Boss Mode Podcast

Heaven is supposed to be the answer. So why does every fictional version of it — Dune's banned computers, the Culture series' bored citizens, Ready Player One's gluttony chair — read as a warning? In this episode, David Lee and Dee Deng wrestle with the limitation problem: if struggle creates diamonds, what happens when the pressure is removed? David argues that omniscient, all-powerfu...

What does it actually take to thrive in a world where Microsoft can wipe out a $5B legal AI company with a single Word feature, where Uber drivers are unknowingly training the robots replacing them, and where the gap between "IC" and "manager" is no longer a career step but a survival skill? In this episode, David Lee and Dee Deng dig into the management skill that's quietl...

Anthropic is dropping bombs every week. Claude Design, Claude Routines, Claude Code, and a 20x Max plan that lets a single human run circles around teams of ten. Meanwhile only 26% of Americans say they're favorable toward AI, a 20-year-old just threw a Molotov cocktail at Sam Altman's house, and Australia banned social media for under-16s. Something is breaking, and something is being bui...

AI, Math, and the Edge of Learning Min Lee is CEO of Prep Anywhere, an elite math prep academy. A year ago, he was spending half a million dollars on developers and drowning in legacy code. Today, he's rebuilt the entire app from scratch using Claude Code — not a single line of the old code remains. David & Min get deep into what vibe coding actually looks like when you're building a r...

From Searchable to Transactable Jimmy Gibson has spent 20 years helping businesses grow through digital marketing as the leader of Thrive Agency. In this episode, David and Jimmy explore what happens when AI doesn't just change how people search — it changes whether people search at all. The conversation starts with the current state of SEO: 60% of searches now end in zero clicks, LLM referral...

David met Ari Lowinsky in a hot tub at Lifetime Fitness in Boston. What followed was one of the rawest conversations on the show yet — about what it means to be human in the age of AI, why most people are sleepwalking through life as NPCs, and whether technology is making us more creative or killing creativity entirely. Ari pushes back hard. He argues that humans are more creative than AI will eve...

Marketing is Dead. Long Live Marketing. Kate Assaraf is the founder and CEO of DIP Sustainable Hair Care — a brand built entirely through word of mouth, local retail, and real human connection. No Meta ads, no TikTok campaigns, no paid media. In four years, DIP has redirected over $5 million back into local economies and proven that counterculture commerce works. David and Kate explore why the mos...

To Tax or Not to Tax AI Andrew Yang says tax the bots. David and Dee say not so fast. In this episode, we break down Yang's proposal to shift taxation from labor to AI — why the idea exists, why it sounds reasonable on the surface, and why it could actually widen inequality and cripple American competitiveness at the worst possible time. The conversation moves from tax policy into a broader lo...

China's OpenClaw adoption is exploding—mass install events, cloud server gold rushes, and the "lobster farming" phenomenon drawing comparisons to the DeepSeek and ChatGPT shocks. Meanwhile, NVIDIA's Jensen Huang calls OpenClaw "the single most influential software ever built" and announces NemoClaw, an enterprise-grade secure version. David and Dee break down what this...

The Unstoppable Poet | Boss Mode Podcast Ep. 24 She went to Home Depot with $20, built a table, sat on a street corner in Brooklyn, and wrote poems for strangers. No platform. No followers. No money. Today Shana Roark — aka Supergirl Reject — has 75,000 Instagram followers and a full-time career doing exactly what she loves. In this episode, David sits down with Shana to talk about poetry on deman...

You're Fired! | Boss Mode Podcast Ep. 23 Jack Dorsey just cut 4,000 jobs at Block and cited AI tools as the reason. The stock surged 24%. This is not a warning sign — it's already happening. In this episode, David & Dee break down what the Block layoffs really mean, why Airbnb is quietly replacing customer support with agents, and why the "AI won't take jobs" crowd is only right about the past...

OpenClaw: Hype or Not? | Boss Mode Podcast Ep. 22 Dee finally got his hands on a Mac mini. J. Cal thinks OpenClaw never makes mistakes. David thinks that's the most dangerous sentence in tech right now. In this episode, David and Dee go deeper on OpenClaw — the confidence cascade problem, agentic AI phases, what David Sachs gets right (and wrong) about knowledge workers, the atomized economy, and...

