Writing

294 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

December 01, 2023

Reminder - Capital Light Conference Tomorrow AM

November 29, 2023

Invite to The Capital Light Conference on the 29th

November 24, 2023

Capital Light Conference on the 29th

November 24, 2023

Post-Factory VC' Conference Invite...

November 10, 2023

Followup from the 'State of VC' deck

November 03, 2023

Followup from the 'State of VC' deck

October 20, 2023

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

October 18, 2023

What To Do About Misinformation in the Upcoming Election Cycle?

October 18, 2023

Creator Financing Is Going Mainstream

December 29, 2022

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

November 10, 2022

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

April 26, 2022

How to Put Physical Assets on the Blockchain

February 24, 2022

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

December 02, 2021

The Metaverse Is Coming. What Happens Next?

November 12, 2021

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

November 05, 2021

What Sequoia Gains by Blowing Up the VC Fund Structure

October 27, 2021

The End of Venture Capital as We Know It

August 04, 2021

The Future of Investing Directly In People

March 22, 2021

Collectibles, Crypto NFTs, and the Monetization of Influence

March 02, 2021

Clubhouse and the Future of Cult-Driven Social Platforms

February 18, 2021

Equity Financing for Influencers

January 26, 2021

How Blocking Trump Puts the Future of the Internet at Risk

January 12, 2021

How Covid Accelerated Changes Already in the Making

December 22, 2020

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

November 11, 2020

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

October 20, 2020

Lessons From the Rise of OnlyFans

October 02, 2020

California’s 2020 Budget Solution: A Startup Equity Tax

August 31, 2020

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

August 10, 2020

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

July 21, 2020

The Escalating War Between Our Physical and Digital Realities

July 15, 2020

On Feed Ranking and Free Speech

June 22, 2020

The Slippery Slope to Censored Speech

June 08, 2020

The Over-Under on New Voice-Chat App Clubhouse

June 01, 2020

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

May 20, 2020

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

May 06, 2020

The Long-Term Implications of Extended Work From Home

April 30, 2020

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

April 06, 2020

How Coronavirus Epidemics Could Alter the Future of Tech

March 09, 2020

The 10 Ways TikTok Will Change Social Product Design

February 10, 2020

My Predictions for the Next Decade

January 14, 2020

Grading My 2010 Predictions—and What I Learned

January 14, 2020

In Defense of Deep Fakes

December 16, 2019

Four Paths Forward for ‘Social Products’

December 02, 2019

The Key Themes That Matter for the Future of Work

November 04, 2019

The Challenges Facing Free Speech

October 22, 2019

The Home Camera Wars

September 24, 2019

A Solution for Gig Economy Labor: Lightning Strikes

September 16, 2019

On Inequality and Risk Capacity

July 22, 2019

The Future of Free Speech

July 15, 2019

Remote Work and the Politics of Decentralization

May 06, 2019

Why the Internet Could Help Small Businesses Regain Power

April 22, 2019

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

April 01, 2019

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

March 18, 2019

A Warning on the Dangers of Ephemeral Messaging

March 08, 2019

ISAs and the Future of Securitization

February 25, 2019

The Pressure on the News Industry Is a Symptom of Disempowerment

February 11, 2019

How to Introduce a Wealth Tax

February 04, 2019

How Political Content Fills the Void Left by Micro-Targeting

January 21, 2019

What Technologists Can Learn From Religions

December 24, 2018

My Predictions for Crypto in 2019

December 17, 2018

We Need Better Measures of Social and Environmental Impacts

December 03, 2018

Is Uber Cash a Crypto Play?

