Keep Going

John Biggs

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. Why good is not enough

    -2 дн.

    Why good is not enough

    Keith Wyche has had the kind of career that looks clean from the outside. Bell. IBM. Pitney Bowes. Grocery. Walmart. Board seats. Books. Big jobs. Big teams. The sort of resume that makes people assume there was always a plan and that the climb was smooth. It was not. Wyche told me something on Keep Going that I think a lot of ambitious people need to hear. Early in his career, he was getting results, but he was not getting promoted. He was young, talented, and frustrated. So he gave his boss an ultimatum. Promote me in three months, or I will promote myself. Three months later, he left. Then someone told him the truth. He was a bull in a china shop. He got results, but he abused his people. He fought with finance. He fought with other teams. It was all about him, his team, and winning. That stung. But it also changed him. Wyche realized that he had been copying the leadership models he had seen before him. Hard, military-style management. Beat your chest. Push harder. Win. He was younger than many of the people he led, so he overcompensated. He thought leadership meant force. It did not. That was the beginning of a different kind of career. He worked with an executive coach. He looked at his blind spots. He started to understand where the behavior came from. Maybe it was imposter syndrome. Maybe it was not being heard earlier in life. Maybe it was just immaturity. Whatever the source, he had to face it. That is the part people like to skip. They want the promotion, the title, the corner office, and the authority. They do not want the mirror. Wyche’s new book, Uncommon Leadership: A Blueprint for Restoring Integrity, Trust, and People-Centered Leadership, comes from that same place. He said he wrote it out of disappointment with leadership today. His grandson asked him whether the failures he saw among pastors, politicians, and corporate leaders were what leadership really was. Wyche had to sit with that question. His answer is no. Somewhere along the way, he said, we moved away from servant leadership and toward self-serving leadership. The work became about the leader instead of the people. The quarterly return mattered more than trust. Power mattered more than integrity. Output mattered more than engagement. But two things can be true. You can deliver results and still bring people with you. You can care about the business and care about the people doing the work. Wyche ran roughly 100 Walmart stores with 30,000 people reporting into his organization. If those people did not do their jobs, he could not do his. Leadership was not theoretical. It was operational. That came through clearly in his Walmart story. He joined Walmart in 2015, when Amazon was taking share and Walmart’s grocery business was under pressure. The company was built around stores, and there was real fear that e-commerce would cannibalize the core business. Wyche helped explain the change by telling the story of Sears. Sears had stores and a catalog. It had both the physical footprint and the home delivery model. Then it lost its way. The point was not to scare people. The point was to connect them to the vision. Here is why change matters. Here is how you can help. Here is what happens if we do not move. That is what leaders often miss. They announce the change, but they do not connect people to it. They talk about strategy, but not meaning. They talk about results, but not roles. People do not resist change only because they are stubborn. They resist change because they do not understand where they fit. That lesson matters right now because AI is creating the same kind of fear. People worry about their jobs. They worry about their value. They worry that the thing they trained for will disappear. Wyche does not pretend to know exactly where AI goes, but he has been through enough changes to know that humans are resilient. AI can handle administrative tasks. It can speed up work. It can process information. But it does not replace judgment, empathy, common sense, or the human touch. His line was simple. AI may know a tomato is a fruit, but common sense tells you not to put it in a fruit salad. That is a good leadership test for the next few years. The companies that handle AI well will not just install tools. They will help people understand how to work with those tools. They will help people stay current. They will help people find new ways to add value. Wyche’s advice to his grandson was the same advice he gives to people trying to build a career now. Be a continuous learner. Stay flexible. Do not lock yourself too tightly into one path. Look for ways to add value. Be willing to take the tough assignment nobody else wants. He also made another point that stuck with me. Careers are no longer ladders. They are lattices. You may move up, sideways, or even slightly down to build the experience that gets you where you need to go. The old straight-line career is mostly gone. The people who keep going are the ones who keep learning. That connects to one of Wyche’s earlier books, Good Is Not Enough. Performance matters, but it is not the whole equation. You also need exposure and perception. Are the right people aware of your work? Do they understand the value you bring? What is your brand inside the organization? Nobody breaks through the glass ceiling alone, he said. Someone on the other side has to see you, appreciate your value, and pull you through. That is not cynicism. It is reality. Good work matters. But good work hidden in a corner often stays there. The lesson from Keith Wyche is not that success is about being polished, perfect, or politically smooth. It is about learning. It is about taking correction. It is about understanding that leadership is not something you perform over people. It is something you practice through people. Early in his career, Wyche thought winning was enough. Then he learned that how you win matters. That is the uncommon part. 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

