Rex Woodbury

Rex Woodbury


242 Quotes

"Google in 2019 announced that 5 million businesses pay for Workspace, while Microsoft has said that over 200 million businesses pay for its Office 365 suite."
Rex Woodbury
Enterprise Software Is Dead. Long Live Enterprise Software.
"“the consumerization of the enterprise”—work tools were becoming as elegant and user-friendly as consumer apps. Furthermore, many tools were tailored to a specific user within an organization, making them superior to broad catch-all tools like PowerPoint, Word, and Outlook."
Rex Woodbury
Enterprise Software Is Dead. Long Live Enterprise Software.
"More remote and distributed teams means more emphasis on knowledge management within organizations. People need to know what’s going on and where to find important information—especially when they’re working from home, often in far-flung corners of the globe."
Rex Woodbury
Enterprise Software Is Dead. Long Live Enterprise Software.
"Online identity is becoming more complex, dynamic, and multi-faceted. Managing identity is a massive headache for organizations."
Rex Woodbury
Enterprise Software Is Dead. Long Live Enterprise Software.
"Identity underpins every interaction and every transaction on the internet, yet the infrastructure of identity was built for an analog world. Social security numbers. Physical addresses. Security questions."
Rex Woodbury
Enterprise Software Is Dead. Long Live Enterprise Software.
"The trend-line in all companies is toward more transparency: data is power, and workers are becoming more equipped to understand what’s going on, how to fix it, and how to prevent it from happening next time."
Rex Woodbury
Enterprise Software Is Dead. Long Live Enterprise Software.
"the reality is you can be a great painter and not know anything about making paint. And I think you can build great products with large models without knowing exactly how they’re made."
Rex Woodbury
Enterprise Software Is Dead. Long Live Enterprise Software.
"AI-powered tools aren’t themselves a category, but rather a new vector cutting across functions and verticals."
Rex Woodbury
Enterprise Software Is Dead. Long Live Enterprise Software.
"enterprise SaaS may not be as “hot” a space as it once was, but there’s still innovation happening. Work is changing rapidly, with the rise of remote, distributed teams; with leaps forward in AI; with both the continued digitization of work and the continued consumerization of the enterprise."
Rex Woodbury
Enterprise Software Is Dead. Long Live Enterprise Software.
"One dramatic oversimplification is that use cases can be grouped into two buckets: 1) Creativity, and 2) Productivity."
Rex Woodbury
AI in 2023: The Application Layer Has Arrived
"Copilot now generates about 40% of code in the projects where it’s installed, headed to 80% within five years."
Rex Woodbury
AI in 2023: The Application Layer Has Arrived
"We’re in the very early innings of applications, and it’s too early to tell what the killer apps will be. A looming question mark is how companies will build competitive moats; true tech differentiation is rare, and companies will need to find ways to stay ahead of competition, perhaps with network effects or with iterative loops of user engagement and product refinement."
Rex Woodbury
AI in 2023: The Application Layer Has Arrived
"My hunch is that many of the best AI startups will be SaaS companies."
Rex Woodbury
AI in 2023: The Application Layer Has Arrived
"The short answer for business models in AI applications is that we’ll likely see the same go-to business models that have powered tech (and business writ large) over the last generation."
Rex Woodbury
AI in 2023: The Application Layer Has Arrived
"Marketplaces will likely (again) prove to be more capital intensive to scale, but will (again) have powerful network effects that provide strong moats. And SaaS will (again) prove to be among the most desirable business models, though AI SaaS companies will need best-in-class products to cut through the noise of how crowded enterprise SaaS has become."
Rex Woodbury
AI in 2023: The Application Layer Has Arrived
"the Wharton professor Ethan Mollick, who argues, “Large language models aren’t going to get less capable in the next few years. We need to figure out a way to adjust to these tools, and not just ban them.” Today’s kids will live in a world teeming with AI; they need to understand how to navigate that world."
Rex Woodbury
AI in 2023: The Application Layer Has Arrived
"What does it mean when computers are better at visual imagination than 99 percent of humans? That doesn’t mean we will stop imagining. Cars are faster than humans, but that doesn’t mean we stopped walking. When we’re moving huge amounts of stuff over huge distances, we need engines, whether that’s airplanes or boats or cars. And we see this technology as an engine for the imagination. So it’s a very positive and humanistic thing."
Rex Woodbury
AI in 2023: The Application Layer Has Arrived
"Just as AI amplifies creativity, AI amplifies productivity. We see this in the tools that give writers and marketers superpowers, like Jasper.ai, Copy.ai, and Lex."
Rex Woodbury
AI in 2023: The Application Layer Has Arrived
"AWS launched in 2006; the iPhone came out in 2007. Neither mobile nor cloud are saturated, but they aren’t as ripe for greenfield opportunity as they once were. At the same time, we’ve seen an unprecedented influx of private capital chasing startups"
Rex Woodbury
The TikTokization of Everything
"Perhaps the most compelling—and the most likely—force to power tech in the 2020s is artificial intelligence. AI has improved dramatically within the past few years."
Rex Woodbury
The TikTokization of Everything
"What we’re seeing is AI emerge from the infrastructure layer to the application layer—the parts of technology that everyday people interact with. The breakthrough use case in recent months has been text-to-image generative art"
Rex Woodbury
The TikTokization of Everything
"perhaps no use of AI is more visible to more people than TikTok’s For You Page."
Rex Woodbury
The TikTokization of Everything
"The major consumer applications of AI will lean heavily into sophisticated recommendations that anticipate your wants and desires before you even know them"
Rex Woodbury
The TikTokization of Everything
"The basic principle stands: Netflix pours billions into expensive content, while YouTube taps the world’s creativity."
Rex Woodbury
The Long Tail: The Internet and the Business of Niche
"Netflix is a business built on heavy-hitters (expensive productions like Stranger Things, The Witcher, and Squid Game), while YouTube is built on volume—500 hours of video are added every minute. YouTube is built on the long tail."
Rex Woodbury
The Long Tail: The Internet and the Business of Niche
"The concept of the long tail was popularized by Chris Anderson in an October 2004 article in WIRED."
Rex Woodbury
The Long Tail: The Internet and the Business of Niche
"“Forget squeezing millions from a few megahits at the top of the charts. The future of entertainment is in the millions of niche markets at the shallow end of the bitstream.”"
