Psychotherapist Jillian O’Shea-Brown traces how founders’ ambition can grow from relational wounds, and how success rarely delivers the safety it promises. The conversation follows intuition, workplace trust and the difficult work of becoming less defensive and more fully oneself.

Eric Ries argues that companies become “sophisticated zombies” when shareholder primacy overwhelms their missions, and makes the case for governance structures built to defend purpose over time. The Lean Startup author outlines how boards, founders and consumers can reward long-term stewardship over extractive dealmaking.

Venture capitalist Bill Gurley makes the case that careers are built less by mythical mentors than by generous, candid peers. He and Molly Graham trace how reciprocal relationships, vulnerability and collective ambition can turn professional networks into engines of opportunity.

Ryan Carson and Claire Vo discuss the new work of solo founders managing fleets of coding agents, from cloud-based development and automated PR reviews to customer triage and investor updates. For all the software AI can produce, they argue, product-market fit still depends on leaving the screen to talk with actual people.

Enterprise sales veteran Jen Abel maps the 15-step path from first outreach to signed contract, arguing that information advantage and careful project management beat rigid scripts. The conversation treats demos, pilots and procurement as chances to build internal champions rather than merely advance a pipeline.

Product recruiter Chris Lee explains why job seekers should tailor their LinkedIn narratives to a specific target, treating the search as a test of candidate-market fit. He also walks through how recruiters scan profiles for stage, domain, seniority and hands-on AI experience before deciding whom to contact.

Semafor editor-in-chief Ben Smith makes the case for an anti-scale news business built on elite audiences, global events and aggressively independent reporting. He and Nilay Patel spar over creator economics, advisory boards, AI tools and whether audiences can still recognize journalism that refuses to be bought.

Town’s mayor argues that AI assistants should build themselves around users’ inboxes, calendars and work habits, turning private data into an evolving personal wiki. The conversation weighs the appeal of proactive software against the privacy, trust and job-displacement questions that follow.

Replit CEO Amjad Masad argues that AI agents are collapsing the boundaries between coding, design and management, turning companies into faster-moving networks rather than hierarchies. He sees a future of smaller firms, self-maintaining software and work measured less by output than by meaning.

Benchmark partner Sarah Tavel traces AI’s consumer future from Google’s technical beginnings to the product-led rise of social platforms. She argues that the next major AI company may turn prompt-sharing, personal agents and network effects into a genuinely social experience.

Being "layered" at work—when a company hires a new boss above you or splits your role—can feel like a demotion even when it is a necessary response to growth. Molly Graham and former CrossFit CEO Don Faul map out how employees and leaders can handle the bruised egos, hard conversations, and potential opportunity with care.

At the Toronto Product Conference, product leaders argue that side projects are becoming essential training for an AI-shaped workplace. Building real products, navigating technical tradeoffs and finding distribution can sharpen the judgment that PRDs alone cannot teach.

Bluesky CEO Tony Schneider makes the case for a social network built less like a walled garden than an open web, with portable identities, interoperable apps and user-controlled moderation. He also sketches a business model based on commerce and referrals rather than advertising, while confronting the app’s political reputation and the challenge of broadening its audience.

A Checkr executive explains why some big-company operators thrive at startups while others wash out, tracing the answer to humility, hands-on experience, and a precise fit between what a company needs and what a leader actually knows how to build. The conversation widens into a playbook for moving upmarket into enterprise sales, designing incentives, using AI in production, and making decisions that scale without smothering a company in process.

Gamma co-founder John Nerona traces the company’s pivot from a middling remote-work startup to an AI presentation juggernaut by attacking the blank page problem. He reflects on how early constraints, viral prosumer adoption, and an unplanned rush into enterprise forced the team to rethink product design, pricing, and what craftsmanship means in the age of fast-improving models.

Plaid COO Eric Sager describes how companies stay steady through shocks by treating acquisitions, pandemics and AI booms as milestones rather than identities, and by building a culture that prizes customers over short-term optics. He argues that organizational resilience comes from clear decision-making, spare capacity, frontline intimacy and leaders who reward behavior that strengthens the mission, not just the metrics.

Granola CEO Chris Pedregal talks with Every’s Dan Shipper about the knife-fight reality of building through the AI boom, where even breakout products feel precarious. Their conversation widens from meeting notes to the bigger contest over AI-native work: the interfaces, context, and invisible systems that could remake how people think and collaborate on the job.

Molly Graham talks with investor and former TaskRabbit CEO Stacey Brown-Philpott about treating religious faith as a real decision-making framework at work, not a private belief to be hidden from professional life. Their conversation moves from fundraising and leadership to boundaries, community, and the risks of making work the sole source of meaning.

A veteran product leader turned money coach talks through the strange blind spot of affluent tech workers: people who optimize everything at work while neglecting taxes, concentrated stock risk, estate planning and the mechanics of compounding. The conversation moves from his own career pivot to the emotional realities of sudden wealth, the limits of traditional financial advising and the practical habits that keep high earners from leaving fortunes on the table.

Molly Graham talks with executive recruiter Ify Walker about the "work twisties," the destabilizing loss of purpose and self-trust that can follow grief, burnout, or a career that no longer fits. Their conversation traces how Walker rebuilt her inner compass and why radical honesty matters in hiring, leadership, and figuring out where you actually belong.