    17 мин.
  2. WorkClaw wants to build an AI team for your team

    1 июл.

    WorkClaw wants to build an AI team for your team

    Everybody has heard the promise by now. AI is going to save time, reduce costs, and help businesses get more done. The problem is that most people still don’t know where to start. That’s the challenge Will Ruben is trying to solve with WorkClaw, a new product from Workmate Labs that turns AI agents into something closer to digital employees. Ruben describes WorkClaw as “an AI team for your team.” Instead of asking users to learn prompt engineering or build complicated workflows, the platform lets them create AI teammates with specific jobs. A florist could train an AI to process invoices. A marketer could create a content assistant. An engineer could build a coding partner. The goal is not to replace workers, but to give every company access to the sort of specialised support that was once available only to large organisations. The idea grew naturally out of Workmate, Ruben’s first product. Workmate focuses on scheduling, one of the most common tasks handled by executive assistants. After building an AI that could manage meetings and calendars, the company began looking at what else an AI teammate might be able to do. Recent advances in large language models made that expansion possible. One of the most interesting parts of our discussion centred on a problem many AI founders rarely talk about. Traditional software is predictable. AI is not. Ask a database the same question twice and you get the same answer. Ask an AI system twice and you might get two different responses. That creates challenges for companies trying to build reliable products. Ruben compares the situation to earlier machine learning systems, including the recommendation engines that power social media platforms. The answer, he argues, is measurement, testing, and designing systems that can recover gracefully when things go wrong. If an AI makes a mistake, users need a way to correct it, and the system needs to learn from that correction. That uncertainty also creates cost concerns. During our conversation I joked about running OpenClaw on a Raspberry Pi and accidentally generating a large OpenAI bill because a poorly configured process kept checking my email. Ruben believes those problems will become less significant as companies gain access to cheaper open source models and more efficient infrastructure. His view is that most business tasks do not require the most advanced models available today. Perhaps the biggest challenge facing AI startups now is not technology but distribution. Building software has become dramatically easier. Getting people to use it remains difficult. Ruben said Workmate Labs relies on a mix of product-led growth, advertising, traditional sales, and good old-fashioned conversations with users. One tactic that has worked particularly well is identifying companies that visit the website, understanding who they are, and following up before interest disappears. Looking ahead, Ruben says WorkClaw’s next step is reducing the friction involved in getting started. While the current product removes much of the technical complexity, users still have to decide what kind of AI teammates they want and how those teammates should behave. Future versions will offer ready-made AI roles, including executive assistants, marketers, engineers, salespeople, and operations staff, making it easier for businesses to start seeing value immediately. The broader question is whether people want another tool or whether they want something that feels more like a co-worker. Ruben is betting on the second option. If he’s right, the future of software may not be a collection of apps sitting on a desktop. It may be a collection of digital colleagues working quietly in the background, each trained to do a specific job and each getting a little better over time. That future is still taking shape. But products like WorkClaw suggest it may arrive sooner than many people expect. 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 мин.
  3. How Lium turns physical-world data into answers

    24 июн.

