Annotations (26)
“Doug Leone told us that after the dot-com crash, every other venture firm was taking Mulligan funds. They went to their LPs and said, there's nothing we can do on this one. We're going to be more disciplined next time. Sequoia said, absolutely not. We will never lose money for our investors ever. He said the best line anyone's ever said on Acquired: we looked at each other and you could burn cigarettes on our arms, and we wouldn't flinch.”— Doug Leone
Leadership & Management · Business & Entrepreneurship · Strategy & Decision Making
DUR_ENDURING
Burn cigarettes on our arms metaphor
“End of 2022, FTX happens. Interest rates go up, all the podcast advertising market falls off a cliff. Our revenue dropped 40%. That was the moment when we changed everything. Ben and I looked at each other and it wasn't even really a conversation. We just knew what we had to do. We need to get to work. We need to focus on only what is enduring, make great work, and stop doing everything else.”— David Rosenthal and Ben Gilbert
Strategy & Decision Making · Leadership & Management · Business & Entrepreneurship
DUR_ENDURING
Revenue drop forced quality focus
“In calling out Hermes, I think quality and scarcity have become an important part of Acquired. We used to feel like we were bad at podcasting because we couldn't make very many, because we didn't have a whole production team. At some point, we looked at each other and we're like, maybe if we just admit that we are heavily constrained and then try to just lean into that constraint in the way that Hermes leans into every single Birkin bag must be handmade by one artisan, we're going to build a bus...”— Ben Gilbert
Strategy & Decision Making · Business & Entrepreneurship · Operations & Execution
DUR_ENDURING
Constraint became competitive advantage
“I've been toying with this idea of stored potential energy that great businesses have a stored potential energy that you can't see in the current financials. Great people have that too. They have these reserves that come out when they need them. I think we're trying to store up as much potential energy in Acquired as we can rather than anytime there's a way to make it show up on the financial statements.”— Ben Gilbert and Michael Lewis
Strategy & Decision Making · Business & Entrepreneurship · Philosophy & Reasoning
DUR_ENDURING
Store energy vs. release it for revenue
“Language is a lossy compression of thought. When you and I are communicating, I had a thought. I compressed it into a very narrow bandwidth thing of speech. I told it to you, you uncompressed it into your brain. It might actually mean a pretty different thing to you than it means to me. That insight is at the bottom of my creative process. I assume when I write a book that what goes into people is something different that came out of me.”— Ben Gilbert and Michael Lewis
Philosophy & Reasoning · Creativity & Innovation · Psychology & Behavior
DUR_ENDURING
Communication is lossy compression
“The feeling I get is this person is bringing out a better version of me. Danny Kahneman always felt at risk of being dismissed, thought the lesser partner. There was a status difference between the two of them. Everyone in the world thought Amos was the smartest person they'd ever met. You two didn't have that. Ever have any of that? Not for me. The number of fights we've had or real tension we've had is two or three ever in 10 years.”— Michael Lewis, David Rosenthal, Ben Gilbert
Psychology & Behavior · Leadership & Management
DUR_ENDURING
Absence of status competition enables partnership
“We had an existential crisis. Are we being wussies? We're not doing Hollywood. We're not adding more shows. We're not building an enterprise. We sought advice from one of the best investors ever. He sat there and thought a minute. He said, I've seen so many founders become trapped in prisons of their own making in their own companies. You guys have avoided that fate. Don't go down that road.”— Anonymous investor
Leadership & Management · Strategy & Decision Making · Psychology & Behavior
DUR_ENDURING
Success can create self-made prisons
“With the NFL, because the product is scarce, and then they have very smartly cultivated that and engineered it to be more scarce, more of an event driven sport, that's made all the difference. For the last three years, we've released 12 episodes. Next year we're going to do eight episodes for the whole year. Most of these things actually are confirmation bias. We get some inkling that we should continue to go in this direction.”— David Rosenthal and Ben Gilbert
Strategy & Decision Making · Business & Entrepreneurship · Economics & Markets
DUR_ENDURING
Scarcity engineering drives event perception
“Most podcasts, your dream is to create a habit. We've thrown that out the window and said we need to create events. It needs to be the current thing when we release an episode. Once a year, we have to have a Super Bowl. Doing the Chase Center show, very small amount of people in the audience relative to the number of people who listen to our episodes, it's 0.4% of the audience.”— Ben Gilbert
Business & Entrepreneurship · Strategy & Decision Making · Culture & Society
DUR_ENDURING
Small live event creates massive brand impact
“We want to create a durable business on our side and a great listener experience on the listener side. I always feel, as a listener, so disrespected when there is this content of the podcast that is diamond quality, and then they're running McDonald's ads in the middle. The very first ad we ever sold, we said, what sponsor could we get that would make people perceive Acquired to be a higher quality brand so we could have our cake and eat it too?”— Ben Gilbert
Strategy & Decision Making · Business & Entrepreneurship · Psychology & Behavior
DUR_ENDURING
Sponsors strengthen rather than dilute brand
