Keep Going

John Biggs
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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, 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/) www.keepgoingpod.com

  1. VOR 3 TAGEN

    Keep Going: Stop numbing yourself and start paying attention

    I sat down with Anne Karber and what struck me right away was not the résumé. Entrepreneur, author, podcast host, all of that is fine, but it is not the story. The story is what happens when you build a life that works on paper and still feels wrong when you wake up in it. She came up in construction, which is not a forgiving place. Long hours, constant pressure, and a culture that rewards output above everything else. She learned to operate in that mode early. Work harder than everyone else. Push through anything. Do not stop to think about how you feel because that slows you down. That approach got her success in the way most people define it. Money, stability, control. But it also trained her to ignore anything that did not fit into that system. Then her sister died, suddenly and without warning, and that kind of loss does not fit into a system built on control. It breaks it. What followed was not some dramatic collapse. It was something more common and more dangerous. She kept going, but she started numbing herself to get through it. Work during the day, drinking at night, and repeating that cycle until it became normal. Not chaos, just a steady flattening of everything that mattered. She described it in a way that is hard to ignore. You are not living your life at that point, you are anesthetizing it. You remove the parts that hurt, but you also remove the parts that make anything feel real. The problem is that it works, at least for a while. That is why people stay there. What changed for her was not some sudden moment of clarity. It was exhaustion with the pattern. She got to a place where she could not look at herself and feel any sense of pride. That is a low bar, but it is a real one. When you cross that line, something has to give. She went to rehab. She doubled down on therapy. She started doing things that sound simple and are anything but simple when you are used to avoiding yourself. Writing things down. Sitting without distractions. Paying attention to where her time and energy were actually going. Not where she thought they were going, but where they really went when she looked at it honestly. One of the sharper points she made is that energy is the only resource that really matters. Everyone talks about time, but time is not the issue. Energy is. You can spend hours doing something and feel fine, or you can spend twenty minutes on something that drains you completely. Most people never track that. They just move from one habit to another and assume it is all the same. She started treating energy like something that had to be accounted for. What gives it back. What takes it away. What is neutral. Once you see that clearly, you start to realize how much of your life is built around habits that do nothing for you. Endless scrolling. Drinking. Overworking. All of it framed as necessary, but none of it actually helping. There is a hard part here that she did not soften. You have to be honest about what you are doing. Not in a vague way, but in a direct way. If you spend three hours a day on your phone, you write that down. If you drink every night, you admit what that is doing, not what you tell yourself it is doing. Most people avoid that step because it is uncomfortable, but without it nothing changes. She also pushed back on the idea that people do not have time to fix any of this. That excuse falls apart the second you look at how your day is actually spent. There is time, it is just not being used well. That is not a moral judgment, it is just a fact. What I found interesting is that she did not replace one extreme with another. She still works. She still builds things. The difference is that it is not coming from the same place. Before, work was part of the numbing. Now it is something she chooses with intent. That sounds small, but it changes everything. There is also a broader point here about how people define success. She followed the standard path for decades. The house, the cars, the outward signs that you have made it. When she got there, it did not deliver what it promised. That is not a new story, but it is one that people keep ignoring because the alternative requires more thought and more responsibility. The question she kept coming back to is simple and uncomfortable. What are you using to avoid your own life. Not what are you doing to relax, not what are you doing to unwind, but what are you using to not feel what is actually going on. If you answer that honestly, you start to see the structure you are living in. Most people sense that something is off at some point. They have that moment where they think there has to be more than this. The usual move is to ignore it and keep going. What Anne did was stop and follow that thought instead of pushing it away. There is nothing clean or easy about that process. It is slow and it forces you to deal with things you have been avoiding for years. But the alternative is to stay in a loop that never changes. The takeaway is not some neat system or set of rules. It is more basic than that. Pay attention to what you are doing. Be honest about why you are doing it. Then start making changes, even small ones, based on what you see. Most people never get past the first step. She did, and that is the whole difference. 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