OpenClaw First Reactions | Boss Mode Podcast Ep. 21 AI agents are going rogue — and we're here for it. David and Dee break down the OpenClaw explosion: what it is, why it went viral overnight, whether it's actually useful or just a well-dressed intern, and what the rise of autonomous agents means for the future of work, UBI, and the humans left behind. From car negotiations to mass-texting...

What if the biggest shift in labor isn't AI replacing workers—but workers finally owning their time? Jarah Euston, CEO of Workwhile, joins your host David Lee, Cofounder of Vanka AI to challenge everything we think we know about employment, from why your employer is holding an interest-free loan of your paycheck to why 80 million Americans working frontline jobs have never had more choice. Thi...

Bernie Sanders calls AI companies "demonic." Alexander Wang says young people should spend all their time with AI. Who's right? David Lee and Dee Deng unpack the nuance between pro-human values and technological empowerment, landing on a surprising conclusion: people with ADHD might actually be the evolved humans perfectly suited for this moment. From SAT prep on Gemini to the indust...

What happens when a CEO decides to spend New Year's Day recreating The Matrix with nothing but AI tools and a laptop? Dee Deng joins David Lee to break down his viral AI-generated Matrix tribute, revealing which Chinese video models actually work, why infinite regenerations change everything, and how the barriers to filmmaking just collapsed. From Kling's kung fu scenes to Suno's two-p...

What happens when a software engineer turned investment manager meets the AI-powered future of work? Dr. Adam Link of Fireweed Capital joins David Lee to explore why contrarian thinking beats optimization in markets, the real debate between diversification and concentration, and how AI might transform everyone into 10x entrepreneurs. From the mountains of Alaska covered in fireweed to self-driving...

IRL Events in the Post-Employment Economy | BOSS MODE #016 Ritesh Patel, CEO of Ticket Fairy and Y Combinator alum, joins David Lee to discuss why in-person human connection will matter more than ever in the AI era—and how his platform is revolutionizing the live events industry. With 25 years of event production experience and over 400 events under his belt before founding Ticket Fairy, Ritesh sh...

David Lee sits down with Daria Kulachek, creator of the (Un)solicited Deck Peek newsletter and one of LA's go-to resources for tech events. They explore how AI is reshaping creativity, entrepreneurship, and the future of work—from the democratization of content creation to the declining need for startup capital. Topics include: the post-COVID return to in-person networking, AI fact-checking wo...

In this episode of the Boss Mode Podcast, David Lee sits down with Sam Hyun, the Director of Government Relations at the Asian American Foundation and co-founder of the sneaker brand 1587. They discuss the cultural significance of 1587, the challenges and opportunities faced by Asian Americans, the impact of automation on the job market, and the importance of resilience and mindset in navigating l...

From Orphan on the Streets to Successful Entrepreneur: Eric McDaniel's Incredible Journey | Boss Mode PodcastIn this powerful episode of the Boss Mode Podcast, David Lee and John Lagerling sit down with Eric McDaniel—a Korean adoptee who was abandoned on the streets of Seoul at age 3, adopted by an American family, and later returned to Korea to build multiple successful businesses in nightlif...

In this episode, Dee Deng (Founder & CEO of Right Hook Digital) takes us behind the scenes of a powerful marketing automation he built over a weekend using N8N. This is tactical, practical AI implementation at its finest. Dee walks through his custom-built workflow that transforms hours of manual research into automated competitive analysis for direct-to-consumer brands. The system automatical...

Amazon CEO Andy Jassy just dropped a bombshell: mass layoffs are "the new reality." In this Halloween episode of Boss Mode, we explore what happens when AI and robotics fundamentally transform the economy—from autonomous business creation to humanoid robots in your home. David Lee (Co-Founder, Vanka AI) and Dee Deng (Founder, Hook Digital) discuss how AI is reshaping agencies, what found...

We're announcing the Vanka Pre-Seed Fund - the world's first investment fund with 100% autonomous AI-driven investment decisions. No bias, no pattern matching, no "who you know" - just algorithmic evaluation of founders and ideas. What We're Offering: → $20K investments ($10K cash + $10K Vanka platform credits)→ One investment per month (Nov, Dec, Jan to start)→ 100% AI-based...

**Emergence Over Hierarchy** Why small, authentic teams win in the AI era. David Lee and John Lagerling go from a shaving “enforced focus” cold open to Hermann Hesse’s “true self,” debate whether “AI slop” is really slop, and map the shift from top-down orgs to emergent, vision-led creation. We dig into model alignment, trust, free-speech edge cases, the solopreneur wave, and the “de-bullshitifica...