30 Years Ago I Said ‘No’ to Working for Phil Donahue, and ‘Yes’ to Conan O’Brien.

September 02, 2024

“I will say that a lot of tension arose from Googler’s expectations that the company’s culture had…

August 26, 2024

A Hollywood Director on Whether AI Will Replace Him, What It Takes to Raise a Series B in 2024…

August 18, 2024

Email Introductions 101. And Why a Strong Cold Email Always Beats a Weak Warm One.

August 17, 2024

What Do VC Returns Actually Look Like? Here’s a Screenshot from my AngelList account

August 14, 2024

The Best of the New VCs Will Outperform Most of the Legacy Ones.

August 13, 2024

Thank You Susan

August 10, 2024

Why Company Communication Breaks at 50 People; a VC Notices What Happens When a Startup is Down to…

August 10, 2024

Building Your First Exec Team; Avoiding Micromanagement; Skilled Immigration Should Be Prioritized…

July 28, 2024

Traits a VC Looks For In Founders, Are Plants Actually Intelligent?,

July 03, 2024

The Future of Fashion Commerce Is a Designer’s AI Bot Saying You Look Great and Your Personal AI…

June 24, 2024

An Operating Manual for Cofounders, Why It’s Silly to Say Your Funding Round was “Oversubscribed,”…

June 04, 2024

Backing New VC Firms With Screendoor: Welcoming OGs from First Round Capital, Pear VC, Reach…

May 22, 2024

Textio’s Founder Kieran Snyder on the Two Advantages Startups Have in AI (While Remaining Skeptical…

May 17, 2024

The Airline Chatbot Lied and a Passenger Sued, Why You Shouldn’t Care About Your VC Being ‘Founder…

May 14, 2024

Are Startup Stock Options Like ‘Lottery Tickets?’ A CEO and Former Employee Discuss. And My POV.

May 11, 2024

He Sold His Startup for $130 Million, Here’s What He Learned, and Questions to Ask When Considering…

May 05, 2024

Taylor’s Typewriter Boom, How Nvidia Handles Failures, and Matt Mullenweg’s Open Source…

April 28, 2024

When to Tip $$, Andrew Huberman-ization of America, Jelly Roll Owns 100% of His Masters, and More…

March 18, 2024

Seven ‘Pivots’ Later, Warmly Finally Found Its Stride.

March 16, 2024

Every time OpenAI cuts a check for training data, an unlaunched competitive startup dies.

February 23, 2024

The Introvert Economy, the Case for Longer Founder Vesting Cycles, What Happens When Your Product…

February 20, 2024

Incentives in Venture Capital, Why You Should Avoid Your Competitors’ Investors, China’s Malaise…

February 06, 2024

The Fonz on Leadership Lessons He Learned From Happy Days

February 04, 2024

VCs Are Leaving Their Firms But It’s The Founders They Backed Who Often Get Hurt

January 28, 2024

“It takes a year to find great executives so you must always look down the field.”

January 13, 2024

2024’s First Link Blog Post (Because Happy Birthday Matt Mullenweg)

January 04, 2024

Greenhouse CEO Daniel Chait on how AI is changing human resources and weaning his company off…

December 11, 2023

Why ‘Fairness’ Matters in Techno-Optimism, How To Successfully Take Time Off Between Jobs, and Why…

November 14, 2023

How You Actually Feel Selling Your Company, Is It Worth Tolerating a Toxic Employee, & TechCrunch’s…

September 23, 2023

Startups Fail All The Time, But Many Could Fail Better By Thinking Beyond the VCs and Founders

September 20, 2023

Venture Capitalists Will Overpay For Seed Rounds But For Reasons You Likely Haven’t Considered

September 15, 2023

Why VC Isn’t Right for Most Startups, The Place Where Taylor Swift, Gwar & Cypress Hill are Equals…

September 10, 2023

The Only Thing Which Has Failed About The ‘Creator Economy’ Thus Far Is Venture Capital’s Attempts…

September 09, 2023

A Technical Cofounder Tells You How To Find Your Technical Cofounder, Where The Stuff We Return to…

September 04, 2023

And let’s be clear: The term “culture and employee engagement” doesn’t mean “Happy Hours” and…

August 31, 2023

The Best View of “What’s San Francisco Like Right Now?” Is Understanding This Simple Framework

August 26, 2023

Why Starting Your Investor Updates With “Cash on Hand” Information is a Major Red Flag Right Now.

