Lea's Library
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Lea's Library

Welcome! This is a collection of my favorite tech and startup-related articles, podcasts, & books. Made by Lea Boreland, with love.
TagNameQuoteLinkType
Nugget of Wisdom
4 Extremely Online Writers on How the Internet Broke Our Brains and How We Can Unbreak Them
"I watched a TikTok meme today that made me laugh for 15 minutes, and I was realizing that the thing that always brought me pleasure about the internet was surprise, and the thing that brings the least pleasure about the internet is the lack of surprise. Memes feel surprising so they’re good."
Article
Key To a Universe
A Brief History of the Corporation
"It is sort of vaguely plausible that you could switch artists, politicians and generals around with their peers from another age and still expect them to function. But there is no meaningful way for a businessman from (say) 2000 BC to comprehend what Mark Zuckerberg does, let alone take over for him."
Article
Presents a Model
A Framework for The Metaverse
"We need to think of the Metaverse as a sort of successor state to the mobile internet."
Key To a Universe
A Podcast about Podcasting
"But how do we discover podcasts; is the ideal atomic unit the show, or an individual episode/topic? What makes a good podcast? And given their intimacy, how can brands and communities engage with podcasts?"
Podcast
Presents a Model
A Quantitative Approach to Product-Market Fit
"A quantitative approach to product-market fit for startups is akin to the discipline of financial accounting."
Article
Presents a Model
A Taxonomy of Moats
"Mechanisms to deter or slow imitation are called, colloquially, moats."
Article
Presents a Model
a unified theory of low/no code, middleware, and the future of enterprise applications
"If the engagement channels change, and the data model for viewing, structuring, and managing those interactions changes, what more is Salesforce than a database of customer interactions that are occurring elsewhere?"
Article
Presents a Model
Aggregation Theory
"First, the Internet has made distribution (of digital goods) free, neutralizing the advantage that pre-Internet distributors leveraged to integrate with suppliers. Secondly, the Internet has made transaction costs zero, making it viable for a distributor to integrate forward with end users/consumers at scale."
Article
Presents a Model
All Revenue is Not Created Equal: The Keys to the 10X Revenue Club
"Discounted cash flow (DCF) is an unruly valuation tool for young companies. This is not because it is a bad theoretical framework; it is because we don’t have accurate inputs. Garbage in, garbage out."
Article
Presents a Model
Amazon Prime and other Subscription Businesses: How do you Value a Subscriber?
"These subscription businesses have a revenue profile that is more like an annuity. This revenue profile is not like the manufacturer’s business that many people learned about from a college introduction to accounting class."
Article
Presents a Model
Amazon's New Customer
"This is the key to understanding the purchase of Whole Foods: from the outside it may seem that Amazon is buying a retailer. The truth, though, is that Amazon is buying a customer — the first-and-best customer that will instantly bring its grocery efforts to scale."
Article
Key To a Universe
APIs All the Way Down
"...each [API-first company] represents something that a company would have had to build on its own previously, that it can now do by writing a few lines of code, and do better than they would have ever been able to in-house."
Article
First One to Call It
Balaji Srinivasan on Tim Ferris
"The point is that I think an enormous amount of our media ecosystem today is actually something where the product is terrible, but they’ve got a lot of great legacy distribution."
Podcast
Presents a Model
Bird's new Platform and the Rise of Business-in-a-Box
"The 1946 Federal Lanham Act, which made it safer to license assets to third parties, and the 1956 Federal-Aid Highway Act, which resulted in increasing urban sprawl (Shane), lit a match under the franchise industry.....We see this new group of “Internet franchises” as combining the scale of marketplaces with the ownership and incentive structure of franchises."
Article
Key To a Universe
Blockchain Chicken Farm
"The new socialist countryside will be filled with peasants starting ecommerce businesses, small-scale manufacturing, new data centers, and young entrepreneurial workers returning to their rural homes."
Book
Key To a Universe
Code of Capital
"[Legal] concepts originally devised for real property have been detached from their original object, only to survive and flourish as a means for handling abstract value. The feudal calculus lives and breeds, but its habitat is wealth not land."
Book
Nugget of Wisdom
COGS: How I Bankrupted MoviePass
"What is and isn’t included in various expense lines is always a bit of negotiation. Companies almost always want to add more things below COGS because it makes their business look better."
Article
Key To a Universe
College Football’s Most Dominant Player? It’s ESPN
"...games will not just be televised by ESPN. They are creations of ESPN — demonstrations of the sports network’s power over college football."
