Supra Insider

Apurva Garware, VP Product with leadership at Invisible Technologies, Upwork, Amazon and Microsoft. He argues systems thinking beats evals or prompt skills for AI products. Short takes cover handling non-determinism, designing guardrails, escalation heuristics, and building internal operational systems alongside customer products. Practical advice on starting with internal workflows and avoiding needless AI complexity.

Rishin Banker, VP of Product at Maven, leads product and process changes at a lean education startup. He describes shrinking pods to run 5–6 projects concurrently. Topics include front-loading strategy to parallelize work, non-EPD team members becoming builders, a design lead shipping end-to-end, deep investment in design systems, prototyping tied to real code, and new meeting rhythms for faster feedback.

Molly Siemers, an executive coach and former product leader from Kiva and Change.org, helps senior product leaders navigate overwhelm. She discusses why coaching demand has spiked, the difference between time and capacity, a three-step coaching framework (notice, decide, act), and practical practices to build personal capacity and reshape career identity.

Tom Charman, co-founder of Blok and builder of synthetic user simulation tools, explains how AI-driven personas can predict user behavior before launch. He discusses limits of A/B tests, how behavioral personas model emotion and memory, second- and third-order effects on retention, and using simulations to reduce bias and speed product decisions.

Tomer Cohen, former LinkedIn Chief Product Officer and advisor, champions the full stack builder mindset. He discusses collapsing process to idea→build→ship, how GPT-4 rewrote roadmaps, reimagining hiring with live product tests, three builder archetypes, and which human skills will endure as AI reshapes product work.

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.