August 25, 2023

Lightspeed VC Michael Mignano on Why Apple’s Threats Influenced His Decision to Sell Anchor to…

August 23, 2023

I Like You But You’re Not Yet My Friend.

August 19, 2023

Why We’re Heading Into the “Perfect Storm” of Startup Closures.

August 13, 2023

Sold at the Peak: Congrats to Founders of Honey, Mirror, Frame.io

August 10, 2023

“Winners Take None:” Coworking, Self Storage, Scooters Have Burned Billions of Investor Dollars and…

August 08, 2023

Link Blog: Run Away When a VC Wants to ‘Preempt Your Next Round,’ How Barbie Got Made, Air Jordan…

August 06, 2023

Great Time to Start a Company, Tough Time to Be Running One

August 05, 2023

Threads Gives You The Chance To Rebuild Your Follow Graph.

July 09, 2023

July 4th Linkblog: Don’t Fake FOMO When Fundraising, 50 Cent on Success, Miss Texas on Reproductive…

July 04, 2023

“If I never again have to read a bunch of entitled tech bros mansplaining on twitter about their…

June 26, 2023

Linkblog: What AI Model Should Your Startup Use, What Your VC Can’t Do For You, and More

June 16, 2023

Why a Seed VC Should Care More About Ownership Than Valuation on Each New Investment, But…

June 09, 2023

I Can’t Stop Marveling at SF’s Driverless Cars

June 09, 2023

Linkblog: What Do Investors Really Want From Founders; Stop Hiring Mediocre Executives; and…

June 05, 2023

Three Reads Over a Holiday Weekend: Encrypted Phones Spill The Beans On Criminals, Yard Signs Ruin…

May 27, 2023

The Acquihire Market for Early Stage Startups is Ice Cold.

May 19, 2023

Instead of Asking AI Companies to ‘SLOW DOWN’ We Should Encourage Them to Move Even Faster

April 04, 2023

The Industry Needs to do One Thing to Avoid Regulation: Provide Better Phone Support

March 27, 2023

Five Short Links To Long Reads

March 19, 2023

I Graduated Into The 2000 DotCom Crash, And It Was The Best Thing To Ever Happen To My Career

March 13, 2023

As a Human, I’m Excited About AI. As an Investor, I’m Still Wrestling With a Few Questions

March 07, 2023

Killing The ‘Must Have a Warm Intro To a VC’ Myth Will Be Good For Founders and Great for the World

March 02, 2023

“Imposter Syndrome” is Definitely Misnamed, Might Be a Condition of Priviledge, & Has a Fascinating…

February 27, 2023

AI Enthusiasm is Not a Bubble and Even if it was We Wouldn’t Necessarily Know it Yet

February 22, 2023

Changing The Face(s) of Venture Capital, Screendoor Hires Lisa Cawley, Our First Managing Director…

February 21, 2023

Am I a Bad VC for Wanting Our Portfolio Companies To Make More Money for Public Investors Than They…

February 20, 2023

Virtual Worlds Are Trade Schools In Disguise

February 18, 2023

You Probably Can’t Hire Stripe’s First COO But Soon You’ll Be Able To Read Her Book

February 13, 2023

Some of the Best Founders Are “Difficult” People

February 07, 2023

“I’m Interviewing With AI Companies. How Do I Know If They Have an Ethical North Star?”

February 03, 2023

Using Startup Advisors To Help Your New Hires Can Be The Difference Between Their Success or…

January 31, 2023

For Those Recently Laid Off From Google, Leaving Your Job Doesn’t Mean Losing Your Identity.

January 24, 2023

“Trying to bet on virality is just, it’s not, it’s something you can prepare for, but you can’t…

January 21, 2023

Can OpenAI Live Up To The ‘Open’ Brand Promise?

January 17, 2023

Death of The Generalist Seed VC

January 15, 2023

Amazon v Google v China: Quantum Computing Will Blow Your Mind.

January 12, 2023

The Economics of War and Vintage Concert T-Shirts.