Rex Woodbury
The Long Tail: The Internet and the Business of Niche
"The concept of the long tail remains one of the best investing frameworks for internet companies. Many of the most successful technology companies in history have been built on the long tail."
Rex Woodbury
The Long Tail: The Internet and the Business of Niche
"One of the powers of the long tail is its ability to expand selection. Amazon might be the best example."
Rex Woodbury
The Long Tail: The Internet and the Business of Niche
"for long tail companies to succeed, they need to ensure that niche products are in stock when you need them"
Rex Woodbury
The Long Tail: The Internet and the Business of Niche
"When more selection is available, customer preferences and interests become much more readily apparent than when tastes are curated by a handful of executives."
Rex Woodbury
The Long Tail: The Internet and the Business of Niche
"Another facet of the long tail—paired with this greater selection—is that the long tail helps customers discover new products."
Rex Woodbury
The Long Tail: The Internet and the Business of Niche
"Recommendations (and paid placement) on Amazon dictate the flows of billions of dollars spent on commerce; Netflix and YouTube algorithms shape culture; and Spotify’s recommendation-based playlists move music."
Rex Woodbury
The Long Tail: The Internet and the Business of Niche
"The two major categories for the long tail framework are content and commerce."
Rex Woodbury
The Long Tail: The Internet and the Business of Niche
"TikTok relies heavily on remix culture, allowing people to build on each other’s sounds and trends; this removes the friction to create that exists even with robust creation tools (“What video should I make?”) and leads to a stunning amount of creativity."
Rex Woodbury
The Long Tail: The Internet and the Business of Niche
"As creation gets even easier, the long tail will continue to lengthen."
Rex Woodbury
The Long Tail: The Internet and the Business of Niche
"Innovations like Midjourney, DALL-E, and StableDiffusion—which provide text to image AI generation—may unlock new levels of creativity and expression. This will shift content even more away from the handful of big-budget hits, and more to the long tail of creators."
Rex Woodbury
The Long Tail: The Internet and the Business of Niche
"There’s one characteristic that many of the most successful internet businesses share: they create more jobs through their platform than the company could ever directly employ."
Rex Woodbury
The Long Tail: The Internet and the Business of Niche
"Chris Paik calls this “off-balance sheet operating leverage.” Can a company enable an entire ecosystem to form on top of it? Companies that have off-balance sheet operating leverage are often the companies that rely on the long tail."
Rex Woodbury
The Long Tail: The Internet and the Business of Niche
"One of the earliest recorded forms of commerce was cattle trade, around 10,000 B.C. Cattle had a fixed value and were exchanged for goods and services"
Rex Woodbury
CAC: Customer Acquisition Chaos
"Commerce is now a $26 trillion global market (e-commerce is about $10 trillion), mostly underpinned by cash, credit cards, debit cards, and, increasingly, digital payments."
Rex Woodbury
CAC: Customer Acquisition Chaos
"There are two primary types of shopping: search-driven shopping and discovery-driven shopping. Today, Amazon dominates search-driven shopping: 74% of online shopping searches in the U.S. now originate on Amazon.com"
Rex Woodbury
CAC: Customer Acquisition Chaos
"Amazon’s dominance in search-driven shopping is a key reason it’s been able to build a formidable advertising business in a few short years."
Rex Woodbury
CAC: Customer Acquisition Chaos
"Now Amazon is a top-5 global business by advertising revenues."
Rex Woodbury
CAC: Customer Acquisition Chaos
"Looking at 2022 data vs. that ~2020 data, Amazon’s ad revenue is already up to $30B+. Amazon is a certified advertising behemoth."
Rex Woodbury
CAC: Customer Acquisition Chaos
"Discovery-driven shopping is the mall. It’s wandering around, browsing, deciding what you might want to buy. Discovery-driven shopping is about serendipity."
Rex Woodbury
CAC: Customer Acquisition Chaos
"In the U.S., social commerce hasn’t taken off to the same degree as in China; rather, commerce seems to be layered on top of existing social platforms (Instagram, Pinterest, Facebook Marketplace), rather than companies blending social + commerce from the get-go."
Rex Woodbury
CAC: Customer Acquisition Chaos
"there are two types of advertising worth knowing: direct response advertising, which has the goal of making a transaction happen then and there, and brand advertising, which has the goal of building brand equity."
Rex Woodbury
CAC: Customer Acquisition Chaos
"The classic example of brand advertising, meanwhile, is Coca-Cola. Coke doesn’t care that you buy that Coke right now, but rather that next time you’re thirsty at a movie theater, you reach for a Coke and not a Pepsi."
Rex Woodbury
CAC: Customer Acquisition Chaos
"Most estimates have direct response comprising about 80% of all digital ad dollars spent online."
Rex Woodbury
CAC: Customer Acquisition Chaos
"when CACs got too high, DTC brands opted to go the old-fashioned route: brick-and-mortar locations."
Rex Woodbury
CAC: Customer Acquisition Chaos
"Brands like Warby Parker and Jessica Alba’s Honest Company now get 50% or more of their revenue from physical retail locations"
Rex Woodbury
CAC: Customer Acquisition Chaos
"Influencer marketing is one option, and the industry has swelled from $1.7 billion in 2016 to $16.4 billion in 2022 (a 46% CAGR). Influencer underpins discovery-driven commerce."
Rex Woodbury
CAC: Customer Acquisition Chaos
"But influencer marketing is also broken. As I wrote in May’s Influencer Marketing 2.0, most influencer campaigns rely on hefty upfront lump-sum payments and use hacks like discount codes to track attribution. ROI is often poor, and measurement is even worse. The channel is difficult to scale efficiently."
Rex Woodbury
CAC: Customer Acquisition Chaos
"Brands need new channels. One opportunity: creators."
Rex Woodbury
CAC: Customer Acquisition Chaos
"Brands care about a few things: 1) They only want to pay when they’ve acquired a new customer and done so profitably; 2) They want to control who can sell / promote their brand and where; and 3) They want the ability to measure what’s working and know what’s worth doubling down on."
Rex Woodbury
CAC: Customer Acquisition Chaos
"Kaitlyn Tiffany wrote in The Atlantic, “Whereas Facebook aimed to bring everyone and their mother online, Tumblr was the opposite: an online underground, a place where your mother, in particular, would never see you.”"
