The state of VC in 2023
Where we are, where we are going, and where to invest

‘Calendly’ Etiquette is The Most Raw / Naked Display of Social Capital Dynamics in Business.
A classic

The coming fall of the Kardashians
In context of how entertainment is evolving… (AKA why they are so pissed about tiktok)

The Fundamental Rationality of Young People Engaged in Yolo Capitalism
If you can’t earn your way into ‘the good life’ you might as well put it all on black…]

It is nearly impossible to convince a VC of a thesis they don’t already believe
So the key in fundraising is to ‘discover’ the right partners, not try to educate and convince…

The Power and Scale of The Crypto ‘Self-Tenured’ Class…
The random wealth effect has some positives and negatives.

People who believe in ‘citizen journalism’ fundamentally don’t understand is that the ‘cost’ of real information is very high.
Finding new facts, and validating their truth, and carrying liability is structurally much more costly than citizens can afford alone.

The Long-Term Implications of Extended Work From Home (2020-04-30)
The trend toward remote work may have been underway already, but in the last several weeks the Covid-19 crisis has forced companies to fully commit to the necessary investments in tech, process and training to make remote work a permanent feature of their businesses. Companies won’t go back to the pre-coronavirus office culture.

On Bots, Conversational Apps and Fin (2016-01-18)
The shift around software distribution towards conversational interfaces represents a major point of disruption for platforms and will likely be good news for developers. The many-billion-dollar question, however, is whether the transition to bots and conversational interfaces will represent a major point of disruption or more of an evolution in the interface paradigm.

Why Startups Are Doomed, Part Two (2016-02-08)
The rise of marketplace businesses has made bigger businesses more efficient, not less, which is bad news for startups. . Before modern technology, the idea that one company could dominate such a fundamental activity would have been absurd because we believed that things became less efficient when they got bigger.

The ‘Uber Effect’ on the Property Market (2014-09-15)
Jared mentioned that because of Lyft and Uber he now regularly goes to restaurants across the city that would once have been too far away to consideIf he’s an early indication, the importance of walkability for businesses like restaurants is probably going to change as well.

The End of Venture Capital as We Know It (2021-08-04)
Silicon Valley VCs are at a structural capital disadvantage in private tech - Seed investing may be immune—for now - High-reward investment opportunities still exist but move fast

The Tower of Babel: Five Challenges of the Modern Internet (2017-11-06)
• Consolidation of speech platforms poses risks. Current internet is biased toward extreme speech. Choices loom about prioritizing freedom vs. security. If we decide that anyone should be able to reach everyone, then we need to be willing to tolerate a lot of painful speech.

Creator Financing Is Going Mainstream (2022-12-29)
What a difference a year makes…

From Theranos to FTX: Silicon Valley’s ‘No Additional Work Required’ Late-Stage VC Culture and What to Do About It (2022-11-02)
here is why Silicon Valley has a problem investing in late-stage deals that turn out to be fraudulent.

Elon Musk Is Silicon Valley’s New Hero—for Better or Worse (2022-04-26)
Elon does not fit the classic hero’s archetype, but he’s a better reflection of today’s Silicon Valley than the mythical entrepreneurs of old.

How to Put Physical Assets on the Blockchain (2022-02-24)
The solution to a complex problem like bringing physical assets onto the blockchain doesn’t have to be elaborate—in fact, it should be boring.

Facebook’s Decade-Old Missteps Should Be a Lesson for Web3 (2021-12-02)
Decentralization won’t be enough to create a truly open web if the information shared between apps isn’t useful or if the economics of openness don’t make sense.

The Metaverse Is Coming. What Happens Next? (2021-11-12)
The metaverse isn’t one thing—it’s the intersection of three distinct and parallel revolutions. By now it’s clear we’ll move from one universe to many, but it’s far too early to tell how these worlds will interact.

Investing Directly in People Is the Future of VC. Here’s How to Do It. (2021-11-05)
Unless young people can leverage their natural equity value, we’ll forever be at the mercy of the olds.

What Sequoia Gains by Blowing Up the VC Fund Structure (2021-10-27)
Sequoia’s move to create one big, open-ended fund gives the firm a slew of new advantages—and will make it much harder for some hedge funds and private equity firms to compete.

‘MrBeast’ Explains His Plans to Help YouTube Creators Raise Equity Finance (2021-03-24)
A Q&A with Jimmy Donaldson, one of the most popular creators on YouTube under the name “MrBeast,” about his new company aimed at helping YouTube creators raise equity finance.

The Future of Investing Directly In People (2021-03-22)
Equity-based financing for individuals is about to go mainstream and will be particularly valuable for creators and influencers. There are already examples of this model, such as the income insurance pools that some minor-league baseball players rely on and the income share agreements that some students use. But to ensure that these models are equitable and safe, we need to build some guardrails.

Collectibles, Crypto NFTs, and the Monetization of Influence (2021-03-2)
The explosion of interest in NFTs reflect technology’s impact on how we value assets, including the influence of cult leaders on investments. NFTs aren’t about art, but good investors should take them seriously.

Clubhouse and the Future of Cult-Driven Social Platforms (2021-02-18)
Clubhouse’s rise is due to its success in harnessing the movement toward cults and away from communities on the internet. That signals a challenge for older social platforms and raises a question of how communities can regain power in the future.

Equity Financing for Influencers (2021-01-26)
Influencers are positioned to become the most valuable brands of the future, replacing corporate brands. But to guarantee that shift, influencers need to sell equity just as a business would do, giving investors a share of their lifetime earnings. That would give them more access to the capital and talent they need to grow.

How Blocking Trump Puts the Future of the Internet at Risk (2021-01-12)
While Facebook and Twitter made the right call in blocking Trump, the decisions could snowball us towards the collapse of the global internet as we know it, columnist Sam Lessin writes. The way we end up with true global dictatorship and authoritarian regimes is by using modern technology to monitor, censor and control private speech.

How Covid Accelerated Changes Already in the Making (2020-12-22)
Covid-19 intensified trends that were developing before the pandemic, such as broad income inequality, stricter regulation of tech behemoths and geographic shifts away from tech hubs like San Francisco. But the crisis won’t fundamentally alter our long-term trajectory, columnist Sam Lessin writes.