“I am terrified of betraying that trust. Anytime we make an episode, I think of it as a churn opportunity. If we put this in the feed, if we don't live up to the expectations that our listeners have, we will burn them and they will leave us forever. Are we letting people down? Why does Acquired framework, there's a strong element of terror of why it works. We're constantly terrified every time we make an episode.”— Ben Gilbert and David Rosenthal
Psychology & Behavior · Leadership & Management · Business & Entrepreneurship
DUR_ENDURING
Terror maintains quality standards
“In the media business, in podcasting, you can grow your audience, and thus your revenue, and thus your importance in the world. All outputs can scale completely independently of your inputs. David and I effectively do the same thing that we did not 10 years ago, but two years ago to make an episode. The audience has grown so much that every output from the business is dramatically different, even though all the inputs are the same.”— Ben Gilbert
Business & Entrepreneurship · Economics & Markets · Operations & Execution
DUR_ENDURING
Outputs scale independently of inputs
“The internet niches are way bigger than you think they are. If you think you're writing about a niche topic, the internet being a global community of four-ish billion people, means that any little niche, there might be six people in your geography that care about it in your local town, but there are millions of people online. The internet is your way to reach them. No matter how niche you are, it's actually way, way bigger.”— Ben Gilbert
Economics & Markets · Technology & Engineering · Business & Entrepreneurship
DUR_ENDURING
Global reach transforms niche economics
“Every time, if you were to take time off to go do something in Hollywood, you'd be abandoning this glorious network. The opportunity cost is so high of spending a month not making an Acquired episode because when we publish an episode of Acquired, the base does come with us. Podcasts are unique in that it does have that true subscriber base. Unlike anything else where you click subscribe, there's not an algorithmic platform that disintermediates you.”— Ben Gilbert
Business & Entrepreneurship · Technology & Engineering · Economics & Markets
DUR_CONTEXTUAL
Podcasts avoid algorithmic disintermediation
“You're added risk. You're taking risks when you don't know what's going to happen when you come on. You know how your heart sinks when someone gets up at a podium with a speech and they're going to read their speech? The audience is waiting for you to get through this thing because they know nothing's going to happen. If you get up and you just start talking, the audience also knows, oh, my God, this could be a disaster. They don't know where it's going.”— Michael Lewis
Creativity & Innovation · Psychology & Behavior
DUR_ENDURING
Risk creates audience engagement
“If you were going to ask me how you were going to fail, that's exactly the thing I would say. You'd run out of gas or run out of material that made your socks go up and down. Okay, listeners, now is a great time to thank one of our very favorite partners. The reasons Acquired will eventually fail, I don't think come from platform disruption.”— Michael Lewis and Ben Gilbert
Creativity & Innovation · Psychology & Behavior
DUR_ENDURING
Creative death from curiosity exhaustion
“At what point do you decide that, oh, there's an odd chemistry here? We really just wanted to spend more time together. We like to say that we each have two spouses. We have our actual romantic spouses that we have families with, and then we have each other. David and I shared a bank account before my wife and I shared a bank account.”— Ben Gilbert and David Rosenthal
Leadership & Management · Business & Entrepreneurship · Psychology & Behavior
DUR_ENDURING
Partnership commitment before marriage commitment
“We had to add this thing called a production meeting. About six months ago, one week before recording, we are required to get together and agree on an episode structure but not share any details. We got so into this improvisation thing that some of our episodes would end and you're like, that had no flow to it. You guys had two completely different ideas for the episode.”— Ben Gilbert
Operations & Execution · Creativity & Innovation
DUR_ENDURING
Structure enables better improvisation
“Warren Buffett is tracking who is coming in and out of the A shares and thinking about it. He has that whole thing about don't put your money in an index fund, put your money in a big bundle of stocks. Put it in a few stocks and watch those stocks like a hawk. They watch that thing. In history, has anybody ever done anything like that?”— Michael Lewis
Leadership & Management · Business & Entrepreneurship
DUR_ENDURING
Buffett tracks individual A share transactions
“One of the ways that we aired was trying to exit the integrated circuit market or diversify from that market. The key insight from Morris Chang was you are already in the best business. Integrated circuits are the future and will be for a long time, and you're already the best at them, so stop trying to do other things and just do that really well. Probably to a fault and with a bias, we believe that about Acquired every time we look at anything else.”— Morris Chang via Ben Gilbert
Strategy & Decision Making · Business & Entrepreneurship
DUR_ENDURING
Already in best business, stop diversifying
Frameworks (4)
Scarcity Engineering for Value Creation
How to deliberately create scarcity to increase perceived value
A framework for converting operational constraints into strategic advantages by engineering scarcity rather than fighting it. Based on NFL's approach to event-driven content and Hermes's approach to handcrafted luxury. Core insight: scarcity can be cultivated and becomes a moat when it's authentic to the production process.
