Keep Going

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 resu...

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.”...

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...

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...

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.”...

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...

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 w...

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...

Melissa Banks spent 17 years in an abusive marriage before she rebuilt her life from scratch. No money. No plan. Two sons depending on her. What came next became a lesson in something most people miss when they talk about success. Success is rarely a clean break. It is usually a slow crawl out of fear. On this week’s episode of Keep Going, Melissa talks about leaving abuse, learning how to speak u...

Daniel Burrus has spent decades talking about the future, but the most useful thing he said on Keep Going had nothing to do with AI or technology. It had to do with regret. Before he built six companies, before the bestselling books and the keynote stages, he was teaching biology and physics. He had an idea for an airplane design and wanted to turn it into a business. The problem was simple. He ha...

Paulius Judickas spends a lot of time thinking about something most people never notice, IP addresses. The internet runs on them, every server, every phone, every AI endpoint, every connected device. But there are only so many IPv4 addresses left, and the strange economics around that scarcity have created a new kind of market. On this episode of Innovators, I spoke with Judickas, VP of Strategic...

Stephen Gillen told me something during this week’s Keep Going that stuck in my head long after we finished recording. “No one’s going to come save you,” he said. “And neither should they.” It sounds harsh at first. But the more he talked, the more it made sense. Gillen’s life did not begin in anything close to stability. He described being abandoned as a child in Ireland during the violence of th...

AI systems are getting better at answering questions, but they still forget almost everything that happens outside the screen. Elisa Lu thinks that’s the missing piece. Lu is the co-founder and COO of Memoket , a startup building what she describes as a “context layer” between the physical world and AI. The company’s product combines a wearable recording device with software that tracks conversati...

Daniel Burrus has spent decades talking about the future, but the most useful thing he said on Keep Going had nothing to do with AI or technology. It had to do with regret. Before he built six companies, before the bestselling books and the keynote stages, he was teaching biology and physics. He had an idea for an airplane design and wanted to turn it into a business. The problem was simple. He ha...

Arthur Chen is trying to do something boring on purpose. Chen is the co founder and CEO of Verdi Agriculture , and he describes the company as “physical AI for farm infrastructure,” starting with irrigation. The pitch is not about tractors or drones. It is about the pipes, valves, pumps, and filter stations that farms rely on every day, and that most farms still run by hand. Chen says about 95 per...

You keep hearing that success is about vision. That is not wrong, but it misses the harder truth. Vision is easy. Living with the consequences of your decisions is the work. I spoke with Jae Lee , a founder on his eighth startup, and what stayed with me was not the wins. It was the pattern. He did not begin with some grand plan. He saw problems that were right in front of him. A school without a w...

Stefan Lindstrom has spent years studying entrepreneurs. Not the mythology but the actual behavior. He’s givens of thousands of tests and had thousands of conversations. And what he came back with is not inspiring. It’s repetitive. Same people succeed over and over. Same people stall over and over. He sees the same habits. The same reactions. The same blind spots. But who succeeds and who fails? L...

David Silverstein started building Amaze Health in 2019, before the current AI wave made “AI health” feel like its own category. He told me he was not trying to invent the models, he was trying to build the platform that would be ready when the models were ready. Silverstein, CEO, describes the company as an operating system for healthcare, something employers and patients can use to manage care t...

I sat down with comedian DC Pearson and what struck me wasn’t the success. It was the patchwork. From the outside, it looks clean. Comedy group, Sundance film, books, writing for TV. A straight line. But it isn’t. “Our life is composed of days,” he told me. “And this is one of them.” That’s the job. Not the career. The day. Because most of the time, it’s not the dream. It’s the gap between dreams....

I talked to Ela Thier this week on Keep Going, and she said something early on that told me exactly where the conversation was headed. Filmmakers, she said, know a lot about failure. That sounded like a joke, but not really. It was more like a basic fact of the trade. Thier is a writer, director, and the founding director of the Independent Film School , which now has something like 65,000 members...

I ran into a strange hack this week. It looks simple at first, but it is not. It targets job seekers. I think I recall submitting a resume for a job at a company called Runeapes, which, at least on the surface, looks like a real website. You get a message saying you missed an appointment. It points you to a booking page. The name looks normal, the flow looks normal. You click through, pick a time,...

I talked to Bobby Mascia this week on Keep Going, and what struck me was how different his story is from the usual startup script. A lot of founders like to talk about building from nothing, but Bobby’s problem was almost the reverse. He had something waiting for him, a family business, a clear role, a life that had already been sketched out by other people, and he still had to figure out whether...

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...

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, co...

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. W...