Writing

250 essays and newsletters by Sam Lessin, organized by series. Sam writes about technology, investing, social media, AI, and culture as a columnist at The Information and in his personal newsletter.

Modest Proposals

165 posts

Followup from Capital Light Conference

Reminder - Capital Light Conference Tomorrow AM

Invite to The Capital Light Conference on the 29th

Capital Light Conference on the 29th

Post-Factory VC' Conference Invite...

Followup from the 'State of VC' deck

Followup from the 'State of VC' deck

The State of VC in 2023 - a Techno-Realist Manifesto

What To Do About Misinformation in the Upcoming Election Cycle?

Creator Financing Is Going Mainstream

From Theranos to FTX: Silicon Valley’s ‘No Additional Work Required’ Late-Stage VC Culture and What to Do About It

Elon Musk Is Silicon Valley’s New Hero—for Better or Worse

How to Put Physical Assets on the Blockchain

Facebook’s Decade-Old Missteps Should Be a Lesson for Web3

The Metaverse Is Coming. What Happens Next?

Investing Directly in People Is the Future of VC. Here’s How to Do It.

What Sequoia Gains by Blowing Up the VC Fund Structure

The End of Venture Capital as We Know It

The Future of Investing Directly In People

Collectibles, Crypto NFTs, and the Monetization of Influence

Clubhouse and the Future of Cult-Driven Social Platforms

Equity Financing for Influencers

How Blocking Trump Puts the Future of the Internet at Risk

How Covid Accelerated Changes Already in the Making

The Societal Problem of Only Needing 1,000 True Fans to Be Successful Online

How to Prevent Social Media’s Editorial Role From Becoming Censorship of Speech

Lessons From the Rise of OnlyFans

California’s 2020 Budget Solution: A Startup Equity Tax

Why Instagram’s Reels Rollout Will Slow, but Not Stop, TikTok’s Growth

The Simple and Practical Steps the Federal Government Should Take to Fix Online Speech

The Escalating War Between Our Physical and Digital Realities

On Feed Ranking and Free Speech

The Slippery Slope to Censored Speech

The Over-Under on New Voice-Chat App Clubhouse

How Covid-19 Is Changing Seed Companies and Financing in Silicon Valley

How Google and Apple Need to Play the Covid Contact Tracing Debate’s Next Phase

The Long-Term Implications of Extended Work From Home

Technology’s Role in Shaping the Impact of Covid-19

How Coronavirus Epidemics Could Alter the Future of Tech

The 10 Ways TikTok Will Change Social Product Design

My Predictions for the Next Decade

Grading My 2010 Predictions—and What I Learned

In Defense of Deep Fakes

Four Paths Forward for ‘Social Products’

The Key Themes That Matter for the Future of Work

The Challenges Facing Free Speech

The Home Camera Wars

A Solution for Gig Economy Labor: Lightning Strikes

On Inequality and Risk Capacity

The Future of Free Speech

Remote Work and the Politics of Decentralization

Why the Internet Could Help Small Businesses Regain Power

What Will Happen to the Social Wealth of Instagram Influencers as They Age?

The Cost and Risk of Regulations That Make Information ‘Own-able’

A Warning on the Dangers of Ephemeral Messaging

ISAs and the Future of Securitization

The Pressure on the News Industry Is a Symptom of Disempowerment

How to Introduce a Wealth Tax

How Political Content Fills the Void Left by Micro-Targeting

What Technologists Can Learn From Religions

My Predictions for Crypto in 2019

We Need Better Measures of Social and Environmental Impacts

Is Uber Cash a Crypto Play?

The Coming of the Human Knowledge-Work Cloud

How the Internet Broke and What to Do About It

The Future of Privacy: Disinformation

Scooters: The New Self-Driving Cars

It’s Time for an American Internet Privacy Framework

Instagram Is the Real Virtual Reality, Not Oculus

Venmo Trust and The Blockchain

Governing the Internet

The Double-Edged Sword of Using Blockchains for Identity Portability

The Intellectual Tension Between Social Networking and Blockchains

Stable Coins, Oracles, Trust, and Identity

Open vs. Closed in National Tech Strategies: the U.S. and China

The Future of Hybrid Centralized-Decentralized Apps

Blockchains and the Right to Be Forgotten

14 Ways the Cryptocurrency Market Will Change in 2018

The Tower of Babel: Five Challenges of the Modern Internet

The Future of Work

The Future of Free Speech

The Future of Truth

Seven Key Questions in the Cryptocurrency World

A Game Plan for VR and AR in 2017

Time to Pay Attention to Cryptocurrencies

The Wrinkle In Forecasting Autonomous Cars

The Bay Area Should Levy a 5% Equity Tax on Startups

The Second Coming of IT

Why Twitter Should Start Charging

Who Pays for Redesigning Streets for Self-Driving Cars?

