Supra Insider

Michael Leibovich, an Adobe business unit leader who builds tools for creative pros, spent his paternity leave creating a personalized AI “chief of staff.” He breaks down the simple folders-and-markdown architecture, session memory, people files that auto-update from transcripts, Obsidian as a visual layer, and scheduled tasks that turn meetings into action. Practical playbook for busy operators and nontechnical builders.

Hiten Shah, serial entrepreneur who co-founded Crazy Egg and FYI and spent time as a PM at Dropbox, explores why top talent falters when the environment is wrong. He outlines a vibe→environment→culture framework. They discuss leadership blind spots, hiring for environment fit, when to reset systems, and using bots inside Slack to build products and workflows.

A deep dive into making fractional product work a sustainable career path. Practical advice on finding and pricing engagements, structuring retainers, and avoiding feast-or-famine income. Why narrow positioning and referrals beat broad marketing and aggregators. Concrete setup tips for legal, taxes, and scaling by productizing expertise.

Elan Miller, founder and CEO of design studio Off-Menu who advises brands on positioning and writes about brand strategy and AI. He breaks down why storytelling matters more in the AI era. He analyzes Anthropic’s positioning, explains why positioning must repel as well as resonate, and lays out when and how rebrands and brand tools actually move the needle.

Ben Guo, cofounder of Zo building a personal cloud computer with AI agents and developer tooling. He explains how Zo runs tasks via text or email, replaces small SaaS tools, and changes how teams plan by using AI-generated markdown plans reviewed as PRs. The conversation covers onboarding, delegation judgment, context management, and why personal cloud machines could become a common device.

Two co-hosts reflect on hitting a major milestone and the early doubts that almost stopped them. They talk about beating imposter syndrome, hiring an editor to make the show sustainable, and dropping scripted intros to find a more natural flow. They discuss instincts for picking guests, balancing timeless versus timely content, and how co-host chemistry and ritualized recording slots kept the project alive.

Yaniv Fatal, founding product manager at Blast Security and ex-Israeli Air Force pilot turned Wiz manager. He recounts applying pilot debrief routines to 20+ interview rejections, learning cloud security from zero in weeks, and earning credibility through small wins. He explains goal-setting with his wife, why product work trains future CEOs, and how relentless learning and asking 'dumb' questions accelerated his rise.

Gagan Biyani, CEO and co‑founder of Maven and serial edtech entrepreneur, explains why mid‑career professionals must double down on self‑learning. He talks about building the learning habit, the limits of social media, hands‑on practice and accountability, and why companies must redesign training and teams to actually adopt AI tools.

Chase Schwalbach, SVP of Product and Technology at Millie with deep healthcare and AI-building experience. He describes rolling up his sleeves to build HIPAA-compliant infra and an AI patient chatbot. Short takes cover building agent architectures, treating prompts like code, teaching himself evals, and why technical PMs and context engineering speed up product delivery.

Alexander Danilowicz, founder and CEO of Magic Patterns, builds an AI tool that focuses on front-end code and visual design. He explains why avoiding backend features improves prototyping quality. Conversation touches on who benefits from front-end-only tools, exports to design and code, maintaining product conviction, prompting best practices, and real-world team workflows.