The Societal Problem of Only Needing 1,000 True Fans to Be Successful Online (2020-11-11)
The internet is pushing people to find and cultivate increasingly extreme niche communities, which is causing a fragmentation of our society, making it harder for us to deal with broad-spectrum challenges—Covid-19, for example. It is time to find a way to bring back the better aspects of collective identity and purpose.

How to Prevent Social Media’s Editorial Role From Becoming Censorship of Speech (2020-10-20)
By forcing social media outlets to act as fact-checkers and editors, we have opened the door to broad long-term government oversight of private speech. Most communication today occurs in private spaces rather than on social media’s news feeds, and the discussion about controls will naturally and subtly shift from public to private spaces. There are several key things platforms should do to prevent this, including giving users explicit rights over the private spaces they create and use.

Lessons From the Rise of OnlyFans (2020-10-02)
Adult-entertainment subscription platform OnlyFans offers several lessons about the future of digital content monetization. Creators use social media to find people willing to pay. And once people start paying, OnlyFans finds ways to get more money out of them.

California’s 2020 Budget Solution: A Startup Equity Tax (2020-08-31)
Unlike higher income taxes or a wealth tax, a 5% tax on the equity of Bay Area startups would ease California’s immediate budget crisis and position the state for long-term success, columnist Sam Lessin writes.

Why Instagram’s Reels Rollout Will Slow, but Not Stop, TikTok’s Growth (2020-08-10)
The launch of Instagram’s Reels will test whether TikTok’s success can be easily copied. Columnist Sam Lessin delves into the challenges the new app faces.

The Simple and Practical Steps the Federal Government Should Take to Fix Online Speech (2020-07-21)
To fix some of the problems related to online speech and identity, the government could start issuing digital federal IDs, perhaps connected with the issue of passports, that social networks could use to validate the identity of users. Such a system shouldn’t be mandatory, but people who want to make their voices heard online would likely opt to use it

The Escalating War Between Our Physical and Digital Realities (2020-07-15)
The physical world and the digital worlds are increasingly in conflict—a clash lately exacerbated by Covid-19, which has increased the value of the digital realm in people’s lives. The two worlds are fundamentally incompatible. Resolving conflict between them is impossible, which will make it harder for people to coexist in both worlds.

On Feed Ranking and Free Speech (2020-06-22)
Personally ranked feeds (like Facebook’s News Feed) need to be understood as a key part of modern communications infrastructure. It is wrong to conflate them with traditional publishing, and dangerous to push them to editorialize. You can’t claim to believe in free speech and not believe also in the freedom to choose whom to follow and what to listen to

The Slippery Slope to Censored Speech (2020-06-08)
The push for social networks to moderate speech could jeopardize what we are able to say in private, because technology has eliminated the distinctions between what is private and what is public speech. And technology has unlocked the power to monitor and limit what people say in private to each otheTo avoid an otherwise inevitable crisis, we need new technical tools, new explicit rights and broad media education

The Over-Under on New Voice-Chat App Clubhouse (2020-06-01)
Clubhouse’s recent fundraising reflected strong interest among Silicon Valley insiders in the app’s potential to create a popular new network reflecting conversations between people that are more authentic than existing social media. But Clubhouse faces several hurdles, and it is unclear whether it will capture the value inherent in the powerful underlying idea

How Covid-19 Is Changing Seed Companies and Financing in Silicon Valley (2020-05-20)
Covid-19 and the accompanying economic downturn will affect startups in numerous ways. Early-stage valuations are falling, investors are demanding stronger protections, and angel investors might find it harder to compete. But there are more opportunities for startups in areas like social media and working from home. Early investors worry that even if companies hit their milestones, there might not be capital available at attractive prices.

How Google and Apple Need to Play the Covid Contact Tracing Debate’s Next Phase (2020-05-06)
Google and Apple have done a masterful job of managing the technology and policy around contact tracing technology—prioritizing privacy while proactively offering new functionality to help save lives. But the next phrase presents challenges that will be harder for the companies to deal with, as different countries look to reopen their economies and want to balance privacy and safety differently

Technology’s Role in Shaping the Impact of Covid-19 (2020-04-06)
Technology and the internet has positioned the U.S. to deal with Covid-19 much better than we could have in the past. We can retool factories and supply chains faster to produce urgently needed tests and supplies. We have the technology to enact more-complete isolation at home while still keeping many people working, learning and entertained. And we can better deliver aid to people and businesses to manage the economy than we ever could before. With a few more decades of technological development, however, we would be even better positioned.

How Coronavirus Epidemics Could Alter the Future of Tech (2020-03-09)
Today’s improved communications and knowledge, ironically, magnify the impact of the coronavirus. Long term, it may enhance the position of the biggest companies, deepen social inequality and strengthen the power of the state.

The 10 Ways TikTok Will Change Social Product Design (2020-02-10)
TikTok’s innovations, from consumption-first onboarding to integrated feeds to social content creation, are destined to influence social network design, writes columnist Sam Lessin. TikTok is darn close to zero work to consume. Your only option is to skip a thing when you get bored of it.

My Predictions for the Next Decade (2020-01-14)
I lay out my predictions for the next decade, looking at big-picture social challenges, how regulation will affect big tech, personal technology use, the economy and cryptocurrency.

Grading My 2010 Predictions—and What I Learned (2020-01-14)
I looked back at my 2010 predictions about the past decade to see what I got right—and wrong. I correctly forecast that the rise of privacy would be a big tech issue and that Facebook and Amazon would become antitrust targets. But I was wrong to think that dominant services of 10 years ago, like Google, would become commoditized. And I missed how the economy would recover from the 2008 financial crisis.