    44 Min.
  2. Keep Going: Building a System That Supports Mothers

    23. MÄRZ

    Keep Going: Building a System That Supports Mothers

    The American healthcare system is full of software. It is not always full of care. That was one of the clearest lessons from my conversation with Melissa Hanna, the co-founder and CEO of Mahmee, a company that provides prenatal and postpartum support through doulas, lactation consultants, nurses, mental health providers, and nutritionists. The services are bundled together and, in many cases, covered by insurance. The support begins during pregnancy and continues through a child’s first year. At first glance, Mahmee sounds like a healthcare startup built around coordination. In one sense it is. But Hanna’s story is really about something harder. She started with the belief, common in startups, that a broken system could be fixed by better software. Over time she found that software mattered, but it was not the thing standing in the way. The original problem that pulled her in was simple and disturbing. The United States has some of the worst maternal and infant health outcomes in the developed world. For Black women, the numbers are far worse. Hanna said Black women face maternal mortality rates three to four times higher than peers with similar clinical and economic profiles who are not Black. Native American and Indigenous women also face sharply elevated risks. These are not small gaps at the margins. They are structural failures. Hanna began by treating the issue as a data and communications problem. Why were patients falling through the cracks. Why were providers not sharing information. Why were systems not talking to one another. Those are reasonable questions, especially in American healthcare, where fragmentation is a defining feature. Patients move between doctors’ offices, hospitals, insurers, specialists, and community providers, often with little continuity between them. So Mahmee’s first life was as a software company. For roughly five years, the company built tools to connect providers and surface information that was not being captured elsewhere. Hanna and her team focused on the providers who often sit outside the formal medical stack, doulas, lactation consultants, nutritionists, nurses, and mental health professionals working in communities, private practices, or local nonprofits. Those providers often knew a great deal about what was happening with a patient. A doula might hear details a patient never shares with an OB-GYN. A lactation consultant might see warning signs that never make it into a medical record. A mental health provider might understand a patient’s risk in ways that do not show up in a standard clinical workflow. But much of that information was effectively invisible to the larger system. Mahmee built software to change that. The company created electronic health record tools, care management systems, communications features, and scheduling and billing software aimed at these community based providers. In doing so, it found real demand. Thousands of providers signed up across 44 states. The footprint was broad. The product was useful. But scale did not follow. That was the hard part. Each provider might only serve dozens, or perhaps a hundred, clients a year. The software worked, but the market around it was too small and too fragmented to produce the kind of reach Hanna believed was necessary. She used an analogy from The Founder, the film about Ray Kroc and McDonald’s. You can have a very good milkshake machine, but if the burger stands are too small to use it at scale, the machine alone does not solve the problem. That was the pivot. Hanna realized the real barrier was not simply that community based maternal health providers lacked software. It was that they lacked a place inside the formal healthcare economy. Insurance often did not cover their services. Payment models were broken. The people who were often best positioned to support mothers before, during, and after birth were sitting outside the system that paid for care. At that point Mahmee stopped being a pure software company. It became a tech-enabled healthcare services provider. Instead of just selling tools to doulas and lactation consultants, the company employed them and built a coordinated care organization around them. The software remained important, but it became infrastructure for a services model rather than the product itself. This is a more interesting kind of startup story because it runs against a habit in tech. Founders often want the clean answer. There is a messy industry, and software will organize it. Hanna found that the mess was deeper than that. The system was fragmented not just technically, but financially and institutionally. Data could not solve a funding problem. A dashboard could not make insurers reimburse the people who were doing essential work. That matters because maternal care is not a niche. Hanna put maternal and infant healthcare in the United States at roughly a $200 billion market. Yet for something that large and consequential, the experience is often poor, costly, and isolating. Many women move through pregnancy and birth without enough support, without clear information, and without much sense of agency over what is happening to them. One of the strongest parts of our conversation came when Hanna described a patient story that made this concrete. The woman was in her early twenties, already had one child, and lived in a rural area with limited hospital and doctor access. During her first pregnancy, she felt judged throughout the process. She