Slowing Down the Digital Escapist Movement

The Return of History: Google Photos and Personal Big Data

The Similarity Between Silicon Valley and Trump

Our Silent Future

Bot Check-In: A Year of Disappointment

In 2017, Tech Will Seek to Regain Moral High Ground

Why Amazon Should Launch a Bank—But Won’t

Free Speech and Democracy in the Age of Micro-Targeting

The Rise of Information Imperialism

The First Modern Election

Where Airbnb May Be More Vulnerable than Uber

Why Today’s Tech Narrative is Way Ahead of Reality

How Data Analytics is Changing Startup Financing

Uber’s Self-Driving Car Puzzle

What Everyone Is Missing about Venture Returns

Why I Like, but Won’t Use, Instagram Stories For Now

Olympic Coverage: The Best of Times and the Worst of Times

Why the Bonus Culture Will Spread

How to Profit from Political Correctness

Bots in 2016: Mid-Year Check In

The Negative Side of Incubators

Era of Lean Startups Nears an End

The Non-Monetizable Product Blind Spot

Why the Home Wars Aren’t the Phone Wars

The New Business of Editing

The Coming End of Capitalism

Why Tech Needs Epic Failures

Why We Should Abolish Time Zones

Startups Need to Fire More Customers

Why Startups Are Doomed, Part Two

On Bots, Conversational Apps and Fin

Personal Voice Analysis for the New Year

Star Wars’ Private Tech Valuation Formula

Why Aren’t We Talking More About Autonomous Passenger Planes?

The Good Enough Stuff Revolution

Kodak’s Lesson for Detroit

The New Winners and Losers in the Boredom Market

How Growth Will Burst the Tech Bubble

Why It’s Hard to Fix Failing Tech Cos.

The Case Against Product-Market Fit

Paying Up Front is a Legacy Concept

Understanding the Hidden ‘Costs’ of Products

Oculus Is for the Elderly

The Hidden Costs of Pivoting

Startups Need Shade—Not Just Time—To Grow

Why VCs are the New Investment Bankers

‘It’s a Trap’: The Danger Zone for Series B and C Startups

Pricing for Consumer Perception

The End of the Bazaar

The Downside of Positive Feedback

A Call for New Type of Mapping Platform

The Economics of Sharing: Past and Present

How Startups Get Their Metrics Wrong

Why Tech Comp is Broken and Ideas To Fix It

Why Late-Stage Investing is Becoming More Like Seed-Stage

Leapfrogging the U.S.: Transportation in Sao Paulo

Labor Economics and How Uber is Going to Disrupt Starbucks

Native Advertising: A Convenient Pitch I’m Not Buying

My 2020 Predictions: A Reality Check

Technology, Taxi Medallions and the Ancien Régime

How Digital Photography Is Altering Our Memory

The Race to Become the Apple of Drones

As Technology Kills GDP, What’s Next?

When Tech Companies Enter Zero-Sum Markets

Uber As Gatekeeper to the Physical World

Native Apps: A Game Startups Can’t Win

Big Brands Have Become Liabilities

Growth: Design It, Buy It or Get Stuck

What I’ve Learned Since Leaving Facebook

Time to Hang up on Voice

How the Sharing Economy Threatens the Traditional Economy

The Second Coming of Non-Consensus Currencies

Why Universities Should Wise Up and Retain Their ‘Users’

The ‘Uber Effect’ on the Property Market

Selfies, Emoji and the Economics of Communication

Week in Review

46 posts

AI Pokemon (catch'em all) & Hierarchy of Business Models

Bears and Books no E, no T

experiences' airbnb, farming, brokers

Scale, Sambot, Harvard Reunion

Socialism Blowback + Hiring & Sourcing in Age of AI...

