At the height of the late-90s startup bubble, Chris Sacca was worth $12 million. After the bubble burst, Sacca was in the hole to the tune of $2.125 million — it would’ve been $4 million but he negotiated nearly half of the debt down.

His Silicon Valley peers were also in dire straits, though most of his friends’ debt was in the tens of thousands, not the millions. Sacca describes it like this: “You couldn’t get a U-Haul out of San Francisco because everyone was taking them out of town and not bringing them back.” Meanwhile, Sacca was sneaking into $25 networking events through the kitchen, writing Terms and Conditions for porn sites, and inventing an “international consultancy” to make himself look more professional (check out the website for the “Salinger Group” here)

But no matter how bad things got, Sacca says skipping town for his hometown in Buffalo was simply not an option. And for him, the “Never say die” attitude is more than just a platitude — it’s built into his DNA.

He recalled being six years old and going on a camping trip at Long’s Peak, one of the highest mountains in Colorado. He and his parents woke up at 3 AM to hike to the summit, but two miles from the top they turned away due to inclement weather. “I was devastated,” Sacca says. So devastated in fact that, when the Sacca clan got back to their campsite, Chris kept walking, and he didn’t stop until he had covered the two miles he’d missed at the top.

When faced with failure, Sacca remembers this childhood tale, but he also looks to his friends and colleagues for inspiration. “Talking to Evan Williams, he doesn’t weigh successes versus failures. Failure isn’t part of the equation. Up until the point that it fails, failure isn’t a possibility.”

Some might call this “ego,” but Sacca says it’s just good old-fashioned irrationality, a trait that our editor-in-chief Sarah Lacy says is part of what makes the Silicon Valley ecosystem so exciting and innovative.

In fact, if Sacca was being rational, he probably would’ve declared bankruptcy. “Declaring bankruptcy would’ve been a financially savvy move,” Sacca says. “But I didn’t admit that going home was one of my choices.”