Most Entrepreneurs Should Quit — Nathan Kaiser

Why Bad Leadership Works — Daniella Young

Daniella Young has built a brand by saying the thing most people avoid: bad leaders, bad groups, cult dynamics, and toxic loyalty are not fringe problems. They show up in politics, companies, the military, families, social media, and anywhere people stop questioning the room they are in. Jason and Daniella talk about turning trauma into work, why "followers" should not become worshippers, how she built a creator-led book business, why she focuses on bad leadership instead of good leadership, and what most people misunderstand about cults, scams, fame, politics, parenting, and platform building. We also discuss: • Talking to Khloe Kardashian and handling criticism for using big platforms • Why confidence can make people more vulnerable to scams and cults • The economics of traditional publishing vs self-publishing • Building a personal brand around your actual story • Why "front of the room advantage" changes how people see you • Veterans, identity, and the danger zone after leaving the military • Social media trolls, monetization, and standing out on purpose • Parenting after trauma • Politics, corruption, term limits, and leadership failure • Why there are no rules for creators right now Daniella's links Instagram: https://www.instagram.com/daniellamyoung_/ [https://www.instagram.com/daniellamyoung_/] TikTok: https://www.tiktok.com/@knittingcultladycaptain [https://www.tiktok.com/@knittingcultladycaptain] YouTube: https://www.youtube.com/@KnittingCultLady [https://www.youtube.com/@KnittingCultLady] Website: https://knittingcultlady.com/ [https://knittingcultlady.com/] Jason links https://linktr.ee/cavnesshr

Why AI Sales Should Make Selling More Human with Swetha Puvvada

AI sales is often framed as replacement. Swetha Puvvada sees it differently: the real opportunity is using AI to remove the busy work so sellers can get back to listening, understanding pain, and having better conversations. Swetha is Head of Product & Growth at Teameight, an AI SaaS company building an augmentation platform for sales teams. We talk about product, GTM, customer feedback, career growth, mountaineering, and how she went from early-career intern to owning product and go-to-market inside a startup. We also discuss: • Why AI should augment sales instead of replacing sellers • How Teameight helps ramp new sellers faster • Why negative customer feedback is useful when it is specific • What makes someone a good salesperson • How Swetha moved from internship to Head of Product and GTM • Why younger talent needs broader product and systems thinking • How mountaineering teaches trust, risk, and preparation • Being one of the few women in tech and mountaineering • Why taking opportunities matters more than waiting for permission Swetha links LinkedIn: https://www.linkedin.com/in/swetha-puvvada/ [https://www.linkedin.com/in/swetha-puvvada/] Teameight: https://www.teameight.ai/ [https://www.teameight.ai/] Jason links https://linktr.ee/admin

The Roti Robot Problem with Komal Kashiramka

Fresh roti is simple to eat and hard to automate. Komal Kashiramka is building Poshan, a robotics company developing next-generation kitchen appliances, starting with an automatic roti maker designed to create soft roti that lasts for hours. Komal shares how she moved from Microsoft and Meta into entrepreneurship. Why hardware requires a different level of patience than software and what founders can learn from customer discovery, AI, parenting, and building something people will trust in their kitchens. We also discuss: • Why soft roti is the real product challenge • Building a hardware company in the R&D phase • What AI changes for junior engineers • Why fundamentals still matter in software • Leaving corporate life without having everything figured out • Startup 425 and Seattle Public Library business resources • Raising kids while building a company • RotiTales and making roti easier to understand Komal links Poshan Website: https://poshan.us/ [https://poshan.us/] Poshan LinkedIn: https://linkedin.com/company/poshan-inc [https://linkedin.com/company/poshan-inc] RotiTales Website: https://rotitales.com/ [https://rotitales.com/] RotiTales Instagram: https://instagram.com/rotitales [https://instagram.com/rotitales] RotiTales LinkedIn: https://www.linkedin.com/showcase/rotitales/ RotiTales Facebook: https://www.facebook.com/rotitales [https://www.facebook.com/rotitales] RotiTales YouTube: https://www.youtube.com/@rotitales [https://www.youtube.com/@rotitales] Jason links Jason's Linktree: https://linktr.ee/admin [https://linktr.ee/admin] Jason's LinkedIn: https://www.linkedin.com/in/jasoncavness/ [https://www.linkedin.com/in/jasoncavness/] YouTube Channel: https://www.youtube.com/channel/UCGsw6kzZE40sSUZgoStVaJw?sub_confirmation=1 [https://www.youtube.com/channel/UCGsw6kzZE40sSUZgoStVaJw?sub_confirmation=1]

How Grief Becomes Art with Eden Marryshow

Most people run from grief. Eden Marryshow turned it into a film. In this conversation, Eden breaks down the emotional process behind filmmaking, storytelling, creativity, and why the best art usually comes from the most personal places. We talk about losing family, directing actors, independent filmmaking, community, and the long path creators take back to who they were before the world told them to stop creating. This episode is also a masterclass on storytelling itself from Star Wars and Scorsese to creative discipline, ego, collaboration, and why limitations often produce better art than unlimited budgets. We also discuss: • Why most people know who they are by age six • The connection between grief and creativity • Directing actors without ego • Why independent creators have to learn everything • The psychology behind great storytelling • Rocky, Star Wars, Goodfellas, and favorite films • Why "story is king" in filmmaking • How schools often suppress creativity • Building community through storytelling • NFL talk, Giants football, and leadership Guest links Instagram: @edenmarryshow Email: 511eden@gmail.com [511eden@gmail.com] Jason Linktree https://linktr.ee/admin [https://linktr.ee/admin]

Most Entrepreneurs Should Quit — Nathan Kaiser

Entrepreneurship isn't freedom it's volatility, pressure, and constant uncertainty. Nathan Kaiser built 2bar Spirits by embracing that reality, not ignoring it. He breaks down why most people shouldn't start companies, what actually keeps a business alive, and how constraints, not capital, create better outcomes. This is a raw look at building something real in a crowded, unforgiving industry. We also discuss: • Why starting a company is usually the wrong financial move • How constraint beats capital in building a business • The myth of overnight success (and the Tito's example) • Why focus wins over product expansion • The real role of rejection in sales and growth • How long-term thinking applies to both whiskey and life Nathan Kaiser LinkedIn: https://www.linkedin.com/in/nckaiser/ [https://www.linkedin.com/in/nckaiser/] 2bar Spirits: http://2barspirits.com [http://2barspirits.com] Email: info@2barspirits.com [info@2barspirits.com] Jason links LinkedIn: https://www.linkedin.com/in/jasoncavness [https://www.linkedin.com/in/jasoncavness] Instagram: https://www.instagram.com/thejasoncavnessexperience/ [https://www.instagram.com/thejasoncavnessexperience/] TikTok: https://www.tiktok.com/@jasoncavness [https://www.tiktok.com/@jasoncavness] Podcast: https://www.thejasoncavnessexperience.com [https://www.thejasoncavnessexperience.com] Website: www.cavness.io [https://www.cavness.io]