Keep Going: A Podcast About Failure and Success 1o6d1

Most people don't think about engineering managers until something breaks. Code slows down. Tickets pile up. Meetings drag on. Then someone asks, “Who’s managing all this?” John Kennedy, CEO of Actual AI, knows that problem better than most. He’s building software for the people holding the tech world together — engineering managers who plan, coach, and report across teams but are often stuck doing it with duct-taped dashboards or a dozen browser tabs. I talked to John on Startup Show about why Actual AI isn’t just another dashboard or bot. It’s an agent. It sees code changes, turns them into business summaries, tracks developer velocity using Stanford-grade metrics, and cuts out the grunt work that usually drags teams down. Not by flooding your Slack with hallucinated code reviews, but by actually working — quietly, usefully, and consistently — in the background. He told me their biggest goal is giving engineering managers their time back. Not with chat prompts or half-baked integrations. But by building something custom-fit: a true system of record for real-time development. The endgame? Let managers coach their devs, not babysit them. It's not flashy. It's not buzzwords. But it’s exactly the kind of thing that matters if you’re trying to build something real and not fall apart halfway through. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.keepgoingpod.com/subscribe

This week on Keep Going, I talked to Trevor Longino from CrowdTamers, a repeat guest and someone who’s made a career out of iterating through failure. Trevor doesn’t just tolerate failure—he plans for it. He opens every client engagement with a $100 ad test that’s designed to fail. Why? Because failure, early and cheap, tells you what not to do. But here’s the thing: not everyone wants to hear the truth. Trevor ran a campaign that outperformed a client’s original messaging 4x. Clear win. But the client didn’t like it. It didn’t “feel” right. So they stuck with the version that made them feel safe—even if it performed worse. That moment stuck with me. Because you’re not just selling results—you’re selling change. And not everyone is ready to change, even when the data begs for it. Trevor also opened up about making hard calls: firing clients who weren’t a good fit, reshaping his business around what actually works, and letting team go—not because they weren’t good, but because the business had changed. It’s the quiet, unglamorous side of running something real. This episode is about that: seeing failure not as a single moment, but as a sequence. What you learn one month after the fall isn’t the same as what you learn a year later. Founders keep going not because they win every time—but because they’re willing to look hard at what didn’t work and move anyway. Listen in. And if you’re in the middle of a shift—or thinking about giving up—maybe this is what you need to hear today. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.keepgoingpod.com/subscribe

Most of us don’t think twice about how we use computers. We move a mouse, type in a form, click a button. We’ve built up decades of patterns and habits, and the machines have evolved to meet us halfway. But what if the next evolution wasn’t a new interface—but the same one, just used by something that’s not us? That’s what Ang Li is working on. He’s the co-founder and CEO of Simular, a company building what he calls “autonomous computers.” His idea isn’t about adding more APIs or building smoother backends. It’s about making software agents that interact with the machine exactly like we do—by moving a mouse, typing into boxes, and navigating the graphical interface. Agents that act like us, but aren’t us. The conversation stuck with me. Partly because of the tech, which is impressive—they’re outperforming OpenAI in UI automation benchmarks. But mostly because of the philosophical weight behind what he’s building. The name Simular says it all. This isn’t human intelligence. It’s something like it. Something that mimics, that reflects. Ang comes out of DeepMind, where he split his time between AGI research and product engineering. That tension—between theory and practice—is exactly where Simular sits. They open source their tools. They build in public. They’re not trying to lock the future into a closed-loop platform. They’re trying to make it usable now, by anyone. What stuck with me most was his answer to the problem of trust. Most AI startups talk about full automation—hand over your tasks, and the machine will handle it all. But Ang is honest: no one is giving their Gmail to an agent. No one is giving it their credit card. So instead of pretending the agent can do it all, Simular is building a shared workspace. You and the machine work together. You do the sensitive stuff. It handles the rest. There’s something oddly human about that. Maybe AGI doesn’t come in a wave. Maybe it doesn’t look like a breakthrough. Maybe it looks like a computer that clicks and types, just like we do. And maybe that’s the future: a machine that isn’t better than us, just similar. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.keepgoingpod.com/subscribe