was young, a woman of color, and she came away from the experience feeling that she had no control. Labor was difficult. The care felt harsh. She was in pain, asked for help, and felt talked down to rather than supported. When she became pregnant again, she was afraid. She wanted the baby, but did not want to relive the first experience. Through Mahmee, she learned something basic that had been missing the first time. She had choices. She could ask questions. She could slow a conversation down. She could say no. She could ask about pain management options beyond the narrow set that had been presented to her before. She could participate in the process rather than just endure it. That may not sound radical, but in practice it often is. The modern medical system moves quickly, especially in high stress environments like labor and delivery. If a patient is not informed and supported, decisions get made around her rather than with her. Hanna’s point was not that doctors and nurses do not matter. Quite the opposite. In high risk pregnancies, they matter enormously. Her point was that support, education, and continuity of care change the experience and often the outcome. This is also where her critique of the system is most useful. She does not reduce everything to one cause. Systemic racism and bias, she said, are real and they amplify disparities. But she also pointed to two other drivers, fragmentation and the chronic underfunding of preventive care. If support is only available at moments of crisis, then people will continue to arrive at those moments without the preparation, context, and trust they need. Hanna also spoke frankly about the difficulty of funding a company in this area. Building in healthcare is hard. Building in women’s healthcare is harder. Raising venture money for maternal health can mean explaining the problem to investors who have never had to think about it in concrete terms. Part of the job, she said, was reframing the opportunity so people could understand it as both a human problem and a business one. Another part was finding investors for whom the issue already felt personal, because they or someone close to them had been through a birth experience that was worse than it should have been. What stayed with me most was the shape of the lesson. The original thesis was not wrong. Technology does matter. Mahmee still builds software. It still uses connected tools and remote monitoring. It is now looking at how AI might fit into care delivery. But the mature version of the thesis is more grounded. Better care does not come from software alone. It comes from software plus people, software plus payment systems, software plus trust, software plus someone who is actually there when a patient needs help. That is not as neat as a pure software story. It is more true. There is a tendency in startups to assume that every broken institution is waiting for the right app. Sometimes what is actually missing is a workforce, a reimbursement model, and a way to bring overlooked people into the center of the system. Mahmee’s story is about discovering that the missing layer in maternal care was not just information. It was support that had been treated as optional, informal, or outside the reimbursable core of medicine. Hanna’s company now tries to make that support part of the default package rather than a luxury add-on. The goal is not only to improve outcomes, though that is clearly part of it. It is also to change what pregnancy and postpartum care feel like for the person going through it. That may be the real measure here. Not whether a startup found product-market fit in the usual sense, but whether it found a way to make a system less cold, less fragmented, and less likely to fail people at a moment when failure carries enormous cost. — Transcript John Biggs (00:00.161) Welcome back to Keep Going, podcast about success and failure. I’m John Biggs. Today on the show, we Melissa Hanna. She’s the CEO and co-founder of Mahmee M-A-H-M-E-E, which is a fascinating startup. You guys work with doulas and you work with care during birth, right? So why don’t you tell me about that? Welcome. Melissa Hanna (00:30.561) Thanks, yes. Well, Mahmee provides wrap-around prenatal and postpartum support. We do that with a team of doulas, lactation consultants, registered nurses, mental health providers, and nutritionists. And it’s all included in one bundle. that’s actually covered by insurance. In most cases,

    26 Min.
  3. AI Agents, No Hype: A Live OpenClaw Session

    17. MÄRZ

    AI Agents, No Hype: A Live OpenClaw Session

    This is a free preview of a paid episode. To hear more, visit www.keepgoingpod.com Today I ran a short, hands-on session for Keep Going on OpenClaw 101, a plain look at what people mean when they say “AI agents” and how they actually work in practice. An agent is just a chatbot with access. It can reach into your files, your email, your servers, and your tools. In this video I show a live setup. We ran OpenClaw on a Raspberry Pi, connected it to Telegram, and used it to make real changes. It edited a website header, sent emails, created a simple site, and monitored inputs, all from short prompts. I also spent time on the risks. Giving a system this level of access is not trivial. It can write code, trigger actions, and touch production systems. It is useful, but it demands caution. The goal was simple: I wanted to strip away the hype and show what this looks like up close and how it works. As a fan of exploring new tech, I hope you enjoy this quick video and I’ll probably do another one in a few weeks.

