Keep Going

John Biggs
Keep Going

When you're going through Hell, keep going." This is a podcast about failure and how it breeds success. Every week, we will talk to amazing people who have done amazing things yet, at some point, experienced failure. By exploring their experiences, we can learn how to build, succeed, and stay humble. It is hosted by author and former New York Times journalist John Biggs. Our theme music is by Policy, AKA Mark Buchwald. (https://freemusicarchive.org/music/policy/) startupstrats.substack.com

  1. 1D AGO

    Keep Going: Why hardware is hard

    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).

    32 min
  2. MAR 17

    Keep Going: The hardest choice in startups

    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. 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.

    16 min
  3. MAR 12

    Startup Show: An off switch for your brain

    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.

    17 min
  4. MAR 10

    Keep Going: How to survive federal prison

    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.

    27 min
  5. MAR 6

    Keep Going: How one comedian almost had it all

    On this episode of Keep Going, I talked with Dan White—comedian, writer, and self-described "improv pervert"—about failure, creative perseverance, and that time he came this close to being Jake from State Farm. Dan is one of the funniest people on Twitter, and I brought him on because, frankly, I needed some joy in my life. But as it turns out, his story is as much about resilience as it is about humor. We dug into what it's like to chase success in a creative field, deal with setbacks, and somehow keep pushing forward even when the world (or a national focus group) tells you no. Failure, but Make It Funny Dan’s journey started in competitive sports, running track in high school and college. In that world, success is easy to measure—you either ran faster than the next guy, or you didn’t. But in comedy and acting, there’s no clear metric. You can crush an audition and still not get the part. You can write a brilliant joke and watch someone else go viral for something worse. His biggest almost moment? He was one of the final contenders to be the new Jake from State Farm—a gig that would have been life-changing financially. He nailed the audition, had an inside connection, and waited through the holidays thinking maybe, just maybe, this was his big break. Then, in January, the email came: "Not gonna be this one. Good luck." The worst part? State Farm did a focus group, and apparently, America overwhelmingly preferred the guy who got the role. Imagine losing out on millions and having it publicly confirmed that the entire country thought you just weren’t quite right. If that wasn’t brutal enough, years later, a friend casually mentioned that the guy who landed the gig was also a massive ladies' man in college. Just one more reminder that life isn't fair.

    31 min
  6. Keep Going: How to be kind

    FEB 17

    Keep Going: How to be kind

    The workplace isn’t exactly known for being a warm and fuzzy place. Stress, pressure, and the relentless pursuit of profit usually take priority over things like employee happiness. But what if that’s the wrong approach?On this episode of Keep Going, I talked to Shereen Eltobgy, the Chief of Belief at Kindr Workplaces—a new initiative that aims to make kindness a core part of company culture. It sounds idealistic, but it’s rooted in hard science. Studies show that happier employees lead to better productivity, stronger customer relationships, and ultimately, more successful companies. So why aren’t more businesses making this a priority?The Zappos ExperimentShereen’s journey into workplace happiness started in an unlikely place—Zappos. Before it became an e-commerce giant, Zappos was just another online shoe retailer. But under Tony Hsieh’s leadership, the company made a radical bet: culture matters. Employees weren’t just workers; they were part of something bigger. Their values were aligned with the company’s mission, and their well-being wasn’t an afterthought—it was the strategy.The results were undeniable. Zappos employees weren’t just showing up for a paycheck—they believed in what they were building. And happy employees translated into happy customers, which translated into serious business success.That’s what Kinder Workplaces is trying to replicate: a workplace culture where people don’t just survive—they thrive.Can Kindness Scale?This is where most skeptics come in. It’s easy to build a strong culture when you’re a small, fast-growing company like Zappos was in its early days. But what happens when you’re a legacy company that’s been around for 50 years? What happens when your employees are there just to collect a paycheck?According to Shereen, it’s possible—but it starts with leadership. She’s seen firsthand how large organizations, including a 60,000-person healthcare company, completely transformed by prioritizing connection, resilience, and empathy. The CEO led the charge—not with empty buzzwords, but by actually showing up for employees, making culture a company-wide priority. The result? A massive jump in customer satisfaction and engagement.The Business of HappinessFor years, companies have talked about employees being their greatest asset. But when times get tough, that’s often the first thing that gets ignored. Stress and burnout are treated as unavoidable side effects of high performance. But the research—and real-world case studies—prove otherwise.When people are engaged, valued, and supported, they work harder, innovate more, and stay longer. It’s not just good for morale—it’s good for business.Shereen calls it mindful kindness—a structured, intentional way to integrate kindness into leadership, communication, and even sales. It’s not about random acts of kindness. It’s about changing how companies operate from the ground up.How to Start (Without Losing Your Edge)For founders, CEOs, and managers who think this all sounds nice but impractical, Shereen offers a reality check: kindness doesn’t mean weakness. It doesn’t mean ignoring deadlines or letting things slide. It means leading in a way that brings out the best in people.Some simple, actionable ways to start:* Reduce judgment—on yourself and others.* Speak more kindly—to employees, customers, and even competitors.* Prioritize well-being—physical, mental, emotional. Happy people work better.* Shift the bottom line—not just profit, but the human bottom line.It’s a mindset shift, and it’s one that more companies are starting to embrace.Keep Growing, Keep Glowing, Keep GoingAt the end of our conversation, Shereen left us with a simple mantra: keep growing, keep glowing, keep going.The world is changing. AI is automating tasks, traditional hierarchies are breaking down, and employees want more than just a paycheck. They want purpose, connection, and meaning.Companies that figure this out will win. The ones that don’t? They’ll keep struggling wit