Rex Woodbury
Myspace, Tumblr, and the Long-Lost Weirdness of the Social Internet
"While Facebook’s market cap soared to $1 trillion, Tumblr was sold to Yahoo in 2013 for $1.1 billion and then to Automattic in 2019 for just $3 million."
Rex Woodbury
Myspace, Tumblr, and the Long-Lost Weirdness of the Social Internet
"Myspace, like Tumblr, put customizability front and center. Then Facebook came along and stamped out individuality."
Rex Woodbury
Myspace, Tumblr, and the Long-Lost Weirdness of the Social Internet
"You’d want to be radically different from all others. And that was the real value of Myspace. When people talk about missing Myspace, they miss customizing their profile."
Rex Woodbury
Myspace, Tumblr, and the Long-Lost Weirdness of the Social Internet
"New social platforms are ripe to be built, each emphasizing creativity and customizability. Three areas that interest me are: 3D creative expression Memes Pseudonymity"
Rex Woodbury
Myspace, Tumblr, and the Long-Lost Weirdness of the Social Internet
"There are opportunities to create 3D spaces that are purpose-built for social and that are more customizable for your everyday user."
Rex Woodbury
Myspace, Tumblr, and the Long-Lost Weirdness of the Social Internet
"Memes are how ideas move between people via culture and—as with all forms of communication—the internet dramatically accelerated the speed and scale with which those ideas move."
Rex Woodbury
Myspace, Tumblr, and the Long-Lost Weirdness of the Social Internet
"Memes are the language of the digital natives: people who grew up online innately understand and communicate via memes, and new tools make memes easier to create and share."
Rex Woodbury
Myspace, Tumblr, and the Long-Lost Weirdness of the Social Internet
"Over the past 50 years, there’s been a massive shift toward individuality."
Rex Woodbury
Myspace, Tumblr, and the Long-Lost Weirdness of the Social Internet
"We used to give our kids popular names so that they fit in. The goal was to conform. The name Mary was the most popular girls name for all but six years (!) from 1880 to 1961."
Rex Woodbury
Myspace, Tumblr, and the Long-Lost Weirdness of the Social Internet
"In 1880, 32% of kids got a top-10 most-popular name; by 1950, it was down to 28%; and by 2020, it was 7%. The pendulum of culture has shifted from the collective to the individual. We now give kids distinctive and unique names so that they stand out."
Rex Woodbury
Myspace, Tumblr, and the Long-Lost Weirdness of the Social Internet
"People no longer want to have the same online persona as everyone else—people want to stand out. Platforms that allow self-expression, often by allowing you to adopt a new online identity, will thrive in a world built for the individual."
Rex Woodbury
Myspace, Tumblr, and the Long-Lost Weirdness of the Social Internet
"Your identity becomes not a form you fill out on a profile, but something you choose."
Rex Woodbury
Myspace, Tumblr, and the Long-Lost Weirdness of the Social Internet
"The best online spaces feel like this: entire new universes where anything is possible."
Rex Woodbury
Myspace, Tumblr, and the Long-Lost Weirdness of the Social Internet
"One interesting trend over the past few years has been the return of Y2K culture, as Gen Zs embrace 90s and naughts fashion and music and aesthetics."
Rex Woodbury
Myspace, Tumblr, and the Long-Lost Weirdness of the Social Internet
"Even though 3.4 billion people play video games—and even though the industry is larger than the music, box office, and sports industries combined—gaming still gets a lot of eye-rolls."
Rex Woodbury
Digital Economies, Gaming, and IP Legos
"the average age of a U.S. gamer is 35; that close to half (45%) of gamers are women; and that gaming is deeply social."
Rex Woodbury
Digital Economies, Gaming, and IP Legos
"Nintendo was founded the same year that Vincent Van Gogh painted Starry Night. Nintendo started out in 1889 making playing cards"
Rex Woodbury
Digital Economies, Gaming, and IP Legos
"Abstracting complexity is how crypto goes mainstream."
Rex Woodbury
Digital Economies, Gaming, and IP Legos
"Blockchain-Based Economies Modding and UGC IP Legos"
Rex Woodbury
Digital Economies, Gaming, and IP Legos
"One of the key gameplay pillars is “Access for All”, ensuring that the game is playable and fun with or without crypto"
Rex Woodbury
Digital Economies, Gaming, and IP Legos
"Axie’s economy has an inflation problem (much like our real-world economy!), as more players are cashing out than are putting money into the game."
Rex Woodbury
Digital Economies, Gaming, and IP Legos
"In the early days of gaming, modding was the original form of user-generated content; modding was the only way that an amateur creator could make something."
Rex Woodbury
Digital Economies, Gaming, and IP Legos
"Modding is important because it’s a way that creators can directly participate in digital worlds, unlocking the creativity of millions of individuals. It’s a critical piece of gaming, and it’s about to intersect with blockchain economies."
Rex Woodbury
Digital Economies, Gaming, and IP Legos
"What’s fascinating about many of the crypto projects popping up is that they sacrifice copyright rights, granting everyone the opportunity to build with IP."
Rex Woodbury
Digital Economies, Gaming, and IP Legos
"In Web2, modding has been a key unlock for tapping the community’s creativity—crowdsourcing creativity always results in more innovation than a studio or publisher or initial creator could dream up alone. Web3 layers in the economics."
Rex Woodbury
Digital Economies, Gaming, and IP Legos
"the next iconic IP might be community-owned"
Rex Woodbury
Digital Economies, Gaming, and IP Legos
"the platforms are built for advertisers, not for creators and communities."
Rex Woodbury
Social Tokens and Creator-Centric Economies
"Virtual goods are already mainstream. Bringing digital assets onto the blockchain simply unlocks scarcity, which unlocks incremental value."
Rex Woodbury
Social Tokens and Creator-Centric Economies
"RAC distributed $RAC retroactively to fans based on their fandom—whether they’d been a Patreon supporter, whether they’d bought merch in the past, and so on."
Rex Woodbury
Social Tokens and Creator-Centric Economies
"given that social tokens involve people—often famous people—creating their own economies, social tokens will eventually be as buzzy, disruptive, and public-facing as NFTs."