Article
Presents a Model
Daniel Kahneman: Putting Your Intuition on Ice
"What we tend to do when we want to move people from A to B is we push them. We add to the driving forces. Kurt Lewin’s insight was that this is not what you should do. You should actually work on the restraining forces and try to make them weaker."
Podcast
Key To a Universe
Debt 2.0 - Funding the Legos of a Modern Business
"Think of assets as lego pieces. Founders build and assemble assets in order to create neat structures which generate revenue - businesses...lenders have been breaking businesses into legos for decades."
Article
First One to Call It
Debt is Coming
"Here is a widely believed cause-and-effect relationship I bet you’ve never thought to invert before: because most startups fail, therefore equity is the best way to finance them. Have you ever considered: because equity is how we finance startups, therefore most startups fail?"
Article
Presents a Model
Designing Good Processes
"In an ideal state, it all just works. Inertia and osmosis do the trick. Everything flows. When and where that’s happening, get out of the way."
Article
Key To a Universe
Digital Theme Park Platforms: The Most Important Media Businesses of the Future
"These parks exist and thrive because of our desire to be “inside a living story”. This was Walt’s primary goal with Disneyland: to go beyond passive consumption and into active immersion."
Article
Nugget of Wisdom
Don't be a generalist.
"Being “a generalist” in a generic context doesn’t mean anything. It’s an excuse by people who fancy themselves clever and scrappy enough to do most anything without prior knowledge or experience. So long as “anything” is high status and interesting, that is."
Article
Key To a Universe
Email Addresses and Razor Blades
"In the end, no DTC company was actually good at marketing; they outsourced it to Google and Facebook."
Article
Nugget of Wisdom
Finance is Broken But Don’t Worry, This Has Happened Before
"When you look at a [financial statement], you need to know that what was shown was a choice, not a result."
Article
Presents a Model
Five ways to build a $100 million business
"Some time ago my friend...wrote a great blog post about "the only 2 ways to build a $100 million business". I'd like to expand on the topic and suggest that there are five ways to build a $100 million Internet company."
Article
Presents a Model
Focus is for Winners
"Companies should want to make money, because, besides money being generally a good thing (I think?), it’s the right way not to be distracted."
Article
Key To a Universe
Founder's Field Guide: Michael Mayer - Business Boss Battles
"We sort of realized that replenishment of consumables was broken broadly."
Podcast
Key To a Universe
Founder's Field Guide: Will Ahmed - Optimizing Human Performance
"In a lot of ways, WHOOP is the first fitness product to tell you not to exercise."
Podcast
Presents a Model
FOUR FITS FOR $100M+ GROWTH
"Building a great product is a piece of the puzzle, but it’s far from the full picture."
Article
Presents a Model
Functional vs Unit Organizations
"Therefore, when you create an org chart you are creating your product — the seams in the org get reflected in the product; the depth of feature work gets reflected in resource allocation; the coordination across job functions gets reflected by the leaders you choose, and so on."
Article
Key To a Universe
Hash Power
"Every attempt to nail down digital assets has basically failed until the blockchain. And that's it. That's what the blockchain is. It's just a way to track the ownership of digital assets."
Article
Presents a Model
How Carta is Set to Unlock the Private Markets
"The N-of-1 companies become immovable central fixtures — utilities. In doing so, N-of-1 companies transform from merely services to central utilities that power entire ecosystems."
Article
Presents a Model
How Superhuman Built an Engine to Find Product/Market Fit
"...just ask users “how would you feel if you could no longer use the product?” and measure the percent who answer 'very disappointed.'"
Article
Nugget of Wisdom
How to Shape Remarkable Products in the Messy Middle of Building Startups
"In the beginning of your journey, simple solutions come easily. But as the middle becomes volatile and more problematic, we have the tendency to add complexity. We solve problems by adding more options, more features, and more nuances to our creations."
Article
Presents a Model
How to Succeed in Business by Bundling - or Unbundling
"...there are only two ways to make money in business: One is to bundle; the other is unbundle.'"
Article
Presents a Model
Introduction to the Sales and Marketing Machine
"One of the biggest causes of failure that I have found, is not well recognized or discussed: the inability to acquire customers in a cost effective way."
Article
Nugget of Wisdom
Inventing on Principle (Bret Victor)
"Larry Tesler likes simplicity. But his principle was this specific nugget of insight: No person should be trapped in a mode. And that is a powerful principle because it gave him a new way of seeing the world. It divided the world in right and wrong in a fairly objective way. So, he could look at somebody selecting text and ask: Is this person in a mode? Yes or no? If yes, he had to do something about that."