November 12, 2018

The Coming of the Human Knowledge-Work Cloud

October 15, 2018

How the Internet Broke and What to Do About It

September 04, 2018

The Future of Privacy: Disinformation

August 20, 2018

Scooters: The New Self-Driving Cars

July 30, 2018

It’s Time for an American Internet Privacy Framework

June 19, 2018

Instagram Is the Real Virtual Reality, Not Oculus

May 28, 2018

Venmo Trust and The Blockchain

May 08, 2018

Governing the Internet

April 09, 2018

The Double-Edged Sword of Using Blockchains for Identity Portability

March 05, 2018

The Intellectual Tension Between Social Networking and Blockchains

February 12, 2018

Stable Coins, Oracles, Trust, and Identity

February 05, 2018

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

January 29, 2018

The Future of Hybrid Centralized-Decentralized Apps

January 15, 2018

Blockchains and the Right to Be Forgotten

December 18, 2017

14 Ways the Cryptocurrency Market Will Change in 2018

December 04, 2017

The Tower of Babel: Five Challenges of the Modern Internet

November 06, 2017

The Future of Work

October 09, 2017

The Future of Free Speech

September 11, 2017

The Future of Truth

July 31, 2017

Seven Key Questions in the Cryptocurrency World

July 03, 2017

A Game Plan for VR and AR in 2017

June 05, 2017

Time to Pay Attention to Cryptocurrencies

May 22, 2017

The Wrinkle In Forecasting Autonomous Cars

May 09, 2017

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

April 24, 2017

The Second Coming of IT

April 10, 2017

Why Twitter Should Start Charging

April 03, 2017

Who Pays for Redesigning Streets for Self-Driving Cars?

March 20, 2017

Slowing Down the Digital Escapist Movement

March 06, 2017

The Return of History: Google Photos and Personal Big Data

February 20, 2017

The Similarity Between Silicon Valley and Trump

February 13, 2017

Our Silent Future

January 16, 2017

Bot Check-In: A Year of Disappointment

January 03, 2017

In 2017, Tech Will Seek to Regain Moral High Ground

December 27, 2016

Why Amazon Should Launch a Bank—But Won’t

December 19, 2016

Free Speech and Democracy in the Age of Micro-Targeting

December 05, 2016

The Rise of Information Imperialism

November 21, 2016

The First Modern Election

November 07, 2016

Where Airbnb May Be More Vulnerable than Uber

October 31, 2016

Why Today’s Tech Narrative is Way Ahead of Reality

October 17, 2016

How Data Analytics is Changing Startup Financing

October 03, 2016

Uber’s Self-Driving Car Puzzle

September 19, 2016

What Everyone Is Missing about Venture Returns

September 05, 2016

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

August 22, 2016

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

August 15, 2016

Why the Bonus Culture Will Spread

August 02, 2016

How to Profit from Political Correctness

July 18, 2016

Bots in 2016: Mid-Year Check In

July 05, 2016

The Negative Side of Incubators

June 20, 2016

Era of Lean Startups Nears an End

June 06, 2016

The Non-Monetizable Product Blind Spot

May 23, 2016

Why the Home Wars Aren’t the Phone Wars

May 09, 2016

The New Business of Editing

April 25, 2016

The Coming End of Capitalism

April 11, 2016

Why Tech Needs Epic Failures

March 28, 2016

Why We Should Abolish Time Zones

March 14, 2016

Startups Need to Fire More Customers

February 22, 2016

Why Startups Are Doomed, Part Two

February 08, 2016

On Bots, Conversational Apps and Fin

January 18, 2016

Personal Voice Analysis for the New Year

January 04, 2016

Star Wars’ Private Tech Valuation Formula

December 21, 2015

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

December 21, 2015

The Good Enough Stuff Revolution

December 07, 2015

Kodak’s Lesson for Detroit

November 23, 2015

The New Winners and Losers in the Boredom Market

November 09, 2015

How Growth Will Burst the Tech Bubble

October 26, 2015

Why It’s Hard to Fix Failing Tech Cos.

October 12, 2015

The Case Against Product-Market Fit

September 28, 2015

Paying Up Front is a Legacy Concept

September 14, 2015

Understanding the Hidden ‘Costs’ of Products

August 24, 2015

Oculus Is for the Elderly

August 10, 2015

The Hidden Costs of Pivoting

July 27, 2015

Startups Need Shade—Not Just Time—To Grow

July 13, 2015

Why VCs are the New Investment Bankers

June 29, 2015

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

June 15, 2015

Pricing for Consumer Perception

June 01, 2015

The End of the Bazaar

May 11, 2015

The Downside of Positive Feedback

April 27, 2015

A Call for New Type of Mapping Platform

April 13, 2015

The Economics of Sharing: Past and Present

March 30, 2015

How Startups Get Their Metrics Wrong

March 23, 2015

Why Tech Comp is Broken and Ideas To Fix It

March 09, 2015

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

February 23, 2015

Leapfrogging the U.S.: Transportation in Sao Paulo

February 09, 2015

Labor Economics and How Uber is Going to Disrupt Starbucks

January 26, 2015

Native Advertising: A Convenient Pitch I’m Not Buying

January 12, 2015

My 2020 Predictions: A Reality Check

December 29, 2014

Technology, Taxi Medallions and the Ancien Régime

December 22, 2014

How Digital Photography Is Altering Our Memory

December 15, 2014

The Race to Become the Apple of Drones

December 08, 2014

As Technology Kills GDP, What’s Next?