In Defense of Deep Fakes (2019-12-16)
While there are increasing worries about deep fake technology destroying trust in the media and our sense of reality, distributing the powerful technology widely may be healthier than attempting to limit it. Deep fake technology can help us protect our privacy and may help people differentiate between fantasy and reality

Four Paths Forward for ‘Social Products’ (2019-12-02)
Investors and founders are starting to explore a new generation of social products that follow one of several paths. Some leverage the physical world, some focus on content moderation and truth, while others invent new content formats. It’s a sign that in the future people are going to engage with many more social products than they do today

The Key Themes That Matter for the Future of Work (2019-11-04)
The future of work has recently become one of the hottest themes in the venture capital community, and a wide range of technologies, services and companies are all positioning themselves as part of the theme. A few key first principles elucidate where the biggest opportunities will be.

The Challenges Facing Free Speech (2019-10-22)
Mark Zuckerberg did a good job explaining the challenges of free speech and how Facebook approaches the issue. But because of the impact that technology has on speech, I think there are more complex issues. We are moving from a world of trusting speech by default to distrusting speech by default.‘There is a deeper set of technology-driven issues we need to bear in mind when we as a society think of speech and “rule-setting” around expression.’

The Home Camera Wars (2019-09-24)
The key factor in major tech companies’ battle for control of the home is turning out to be cameras, not screens. Each of the major platforms has extended their service with cameras into the home, and is trying to leverage their area of strength into adjacent rings of integrated services.

A Solution for Gig Economy Labor: Lightning Strikes (2019-09-16)
Labor advocates representing workers at on-demand services like Uber and Lyft have to update their playbook for work actions. Instead of mass work stoppages, they should use lightning strikes targeted to individual areas, using data to pick spots that will have the maximum impact on the business.

On Inequality and Risk Capacity (2019-07-22)
The biggest factor causing inequality is the ability of people to take risk. Those who have already scored a big success have more capacity to take further risks than those who haven’t. Meanwhile, regulations are locking people out of opportunities that offer high returns.

The Future of Free Speech (2019-07-15)
My takeaways on news, technology and communication from a recent event on the future of free speech

Remote Work and the Politics of Decentralization (2019-05-06)
In the last 20 years technology has contributed to the resurgence of cities, but has under-delivered on expectations about seamless telecommuting. In the coming years, tech companies may shift to decentralizing their workforces, as a result of the high cost of major cities and enabled by technologies that make remote collaboration easieThis decentralization could have a dramatic impact on the electoral map and other social issues.

Why the Internet Could Help Small Businesses Regain Power (2019-04-22)
Big businesses have used technology to become more efficient, to the detriment of smaller competitors. But there is the potential for online technologies to develop, in areas around data measurement, liquidity of equity and training, that could swing the pendulum back by empowering small businesses

What Will Happen to the Social Wealth of Instagram Influencers as They Age? (2019-04-01)
Instagram is loosening the hold the entertainment ecosystem once had on celebrity. But will today’s influencers retain their social wealth if the dominant platform changes? Columnist Sam Lessin sees three ways things could play out.

The Cost and Risk of Regulations That Make Information ‘Own-able’ (2019-03-18)
The information economy is putting increasing pressure on the physical economy, creating lots of debates about ownership of data and privacy. But it would be dangerous to write regulations for the information economy that are based in the physical economy.As these two economies are brought into such direct competition it is understandable that people want to use laws and policy to resolve the tension between the two.

A Warning on the Dangers of Ephemeral Messaging (2019-03-08)
By moving toward full encryption, Facebook can help society guard against central governments trying to regulate people’s private communications. But the risk that messaging will become the forum for information warfare suggests that Facebook’s embrace of ephemeral messaging is a mistake. Records shouldn’t be kept centrally, but they should be kept somewhere.

ISAs and the Future of Securitization (2019-02-25)
The internet hasn’t led to as much innovation in finance as might have been expected. Instead, financial institutions have used the internet to gain scale. But lately there has been an explosion of ideas around giving individuals access to equity finance for their personal needs. One example is schools testing income-sharing agreements for paying back loans through income-based repayments

The Pressure on the News Industry Is a Symptom of Disempowerment (2019-02-11)
One interpretation of the history of news suggests that the current troubles affecting local newspapers is due to middle classes in smaller communities feeling disenfranchised, and questioning why they should value high-quality information.The reason that the elites always retreat to quality is that the truth of politics and economics matter to them and the decisions they need to make.

How to Introduce a Wealth Tax (2019-02-04)
The idea of a wealth tax holds interest for people in Silicon Valley. The biggest practical challenge is valuing people’s assets accurately—particularly private company equity. One solution is the creation of a registry of assets that would force people to publicly state a binding price at which they would sell their assets to others.The problem currently with any wealth tax concept is that most assets don’t have a clearly established market value.

How Political Content Fills the Void Left by Micro-Targeting (2019-01-21)
As advertising of consumer products has become more specialized thanks to the internet, it has tended to favor lucrative, high-end goods. That has left an opening for people trying to influence political outcomes to market to less affluent consumers, Sam Lessin writes.

What Technologists Can Learn From Religions (2018-12-24)
The history of Judaism and Catholicism can teach us about how crypto and social platforms could evolve, particularly around the relative strengths and weaknesses of centralization and decentralization.

My Predictions for Crypto in 2019 (2018-12-17)
Next year, I expect that pragmatism will propel much of the crypto ecosystem. More traditional financial assets like real estate will find their way onto blockchains, and a series of corporate airdrops on semi-decentralized platforms will dominate the narrative.

We Need Better Measures of Social and Environmental Impacts (2018-12-03)
Despite the apparent strength of the economy, the sweeping costs of eroding trust, shifting attention, and environmental damage caused by modern business are hard to measure—and have not been properly accounted forIt should be obvious to any thinking person that, when it comes to our planet, we have been improperly accounting for and under-pricing the impact on the environment.

Is Uber Cash a Crypto Play? (2018-11-12)
Uber might be better positioned than social networks to jump into cryptocurrency, and its launch of Uber Cash could be a way in. A move by Uber could solve several of crypto’s big problems on the path to mass adoption.The idea of creating a new form of natively digital ‘money’ that can lower the barriers to global transactions, open up faster technical innovation and in theory disrupt the banking industry is a tantalizing opportunity that has captivated many.