    How Lium turns physical-world data into answers

    Josh Knutson and Ryan Thill are building Lium for a problem that sits just outside the usual AI demo. Most AI tools are very good at text, code, and spreadsheets. Lium is focused on the messier stuff, the huge physical-world data sets that sit inside farms, climate labs, energy systems, logistics networks, and other operations where the answers are buried under terabytes of data. Knutson, the CEO and co-founder, describes Lium as an “agent harness” or a cloud operating system for agents. The idea is to give language models the tools they need to work over large, complex data sets that they cannot handle well out of the box. Instead of asking a data scientist to build a pipeline every time someone has a question, Lium lets subject matter experts ask questions in natural language and then builds the tools and workflows needed to answer them. Thill, co-founder and president, said the core user is often not a software engineer. It is the person who knows the domain, knows the data matters, and knows there are answers inside it, but cannot easily get them out. He gave the example of a farm operator working with soil reports, NOAA data, tractor data, and crop performance information. The operator may know something is off, but does not have the time or technical skill to combine all those sources into a useful answer. That is where Lium is meant to fit. A user can describe what they want to know, and the system builds repeatable workflows around the data. Once those workflows exist, other people inside the organization can use them too. An analyst can build the tool, and a CEO can later ask a simple question that relies on the analyst’s work in the background. That shared layer is one of the more interesting parts of the product. Knutson described work with the North Carolina Institute for Climate Studies, where scientists and researchers built tools inside Lium, then on-screen meteorologists could ask questions and get answers using the right climate data without needing to understand every data source underneath. The company’s bet is not that AI replaces the expert. It is that AI needs the expert. Knutson said Lium is built around human-in-the-loop workflows because language models do not have enough training data to understand all the hidden patterns and details inside many physical-world data sets. The system has to know when to stop, ask the human for domain knowledge, and then turn that knowledge into a tool the system can use again. That point matters because the obvious fear is job loss. If a person’s job is to build reports, what happens when anyone can ask Lium for the same report? Knutson and Thill argue that the expert becomes more valuable, not less, because the tool captures and scales their knowledge. Thill compared it to software engineers using AI coding tools. The tools make people more productive, and that can create demand for more work that was not worth doing before. Lium is still early, but the founders say they are seeing strong interest. During private beta, around 50 groups worked in the platform. Now that it is public, the challenge is different. Instead of onboarding users by hand, the company has to explain the product clearly enough that people can find it, understand it, and get value without a sales call. That is not easy, because Knutson and Thill say many potential users do not know this kind of system is possible. For Lium, the main competitor is not another startup. It is the belief that this kind of data is too hard to work with. Fundraising followed a similar path. Knutson said early investors were skeptical because he and Thill did not have the usual Silicon Valley AI profile. They had startup experience, but not the standard AI pedigree. The company raised a smaller pre-seed round than it wanted, then came back after showing it could build things people did not think it could build. That proof changed the conversation. The company spent roughly 18 months learning and building before going public. Knutson said this was not the kind of product where you can ship a tiny version and see what happens. If someone brings a terabyte of data, the system has to work. That meant building alongside design partners until the product was strong enough to handle real use. Now the work is public. Lium is learning from users, tightening the funnel, and building around what people actually do with the product. The name, by the way, comes from language plus the suffix of physical elements, a nod to the company’s goal of connecting language to the physical world. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.keepgoingpod.com/subscribe

    20 мин.
  4. 22 июн.

