feels random. It’s winning the lottery. Being in the right place at the right time. Your pitch gets picked out of a pile. Your social media post goes viral. An investor replies on a holiday weekend. Luck is unbelievably thrilling, but fleeting and rare. 

Fortune, however, is luck with roots. It’s what happens when preparation meets opportunity, when relentless curiosity connects you to the right mentor, when showing up again and again finally pays off with a financing round or a big customer. Fortune isn’t fleeting — it’s an investment you can cultivate.

Can You Make Yourself Luckier?

Yes. I believe you absolutely can.

And no, it’s not a switch that you can turn on or off. It’s more like a dimmer switch — and you turn up the brightness through your actions.

Startups that appear “lucky” often have teams who’ve quietly engineered dozens of micro-decisions, relationships, and sacrifices behind the scenes. Founders who look like overnight successes usually have a ten-year backstory of intentional work — and setbacks — that put them in the position to seize what looked like a chance opportunity.

Looking back at my own story — especially the MapQuest days — I used to share with others that we just got lucky. Heck, we started this in Lancaster, Pennsylvania!

And in some ways, we were lucky. Timing mattered. The internet opened up and exploded. We had tailwinds no one could fully predict.

But as I get older (and maybe just a bit wiser!), I’ve started to see it differently.

We made ourselves lucky. We made good, hard decisions. We invested in databases, not PR headlines. We kept building better and better software when it was easier to stop. We watched. We listened. We adjusted. And we kept telling our story to whoever would listen.

It was our hands on the wheel — crafting the road, even if we didn’t always know where it led. (See what I did there? A little map humor.) That’s the magic of fortune.

So, back to that question — is it better to be lucky or good?

The best leaders I know are both: Good enough to make those investments, smart enough to navigate change, brave enough to make bold bets — and lucky enough to be in the right place when those bets pay off.

So this Thanksgiving, let’s be grateful for our fortune — not because it was handed to us, but because we had the heart, hustle, and hope to shape it.

Happy Thanksgiving. May your fortune be magical.

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