The Coming of the Human Knowledge-Work Cloud (2018-10-15)
Knowledge work is going to move to a model much like how cloud computing works today, backed by a combination of humans and machines, writes columnist Sam Lessin. It is an enormous missed opportunity that professionals spend upward of half their time on administrative tasks.

How the Internet Broke and What to Do About It (2018-09-04)
There are three possible ways to deal with the deep challenges of free speech on the internet. We will need to explicitly choose between giving near complete control of speech to the government, using new technology to guarantee complete freedom of speech or accepting permanent tension between governments, platforms and people

The Future of Privacy: Disinformation (2018-08-20)
The strategically correct way to react to modern technology and protect privacy in 2018 is to share lots of disinformation, burying the truth in a sea of lies instead of trying to protect the truth itself. But there are fundamental flaws in this as a long-term approach.

Scooters: The New Self-Driving Cars (2018-07-30)
E-scooters are a great mode of transportation for dense, urban areas, but it is hard to see how operators will make money, writes Sam Lessin.

It’s Time for an American Internet Privacy Framework (2018-06-19)
The U.S. needs to establish its own version of internet data law, rather than allow Europe to become America’s de facto regulator through a strange quirk of history, writes Sam Lessin.

Instagram Is the Real Virtual Reality, Not Oculus (2018-05-28)
Looking at the evolution of platforms like Instagram, it is increasingly clear that VR will be built through layers of fantasy built on top of reality. That could put stress on the real world, by making it harder for people to distinguish fantasy from reality.

Venmo Trust and The Blockchain (2018-05-08)
The next use case for blockchains could be serving as the backbone for a decentralized consumer trust network. Venmo originally tried to build a centralized version of this, but was forced to pivot away. Crypto might provide the fundamental technology to enable the disruption of consumer lending that Venmo originally attempted.This web of consumer trust would allow people to directly borrow potentially large sums of money from each other in aggregate by borrowing small amounts of money from many different people.

Governing the Internet (2018-04-09)
Technology has given us the ability for the first time to police nuanced issues around speech and information. We have abdicated decision-making to the big technology platforms, which are in an unwinnable position—forced to try to resolve big, complicated social questions. How do we move forward from here?. On one level I feel for the leadership teams at technology companies who have been left to try to sort out these issues on their own. They are in an unwinnable position.

The Double-Edged Sword of Using Blockchains for Identity Portability (2018-03-05)
Many technologists are excited about using blockchain to make identities portable on the internet, but it will likely come with strings attachedThis approach to portability risks leading us to a dystopic panopticon where your complete reputation follows you everywhere—whether you want it to or not.

The Intellectual Tension Between Social Networking and Blockchains (2018-02-12)
Usually we think of centralization and consistency going hand in hand. The same holds true of decentralization and nuance. But blockchains and social networks may be reversing those historical norms.If blockchain technology had been invented and deployed before social networking existed, would we be in the opposite position—decrying the forced consistency and lack of nuance of blockchain-based truth?

Stable Coins, Oracles, Trust, and Identity (2018-02-05)
Connecting the physical world to the digital world in a trusted way is a critical problem to solve in order to take advantage of many of the most exciting parts of new technologies like blockchains. But it is extremely hard to do even in the simplest of cases like price stabilized currencies.You might trust a single point of data for a low-risk fact. But for something that really matters, you would likely ask many trusted sources, apply your own logic, and then make a decision about what to believe.

Open vs. Closed in National Tech Strategies: the U.S. and China (2018-01-29)
The U.S. should centralize policy making in some key areas, like self-driving cars, but adopt a more open approach around capital raising. We don’t have the scale to succeed at the fully-closed strategy pursued by the Chinese.I don’t think any society can function at any scale with a fully open strategy, as much as many West Coast technologists would like to believe it possible.

The Future of Hybrid Centralized-Decentralized Apps (2018-01-15)
Blockchain-based services are designed to be more trustworthy than centralized models, but they are also less efficient and more expensive to run. That means companies have to figure out where it makes sense to use distributed services to build trust and where it doesn’t.The resource tax in running a secured decentralized service is the cost of security, not the cost of the transactions.

Blockchains and the Right to Be Forgotten (2017-12-18)
Blockchain technology challenges existing regulations governing content on the internet, rendering impractical the ‘right to be forgotten’ in EuropePhilosophically, the right to be forgotten is corrupt because it basically assaults a person or a company’s right to remember things.

14 Ways the Cryptocurrency Market Will Change in 2018 (2017-12-04)
• Bitcoin’s market share will grow, Sam Lessin predicts. Consumer use of crypto will remain limited. More healthy forks, fewer ICOs seen for 2018.

The Future of Work (2017-10-09)
• Measurement will be key in changing the nature of human work Middle management jobs are going to disappear rapidly. The work people do will become more intellectually difficult. People, especially Americans, spend long hours at work and yet aren’t as productive as they could be. A lot of the workday is funneled into browsing social media and the news, chatting with friends, etc.

The Future of Free Speech (2017-09-11)
Technology has fundamentally changed the properties of speech in terms of reach and precision, and might require us as a society to re-examine how we approach freedom of speech.

The Future of Truth (2017-07-31)
AI technologies are making it much easier for people to manipulate video and audio to turn the fake into believable images. To figure out what is true in future, people are going to have to pay more and rely on social networks. Blockchain technologies could help make systems more trustworthy.As the world realigns and truth becomes harder to discern, the simple but pure idea of paying agents for an understanding of truth once again becomes important. You will get what you pay for.

Seven Key Questions in the Cryptocurrency World (2017-07-03)
The growth of cryptocurrencies is creating the infrastructure for the most fundamental social shift in 20 years. But plenty of questions still have to be answered, including the role of regulators and how the industry will evolve as big financial firms get involved.

A Game Plan for VR and AR in 2017 (2017-06-05)
People in the AR/VR startup ecosystem need to figure out uses for the technology as it exists currently. Some odd-ball use cases that are worth exploring include helping people withdraw from the technologically-overloaded world and content delivered on hard-drives through the mail.The question that people in the VR/AR startup ecosystem must ask is what experiences are within reach that can be built on the technology as it exists today.