    3 Min.
  4. Keep Going: Why Work Dread Is Taking Over Our Lives

    16. MÄRZ

    Keep Going: Why Work Dread Is Taking Over Our Lives

    Work is eating our lives. That much feels obvious. What is less obvious is why we let it happen. I spoke with psychologist and author Guy Winch about his new book Mind Over Grind, which looks at a familiar but poorly understood problem: the slow psychological takeover that happens when work becomes the dominant force in a person’s life. Many of us think we are simply tired or busy. Winch argues that something more corrosive is happening, a kind of sustained dread that alters how we think, how we behave at home, and how we relate to the people around us. The timing is not accidental. The workplace is changing in ways that make people uneasy. The pandemic briefly pushed companies to talk about emotional health and work life balance, but the underlying pressure never really went away. Burnout continued to rise. Now a new layer of uncertainty has appeared in the form of AI, automation, and the constant sense that entire professions may shift under our feet. That uncertainty produces a specific emotional state. Winch calls it dread. It is not simple stress or boredom. It is the heavy anticipation of something bad that may happen but cannot be clearly defined. Psychologists have studied this kind of anticipation in laboratory settings. In one set of experiments people were given a choice between receiving a mild electrical shock later or a stronger one immediately. Many participants chose the stronger shock simply to avoid waiting for the mild one. The anticipation itself was so unpleasant that people preferred to get the pain over with. Work can produce the same effect. When people wake up already dreading the day ahead, the stress does not remain confined to office hours. It bleeds into everything else. A common pattern looks like this. Someone finishes work but cannot mentally leave it behind. They replay conversations with colleagues, worry about tomorrow’s meetings, and anticipate problems that have not yet happened. These thoughts arrive uninvited. They intrude during dinner, while watching television, while trying to fall asleep. The result is hours of unpaid emotional overtime. The damage compounds quickly. Poor sleep makes people more reactive the next day. Emotional withdrawal leads to tension with partners and family members. Hobbies, friendships, and personal interests slowly fall away because the person feels too drained to engage with them. Over time the individual begins to lose parts of themselves that once had nothing to do with work. Winch has seen this pattern repeatedly. He also admits that he has experienced it himself. That admission is important, because the problem is not limited to employees trapped inside rigid corporate structures. It often appears even more strongly among founders, freelancers, and people who run their own businesses. Self employed workers do not have a boss setting limits on how much they can push themselves. If you are ambitious and motivated, there is always more to do. A new client to chase. Another product to ship. Another email to send. The boundary between effort and obsession can disappear without anyone noticing. Technology complicates the picture further. AI systems can now perform many of the small tasks that once filled the workday. Drafting emails, organizing schedules, producing summaries, even generating reports can be handled automatically. In theory this should reduce pressure. In practice it often does the opposite. People rarely use saved time to step away from work. Instead they fill the space with more tasks. At the same time the presence of automation introduces a deeper anxiety. If a machine can handle part of your job today, it may handle the rest tomorrow. Entire professions now operate under that shadow. Even psychologists are not immune. Winch mentioned that some of his clients already consult large language models when he is unavailable. Others bring AI generated advice into therapy sessions and ask whether it matches his recommendations. The implication is obvious. If a machine can simulate the voice of expertise, what happens to the human expert? These questions are still unfolding. Researchers have only begun to examine the psychological consequences of widespread AI interaction. One emerging concern involves emotional attachment to digital agents. Some people now describe their AI assistants as companions or collaborators. Winch views that development cautiously. Emotional attachment to software may signal that other relationships have weakened. When work dominates a person’s attention and energy, connections with family, friends, and communities can erode. In that context it is not surprising that people begin forming attachments in strange places. None of this means that work itself is the enemy. Winch argues that work occupies a central place in human life for understandable reasons. Most people spend more waking hours working than doing anything else. Work provides income, which satisfies basic needs like shelter and food. It also offers social structure, status, identity, and a sense of accomplishment. Much of Maslow’s hierarchy of needs, from security to self esteem, flows through employment. Because of that, threats to work feel existential. Losing a job does not only mean losing income. It can mean losing status, routine, social networks, and a sense of purpose. The unconscious mind interprets those risks as serious dangers, which helps explain why dread becomes such a powerful emotion. The real question is how to prevent work from overwhelming everything else. Winch’s approach is pragmatic rather than philosophical. He focuses on specific behaviors that interrupt the cycle of rumination and anxiety. One of the most common traps involves replaying workplace conflicts or uncertainties long after the workday ends. The brain returns to the same problem repeatedly because it has not identified a resolution. The solution is to convert the worry into a concrete plan. If you are stewing about an argument with a colleague, the task becomes identifying what outcome you want and how you might achieve it. Do you need a conversation to clear the air. Do you need to set boundaries. Do you need to escalate the issue or simply move on. Spending fifteen minutes outlining a response can quiet the brain because the uncertainty has been reduced. In cases where the problem cannot be solved immediately, scheduling time to address it later can have a similar effect. Writing “handle client issue tomorrow at 8:45 a.m.” into a calendar signals to the mind that the concern has not been ignored. The worry is parked for later rather than allowed to circulate endlessly. Another element involves the structure of the workday itself. Many people respond to overwhelming workloads by pushing forward without pause. They move from meeting to meeting, task to task, trying to survive the day. Ironically this behavior reduces productivity. Cognitive performance declines as fatigue accumulates. Creativity, judgment, and executive functioning all deteriorate when the brain remains under continuous strain. Short restorative breaks can interrupt that decline. A few minutes of physical movement, a brief walk outside, or a supportive conversation with a colleague can reset mental resources. What matters is that the break genuinely restores energy rather than adding more stimulation. Doomscrolling through social media or reading the news rarely qualifies. These techniques are modest but practical. They require attention rather than radical lifestyle changes. Most people already spend hours each evening mentally revisiting work problems. Redirecting a fraction of that time toward structured reflection can produce a noticeable difference. The deeper question that emerged during our conversation concerns the future of work itself. If automation eventually provides widespread basic income and eliminates many traditional jobs, what replaces the psychological role of employment? Winch does not pretend to know the answer. Work provides purpose, competition, creativity, and social structure. If those elements disappear, people will almost certainly invent new forms of aspiration to fill the gap. Humans rarely remain idle for long. The shape of those aspirations remains unclear. They might emerge in artistic communities, local organizations, scientific exploration, or forms of competition that do not yet exist. What matters is that the underlying psychological drive toward goals and progress will remain. For now the immediate challenge is simpler. Work has always demanded effort and attention. What has changed is the degree to which it invades the rest of life. Phones keep us connected to the office at all hours. Global competition raises expectations. AI adds uncertainty about what the future holds. The result is a quiet epidemic of dread that many people treat as normal. It is not normal. It is a signal that the balance between effort and recovery has collapsed. Rebuilding that balance does not require abandoning ambition or disengaging from work. It requires noticing how the mind responds to pressure and intervening before the grind becomes the only thing left. 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