January 10, 2023

2022’s Startup Layoffs Will Result In 2023 Startup Wind Downs

January 03, 2023

Seven Links To Read (12/30/22)

December 30, 2022

Can a VC Think Like a Startup? That’s Part of Homebrew’s Goal in Switching to Our Own Capital.

December 27, 2022

2022 Was The Year We Decided To Not Raise Another Venture Capital Fund. What Happened Next..

December 21, 2022

“Dead on arrival. I’m still waiting to see the first good Mastodon post. God help us.”

December 12, 2022

Twikileaks

December 09, 2022

Don’t Believe The Terminator Movies, Artificial Intelligence’s First Strike Against Humanity Is By…

December 05, 2022

Why VCs Explaining “It Was Only 4% Of Our Fund” Is Misleading Minimization When a High Flying…

November 28, 2022

Now, Next, and At Exit: The Three Ways To Evaluate Compensation Before Accepting That New Startup…

November 22, 2022

“There is magic in the trying and learning and trying again..

November 14, 2022

“Being a 2nd time founder is basically figuring out how to leverage all your hype without believing…

November 07, 2022

“You have to fight the urge to do everything the same way you did it the first time:” Pros and Cons…

October 31, 2022

Two Questions To Ask During Hiring Reference Checks Instead Of “Where Can They Improve?”

October 24, 2022

“As a Senator, the first project I’d tackle would be immigration.”

October 22, 2022

Like Bourbon and Whiskey?

October 13, 2022

Paid Subscriptions Aren’t Enough. Why Substack Should Build An App Store

October 10, 2022

Why Your Next ‘Yes’ Hire Might Come From Someone Who Just Said ‘No’ To Your Job Offer

October 05, 2022

The Most Important Concept of 2022’s Startup Downturn is Not Just Surviving, But Staying “Default…

September 29, 2022

Succeeding in Venture Capital is Mostly About Knowing What to Buy. But When To Sell Matters Also.

September 24, 2022

Why Figma is Worth $20B And Other Observations From The Adobe Acquisition

September 16, 2022

When a VC Passes, And Is Wrong: Real Talk Between Me and Ethena’s CEO Roxanne Petraeus

September 09, 2022

“Workers are mad and no longer willing to sit idly by being spoon fed ‘we’re family’ bullshit from…

August 29, 2022

“I guess we’ll know we’ve made it when a woman can get away with behaving like Elon Musk.”

August 22, 2022

I Assumed This Memoir Was Just Another CEO’s Personal Brand Reinvention. I Was Very Wrong.

August 15, 2022

Seed Stage Founders Undervalue Angels With Marketing & Comms Expertise

August 08, 2022

Three Startup Pitch Deck Mistakes That Are Red Flags For Venture Investors

July 27, 2022

Celebrating Milestones Doesn’t Kill Your Ambition. I Realized This Too Late To Enjoy Many Of Them.

July 21, 2022

These Two Questions Are All You Need To Understand The Next Few Years of Venture & Startups

July 14, 2022

50+ Free Guides To Startup HR, Recruiting, Leadership ++

July 08, 2022

In This Market, It’s a Great Time for a Mutual “Try Before You Buy”

July 07, 2022

More New Hires Are Ghosting Before Their Start Date. Here’s How To Prevent That.

June 28, 2022

If You’re Interviewing With a Startup, Here Are Three Questions To Ask Their Investors

June 22, 2022

Company Culture Is Really Important, But The Way We Talk About It Is Wrong

June 20, 2022

Five Great Blog Posts I Found This Week

June 12, 2022

15,000 Tech Workers Have Been Let Go In May. Were You One of Them?

May 31, 2022

“My career was on the rise, I had the beginnings of a financial safety net …Yet I started to…

May 23, 2022

What Does It Mean To Be A “Good-Faith Skeptic” & When Is “Bad-Faith” Warranted

May 16, 2022

Most Startups Add Independent Board Members Too Late To Make A Real Difference. Here’s Why.

May 06, 2022

What’s To Stop Twitter’s New Owner From Publishing The Company’s Historical Internal Emails?

April 27, 2022

What Was The First Concert You Attended?