Components
- Acknowledge Your True Constraint
- Convert Constraint to Quality Signal
- Engineer the Cadence
- Build Anticipation Systems
Prerequisites
- Clear understanding of core constraint
- Strong product quality
- Audience trust
Success Indicators
- Increased anticipation metrics
- Higher engagement per release
- Premium pricing power
Failure Modes
- Scarcity feels artificial
- Quality doesn't justify wait
- Audience forgets between releases
Brand-Aligned Monetization
How to monetize without degrading brand through selective partnerships
A framework for treating commercial partners as brand signals rather than just revenue sources. Core insight: the right sponsors strengthen brand perception while generating revenue; wrong sponsors destroy more value than they create.
Components
- Define Brand Aspiration
- Identify Signal-Enhancing Partners
- Price Based on Strategic Value
- Integrate Partners Into Content
Prerequisites
- Strong brand identity
- Patience to say no
- Audience trust to protect
Success Indicators
- Partners enhance rather than dilute perception
- Audience accepts sponsor integration
- Premium pricing power with partners
Failure Modes
- Revenue pressure overrides brand discipline
- Wrong partners damage brand equity
- Audience backlash to sponsorships
Stored Potential Energy Management
How to build latent business value not captured in current metrics
A framework for thinking about business decisions through the lens of stored vs. released energy. Core insight: some decisions create immediate visible results; others build invisible reserves that compound over time. Great businesses optimize for stored energy.
Components
- Identify Energy Storage Mechanisms
- Map Energy Release Decisions
- Evaluate Decision Impact on Energy State
- Build Release Criteria
- Communicate Energy Philosophy
Prerequisites
- Financial security to wait
- Long-term orientation
- Stakeholder patience
Success Indicators
- Increasing strategic options over time
- Ability to say no to near-term revenue
- Growing intangible assets
Failure Modes
- Never releasing energy when optimal
- Overestimating stored energy value
- Stakeholder impatience
Structured Improvisation in Creative Work
How to balance prepared structure with spontaneous discovery
A framework for creative collaboration that combines rigorous preparation with real-time improvisation. Core insight: pure improvisation lacks coherence; pure scripting lacks life. The magic is in the tension.
Components
- Separate Research from Performance
- Align on Structure, Not Content
- Prepare Safety Nets
- Create Interject Points
Prerequisites
- Trust between collaborators
- Complementary knowledge
- Shared commitment to quality
Success Indicators
- Authentic surprise on recording
- Coherent narrative arc
- Audience engagement
Failure Modes
- Chaos from under-preparation
- Boredom from over-scripting
- Mismatched expectations
Mental Models (20)
Permission to Educate
PsychologyYou must earn the right to teach. Quality content creates the psychological state where audiences grant permission.
In Practice: Michael Lewis describes how Acquired creates the state where listeners let them teach anything
Demonstrated by Leg-ml-001
Status Competition in Partnerships
PsychologyStatus asymmetry in partnerships creates tension that can drive innovation but also threaten stability.