    46 Min.
  5. Keep Going: Identity Collapse in the Age of AI

    9. MÄRZ

    Keep Going: Identity Collapse in the Age of AI

    On this week’s episode of Keep Going, I spoke with Patricia Martin, writer, researcher, and author of Will the Future Like You? She has spent a decade studying what happens when failure is not just professional but personal. The kind that makes you wake up and ask, who am I now? Patricia calls it identity-threatening failure. Not every setback qualifies. Missing a target or losing a client stings. But when your business is your baby, when your persona is fused to your public presence, when your work becomes your self, a collapse can feel like rejection at the level of love. The brain codes it that way. Cortisol rises. Adrenaline spikes. Dopamine drops. Executive function weakens. You feel empty, hypervigilant, unmoored. Entrepreneurs are especially vulnerable. We are taught to invest identity in what we build. In the attention economy, we perform ourselves across platforms, post after post, video after video. The persona gets muscular. The inner self gets quiet. Patricia calls the result “persona fog.” We externalize the self so thoroughly that when something breaks, we do not know what remains. What struck me was how physical this all is. This is not motivational poster talk. There is a somatic reaction to identity collapse. A rewiring. Some people pivot sharply. A tech founder goes back to the family farm. A software executive returns to the factory floor. Not because they failed, but because they need ground again. So what do you do if you cannot escape to a dairy farm? Patricia argues there is no hack. There is practice. First, discernment. Identity failure scrambles executive function. You lose clarity. You must relearn how to hear yourself. Second, reflection. We have lost the muscle of self-reflection. There is no app for the inner world. You have to sit with the question: what is this doing to me? Third, confirmation and witness. Own what is happening. Say it out loud. Find someone who can remind you who you were before the fog rolled in. As we talked, the conversation turned to AI, to coders who fear obsolescence, to journalists wondering what work remains. Patricia’s answer was not comfort. It was responsibility. You must know who you are. You must identify what you bring that cannot be replicated. Creativity. Imagination. Sentience. The ability to feel and transmit meaning. Machines can perform. They can flatter. They can automate. They cannot enact being. We are entering what she calls an age of hyper reinvention. Pivots will not be rare events. They will be routine. That means resilience can no longer be grit alone. It has to include an active relationship with the unconscious, with creativity, with reflection. There is a line Patricia shared that I keep returning to. Every defeat of the ego is a victory for the unconscious. In a culture built on dominance and performance, that feels radical. The question is not whether the future will like you. The question is whether you can hear yourself clearly enough to survive it. Transcript Welcome back to Keep Going, a podcast about success and failure. I’m John Biggs. Today we have Patricia Martin. She’s a writer, she’s a podcaster, she’s a researcher, and she’s recently wrote a book. It’s coming out soon, Will the Future Like You? Which I’m afraid to hear the answer for, so welcome, Patricia. Patricia (01:26.852) It’s a pleasure to be here, John. John Biggs (01:28.942) So you’re an old hat at podcasting. You’ve been doing this for quite a while. A million views on your stuff. I want you to welcome to mine. And I’m actually really happy you’re here because this book sounds fascinating. Why don’t you just give us a quick recap about what you wrote. Patricia (01:45.167) So I researched this material in the book for 10 years. And I entered into the research originally to understand the impact of the digital age on the human psyche. And I encountered not only a variety of people and their stories, and then also, you know, as an entrepreneur myself. I underwent a massive change in my life and in my business. And I woke up one morning asking the age old question, who am I? And that is when my research took a fresh direction. And I began focusing on what it means to lose and rebuild identity in the digital age. John Biggs (02:34.144) Mm-hmm. So you were talking earlier about the identity destroying failure. I guess reducing failure, right? A failure so poignant that it changes essentially your entire life. So tell me about that. Patricia (02:49.378) So not every failure that we have affects us at an identity level. What tends to happen though with entrepreneurs, and I would say this is generally a cultural issue for Americans, is that we invest a lot of identity in what we do. Entrepreneurs more so because it’s your baby, it’s your creation. You’re doing something, usually it can be out of a passion or you’re addressing a need in the marketplace. But it is something that you have spotted and you internalize as part of yourself. So what happens when we fail at an identity level, especially in the attention economy, is that we begin to recruit differently from the interior world of ourselves. So let’s say, for instance, you have somebody who has built an online business and they’re an influencer. That is persona heavy identity. And the persona is the weakest part of the psyche. It has never been, it was never designed to undergo the garrulous rigors of online life, right? And yet we’re pounding it day after day, post after post, video after video. And so when something goes awry there, there are some specific things that start to happen. when we tip that into an identity problem. So first of all, it’s a social neural pain. We treat that failure as a rejection, just like we would treat it as a love rejection. And that’s how the brain codes it and the body feels it. The other thing that happens is it’s probably not a surprise that we get a cortisol rush from that kind of failure, but it has a lingering effect. Probably I think the most intriguing thing that came out of the neuroscience is the amount of adrenaline that courses through the body during a failure that is specific to the loss of identity. So it’s as if we are now hyper vigilant to find our sense of self again and we begin the search to recruit back the sense of who we are. Patricia (05:10.536) And so that has an effect that is, you know, and your dopamine goes low. So now you’re operating on cortisol, adrenaline, and low dopamine. So it’s kind of a perfect storm for feeling really empty, lost, stuck, disconnected. So, you know, you’ll talk to people who have had a failure like that. And it requires