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Keep Going episodes

  • Keep Going: Moms on Mushrooms, and Why Psychedelics Might Be the Next Wellness Tool for Burnt-Out Parents

    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 remembering 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 members, 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 remember 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
    24 min
  • Keep Going: The Danger of Easy Growth

    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 signups 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 users, 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 signups are equal.

    It turned out most of those early users weren’t the right users. Many didn’t have a single meeting scheduled when they joined. 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 signup flow got longer. They started blocking signups from personal emails, pushing low-quality users to waitlists, and asking for proof of usage—like syncing a work calendar or joining a test call. That worked. The active user 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.”

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    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 users 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 users to get better.

    Ironically, those low-value early users 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 users 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
    19 min
  • Startup Show: Rethinking Game Growth in the Age of Telegram, Tokens, and Real Fans

    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 users 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 logins. Just a link, a tap, and you’re playing. Since February, they’ve pulled in over 700,000 users. 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 designing 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
    16 min
  • Keep Going: Dopamine Detox and Why You Can’t Sit Still

    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
    15 min
  • Keep Going: How to Build a Real Company (Not Just a Cool Startup)

    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 panels,” 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, feedback, 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
    27 min
  • 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).



    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
    32 min
  • Keep Going: The hardest choice in startups

    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.



    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
    16 min
  • 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 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 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 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 www.keepgoingpod.com/subscribe
    23 min
  • 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 Breathe

    Hannah 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.

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    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 Sound

    Sound 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.

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    Overcoming Skepticism

    For 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 Connection

    Hannah’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: HANNAHCOHEN

    She 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, Hannah has created a 10 minute session for Brave Leaders! Hopefully it will help you and please reach out to her if you’re interested in her work.



    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
    25 min
  • 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."

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    The Problem with Decorum Journalism

    Jim 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 Groupthink

    We 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 hell you’re doing.”

    The Real Cause: Corporate Consolidation

    One 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, there’s no accountability, and without accountability, democracy suffers.

    The Bottom Line

    This conversation reinforced what many of us in journalism already feel—our industry is in trouble, and it won’t fix itself. The corporate owners of media don’t care about informing the public; they care about turning a profit. And as long as we continue prioritizing access over accountability, entertainment over investigation, and groupthink over independence, the situation will only get worse.

    Brian’s book, Free the Press, digs deeper into these issues. If you care about the future of journalism, it’s worth a read.



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    40 min

About Keep Going

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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,…