    22 min
  7. FEB 10

    Keep Going: How to breathe (plus a bonus breath work session at the end of the episode)

    On this week’s episode of Keep Going, I spoke with Hannah Cohen, a somatic coach and transformational guide specializing in breathwork and sound healing. In today’s world of relentless pressures, both personal and professional, Hannah’s work offers tools to navigate the noise and reconnect with the body and self.Creating Space to BreatheHannah believes the first step to finding balance is carving out intentional time away from technology and daily distractions. By grounding yourself—placing your feet on the earth or simply tuning into your breath—you create the opportunity to reconnect with your inner world. This practice, she says, can help anyone, from high-pressure CEOs to individuals overwhelmed by today’s constant stream of news and demands.CrankWheel is a 10x simpler screen sharing solution, tailor-made for sales professionals. Add a screen sharing presentation to your sales call in 10 seconds flat. Your prospect clicks a link that you send by text message or email and immediately sees your presentation - no download or registration, even on their mobile device. Breathwork is at the core of Hannah’s practice. She highlights techniques like holotropic breathing, which involves a pattern of deep breaths into the belly, chest, and then a release. This method can activate the vagus nerve, calm the nervous system, and allow for emotional release. Hannah encourages journaling after these sessions to reflect on patterns, themes, or emotions that emerge.The Power of SoundSound healing is another tool Hannah champions. Whether through humming, sound baths, or working with instruments like gongs or bowls, sound creates a space for energy release and self-exploration. She explains how sound can help process emotions like anger or grief, clear stagnant energy, and foster a deeper connection to the self.Hannah emphasizes that sound doesn’t have to be complicated. Simply listening to the wind in the trees, a favorite song, or even experimenting with your own voice can be powerful. For those looking to explore sound healing more deeply, she suggests seeking out local practitioners or group sound baths, which often create a shared space for healing and connection.Try SubMarket.pro to advertise in newsletters like this oneWant to tap into newsletter audiences without the usual affiliate hassles? Submarket lets you pay newsletter owners only when their readers actually click your links.No upfront fees. No complicated codes. Just direct access to engaged newsletter audiences and crystal-clear analytics on every click.Test it out - create your first link in under 60 seconds. Overcoming SkepticismFor those skeptical of these practices—or those who feel too busy to try—Hannah offers gentle encouragement. Even setting aside 10 minutes a day for focused breathing or listening to sound can make a difference. She notes that skeptics often find unexpected breakthroughs when they give these methods a chance, pushing past resistance and tuning into their body’s wisdom.A Practice of ConnectionHannah’s work is rooted in community and collaboration. Whether in group settings or one-on-one sessions, she values the collective energy and healing that comes from shared spaces. She reminds us that the journey toward wellness isn’t about perfection—it’s about small, consistent steps to honor the body and the present moment.If you’d like to explore Hannah’s offerings, including retreats and workshops, visit her website at feelingsfelt.com or find her on Instagram at @feelings__felt.She’s also offered a discount to join for a Breath of Transformation class at Reforesters Lab. The promo code is: HANNAHCOHENShe teaches every Tuesday at 6 PM at Reforesters Lab and every Thursday from 7:30-9 PM at Jivamukti. She is also available for 1:1 sessions.As Hannah says, “Healing happens together.” Whether it’s through a deep breath, a hum, or a moment of stillness, taking the time to reconnect with yourself can create the space to keep going.As a special bonus