Article
Nugget of Wisdom
Investors Beware: Today’s $100M+ Late-stage Private Rounds Are Very Different from an IPO
"This requires analyzing the “true” contribution margin of the business; not simply looking at gross or net revenue and the proper contra-revenue treatment, and not even looking just at gross margin as defined by the company."
Article
Key To a Universe
Invisalign—Patents, Patients, Profits
"You look at a $200 or $300 product that's sold to the end consumer for $5,000 or $6,000 and it makes sense why your town orthodontist is working four days a week and driving around in a Porsche and playing golf."
Podcast
Key To a Universe
Invisible Asymptotes
"For so many startups and even larger tech incumbents, the point at which they hit the shoulder in the S-curve is a mystery, and I suspect the failure to see it occurs much earlier."
Article
Key To a Universe
Is it time to ditch the old SaaS metrics?
"Return on Incremental Invested Capital (ROIIC): Think of this as a more PLG-centric way of understanding CAC payback that helps you make the right trade-offs between growth investments whether they be in sales, marketing, product, M&A, or elsewhere."
Article
Key To a Universe
Kat Cole - Cinnabon: The Omnichannel Approach to Indulgence
"In the Great Recession...there were years of deferred CapEx....The product wasn't being marketed or innovated...it was just losing relevance by its own design."
Podcast
Key To a Universe
Learnings from a Year of Unexpected Events
"Fewer and fewer younger people want to get into the trades. When I say the trades, these are typically dirty jobs...[but] they're fairly highly skilled jobs. Plumbing a pool is something that takes 8, 10, 12 years to become good at it. Can you do it before then? Of course. But can you do it with excellence? Can you do it with speed, the lack of mistakes? No. It takes a long time to get good at it. And the same thing would be for how you dig a pool out."
Podcast
Presents a Model
Making Uncommon Knowledge Common
"Rich Barton’s companies became public Schelling Points. They create common knowledge in their industries from information only middlemen had access to before, from public-but-hard to aggregate data, or from information collected from users themselves."
Article
Key To a Universe
Market-Expected Return on Investment: Bridging Accounting and Valuation
"Categorization is a challenge today because income statements conflate expenses and investments"
Article
Key To a Universe
Media for Thinking the Unthinkable
"Richard Hamming suggested that, like sounds we cannot hear, there could be thoughts we cannot think."
Article
Key To a Universe
Mental Mountians
"[The] brain is a mountainous landscape, with fertile valleys separated by towering peaks. Some memories (or pieces of your predictive model, or whatever) live in each valley. But they can’t talk to each other. The passes are narrow and treacherous. They go on believing their own thing, unconstrained by conclusions reached elsewhere."
Article
Key To a Universe
Neuralink and the Brain's Magical Future
"600 million years ago, no one really did anything, ever....But then came the jellyfish."
Article
Key To a Universe
Nintendo, Disney, and Cultural Determinism
"Nintendo owns much of the most valuable gaming IP in the world. It also has one of the most unique approaches to deploying this IP."
Article
Nugget of Wisdom
On Business Books
"Executives should read fewer management books."
Article
Presents a Model
On Pioneers, Settlers, Town Planners and Theft
"I often talk about the use of cell based structures...which are populated not only with aptitude (the skill to do something) but the right attitude (type of people)."
Article
Key To a Universe
Roads and Bridges: The Unseen Labor Behind our Technological Infrastructure
"Facebook did not actually build all the pieces necessary to make it possible for you to post to their app. Instead, they use free, public code, made available on the Internet by volunteers for anybody to use."
Article
Key To a Universe
Seeing Like An Algorithm
"...the nation-state uses simplifying abstractions to “see” its citizens at a synoptic level. I want to discuss how TikTok’s application design allows its algorithm to “see” all the detail it needs to perform its matchmaking job efficiently and accurately."
Article
Nugget of Wisdom
Software, Full Stack, and Sumo Startups
"Nike and Coca-Cola are in the business of producing and marketing emotionally-resonant 30-second films, as well as running a global logistics system. They get paid when, as a side effect of this, somebody buys a very marked-up pair of shoes or can of carbonated high-fructose corn syrup with a splash of water and some food coloring."
Article
Nugget of Wisdom
Software, the Tough Tomato Principle, and the Great Weirdening of the World
"So I’ll just go ahead and call it the Tough Tomato Principle: we make tools so they accommodate the world; until the world remolds itself so it accommodates our tools."
