ACQ2 by Acquired: How to Live in Everyone Else's Future

Guest: Tobi Lütke, CEO & Founder of Shopify

Released: September 18, 2025

Hosts: Ben Gilbert & David Rosenthal

Overview

In this episode, Ben and David sit down with Shopify's founder and CEO, Tobi Lütke, for a wide-ranging and philosophical discussion. Rather than a standard retrospective on Shopify’s meteoric growth, the conversation dives deep into the shifting landscape of technology, the realities of operating in a world transformed by AI, and the responsibilities—and opportunities—facing leaders and creators during a platform shift. Tobi reflects on lessons as a CEO through Shopify’s highs, meme-stock era, and completion of "another platform shift" into AI-powered commerce. The episode is sprinkled with practical insight, wisdom on leadership and company-building, and memorable moments on living in the “relative future”—all delivered in Tobi’s distinctive, candid voice.

Major Themes & Insights

1. Living in Everyone Else’s Future

• Tobi’s mindset is to always operate one step ahead, adopting betas and new tools before they’re mainstream.

  “You don’t even need to predict the future that well. If you just live in everyone else’s relative future… it’s not that hard.”
  — Tobi Lütke [07:18]

• Philosophy of experiencing upcoming changes first-hand to guide company decisions, especially in product.

  “My biggest job I personally can do for the company and then my company can do for my customers, which is live in everyone else’s relative future.”
  — Tobi Lütke [06:58]

2. The AI Platform Shift

• Awe at rapidly shifting capabilities of AI, analogy to previous major computing platform shifts.

  “It is a privilege of a lifetime to be part of another platform shift… It’s remarkable how quickly one normalizes to completely futuristic new things.”
  — Tobi Lütke [01:23]

• Tobi’s “Tobi Eval” approach—personal batch testing and evaluation of new AI models.

  “I have a Tobi Eval—it’s literally a folder of prompts with expected and judged results. I run it against every model at some point.”
  — Tobi Lütke [02:34]

• Reflection: The world has already blown past the Turing Test.

  “No sci-fi author dared to predict is that the Turing Test just passes by… and nobody noticed.”
  — Tobi Lütke [20:23]

3. The Philosophy & Mechanics of Abstraction

• The importance—and risks—of abstraction in software and platform design.

  “Abstraction is just another word for pretension… Abstractions can also lower the ceiling of what’s possible.”
  — Tobi Lütke [08:56]

• Explains the idea that good abstractions raise the “floor,” but great ones do so without lowering the “ceiling”—the upper bounds of what’s possible.

  “What you are trying to do as a toolmaker… make a tool that brings the floor up significantly but doesn’t constrain the ceiling. And that is extremely hard.”
  — Tobi Lütke [12:57]

4. Human Agency & AI in Product Development

• AI as a democratizer: letting more users reach the top of their ambitions, not just experts.

  “I want people, if they have whatever their vision is unencumbered, is a 10 out of 10 on this scale. I want them to hit it… computers should never constrain people.”
  — Tobi Lütke [15:07]

• Showcases practical impact: Shopify merchants using AI to reimagine product photos, increasing business in ways previously impossible.

  “They just changed images of all their products from Malibu beach houses to Parisian apartments—sales tripled… Now, it’s about the most boring thing you can imagine. That’s how much the world has changed.”
  — Tobi Lütke [17:10]

5. Adaptation, Problem-Solving, and AI Literacy

• The new baseline: AI-assisted work will become the minimum expectation.

  “Even five years from now, people who are successful… will be the people who best know how to use these tools.”
  — Ben Gilbert [41:09]

• Tobi instituted a company-wide policy at Shopify: reflexively reach for AI first.

  “We set the expectation that we require people reflexively reach for AI now. Because the people who do are otherwise going to be people who sequester all the best careers to themselves.”
  — Tobi Lütke [43:41]

• Context engineering as the new essential skill in the AI era.

  “The fundamental skill of using AI well is to be able to state a problem with enough context in such a way that… the task is plausibly solvable.”
  — Tobi Lütke [46:02]

6. Data, Process, and Continuous Improvement

• Tobi keeps a digital archive of his daily activity—a 15-year personal digital “black box.”

  “I have… a screenshot of my machine every ten minutes… for going on 15 years now.”
  — Tobi Lütke [53:13]

• Uses AI to mine the archive, track belief changes, and improve self-awareness.

7. Leadership, Organization Design, and Founder-Led Companies

• Clear distinctions between founder-led and managerial companies.

  “Founder-run companies… are just so different from more managerially run companies, more traditional companies. They’re just completely crap in so many ways.”
  — Tobi Lütke [82:59]

• Consensus vs. Leadership:

  “Every time consensus makes a decision, it’s the absence of leadership… consensus is always the absence of leadership.”
  — Tobi Lütke [94:02]

• Leading by fiat or single vision is essential for outlier, 10/10 outcomes. Consensus delivers mediocre results.

  “If you’re a company that wants to hit 8, 9, 10 or die trying, then you kind of have to rule by fiat.”
  — Tobi Lütke [98:12]

• Believes some non-founder CEOs have refounded their companies, e.g. Satya Nadella at Microsoft, Jamie Dimon at JPMorgan.