Rex Woodbury
Social Tokens and Creator-Centric Economies
"In launching $JROCK, Clark effectively creates a digital economy around himself. This is what makes social tokens so interesting: they remove intermediaries, letting artists, athletes, and other influential people interact directly with fans."
Rex Woodbury
Social Tokens and Creator-Centric Economies
"This is a groundbreaking idea: tokenized fan communities reward the most devoted and earliest fans, rather than those with the most money."
Rex Woodbury
Social Tokens and Creator-Centric Economies
"Social tokens better express the breadth and depth of a community. In the future, instead of measuring a creator’s clout based on her Instagram following, we’ll point to her market cap."
Rex Woodbury
Social Tokens and Creator-Centric Economies
"In the future, we’ll buy, sell, and compare creator tokens as easily as we buy, sell, and compare stocks today. The experience might live in a Coinbase-like interface for trading social tokens."
Rex Woodbury
Social Tokens and Creator-Centric Economies
"There are tools that let anyone create a social token. $KERMAN, for instance, used Roll. Artists like Portugal. The Man have used Rally, “a platform for creators and their communities to build their own independent digital economies.”"
Rex Woodbury
Social Tokens and Creator-Centric Economies
"if we fast forward to 2030 or 2040, I don’t expect that everyone will have a token. Rather, high-profile people will launch tokens—people who today have a large presence on YouTube, TikTok, Twitter, and Instagram. You might participate in the digital economy of your favorite musician, actor, writer, athlete, or entrepreneur."
Rex Woodbury
Social Tokens and Creator-Centric Economies
"To participate in digital economies, people won’t need to understand what “fungible” or “on chain” mean—they will just need to understand that there are only X digital items in existence, or that a creator has Y social tokens in circulation."
Rex Woodbury
Social Tokens and Creator-Centric Economies
"The underlying concept of social tokens—buying “stock” in people you believe in and want to support—will make social tokens uniquely easy to grok."
Rex Woodbury
Social Tokens and Creator-Centric Economies
"technology renders gatekeepers obsolete"
Rex Woodbury
Social Tokens and Creator-Centric Economies
"The promise of the internet was to remove gatekeepers."
Rex Woodbury
Social Tokens and Creator-Centric Economies
"social tokens are fascinating because they combine investing, patronage, and gated access in unique ways—all in a cross-platform, unified architecture."
Rex Woodbury
Social Tokens and Creator-Centric Economies
"There are nearly 3 billion Gen Zs alive today. In 2019, Gen Zs surpassed Millennials to become the largest generation on the planet. And with the oldest Gen Zs still only 26, the generation’s $150 billion in spending power will swell 70% over the next five years."
Rex Woodbury
A Guide to Gen Z Through TikTok Trends, Emojis, & Language
"The trend captures something second nature to digital natives: baring their most cringe-worthy moments for millions to see."
Rex Woodbury
A Guide to Gen Z Through TikTok Trends, Emojis, & Language
"status comes from being singular. If Millennials tried desperately to fit in, Gen Zs try desperately to stand out."
Rex Woodbury
A Guide to Gen Z Through TikTok Trends, Emojis, & Language
"McKinsey research concluded, “Gen Zers value individual expression and avoid labels.” This leads to new forms of consumption: consumption as access rather than possession, and consumption as an expression of individual identity."
Rex Woodbury
A Guide to Gen Z Through TikTok Trends, Emojis, & Language
"Gen Zs are genuine and forthright and singular. They don’t tolerate capping. They look down on cheugy. They bare their souls for the world to see and rely on the uniqueness of that soul (no matter how unsightly) to forge their own unique identities."
Rex Woodbury
A Guide to Gen Z Through TikTok Trends, Emojis, & Language
"Creative & Self-Expressive"
Rex Woodbury
A Guide to Gen Z Through TikTok Trends, Emojis, & Language
"over half (51%) say that Gen Z is more creative than previous generations."
Rex Woodbury
A Guide to Gen Z Through TikTok Trends, Emojis, & Language
"TikTok nurtures a culture of creativity by removing the friction to come up with ideas for content."
Rex Woodbury
A Guide to Gen Z Through TikTok Trends, Emojis, & Language
"The culture of creation on TikTok solves the cold-start problem."
Rex Woodbury
A Guide to Gen Z Through TikTok Trends, Emojis, & Language
"TikTok blows the 90-9-1 rule out of the water: 55% of TikTok users create content for the platform. Over time, the internet becomes more participatory; more people shift from consumer to creator."
Rex Woodbury
A Guide to Gen Z Through TikTok Trends, Emojis, & Language
"Stan culture is a way to find belonging. Stanning a creator becomes a form of self-expression."
Rex Woodbury
A Guide to Gen Z Through TikTok Trends, Emojis, & Language
"Pragmatic & Self-Directed"
Rex Woodbury
A Guide to Gen Z Through TikTok Trends, Emojis, & Language
"A 2020 study found that 54% of Gen Zs want to start their own company; 89% have considered an education path that looks different than college. A Gallup poll found that 77% of young people in grades 5 through 12 want to be their own boss. The main reasons cited are autonomy and flexibility."
Rex Woodbury
A Guide to Gen Z Through TikTok Trends, Emojis, & Language
"As Gen Z comes of age, work disaggregates. America will become a majority-freelance economy by 2026. Many young people aspire to be creators because they want autonomy and flexibility. They’ve spent their lives looking at the “rigged” system and going 👁👄👁 . Entrepreneurship is a way to reclaim lost agency."
Rex Woodbury
A Guide to Gen Z Through TikTok Trends, Emojis, & Language
"Gen Zs have no choice: they bare their souls online, rely on the internet for creative self-expression, and turn to digital realms for work."
Rex Woodbury
A Guide to Gen Z Through TikTok Trends, Emojis, & Language
"For thousands of years, humans lived in tribes that defined kinship not as something biological, but as something you create."
Rex Woodbury
Digital Kinship: How the Internet Is Reacting to the Loneliness Epidemic
"Today, people have fewer places to congregate, converse, and find belonging."
Rex Woodbury
Digital Kinship: How the Internet Is Reacting to the Loneliness Epidemic
"Research has shown that “third places”—communal gathering spots that aren’t your home or office—are critical to social connection."
