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{ "episode": { "guest": "Brandon Chu", "expertise_tags": [ "Product Management", "Platform Strategy", "Remote Work Culture", "Writing & Communication", "Startup Founder", "VP of Product", "Developer Ecosystems", "Decision Making" ], "summary": "Brandon Chu, VP of Product at Shopify, discusses his journey from finance to product management through founding a startup called Tunezy. He shares insights on Shopify's product culture emphasizing technical excellence, collaborative decision-making, and founder mentality. The conversation covers Shopify's innovative remote-first infrastructure including \"bursts\" for team collaboration, the critical role of writing in PM career development, and platform product management principles. Brandon highlights how his writing accelerated his career, the importance of understanding constituent trade-offs in ecosystem design, and advice for PMs to build side projects to gain holistic business understanding.", "key_frameworks": [ "PM Job Description: Help teams ship the right thing at the right time in the right way", "Decision Importance Framework: Reversibility, user impact, and team velocity", "Annual Investment Planning Cycle: Set broad direction, allow team autonomy for execution", "Platform PM Psychology: Long cycles (5-10x longer), celebrate incremental wins", "Constituent Stack Ranking: Define clear principles for multi-stakeholder trade-offs", "Founder Skills for Leadership: Storytelling, team motivation, high-conviction decisions, accountability", "Remote Work Optimization: Bursts for high-velocity creative work, distributed infrastructure" ] }, "topics": [ { "id": "topic_1", "title": "Brandon's Background: From Astronaut Dreams to Product Management", "summary": "Brandon shares his childhood aspiration to be an astronaut and his long-term space travel plans. He discusses his path from finance and Kraft Foods through founding Tunezy, a YouTube musician monetization platform, to eventually breaking into product management at FreshBooks.", "timestamp_start": "00:03", "timestamp_end": "05:50", "line_start": 1, "line_end": 50 }, { "id": "topic_2", "title": "Shopify Career Trajectory and PM Skills Development", "summary": "Brandon details his seven-year journey at Shopify starting from the IPO, various PM roles, and how domain expertise in platform management and developer ecosystems led to director and VP positions. He explains the founder skills that accelerated his career beyond table-stakes PM competencies.", "timestamp_start": "05:50", "timestamp_end": "08:47", "line_start": 50, "line_end": 66 }, { "id": "topic_3", "title": "Shopify's Product Culture and Values", "summary": "Brandon describes Shopify's unique product culture characterized by technical excellence, distributed product thinking across all functions, founder mentality, and empathy for entrepreneur customers. He explains the PM job description: 'Help teams ship the right thing at the right time in the right way.'", "timestamp_start": "08:47", "timestamp_end": "12:00", "line_start": 66, "line_end": 81 }, { "id": "topic_4", "title": "Decision Making Frameworks at Shopify Scale", "summary": "Brandon explains Shopify's annual investment planning cycle that sets directional north stars and vision statements. He discusses how teams operate with autonomy while maintaining alignment, the importance of never falling into sunk-cost fallacy, and willingness to pivot when the world changes.", "timestamp_start": "12:00", "timestamp_end": "16:03", "line_start": 81, "line_end": 103 }, { "id": "topic_5", "title": "Shopify's COVID-19 Response and Product Pivots", "summary": "Brandon details how Shopify pivoted during COVID when brick-and-mortar retail collapsed. The company shifted from 40 planned features to focusing on three critical features: online ordering, curbside pickup, and gift cards. Teams rallied across the organization with wartime mentality to ship in weeks.", "timestamp_start": "16:03", "timestamp_end": "19:58", "line_start": 103, "line_end": 130 }, { "id": "topic_6", "title": "Remote-First Culture and the 'Bursts' System", "summary": "Brandon explains Shopify's remote-first approach originating from Ottawa roots. He describes 'bursts'—quarterly team gatherings in curated locations with in-house infrastructure handling all logistics, flights, hotels, and accommodations. The system includes data tracking to ensure team connection and engagement.", "timestamp_start": "19:58", "timestamp_end": "24:42", "line_start": 130, "line_end": 156 }, { "id": "topic_7", "title": "Writing as Career Accelerator and Clarification Tool", "summary": "Brandon discusses his Medium writing from 2018 and prior years, emphasizing that writing clarifies thinking rather than sharing established expertise. He invested 40 hours per post through iterative drafting and feedback. The process forced him to disambiguate chaos in his mind about his PM role.", "timestamp_start": "24:42", "timestamp_end": "29:14", "line_start": 156, "line_end": 184 }, { "id": "topic_8", "title": "The Impact of Writing on Career and Company Culture", "summary": "Brandon details concrete career impacts from his writing: new team members pre-onboarded through reading his posts, influence over internal priorities, building trust with Tobi, and attracting high-quality PMs to Shopify. He shares the Facebook Messenger integration post example where external validation translated to internal credibility.", "timestamp_start": "29:14", "timestamp_end": "35:41", "line_start": 184, "line_end": 256 }, { "id": "topic_9", "title": "Decision-Making Post: The Framework That Resonates Most", "summary": "Brandon's most popular and enduring post argues that PMs should prioritize decisions by importance (reversibility, user impact) and spend disproportionate time on few critical decisions while delegating or intuiting the rest. This framework remains his primary operating principle as an executive.", "timestamp_start": "35:41", "timestamp_end": "38:31", "line_start": 256, "line_end": 283 }, { "id": "topic_10", "title": "Platform PM: Desired Future Writing and Problem Domain", "summary": "Brandon describes his unwritten post on platform PM versus product PM. He discusses the unique challenges: longer cycles (5-10x), multi-party stakeholders, policy tensions, and design problems like embedding third-party UIs. Examples include Facebook Messenger integration and iOS app shortcuts architecture.", "timestamp_start": "38:31", "timestamp_end": "41:18", "line_start": 283, "line_end": 298 }, { "id": "topic_11", "title": "Platform PM Psychology and Principles", "summary": "Brandon explains the psychological shift required for platform work: longer feedback cycles, celebrating infrastructure milestones without end-user impact, and defining