April 23, 2022

Keep Your Personal Burn Rate Low To Maximize Your Options

April 13, 2022

Yeah, Meta’s Rumored ‘Zuck Bucks’ Sound Weird But I Once Thought Facebook Credits Could Be Bigger…

April 07, 2022

A Good Investor Can Help You Close Candidates.

March 31, 2022

It’s Pretty Cringey To Self-Anoint Yourself Any of These Four

March 26, 2022

I Love Backing ‘Mission-Driven’ Founders But Here’s Where They Struggle as Startup CEOs

March 17, 2022

Fired Up To Invest In East Fork, A Company With A Mission

March 07, 2022

VCs ‘Anti-Portfolio’ Lists Are Mostly Performative BS

February 23, 2022

Peloton’s New CEO Is Incredibly Candid, & the ‘Micromort’ Estimates Risk of Dying From Any Activity

February 21, 2022

How To Raise Funding When Investors Hate Your Market

February 17, 2022

How to Decide if a Career in Venture Capital is Right for You

February 12, 2022

Neil Young’s Spotify Protest Isn’t Censorship, It’s Exercising His Free Market Rights.

January 30, 2022

The Role That Luck Plays In Our Success

January 17, 2022

Investor Jarrod Dicker on how “the emergence of NFTs has brought provable digital ownership to the…

January 12, 2022

In Order to Live a Happier Life, Say “No” More in 2022

January 07, 2022

“I try not to ride the emotional wave of startup life like I sometimes did before” and other…

January 06, 2022

Video Games Were What Hooked Meta’s CTO’s Andrew Bosworth On Tech.

January 04, 2022

Why Today’s ‘Mentorship Programs’ Mostly Fail Women in Tech (and How to Improve Them)

December 29, 2021

“It’s okay to take profits and not hodl forever.”

December 23, 2021

I’m Successful In Tech Because I Managed To Visit The Future Without A Time Machine

December 16, 2021

In the Metaverse, It’s Always ‘Ladies’ Night’

December 06, 2021

Avatars Don’t Poop But You Can Be Sure The Metaverse Will Have Toilets

December 02, 2021

How I Calmed My Imposter Syndrome With These Two Tricks

November 23, 2021

How I Calmed My Imposter Syndrome with These Two Tricks

November 23, 2021

Blame Me For YouTube’s ‘Dislike’ Option. But Now I’m Glad They’re Removing It.

November 15, 2021

‘Entrepreneur In Residence’ Used To Be One Of Silicon Valley’s Most Prestigious Titles.

November 10, 2021

“I’ll see in 2022 if I can turn The SF Minute into an actual business that’s somewhat sustainable”

November 05, 2021

Vanity Fair’s Profile of The Rock is Just Fantastic

November 01, 2021

A Tech Millionaire’s Guide To Philanthropy

October 29, 2021

What I Tell All New VCs About Their First Funds

October 22, 2021

Why This Ex-Facebook Engineer Thinks Non-Technical Product Managers Are Awesome (Oh and He’s…

October 15, 2021

Learn To Hire Well And You’ll Never Lose

October 09, 2021

Ode to a Non-Technical Product Manager (Revisited)

September 30, 2021

Win The ‘Sure Things’ Or Find The Hidden Gems? What’s My Job As A VC?

September 25, 2021

Help Me Give $10,000 To Every Mother Counts, Supporting Maternal Health Here & Across The World

September 17, 2021

Celebrating 10 Years of Therapy

September 10, 2021

“We Don’t Consider This a Conflicting Investment”

August 30, 2021

Most Startup ‘Pivots’ Aren’t Really Pivots, They’re Just What Startups Are Supposed To Do

August 22, 2021

If You’re Not Sure Whether Your Current Investors Would Give You More Money, The Answer Is Likely…

August 14, 2021

Future of Work Software That Focuses on EQ Not Just IQ

August 07, 2021

‘Inside Rounds’ Used to Be Bad. Sequoia & WhatsApp Changed Venture Forever

July 31, 2021

Tech Reporters, You’re Being Played By Using “Oversubscribed” To Describe Successful Funding Rounds