Article
Key To a Universe
Spatial Interfaces
"We already have concepts like "back" and "forward" for navigation...There's more room for spatial concepts to become part of our web browsing experience."
Article
Presents a Model
Technological Revolutions and Financial Capital
"Financial capital and production capital are interrelated but functionally separate agents, each pursuing profits with different criteria and behaviors"
Book
Key To a Universe
the 4 kinds of side businesses you can start
"this is my favorite way to launch a side business: spend time on a marketplace where people are spending money, and figure out how to create a product that people are looking for."
Article
Key To a Universe
The Age of the Remix
"Recently, we've seen the humble word processor get refactored. Tools have emerged that make it easier to splice additional functionality into the writing process, build off other users' work, or draw on one's own ideas."
Article
Key To a Universe
The American Cloud
"But that is the sort of unexpected juxtaposition you routinely encounter when you explore the interior of the American cloud... It’s a space where naked technological realities accumulate behind the scenes in order to enable American life."
Article
Presents a Model
The Arc of Collaboration
"The arc of collaboration is long and it bends in the direction of functional workflows."
Article
Key To a Universe
The Audio Revolution
"What’s hottest? You might think that the highest-resolution format of all could be visual, typographic or video. But it’s not. It’s audio."
Article
Presents a Model
The Cadence: How to Operate a SaaS Startup
"The Cadence is designed to synchronize the major functions of a SaaS startup so that the team works together in lockstep. It brings order to the chaos; it turns the shitshow into an army."
Article
Presents a Model
The data team: a short story
"What I think makes most sense to push for is a centralization of the reporting structure, but keeping the work management decentralized. Why? Primarily because it creates a much tighter feedback loop between data and decisions."
Article
Presents a Model
The Economics of Customer Businesses
"Customer-based corporate valuation...links customer economics to corporate value. This allows investors to build a model, based on the drivers of customer value from the bottom up, that generates a warranted stock price."
Article
Key To a Universe
The Evolution of Cooperation
"There is a lot to be learned about coping in an environment of mutual power."
Book
Presents a Model
The Hierarchy of Engagement
"As companies move up the hierarchy, their products become better, harder to leave, and ultimately create virtuous loops that make the product self-perpetuating."
Article
Nugget of Wisdom
The high-return activity of raising others’ aspirations
"At critical moments in time, you can raise the aspirations of other people significantly, especially when they are relatively young, simply by suggesting they do something better or more ambitious than what they might have in mind."
Article
Nugget of Wisdom
The Idea Maze
"In other words: a good idea means a bird’s eye view of the idea maze, understanding all the permutations of the idea and the branching of the decision tree, gaming things out to the end of each scenario."
Article
Presents a Model
The Innovator's Dilemma
"Sound managerial decisions are at the very root of [the incumbents'] impending fall from industry leadership.”
Book
First One to Call It
The Long Tail
"The future of entertainment is in the millions of niche markets at the shallow end of the bitstream."
Article
Key To a Universe
The Outsiders: Eight Unconventional CEOs and Their Radically Rational Blueprint for Success
"In all cases...[outsider CEOs] focus on cash flow....[and forgo the] holy grail of reported earnings.”
Book
Key To a Universe
The Past, Present, and Future of SaaS and Software
"That isn't to say that the [Graphical User Interfaces] go away. If you think of Stripe, there's plenty of GUIs in Stripe. It's just that the primary consumption vehicle of Stripe isn't a GUI. It's the API."
Article
First One to Call It
The rise of community-curated knowledge networks
"We are living through the emergence of a new business category that doesn’t even have a name yet, but which I believe will become an important part of our digital lives: online communities at the intersection of content curation and knowledge management."
Article
First One to Call It
The Rise of Platform Brands
"Rather than building brands solely through corporate channels, these companies give employees the permission and infrastructure to build affinity with customers on the company’s behalf."
Article
Presents a Model
The Secret 3-Step Master Plan to Cure Healthcare
"NexHealth’s big insight was this: to build a “single API for healthcare,” you actually don’t start API-first. And you don’t go through the gatekeepers, you go around them.
Article
Key To a Universe
The Utopian UI Architect
"Now we’re staring at computer screens and moving our hands on a keyboard, but it’s basically the same thing. We’re computer users thinking paper thoughts.”
Article
Presents a Model
Theory of Constraints 101: Applying the Principles of Flow to Knowledge Work
"The performance of the system as a whole is limited by the output of the tightest bottleneck or most limiting constraint."
Article
Key To a Universe
Thinking in Systems
"Everything you know, and everything everyone knows, is only a model."