constituent principles upfront. He compares Amazon's consumer-focused principle versus Shopify's merchant-focused approach and second-order effects of these trade-offs.", "timestamp_start": "41:18", "timestamp_end": "45:07", "line_start": 298, "line_end": 319 }, { "id": "topic_12", "title": "Choosing Between Platform and User-Facing PM Tracks", "summary": "Brandon addresses whether platform PM is a one-way door, arguing it's not. He explains that oscillating between platform and product work is valuable—platform work teaches constraint and canvas design, while user-facing work provides rapid iteration and feedback. Both experiences are complementary.", "timestamp_start": "45:07", "timestamp_end": "47:00", "line_start": 319, "line_end": 328 }, { "id": "topic_13", "title": "Top Career Advice: Building Side Projects and Breaking Through Technical Walls", "summary": "Brandon's primary advice for PM career development: start a legitimate side hustle to understand sales, support, and shipping. For non-technical PMs, he recommends learning to build simple products through tutorials to demystify technology and break through technical obscurity, providing confidence for future technical collaboration.", "timestamp_start": "47:00", "timestamp_end": "48:43", "line_start": 328, "line_end": 337 }, { "id": "topic_14", "title": "Brandon's Current Work and How to Connect", "summary": "Brandon discusses his current role leading product acceleration at Shopify, managing the company's investment portfolio. He shares that he's an active angel investor in 60 companies and encourages people to help others rather than expecting return favors from him given his good fortune.", "timestamp_start": "48:43", "timestamp_end": "49:33", "line_start": 337, "line_end": 351 } ], "insights": [ { "id": "i1", "text": "Founder skills are the limiting factor for high-level PM careers. Beyond table-stakes skills (analytical, technical, communication), leaders need storytelling ability, talent motivation, high-conviction decision-making in ambiguity, and personal accountability.", "context": "Brandon contrasts commodity PM skills with founder-mentality differentiators that propelled his career.", "topic_id": "topic_2", "line_start": 61, "line_end": 66 }, { "id": "i2", "text": "Shopify's core PM principle distributes product responsibility across all functions rather than centralizing it. Everyone from engineers to support owns product thinking; PMs serve as servant leaders helping teams achieve the right outcome.", "context": "Explains the fundamental difference in Shopify's collaborative culture versus traditional hierarchical PM structures.", "topic_id": "topic_3", "line_start": 70, "line_end": 81 }, { "id": "i3", "text": "Technical company cultures create different collaboration dynamics. When all tools require code literacy (GitHub for management, committing blog posts), it eliminates hierarchies and ensures everyone engages deeply with product mechanics.", "context": "Brandon describes Shopify's all-technical infrastructure as a cultural artifact that democratizes product thinking.", "topic_id": "topic_3", "line_start": 70, "line_end": 75 }, { "id": "i4", "text": "The founder mentality in hiring creates mutual empathy with customers. Shopify intentionally staffs 30-40% of PMs with failed founders because building a platform for entrepreneurs requires lived understanding of entrepreneurship.", "context": "Brandon explains how founder experience translates into customer empathy and product intuition.", "topic_id": "topic_3", "line_start": 76, "line_end": 81 }, { "id": "i5", "text": "PM decision authority should increase with seniority. Junior PMs should practice balanced decision-making across functions. Directors and above own strategic direction entirely—their job is to commit to a direction and be accountable, even if team members initially resist.", "context": "Brandon describes Shopify's evolved approach to decision rights as the company scaled and roles matured.", "topic_id": "topic_4", "line_start": 85, "line_end": 87 }, { "id": "i6", "text": "Annual investment plans should set broad directional north stars, not detailed execution specs. Teams need autonomy to iterate toward goals because the world changes continuously. Never fall into sunk-cost fallacy—abandon projects mid-execution if context shifts.", "context": "Brandon explains Shopify's planning cycle as deliberate ambiguity that enables flexibility and rapid pivots.", "topic_id": "topic_4", "line_start": 91, "line_end": 102 }, { "id": "i7", "text": "Crisis reveals cultural resilience. Companies with strong product cultures can instantly pivot away from months of planning when circumstances demand it. Shopify went from executing 40 planned features to shipping 3 mission-critical features in weeks during COVID.", "context": "Brandon contrasts Shopify's swift pivot with risk-averse cultures that can't abandon sunk work.", "topic_id": "topic_5", "line_start": 112, "line_end": 123 }, { "id": "i8", "text": "Remote work isn't about elimination of in-person time; it's about intentionality. In-person time should maximize high-velocity creative collaboration, not routine communication. Infrastructure investment (flights, hotels, logistics automation) removes friction from connection.", "context": "Brandon explains Shopify's counterintuitive solution to remote work: more strategic in-person time, not less.", "topic_id": "topic_6", "line_start": 133, "line_end": 156 }, { "id": "i9", "text": "The writing process itself is the primary value, not the output. Writing forces disambiguation of fuzzy thinking. Whether or not posts go viral, the act of writing clarifies mental models and improves oral communication clarity with teams.", "context": "Brandon reflects that writing in 2018 or prior clarified his thinking contemporaneously, not years later.", "topic_id": "topic_7", "line_start": 172, "line_end": 183 }, { "id": "i10", "text": "Rapid career transitions create contrast that feeds writing. Brandon could observe context shifts (same role in different companies, same company at different scales) which generated unique insights. Slow career progression yields less material for writing.", "context": "Brandon explains why his most prolific writing happened during years of rapid role changes.", "topic_id": "topic_7", "line_start": 172, "line_end": 180 }, { "id": "i11", "text": "Writing quality requires aggressive iteration. Brandon estimates 40 hours per post: 2 hours drafting, 38 hours editing and gathering feedback. He wasn't afraid to share raw early drafts with objective readers to learn how his narrative landed versus intended.", "context": "Brandon describes the high effort investment that distinguishes useful writing from casual thoughts.", "topic_id": "topic_7", "line_start": 179, "line_end": 183 }, { "id": "i12", "text": "External validation cascades into internal influence. Brandon's publicly shared posts built his 'trust battery' with leadership (Tobi) and attracted high-quality PMs seeking to work for him. External momentum creates internal political capital more effectively than internal lobbying.", "context": "Brandon describes surprised himself by the ROI of external writing on internal organizational influence.", "topic_id": "topic_8", "line_start": 241, "line_end": 256 }, { "id": "i13", "text": "Writing during hyperscale growth solves onboarding at scale. As companies grow rapidly, writing becomes a one-to-many communication mechanism that onboards new hires on leadership philosophy and culture without individual meetings.", "context": "Brandon explains how his writing pre-onboarded team members joining his organization.", "topic_id": "topic_8", "line_start": 230, "line_end": 242 }, { "id": "i14", "text": "High-profile outside validation (like David Marcus sharing a Facebook Messenger post) accelerates internal perception shifts. Peer credibility from respected industry figures influences how executives perceive your competence.", "context": "Brandon shares specific example of how external endorsement from PayPal/Facebook leadership elevated his internal status.", "topic_id": "topic_8", "line_start": 245, "line_end": 249 }, { "id": "i15", "text": "Decision importance framework: PMs face hundreds of decisions but should rigorously separate critical from trivial. Critical decisions are irreversible or affect large user populations materially. For trivial decisions, delegate or gut-call quickly to maintain team velocity.", "context": "Brandon's most popular and enduring post argues for radical prioritization of PM attention.", "topic_id": "topic_9", "line_start": 265, "line_end": 270 }, { "id": "i16", "text": "Battle scars recalibrate decision importance. After making decisions you feared would be career-ending that had no negative outcome, you raise your bar for what's actually important. Experience and resilience together prevent over-weighting trivial decisions.", "context": "Brandon reflects on how experience in role leads to better decision calibration.", "topic_id": "topic_9", "line_start": 281, "line_end": 282 }, { "id": "i17", "text": "Platform PM requires psychological adjustment to very long feedback cycles. Traditional PM cycles are weeks/months; platform cycles are 5-10x longer. Teams must celebrate incremental infrastructure wins (API alpha release) without waiting for end-user impact validation.", "context": "Brandon explains the fundamental psychological difference between platform and product management.", "topic_id": "topic_11", "line_start": 307, "line_end": 317 }, { "id": "i18", "text": "Platform principles should explicitly stack-rank constituents for policy trade-offs. Amazon prioritizes consumers over sellers; Shopify prioritizes merchants over developers. These principles cascade through policy, data sharing, and feature design. Lack of clarity leads to launch-day CEO vetoes.", "context": "Brandon explains how Shopify learned to make multi-stakeholder trade-offs explicit rather than emergent.", "topic_id": "topic_11", "line_start": 311, "line_end": 317 }, { "id": "i19", "text": "Embedding third-party products inside platforms requires nuanced technical and UX design. Deep integration (third-party UI served by first-party server with hybrid data flow) is superior to shallow integration (external links) but introduces design challenges around power, data control, and user experience.", "context": "Brandon discusses the complexity of platform design decisions using iframe versus native integration examples.", "topic_id": "topic_10", "line_start": 287, "line_end": 297 }, { "id": "i20", "text": "Platform and user-facing PM work are complementary, not exclusive. Oscillating between them is ideal—platform work teaches constraint and canvas design, product work provides rapid feedback. Both experiences strengthen overall PM judgment.", "context": "Brandon argues against platform PM being a career dead-end or one-way door.", "topic_id": "topic_12", "line_start": 322, "line_end": 327 }, { "id": "i21", "text": "Side projects demystify technology and business operations simultaneously. Building a minimal viable product teaches selling, support, shipping, and resilience to failure in ways employment never can. This humbles PMs and builds empathy for cross-functional challenges.", "context": "Brandon recommends side hustles as the single most impactful PM development activity.", "topic_id": "topic_13", "line_start": 331, "line_end": 336 }, { "id": "i22", "text": "Non-technical PMs can break through technical obscurity with minimal effort. Following a Rails tutorial to build a Twitter clone takes a weekend and demystifies the impossibility of technology. Once PMs ship something themselves, they collaborate more effectively with engineers.", "context": "Brandon encourages non-technical PMs to lower the barriers to learning by building simple projects.", "topic_id": "topic_13", "line_start": 331, "line_end": 336 }, { "id": "i23", "text": "Writing shouldn't be motivated by virality. The more a PM focuses on external validation and traction, the less likely the writing becomes valuable. Authentic exploration of ideas produces better outcomes than attempt to make something go viral.", "context": "Brandon reflects on why he stopped writing despite earlier success—he feared disappointing audiences with less polished work.", "topic_id": "topic_7", "line_start": 257, "line_end": 261 }, { "id": "i24", "text": "Transparency about stopping writing: Brandon stopped because executive demands exceeded writing capacity and he wouldn't compromise quality. Perfectionism prevents shipping, but shipping lower-quality work at scale also carries reputational risk.", "context": "Brandon acknowledges the tension between consistency and quality that led to his three-year writing hiatus.", "topic_id": "topic_7", "line_start": 259, "line_end": 261 }, { "id": "i25", "text": "PM role definition shifts with scale. In small companies, PMs are decision-makers and operators. At large scale (12,000+ people), PM role becomes purely strategic—setting direction and being accountable for that bet, not executing details.", "context": "Brandon describes how his PM role fundamentally changed as Shopify scaled 25x during his tenure.", "topic_id": "topic_2", "line_start": 53, "line_end": 56 } ], "examples": [ { "id": "ex1", "explicit_text": "I kind of broke into product management is I got really bored that really quickly. And I started moonlighting and bootstrapping a startup on the side and it was called Tunezy and it helped YouTube musicians at the time, which were blowing up. This is kind of when Justin Bieber was becoming