Time to Pay Attention to Cryptocurrencies (2017-05-22)
Now is the time to start paying attention to cryptocurrencies like Bitcoin or Ethereum, if you haven’t already. It’s becoming clear that a major use case for crypto will be to underpin an equity market.Right now, we are witnessing a new line of thinking taking hold—that the real use case for cryptocurrencies is to form an equity market, not a currency market.

The Wrinkle In Forecasting Autonomous Cars (2017-05-09)
New technologies usually take longer than initially expected to be introduced because rapid improvement eventually hits a point where the next stage of work becomes very expensive. That’s what will happen to self-driving cars, which is why their introduction is many years away.The Valley loves nothing more than extrapolating the future based on exponential J-curves with accelerating limitless growth and improvement.

The Bay Area Should Levy a 5% Equity Tax on Startups (2017-04-24)
Municipal governments in the Bay Area should require startups to give 5% of the founders’ equity for a municipal wealth fund. This reflects the value of the ecosystem in the region and gives municipal governments a source of financing long term. A 5% equity tax would be an enormous and instantly valuable asset for the community even if liquidity events and returns were far in the future.

The Second Coming of IT (2017-04-10)
The current wave of IT provides powerful tools to businesses while reducing the need for analysts and middle managers. But don’t expect these new applications to transform consumers’ lives anytime soon. . It is one thing for businesses to get leverage in decision-making through access to data, compute and good algorithms. It is quite another for those technologies to be fully developed enough to enter prime-time consumer use.

Why Twitter Should Start Charging (2017-04-03)
Adopting a subscription model could solve all of Twitter’s problems, but wouldn’t users revolt? Not if it’s done right. A good number might be willing to pay for a network with fewer ads, spambots and hate speech. . Twitter can no longer bank on getting usage, capital and ad revenue from those simply seeking a Facebook alternative.

Who Pays for Redesigning Streets for Self-Driving Cars? (2017-03-20)
If congestion created by ride-sharing services is any indication, self-driving cars will worsen traffic in major cities. Municipalities will likely be able to force self-driving car companies to bear the cost of retrofitting the road system, eroding profits.It is likely, therefore, that cities will look to the companies offering self-driving systems to help foot the bill for the congestion and retrofit work they cause.

Slowing Down the Digital Escapist Movement (2017-03-06)
We need to slow down the movement for people to disappear into a virtual reality future subsidized by basic income. The problem of human attention and dignity in an era of automation is very real, but the solutions being currently touted are a big missed opportunity.We clearly are finding ourselves with a massive surplus of human attention and labor which we don’t have great uses for in the current setup of our society.

The Return of History: Google Photos and Personal Big Data (2017-02-20)
The rise of AI-driven photo storage and organizing services like Google Photos heralds the return of photos as personal history, rather than as fleeting media. That signals a new battleground for tech companies over what value they can derive from a person’s photo history.We are on the cusp of bringing photos as meaningful history back into style.

The Similarity Between Silicon Valley and Trump (2017-02-13)
President Trump and tech companies are both populists in their own way, which complicates their ability to work out compromises. Both are beholden to their base of supporters and don’t have a lot of freedom to negotiate.It is hard to deny that if Trump were a VC-backed company challenging a legacy industry, he would be heralded as the unicorn of the decade.

Our Silent Future (2017-01-16)
Interacting with strangers on the street, or cab drivers and store assistants, gives us exposure to diverse ideas and helps our democracy. Technology like smartphones, VR and ride-sharing apps are removing those opportunities for interaction in a worrisome way.For the first time you can get a lift in a car from points A to B without ever speaking a word to the drive

Bot Check-In: A Year of Disappointment (2017-01-03)
Despite lots of PR, neither Facebook, Amazon or Google-developed bot platforms this year made it easy for developers to work with. Narrowly focused services can thrive in the near-term but mass-market bots have a way to go. You know Amazon is pushing something hard when every box you get from them is wrapped in ads for its bot platform on the tape.

In 2017, Tech Will Seek to Regain Moral High Ground (2016-12-27)
Tech companies need to stop overselling products that are years away from delivery, like VR and self-driving cars. And private firms should go public. Both steps would help the tech industry regain public admiration that was threatened in 2016. At the end of the current wave of mobile technology and apps, people aren’t getting the dopamine of new toys from technology companies.

Why Amazon Should Launch a Bank—But Won’t (2016-12-19)
Big tech companies would seem to be ideally placed to launch a consumer bank. But the realities of competing with entrenched banks and strict regulations in the industry means one is unlikely anytime soon. Technology companies and startups are focusing on just the valuable pieces of the ecosystem, without bothering to deal with the traditional loss leaders that the big banks need to engage in.

Free Speech and Democracy in the Age of Micro-Targeting (2016-12-05)
The growth of micro-targeting and disappearing messaging on the internet means that politicians can say different things to large numbers of people individually, in a way that can’t be monitored. Requirements to put this discourse on the public record are required to maintain democracy. Through micro-targeting and customization, the internet now provides the opportunity for people to reach an unlimited audience with unlimited speech.

The Rise of Information Imperialism (2016-11-21)
The internet is turning out to be a disaster for information diversity, contrary to widespread opinion among the technorati. The more seductive ideas crowd out niche opinions. The danger is that it’s now possible for the government to regulate actual speech. . Broader access to knowledge of a place, person, thing or topic changes the thing itself.

The First Modern Election (2016-11-07)
The advent of recorded history and the rise of free media have reshaped this election and should force us to consider some extreme solutions. . Hillary Clinton has been dogged throughout the campaign by email records—those on her private server and those found by WikiLeaks—which didn’t exist as a recorded medium even a few decades ago.

Where Airbnb May Be More Vulnerable than Uber (2016-10-31)
It’s great to be a natural global monopoly—or is it? People may love Airbnb while traveling, but that doesn’t mean they love it in their own backyards. . The problem is that, by definition, if you live in a given city, you almost certainly aren’t a local consumer of Airbnb.

