Should leaders be judged on outcomes alone, or should context and reasons for failure be weighed?

Reid Hoffman · Dec 7, 2020 · hedged

Passing on Stripe is a call he regrets, yet it is not clear it was actually the wrong investment decision given the payments risks he knew and the small percentage offered at a high pre-money valuation

The risk/reward required a higher ownership percentage to justify joining the board, though the founders turned out to be magnificent

Scope: regrets the outcome; judges the decision process defensible on the information he had; admits he was wrong about the valuation being too high

33:26 20VC: Reid Hoffman on Investing in Airbnb and Passing on Stripe, The Different Styles of Truly Great Leaders, How To Think Through Ownership and Price in Venture & How To Ensure Venture Partnerships Always Have Trust and a Learning Mindset

Jeff Jordan · Jan 16, 2023

Passing on DoorDash was the right decision on the information available, even though it worked out badly

His thesis was that food delivery had no defensible barrier to entry and would end with restaurants taking orders from everyone on 20 iPads; he couldn't have anticipated Travis being capped at Uber Eats or the industry consolidation that followed

Scope: outcome was bad; process judged separately from outcome

41:07 20VC: a16z's Jeff Jordan on The Ultimate Guide to Investing in Marketplaces, Two Core Features to Look for in All Marketplace Investments, Why Fragmented Supply is so Important & Lessons from Airbnb, Pinterest and Instacart on What Makes the Best Cohorts

Roger Ehrenberg · Feb 19, 2024

Exit decisions should be judged by the quality of the process and trade-off analysis, not by hindsight outcomes

Hindsight lets you overfit a curve to find the optimal path, but that isn't real life; if you were thoughtful about context and trade-offs, it is what it is

40:51 20VC: Why VC Returns Will Get Worse, Why LP Incentive Structures are so Broken, What is the Answer to Liquidity with No M&A or IPOs, When to Sell vs Hold Your Winners & Turning $5M into $250M with The Trade Desk | Roger Ehrenberg, Eberg Capital

Klaus Hommels · Nov 27, 2024

Selling King.com early was a defensible call at the time, because Candy Crush did not yet exist and it was a very different company

The company that later justified a $5B+ valuation had not yet been built when the sale decision was made

Scope: judged as of the time of the decision, not in hindsight

56:43 20VC: Why Price Sensitivity is BS | Why "Portfolios" are Merely a Construct to Make LPs Happy | Why the Best Investment Never Happen in "Fundraising Rounds" | What Europe Needs to do to Become a Superpower Again | Klaus Hommels, Lakestar

Peter Singlehurst · Mar 19, 2025

Not all bad investments are mistakes: losses from a known uncertainty manifesting are part of investing, whereas mistakes are cases where you failed to see or properly weight something

Investing is estimating probabilities about the future, so negative outcomes on consciously taken risks are part and parcel of the business

7:41 20VC: The 10 Question Framework a $217BN Manager Uses to Make Investment Decisions | Lessons from Turning Down Stripe, Coinbase and Losing Money on Northvault | The Bull Case for Bytedance | How Anduril Could Be a $200BN Company with Peter Singlehurst

Harry Stebbings · May 27, 2025

A VC on Airwallex's board at the time would have been justified in supporting a sale to Stripe at $1.2BN

The company was only doing about $2M of revenue at the time, so the offer was extraordinary relative to the business

Scope: judged with the information available then, not with hindsight

68:54 20VC: The Most Insane Story in Startups: Airwallex: The Angel That Turned $1M into $1BN | The Fund That Pulled a Term Sheet & Lost $1BN | Rejecting Stripe's $1.2BN Offer | Scaling to $1BN in Revenue & 100% YoY Growth for 8 Years with Jack Zhang

Larry Aschebrook · Jun 16, 2025 · hedged

It is easy to call the Getir outcome obvious in hindsight, and it may have been obvious to observers from afar, but it wasn't from inside

62:33 20VC: How We Made $800M on Coursera | We Lost Money on Uber and Made Money on Lyft | We Did 3x on Postmates in 18 Months | DPI is King, MOIC is BS | We Dodged Theranos and I Still Lost Millions with Larry Aschebrook @ G Squared

Oren Zeev · Feb 2, 2026

A good decision maker must have the intellectual honesty to change their mind when new information arrives, rather than treating new information as self-validation — though he admits he still makes follow-on mistakes, such as doubling down on a prop-tech company just before the market turn

Like poker, you can make the correct odds-favoured decision and still lose the pot; luck dominates individual cases and over-correcting teaches the wrong lesson

Scope: concedes in hindsight he was not aggressive enough in stress testing; does not conclude he should be more conservative next time

20:08 20VC: 50% of Funds Will Go Out of Business | Why Growth Expectations Today are BS and Will Not Last | Why Oren Zeev Takes $0 Management Fees But 30% Carry | Why GPs Should Not Tell LPs Their Strategy

Alan Chang · Jan 5, 2026

Excuses are irrelevant for anyone leading an area of a company: success earns all the praise, failure earns all the blame regardless of the reason

Ownership of an area means owning the outcome, not the explanation for it

Scope: applies to leaders of an area of the company

0:00 20VC: $0-$260M in Revenue in Three Years: How We Did It | You Need to Work Weekends to Win — Most Founders Aren't Ambitious Enough | The Revolut Playbook: Speed, Urgency, Extreme Ownership, and Zero Excuses with Alan Chang @ Fuse Energy

Alan Chang · Jan 5, 2026

For anyone leading an area of a company, excuses for failure do not matter — they take all the praise for success and all the blame for failure regardless of the reasons

Per the Jobs janitor-versus-VP story Nik Storonsky sent him: a janitor's reasons are acceptable, but somewhere between janitor and VP reasons stop mattering

Scope: applies to leaders, not junior staff

34:21 20VC: $0-$260M in Revenue in Three Years: How We Did It | You Need to Work Weekends to Win — Most Founders Aren't Ambitious Enough | The Revolut Playbook: Speed, Urgency, Extreme Ownership, and Zero Excuses with Alan Chang @ Fuse Energy

Harry Stebbings · Jun 16, 2025

It was obvious at the time that Getir was going wrong — enormous cash into a business before it was ready, premature scaling, and unit economics that didn't work

The scale of capital deployed relative to the business's readiness and broken unit economics

62:22 Warning signs were visible in real time not only in hindsight