    The janitor, the professor, and the meaning of success

    Most of us spend a lot of time thinking about what we want. A better job. More money. A nicer house. More freedom. Less stress. Very few of us spend much time thinking about what a successful life actually looks like. That question came up during a conversation with Perry Atwal, a lecturer at the University of British Columbia and author of the upcoming book Wisdom for Life. After teaching more than 20,000 students around the world, Atwal has spent years looking for patterns in the people who thrive and the people who struggle. One of the most interesting things he said was that most of us are aiming too low. He asked a simple question: when you have no reason to feel anything, where is your energy level? On a scale from one to ten, are you ready to go back to bed, or are you bouncing off the walls? Most people, he said, live around a five or six. His argument is that we should be trying to live closer to a nine or ten. That idea stuck with me. A lot of us assume that energy comes from success. Atwal sees it the other way around. Energy creates success. The people who excel are often the people who bring more than what is asked of them. If an assignment calls for three things, they deliver five. They are curious. They stay engaged. They keep moving. His prescription is surprisingly simple. Take care of your health. Walk more. Spend time outside. Do work you genuinely enjoy. “I walk for two or three hours every day,” he told me. “Virtually every great thought I’ve had in the last twenty years has been on that walk.” That sounds almost too simple in a world obsessed with optimisation, AI, and productivity hacks. But perhaps that is the point. The most powerful part of our conversation came when we started talking about work and purpose. Many people feel trapped. They sit in offices wondering whether this is all there is. They worry they picked the wrong career. They worry they missed their chance. Atwal argues that the pressure to find the perfect path is largely self-imposed. Previous generations might have held two or three jobs during a lifetime. Today’s workers may have ten or twelve jobs and move across multiple industries. The first job does not have to be the perfect job. It only has to be the next step. He also believes we underestimate the power of perspective. One example from the interview has stayed with me. He talked about cleaners. Some people might look at a cleaning job and see failure. The happiest cleaners he knows see something completely different. They see buildings that people want to enter because of the work they do. They see value created. They see contribution. The job is the same. The story they tell themselves is different. That idea feels especially important right now. We live in a moment where every headline seems designed to convince us that the future is bleak. Economic uncertainty. Political conflict. AI replacing jobs. Constant disruption. Atwal’s response is not to ignore reality. It is to choose where to focus your attention. “The only constant really is change,” he said. That may be the closest thing to a universal truth. The people who flourish are rarely the people who predict the future correctly. They are the people who adapt. They keep learning. They develop skills that transfer from one job to another. They stay curious. They also let go. Let go of old habits. Let go of old assumptions. Let go of the idea that your life must follow a script. Atwal even applies that philosophy to his closet. If he hasn’t worn something in two years, it’s gone. The same rule probably applies to a lot more than clothes. If there was one lesson I took from our conversation, it was this: Success is not a destination. It is a way of moving through the world. Take care of your health. Do work that matters to you. Surround yourself with positive people. Focus on your strengths. Help others when you can. The details of your career will change. The technology will change. The world will change. The question is whether you will 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

    28 мин.
  5. WorkClaw wants to build an AI team for your team

    17 июн.

    WorkClaw wants to build an AI team for your team

    Everybody has heard the promise by now. AI is going to save time, reduce costs, and help businesses get more done. The problem is that most people still don’t know where to start. That’s the challenge Will Ruben is trying to solve with WorkClaw, a new product from Workmate Labs that turns AI agents into something closer to digital employees. Ruben describes WorkClaw as “an AI team for your team.” Instead of asking users to learn prompt engineering or build complicated workflows, the platform lets them create AI teammates with specific jobs. A florist could train an AI to process invoices. A marketer could create a content assistant. An engineer could build a coding partner. The goal is not to replace workers, but to give every company access to the sort of specialised support that was once available only to large organisations. The idea grew naturally out of Workmate, Ruben’s first product. Workmate focuses on scheduling, one of the most common tasks handled by executive assistants. After building an AI that could manage meetings and calendars, the company began looking at what else an AI teammate might be able to do. Recent advances in large language models made that expansion possible. One of the most interesting parts of our discussion centred on a problem many AI founders rarely talk about. Traditional software is predictable. AI is not. Ask a database the same question twice and you get the same answer. Ask an AI system twice and you might get two different responses. That creates challenges for companies trying to build reliable products. Ruben compares the situation to earlier machine learning systems, including the recommendation engines that power social media platforms. The answer, he argues, is measurement, testing, and designing systems that can recover gracefully when things go wrong. If an AI makes a mistake, users need a way to correct it, and the system needs to learn from that correction. That uncertainty also creates cost concerns. During our conversation I joked about running OpenClaw on a Raspberry Pi and accidentally generating a large OpenAI bill because a poorly configured process kept checking my email. Ruben believes those problems will become less significant as companies gain access to cheaper open source models and more efficient infrastructure. His view is that most business tasks do not require the most advanced models available today. Perhaps the biggest challenge facing AI startups now is not technology but distribution. Building software has become dramatically easier. Getting people to use it remains difficult. Ruben said Workmate Labs relies on a mix of product-led growth, advertising, traditional sales, and good old-fashioned conversations with users. One tactic that has worked particularly well is identifying companies that visit the website, understanding who they are, and following up before interest disappears. Looking ahead, Ruben says WorkClaw’s next step is reducing the friction involved in getting started. While the current product removes much of the technical complexity, users still have to decide what kind of AI teammates they want and how those teammates should behave. Future versions will offer ready-made AI roles, including executive assistants, marketers, engineers, salespeople, and operations staff, making it easier for businesses to start seeing value immediately. The broader question is whether people want another tool or whether they want something that feels more like a co-worker. Ruben is betting on the second option. If he’s right, the future of software may not be a collection of apps sitting on a desktop. It may be a collection of digital colleagues working quietly in the background, each trained to do a specific job and each getting a little better over time. That future is still taking shape. But products like WorkClaw suggest it may arrive sooner than many people expect. 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 мин.
  6. How to move from the corporate world into a startup