In Practice: Comparison between Kahneman-Tversky and Gilbert-Rosenthal partnership dynamics
Demonstrated by Leg-ml-001
Scarcity Premium
EconomicsDeliberately created scarcity increases perceived value and attention. When the product is scarce, each instance becomes an event rather than a habit. Scarcity must be authentic to the production process to avoid manipulation perception.
In Practice: NFL's deliberate scarcity strategy and Acquired's adoption of it
Demonstrated by Leg-ml-001
Constraint as Competitive Advantage
Strategic ThinkingOperational constraints can become strategic advantages when leaned into rather than fought against.
In Practice: Hermes Birkin production constraint as business model
Demonstrated by Leg-ml-001
Fixed Production, Infinite Distribution
EconomicsIn digital media, production costs are fixed but distribution costs approach zero. This creates extreme scale economies where outputs scale independently of inputs. Network effects compound this advantage.
In Practice: Ben describing how podcast audience growth changes all outputs without changing inputs
Demonstrated by Leg-ml-001
Network Effects
MathematicsValue increases exponentially as network size grows. Each new user makes the net
In Practice: Internet enabling global niche communities
Demonstrated by Leg-ml-001
Fear as Quality Driver
PsychologyConstructive fear of disappointing your audience maintains quality standards.
In Practice: Ben and David describing terror as part of their creative process
Demonstrated by Leg-ml-001
Crisis Clarity
Decision MakingRevenue shocks and crises force strategic clarity by eliminating marginal options. When resources contract, you must choose what truly matters. Often produces better strategy than expansion periods.
In Practice: 2022 revenue drop forcing focus on quality over volume
Demonstrated by Leg-ml-001
Reputation Compounding
TimeReputation accumulates slowly through consistent behavior but can be destroyed i
In Practice: Sequoia's decision to protect reputation after dot-com crash
Demonstrated by Leg-ml-001
Core Business Recognition
Strategic ThinkingRecognizing when you're already in the best possible business and should stop diversifying. The gras
In Practice: Morris Chang's advice to TSMC to focus on integrated circuits
Demonstrated by Leg-ml-001
Self-Made Prison Avoidance
Decision MakingSuccess creates expectations and infrastructure that become traps. Each hire, office, commitment reduces future optionality. Founders can become prisoners of their own successful companies. Preservation of freedom requires deliberate simplicity.
In Practice: Anonymous investor warning about founders becoming trapped by their own success
Demonstrated by Leg-ml-001
Stored Potential Energy
TimeSome business decisions store latent value (audience trust, brand equity, option
In Practice: Ben introducing stored potential energy as business strategy framework
Demonstrated by Leg-ml-001
Learning Transfer from Research Subjects
Systems ThinkingDeep study of excellent companies or individuals transfers insights that reshape
In Practice: Ben and David realizing their business strategy comes from companies they've stu
Demonstrated by Leg-ml-001
Sponsor as Brand Signal
Strategic ThinkingCommercial partners signal brand positioning to audiences. The right sponsors strengthen brand perce
In Practice: Ben describing selective sponsor strategy
Demonstrated by Leg-ml-001
Event Marketing Leverage
Strategic ThinkingSmall live events create disproportionate brand impact relative to direct audience reach. The idea t
In Practice: Ben explaining that 0.4% live audience creates more impact than full episodes
Demonstrated by Leg-ml-001
Compounding Subscriber Base
MathematicsTrue subscribers compound over time because each new piece of content is guarant
In Practice: Ben explaining podcast subscription mechanics
Demonstrated by Leg-ml-001
Emotion as Signal
PsychologyYour emotional reactions to material signal to the audience what matters.
In Practice: Michael Lewis pointing out emotion as secret sauce
Demonstrated by Leg-ml-001
Risk Creates Engagement
PsychologyAudiences engage more when they sense real-time risk of failure.
In Practice: Michael Lewis explaining audience psychology around scripted vs. improvised performance
Demonstrated by Leg-ml-001
Iteration as Thinking
Decision MakingUnderstanding emerges through multiple passes of material through your brain and hands. First pass identifies, second pass synthesizes, third pass refines. Writing itself clarifies thought; reading your writing clarifies further. You can't think clearly without iteration.
In Practice: David and Michael discussing their shared writing process
Demonstrated by Leg-ml-001
Lossy Communication
PsychologyAll communication is lossy compression: thoughts compress to words, words decompress to different thoughts in the receiver.