famous by doing webcam cover music and stuff like that. And we helped YouTube musicians monetize their fan bases by offering fan experiences at their tour stops.", "inferred_identity": "Brandon Chu's startup, Tunezy", "confidence": "explicit", "tags": [ "Brandon Chu", "Founder", "Startup", "YouTube Musicians", "Monetization", "Fan Experiences", "Early Stage", "Pre-product category" ], "lesson": "Side projects teach complete business skills including sales, support, and shipping. Breaking into product management through founding reveals the full business cycle beyond feature development.", "topic_id": "topic_1", "line_start": 46, "line_end": 50 }, { "id": "ex2", "explicit_text": "And so I kind of entered a lot of startup competitions and we got some funding and some office space and we quit our jobs literally the weekend after we won that.", "inferred_identity": "Tunezy winning startup competition", "confidence": "explicit", "tags": [ "Startup Competition", "Tunezy", "Funding", "Office Space", "Founder Commitment", "Scrappy Entrepreneurship" ], "lesson": "Winning validation (competitions, funding) can be the catalyst to commit fully to an idea. Moment-of-commitment decisions compound confidence and momentum.", "topic_id": "topic_1", "line_start": 47, "line_end": 50 }, { "id": "ex3", "explicit_text": "And then fast forward three and a half, four years, we never really made a really big company out of it, but we kind of soft landed sold the company.", "inferred_identity": "Tunezy acquisition", "confidence": "explicit", "tags": [ "Tunezy", "Acquisition", "Soft Landing", "Founder Exit", "Failed Scale", "Learning", "Product Management Entry" ], "lesson": "Not every startup needs massive scale to generate learning. Modest exits provide founder experience and transition points into other roles like product management.", "topic_id": "topic_1", "line_start": 49, "line_end": 50 }, { "id": "ex4", "explicit_text": "I joined a growth stage startup in Canada, in Toronto called FreshBooks, which is still around today. They're a Series D company now. And I kind of learned the chops of product management there because the folks there were X Microsoft 15 years, really technical, process-oriented and framework heavy product management.", "inferred_identity": "FreshBooks", "confidence": "explicit", "tags": [ "FreshBooks", "Toronto", "Growth Stage", "Series D", "Former Microsoft PMs", "Process-oriented", "Framework-heavy", "PM Skills Development" ], "lesson": "Joining companies with experienced PM leaders from large organizations provides structured PM training. Exposure to process-oriented, framework-heavy thinking develops PM fundamentals before joining scale-stage companies.", "topic_id": "topic_2", "line_start": 50, "line_end": 53 }, { "id": "ex5", "explicit_text": "And then I joined Shopify the week of the IPO actually. So that's almost seven years ago and it was one of the largest companies I ever worked at. I had 500 people even then at least because I'd been in startups prior.", "inferred_identity": "Shopify IPO join", "confidence": "explicit", "tags": [ "Shopify", "IPO Week", "Timing", "500 People", "Scale Jump", "Career Inflection", "Seven Years" ], "lesson": "Joining a company during inflection points (IPO, rapid scaling) accelerates learning. Brandon went from startups to 500-person organization, experiencing multiple scaling cycles over seven years.", "topic_id": "topic_2", "line_start": 53, "line_end": 53 }, { "id": "ex6", "explicit_text": "Shopify has an incredibly strong product culture. Whether it's uniquely different, I can't know for sure, but I would say I'd start with, it's a highly technical company. That's not unique, but it's just something that should be known about Shopify. When I joined, all project management was just in GitHub, just commenting on poll requests and even marketers in order to augment or upload a blog post, you'd have to commit and deploy it.", "inferred_identity": "Shopify's technical culture", "confidence": "explicit", "tags": [ "Shopify", "Technical Culture", "GitHub", "All-in-code workflows", "High barrier to entry", "Cultural artifact", "Developer founder legacy" ], "lesson": "All-code infrastructure (GitHub for all project management, commits for blog posts) creates cultural democratization. Non-technical roles must engage with code, eliminating silos and building shared context.", "topic_id": "topic_3", "line_start": 70, "line_end": 75 }, { "id": "ex7", "explicit_text": "And so because of that, I think everyone in the company had their hands really deep in the product regardless of what function you are, which brings me the second thing I think is really awesome with Shopify, when it comes to how the product org works, it's that we don't actually put the product org on a pedestal as the only people that can have an opinion about the product or should be listened to when we think about what should be built.", "inferred_identity": "Shopify product philosophy", "confidence": "explicit", "tags": [ "Shopify", "Product Culture", "Distributed Ownership", "No PM Pedestal", "Cross-functional Collaboration", "Engineer Input", "Support Input" ], "lesson": "Distributed product ownership prevents PM siloing. When engineers, support, and sales all have legitimate product voices, decision quality improves and implementation speed accelerates.", "topic_id": "topic_3", "line_start": 73, "line_end": 74 }, { "id": "ex8", "explicit_text": "And so that's some of the foundations of it. And again, all stems from Tobi. I'd say the last one is that this comes from the fact that we have Canadian roots. And I say that actually in a way that's almost opposite of the stereotype when it comes to tech anyway. There has been a lot of failed tech companies in Canada and no company that's ever truly been global. And so ambition and a founder mentality has been something that we've architected the culture of the product team around. And so 30 to 40% of the PM team are ex founders either through failed startups or through acquisition.", "inferred_identity": "Shopify hiring philosophy", "confidence": "explicit", "tags": [ "Shopify", "Founder Hires", "30-40% ex-founders", "Canadian Tech Context", "Ambition as Culture", "Failed Startups", "Acquisitions", "Founder Mentality" ], "lesson": "Explicitly hiring founders into PM roles compounds founder mentality. This strategy creates mutual empathy with entrepreneur customers and brings grit, versatility, and growth mindset to product teams.", "topic_id": "topic_3", "line_start": 76, "line_end": 78 }, { "id": "ex9", "explicit_text": "During COVID, this cultural resilience we had to change was so vital because all of a sudden, these grandiose ideas and visions we had for 2020 didn't matter and what mattered was like, 'Oh, shit. Retail businesses are going from a hundred percent to