All Episodes

Rapidly Growing Valuations Shouldn't Scare You Off

Reading Social Proof Is an Art Form

Social Proof Is a Valid Signal

Ask About the Metrics They're Not Showing You

It's Easy to Exaggerate Early Traction

Everything Is a Proxy for Traction

Early Winners Don't Always Make It to the Finish Line

Invest in the First Credible Mover

Monopolies Fall When Platforms Shift

A Lot of Great Tech Businesses Are Natural Monopolies

Great Companies Expand Their Markets

Invest in $0 Billion Companies

Invest in Pure Tech Companies

Raising Money Without Any Product Is a Red Flag

Product Is the Resume of the Team

Expanding Fast vs. Dialing in the Model

In PayPal's Early Days, We Lost Money on Every Transaction

Get the Operation Working at a Small Scale

'Tech-Enabled' Often Means Thin Margins

Startups Didn't Have to be Good at Accounting Until Software Ate the World

You Can't Optimize Profits If There Are No Profits to Optimize

Negative Unit Economics Create the Illusion of Success

Startups Are Susceptible to 'Happy Talk'

Mature Your Culture as You Grow

Nobody Wants to Give a Founder Tough Love

Founder Psychology Is at the Heart of Most Blitzfails

Culture Is a Macrocosm of the Founder's Psychology

Micro-Bubbles Are Constantly Building and Bursting

'High-Burn Startup Meets Macro-Shock' Is a Recipe for Blitzfail

Moving Fast May Mean You're Not Really Moving at All

Startups Are a Race to Get to Scale

Blitzfail: Why Startups Go off the Rails

Repeat Founders Don't Really Want to Start Over From Scratch

'First-Time Founders' Often Have Been Tinkering for Quite a While

Avoid Teams That Would Sell Early

Founders Almost Can't Be Referenced

Your Reputation Is Built by the Companies That Are Doing Poorly

Coachability Is Overrated

You're Not Investing in Nice People

Invest Only in Technical Teams

Invest in the Smartest Scientists in a New Field

Don't Fantasize About What You Would Do If You Were the Founder

You'll Get Less Money in Your Winners

You Can Give Every Deal One Fatal Flaw

The Best Deals Look Weird

Judgment Requires a Willingness to Be Unpopular

Are Good Investors Piling in the Round with You?

Pivots Mean Your People Judgment Really Matters

Judgment Is the Work You Do Before a Deal Arrives

Judgment Gives You the Winning Lottery Numbers

Everybody Thinks They Have Good Judgment

Founders Backing Founders

Be Non-Consensus Right

Be a Shadow Co-Founder

The Best Deals Come from Your Network

Don't Build a Brand in a Narrow Vertical

My Original Brand Was in Growth Hacking

There's Very Little Innovation in Venture Capital

You Can't Build a Brand by Aping Someone Else

You Need a Brand to Get into Hot Deals

Don't Let Deals Pass on You

Investing Takes Capital, Judgment and Dealflow

Being a Founder Your Entire Life Is a Tough Road

IPOs Are for the Last Investors in Line

You're Living Inside the Gold Mine

Living in a Tech Hub Is Half the Battle

Strong Opinions, Loosely Held

How to Angel Invest