NOTE: This podcast discusses adult themes but we are careful not to describe too much. It’s mostly about tariffs. Every founder hits a wall. For Brian Sloan, the guy behind AutoBlow—a high-tech, internet-connected sex toy for men—that wall came in the form of a 145% tariff. This wasn’t his first rodeo. He’s been in the game 16 years. He lived in China, built deep relationships with his factory, and figured out how to bring a niche product to a mainstream customer. He knew his margins. He knew his risks. And still, he got crushed. Here’s what happened: thanks to a sudden tariff shift, his previously duty-free product category was now facing taxes that could double the cost of importing his goods. A $200,000 container would now cost $300,000 just to get into the U.S. That’s before selling a single unit. Keep Going - A Guide to Unlocking Success is a reader-ed publication. To receive new posts and my work, consider becoming a free or paid subscriber. The kicker? The news didn’t arrive with much warning. So he kept selling—at a loss—hoping the situation would resolve before the next shipment landed. It did. Barely. But not without cost. Retailers got nervous. Canadian buyers stopped ordering. Every day became a spreadsheet nightmare of gambling on timing, cash flow, and broken policy. Sloan didn’t ask for pity. He explained what actually happens when tariffs hit: they don’t hurt China. They hit American businesses, ones that design and market their products here but manufacture abroad—because that’s the only place where it’s still possible to make things at the price U.S. consumers expect. His factory wasn’t some faceless government proxy. It was a group of engineers, workers, and line managers he knew personally—folks who already operate on slim margins. And the alternatives? Absurd. Building in the U.S. means paying someone to solder cheap electronics for a product that might retail for $100. Nobody’s doing that profitably. Even now, with tariffs scaled back to 30%, the damage is done. Sloan raised prices. He’ll survive. But others won’t. Promotional goods sellers, housewares manufacturers, small operations locked into pricing contracts—this could wipe them out. This wasn’t a tech story. It was a survival story. And in a moment when supply chains are weaponized and manufacturing is politicized, Sloan’s message was simple: we’re not bad guys. We’re just trying to make things people want at prices they can afford, and if the rules change overnight, the entire system breaks. He made it through. Barely. And he came on Keep Going to talk about it not because he wanted to complain, but because he wanted people to understand: behind every line of policy, there’s a real business hanging on by a thread. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.keepgoingpod.com/subscribe

I spoke with Bille August recently, and what struck me most wasn’t just his long, decorated career as a director, but the way he described why he’s still doing it. After nearly 45 years, he’s not chasing relevance or acclaim. He’s chasing those short, fleeting moments of magic on a set—when everything clicks, when the actors and script and crew fall into rhythm—and you know it can never be repeated. Bille was born in a small town in Denmark in 1948. He’s been working in film for more than 40 years. He’s directed major international films—Pelle the Conqueror, The Best Intentions, The House of the Spirits, Night Train to Lisbon. He’s won just about everything: the Palme d’Or twice, an Oscar, Golden Globes, European Film Awards. But he doesn’t really talk about that. He talks about preparation and the importance of empathy. “Because we all have empathy, don’t we? We should have at least. It’s a big quality in human beings,” he said. Bille started out as a still photographer. That taught him to see the world in images. What he does now—cutting together emotions, stories, visual beats—is just an extension of that early training. When things go wrong, and they have, he its it hurts. But what keeps him going is the joy of making something meaningful from simple, honest work. "Don't make it too complicated," he said. "Be honest. Be prepared. Focus on the moment." His new film The Kiss is about what happens when pity gets tangled up with love. It’s the kind of story that could fall apart under a heavy hand, but Bille’s approach is always clear: follow the emotion, trust the people you’re working with, and that storytelling is just another way to remind ourselves what it means to be human. The advice he gave to new filmmakers applies just as well to anyone trying to build something: start simple. Be real. Don’t pretend. Prepare. And if you’re lucky, one day, someone will see what you made and feel like it was made just for them. That's the goal. That's the reason to keep going. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.keepgoingpod.com/subscribe