zero.' It's like 0% revenue overnight. And how do we help a brick and mortar store across the street now do order online and pick up it in store?", "inferred_identity": "Shopify COVID pivot", "confidence": "explicit", "tags": [ "Shopify", "COVID-19", "Retail Crisis", "Business Closure Risk", "Order Online Pickup", "Curbside", "Merchant Survival", "Wartime Product" ], "lesson": "Crises demand complete strategy reset. Shopify's ability to abandon months of planning and refocus on merchant survival in weeks revealed the strength of its decision-making culture.", "topic_id": "topic_5", "line_start": 106, "line_end": 108 }, { "id": "ex10", "explicit_text": "And so of course, online only merchants or merchants who were well established online have that infrastructure. There wasn't supply chain issues yet. So they're good. The focus then turned, of course, to all these both hybrid brick and mortar online customers and customers that are only brick and mortar. And so we did all those things. Some restaurants and grocery stores on the platform, how do we help them do exactly that buy online, pick up at the curb? How do we help them launch buy gift cards now at a discount so that basically you can, as a consumer, help these companies stay afloat.", "inferred_identity": "Shopify COVID feature prioritization", "confidence": "explicit", "tags": [ "Shopify", "COVID-19", "Gift Cards", "Discount Promotion", "Restaurants", "Grocery Stores", "Hybrid Merchants", "Merchant Support" ], "lesson": "COVID accelerated feature deployment for merchant survival. Gift cards became mission-critical infrastructure when physical retail collapsed; Shopify shipped what was previously a non-critical app feature in weeks.", "topic_id": "topic_5", "line_start": 114, "line_end": 122 }, { "id": "ex11", "explicit_text": "So these things exist on Shopify in apps because they were never really mission critical, but now it became really mission critical. So all of a sudden we're trying to gear 500 people towards ship gift cards, which sounds like a really small feature, but it's pretty hard when you have millions of merchants and hundreds of millions of consumers using your platform every day, ship it in two weeks.", "inferred_identity": "Shopify gift cards feature", "confidence": "explicit", "tags": [ "Shopify", "Gift Cards", "Feature", "Two Week Timeline", "Scale Complexity", "500 People Alignment", "Millions of Merchants", "High Stakes" ], "lesson": "Scale changes feature difficulty exponentially. Gift cards seems simple until you ship to millions of merchants and hundreds of millions of consumers in two weeks.", "topic_id": "topic_5", "line_start": 122, "line_end": 123 }, { "id": "ex12", "explicit_text": "And so it became war time truly. And yes, Tobi got way more involved, as did Craig Miller, our CPO at the time. And we went down from trying to ship maybe the 40 things that quarter to three and nothing else mattered.", "inferred_identity": "Shopify leadership during COVID", "confidence": "explicit", "tags": [ "Shopify", "Tobi Lutke", "Craig Miller", "CPO", "CEO Involvement", "Wartime Leadership", "40 to 3 features", "Priority Collapse" ], "lesson": "CEO involvement in wartime signals priority shift. Shopify collapsed from 40 planned quarterly features to 3; CEO and CPO alignment amplified focus.", "topic_id": "topic_5", "line_start": 122, "line_end": 123 }, { "id": "ex13", "explicit_text": "We made the decision very early in the pandemic to say, 'We're never going to have offices again. We're a digital by default company. Hire anywhere in the world, but let's make sure we have really great infrastructure.' And so there was so many things happening inside the company that just changed. It really changed overnight.", "inferred_identity": "Shopify remote-first decision", "confidence": "explicit", "tags": [ "Shopify", "Remote-first", "COVID-19", "Distributed Team", "Hire Anywhere", "Infrastructure Investment", "Overnight Shift", "Cultural Pivot" ], "lesson": "Early remote-first commitment during COVID transformed culture overnight. Shopify pivoted from office-optional to office-never, enabling global hiring and distributed work infrastructure.", "topic_id": "topic_6", "line_start": 127, "line_end": 129 }, { "id": "ex14", "explicit_text": "What we've done is we've actually instituted with something we call bursts. So bursts at Shopify are the ability for your team generally maybe once a quarter or whatnot, to just come together to do really high velocity creative work together, to hang out together. And so we've gone pretty far on this where we actually have in-house built web and mobile apps that allow teams to one click, say I have 20 people. We want to do a burst in Laguna Beach and then click the button and then flights get booked, hotels get booked, food is taken care of.", "inferred_identity": "Shopify bursts program", "confidence": "explicit", "tags": [ "Shopify", "Bursts", "In-person Meetings", "Quarterly Offsite", "Creative Work", "Logistics Automation", "Laguna Beach", "Team Building" ], "lesson": "Removing friction from in-person gatherings enables cultural bonding at scale. One-click offsite booking (flights, hotels, meals) removes logistical burden and democratizes team connection.", "topic_id": "topic_6", "line_start": 133, "line_end": 137 }, { "id": "ex15", "explicit_text": "And I actually worked out of the Caribbean for five weeks in March. And because we also had a policy that we instituted that said for 90 days out of the year, you can work in any country you want.", "inferred_identity": "Brandon Chu working from Caribbean", "confidence": "explicit", "tags": [ "Brandon Chu", "Shopify", "Remote Work", "Caribbean", "90 Day Policy", "Distributed Work", "Location Freedom", "Global Workforce" ], "lesson": "Explicit remote work policies unlock global lifestyle flexibility. Shopify's 90-day international work policy allows employees to work from anywhere, transforming remote work from constraint into benefit.", "topic_id": "topic_6", "line_start": 142, "line_end": 144 }, { "id": "ex16", "explicit_text": "I'm going next week actually to one with our team.", "inferred_identity": "Brandon Chu's upcoming burst", "confidence": "implicit", "tags": [ "Brandon Chu", "Shopify", "Bursts", "Team Connection", "Regular Participation", "Leadership Example" ], "lesson": "Leadership participation in team activities validates the program and models remote work culture. Brandon's active burst attendance demonstrates that executives also prioritize team connection.", "topic_id": "topic_6", "line_start": 137, "line_end": 137 }, { "id": "ex17", "explicit_text": "I think I wrote those in a time where I was figuring out a lot of stuff while I was executing. And I wanted to crystallize in my mind some mental models and frameworks that had been forming somewhat