Rex Woodbury
Digital Kinship: How the Internet Is Reacting to the Loneliness Epidemic
"A recent survey found that nearly half of Americans always or sometimes feel alone (46%) or left out (47%). Over half—54%—feel that no one knows them well. Across the Atlantic, half of Brits over 65 consider the television or a pet to be their main source of company."
Rex Woodbury
Digital Kinship: How the Internet Is Reacting to the Loneliness Epidemic
"From 1970 to 2012, the share of households consisting of married couples with kids was cut in half. Single-person households rose from 13% to 28%. A century ago, 75% of Americans older than 65 lived with relatives; by 1990, only 18% did."
Rex Woodbury
Digital Kinship: How the Internet Is Reacting to the Loneliness Epidemic
"If the last 50 years saw a shift to the individual, the next 50 will see a shift to the collective—and digital connections will be the driving force of that sea change."
Rex Woodbury
Digital Kinship: How the Internet Is Reacting to the Loneliness Epidemic
"Social eating and livestream sleeping both reflect the internet’s shift to authenticity and always-on creation / consumption. The lines between the physical and digital dissolve, and online friends become as important as real-world friends."
Rex Woodbury
Digital Kinship: How the Internet Is Reacting to the Loneliness Epidemic
"Relatability has become the heart of a creator’s appeal, a far cry from the aspiration and elusiveness desired in celebrities of past eras"
Rex Woodbury
Digital Kinship: How the Internet Is Reacting to the Loneliness Epidemic
"every consumer company is built on a few core human needs, and those needs don’t change much over time."
Rex Woodbury
Digital Kinship: How the Internet Is Reacting to the Loneliness Epidemic
"If the 2010s were about people’s need for “status” online—manifesting in curated Instagram feeds and filtered selfies—then the 2020s are about people’s need for “belonging”."
Rex Woodbury
Digital Kinship: How the Internet Is Reacting to the Loneliness Epidemic
"Bilibili is essentially a hub for interest-based communities. It originated as a place for anime enthusiasts, but has since expanded to music, dance, science, film, fashion, and more. Bilibili is built on a trifecta that elegantly captures the future of consumer internet companies: user-generated content, commerce, and community."
Rex Woodbury
Digital Kinship: How the Internet Is Reacting to the Loneliness Epidemic
"But what’s most unique about Bilibili is how engaged and retentive its communities are. Bilibili achieves this by building friction into community. In order to join a Bilibili community, users must pass a 100-question test."
Rex Woodbury
Digital Kinship: How the Internet Is Reacting to the Loneliness Epidemic
"Building in friction means that communities are comprised only of superfans; 80% of users retain after 12 months."
Rex Woodbury
Digital Kinship: How the Internet Is Reacting to the Loneliness Epidemic
"Every aspect of the economy is becoming more community-centric."
Rex Woodbury
Digital Kinship: How the Internet Is Reacting to the Loneliness Epidemic
"The best education companies, meanwhile, will build community into their product."
Rex Woodbury
Digital Kinship: How the Internet Is Reacting to the Loneliness Epidemic
"In every sector, people are clamoring for human interaction and meaningful connection. Pieces of the economy that have historically been solitary are instead emphasizing solidarity."
Rex Woodbury
Digital Kinship: How the Internet Is Reacting to the Loneliness Epidemic
"Friendship accounts for 60% of the difference in happiness between people, and studies have shown that one of the key markers for midlife satisfaction is being able to rattle off the names of a few close friends."
Rex Woodbury
Digital Kinship: How the Internet Is Reacting to the Loneliness Epidemic
"people will discover connections with strangers through AI-powered platforms like TikTok and Clubhouse. These are the platforms that connect us with strangers and that create communities around us that we didn’t even know we craved belonging to."
Rex Woodbury
Digital Kinship: How the Internet Is Reacting to the Loneliness Epidemic
"experts emphasize that a central component of a third-place social ecosystem is familiarity, but not intimacy."
Rex Woodbury
Digital Kinship: How the Internet Is Reacting to the Loneliness Epidemic
"The best internet companies will be built to help people discover and nurture these online relationships."
Rex Woodbury
Digital Kinship: How the Internet Is Reacting to the Loneliness Epidemic
"Company B is YouTube and Company A is Netflix. They are the two leading content platforms in the world, and both companies did about $30 billion in revenue last year. But they did so with dramatically different business models."
Rex Woodbury
The Long Tail: The Internet and the Business of Niche
"YouTube pays creators 55% of advertising revenue, which is effectively its cost of content."
Rex Woodbury
The Long Tail: The Internet and the Business of Niche
"The concept of the long tail was popularized by Chris Anderson in an October 2004 article in WIRED. Anderson’s opening lines read like a prophecy of YouTube, which would be founded the following year:"
Rex Woodbury
The Long Tail: The Internet and the Business of Niche
"“There is not that much talent in the world. There are very few people in very few closets in very few rooms that are really talented and can’t get out."
Rex Woodbury
The Long Tail: The Internet and the Business of Niche
"People with talent and expertise at making entertainment products are not going to be displaced by 1,800 people coming up with their videos that they think are going to have an appeal.”"
Rex Woodbury
The Long Tail: The Internet and the Business of Niche
"The concept of the long tail remains one of the best investing frameworks for internet companies."
Rex Woodbury
The Long Tail: The Internet and the Business of Niche
"Many of the most successful technology companies in history have been built on the long tail."
Rex Woodbury
The Long Tail: The Internet and the Business of Niche
"Google and Facebook turn to small businesses for the lion’s share of their advertising revenue."
Rex Woodbury
The Long Tail: The Internet and the Business of Niche
"What’s really amazing about the Long Tail is the sheer size of it. Combine enough non-hits on the Long Tail and you’ve got a market bigger than the hits."
Rex Woodbury
The Long Tail: The Internet and the Business of Niche
"Spotify, founded in 2006, built its business on expanding music to effectively infinite selection."
Rex Woodbury
The Long Tail: The Internet and the Business of Niche
"But for long tail companies to succeed, they need to ensure that niche products are in stock when you need them;"
Rex Woodbury
The Long Tail: The Internet and the Business of Niche
"This is why companies like Amazon have best-in-class inventory management systems."