in the attention economy more than just grit. Because it’s moving so fast, you’re not just, you know, pulling yourself back up by your bootstraps and standing back on your feet. Back on what? What ground? The territory is moving so fast. So this is where you find people tend to tumble out. You’ll also find people at this point sometimes will take a sharp pivot. I talked to people who went from running software companies to working in their father’s box factory. One woman was in a tech startup that got really big. She sold it, and she went back to running the family dairy farm. So it was kind of like they needed an antidote to kind of clear themselves. some of these were success stories. But what was interesting is that some of them didn’t go back to the hurly burly and the grind of something that was as intense. as an online business. John Biggs (06:38.67) So I love that you’re able to codify this and describe it in a very clear way. think a lot of people have that. I mean, first off, a lot of people have that fantasy, right? I think that every single Hallmark movie is about that, where you go back to the small town and you become a dairy farmer after having a hard business, like a hard charging business life. So I think the primary question is, you’re in that mode, once you end up failing out of it, out of an entrepreneurial situation, you described the persona being destroyed to a degree. from a layperson’s point of view, the persona would be just, I don’t know, just my day to day happy-go-lucky whatever. But it sounds like you’re talking about something a lot deeper here. what happens when that identity is destroyed? And how do we get it back, aside from working at a dairy farm? Patricia (07:30.989) Well, here’s the thing. Yeah, because we can’t all do that, right? And some people genuinely like to learn and ladder up. Failure, success, failure, success. I think, though, what’s important to understand about the difference between a more linear type of set of milestones in one’s career and the matrix of what we’re experiencing now. So pivots and turning points happen more frequently. I think we’re going to see with the rise of AI, that is going to become an annual event for people. I’m just putting a pin in that. We’re going to be pivoting more and more and more. And so I think the problem with the internet age is it has made us externalize the self. So, you know, there’s no app for the inner world. We are always out there. We’re always on. We’re always pushing content. And we’re dividing our sense of self across multiple platforms and multiple personas. So when we’re externalized like this, we’re vulnerable. We’re vulnerable to the kind of change. the kind of failure that we’re talking about that have real bodily consequences and psychological consequences. So I would say the plague of our time is something I identify in the book as persona fog. And what happens is that when this gap opens between the true self and the externalized self, we’re no longer in search for the self. We’re performing a self. That’s a very different proposition. The self is at arm’s length to begin with, also making us vulnerable. And so when we take a loss and we’re in this fogged state already, first of

    25 Min.
  6. Keep Going: What to Do When the Bottom Falls Out

    2. MÄRZ

    Keep Going: What to Do When the Bottom Falls Out

    Kevin Gaskell walked into a room expecting to be fired. Instead, he was handed the keys to Porsche UK. That moment says a lot about his career. He is an engineer by training. Then he added an MBA. Then accountancy. Blueprint and balance sheet. He joined Porsche in his twenties, rose through operations, and found himself in a company that was sliding. Three years of unsold inventory. Brutal headlines. Public jokes about pigeons and deposits. He thought he was getting a ten minute exit interview. He stayed for four hours. He told the owners exactly what he thought. What to cut. What to fix. Where to aim. He expected consequences. He got promoted. Five years later, Porsche UK went from last to first. That sounds like a clean arc. It was not. They cut costs by 50 percent. They simplified. They endured press attacks. They carried the weight of three years of unsold cars. That is not glamour. That is grit. Then he did it again at BMW. Then he quit. This is where the story turns. He left one of the best jobs in European automotive to build Cars Direct Europe. Rented office. Desk. Phone. Two young kids at home. American backers. Big plan. Six months in, the investors pulled out. Gone. Now what? No salary. No bank support. No track record as a founder. Just a business plan and three colleagues. This is the part people skip. The terror. The mortgage. The silent nights staring at the ceiling. They negotiated a sliver of funding. Raised money from friends and family. No safety net. Then they pivoted. Consumers were not ready to buy cars online. So they went after fleet operators. Boring. Back office. Massive inefficiency. Two hundred people on phones sourcing cars. They built a platform. They became the backbone. They prepaid dealers with token systems, which quietly funded their growth. Five years later they sold for nine figures. That does not happen because someone is lucky. It happens because when the bottom falls out, you do not flinch. Kevin talks about luck. He was in the right room at Porsche. That is true. But courage matters. When you think you are about to be fired, you can shrink. Or you can speak clearly. He chose clarity. There is another thread running through his story. He does not build fragile companies. He stays five to eight years. He builds teams that can run without him. He does not asset strip. He builds foundations. Today he runs multiple companies in parallel. Fiber networks. Data platforms. Investments. He has rowed oceans. Walked to the poles. Climbed mountains. That part is dramatic, but it is not the point. The point is this: failure comes first. Success is the fight that follows. When the press mocks you. When investors leave. When no bank will return your call. That is the test. Do you believe in the thing? If the answer is yes, you keep going. That is the through line. Not hype. Not trends. Not whatever the market is excited about this week. He is openly skeptical of herd behavior in investing. Dot com. AI. Railways. The pattern repeats. Tools matter. Products matter more. Service matters most. Build something real. Tell the truth about where you stand. Simplify. Cut what does not work. Double down on what does. And when you think you are about to be shown the door, speak up anyway. You might walk out unemployed. Or you might walk out in charge. 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