intuitively.", "inferred_identity": "Brandon Chu's Medium writing motivation", "confidence": "explicit", "tags": [ "Brandon Chu", "Writing", "Mental Models", "Framework Development", "Execution Learning", "Crystallization", "Self-education" ], "lesson": "Writing during active execution clarifies emerging mental models. Deliberate reflection through writing accelerates learning from experience.", "topic_id": "topic_7", "line_start": 172, "line_end": 174 }, { "id": "ex18", "explicit_text": "I figured out everything in those posts at the exact moment I wrote them. It was the writing process itself that actually allowed me to solidify those mental models and those frameworks in my mind. And so I wasn't ahead of the game in any way.", "inferred_identity": "Brandon Chu's writing process insight", "confidence": "explicit", "tags": [ "Brandon Chu", "Writing", "Learning", "Real-time Learning", "Not Ahead", "Process Value", "Thinking Tools" ], "lesson": "Writing doesn't transmit pre-formed expertise; it forms expertise through the act of writing. Brandon's most useful posts came from simultaneous discovery, not accumulated wisdom.", "topic_id": "topic_7", "line_start": 173, "line_end": 177 }, { "id": "ex19", "explicit_text": "I was moving through things really quickly so I was able to contrast things because it was literally like, 'Oh wait, three months ago, it was that. Now, how do I change?'", "inferred_identity": "Brandon Chu's rapid career transitions", "confidence": "implicit", "tags": [ "Brandon Chu", "Career Transitions", "Rapid Movement", "Contrast Learning", "Context Switching", "Observation" ], "lesson": "Rapid career transitions (Tunezy → FreshBooks → Shopify scaling) provide contrast that generates insights. Static roles generate fewer observations.", "topic_id": "topic_7", "line_start": 176, "line_end": 177 }, { "id": "ex20", "explicit_text": "We grew seven years ago. I came at just under 500 people. Were over 12,000 people today.", "inferred_identity": "Shopify growth over Brandon's tenure", "confidence": "explicit", "tags": [ "Shopify", "Growth", "500 to 12000", "25x Scaling", "Seven Years", "Brandon Chu", "Formative Period" ], "lesson": "Scaling through 25x growth creates constant contrast and learning. Brandon witnessed the company transform from IPO-week (500 people) to 12,000+, providing rich material for writing.", "topic_id": "topic_7", "line_start": 178, "line_end": 180 }, { "id": "ex21", "explicit_text": "I put 40 hours into a post, do it on the weekends or I brain dumped a first draft of it in two hours and drew 38 hours of editing or getting feedback from people or drawing some diagrams that I put in there.", "inferred_identity": "Brandon Chu's writing effort distribution", "confidence": "explicit", "tags": [ "Brandon Chu", "Writing", "40 hours", "Editing", "Feedback", "Quality", "Iteration", "Effort Investment" ], "lesson": "High-quality writing requires disproportionate editing. Brandon's 40-hour posts were 5% drafting, 95% editing/feedback cycles, demonstrating that writing quality comes from revision.", "topic_id": "topic_7", "line_start": 179, "line_end": 180 }, { "id": "ex22", "explicit_text": "people that would join my team already knew how I thought. It was pretty onboarded a lot of the PMs that would join my team because obviously, they're going to look for who their leads is and Google that a bit and they see a posting and be like, 'Is this person legit or not or whatever?' And so I didn't really even have to onboard many people in so many ways.", "inferred_identity": "Brandon Chu's writing impact on team hiring", "confidence": "implicit", "tags": [ "Brandon Chu", "Writing", "Hiring", "Pre-onboarding", "Credibility", "Team Building", "Thought Leadership" ], "lesson": "Public writing pre-onboards team members. New hires who read Brandon's posts came already aligned with his thinking, reducing onboarding friction.", "topic_id": "topic_8", "line_start": 241, "line_end": 243 }, { "id": "ex23", "explicit_text": "I actually found that writing externally and getting momentum externally was a better way to influence internally what was happening, to the effect that Tobi would read my post here and there and he'd be like, 'Great post.' And I'd be like, 'Hey, daddy loves me.'", "inferred_identity": "Brandon Chu's external writing influence on Tobi Lutke", "confidence": "explicit", "tags": [ "Brandon Chu", "Writing", "Tobi Lutke", "Internal Influence", "External Validation", "Trust Building", "Leadership Approval", "Indirect Influence" ], "lesson": "External influence accumulates internal credibility. Brandon's publicly-shared posts read by Tobi built trust more effectively than internal proposals.", "topic_id": "topic_8", "line_start": 243, "line_end": 244 }, { "id": "ex24", "explicit_text": "Every week a new PM messages me and says like, 'Hey. I just joined. Your post had a lot of influence on me or whatever. And I'd love to meet up and blah, blah, blah.'", "inferred_identity": "Brandon Chu as PM thought leader", "confidence": "implicit", "tags": [ "Brandon Chu", "Writing", "Recruitment", "Thought Leadership", "PM Attraction", "Ongoing Impact", "Community Building" ], "lesson": "Writing attracts talent. Weekly messages from new Shopify PMs citing Brandon's writing as influence demonstrates writing's ongoing talent magnetism.", "topic_id": "topic_8", "line_start": 245, "line_end": 245 }, { "id": "ex25", "explicit_text": "I was working on the integration product with Facebook Messenger via Shopify. And as part of our launch, I wrote just to get more, because we're a very small company than them. So we're using any angle we can. So I'm writing on my personal blog about this thing that we launched and David Marcus, who's now leading their blockchain crypto stuff, but he was CEO of PayPal for a while. And then he came in to lead all the Facebook's payment stuff and Messenger. Oh, sorry. Kind of lead Messenger. Anyway, he shared it on his Facebook and on Twitter.", "inferred_identity": "David Marcus endorsement of Shopify blog post", "confidence": "explicit", "tags": [ "Shopify", "Facebook Messenger", "Integration", "David Marcus", "PayPal CEO", "Facebook Payments", "Product Launch", "Influential Endorsement" ], "lesson": "High-profile endorsements amplify impact. David Marcus (former PayPal CEO) sharing Brandon's Messenger integration post elevated both the product launch and Brandon's internal credibility.", "topic_id": "topic_8", "line_start": 245, "line_end": 249 }, { "id": "ex26", "explicit_text": "And then that blew up and all of a sudden, the CPO of Shopify, Craig or whatever, now starts thinking I'm legit even though... Because someone of his caliber was also sharing these things, about a product that we built and whatnot.", "inferred_identity": "Craig Miller (Shopify CPO) validation through external