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Go Unreasonably Deep, Stay Naive: Irving Fain, Bowery Farming, and a $300M Leap
Read more: Go Unreasonably Deep, Stay Naive: Irving Fain, Bowery Farming, and a $300M LeapIrving Fain’s path with Bowery Farming shows how naivety, paired with unreasonable depth, can crack complex markets like indoor farming. I break down why listening to skeptics, not just believers, accelerates product discovery and de-risks bold bets. You’ll see how a small-but-mighty team of five, hired for first-principles thinking, can outlearn incumbents. I share a…
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My Battle-Tested Comms Playbook: Kill Bad Stories, Create Categories, Lead With Clarity
Read more: My Battle-Tested Comms Playbook: Kill Bad Stories, Create Categories, Lead With ClarityI distill powerful communications and leadership lessons from a conversation with Shannon Brayton, a veteran operator who’s helped shape narratives at LinkedIn, OpenTable, eBay, Yahoo!, and Intuit. You’ll learn how to kill unhelpful stories, create categories that set market terms, and build trust with reporters through useful, accurate communication. I connect these comms tactics to…
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From Hair-on-Fire Problems to Product-Market Fit: Inside Pilot’s Human+Machine Playbook
Read more: From Hair-on-Fire Problems to Product-Market Fit: Inside Pilot’s Human+Machine PlaybookThis first-person breakdown distills Waseem Daher’s frameworks for validating startup ideas and building conviction. You’ll get a behind-the-scenes look at why Pilot chose a human plus machine model and how that shaped product discovery. I highlight how to define and test an ideal customer profile (ICP), and turn customer conversations into paying pilots. You’ll learn…
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From Dozens to Thousands: The People-First Playbooks and Pitfalls I’ve Learned to Avoid
Read more: From Dozens to Thousands: The People-First Playbooks and Pitfalls I’ve Learned to AvoidScaling teams tests people systems as much as product strategy. I unpack a candid conversation with McKenna Quint on when to rely on proven people-ops playbooks and when to start from first principles. We dig into a data-driven approach to attrition, introducing levels, hiring your first people leader, and making performance reviews work. I share…
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From Dropbox to Loom: Hard-Won, Sales-Driven Product Lessons for Competitive Markets
Read more: From Dropbox to Loom: Hard-Won, Sales-Driven Product Lessons for Competitive MarketsI sat down with Sam Taylor, VP of Sales and Success at Loom, whose career spans Dropbox’s first enterprise motion and Quip’s early sales leadership. His core lesson—that sales is an insight driver—translates directly into smarter pricing and packaging and a sharper, upmarket feature roadmap. From competing with giants like Google and Microsoft to partnering…
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Inside the Engineering Cultures of Microsoft, Reddit, Looker & Twitter: Hard-Won Lessons
Read more: Inside the Engineering Cultures of Microsoft, Reddit, Looker & Twitter: Hard-Won LessonsI unpack the most durable engineering and leadership practices from Nick Caldwell’s experiences at Microsoft, Reddit, Looker, and Twitter. From rigorous organizational design and regular org chart pruning to transparent performance systems and management training, I highlight what actually scales. I also share how a mission-driven culture sharpens leadership at high-visibility platforms and how to…
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Confidently Validate Product-Market Fit Before You Build: Inside UserLeap’s Playbook
Read more: Confidently Validate Product-Market Fit Before You Build: Inside UserLeap’s PlaybookDiscover how to validate product-market fit before writing a line of code. I share lessons from UserLeap’s early days, including market segmentation, customer conversations, and avoiding common PMF mistakes. Learn how to scope a first version, decide when to add features, and apply UserLeap’s 3 product principles daily. I also break down founder-led sales tactics…
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Retaining Startup Talent: Conflict Playbooks and Couples Therapy Tactics I Use
Read more: Retaining Startup Talent: Conflict Playbooks and Couples Therapy Tactics I UseI sat down with Flatiron Health’s Chief People Officer, Alex Buder Shapiro, to unpack how to retain startup talent and resolve conflict at work more effectively. We explored why couples therapy techniques like mirroring and naming feelings translate into faster repair and better decisions. I share my playbook for long-term employee retention, including hiring your…
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No UX Research Team? Proven Playbook to Validate Problems, Prototype Smart, and Nail Pricing
Read more: No UX Research Team? Proven Playbook to Validate Problems, Prototype Smart, and Nail PricingI sat down with Jane Davis to unpack a practical UX research playbook you can run without a dedicated team. She shares how to go end-to-end — from clarifying goals and asking the right questions to selecting participants and synthesizing insights. I translate her approach into lean product discovery tactics for early-stage startups, including prototyping,…
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Mastering Operational Complexity: Building Thirty Madison Without Upside-Down Unit Economics
Read more: Mastering Operational Complexity: Building Thirty Madison Without Upside-Down Unit EconomicsI explore how Thirty Madison scaled an operationally-intensive healthcare business while safeguarding margins from day one. You’ll see why conservative assumptions, rigorous line-item modeling, and inventive operational “unlocks” matter. We discuss treating internal operations as a marketplace and why unit economics won’t magically fix themselves at scale. I also share how to structure teams, when…
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From Painful Pivots to Product/Market Fit: 0→1 Lessons I Drew from Rupa Health’s CEO
Read more: From Painful Pivots to Product/Market Fit: 0→1 Lessons I Drew from Rupa Health’s CEOI break down the zero-to-one journey of Rupa Health’s CEO, highlighting the hard-won product/market fit lessons that matter most. Learn how to recognize when the first iteration isn’t working and why hiring before PMF can slow learning. See how stepping-stone products can open the right paths, even if they aren’t the final solution. Explore why…
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From Developer to CMO: Archana Agrawal’s Airtable & Atlassian Playbook for Product‑Led Growth
Read more: From Developer to CMO: Archana Agrawal’s Airtable & Atlassian Playbook for Product‑Led GrowthI sat down with Archana Agrawal, CMO of Airtable, to explore how horizontal products can sharpen their messaging without sacrificing flexibility. We discussed persona definition, product-led growth, and the tight alignment between product and marketing. She also walked through how she oversees multiple marketing functions and the rituals that keep her focused on the highest-leverage…
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