Rex Woodbury
The Long Tail: The Internet and the Business of Niche
"As egalitarian as Wal-Mart may seem, it is actually extraordinarily elitist. Wal-Mart must sell at least 100,000 copies of a CD to cover its retail overhead and make a sufficient profit"
Rex Woodbury
The Long Tail: The Internet and the Business of Niche
"When the crowd gets to vote with dollars and eyeballs, new forms of content and commerce suddenly become popular."
Rex Woodbury
The Long Tail: The Internet and the Business of Niche
"Over the past two decades, “Data is the new oil” has become an oft-used refrain in tech."
Rex Woodbury
The Long Tail: The Internet and the Business of Niche
"Recommendations have become a massive part of the successful long-tail companies."
Rex Woodbury
The Long Tail: The Internet and the Business of Niche
"TikTok is the best modern extension of this framework. Building on the concept of recommendations, TikTok’s For You Page is entirely algorithmically-generated, tailor-made to the user’s tastes and preferences."
Rex Woodbury
The Long Tail: The Internet and the Business of Niche
"As creation gets even easier, the long tail will continue to lengthen. Innovations like Midjourney, DALL-E, and StableDiffusion—which provide text to image AI generation—may unlock new levels of creativity and expression."
Rex Woodbury
The Long Tail: The Internet and the Business of Niche
"Shopify is built on the long tail—on serving the many, many small merchants out there that comprise the lion’s share of global retail."
Rex Woodbury
The Long Tail: The Internet and the Business of Niche
"Openstore then streamlines your operations and grows your brand."
Rex Woodbury
The Long Tail: The Internet and the Business of Niche
"Pietra makes it easier to launch a digitally-native product line, abstracting away the complexities of manufacturing, inventory management, and fulfillment."
Rex Woodbury
The Long Tail: The Internet and the Business of Niche
"Another example of a modern startup building for the long tail is Faire. Faire is a B2B marketplace that connects brands and wholesale retailers."
Rex Woodbury
The Long Tail: The Internet and the Business of Niche
"Faire hits on the key components of long tail businesses: Faire improves selection by giving retailers a much greater variety of potential brands to choose from, and vice versa."
Rex Woodbury
The Long Tail: The Internet and the Business of Niche
"My friend Chris Paik calls this “off-balance sheet operating leverage.” Can a company enable an entire ecosystem to form on top of it?"
Rex Woodbury
The Long Tail: The Internet and the Business of Niche
"The seven deadly sins are a classification of our most fundamental vices—the negative personal characteristics that are human nature, and that we all find ourselves subject to. The origin of the seven deadly sins can be traced back to Christianity in Ancient Egypt, and the list has been refined over the centuries."
Rex Woodbury
The Seven Deadly Sins of Consumer Technology
"Seven pushed the seven deadly sins back into our pop culture vernacular, beyond religious confines. And in the years since, the seven deadly sins have become part of our tech vocabulary too."
Rex Woodbury
The Seven Deadly Sins of Consumer Technology
"In 2011, Reid Hoffman declared, “Social networks do best when they tap into one of the seven deadly sins.”"
Rex Woodbury
The Seven Deadly Sins of Consumer Technology
"I would expand Hoffman’s statement to encompass consumer companies writ large. And I like his framework because it captures a key truth: human behavior is the engine of consumerism, capitalism, and culture."
Rex Woodbury
The Seven Deadly Sins of Consumer Technology
"but we’re all fundamentally the same, shaped by millions of years of evolution: we all get angry; we all get jealous; we all need to feel respected."
Rex Woodbury
The Seven Deadly Sins of Consumer Technology
"They are conduits for human communication, which runs the full spectrum of emotion. Both the good and the bad fuel network growth."
Rex Woodbury
The Seven Deadly Sins of Consumer Technology
"LinkedIn personifies Pride."
Rex Woodbury
The Seven Deadly Sins of Consumer Technology
"In the early days of the company, LinkedIn’s founders were surprised to find that, curiously, there was one profile that people seemed to visit far more than any other: their own."
Rex Woodbury
The Seven Deadly Sins of Consumer Technology
"It turns out that people love to curate and admire their own achievements."
Rex Woodbury
The Seven Deadly Sins of Consumer Technology
"And the network has given birth to the (*shudder*) LinkedIn influencer."
Rex Woodbury
The Seven Deadly Sins of Consumer Technology
"Gen Zs view LinkedIn as a cringeworthy, out-of-touch place for older internet users to subtly (or not-so-subtly) humblebrag."
Rex Woodbury
The Seven Deadly Sins of Consumer Technology
"But it turns out that LinkedIn has uniquely strong network effects, with millions of job-seekers and recruiters building their professional bedrock with the site."
Rex Woodbury
The Seven Deadly Sins of Consumer Technology
"And there are other examples of Pride beyond work—particularly companies that allow users to showcase achievements or make a “flex” in their profile."
Rex Woodbury
The Seven Deadly Sins of Consumer Technology
"But there’s one social network that is deceptively reliant on Pride: Strava. Strava lets athletes show off how far they biked or how far they ran."
Rex Woodbury
The Seven Deadly Sins of Consumer Technology
"No company has better captured Sloth in the past decade than Netflix."
Rex Woodbury
The Seven Deadly Sins of Consumer Technology
"There are many other examples of Sloth: hiring someone on TaskRabbit to assemble your IKEA furniture; turning to Instacart for getting your groceries; becoming so accustomed to Amazon’s speed that even a two-day delivery begins to feel unacceptable."
Rex Woodbury
The Seven Deadly Sins of Consumer Technology
"But the sector that best captures Sloth in 2022 is gaming. Gaming is a larger industry than fellow Sloth industries like movies and TV combined."
Rex Woodbury
The Seven Deadly Sins of Consumer Technology
"And the premise of the metaverse is inherently sloth-like: our bodies remain motionless in the analog world while our minds explore virtual worlds."
Rex Woodbury
The Seven Deadly Sins of Consumer Technology
"Comparison is the root of Envy, and social media is built on comparison."
Rex Woodbury
The Seven Deadly Sins of Consumer Technology
"Instagram disruptors like BeReal, Poparazzi, Dispo, and Locket have promised a more authentic, less curated reality. But even authenticity, over time, becomes performative;"
Rex Woodbury
The Seven Deadly Sins of Consumer Technology
"Crypto wallets and virtual showrooms like Decentraland are the best modern example of Envy."