endorsement", "confidence": "explicit", "tags": [ "Shopify", "Craig Miller", "CPO", "External Validation", "Peer Credibility", "Organizational Influence", "Internal Status Shift" ], "lesson": "Peer validation cascades into leadership perception. External endorsement from respected figures changes how organizational leaders perceive contributors.", "topic_id": "topic_8", "line_start": 248, "line_end": 249 }, { "id": "ex27", "explicit_text": "It accelerated my career probably a decade.", "inferred_identity": "Brandon Chu's career acceleration through writing", "confidence": "explicit", "tags": [ "Brandon Chu", "Writing", "Career Acceleration", "ROI", "Leadership Track", "VP of Product", "40 Hour Posts" ], "lesson": "Writing ROI compounds over time. 40-hour posts distributed over years accumulated a decade of career acceleration for Brandon.", "topic_id": "topic_8", "line_start": 254, "line_end": 254 }, { "id": "ex28", "explicit_text": "It had gained so much traction and I had become an exec now at Shopify and I was so busy at them. I was like, 'I don't have the time to make this thing as good as it was. And I'm not even going to put another post out because I don't want to disappoint people.'", "inferred_identity": "Brandon Chu's writing halt", "confidence": "explicit", "tags": [ "Brandon Chu", "Writing", "Perfectionism", "Executive Role", "Time Scarcity", "High Expectations", "Reputation Risk", "Three Year Hiatus" ], "lesson": "Success creates perfectionism traps. Brandon stopped writing in 2018 because he feared disappointing readers with lower-quality work—the popularity of earlier posts made continuation feel impossible.", "topic_id": "topic_7", "line_start": 259, "line_end": 261 }, { "id": "ex29", "explicit_text": "For all other decisions, you should just literally just go with whatever your gut is or delegate it because you're only human and your gut is going to be right a decent amount of time too. And so just make those fast so that you can keep the team velocity high.", "inferred_identity": "Brandon Chu's decision-making post framework", "confidence": "implicit", "tags": [ "Brandon Chu", "Writing", "Decision Making", "Prioritization", "Delegation", "Gut Instinct", "Team Velocity", "Most Popular Post" ], "lesson": "Trivial decisions should be gut-called to preserve team momentum. Distinguishing critical from trivial decisions is the PM superpower.", "topic_id": "topic_9", "line_start": 269, "line_end": 270 }, { "id": "ex30", "explicit_text": "Once you've had a few battle scars of things that you thought were going to ruin everything, your career, your reputation, blah, blah, blah, and then actually nothing happened, you just start to raise the bar about what's actually important.", "inferred_identity": "Brandon Chu's decision recalibration principle", "confidence": "implicit", "tags": [ "Brandon Chu", "Decision Making", "Experience", "Resilience", "Battle Scars", "Risk Recalibration", "Confidence Building" ], "lesson": "Experience teaches risk calibration. After several career-threatening decisions that had no negative impact, PMs naturally raise their bar for what constitutes true importance.", "topic_id": "topic_9", "line_start": 281, "line_end": 282 }, { "id": "ex31", "explicit_text": "The one that always I'd say has overall had the most traction or just constantly, even to today, people still tweet about or message me, whatever, was the one about making good decisions as a PM.", "inferred_identity": "Brandon Chu's decision-making post enduring impact", "confidence": "explicit", "tags": [ "Brandon Chu", "Writing", "Decision Making", "Most Popular", "Ongoing Traction", "Evergreen Content", "PM Skills" ], "lesson": "Evergreen PM frameworks retain value indefinitely. Brandon's decision-making post maintains relevance and daily impact years after publication.", "topic_id": "topic_9", "line_start": 265, "line_end": 267 }, { "id": "ex32", "explicit_text": "I've been wanting to write literally for three years. It'll probably be really long, but just a huge post about being a platform PM as opposed to product PM.", "inferred_identity": "Brandon Chu's unwritten platform PM post", "confidence": "explicit", "tags": [ "Brandon Chu", "Writing", "Platform PM", "Product Management", "Unwritten", "Future Content", "Three Year Delay" ], "lesson": "Perfectionism prevents shipping. Despite wanting to write about platform PM for three years, Brandon hasn't shipped due to desire for comprehensive coverage.", "topic_id": "topic_10", "line_start": 286, "line_end": 288 }, { "id": "ex33", "explicit_text": "The developers building these apps that are going to be consumed by these businesses, these merchants, and these apps also may be presented to end buyers. There's now three constituents and there's all these crazy things around policy, data sharing, just tension between which side gets economically rewarded for doing what.", "inferred_identity": "Platform ecosystem complexity", "confidence": "implicit", "tags": [ "Platform PM", "Multi-stakeholder", "Developers", "Merchants", "End Users", "Policy Complexity", "Economic Alignment" ], "lesson": "Platform PMs manage multiple constituencies with conflicting incentives. Developers, merchants, and end buyers have competing interests requiring explicit principle-based trade-offs.", "topic_id": "topic_10", "line_start": 287, "line_end": 289 }, { "id": "ex34", "explicit_text": "When you long press on an app on your iPhone and it has a shortcut list of things you could do quicker. Right? Okay. Say if you long press your email app, it'll probably say create new email as one of them. That's an extension. That's iOS saying, 'Hey, Gmail app. I'm going to give you the ability to actually deep link this experience into your app through our operating system.'", "inferred_identity": "iOS shortcuts architecture example", "confidence": "explicit", "tags": [ "iOS", "Shortcuts", "Deep Linking", "Platform Design", "Third-party Integration", "User Experience", "Extensions", "Apple Example" ], "lesson": "Platform design involves fundamental architectural decisions about third-party access. iOS shortcuts demonstrate how platforms can grant powerful capabilities while maintaining control.", "topic_id": "topic_10", "line_start": 295, "line_end": 296 }, { "id": "ex35", "explicit_text": "There's so many crazy decisions there about, well, if you go too far, you give Google too much control there and they could do some really messed up stuff. Or if you don't go far enough, then it's really just lame.", "inferred_identity": "Platform design trade-offs", "confidence": "implicit", "tags": [ "Platform Design", "Power Dynamics", "Third-party Control", "User Experience", "Feature Depth", "Platform Tension", "Design Trade-offs" ], "lesson": "Platform design exists in tension between empowering third-parties and