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.

From BlackBerry to Clicks

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.

CES and Going Viral

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.

Hardware is Hard—But It’s Also Life

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.

The Roadmap Ahead

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.

Lessons from a Serial Founder

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.

Keep Going

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).

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.