    22 Min.
  7. Keep Going: Social Capital Is Still Capital

    23. FEB.

    Keep Going: Social Capital Is Still Capital

    I sat down with Constantin Kogan last week after we randomly met in Salt Lake City. We both live near New York. Sometimes the universe has a sense of humor. Konstantin is the founder of Holistic Capital, a multi strategy investment firm focused on digital assets. He also runs a podcast called Holistic Investments. Over 100 episodes. More than 600,000 followers across platforms. Not bad for something he started during COVID while stuck at home. But the interesting part of his story is not crypto. It is not Bitcoin in 2012. It is not Ethereum in 2016. It is not being early to hedge funds or registering with the SEC. It is this: social capital is capital. During COVID he found himself in a tough place. Like most of us. No travel. No meetings. No momentum. He asked a simple question. What can I do that I actually enjoy? His answer was long conversations. Honest conversations. The kind you have in a kitchen at midnight over wine. So he started a podcast. No monetization plan. No big strategy. Just curiosity and discipline. For five years he made nothing from it. Most podcasters quit before episode thirty. He kept going past one hundred. Why? Because he was not optimizing for money. He was optimizing for relationships and learning. That changes everything. We talked about failure. I asked him about bad trades. Crypto winters. Market crashes. He surprised me. The real failures were not financial. They were relational. Picking the wrong partners. He described business like a marriage. You can survive small disagreements. But when a real crisis hits, that is when character shows up. Do you share a vision. Do you share values. When it gets ugly, does your partner protect the mission or protect their ego. You cannot really test that in advance. There is no checklist. No personality quiz that guarantees success. At some point you rely on judgment and instinct. And you accept risk. That is uncomfortable. But it is honest. We also talked about investing. Early in his career he focused on technology and timing. Now he looks at people first. Ideas are abundant. Execution is rare. Motivation varies wildly. Some founders want status. Some want money. Some want to prove themselves. Some want to change the world. Only one of those types will survive when things get hard. If you are building something, remember this. Investors are not just evaluating your deck. They are evaluating your stamina. Your alignment with your team. Your ability to handle conflict without blowing up the room. And if you are thinking about starting a podcast or some other media project, understand what you are signing up for. It is a business. It consumes time. It demands consistency. It does not pay right away. Maybe not for years. But it builds something else. Reputation. Network. Intellectual capital. A record of your thinking. That can compound. Konstantin does not even call himself a VC anymore. He trades liquid markets now. Algorithmic strategies. Volatility. But the podcast still runs. The network still grows. Yesterday he met the co founder of Venmo and invited him on the show on the spot. That is how opportunity works. Quiet compounding. Relationship by relationship. You cannot fake that. You have to show up. You have to publish. You have to keep going when the numbers are small and the monetization is zero. There is a lesson here. Build things that create optionality. Build things that connect you to other capable people. Build things that make you better at thinking and listening. Money follows. Sometimes slowly. Sometimes indirectly. But it follows. In the meantime, protect your partnerships. Choose carefully. Align early. Agree on how you will handle conflict before it arrives. Because markets rise and fall. Technologies shift. Cycles repeat. Character does not. TRANSCRIPT Welcome back to keep going. A podcast about success and failure. I’m John Biggs today on the show. We have Constantin Kogan. He’s the, uh, GP at holistic capital. And you also have a, really cool podcast, which I’m going to be on eventually. So I get to actually, Constantin Kogan (01:18.537) Mmm. John Biggs (01:37.954) meet your audience. But we met just a week ago and you have a really, cool story. So tell us what you’re up to, Constantin. Constantin Kogan (01:47.235) Hi, John. First of all, an honor to be here. Yes, we met in Salt Lake City out of all the places, ironically, live in close by in New York. I don’t know where to begin the story. guess maybe just a little bit of background. I’m originally from Ukraine. was born and raised there, 11 years in the United States. I started my career as a... John Biggs (01:56.236) Yeah. Constantin Kogan (02:12.651) I’m a modernism future trader. Chicago Bota Trader was my first venue where I started to explore financial markets. From there, went through a hole and bought my first 5 Bitcoin in 2012. 2016, I a conscious choice to go all in when Ethereum got out and... thought that programmable money is definitely going to be the future of tokenization of all the assets. 2017, I became a partner in the first crypto fund of hedge funds in the world. We’re the first SEC registered firm. And from there, you know, I had a wild journey co-founding three companies, you know, investing in 80 plus venture startups and running my own. you know, my own hedge fund, working for hedge funds and now focusing on holistic capital, which is basically a multi-asset, multi-strategy investment firm, mostly focused on digital assets, but eventually we will work with different assets on blockchain as well, which I think that’s where the future is going to. And also, as you mentioned, I... also run Holistic Investments, which is the podcast which I started during COVID time. My first guest was Dan Moritz from Pantera Capital because we invested in Pantera so we good relationships with them. Since then, I 100 plus guests on my show and enjoy learning from incredible individuals. John Biggs (03:49.278) And you’ve got you got like 600 plus thousand followers across your across all your platforms. What do you think led to that level of success? And what is what does that give you as a VC? Like I know what this gives me as a I don’t know, just a putz on the internet. But what does that give you as a VC? Constantin Kogan (03:55.957) Yes. Constantin Kogan (04:10.313) Well, to be completely transparent, I don’t consider myself as a VC anymore. Like I used to be. Right now I’m... mostly with trading more liquid assets, right? So you can think about it as algorithmic trading firm, high frequency trading, right? Closer than, so I used to be at VCN. I thought that was incredible opportunity in emerging markets, right? But regardless, what it gives me, it gives me network. I think... Social capital is another form of capital, right? Not necessarily like people who invest in you is your, you know, main business partners in life. You know, some people like stay with you regardless of whether you succeed or you fail. And I think the more value you bring to other individuals, like what look what we’re doing today, right? You’re the first who allowed me to be on your podcast, which I’m very grateful for, and then you’re gonna be on mine, and that’s hopefully gonna inspire others to do the same and share thoughts, you know, learn from each other. I would say intellectual capital and social capital, that’s what’s the primary goal for me, and that’s how I’m giving back to the world by educating the future generations. John Biggs (05:28.396) Mm-hmm. So tell us about the growth of this media empire, I guess you could say. So you started out just deciding to do this. What was the impetus? Why did you want to do it? Constantin Kogan (05:40.105) Well, media empire, it’s a big word. love how you frame it. Future media empire, yes. Yes, I appreciate it. Look, I, again... John Biggs (05:47.03) Yeah, we gotta tuck each other up, yeah. Constantin Kogan (05:54.363) Wholeheartedly, was in a very tough spot during COVID. I think it was a very challenging time for everyone. And I thought to myself, what can I do? I mean, we’re sitting at home. There’s not much to do. you know, everything is digital anyway. You cannot go out. And I started to ask myself, it was more of a soul searching exercise. Like, what can I do to at least do something what I love to, you know, have a cohesive discussion and also somehow impact others to inspire them or to help them in some way and that podcast format was the most relevant for me. I’ve listened to a lot, I’m a big fan of know like Joe Rogan, Alex Hermosy, know and Alex Friedman and many other like greats know people who went bold and started to invite other individuals, have long discussions with them so my My format is about 60 minutes, right? So it’s enough time to learn about a person, about their journey, about where they’re coming from, and also how they achieve this success. And also ask them uncomfortable questions, which allows to bring less controversy, but more about what were the failures? What are the learning lessons? Something that you would not talk on your board meeting or somewhere in the traditional media, right? So more like honest, friendly conversations, you will have when you’re drinking wine with your friend in the kitchen. John Biggs (07:30.606) So tell me about some of those failures. think you, I mean, right now we’re looking at a crypto winter. So that sounds like, it sounds like you might have some issues right now, but tell me about the failures as you move through and try to enter this space. Constantin Kogan (07:44.255) Yeah, as a matter of fact, we’re doing great. maybe we like when you’re trading. the market is a strategy, you’re not like long like any asset like we’re making money even shorting right now. So for us, the volatility and big spikes is where we make most of our money. And that’s the exciting part. Like, and that’s when I finally un