This week on Keep Going, I talked with Benjamin Wallace — author of The Billionaire’s Vinegar and, more recently, The Mysterious Mr. Nakamoto. We didn’t focus on plot or spoilers. Instead, we talked about what it means to write for a living right now, in a world that’s drowning in content and racing toward automation. Wallace is one of those writers who makes it look easy. But he’s honest: it’s not. The platforms to publish are wide open — Substack, blogs, self-publishing — but the traditional paths are narrower than ever. “It’s never been easier to publish whatever you want at any length and have worldwide distribution,” he said. “But the establishment publishing industry has never been more challenging.” We talked about the current game: you need a platform, a built-in audience, or a topic that breaks through the noise. Wallace started the Bitcoin book in 2022, when the crypto boom made it look like a broader audience was finally ready for it. Then AI exploded and sucked all the air out of the room. So why keep going? “You get a book deal,” he said, half-joking but mostly not. That deal lets you take the risk. It lets you focus. Without it, the economics just don’t work. Still, Wallace emphasized that anyone can start. His advice for new writers: don’t wait. Don’t be precious. Start a Substack, write the thing in public, and test what lands. And don’t use AI to write your pitch. “The book proposal is where you need to show what you can do,” he said. “If your pitch is written by AI, the assumption is the book will be too.” We dug into the question of AI and authorship. Could a bot have written The Billionaire’s Vinegar or Mr. Nakamoto? Probably not. “Weird books get written because someone has a weird obsession,” Wallace said. That human weirdness — that accident — is what makes good work good. AI can mimic quirks. It can’t originate obsession. This was a good conversation about what it means to write for a living right now. No hype. No hustle culture. Just a working writer telling the truth about the process. The Mysterious Mr. Nakamoto is out now. If you’ve ever wondered who Satoshi was — or what it takes to chase a mystery that might not want to be solved — it’s worth a read. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.keepgoingpod.com/subscribe

Founded by journalist and engineer Arikia Millikan, CTRL+X is a startup building a blockchain-based licensing system to help independent journalists protect, distribute, and monetize their work. Millikan started working on the idea nearly a decade ago, when she saw firsthand how media companies neglected digital infrastructure and treated editorial content as disposable. With the collapse of legacy media and the rise of AI, she believes protecting original journalistic content is more urgent than ever. "We're at a fork in society — pre-AI and post-AI — and the value of archival journalistic content is only going to rise," Millikan said. "If we don't enable journalists to protect their assets now, they’ll either rot or be stolen." Keep Going - A Guide to Unlocking Success is a reader-ed publication. To receive new posts and my work, consider becoming a free or paid subscriber. The Problem CTRL+X Tackles As traditional outlets shed staff and shutter archives, independent journalists are left without meaningful ways to preserve or profit from their work. Meanwhile, tech companies and AI models scrape old content for free, without rewarding creators. CTRL+X addresses this by offering journalists direct ownership and control over their archives. Unlike previous attempts that focused on ads, micro-tipping, or NFTs, CTRL+X uses blockchain to licenses for each piece of content. The text itself stays encrypted off-chain, while access is managed through token-gated systems. This structure keeps control in the hands of the journalist — not a platform. "It's the license for the content that's going on-chain," Millikan explained. "The text stays encrypted and protected. Journalists maintain access control, not some platform." Why Now? Technological barriers that once kept journalists away from blockchain are falling. Embedded wallets and easier-to-use Web3 tools mean that s no longer need deep crypto expertise to participate. Millikan sees this as the right time to bring CTRL+X to market, offering a "gateway" into Web3 for people who care about ownership and sustainability rather than financial speculation. How It Works Journalists first and license their archived work, protecting it against deletion or loss. Once archived, they can sell or license their content through the CTRL+X marketplace, receiving micro-payments directly into custodial Web3 wallets. "We're building the marketplace now — like a better Google Reader," Millikan said. "Every time a reader unlocks an article, a small payment flows back to the journalist. No subscriptions, no platform skimming half the money." The system is designed to be peer-to-peer. Even if CTRL+X were to shut down, s would still retain control of their content on the blockchain. "Unlike Apple or any centralized service, Control X is built so the creators keep ownership forever," Millikan said. "Even if we vanish, the content doesn't." The VisionMillikan imagines a future where journalists can back up their life's work securely, unlock new revenue streams from their archives, and rebuild a reading ecosystem outside of today's fractured paywalls and ad-driven models. "I've seen so much abuse in the journalism industry — people working their whole lives just to have their work forgotten or mined for free," she said. "I decided to dedicate my living energy to chipping away at this problem until I die." CTRL+X just launched its MVP and is now live at CTRLX.world. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.keepgoingpod.com/subscribe