July 26, 2021

“I Can Really See Us Leading This Funding Round” Isn’t a Term Sheet

July 17, 2021

We Don’t Talk Enough About Money In Silicon Valley, Revisited

July 09, 2021

2 1/2 Angel Investing Mistakes You Can Easily Avoid

June 29, 2021

End of an Error: As Conan O’Brien Wraps Up 28 Years of Late Night, I Was an Idiot to Leave the Show

June 26, 2021

Don’t Let Your Best Product Managers All Become People Managers Or Your Company Will Suffer

June 18, 2021

We Raised $50m+ To Back New Venture Capitalists Who Don’t Look Like Me

June 12, 2021

Are Hiring for Merit & Prioritizing Diversity Incompatible at a Fast-Growing Startup? (Answer: No)

June 07, 2021

New Grads: Midstage Startups Are Your Best First Job in Tech

May 23, 2021

How Pro Skateboarder Tony Hawk Made Me A Better Parent

May 12, 2021

The Great Talent Reshuffling of 2021 Has Begun

May 03, 2021

Employee Surveys Won’t Tell You Whether To Return To An Office Or Not

April 27, 2021

Digital Plastic Surgery: Why Boys and Girls Use Filters Differently

April 13, 2021

Succeeding in Venture Capital as an Introvert

March 16, 2021

Why Facebook’s Responsible A.I. Team Needs To Be Able To Lose Money in Order To Do Its Job

March 15, 2021

“Oh, Your Algorithm Update Lowers Revenue & Decreases Usage? Ship it!”

March 15, 2021

Back After 10 Years, Turntable.fm Reminds Me How Much Fun The Web Can Be

March 09, 2021

Turntable.fm Reminds Me How Much Fun the Web Can Be

March 09, 2021

The Baddest Band In Town

March 07, 2021

A Year of Zoom Genitals, Bourbon Bottles & Child-Rearing

March 01, 2021

Why There’s No Such Thing as a ‘Startup Within a Big Company’

February 17, 2021

Why There’s No Such Thing as “A Startup Within a Big Company”

February 17, 2021

Three Types Of Startup Advisors You Might Not Have Thought About (But Which Will Help You Win)

February 08, 2021

Three Types Of Startup Advisors You Might Not Have Thought About (But Will Help You Win)

February 08, 2021

This Is The Single Most Important Page On The Web (If You’re a Human)

January 25, 2021

Don’t Just Stand With Someone Being Harassed. Stand In Front Of Them.

January 17, 2021

I Just Got Paid For Work I Did 20 Years Ago.

January 11, 2021

Instagram, YouTube & TikTok Are Burning Out Their Creators. Here’s How to Fix That.

January 04, 2021

Why I Worry About Venture-Backed Mental Health & Addiction Startups

December 28, 2020

Manager OKRs, Maker OKRs: How Startups Should Think About Goal-Setting

December 21, 2020

Leaving SF? Bring The Best of SV Values With You, Not Just SV Dollars

December 17, 2020

What Happened When I Deleted Every Meeting From My Calendar

December 14, 2020

How To Grade This Week’s airbnb and DoorDash IPOs

December 07, 2020

What To Do If You’re a Startup CEO & You Don’t Know How To Sell

November 30, 2020

The Bad Habit That Even Productive People Keep Falling Into

November 28, 2020

Even Productive People Make This Common Mistake

November 28, 2020

Why a Paid Newsletter Won’t Be Enough Money for Most Writers (And That’s Fine): The Multi-SKU…

November 22, 2020

Working In Tech & Worrying About Getting “Too Old”

November 15, 2020

Me! Talking Tech, Politics and TikTok with Alex Kantrowitz

November 12, 2020

The Essential Nature of In-Person Work For Early-Stage Startups

November 10, 2020

Is It Fair To Tell Founders “Just Execute And You’ll Be Fine?”

November 05, 2020

Never Become The Person Your Twitter Followers Want You To Be

November 02, 2020

“No Free Lunches” And Other Advice Our Parents Gave Us

October 28, 2020

Coinbase’s Culture Memo: Not Good, Not Bad, But I Reject ‘Mission-Focused’ Framing

October 26, 2020

You’ll Need At Least Two of These Four Qualifications to Get Hired By a Venture Firm

October 22, 2020

“Coming for the Content, Staying for the Community” Started With Video Games (Or Maybe Religion?)

October 19, 2020