    17 Min.
  8. The Innovators: Why AI Still Needs Humans

    18. FEB.

    The Innovators: Why AI Still Needs Humans

    On this episode of Innovators, I spoke with Jason Ambrose of People.ai about what “agentic AI” actually means, why sales data is messier than most people think, and why blindly trusting large language models is a mistake. People.ai has been around long enough to see multiple waves of enterprise software come and go. Now it’s repositioning itself squarely in the agent era. Most CRM systems tell you what was entered. They don’t tell you what’s actually happening. People.ai takes a different approach. Instead of relying on manual updates, their AI analyzes the communications that define modern sales, emails, Slack messages, meetings, chat transcripts. The system maps that activity to accounts, contacts, and opportunities. That sounds straightforward until you scale it up. If you’re a startup selling to a small business, maybe one salesperson is talking to one buyer about one product. That’s simple. But when Microsoft sells to Verizon, you might have dozens of people on both sides, across legal, technical, procurement, and executive roles. Conversations happen everywhere. Mapping that complexity into a clean CRM record is hard. That’s where People.ai claims it shines. It uses its own AI models, trained on billions of transactions, to reconstruct what’s really going on inside a sales organization. What Is an Agent, Really? We talked about the shift from chatbots to agents. A chatbot answers a question. An agent has an objective. Jason framed it in terms of business process automation. Old-school automation works when the logic is predictable. If this, then that. Stay inside one system, follow a defined workflow. Agents step in when reasoning is required. They cut across systems. They pursue a goal. They have to decide what to do next. But that only works if they’re plugged into real expertise. Jason made a useful distinction. Public LLMs are trained on public data. Enterprise expertise lives in private systems. If you want an agent to act intelligently inside a company, it needs access to proprietary data. That’s a big trust ask. You’re effectively saying, “Let our AI read your emails.” That’s not a small decision. Avoiding “Build Trust With Stakeholders” Anyone who has used a generic LLM for business advice has seen the problem. You ask for guidance and you get vague platitudes. “Build trust.” “Accelerate the deal.” “Engage the customer.” That’s not actionable. Jason argues that this is where expert agents come in. Instead of spitting out generalized advice, they ground recommendations in specific deal data. Who hasn’t responded in three weeks? Which technical blocker hasn’t been addressed? Where did the last conversation stall? Without that grounding, AI defaults to corporate fortune-cookie language. The Capital Markets Reality We also touched on fundraising. SaaS is being repriced. Public markets adjusted first, and private markets followed. Companies that once enjoyed premium multiples are now being reevaluated in light of AI disruption. Capital is flowing into AI-native plays. If you look like “just another SaaS company,” you need a credible AI story. If you genuinely sit at the center of AI transformation, you’re in a stronger position. People.ai is not currently raising, but Jason sees the shift clearly. The market is asking who is being disrupted by AI and who is using it to build something new. Is AI Replacing Jobs? It’s the obvious question. Jason’s take was pragmatic. Technology changes work. It always has. He remembers the early days of the web and the anxiety that came with it. Some jobs disappear. Most jobs change. His line stuck with me: people should work with people, and let AI do the rest. Sales, at its core, is still about relationships. AI can summarize, surface risks, and suggest next steps. It can’t replace trust, empathy, or judgment. At least not yet. If you’re in sales and you haven’t started using AI, Jason’s advice is simple. Start. Use ChatGPT, Claude, Gemini, whatever tool you prefer. Have it rewrite emails. Summarize meeting notes. Draft follow-ups. But don’t copy and paste. He pointed out something many executives are quietly thinking: if you send a clearly AI-generated email without tailoring it, you’re signaling that you didn’t invest the time. And if you didn’t invest the time, why should the recipient? AI can amplify your work. It can’t replace the part that makes you human. People.ai is betting that the future of sales is agentic, cross-system, and grounded in real communications data. Not just dashboards, but reasoning systems that understand what’s actually happening inside complex deals. Whether you buy that vision or not, one thing is clear. The next phase of enterprise AI won’t be about novelty. It will be about integration, trust, and measurable outcomes. And that’s a much harder problem than writing clever emails. TRANSCRIPT Welcome back to the Innovators show about amazing people doing very cool things. I’m John Biggs. Today on the show we have Jason Ambrose from People.ai. It’s agentic and it’s for sales teams, but why don’t you add to that, Jason, welcome. Jason Ambrose (00:24.482) Yeah, thanks, John. So what People.ai does is our AI figures out what’s happening in a sales organization by looking at the communications between your field and your customers. So we analyze emails, chat transcripts, meetings, Slack messages, and the like to turn that beyond just the data to what’s actually happening. How does that how do you find the answers of what’s happening in the organization? And we provide that either to humans or to agents. So that’s been our big shift this year is to realize that the stuff that we were doing for humans in CRM is also very relevant when you have agents trying to figure out what’s happening in sales. John Biggs (01:04.094) So let’s explain agents to folks who might not even understand what’s going on. So the idea originally was that you had a chat bot. You asked it something, and it responded to you. But now we’re talking about agents, which are supposed to be autonomous to a degree. So how do you guys describe those, and how do you use them? Jason Ambrose (01:24.086) Yeah. And hey, look, you know, I may not have everything right on this too, but at least the way that I think about it is maybe starting from a business process automation, right? So, you know, for, for periods of time when we had predictable workflows and we knew, you know, sort of if then else, there’s not thinking that happens there, but we could automate work if that had to happen. John Biggs (01:28.188) Mm-hmm. Yeah. Jason Ambrose (01:48.302) In the case of agents, that now becomes something where they have some chain of thought, they have some reasoning. So they know they have an objective or a purpose that they’re trying to work through. They have to figure out how to get that done. So when there’s a little bit more, you know, thinking, reasoning that needs to happen to figure out how to get that objective, that suits an agent. What I think we’re seeing with customers is they’re figuring out how to unlock that for work that needs to get done across a lot of different systems, right? So, know, BPA, business process automation, or what you have in your workflow tools that tends to say within the silo of a system from data to business roles to presentation layer to humans. When you start to cut across the systems, that’s where there’s been big opportunities for agents. John Biggs (02:37.214) So in this particular case, you guys are focusing on sales leads, that sort of thing. So you basically take every single data point that you have and say, this person, I don’t know, emailed you two weeks ago and also was tweeting this and is interested in this. So why don’t you give him a ring? Is that generally how it works, or what’s the? Jason Ambrose (02:56.376) That’s yeah, that’s really close. Yeah. I think the difference is, you know, let’s think about two different types of selling, right? you could be a startup and you’re selling to a small business. That’s, know, pretty much one buyer. So, you know, if you think about it in the context of CRM, you’ve got one salesperson. You’re selling to one buyer at one account and you’re selling one product that that is pretty simple to figure out, right? Where it gets more complicated is if you’re. Microsoft selling to Verizon just to pick two big companies. You might have 30 or 40 people or more on the Microsoft side. You might have 30 or 40 people on the Verizon side answering different technical questions, having different conversations about different elements of your business relationship and how you match those activities to records in CRM that represent, you know, here’s a person that we’re talking to, here’s the account that we’re talking to. you know, here’s the specific sales opportunity that becomes really hard to do properly. And that’s, that’s where we, that’s where we shine. And that’s where we have, you know, pretty large customers like Red Hat, Verizon as a customer and some others. John Biggs (04:09.712) Would you be able to still do this without AI? Would this exist if we didn’t have this kind of, I don’t know, synthesis, right? Jason Ambrose (04:15.798) It would be really difficult, right? So we have our own AI that’s applied to do the math to figure this out. And it’s learned from looking at billions of transactions over the years, right? The second piece, I think, is how you integrate or interface with other systems. So you mentioned the chat interface. So a human does want to do that, right? So we put this alongside sales opportunity record. If you want to get the full story, you can ask the chat bot, are the risks in these deals or what’s happening in this account? Now with MCP, that same type of interaction can happen from an agent to our system.

    11 Min.
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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, 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/) www.keepgoingpod.com

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  • Erstellt von
    John Biggs
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    2022 - 2026
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