Meet the M...eta-Yankees

Opensource AI, Topaz, and Netanyahu

Patriotism and Summer

Elon 'Zaphod' Musk and AI pragmatism

The 2025 Gameplan, Free Speech, and Degen Investing

Sora, United Health, Survivability of Seed Capital

VC Reset, and Some Hiring

Deepseek, Memes, and oh my Jelly-Jelly...

Monster F-it Funding Rounds, Golf Curious VC

Trump, Kiki, and the Olympics

Turn Off, Tune Out, Drop In

AI Earnings, Harvard Wins

Election Thoughts...

Fwd Health, VC Regatta Model, Value Seed Investing

WTFVC 2025, Anti-Trust, and Ruck Rock

Slow Creator I, Merit First, and Memes

Founder Mode, Packy and Harry discoveries...

Tiktok, Trade Wars, and Financial Nihilism

Antisemitism and AI

the children, aleo, and hustle culture

Meta, Death of SaaS and YC...

Understanding Memecoins, and Merit First

Summers, DOGE, Storytelling

Space Bet, Softbank, and Bill Maher

Tech Earnings, Destroying Trust in Reality

Again and Again, Nothing is New

Google Antitrust, The State of Seed

Vibecode Reality, OF, and Incumbents

Tel Aviv

Narrative Selloff, HP, and Harvard

Planet Elon & Seed 'Value' Investing

who is single?... and steven pinker

Harvard, and Decolonization

Vision Pro Failure, AI Cherry on Top

Venmo, Sling & Techbro Culture

Beast is Buzzfeed... Google SEO sadness

Mostly Skiing... a few other thoughts

Spies, Teams and Themes

Tariffs and Spies...

Hearsay, Debates and Hacks

Aaron Levie, Voight-Kampff, Retail Fomo

Modest Conversations

25 posts

Modest Conversations: Income Share Agreements

Modest Conversations: Runaway Objective Functions & Human Agency with Tim O’Reilly

Modest Conversations: Attention and Addiction

Modest Conversations: The Human Side of Building Technology

On Bitcoin Cash & New Ways Crypto-Projects Move Forward

On Product Management - Rousseau Kazi

Building Platform Products - Raylene Yung of Stripe & Facebook

Viewpoint From The Silicon Valley Entering Class of ‘17

Modest Conversations: Solving The Problems of Modern Cities

Modest Conversations: What You Know vs. Who You Know

Modest Conversations: On Metrics & Building What Your Competitors Can’t Measure

Modest Conversations: Jobs, Inequality, and UBI

Modest Conversations: Cryptocurrency & ICOs vs. Venture Capital

Modest Conversations: Building Great Relationships With Kids

Modest Conversations: The Near Future of AI

Modest Conversations: Morning Routines of 2027 and 2047

Modest Conversations: 09 - Have We Reached The Limits of VC? - Bryce Roberts of OATV & Indie.vc

08 - Entrepreneurial Resilience - Leila Janah, Founder Samasource and LXMI

Modest Conversations: The Future of Real Estate

Modest Conversations: Is Meditation The Next Yoga?

Modest Conversations: New York Tech & Social Media Fame

Modest Conversations: Virtual and Physical Communities

Modest Conversations: Unions, Regulatory Capture, and Tech

Modest Conversations: Who Drives Corporate Benefits and Responsibility?

The Information Presents: Modest Conversations

More or Less Friends

8 posts

Scott Belsky & Why Your AI Startup is Probably Already Dead*

The Apple Episode (Carbon Neutralish)

Notes from Beijing, Energy Vampires and a Venture Capital Therapy Session

Why Hybrid Work Doesn't Work, Long Live the Phone Call

You should kill your startup, What replaces globalization

Where's the Barbie business pop? Where brands beat marketplaces

Episode 7: Elon's X game and RIP seed investing

More or Less Podcast

Subscriber Survey

2 posts

Economy Soars, Uber Drops in The Information Survey

The Information Subscribers Say…

Slow Snail Mail

1 post

The Best Time to Build

Example Modest Proposals

1 post

A test title

Q&A

1 post

‘MrBeast’ Explains His Plans to Help YouTube Creators Raise Equity Finance

Other

1 post

Introducing “B is for Bitcoin”