    10 июн.

    How to move from the corporate world into a startup

    Andrew Reid has seen the supplements business from both sides, as a founder and as an operator inside a very large company, and he thinks the next step is personalisation that does not feel like homework. Reid is the CEO of Claer AI. The product is an AI-driven supplement regimen builder that asks for your health profile, matches it against a large library of peer-reviewed studies, then turns the recommendations into a practical plan, starting with sachets you can mix, and aiming later at a single personalised powder. He describes it as using AI like a nutritionist, then following that logic through a supply chain he already knows well. His origin story is straightforward. Reid says he built and sold a social media analytics company to Comscore, then later ended up running one of the world’s largest supplement companies as part of a small executive team. That role changed his view of supplements, not as gym culture products, but as widely applicable compounds with strong safety profiles and real evidence behind them. He uses his own experience as the hook, after adding basic products like protein and creatine, he says he saw a clear change in strength and mobility as he aged. The gap he wants to fix is trust and confusion. Reid calls the industry large but fragmented, and he points to consumer confusion as a driver. His claim is that people do not stick with one brand because the space feels like a Wild West, and they worry about doing something wrong or wasting money. Claer’s AI is meant to create a long-term relationship that adapts over time, including using biometrics from wearables and adjusting the regimen so users do not have to think about it constantly. The most concrete feature he described is interaction checking. A common fear is that a supplement will clash with a medication or another intervention. Reid says Claer uses a “currently updated” evidence base to flag these issues, and he thinks that capability has applications beyond supplements, especially anywhere medication regimens shift often. On funding, Reid says the company started self-funded, went through the ERA accelerator in New York, and that the health tech environment is active enough that fundraising is not the core problem. He frames the business model as bundles with solid margins and higher cart values, plus better retention because of the personalised front end. He also splits the company into two stages, first prove the commerce and retention dynamics, then raise larger funding later to personalise the manufacturing itself and deliver the single powder vision. Reid also made a broader point that fits the Innovators beat. He argues that AI lowers the cost of running an “antiquated” industry by replacing a stack of specialised SaaS tools across the whole value chain. He says that in his prior role he spent millions per year on specialised software, and he expects a large share of those tools to become unnecessary as teams build from basic AI primitives and open source components. 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 мин.
  7. Creative people adapt

    8 июн.