Why Today’s Tech Narrative is Way Ahead of Reality (2016-10-17)
Tech companies are accelerating their narratives around everything from VR to self-driving cars because they need to convince the world the hypergrowth from mobile can be sustained. In a competitive market for engineering talent and attention, in an era in which technology is newly “cool,” there is a literal arms race to tell the biggest story possible.

How Data Analytics is Changing Startup Financing (2016-10-03)
The increased availability of cheap data analytics tools is making it easier for well-performing startups to raise series A financings at more favorable terms than was the case when series A required a lot of trust on the part of investors. All of a sudden, series A investors are basically asking for and doing large leveraged buyout-style diligence.

Uber’s Self-Driving Car Puzzle (2016-09-19)
The speed at which fully autonomous cars develop will have a big impact on Uber’s ability to compete with companies like Apple and Google. Without the need for drivers, Uber’s driver network switches from a strength to a weakness.

What Everyone Is Missing about Venture Returns (2016-09-05)
The debate between Andreessen Horowitz and the media last week over a WSJ article misses the reality that LPs don’t compare A16Z to Benchmark or other top tier firms on unrealized returns. Unlike public equities, LPs are limited in how much money top managers will take from them, and high returns are high returns. Because the Benchmark strategy limits the aggregate dollars they can deploy, it means even wealthy and well-connected individuals and institutions aren’t likely to get into the fund.

Why I Like, but Won’t Use, Instagram Stories For Now (2016-08-22)
Instagram was smart to roll out stories, and the launch was well executed. But, at least for now, the product experience suffers from technical hurdles and network issues. Even at an average of one second per piece of media, consuming stories on Instagram is going to run me 10 minutes a day.

Olympic Coverage: The Best of Times and the Worst of Times (2016-08-15)
The flood of Olympic footage from NBC and various other apps has made the event less interesting. It’s a case study in the pitfalls of unedited content. The Olympics “is now something we mostly experience on our own time and in our own way.”

Why the Bonus Culture Will Spread (2016-08-02)
Technology that measures performance is coming to industries where it historically wasn’t available. That’s going to cause a shift to a bonus culture of compensation, which is good broadly but will cause greater inequality for the foreseeable future. When you can measure output, you end up with performance-driven cultures. And performance-driven cultures create efficiency and good work—but also are linked to inequality.

How to Profit from Political Correctness (2016-07-18)
Political correctness is all the rage, yet our technology is letting us down. A keyboard that checks the user’s typing for offensive terms could be a good business, particularly in the enterprises and at universities. A politically correct keyboard could help reduce the amount of rude and offensive comments people make on social media, sometimes accidentally.

Bots in 2016: Mid-Year Check In (2016-07-05)
The past six months have shown that building compelling bots is very challenging. Completely automated bots aren’t ready for prime time and hybrid services with human involvement cost a lot to develop. How developers can make money from bots also hasn’t been clarified. But I’m still bullish on the shift to bots. Most of the bots released to date are just crappier versions of apps that already exist, pushing news and weather, ordering cars and flowers.

The Negative Side of Incubators (2016-06-20)
An oversupply of startup incubators is increasingly distorting company formation and capital raising. High-flying companies come out of demo days raising too much money while the rest don’t quite raise enough to succeed. As a friend recently put it to me, “you get a lot of bottle rockets” and very few true “launch vehicles.”

Era of Lean Startups Nears an End (2016-06-06)
Lean startups have dominated the past few years, flourishing in areas like media, advertising and messaging. But future challenges will address more complex, capital-intensive technologies like self-driving cars and virtual reality. This has implications for angel investors, incubators and big financiers. . Things are changing once again. Open-source software and infrastructure as a service will remain cheap foreveBut the low-hanging fruit of highly scalable software startups has mostly been eaten.

The Non-Monetizable Product Blind Spot (2016-05-23)
Why do so many common consumer tech needs still lack high-quality solutions? Follow the money—or in this case, the lack of it. There are plenty of products people want, but they’re not good businesses. It is because they fail as businesses that they can’t be built as products, not the other way around.

Why the Home Wars Aren’t the Phone Wars (2016-05-09)
Amazon, Apple and Google are all likely to have a presence in home-based smart agents in coming years, instead of one company dominating. That’s good news for developers, who won’t have only one route to distribution. It’s plausible that in a few years I will have three or four different voice-enabled systems in my house with overlapping but distinct functionalities.

The New Business of Editing (2016-04-25)
There are big potential businesses in editing down media, from books to television shows, and in pseudo-edited formats like Snapchat stories. . The value of editing is rising for many consumers, leading to big business opportunities for those who capitalize on them.

The Coming End of Capitalism (2016-04-11)
Technology is driving us towards a post-capitalist era, thanks to the rise of the sharing economy, social currencies and virtual reality. It’s not clear we’ll be better off. Sharing economy platforms are almost certainly GDP negative even if they are fundamentally good for the world and the environment.

Why Tech Needs Epic Failures (2016-03-28)
The much publicized failures at big tech companies in recent years, including the Apple Watch, Amazon phone and Facebook’s Home, are not something to worry about. It’s more a cause for concern if big companies aren’t trying big things that can move the needle—even if those efforts fail. Companies like Twitter and Yahoo just haven’t really produced any epic fails recently, which should give everyone pause.

Why We Should Abolish Time Zones (2016-03-14)
Dealing with people in different time zones is increasingly complicated for people and disastrous for software companies. A solution would be for tech companies to add GMT to phone interfaces as a step towards moving everyone to a single clock. My proposal is that a coalition of technology companies come together to add Greenwich Mean Time to the interfaces of phone clocks, in addition to local time.

Startups Need to Fire More Customers (2016-02-22)
One key advantage that startups have over big companies is their ability to fire bad customers. Coming into a period of belt-tightening, that is going to be important for startups to consider in rationalizing their businesses. . There are lots of bad customers in the world. Some require too much expensive support. Others have expectations mismatched with what a product provides or can provide.

