Startups are hard. 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.

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.

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.

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.

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.

I’ve interviewed hundreds of founders, but this was a first—I talked to a married couple who built a business together. Lisa and Paul Juris, founders of Somo Sleep Fitness, joined me on The Startup Show to talk about their sleep mask that does more than just block light.

The idea started with a simple problem: light disrupts sleep. But Lisa and Paul went deeper. They found that 63% of people struggling with sleep weren’t just dealing with light pollution—they were battling stress, anxiety, and an inability to shut off their brains. Instead of adding tech, apps, or wearables, they looked at acupressure.

Their mask applies gentle pressure to the yin-tong acupoint, the spot between your eyebrows that has been clinically linked to reducing stress. It’s the same pressure point used in hospitals like Memorial Sloan Kettering and Mass General to help patients relax. With a patent in hand, Lisa and Paul focused on making their product better—comfortable, adjustable, and built for real-world use.

Then came the moment every founder dreams of. They sent samples to a few industry contacts, and Oura—yes, that Oura, the sleep-tracking ring company—reached out. Instead of feedback, Oura placed an order for 6,000 masks. They wanted to include it in their global referral program, and suddenly, Somo Sleep Fitness wasn’t just a side project. It was a business.

With no outside funding, Lisa and Paul had to figure everything out—manufacturing, logistics, global fulfillment—on the fly. They didn’t just make it work, they built things methodically using the skills they gained over long careers. They hustled, adapted, and stayed focused on what mattered: making a product that people actually love to use.

And that’s the key. When people start tracking their sleep with an Oura ring or Apple Watch, they see the difference. Athletes, parents, travelers, even an entire national soccer team have adopted the mask. Customers send messages at all hours asking for replacements after losing theirs. Parents buy extras after their kids steal them.

Now, Lisa and Paul are expanding. They’re working on a version for kids—because, apparently, 76% of parents are giving their children melatonin just to get them to sleep. They’re also exploring more acupressure-based products for recovery and performance.

Their story is the best kind of startup story. They didn’t set out to raise millions or chase hype. They found a problem, solved it in a way that actually works, and built something that people genuinely love. They stayed flexible, embraced learning, and never let setbacks stop them.

Mark Rizzn Hopkins didn’t set out to be a cautionary tale. He was deep in the crypto world, doing what thousands of others were doing—buying and selling Bitcoin. But one transaction, involving a client unknowingly caught in a scam, put him under federal scrutiny. A missing FinCEN form, a technicality buried in new regulations, led to a raid, a legal battle, and ultimately, a year in federal prison.

For most people, that would be the end of the story. But Mark didn't give up.

Prison changes people. You spend your time thinking about the little things you took for granted—a shower at the right temperature, a mattress with more than a half-inch of padding, a handshake with a friend. When Mark got out, he didn’t waste time. He had already mapped his next steps. He knew his career in mainstream industries was over, so he leaned into the one space that would take him back—crypto.

But Mark’s story isn’t just about rebuilding. It’s about seeing the system for what it is. He went in believing he was one of the few who got caught up in something unfair. He came out realizing that the entire prison system is filled with people like him—people who made small mistakes, people who were in the wrong place at the wrong time, people who got chewed up by a system that needed numbers more than it needed justice.

Instead of running from it, he stepped into advocacy. He worked with Free Ross DAO, a group pushing to free Ross Ulbricht, the founder of Silk Road. Through a mix of activism and unexpected connections—including a conversation with Donald Trump—Mark became one of the voices pushing for Ulbricht’s release. And it worked. Ross didn’t just get a commutation—he got a full pardon.

Mark’s story is about more than Bitcoin or prison or politics. It’s about resilience. About how, when the world decides to knock you down, you decide whether you get back up. He’s not asking for pity. He’s not trying to erase what happened. He’s just showing up every day and doing the work. Because that’s what you do.