This week on Keep Going, I sat down with Scott Stevenson, CEO of Spellbook, a company that started with a frustrating legal bill and turned into one of the most widely used AI tools in the legal world. Scott’s story isn’t a straight line. He started building video games. Then musical instruments. None of them took off. But what stuck with him was the pain of trying to build something creative and getting hit with sky-high legal costs. Instead of walking away from that experience, Scott leaned into it. He co-founded a company called Rally that evolved into Spellbook—now used by over 3,000 legal teams in more than 50 countries. If you've ever used GitHub Copilot, Spellbook is basically that for lawyers. It handles the repetitive stuff, helps draft documents, and is now expanding into what Scott calls "AI colleagues"—agents that can review and manipulate whole sets of legal documents across a transaction. What stood out in our conversation was Scott’s willingness to chase hard problems. He said the turning point came when they stopped trying to make something flashy and started looking for work people actually needed. He and his team launched more than 100 product variations before finding one that clicked. They didn’t overspend. They didn’t force the market. They waited for the moment when s started grabbing the product out of their hands. And when it came, it came fast—30,000 s in three months. We also talked about art, creativity, and the tradeoffs that come with trying to make something lasting. Scott still wants to make music. Still wants to build games. But for now, he’s building tools that just might change how the legal system works—from bloated contracts to data-driven negotiations. If you’re stuck, if you’re wondering whether the thing you’re building is really worth it, Scott’s advice is simple: Find a real problem. Stick with it. Wait for the water to start moving fast. You’ll know it when you see it. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.keepgoingpod.com/subscribe

I’ve been working on a book called Shroomies—a straightforward look at how mushrooms are helping people. Not the flashy kind of help. The real kind. People coming off SSRIs. People showing up for their kids. People ing how to laugh again. When I started talking to Tracey Tee, founder of Moms on Mushrooms, I realized this conversation was exactly the kind of thing that should be on Keep Going. Her story is personal. She lost a business during COVID, hit the wall like a lot of us did, and then got introduced to mushrooms by a friend on a camping trip. Not in a “woo” way. In a “what if this actually helps” way. What Tracey built in response is impressive: a digital community with thousands of paying , all moms, all learning how to safely and intentionally use psychedelics—mostly microdosing psilocybin. No Bali retreats. No ceremonies in the jungle. Just a framework to help women understand what this medicine is, how it affects their brains, and whether it might be a better alternative to nightly wine or overprescribed meds. The most interesting part? They're not pushing protocols. No “take this much at 7 a.m. and wait.” Tracey calls it “intuitive microdosing.” You learn how it works in your body, you learn your why, and you stay grounded in community while doing it. We talked about moms who wanted to feel fun again. Who were grieving. Who were creative and didn't what it felt like to make something just for the hell of it. There’s also research starting to emerge on psilocybin and female hormonal health—everything from postpartum to menopause. This episode is a reminder that healing doesn’t have to come from a bottle with a label. That psychedelics might have a place in day-to-day life, especially for those carrying the mental load of families, careers, and the general madness of being alive right now. Listen to the full conversation on Keep Going. Tracey Tee is doing serious work here. You don’t have to believe in all of it, but you should hear it out. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.keepgoingpod.com/subscribe