Personal Voice Analysis for the New Year (2016-01-04)
Phone calls are still very important in business communications and for staying in touch with family, an analysis of my calls shows. That suggests voice calls could make a comeback more broadly if the product was improved

Star Wars’ Private Tech Valuation Formula (2015-12-21)
Private company valuations are more easily understood in comparison to Star Wars’ value Saying that Twitter is currently valued at four Star Wars-es, for instance, is to me much easier to understand than saying that Twitter is worth $15 billion.

Why Aren’t We Talking More About Autonomous Passenger Planes? (2015-12-21)
Despite all the talk about self-driving cars, there’s more chance autonomous small planes could emerge in the near term, opening up small-plane travel to a much wider group of people. If central ground-based pilots were flying small craft remotely with good on-board autopilots, then in theory each primary pilot could simultaneously fly a great number of planes at the same time.

The Good Enough Stuff Revolution (2015-12-07)
Traditional consumer product companies have to play on an increasingly wide playing field against a new crop of competitors selling direct to consumers online. The new competitors’ superior end-to-end experience makes the product itself less important Rightly or wrongly, years of marketing slug-fests have left me as a consumer assuming all toothpastes are basically the same.

Kodak’s Lesson for Detroit (2015-11-23)
The rise of self-driving cars threatens Detroit’s automakers in much the same way as Kodak was threatened by the development of digital film. Detroit’s prospects of responding may be no better than Kodak’s turned out to be even if Detroit tries to learn from Kodak’s experience. Now that cameras have become a feature of phones, even if Kodak had transitioned to digital cameras in a meaningful way, its success would have been short lived.

The New Winners and Losers in the Boredom Market (2015-11-09)
Technology has shifted the boredom market dramatically with big implications for information and entertainment companies. . Everyone else’s boredom has been atomized and variablized, in that technology has deeply changed the consistency of schedules.

How Growth Will Burst the Tech Bubble (2015-10-26)
To understand the tech bubble and how it will end, you need to consider the plummeting value of capital and other macro trends.

Why It’s Hard to Fix Failing Tech Cos. (2015-10-12)
It’s nearly impossible to turn around a Web-based company that has lost its way because its ability to find the right people is tied into the success of its product and its ability to grow. And the lack of hard assets means these companies are hard to sell. When a company has a product that is easy to market, good for customers, and easy to evolve, the product can help further draw in the right type of high quality and hard working human capital and drive the business.

The Case Against Product-Market Fit (2015-09-28)
Startups and investors should stop obsessing over product-market fit and focus on continuously finding new users. . The earliest versions of Facebook had amazing appeal to a few thousand undergraduates at Harvard, but the product had no fit in a broader sense.

Paying Up Front is a Legacy Concept (2015-09-14)
Apple’s introduction of a rental model for the iPhone reflects a broader trend towards subscription services driven in part by low interest rates. The business model gives companies a deeper connection to their customers, helping them make more relevant offers over time

Understanding the Hidden ‘Costs’ of Products (2015-08-24)
Product developers and investors should think about the cognitive cost of their products. The cognitive cost very often can be much higher than the financial cost. Products with a low cognitive cost are those where the technology fades away and don’t require a consumer’s ongoing attention. If you want to get value out of social applications or messaging apps, you need to be engaged daily.

Oculus Is for the Elderly (2015-08-10)
As VR remains more hype than reality, the enthusiasm some elderly have for it is encouraging and suggests talk of Oculus starting out with gamers is wrong. We have all seen the demos of grandma trying Oculus and loving it. Those emotions and reactions are real.

The Hidden Costs of Pivoting (2015-07-27)
Entrepreneurs and investors exploring pivots of their company need to consider the fact that doing so cripples their cap tables, creates compensation issues and benefits VCs far more than entrepreneurs. . When it was simply harder, more time-consuming, and more expensive to set up things like payroll, finance and accounting, the capital and labor that went into starting a company was truly valuable.

Startups Need Shade—Not Just Time—To Grow (2015-07-13)
Entrepreneurs should exploit the four main reasons big companies discard new businesses: market size, margin, relative effort and culture. . The bigger technology companies get, the harder it is for any given new product—even if it is successful—to move the needle for the company overall.

Why VCs are the New Investment Bankers (2015-06-29)
Special purpose vehicles are cropping up as companies push back their IPOs. But they have some of the same dynamics as going public. . When you adjust for the risk associated with the fact SPVs target earlier-stage companies, the actual economics of IPOs versus SPVs are pretty similar.

‘It’s a Trap’: The Danger Zone for Series B and C Startups (2015-06-15)
As they raise larger rounds at higher valuations, Series B and C stage entrepreneurs are exposing themselves to big risks, from inefficient uses of capital to longer-term challenges around hiring and morale. If entrepreneurs raise and then sideline capital, they are effectively agreeing to pay their investors an internal rate of return on capital without actually using the advantage they have purchased from investors for their equity.

Pricing for Consumer Perception (2015-06-01)
Silicon Valley companies are deploying two strategies to overcome consumer distrust that can arise when it’s not clear how a company makes money. One is to give users a fixed price they can focus on and the other is to make “everyday low prices” the focus. Technology companies are getting more and more sophisticated about how they talk about pricing with consumers, and realizing that “free” actually has taken on a huge psychic trust cost for users.

The End of the Bazaar (2015-05-11)
The bazaar-like nature of the Internet, where everything is for sale in the equivalent of an open-air market, is slowly giving way to a series of vertical applications that dominate trade in different categories. The sellers that have very high repeat rates theoretically have the ability to splinter off from the bazaar, and if they can provide meaningfully better quality or pricing without the support of the bazaar itself.

The Downside of Positive Feedback (2015-04-27)
On-demand services apps should change their feedback forms to let users offer a “thank you” instead of rating them on a five-star scale. The current system inhibits negative feedback. It is as hard to be negative about a person you have interacted with in the real world as it is easy to be mean to someone you have never met.

A Call for New Type of Mapping Platform (2015-04-13)
Digital maps need reinventing to reflect the variables that matter in making traveling decisions: time and money. For what is really useful—travel times and making actual navigation decisions—we need something beyond the digital maps to which we have become accustomed and which are dominated by Google.

