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20VC: Lessons from Mark Zuckerberg, Keith Rabois & Tobi Lütke | Why Remote is a Bad Idea for 90% of Companies | The Framework for How Shopify Builds Product Today | What Humans Get Wrong About Marriage and Kids with Kaz Nejatian, COO @ Shopify

20VC · Harry Stebbings — Kaz Nejatian · August 14, 2024 · Original

Most important take away

The job of a PM is to build the right thing, the right way, at the right time — and most companies wildly underestimate the “how” and “when” in favor of debating “what.” Ship complete products with a clear vision rather than half-baked MVPs that train users to expect bad software, and hire learners over experience-collectors when you’re a growth-stage software company.

Summary

Actionable insights and career advice for product leaders, engineers, and operators:

Product philosophy and building

  • Build the right thing, the right way, at the right time. Most companies only care about the “what.” The bigger leverage is in the “how” (where in the stack you build it) and the “when.”
  • Ship complete V1s with a real vision, not half-products to “see what happens.” Lean Startup has been widely misread — users don’t want to be tested on. A constrained V1 of a clear vision is fine; a visionless ship-and-see is not.
  • Software is more like woodwork than science experiments — a three-legged chair is not a viable test.
  • Quality bar over speed when you’re optimizing for decades, not quarters. Shopify intentionally over-builds because they’re thinking on a 100-year horizon. Discount factor on time determines whether this is wasteful.
  • Have a “no party tricks” rule: don’t demo features that only work in narrow conditions. If you show it, it should generally work.

Tools, internal infrastructure, and tech patterns

  • Tools shape their builders. Shopify builds its own internal tooling (HR, payroll, headcount planning, GSD project management) because no off-the-shelf software shares their opinions about how a company should be run.
  • Excel has done more damage than most software because it creates false certainty (no column for confidence level). Replace static planning artifacts with continuously-running internal software tied to your data APIs.
  • Stripe + Shopify is held up as possibly the most value-creating software partnership in history — partner deeply where opinions align, build internally where they don’t.
  • Marketers at Shopify write code and edit landing pages in GitHub; many salespeople write SQL. The hiring filter selects for people who want to learn these things, not for people who already know them.

Career advice for PMs and engineers

  • PMs don’t need to write code, but every PM must understand how code is written. Argue about where in the stack to build, not just what to build.
  • For a product leader starting a new role: optimize your first few years for shipping as many things as possible, not for career progression — collect at-bats.
  • PMs should blame themselves for everything. If the user isn’t better off, only one person could have made the mistake.
  • Replace “10 years of experience” requirements with the ability to learn from scratch — unless you’re explicitly running an experience-based business (which is a valid model, just not a growth-software model).
  • Industry-switching hires (e.g., marketers or finance people coming into software from outside) generally don’t work. Hiring from Meta tends to work — it’s an exceptional training program.

Risk, vision, and leadership patterns

  • From Keith Rabois and Max Levchin: be perpetually hungry; kind but aggressive in execution.
  • From Tobi Lütke: three priorities only — (1) build great products, (2) make money, (3) never reverse 1 and 2. Hard to hold as a public company, but it works.
  • From Mark Zuckerberg: judge risk-taking by the process, not the outcome. Newsfeed, the Like button, and AR/VR were all massive product re-bets most founders wouldn’t dare make.
  • Meta has produced more $100M+ founders than any other tech company combined — its operator training is unmatched. Meta’s only real mistake was not publicly celebrating itself, which let a false narrative spread.

Remote work

  • Remote is a bad idea for ~90% of companies. It only works at Shopify because they’ve invested massively in tools, systems, and teams dedicated to making it work. Without that infrastructure, going remote will fail.
  • When Shopify went remote, the first 6–12 months broke things badly. They burned the bridges deliberately (gave up leases, hired far from offices) so they couldn’t retreat.

Information flow and culture

  • Default to public sharing of information. Kaz’s biggest career mistakes have all had the same shape: information traveling up the org chart instead of flowing dynamically. It’s okay for your boss to learn about something at the same time as the rest of the company.
  • Values should be things a reasonable person could argue against. “Integrity” is a non-value; “thrive on change” and “learner’s mindset” are real values because some companies legitimately don’t want them.
  • Disagreement is normal and healthy — Kaz’s most-used phrase to Tobi is “I disagree.” The goal is finding truth together.

Personal: marriage and life

  • Three entities to maintain in a marriage: you, your spouse, and the marriage itself. Date nights weekly even with four young kids.
  • Don’t model your life on people worth $100B — their circumstances aren’t yours.
  • For men: finishing high school, getting job experience, then marrying (in that order) is one of the strongest predictors of health, wealth, and happiness; bankruptcy rates drop, cancer survival rates rise.

Quick-fire takeaways

  • Most-impressive recent strategies: Microsoft/OpenAI on search, ExxonMobil (~160% profit growth in a “boring” industry), Canva, and Figma (which kept shipping through the failed Adobe acquisition rather than checking out).
  • Follow politics weekly, not daily — daily turns it into a horse race.

Chapter Summaries

  1. Lessons from Keith Rabois and Max Levchin — both are uncommonly aggressive and perpetually hungry; founders should match that ambition.
  2. Vision vs. iteration — Kaz argues Lean Startup has been broadly misapplied; ship complete V1s with a clear vision, not half-baked tests on real users.
  3. Lessons from Tobi Lütke — Shopify’s three priorities (build product, make money, never reverse them) and its over-built quality bar driven by a 100-year horizon.
  4. Internal tooling — why Shopify builds its own HR, headcount, project management, and culture tools, and why Excel and CSV-glued workflows produce bad decisions.
  5. Learner’s mindset and hiring — replacing 10-years-experience filters with the ability to learn; making it harder, not easier, to apply to Shopify; expecting marketers to use GitHub and salespeople to write SQL.
  6. Lessons from Mark Zuckerberg — risk judged by process not outcome; Meta’s underappreciated bets (Newsfeed, AR/VR, Ray-Ban glasses); Meta’s mistake of not telling its own story; Meta’s unmatched founder-pipeline.
  7. The PM job at Shopify — build the right thing, the right way, at the right time; PMs blame themselves; PMs must understand code even if they don’t write it.
  8. Talk and meetings — meetings are expensive; Shopify puts the cost of each meeting in its invite; prefer written artifacts and code, which also become training data for LLMs.
  9. Remote work — bad idea for ~90% of companies; Shopify only makes it work because of dedicated tools, teams, and burning the bridges back to offices.
  10. Thriving on change and modeling Shopify — analysts struggle because Shopify is more like a portfolio/operating system than a SaaS point solution.
  11. Enterprise without becoming “enterprise software” — Shopify added enterprise customers by stopping saying no, not by building bespoke enterprise software; no “if enterprise” branches in the codebase.
  12. Partnerships and Stripe — building for 100 years means partnering with companies whose opinions align (Stripe, Affirm, Meta, Google, Apple) and refusing zero-sum adjacency fights.
  13. Information flow and values — default to public sharing; values must be things a reasonable person could argue against.
  14. Marriage, family, and life advice — care for three entities (you, spouse, marriage); marriage is a major positive-life predictor for men; don’t model your life on billionaires.
  15. Quick-fire round — best hires come from Meta; optimize first PM years for shipping at-bats; most impressive recent execution: Microsoft/OpenAI, ExxonMobil, Canva, Figma.