protecting first-party interests. Too much control lames the ecosystem; too little power enables abuse.", "topic_id": "topic_10", "line_start": 296, "line_end": 297 }, { "id": "ex36", "explicit_text": "The cycles for platform work are five to 10 odd times longer. You're maybe changing something on the infrastructure level, then opening up an API and then doing an alpha period for the API where developers now build on that and test things. And then you move into a beta. And then finally, two years later, some end customer actually uses that app.", "inferred_identity": "Platform PM feedback cycle length", "confidence": "implicit", "tags": [ "Platform PM", "Long Cycles", "5-10x Longer", "API Alpha", "Beta Period", "Two Year Timeline", "Infrastructure Changes" ], "lesson": "Platform product cycles are 5-10x longer than consumer product. Feedback from actual end users takes two years, requiring psychological preparation.", "topic_id": "topic_11", "line_start": 308, "line_end": 309 }, { "id": "ex37", "explicit_text": "In Amazon's platform, I'm making this up, but I assume that a pretty big important intro principle is that if there's ever a toss up between deciding between the seller and the buyer, the consumer, we're going to decide with the consumer. Right?", "inferred_identity": "Amazon platform principle", "confidence": "implicit", "tags": [ "Amazon", "Platform Strategy", "Consumer Focus", "Seller Trade-off", "Principle-based Decision", "Constituent Priority" ], "lesson": "Amazon's platform principle prioritizes consumer over seller, accepting seller dissatisfaction as acceptable trade-off. This principle cascades through all policy and design decisions.", "topic_id": "topic_11", "line_start": 311, "line_end": 312 }, { "id": "ex38", "explicit_text": "That's why every time you refund something on Amazon, anytime you got a complaint, send you another one. Right? They made that trade off to be a consumer focused platform and obviously, that's been amazing for them, but you also hear the contrasting stories of sellers that are really pissed off Amazon that have ruined their businesses and whatnot.", "inferred_identity": "Amazon consumer-first refund policy", "confidence": "explicit", "tags": [ "Amazon", "Refund Policy", "Consumer Protection", "Seller Risk", "Second-order Effects", "Business Destruction", "Trade-off Cost" ], "lesson": "Consumer-focused platforms create seller externalities. Amazon's generous refund policy protects consumers but destroys small seller businesses—a conscious trade-off.", "topic_id": "topic_11", "line_start": 313, "line_end": 314 }, { "id": "ex39", "explicit_text": "In Shopify's case, we are here to support entrepreneurs and businesses in making their dreams come true and creating independence. And that is sometimes at the cost of developers on our platform.", "inferred_identity": "Shopify merchant-first principle", "confidence": "explicit", "tags": [ "Shopify", "Platform Principle", "Merchant Focus", "Entrepreneur Support", "Developer Trade-off", "Independence", "Constituent Priority" ], "lesson": "Shopify's platform principle prioritizes merchants over developers, inverse to Amazon's consumer priority. This informs all ecosystem policy and feature decisions.", "topic_id": "topic_11", "line_start": 314, "line_end": 315 }, { "id": "ex40", "explicit_text": "Sometimes we may make a data policy change saying, 'Hey. It's more important that the merchant has access to this data across apps. And it's important that actually you push that data back in Shopify so that you don't hold that data back so that this other app can't use it.' And now we're sending the same end customer two marketing texts when they've already opted out of marketing texts or something like that.", "inferred_identity": "Shopify data sharing policy example", "confidence": "implicit", "tags": [ "Shopify", "Data Policy", "Merchant Access", "Developer Constraint", "Data Sharing", "Second-order Effects", "Customer Experience Cost" ], "lesson": "Merchant-first data policies force developers to share customer data, creating second-order effects like duplicate marketing messages. Trade-off visibility prevents launch-day CEO vetoes.", "topic_id": "topic_11", "line_start": 314, "line_end": 318 }, { "id": "ex41", "explicit_text": "If you create a UI kit or something like that, you're going to see the good and the bad that comes out of that UI kit being given to the third party ecosystem and you'll learn about consumer.", "inferred_identity": "Platform PM consumer learning", "confidence": "implicit", "tags": [ "Platform PM", "UI Kit", "Third-party Ecosystem", "Learning", "Consumer Impact", "Ecosystem Dynamics" ], "lesson": "Platform PMs observe consumer impact across diverse third-party implementations. UI kit ecosystems reveal both best practices and poor implementations.", "topic_id": "topic_12", "line_start": 324, "line_end": 327 }, { "id": "ex42", "explicit_text": "I'd say overall, based on most PMs that I've met, I'd say, look, it is hard to do when you are a PM somewhere, but do a legitimate side hustle, found a company on the side and learn everything else. Because I think sometimes you're in this silo of your feature, your area or whatnot. And you forget what it means to sell something to a customer, what it means to support a product, what it means to ship something and get destroyed because it doesn't even work or something like that.", "inferred_identity": "Brandon Chu's top PM development advice", "confidence": "explicit", "tags": [ "Brandon Chu", "Side Hustle", "Startup Founding", "Full Business Cycle", "Sales", "Support", "PM Development", "Founder Experience" ], "lesson": "Side projects teach complete business skills beyond product. PMs siloed in features forget sales, support, and shipping—founder experience bridges this gap.", "topic_id": "topic_13", "line_start": 331, "line_end": 333 }, { "id": "ex43", "explicit_text": "I love telling people that literally don't even know what HTML is or something like that, which I was one of those people that from right now over the weekend, you could build a clone of Twitter using a tutorial on Rails or something like that. You can do it. You may not know everything that's actually happening, right? But you could actually get that deployed and it'll work and it'll blow your mind that you did that.", "inferred_identity": "Brandon Chu on non-technical PM learning", "confidence": "explicit", "tags": [ "Brandon Chu", "Non-technical PM", "Rails Tutorial", "Twitter Clone", "Weekend Project", "Technical Learning", "Demystification", "Low Barrier" ], "lesson": "Non-technical PMs can build deployed products in a weekend. Rails tutorials enable any PM to ship, breaking through technical intimidation and building confidence.", "topic_id": "topic_13", "line_start": 335, "line_end": 336 } ] }