December 01, 2014

When Tech Companies Enter Zero-Sum Markets

November 24, 2014

Uber As Gatekeeper to the Physical World

November 17, 2014

Native Apps: A Game Startups Can’t Win

November 10, 2014

Big Brands Have Become Liabilities

November 03, 2014

Growth: Design It, Buy It or Get Stuck

October 27, 2014

What I’ve Learned Since Leaving Facebook

October 20, 2014

Time to Hang up on Voice

October 13, 2014

How the Sharing Economy Threatens the Traditional Economy

October 06, 2014

The Second Coming of Non-Consensus Currencies

September 29, 2014

Why Universities Should Wise Up and Retain Their ‘Users’

September 22, 2014

The ‘Uber Effect’ on the Property Market

September 15, 2014

Selfies, Emoji and the Economics of Communication

September 08, 2014

Week in Review

90 posts

SWL Week in Review - AI Flippenings & 2x2s

May 02, 2026

Invite to Pearl genesis event

April 29, 2026

SWL Week in Review - WWE of Silicon Valley

April 24, 2026

Invite to Pearl genesis event

April 22, 2026

SWL Week in Review - Build Your Own Apps

April 17, 2026

SWL Week in Review - AI Is Not a Labor Crisis. It Is a Meaning Crisis.

April 12, 2026

SWL Week in Review - Looksmaxxing

April 05, 2026

SWL Week in Review - Bot or Not

March 28, 2026

SWL Week in Review - Master of Bots

March 20, 2026

SWL Week in Review - A Commodity Without Monopoly Power

March 14, 2026

SWL Week in Review - Claude Week

March 06, 2026

Polymath

March 04, 2026

SWL Week in Review - Roblox for Adults

February 27, 2026

SWL Week in Review - P90 selloff

February 24, 2026

SWL Week in Review - No Typists Anymore...

February 14, 2026

SWL Week in Review - Chosen by the Claw.

February 09, 2026

SWL Week in Review - Gold.

January 31, 2026

SWL Week in Review - half-kelly

January 24, 2026

SWL Week in Review - clawdbot

January 20, 2026

SWL Week in Review - Positivity?

January 09, 2026

SWL Week in Review - The Narratives of ’26

January 05, 2026

SWL Week in Review - Whip not Muscle

December 20, 2025

SWL Week in Review - Enemy of My Enemy

December 14, 2025

SWL Week in Review - Code Red Realities

December 05, 2025

SWL Week in Review - AI Business Model Wars

December 01, 2025

SWL Week in Review - Make Poor?

November 22, 2025

SWL Week in Review - Finger Size

November 14, 2025

SWL Week in Review - Etiquette

November 07, 2025

SWL Week in Review - Orizaba Reflections

November 01, 2025

SWL Week in Review - Lowbrow LLM culture

October 26, 2025

SWL Week in Review - Religion

October 19, 2025

SWL Week in Review - Slop

October 10, 2025

SWL Week in Review - Sora So What?

October 03, 2025

SWL Week in Review - Mercantilism

September 29, 2025

SWL Week in Review - 996 meta etiquette

September 19, 2025

SWL Week in Review - Memetic Warfare

September 12, 2025

SWL Week in Review - Wars of Attrition

September 05, 2025

SWL Week in Review - Top?

August 22, 2025

SWL Week in Review - Protest

August 17, 2025

SWL Week in Review - Betting on LLMs (literally)

August 08, 2025

SWL Week in Review - Outrage (and Figma)

August 01, 2025

SWL Week in Review - you know who would LOVE to hear about this...?

July 25, 2025

SWL Week in Review - is Vibecoding Entertainment?

July 18, 2025

SWL Week in Review - Launch of The Information TV + MZ live interview

July 14, 2025

Meet the M...eta-Yankees

July 05, 2025

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

June 28, 2025

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

June 20, 2025

Scale, Sambot, Harvard Reunion

June 14, 2025

Bears and Books no E, no T

June 06, 2025

who is single?... and steven pinker

June 01, 2025

Vibecode Reality, OF, and Incumbents

May 23, 2025

experiences' airbnb, farming, brokers

May 16, 2025

Tel Aviv

May 09, 2025

Antisemitism and AI

May 04, 2025

WTFVC 2025, Anti-Trust, and Ruck Rock

April 25, 2025

Harvard, and Decolonization

April 18, 2025

Tariffs and Spies...

