Keep Going: The hardest choice in startups

Anyone who’s built something from scratch knows the struggle. Some days you feel unstoppable, and other days, quitting seems like the only option. This week on Keep Going, I sat down with Spenser Skates, CEO of Amplitude, to talk about the challenges of staying the course, the moments when giving up seemed like the rational choice, and what ultimately made the difference in his journey.

The Early Struggles

Spenser co-founded Amplitude 13 years ago. The company, now a public entity generating $300 million in annual recurring revenue, wasn’t always a sure bet. Before Amplitude, Spenser worked on a different startup, Sonalight, which didn’t gain traction. Despite having a few hundred thousand downloads, retention was weak, and it became clear it wouldn’t be a breakout success. Instead of walking away from the startup world altogether, he and his co-founders went back to the drawing board.

Amplitude was born from their own need to understand user behavior through data. But early on, raising money was brutal. Investors weren’t convinced. For nine months, Spenser scraped together funding in $50,000 increments, often making it seem like they had more momentum than they actually did. At one point, a premier Silicon Valley investor told them, “We love you guys, but we hate your idea.” That’s a gut punch.

When to Stick With It

So how do you know when to quit and when to push forward? For Spenser, a key realization came from reading Founders at Work by Jessica Livingston. The book highlighted how almost every successful startup had a point where, rationally, they probably should have quit. But the founders didn’t. That stuck with him. He and his co-founder made a pact: they’d give Amplitude at least two years before even thinking about walking away.

That decision paid off. Amplitude’s early customers saw real value in their product analytics tools. They launched in 2014, and by shifting focus from product development to sales, they went from zero to $1 million in ARR in nine months. By 2015, they had five offers for a Series A. Then the real growth began: $1 million to $4.5 million, then to $13 million, then to $31 million. The numbers kept climbing.

The Real Challenge: Staying in the Game

Startups don’t just fail because they can’t raise money or because the idea isn’t viable. Many fail because the founders quit. Spenser shared some eye-opening statistics: one-third of Y Combinator startups experience major co-founder conflicts, and even among successful SaaS companies, most founders leave within 7-10 years. The drop-off rate is high, even for those who have “made it.”

So why is Amplitude still going strong? It comes down to resilience. Spenser and his team didn’t just build a great product; they committed to sticking it out, even when the logical choice seemed to be stepping away. That persistence made the difference.

What’s Next for Amplitude

For founders wondering if they should keep going, Spenser offers this advice: the key differentiator isn’t intelligence or product skills—it’s refusing to quit. Success compounds over time, but only if you stick around long enough to see it happen.

For more on Amplitude, check out their site at Amplitude.com or follow Spenser on X (@SpenserSkates). And if you’re building something and wondering if you should keep going, the answer might just be yes.

Until next time, this has been Keep Going.