Startups are a grind. Hardware startups? Even tougher. This week on Keep Going, I sat down with CrackBerry Kevin (aka Kevin Michaluk), the guy who made BlackBerry blogging a thing, sold a media empire, and then jumped back into the game—this time with a physical product: Clicks, a BlackBerry-style keyboard for modern smartphones.

Kevin built CrackBerry.com in 2007, turning it into the go-to site for BlackBerry enthusiasts. As BlackBerry rose, so did CrackBerry. As BlackBerry fell, well... Kevin was there for that too. He expanded into a broader media company with sites like Android Central and iMore, eventually selling the business in 2019. After a few years locked out of content due to non-competes, he got the itch to build again.

That led him to Clicks: a physical keyboard for iPhones and now Android devices. The idea? Bring tactile typing back to smartphones without building an entirely new phone. The concept was simple, but making it a reality was anything but.

Clicks exploded at CES 2024. Kevin and his team didn’t just launch a product; they stole the show. While CES has lost some of its luster, Clicks grabbed attention. Why? Nostalgia, simplicity, and an easy-to-understand pitch: "What if you could add a real keyboard to your iPhone?" That, plus years of media experience, meant they knew exactly how to get the right people talking.

Kevin says he wants to change the startup mantra from "hardware is hard" to "hardware is life." There are endless challenges: supply chain delays, manufacturing headaches, and constantly updating for new phone models. But the real grind? Figuring out how to scale smartly without burning through cash too fast.

The Clicks team didn’t raise big venture money right away. Instead, they took a measured approach, building momentum before bringing in outside investors. They avoided the trap of raising too much, too soon, and burning through it before fully understanding their market.

Clicks is now expanding beyond iPhones to Android devices, including a version for the Motorola Razr Flip. They’re also thinking beyond keyboards, looking at how cases can be smarter and more useful. The goal? To build a consumer tech brand that sticks, not just a one-hit wonder.

Kevin’s biggest takeaway from his years in media and now hardware? Know when to push forward, but also when to pivot. His first post-BlackBerry venture, a wellness supplement brand, didn’t work out. That failure made him double down on what he knew: differentiated products with a built-in audience.

If there’s one thing Kevin embodies, it’s persistence. From blogging to hardware, he keeps jumping into the deep end, learning as he goes. Whether Clicks becomes a household name or just a cult favorite, one thing’s clear—he’s not stopping anytime soon.

For more, check out Clicks or follow Kevin on X (@CrackBerryKevin).

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.