This week on Keep Going, I sat down with Richard White, founder and CEO of Fathom—the AI note-taker built for the flood of Zoom, Meet, and Teams meetings we all sit through. Fathom was early. It launched back in 2021 before the LLM boom, betting that AI would get better and note-taking would become table stakes for knowledge work. They were right—but it didn’t feel like that at first. When they debuted on the Zoom app marketplace, they picked up nearly 100,000 s in a month. Sounds like a dream, right? But that wave of attention turned into a near-death moment for the team. Out of those 100,000 s, just 100 were active. Total. For a while, it looked like they’d built something nobody wanted. So what happened? And how did they fix it? Lesson #1: Not all s are equal. It turned out most of those early s weren’t the right s. Many didn’t have a single meeting scheduled when they ed. COVID-era Zoom meant folks were using it to call their grandparents or attend virtual happy hours. Most of those who clicked “install” had no real use case. The team realized that their onboarding funnel didn’t filter for quality—and that was the problem. Lesson #2: Filter hard, even if it shrinks your numbers. They added friction. The flow got longer. They started blocking s from personal emails, pushing low-quality s to waitlists, and asking for proof of usage—like syncing a work calendar or ing a test call. That worked. The active count went up, not because of more traffic, but because the traffic was better. Richard put it clearly: “I'd rather someone have no opinion than walk away thinking the product didn’t work for them.” Keep Going - A Guide to Unlocking Success is a reader-ed publication. To receive new posts and my work, consider becoming a free or paid subscriber. Lesson #3: Bad onboarding is worse than no onboarding. The team also realized their onboarding process wasn’t helping people succeed. Instead of stripping everything down to make it easier, they actually added steps—but ordered them carefully. They drew inspiration from video games: start easy, build confidence, then ask for more. This gave s a sense of momentum and kept them engaged through the setup process. As a result, their activation rates climbed from 30% to 80%. Lesson #4: Use the wrong s to get better. Ironically, those low-value early s became a gift. They weren’t ideal customers, but their volume gave the team the data they needed to refine their flows. They learned how to stress-test the funnel and got better before the real flood of quality s arrived. Lesson #5: AI is finally catching up to the vision. Now, Fathom is doing what it always wanted to do. Its AI can summarize meetings better than most humans. Soon, it won’t just take notes—it’ll understand what’s happening across all your meetings. It’ll tell you who got upset, what topics keep coming up, and which conversations need follow-up. In other words, the AI is starting to understand context. And that’s the next frontier. Richard’s vision is simple: “Let AI do the pre- and post-meeting work, and let you skip the meetings you don’t need to be in.” That means fewer meetings, better decisions, and searchable, usable knowledge across your company. Keep Going Takeaway:The lesson from Fathom is about the long game. It's not just about getting people to try your product. It's about getting the right people to try, and giving them the best possible shot at success. That takes friction, patience, and willingness to ignore the vanity metrics. You can check out Fathom at fathom.video. No special links. Just five carefully designed steps. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.keepgoingpod.com/subscribe

In this week’s Startup Show, I talked to Quinn Kwon from Delabs Games. She’s helping rethink how we make, launch, and grow games. And it doesn’t look anything like the traditional model. Instead of throwing money at ads on Google or Facebook, Delabs is building games that grow inside messaging platforms—Telegram, Line—and reward s directly for helping spread the word. This is Web3 gaming, but without the jargon. It’s about incentives. It’s about community. And it’s about meeting players where they already are. Their newest game, Boxing Star X, launched on Telegram and Line, two apps people are already using every day. No installs. No s. Just a link, a tap, and you’re playing. Since February, they’ve pulled in over 700,000 s. Not from ad budgets, but from shared links and organic network effects. The idea here is simple: marketing budgets should go to players, not platforms. If someone brings a friend into a game, why shouldn’t they be the one who gets rewarded? Delabs is doing that through token rewards and referral incentives, but they’re also trying not to let that mechanic overpower the game itself. If the only reason people show up is to earn 50 cents, the game dies fast. There’s a tension here between financial motivation and creative integrity. Quinn’s clear-eyed about that. Right now, most of Web3 gaming still leans speculative. But they’re working to build systems where both types of players—the ones who play to compete and the ones who play to earn—have a place in the same ecosystem. It’s also a reminder that markets are different. A $1 reward might mean nothing to a U.S. player. But in other regions, it’s a real incentive. That shapes behavior. And Delabs is deg with that in mind, from leaderboards for high-spenders to basic play modes that reward steady, daily engagement. What stood out to me most was how they’re building games like Boxing Star X not just as entertainment but as a community layer inside existing social platforms. There’s no jump from app store to app. The game lives where the people already are. And the reward system is built into that layer—native, social, and real-time. For game developers, especially indie studios, this offers a playbook that sidesteps the algorithm arms race. For players, it’s a signal that gaming can feel less extractive. And for anyone paying attention to where the internet is going—especially at the edges of tech and culture—it’s a case study in how things might grow from the bottom up instead of top down. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.keepgoingpod.com/subscribe