    Creative people adapt

    Angelo Sotira built DeviantArt at nineteen, and then spent the next two decades watching the internet grow up, get rich, and get mean. When he joined me on Keep Going, he was not doing the victory lap thing. He was trying to name what changed, and what it means for anyone trying to build something creative right now. He described the early internet as directed. People knew what was missing. They wanted communities, comments, and places to post work, and they built them from scratch because the infrastructure did not exist yet. Now, he says, you can recreate 95 percent of those platforms in a weekend. The hard part is not building the tool, it is making it matter. That is where his argument gets uncomfortable. Virality used to ride on something raw and human, and he thinks AI breaks the default assumption that what you are seeing is real. His view is that we are moving into a world where you should assume media is inauthentic until it is proven otherwise. That shift changes what spreads, what people trust, and how creators feel about putting work into the world. Layer is his response. It is a hardware company, a digital art display built to treat generative and kinetic art like fine art, not like a TV on a wall. He told me the idea grew out of an identity crash after leaving DeviantArt, and a simple desire, he wanted the best digital art on his own wall, presented correctly. He went looking for a product that did it, and he says he could not find one, so he built it. He also does not sugarcoat how hard hardware is. He told me getting a manufacturing partner is harder than raising venture capital, because the manufacturers that can actually deliver are not built for startups, and you have to earn your way into their calendar. That challenge is part of what pulled him back into building in the first place. He missed meeting people, the artists, the founders, the operators in labs, the whole human mess that comes with making something real. The Keep Going part of this episode is not “follow your passion.” It is more specific. Angelo is making a bet that digital art is going mainstream, and that the people who will survive this AI wave are the ones who adapt their craft to what the medium is good at. He said still images should often be printed, because printing is already excellent. Displays should be used for work that moves, especially generative work that does not loop in a way your brain gets tired of. He thinks that kind of work will define the century. He is not naïve about the cost. He said illustrators are suffering and that many jobs are gone, and he widened it to the broader creative class, designers and builders getting hit by tools that shrink teams overnight. Still, he ended with the only kind of optimism that counts, the practical kind. Creative people adapt. They always have. 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

    33 мин.
  8. The Innovators: This app makes music therapy accessible to everyone

    3 июн.

    The Innovators: This app makes music therapy accessible to everyone

    Most people think of music as entertainment. Rachel Francine thinks of it as infrastructure for the brain. On this episode of Innovators, I spoke with the SingFit co-founder and CEO about how her company is using therapeutic music to help people with dementia, traumatic brain injuries, and speech loss. The idea sounds almost deceptively simple. People who lose the ability to speak can often still sing. Music activates multiple regions of the brain at the same time, creating pathways that normal speech sometimes cannot access. SingFit turns that principle into software. The platform recreates part of what music therapists do in clinical settings. Songs include lyric prompts, guided vocal tracks, and structured timing designed to encourage participation and cognitive engagement. The result is something that can be used not just by trained therapists, but by caregivers, nursing assistants, and families at home. Francine said the company now operates in more than 10,000 skilled nursing and senior living centers across the United States. The company recently launched a caregiver-focused version with AARP aimed at helping families support loved ones at home. One of the more interesting parts of the conversation was how deeply personal the company’s origin story is. The original idea came from Francine’s father, an inventor and former opera student who was fascinated by the role of lyric prompters in live performance. He imagined a system that could feed people lyrics in real time long before the technology existed to build it. Years later, Francine’s brother became a music therapist after seeing a friend recover from a traumatic brain injury and emerge from a coma mouthing the words to “Wish You Were Here.” That combination of therapy, family history, and technology became the foundation for SingFit. Francine also made an important point about startups in healthcare and assistive technology. Too many founders start with technology instead of problems. Her advice was direct. Find a real problem first, then build the system around solving it. In SingFit’s case, the company focused on one issue inside dementia care: social isolation. Patients often begin withdrawing socially as their condition progresses, which can accelerate decline and increase care costs. The platform was designed to create engagement, connection, and routine through music. The broader issue she kept returning to was aging. Dementia care, caregiver support, and cognitive decline remain massively underserved compared to other parts of healthcare. Francine pointed out that only a handful of dementia drugs have been approved over the past century while cancer treatments continue advancing rapidly. Music may not solve dementia. But the company is betting that engagement, memory, rhythm, and emotional connection can improve quality of life in ways that medicine alone often cannot. And honestly, there is something refreshing about hearing a founder talk about care instead of scale for once. 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

    14 мин.

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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