The Economics of Sharing: Past and Present (2015-03-30)
The social media services that have thrived have all managed to affect the inputs of a basic cost-benefit analysis. Messaging and live-streaming apps are the latest examples. This all brings us back to the app category of the moment: live streaming video. Is it finally time for it to work as a form of social media, in the form of Periscope or Meerkat, or whatever might come next?

How Startups Get Their Metrics Wrong (2015-03-23)
When it comes to pitching investors on metrics, startups make three big mistakes, including focusing too much on weekly and monthly active users and getting too complicated. . As it has become easier and easier to accept payments online and people have become more and more willing to pay for all sorts of digital goods, I think companies have fewer excuses for not being able to justify their business based on revenue and profit.

Why Tech Comp is Broken and Ideas To Fix It (2015-03-09)
Equity compensation has become a mess for companies and employees. To create a more consistent marketplace where offers can be more easily understood and compared, new approaches must emerge. . If you accidentally pay someone tens or hundreds of millions of dollars above market, you are not only wasting money but you have also dealt yourself an almost un-winnable retention problem.

Why Late-Stage Investing is Becoming More Like Seed-Stage (2015-02-23)
The business model differences between seed-stage investing and late-stage are converging, as valuations are skyrocketing and traditional downside protection becomes less solid. That promises windfall returns but also higher losses for late-stage investors. The Whats-Insta-Snap-Uber-Pin-Air acquisitions and investments suggest a more radical change to the business models of the array of late stage investors and indicate that their math is converging with the binary-outcome mentality of the seed financiers.

Leapfrogging the U.S.: Transportation in Sao Paulo (2015-02-09)
The ecosystem around technology-assisted transportation and delivery is still up for grabs, with more competition for perceived incumbents than meets the eye. . My experience in Sao Paulo reinforced my view that Uber isn’t necessarily a natural global monopoly and that investors should value them as a company that will dominate markets where they are already entrenched, like the U.S.

Labor Economics and How Uber is Going to Disrupt Starbucks (2015-01-26)
The shift towards on-demand independent contract work is going to change the employment dynamics for a lot of companies, including those like Starbucks that currently have a competitive edge when it comes to hiring people. Many companies will struggle to adjust how they hire and what they offer to this new reality. Starbucks and others can’t just compete by increasing wages dollar-for-dollaLyft and others offer something they can’t: the ability to determine when you want to work

Native Advertising: A Convenient Pitch I’m Not Buying (2015-01-12)
Ad agencies and publishers have a big incentive to evangelize sponsored content. But the economics won’t make sense at scale compared to what Google, Facebook and others can offe. At an ecosystem level, I can’t see how the math on native advertising can benefit brands at scale after you factor in the massive overhead of managing the complexity of native advertising operations.

My 2020 Predictions: A Reality Check (2014-12-29)
Five years ago, I thought we’d be on the cusp of open technology platforms, Google would rule TV and antitrust battles would be looming. Where I was right and wrong—and why. Looking a bit further ahead to 2020, however, I suspect that in another five-year window there will be another major shift or two that I am currently massively underestimating just as I did the impact of mobile during the last period.

Technology, Taxi Medallions and the Ancien Régime (2014-12-22)
Local governments should phase out antiquated systems like taxi medallions in favor of more direct types of taxation. . Rather than deal with the bureaucratic complexity of collecting taxes from everyone, as well as take on the risk and complexity of managing fluctuating revenues, the government chose to take a steady revenue stream from a small number of private citizens and agencies that it could easily know and manage.

How Digital Photography Is Altering Our Memory (2014-12-15)
Looking back at my first fourteen years of digital photography, what is clear is that history is not only in the eye of the beholder, but a reflection of the beholder’s technology.

The Race to Become the Apple of Drones (2014-12-08)
I have heard from knowledgeable people that DJI had 2014 revenues that were somewhere between $300 million and $500 million.

As Technology Kills GDP, What’s Next? (2014-12-01)

When Tech Companies Enter Zero-Sum Markets (2014-11-24)
These zero-sum companies are going to have a hard time winning and being loved at the same time.

Uber As Gatekeeper to the Physical World (2014-11-17)
The possibilities could expand far beyond music. For example, Uber could add my name to a restaurant waitlist while I am en route in a car.

Native Apps: A Game Startups Can’t Win (2014-11-10)
Building native apps means a company needs far more than double the number of engineers, product managers, and designers it would if it could rely on the Web.

Big Brands Have Become Liabilities (2014-11-03)
The information available to a consumer about non-mass-brands is frequently better than the information about bigger brands. That’s because fans of small brands are more invested and more willing to spend the time sharing quality views and opinions.

Growth: Design It, Buy It or Get Stuck (2014-10-27)
If zero-marginal-cost consumer software could be more sustainably profitable for small companies, software would get better and consumers’ lives would improve.

What I’ve Learned Since Leaving Facebook (2014-10-20)
While a high-traffic commute can feel like a soul-crushing waste of time, I have to admit that I probably am not saving a meaningful amount of travel time staying in San Francisco, where instead I am dealing with piecemeal bit-by-bit friction among various activities that were once all in the same place.

Time to Hang up on Voice (2014-10-13)
Voice really messes with audience control—it is the anti-Snapchat.

How the Sharing Economy Threatens the Traditional Economy (2014-10-06)
Owning things has benefits, like on-demand access and appreciation in some cases. But it has three key costs: maintenance, depreciation and a loss of option value to do something else with your capital.

The Second Coming of Non-Consensus Currencies (2014-09-29)
Social capital—defined as the credit you earn with other people by helping them and collaborating with them—is the dark matter of our global economy. There is an enormous amount of it sloshing around.

Why Universities Should Wise Up and Retain Their ‘Users’ (2014-09-22)
Universities are well positioned to provide better service to their alumni than other educational institutions by moving towards a subscription model where “graduates” of a four-year program would continue to be enrolled for a few hundred—or thousand—dollars a yea

Selfies, Emoji and the Economics of Communication (2014-09-08)
When people talk about English getting “destroyed,” what they are really seeing is the economically rational shift towards publishing quickly as the cost of error or ambiguity goes down.