Rex Woodbury
The Seven Deadly Sins of Consumer Technology
"A decade ago, Greed was signified by the rise of investing apps"
Rex Woodbury
The Seven Deadly Sins of Consumer Technology
"When Reid Hoffman mentioned the seven deadly sins 11 years ago, he used GrubHub as the example for Gluttony."
Rex Woodbury
The Seven Deadly Sins of Consumer Technology
"Snackpass is a social takeout app that lets you order ahead and pick up food—sort of like the Starbucks app, but for every restaurant. Snackpass gamifies food by letting you earn reward points and then gift free things to friends"
Rex Woodbury
The Seven Deadly Sins of Consumer Technology
"Tinder is the canonical example of Lust. The company built its name on looks-based dating, with rapid swiping based only on a photo."
Rex Woodbury
The Seven Deadly Sins of Consumer Technology
"Grindr, the gay chat app, averages 61 minutes of engagement every day—equivalent to Facebook and Instagram combined."
Rex Woodbury
The Seven Deadly Sins of Consumer Technology
"As the old maxim says, sex sells"
Rex Woodbury
The Seven Deadly Sins of Consumer Technology
"It seems capitalism slowly works its way up Maslow’s hierarchy of needs, and we’ve hit the Love & Belonging rung of the ladder with dating apps, paid communities, and fan subscription services."
Rex Woodbury
The Seven Deadly Sins of Consumer Technology
"Sex sells. Lust sells. And Lust is powering one of the most successful creator platforms."
Rex Woodbury
The Seven Deadly Sins of Consumer Technology
"Wrath, according to Dante, was a twin sin to sullenness. He wrote that they both came from the same essential error"
Rex Woodbury
The Seven Deadly Sins of Consumer Technology
"Wrath is rage expressed, sullenness is rage unexpressed."
Rex Woodbury
The Seven Deadly Sins of Consumer Technology
"Twitter has always been about Wrath. Everyone on Twitter always seems…angry."
Rex Woodbury
The Seven Deadly Sins of Consumer Technology
"Review-based apps like Yelp also rely heavily on Wrath; some people even lose their jobs for being overly angry on Yelp."
Rex Woodbury
The Seven Deadly Sins of Consumer Technology
"Fox News, meanwhile, has turned Wrath into its entire business model."
Rex Woodbury
The Seven Deadly Sins of Consumer Technology
"DoNotPay offers you a “robot lawyer” that lets you sue anyone at the press of a button. Think of all the things that make you really, really mad—lawsuit mad. Parking tickets. Malicious landlords. Identity theft. Airline cancellations. Insurance claims. DoNotPay has built a surprisingly large business on helping you solve all of them."
Rex Woodbury
The Seven Deadly Sins of Consumer Technology
"Theologians often recognize two other sins, beyond the initial seven."
Rex Woodbury
The Seven Deadly Sins of Consumer Technology
"The first is Vanity, which has close ties to Envy. Instagram (and any social network, particularly visual-based social networks) could also be attributed to Vanity."
Rex Woodbury
The Seven Deadly Sins of Consumer Technology
"Though perhaps the best example of Vanity is Lightricks, the maker of the editing app Facetune."
Rex Woodbury
The Seven Deadly Sins of Consumer Technology
"The second additional sin—“the 9th sin”—is Acedia, a word which has faded from our vocabulary. Acedia is effectively apathy or listlessness, “not caring or not being concerned with one's position or condition in the world.”"
Rex Woodbury
The Seven Deadly Sins of Consumer Technology
"(Side note: Lensa is a classic example of a product tapping into people’s vanity, and harks back to last year’s Digital Native piece The Seven Deadly Sins of Consumer Technology.)"
Rex Woodbury
AI in 2023: The Application Layer Has Arrived
"What’s exciting about AI right now is that the platform layer is solidifying, meaning that it’s time for the application layer to emerge."
Rex Woodbury
AI in 2023: The Application Layer Has Arrived
"One of the fascinating aspects of living in 2023—and one of the guiding themes for Digital Native—is the fact that our brains are no different than they were a century ago (evolution, it turns out, takes a long time), yet our world has changed dramatically in 100 years."
Rex Woodbury
AI in 2023: The Application Layer Has Arrived
"Over the past decade, two primary forces have powered technology: mobile and cloud."
Rex Woodbury
AI in 2023: The Application Layer Has Arrived
"Mobile facilitated the rise of large consumer internet companies"
Rex Woodbury
AI in 2023: The Application Layer Has Arrived
"Digital advertising rapidly shifted to mobile in the 2010s, and desktop-era companies like Facebook had to scramble to reinvent their businesses."
Rex Woodbury
AI in 2023: The Application Layer Has Arrived
"Cloud, for its part, underpinned an explosion in software-as-a-service (SaaS) and enabled data to become the most prized resource in a business (“Data is the new oil” and all that)."
Rex Woodbury
AI in 2023: The Application Layer Has Arrived
"Mobile and cloud made the 2010s a very, very good decade in technology."
Rex Woodbury
AI in 2023: The Application Layer Has Arrived
"Perhaps the most compelling—and most likely—force to power tech in the 2020s is artificial intelligence."
Rex Woodbury
AI in 2023: The Application Layer Has Arrived
"Why swipe endlessly on Tinder when AI can surface your perfect match?"
Rex Woodbury
AI in 2023: The Application Layer Has Arrived
"In June, SHEIN dethroned Amazon as the No. 1 shopping app in the iOS and Android app stores."
Rex Woodbury
AI in 2023: The Application Layer Has Arrived
"SHEIN combs competitor’s websites and Google Trends to figure out what’s in style, then quickly makes its own designs, forecasts demand, and adjusts inventory in real-time."
Rex Woodbury
AI in 2023: The Application Layer Has Arrived
"All of a sudden, a “1-on-1” experience is replicable at scale—and today’s AI applications are still rudimentary compared to those we’ll see in the coming years."
Rex Woodbury
AI in 2023: The Application Layer Has Arrived
"People tend to prefer richer media formats: Instagram (primarily photos) has always been more popular than Twitter (primarily text); TikTok (primarily videos), meanwhile, has been eating away at Instagram usage, forcing the latter to pivot to video with Reels."