In Practice: Ben's lossy compression metaphor and Michael's creative philosophy
Demonstrated by Leg-ml-001
Connective Tissue (4)
Kahneman and Tversky Partnership Dynamic
The collaboration between Daniel Kahneman and Amos Tversky, as documented in The Undoing Project, reveals how status asymmetry and competitive tension can both fuel and threaten creative partnerships. Everyone thought Amos was the smartest person they'd ever met, creating a status differential that made Danny feel at risk of dismissal. In contrast, the Gilbert-Rosenthal partnership lacks this status competition entirely, with no power differential and virtually zero conflict in 10 years. The comparison illuminates how partnership structure fundamentally shapes creative output: competitive partnerships generate breakthrough insights but risk fracture; egalitarian partnerships sustain over time but may lack the friction that produces revolutionary ideas. Both models work, but for different purposes and different personalities.
Michael Lewis explicitly compares the Acquired partnership to Kahneman-Tversky to explore what makes creative collaboration work
Hermes Birkin Bag Production System
Hermes deliberately constrains Birkin bag production by requiring each bag to be handmade by a single artisan from start to finish. This constraint, which could be viewed as an operational limitation, instead becomes the source of the brand's mystique and pricing power. The company builds its business model around the constraint rather than trying to overcome it. Acquired adopted this exact philosophy: rather than fighting their inability to produce high volumes of content (due to being only two people), they leaned into the constraint and made handcrafted, heavily researched episodes the brand's identity. Both Hermes and Acquired convert operational constraints into strategic advantages by making the limitation legible and valuable to their audience. The constraint becomes a quality signal, not a bug to be fixed.
Ben Gilbert explicitly cites Hermes as the model for embracing constraint
Physics Concept of Potential Energy
In physics, potential energy is stored energy that has the capacity to do work but hasn't been released. A boulder at the top of a hill has high potential energy; once it rolls down, that potential energy converts to kinetic energy. Ben Gilbert applies this exact framework to business strategy: some decisions store energy (building audience trust, creating optionality, accumulating brand equity) while others release it (monetization, growth pushes, brand extensions). Great businesses maximize stored potential energy, holding it in reserve until the optimal moment to release it. The physics parallel clarifies a critical strategic insight: not all value shows up in current financials. Some of the most valuable business moves increase potential energy without immediate kinetic results. The framework helps explain why patience and long-term thinking create disproportionate value.
Ben introduces the stored potential energy concept as a mental model for business decisions
Information Theory and Lossy Compression
In information theory, lossy compression (JPEG, MP3) reduces file size by permanently discarding some data that humans can't perceive. The original cannot be perfectly reconstructed. Ben Gilbert observes that language itself is lossy compression: you have a thought, compress it into words, speak it; the listener decompresses those words back into understanding, but what they reconstruct differs from your original thought. Michael Lewis extends this to creative work: when he writes, the meaning that emerges in readers' minds differs from what he intended, but that's not a bug. It's the feature that makes stories alive and durable. By accepting that readers will construct their own meaning, he creates space for interpretation rather than trying to control comprehension. The information theory parallel illuminates why overly didactic work feels dead: it's trying to be lossless when lossy is the human condition.
Ben and Michael discuss the nature of communication and meaning-making in creative work
Key Figures (7)
Michael Lewis
50 mentionsAuthor and Journalist
Warren Buffett
4 mentionsCEO of Berkshire Hathaway
Danny Kahneman
3 mentionsPsychologist and Nobel Laureate
One half of the Kahneman-Tversky partnership that revolutionized behavioral economics.
- Kahneman always felt at risk of being dismissed, thought the lesser partner.
Morris Chang
2 mentionsFounder of TSMC
Ben Thompson
2 mentionsFounder of Stratechery
Amos Tversky
2 mentionsCognitive Psychologist
Doug Leone
2 mentionsFormer Managing Partner at Sequoia Capital
Glossary (2)
affectless
VOCABULARYShowing no emotion or feeling; expressionless
“It was an affectless performance. There was a flatness to it.”
lossy compression
DOMAIN_JARGONData compression where some information is permanently discarded
“Language is a lossy compression of thought.”
Key People (2)
Danny Kahneman
(1934–2024)Nobel Prize-winning psychologist, author of Thinking, Fast and Slow
Amos Tversky
(1937–1996)Pioneering cognitive psychologist, collaborated with Kahneman