    25 min
  8. Editor-In-Grief: Why journalism sucks right now

    FEB 6

    Editor-In-Grief: Why journalism sucks right now

    NOTE: This episode contains bad words.On the latest episode of Editor in Grief, Jim and I sat down with journalist and columnist Brian Karem to talk about the state of journalism today. Brian, a veteran reporter and host of Just Ask the Question, pulled no punches as we discussed what he calls "bend over and take it in the a** journalism."CrankWheel is a 10x simpler screen sharing solution, tailor-made for sales professionals. Add a screen sharing presentation to your sales call in 10 seconds flat. Your prospect clicks a link that you send by text message or email and immediately sees your presentation - no download or registration, even on their mobile device. Want to tap into newsletter audiences without the usual affiliate hassles? Submarket lets you pay newsletter owners only when their readers actually click your links.No upfront fees. No complicated codes. Just direct access to engaged newsletter audiences and crystal-clear analytics on every click.Test it out - create your first link in under 60 seconds. The Problem with Decorum JournalismJim kicked things off by defining what he calls "decorum journalism," where reporters avoid asking tough questions to maintain access, keep sources happy, or avoid backlash from fellow journalists. Brian took that further, arguing that the real problem is a mix of inexperience, access journalism, and corporate consolidation. The old model—where seasoned reporters asked tough questions and held power to account—is fading fast. Instead, we have newsrooms filled with younger, less experienced reporters who are hesitant to challenge authority.Brian pointed out that his mentors, Sam Donaldson and Helen Thomas, instilled in him the importance of asking questions—whether or not they get answered. “It doesn’t matter what the question is. It doesn’t matter if they answer it. It just matters that you ask it. That way you’ve put the issue on the record.”The White House Press Room: A Case Study in GroupthinkWe talked about how the White House press briefings have become performative. Brian recalled moments where reporters would speculate about what an official meant rather than just reporting what was actually said. That speculation would then turn into anonymous sourcing—one journalist repeating another's educated guess as insider information.He also shared stories about how institutional knowledge has vanished from the front row of the briefing room. Where there used to be decades of experience, there’s now a fraction of that, and it shows. “The problem in that briefing room is not just a lack of education, responsibility, and experience,” Brian said. “It’s the idea that you’ve never covered a beat before. You don’t know what the you’re doing.”The Real Cause: Corporate ConsolidationOne of the biggest threats to journalism, according to Brian, is the monopolization of media. Six companies control 95% of what Americans see, read, and hear. “We don’t have real journalism today. We have cheap entertainment.” He pointed out that newsrooms used to be filled with reporters who broke major stories, but corporate ownership and cost-cutting have gutted those institutions.Jim and I agreed. In our own experiences, we've seen vulture capitalists strip newsrooms for parts, cutting experienced reporters to save money while chasing profit margins that aren’t sustainable. The result? More clickbait, less investigative work, and a public that’s increasingly misinformed or disengaged.How Do We Fix This?Brian had a few ideas, and none of them involved waiting for billionaires to save us. He argued for breaking up media monopolies, providing tax incentives for local journalism, and supporting new models that prioritize actual reporting over entertainment.Local journalism, he stressed, is key. “There are 45% of the counties in this country that don’t have a single local news outlet. That means no one is covering city councils, school boards, or local government corruption.” Without local journalism, ther

    39 min

Ratings & Reviews

5
out of 5
6 Ratings

About

When you're going through Hell, keep going." This is a podcast about failure and how it breeds success. Every week, we will talk to amazing people who have done amazing things yet, at some point, experienced failure. By exploring their experiences, we can learn how to build, succeed, and stay humble. It is hosted by author and former New York Times journalist John Biggs. Our theme music is by Policy, AKA Mark Buchwald. (https://freemusicarchive.org/music/policy/) startupstrats.substack.com

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