Internet Policy, Privacy, and Free Speech

A Warning on the Dangers of Ephemeral Messaging
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.

How the Internet Broke and What to Do About It (Sept, 2018)
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 Tower of Babel: Five Challenges of the Modern Internet (Nov 2017)
Consolidation of speech platforms poses risks, the current internet is biased toward extreme speeh, choices loom about prioritizing freedom vs. security.

Free Speech and Democracy in the Age of Micro-Targeting (Dec 2016)
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.

Open vs. Closed in National Tech Strategies: the U.S. and China (Jan 2018)
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.

How to Introduce a Wealth Tax
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.

It’s Time for an American Internet Privacy Framework
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.

Governing the Internet (April 2018)
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?

The Future of Truth (Jul 2017)
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.

The Future of Free Speech (Sept 2017)
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 Economics of Sharing: Past and Present (Mar 2015)
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.

The Future of Privacy: Disinformation
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.

How Political Content Fills the Void Left by Micro-Targeting
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.

How Digital Photography Is Altering Our Memory
There was the era before digital cameras and social networks when photos were natural, candid and not posed—what I will call the “Era of Obliviousness.” Then there was the era when, thanks primarily to Facebook and cheap digital cameras, photos became posed and often clustered in albums around groups of people—what I will call the “Era of Sharing.” And now, we are in the “Era of Attention,” when taking photos is less about capturing reality and more about creating content to show off to others to drive attention and feedback.

Economics & The Internet's Impact on the Economy

The Second Coming of Non-Consensus Currencies (Sept 2014)
While traditional consensus currencies are not going away, I believe a type of currency is on the rise that has nothing to do with consensus. The spread of efficient communication technology is enabling the recapitalization of social capital, which is both the original form of capital and the ultimate non-consensus currency.

How the Sharing Economy Threatens the Traditional Economy (Oct 2014)
Communication technology is making it easier to access goods and services on the fly without owning them, and as a result consumers increasingly won’t want to. 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. Technology is vaporizing the relative advantages of ownership and making the costs more apparent (Here’s a TED talk I gave on the topic a few years ago for more color.)

As Technology Kills GDP, What’s Next? (Dec 2014)
Gross Domestic Product has long been criticized as a flawed measure of the strength of an economy. But as technology topples the core economic assumptions of our society, GDP is rapidly becoming a completely broken metric. So what should replace GDP as an easily expressed yardstick for our economy and society? How should we measure the economy and its progress on the back of the Internet, on-demand services and the social reputation economy?

ISAs and the Future of Securitization
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.

Selfies, Emoji and the Economics of Communication (Sept 2014)
Marginal Value of Expression = (Value of Consumption For Counterpart - Cost of Consumption for Counterpart) - Cost of Expression

The Future of Work & Automation

The Coming of the Human Knowledge-Work Cloud
Knowledge work is going to move to a model much like how cloud computing works today, backed by a combination of humans and machines. This is why and how.

The Future of Work (Oct 2017)
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.

The Second Coming of IT (April 2017)
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.

Crypto, Decentralization, and Trust

What Technologists Can Learn From Religions
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.

The Double-Edged Sword of Using Blockchains for Identity Portability
Many technologists are excited about using blockchain to make identities portable on the internet, but it will likely come with strings attached.

Venmo Trust and The Blockchain
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.

Stable Coins, Oracles, Trust, and Identity
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.

The Future of Hybrid Centralized-Decentralized Apps (Jan 2018)
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.

Blockchains and the Right to Be Forgotten (Dec, 2017)
Blockchain technology challenges existing regulations governing content on the internet, rendering impractical the ‘right to be forgotten’ in Europe.

Seven Key Questions in the Cryptocurrency World (Jul, 2017)
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.

Time to Pay Attention to Cryptocurrencies (May 2017)
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.

Startups, VC, and SV Culture

What Everyone Is Missing about Venture Returns (Sept 2016)
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.

Why Tech Comp is Broken and Ideas To Fix It (Mar 2015)
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.

Why the Bonus Culture Will Spread (Aug 2016)
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.

The Similarity Between Silicon Valley and Trump (Feb, 2017)
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.

Era of Lean Startups Nears an End (Jun 2016)
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.

The Non-Monetizable Product Blind Spot (May 2016)
Why do so many common consumer tech needs still lack high-quality solutions? Follow the money—or in this case, the lack of it.

Why Tech Needs Epic Failures (Mar 2016)
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.

Startups Need to Fire More Customers (Feb 2016)
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.

Why Startups Are Doomed, Part Two (Feb 2016)
The rise of marketplace businesses has made bigger businesses more efficient, not less, which is bad news for startups.

Why the Home Wars Aren’t the Phone Wars (May 2016)
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.

How Startups Get Their Metrics Wrong (Mar 2015)
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.

The Good Enough Stuff Revolution (Dec 2015)
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.

Why It’s Hard to Fix Failing Tech Cos. (Oct 2015)
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.

The Case Against Product-Market Fit (Sept 2015)
Startups and investors should stop obsessing over product-market fit and focus on continuously finding new users.

The Hidden Costs of Pivoting (July 2015)
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.

Startups Need Shade—Not Just Time—To Grow (July 2015)
Entrepreneurs should exploit the four main reasons big companies discard new businesses: market size, margin, relative effort and culture.

When Tech Companies Enter Zero-Sum Markets
Technology companies often fiercely compete inside the technology industry. But in infinite markets with open-ended growth potential, these technology companies have generally been non-zero-sum with the outside world. In many cases productivity and communication technologies have grown the pie for everyone. But those times are changing and increasingly the most interesting technology companies are competing in finite markets against legacy companies. Technology companies are entering zero-sum spaces.

The End of the Bazaar (May 2015)
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 Wrinkle In Forecasting Autonomous Cars (May 2017)
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.

Who Pays for Redesigning Streets for Self-Driving Cars? (Mar 2017)
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.

Uber’s Self-Driving Car Puzzle (Sept 2016)
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.

Why Aren’t We Talking More About Autonomous Passenger Planes? (Dec 2016) 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.

The ‘Uber Effect’ on the Property Market (Sept 2014)
Real estate is one of the few industries in the world that’s bigger than transportation. But in the coming decades, companies like Uber and Lyft—eventually super-charged by self-driving cars—are likely to change living patterns and upend property markets in ways that we’ve only begun to understand.

Labor Economics and How Uber is Going to Disrupt Starbucks (Jan 2015)
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.

Uber As Gatekeeper to the Physical World (Nov 2014)
Think of Uber not just as a transportation service, but as a method for delivering customers to businesses. Marketers control the top of the funnel by building awareness around restaurants or services. Uber controls far lower down in the funnel, delivering the actual people.

Other Writing

B is for Bitcoin Children’s Book
My illustrated childrens book on Bitcoin from (A)bsolute Algorithms to (Z)ero Knoweldge Proofs.

Selfies, Emoji and the Economics of Communication (Sept, 2014)
My first Modest Proposal in The Informaiton, in which I argue for the economic ratinoality of emoji and selfies. Marginal Value of Expression = (Value of Consumption For Counterpart - Cost of Consumption for Counterpart) - Cost of Expression

Living Doc - Investment Themes
A doc where I keep investment themes I think are interesting as they occur to me.

Living Doc - Me Elsewhere
Some links to things I have participated in… partially so I don’t lose them, and partially if anyone is interested :)

I am Sam Lessin, I work at Fin on instrumenting the future of work, invest as a partner at Slow and intern writing at The Information

This is some of my writing and ideas .. for more check out my column 'modest proposals'