April 04, 2025

Mostly Skiing... a few other thoughts

March 30, 2025

Spies, Teams and Themes

March 21, 2025

Space Bet, Softbank, and Bill Maher

March 17, 2025

Again and Again, Nothing is New

March 08, 2025

Narrative Selloff, HP, and Harvard

February 28, 2025

Slow Creator I, Merit First, and Memes

February 14, 2025

Understanding Memecoins, and Merit First

February 10, 2025

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

February 01, 2025

Tiktok, Trade Wars, and Financial Nihilism

January 24, 2025

The 2025 Gameplan, Free Speech, and Degen Investing

January 10, 2025

Elon 'Zaphod' Musk and AI pragmatism

December 20, 2024

Sora, United Health, Survivability of Seed Capital

December 13, 2024

Aaron Levie, Voight-Kampff, Retail Fomo

December 06, 2024

Venmo, Sling & Techbro Culture

November 29, 2024

Fwd Health, VC Regatta Model, Value Seed Investing

November 22, 2024

Summers, DOGE, Storytelling

November 16, 2024

Election Thoughts...

November 08, 2024

Tech Earnings, Destroying Trust in Reality

November 01, 2024

Vision Pro Failure, AI Cherry on Top

October 25, 2024

Planet Elon & Seed 'Value' Investing

October 18, 2024

Google Antitrust, The State of Seed

October 11, 2024

Monster F-it Funding Rounds, Golf Curious VC

October 04, 2024

Meta, Death of SaaS and YC...

September 27, 2024

the children, aleo, and hustle culture

September 22, 2024

Beast is Buzzfeed... Google SEO sadness

September 14, 2024

Founder Mode, Packy and Harry discoveries...

September 06, 2024

VC Reset, and Some Hiring

August 30, 2024

Turn Off, Tune Out, Drop In

August 16, 2024

AI Earnings, Harvard Wins

August 02, 2024

Opensource AI, Topaz, and Netanyahu

July 26, 2024

Trump, Kiki, and the Olympics

July 19, 2024

Patriotism and Summer

July 05, 2024

Hearsay, Debates and Hacks

July 01, 2024

Modest Conversations

25 posts

Modest Conversations: Income Share Agreements

February 11, 2019

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

November 20, 2017

Modest Conversations: Attention and Addiction

November 06, 2017

Modest Conversations: The Human Side of Building Technology

October 15, 2017

On Bitcoin Cash & New Ways Crypto-Projects Move Forward

August 06, 2017

On Product Management - Rousseau Kazi

July 29, 2017

Building Platform Products - Raylene Yung of Stripe & Facebook

July 23, 2017

Viewpoint From The Silicon Valley Entering Class of ‘17

July 16, 2017

Modest Conversations: Solving The Problems of Modern Cities

July 09, 2017

Modest Conversations: What You Know vs. Who You Know

July 01, 2017

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

June 25, 2017

Modest Conversations: Jobs, Inequality, and UBI

June 11, 2017

Modest Conversations: Cryptocurrency & ICOs vs. Venture Capital

June 04, 2017

Modest Conversations: Building Great Relationships With Kids

May 29, 2017

Modest Conversations: The Near Future of AI

May 21, 2017

Modest Conversations: Morning Routines of 2027 and 2047

May 14, 2017

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

May 07, 2017

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

April 30, 2017

Modest Conversations: The Future of Real Estate

April 23, 2017

Modest Conversations: Is Meditation The Next Yoga?

April 17, 2017

Modest Conversations: New York Tech & Social Media Fame

April 09, 2017

Modest Conversations: Virtual and Physical Communities

April 02, 2017

Modest Conversations: Unions, Regulatory Capture, and Tech

March 26, 2017

Modest Conversations: Who Drives Corporate Benefits and Responsibility?

March 20, 2017

The Information Presents: Modest Conversations

March 13, 2017

More or Less Friends

8 posts

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

September 29, 2023

The Apple Episode (Carbon Neutralish)

September 15, 2023

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

September 01, 2023

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

August 25, 2023

You should kill your startup, What replaces globalization

August 18, 2023

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

August 04, 2023

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

July 28, 2023

More or Less Podcast

July 25, 2023

Subscriber Survey

2 posts

Economy Soars, Uber Drops in The Information Survey

December 09, 2014

The Information Subscribers Say…

November 11, 2014

Slow Snail Mail

1 post

The Best Time to Build

January 30, 2023

Example Modest Proposals

1 post

A test title

October 13, 2021

Q&A

1 post

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

March 24, 2021

Other

1 post

Introducing “B is for Bitcoin”

August 29, 2018