This week on Keep Going, I sat down with Judy Kadylak. She’s a leadership coach who works in psychedelic integration. That sounds like two different jobs, but she’s found something interesting in the overlap: people trying to lead others without knowing how to sit still with themselves. Judy’s focus lately has been on dopamine. Not the abstract brain science stuff, but the actual patterns we fall into when we’re hooked on cheap rewards—scrolling, snacking, constant stimulation. She started noticing it in her clients. Then in herself. Social media was rewiring her days. So she tried a detox. Not the biohacking kind. Just a hard pause on the hits: no phone in the morning, fewer distractions during the day. It worked. It changed how she felt about work, motivation, and focus. She started building it into her coaching—especially for clients who wanted to use psychedelics as part of their growth. She found that without cutting down the dopamine noise, even a solid psychedelic session could feel flat. The insights didn’t land. The breakthroughs didn’t stick. Now she’s running a group program around the detox idea. It’s a month long. It starts simple—don’t touch your phone for the first hour of the day. She says that alone can change how your brain handles reward for the rest of the day. Most of her clients don’t come in meditating or reflecting. But a week or two in, they start to. Judy's not militant about it. She doesn’t tell people to quit social media. She helps them figure out their triggers and build space between the trigger and the habit. The point isn’t to eliminate pleasure. It’s to reset how we relate to it. If you’re interested in her program, check out judykadylak.com. I’m still not sure I’m ready to give up my morning scroll. But Judy makes a strong case for at least trying. We can’t talk about leadership or growth if we’re afraid to sit still. And maybe we’re not failing—we’re just running low on quiet. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.keepgoingpod.com/subscribe

When Jonathan Lowenhar says he enjoys his work, he means it. He’s the founder of Enjoy the Work, a firm that helps startup founders grow into actual CEOs. Not “founders who can speak on s,” but operators—leaders who can run companies with hundreds of employees and real stakes. I had him on Keep Going to talk about what happens when the startup dream gets real—and why so many founders hit a wall once they find early success. Startups begin with an idea. A spark. A product that someone has to build. But if it catches on, suddenly the job changes. “The market gives a s**t,” as Jonathan puts it. And now you’ve got to run a company. That’s where things break down. A lot of founders want to build the next Spotify or Airbnb but haven’t thought about what it takes to lead 100 or 1,000 people. Jonathan runs a thought experiment: How would you run a company with 100 employees? Most founders have no answer. That’s the gap Enjoy the Work tries to fill. His firm doesn’t work with everyone. They only work with founders who want to get better. Not the ones who think they need a handyman to fix a broken team. They work with the ones who want coaching, , and change. One story he told stood out: a founder who wanted total control. He ran a climate tech startup with about 100 employees. His idea of management? A weekly spreadsheet detailing what every person should be doing. Engineers, PMs, executive assistants—everyone got orders. Two weeks in, everyone hated it. It didn’t work. So Jonathan asked him, “Do you want to be right, or do you want to win?” That’s the question at the heart of all this. Control feels safe. But real leadership is about trust. You don’t scale a company by acting like a parent to 100 kids. You hire adults. You lead, you don’t command. They worked with his leadership team to change things. Moved from top-down control to clarity, autonomy, and purpose. Set goals, built systems, gave people the tools and trust they needed. Jonathan sees the same patterns again and again. Founders stuck in fear mode. CEOs building companies around themselves instead of their customers. Startups built to please “the audience of one.” Fear is a bad decision-maker, he says. It’s what leads to wild overcorrections, micromanagement, and burnout. The fix isn’t therapy (though maybe that too). The fix is building actual strategy. What does winning look like? What could kill the company? What can be fixed? And most of all: what does the founder need to stop doing? That’s where many crash. A product-focused founder hides in code. A sales CEO just hops on more calls. Jonathan’s advice is simple: your calendar reflects your priorities. If you’re spending your time in the wrong places, the company suffers. There’s one more thing he said that stuck with me. Startups often fail not because of murder, but because of suicide. Founders kill their own companies. Not on purpose—but by refusing to adapt. By avoiding the hard work of learning how to lead. So what’s the goal of Enjoy the Work? To help founders grow into leaders before the board replaces them. To give them the tools to not just start something great, but run it all the way to the end. If you’re a founder—or even thinking about starting something—listen to this one. Then ask yourself: are you doing the job, or getting better at the job? This is Keep Going, a podcast about success and failure. I’m John Biggs. See you next week. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.keepgoingpod.com/subscribe

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 Roap 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). This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.keepgoingpod.com/subscribe

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 s, 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 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. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.keepgoingpod.com/subscribe

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 s, 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 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.

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, ed 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 s, and Oura—yes, that Oura, the sleep-tracking ring company—reached out. Instead of , 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.

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.

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 Experiment Shereen’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 Happiness For 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 ed, 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 Going At 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 with retention, engagement, and burnout. So the question isn’t “Should we focus on kindness?” The question is “Can we afford not to?” If you want to learn more, check out bekindr.org—and maybe start thinking about how a little kindness could go a long way in your own company. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit keepgoingpod.com/subscribe