Rex Woodbury
AI in 2023: The Application Layer Has Arrived
"The same preferences, in my mind, will hold true for generative AI: images > text, soon video > images, and eventually immersive 3D experiences > video."
Rex Woodbury
AI in 2023: The Application Layer Has Arrived
"To get technical, Stable Diffusion moved diffusion from the pixel space to the latent space, driving a profound increase in quality."
Rex Woodbury
AI in 2023: The Application Layer Has Arrived
"Last year was a tipping point for image models, with rapid improvements in quality."
Rex Woodbury
AI in 2023: The Application Layer Has Arrived
"One example: famously, AI is bad at making hands. It’s very difficult to know how many fingers have already been made unless the AI has an excellent sense of context."
Rex Woodbury
AI in 2023: The Application Layer Has Arrived
"One of the reasons that Mickey Mouse wears gloves is that it made for much faster animation; hands are difficult to draw."
Rex Woodbury
AI in 2023: The Application Layer Has Arrived
"The same goes for Fred Flintstone and George Jetson—neither has a visible neck, because allowing for a neck meant that a character’s entire body needed to shift with each movement and expression. That meant a lot more work for the animator. A necktie and a high collar offered tricks for animators to speed up production."
Rex Woodbury
AI in 2023: The Application Layer Has Arrived
"Finding Nemo was in some ways an excuse for Pixar to show that it could animate realistic water."
Rex Woodbury
AI in 2023: The Application Layer Has Arrived
"Pixar waited until The Incredibles, its 6th feature film, to tell its first story about humans because CGI technology hadn’t previously been ready (part of the reason Toy Story focused on toys was because Pixar couldn’t yet render detailed humans—you barely see Andy and his mom in the film)."
Rex Woodbury
AI in 2023: The Application Layer Has Arrived
"In the Black Mirror episode “Be Right Back”, a husband and wife move into a new home together. The next day, the husband is killed in a car accident. His widow learns of a new service that lets you chat with your deceased lover; the tool digests text messages and social media history to learn how your partner would have responded, and then chats with you in his place."
Rex Woodbury
AI in 2023: The Application Layer Has Arrived
"Each new model makes leaps forward in its ability to come up with new ideas, understand context, and recall information."
Rex Woodbury
AI in 2023: The Application Layer Has Arrived
"But larger models are also much, much more expensive to train. Training a model with hundreds of billions of parameters can cost millions of dollars."
Rex Woodbury
AI in 2023: The Application Layer Has Arrived
"One of the earliest forms of AI was handwriting recognition, used primarily by the postal service to read addresses on envelopes."
Rex Woodbury
AI in 2023: The Application Layer Has Arrived
"When it comes to generative AI, we’ve seen: 1) massive improvements in image and language models, and 2) valuable infrastructure provided by companies like OpenAI, Hugging Face, and Stability.ai."
Rex Woodbury
AI in 2023: The Application Layer Has Arrived
"The cost of consuming culture may have declined, though not as much as we feared. But the cost of producing it has dropped far more drastically."
Rex Woodbury
AI in 2023: The Application Layer Has Arrived
"YouTube was revolutionary, but left barriers to creation: 1) the money to invest in expensive tools, and 2) the knowledge of how to use those tools."
Rex Woodbury
AI in 2023: The Application Layer Has Arrived
"TikTok removed those barriers with no-code-like tools, leveling the playing field. The result is that 1 in ~1,000 people on YouTube create content, while closer to 60% of TikTok users create."
Rex Woodbury
AI in 2023: The Application Layer Has Arrived
"Just as AI amplifies creativity, AI amplifies productivity."
Rex Woodbury
AI in 2023: The Application Layer Has Arrived
"More complex tasks (3D game creation comes to mind) will come further down the road. But any industry that involves human creation (read: basically every industry) will feel the effects of AI."
Rex Woodbury
AI in 2023: The Application Layer Has Arrived
"A looming question mark is how companies will build competitive moats;"
Rex Woodbury
AI in 2023: The Application Layer Has Arrived
"true tech differentiation is rare, and companies will need to find ways to stay ahead of competition, perhaps with network effects or with iterative loops of user engagement and product refinement."
Rex Woodbury
AI in 2023: The Application Layer Has Arrived
"Software-as-a-Service is a beautiful thing. Predictable, recurring revenue. 80%+ gross margins."
Rex Woodbury
AI in 2023: The Application Layer Has Arrived
"Ideally net dollar retention >100%, meaning that even without acquiring any new customers, your business steadily grows year-over-year."
Rex Woodbury
AI in 2023: The Application Layer Has Arrived
"My hunch is that many of the best AI startups will be SaaS companies. Why change a good thing?"
Rex Woodbury
AI in 2023: The Application Layer Has Arrived
"The challenge with Lensa, of course, is defensibility; Lensa lives on top of Instagram, Twitter, and TikTok and will have to figure out how to develop a moat."
Rex Woodbury
AI in 2023: The Application Layer Has Arrived
"One creative new company building with a familiar business model is PromptBase"
Rex Woodbury
AI in 2023: The Application Layer Has Arrived
"PromptBase is a marketplace for text-to-image prompts—likely one of the first marketplaces in generative AI. It’s surprisingly difficult to come up with the right prompt to produce a stunning piece of AI art."
Rex Woodbury
AI in 2023: The Application Layer Has Arrived
"PromptBase sells access to such long, highly-specific prompts. The marketplace has 11,000 users so far."
Rex Woodbury
AI in 2023: The Application Layer Has Arrived
"There will be ad-driven social networks, micropayment-driven MMOs, usage-based pricing."
Rex Woodbury
AI in 2023: The Application Layer Has Arrived
"When a technology changes how a broad range of goods or services are produced, it’s called a “general-purpose technology.”"
Rex Woodbury
AI in 2023: The Application Layer Has Arrived
"1) the Agricultural Revolution, which gave us food production at scale and let us transition from hunting and gathering to farming"
Rex Woodbury
AI in 2023: The Application Layer Has Arrived
"2) the Industrial Revolution, which gave us manufacturing at scale. I’d argue that the onset of the internet—the Digital Revolution—marked a third. But I also agree with them that Transformative AI is the next general-purpose technology:"
Rex Woodbury
AI in 2023: The Application Layer Has Arrived

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