8. Personal Evolution: Changing Beliefs Over Time

• Tobi admits to having done a 180 on the importance of leadership.

  “I didn’t believe in leadership. I just didn’t think leadership was important. … I believe those things are utterly incorrect now. I think people love leadership. They love complaining about it too, which they should.”
  — Tobi Lütke [60:25]

• Lessons on delegation and creating 'dream jobs' for others.

  “Everything I don’t like is someone else’s dream job. And that’s like incredibly liberating.”
  — Tobi Lütke [62:39]

• Applies analogies from music and jazz bands to leadership and organization.

9. Platform Companies, Economic Impact, and Regret Minimization

• On Shopify’s impact and responsibility:

  “If you subtract Shopify out, if it disappears overnight, there’s a lot of countries which would have no GDP growth.”
  — Tobi Lütke [102:45]

• On judging CEOs:

  “The way to judge a CEO is out of what opportunity did you carve what company and maybe even for what reasons.”
  — Tobi Lütke [103:49] “My biggest regret would just be… I didn’t take it seriously. Responsibility seriously enough.”
  — Tobi Lütke [103:51]

• Tobi’s regret minimization principle:

  “At the end of life, you get the… game over screen is you get to meet the person you could have become… Your goal is to minimize the difference between that and your potential.”
  — Tobi Lütke [107:18]

Notable Quotes & Memorable Moments

• On leadership and consensus:

  “Consensus is always the absence of leadership. … Some people are so clever they can manufacture consensus around what they would have chosen anyway and operate this way. But that’s the only time these things combine.”
  — Tobi Lütke [94:02]

• On the overlooked arrival of powerful AI:

  “No sci-fi author dared to predict… that the Turing Test just passes by… and nobody noticed.”
  — Tobi Lütke [20:23]

• On personal and company resilience:

  “Everything I don’t like is someone else’s dream job. … Since then I’ve been creating lots of beautiful dream jobs of stuff that I don’t want to do.”
  — Tobi Lütke [62:39]

• On founder-led public companies:

  “People underestimate how expensive hedging is. … All this to say, so we’ve come here to talk about founder-led companies… people don’t understand how stratospherically different they are.”
  — Tobi Lütke [89:11]

• On the privilege and awe of technological progress:

  “We are living in the golden age of humanity right now. … People a thousand years from now will study these times… because it’s where we figured ourselves out.”
  — Tobi Lütke [24:15]

Important Timestamps & Sections

| Timestamp | Segment / Topic | |------------|------------------------------------------------------------| | 01:23 | Living through a platform shift: AI as transformative | | 02:34 | Tobi’s personal “eval” process for testing AI models | | 07:18 | Living in the relative future by using betas/early tech | | 12:57 | Raising the “floor” without lowering the “ceiling” | | 15:07 | Ensuring platforms don’t constrain user creativity | | 17:10 | Real-world AI impact: product imagery & sales growth | | 20:23 | The unnoticed passing of the Turing Test | | 41:09 | Why AI literacy is now the baseline for success | | 43:41 | Shopify’s “mandatory AI” policy | | 53:13 | 15-year personal digital life archive | | 60:25 | Changed mindset about leadership and organization | | 82:59 | Difference: founder-led vs. managerial organizations | | 94:02 | Leadership & consensus as opposites | | 98:12 | Extreme outliers need visionary, not consensus-driven, teams| | 102:45 | Shopify’s GDP-scale impact; responsibility of leadership | | 107:18 | Tobi’s regret minimization and “meeting your future self” |

Host Reflections & Conversation Highlights

• The hosts frequently marvel at Tobi’s candidness and unique way of “living in the future,” as well as his willingness to openly discuss both abstract philosophy and nitty-gritty management tactics.
• Amusing moments occur as Tobi reveals his unshakeable urge to always update to beta software, even if it breaks his only phone as a public company CEO [05:50].
• Seminal quote reference: “A museum of other people’s passion projects, as John Collison puts it”—called out as possibly the best tweet ever [26:18].
• The jazz band metaphor for team leadership and company building is a highlight.
• Tobi’s (somewhat shocking) personal digital black box—a screenshot every 10 minutes for 15 years—astonishes the hosts [53:13].
• Open, clear-eyed discussion of what the meme-stock era, valuation swings, and leadership transitions meant inside Shopify.

Actionable Takeaways

• For individuals: Embrace new technology early, develop “context engineering” skills, and avoid calcifying around solutions rather than problems.
• For organizations: Build platforms and tools that raise the floor for everyone, but don’t unnecessarily lower the ceiling for your most ambitious users.
• For leaders: Founder-led and “refounded” companies can uniquely pivot and build for the future—managerial consensus is the enemy of 10-out-of-10 outcomes.
• For everyone: Judge yourself not just on current regret minimization, but by closing the gap between your present and best possible self.

Suggested Episode Use

Whether you’re a founder, product leader, tech enthusiast, or anyone navigating the AI era, this episode offers a mix of philosophical framing and practical frameworks. Tobi’s authentic perspective lifts the curtain on what it means to lead—and build—at the front edge of a world in rapid flux.

For full context and inspiration, this episode is essential listening for anyone crafting the future, today.