Book
Key To a Universe
Trick Mirror
"I’ll sit there like a rat pressing the lever, like a woman repeatedly hitting myself on the forehead with a hammer, masturbating through the nightmare until I finally catch the gasoline whiff of a good meme.”
Book
Presents a Model
Twilio—Messaging, Margins, and Markets
"It's just one of these totally counterintuitive business things you'd never expect where it's almost like he locked the spinal cord down, even though it was a little expensive or maybe not as pretty on a spreadsheet."
Podcast
Presents a Model
Unbundling Work from Employment
"The notion of the “organization man”...is giving way to the rise of “micro-entrepreneurs,” or free agents, creators, freelancers, and independent workers who utilize digital platforms to make a living by leveraging skills and knowledge in the absence of a traditional employer-employee relationship."
Article
First One to Call It
Underuitilized Fixed Assests
"The best way to think of underutilized fixed assets is as pure potential energy sitting in people’s homes, cars, and random tchotkes."
Article
Presents a Model
Unit Economics and the Pursuit of Scale Invariance
"The framework presented here for [unit economics] focuses on what it costs to generate an observed pattern of PMF with a similar focus on empirical observation."
Article
Key To a Universe
Venture Capital: An American History
"The investment models behind whaling expeditions and venture capital funds can be thought of as interchangeable..."
Book
Presents a Model
Vinny Pujji - Calm: The Sleeping Giant
"In reality, content as a utility has been limited largely to education and it's not fun or relaxing, typically. Content for entertainment is what we all think of, right? That's Disney. But content for utility has usually been okay, I'm going to go on to Khan Academy..."
Podcast
Nugget of Wisdom
We Don't Sell Saddles Here
"To see why, consider the hypothetical Acme Saddle Company. They could just sell saddles, and if so, they’d probably be selling on the basis of things like the quality of the leather they use or the fancy adornments their saddles include; they could be selling on the range of styles and sizes available, or on durability, or on price. Or, they could sell horseback riding."
Article
Key To a Universe
What is a Tech Company?
"....over time, the product enterprises were paying for was improving. This is in direct contrast to a physical asset that deteriorates, or a traditional software support contract that is limited to a specific version."
Article
Key To a Universe
What is Amazon?
"Jeff Bezos had a big realization in 1994: the world of retail had, up until then, been a world where the most important thing was optimizing limited shelf space in service of satisfying the customer – but that world was about to change drastically."
Article
Key To a Universe
What Is an Entertainment Company in 2021 and Why Does the Answer Matter?
"if you accept that an entertainment company is about love building, that means every entertainment company must be in a process of constant change — from where it tells stories, to where you build love, and how it monetizes."
Article
Nugget of Wisdom
What it’s like to work for Stripe
"By convention, every email at Stripe is CC-ed to lists that go to either the entire company or to any particular team. This includes internal person-to-person correspondence."
Article
Key To a Universe
What You Learn About Business from 12,000 Deals...
"We've looked at hundreds and hundreds of HVAC companies and we love the space. We think that it's a really promising area that can also have a lot of innovation hit from a consumer of the product standpoint."
Podcast
First One to Call It
When tailwinds vanish
"What are the practical consequences of the Internet’s shift towards maturation?... We’ll see an acceleration of zero-sum games between Internet startups and incumbents. A shift from R&D to SG&A will operationalize Silicon Valley, leaving room for new financial infrastructure. VCs will need to take risks on vision, not numbers. And the founders and operators of tomorrow won’t look like those of the past 20 years."
Article
Nugget of Wisdom
Why Naval Ravikant Hires Artists
"The best people in any industry on the planet—whether they're building rockets or electric cars—are artists.”
Article
First One to Call It
Why the Next Sports Empire will be Built on eSports
"ESPN’s investment in the NCAA speaks to the ways in which the right partner – one that knows how to stage events, build audience and attract advertisers – could bring out the full potential of the eSports industry."
Article
Nugget of Wisdom
Why We Crave Software With Style Over “Branding”
"Part of this, I believe, is about bringing back an opinionated approach to software design, where the tool asserts itself."
Key To a Universe
Xin Yi Lim - Pinduoduo: Rise of Social Commerce
"Pinduoduo has been described before as a mix of Costco and Disneyland."
Podcast
Nugget of Wisdom
You're in the business of selling promotions
"Ultimately, software is purchased by an individual on behalf of a corporation. Behind the logo on the lead list is a person. That champion stakes some part of their reputation on the investment they beseech the company to make. Successful sales people sell promotions."
Article