FAILURE

In school we learn that mistakes are bad. In the real world, I pay people for their mistakes. That is where the experience lives.

Failure is an option here. If things are not failing, you are not innovating enough.

It is fine to celebrate success but it is more important to heed the lessons of failure.

Getting fired from Facebook was the best thing that ever happened to me. I just did not know it for a few years.

I failed 13 businesses before 21. Every failure taught me what not to do. That education was priceless.

Every successful person I know has been through failure. The difference is they got up faster than they fell.

It doesn't matter how many times you fail. You only have to be right once.

I failed at my first business at 16 and lost $5,000. Best money I ever spent.

There's a silly notion that failure's not an option at NASA. Failure is an option here. If things are not failing, you are not innovating enough.

Failure is an option here. If things are not failing, you are not innovating enough.

I failed at making video games twice. Both times, something better came out of it.

When you invest twelve minutes and the guy wants a billion, you're going to lose big or win big.

I made decisions that were not in the best interest of the company. I own that.

I failed at 20 startups before Instacart. The secret is that each failure taught me what not to build. Instacart was the first thing I actually needed myself.

Zenefits taught me everything about what not to do. Rippling is the version built by someone who already made every possible mistake.

I got fired from my own company. Most people would have given up. I started a better company six months later. Failure is information, not identity.

I never feared failure. If you fear failure, you will never attempt something great. I have failed many times. Each failure taught me something the classroom never could.

Failure is a feature of doing important things, not a bug. If you're not failing a lot, you're not trying hard enough.

We lost a fund in the dot-com crash. I'm not proud of it, but I'm not ashamed of it either. We learned from it and built something much better afterward.

I've been wrong on most of my investments. The ones I was right on just happened to change the world.

I got rejected from Harvard ten times. I got rejected from KFC — they hired 23 people and I was the only one rejected. Rejection is just part of the story.

If I did it again, I'd start with one city, not fifteen. We scaled before we figured out the math. Classic mistake.

Everyone told us we were the future of car buying. Turns out the future needed better margins than we had.

The used car market is a $700 billion industry built entirely on mistrust. We thought transparency alone would be enough to win. We were wrong about the economics.

We were spending $2,400 to acquire each customer. You can't sell a used Honda Civic at those unit economics and survive.

We had the product. We had the demand. We just didn't have a business model that worked. That's a different kind of failure — the most frustrating kind.

I raised $850 million to prove that electric cars could work for everyone. We proved they could. We just couldn't prove we could make money doing it.

The vision was right. The timing was right. The execution was a disaster. That's the hardest lesson — being right about the future doesn't save you.

Israel was supposed to be our proof of concept. A small country, short distances, high gas prices. If it didn't work there, it wouldn't work anywhere. It didn't work there.

I dropped out of high school to start a business. Then I went bankrupt at 21. Then I built a $31 billion company. The dropout part is not the lesson. The bankruptcy part is.

People will write case studies about us. $120 million in funding. $600K in revenue. It's going to be in business school textbooks under the chapter called "What Not To Do."

I was building a product that the market didn't need as badly as I thought. The checkout problem was real. The willingness to pay for a solution wasn't. That's the lesson.

We shut down on a Tuesday. 400 people lost their jobs. I'd moved my family from Australia to San Francisco for this. It was the worst day of my life.

We raised $120 million, hired 400 people, and were doing $600,000 a year in revenue. I know how that math looks now. At the time, it felt like we were about to break through.

We went from a $32 billion valuation to bankruptcy in ten days. I genuinely did not think that was possible. I was wrong.

Effective altruism is about maximizing the good you can do. I thought building a massive company was the fastest way to generate the capital to give away. I was wrong about a lot of things.

Daishin and I failed at our previous startup — a food delivery app. We were two years too early. With GOAT, the timing was perfect. Sometimes the only difference between failure and a unicorn is timing.

We raised $200 million total. The board found out the metrics were fake and shut the company down in a week. From unicorn to dead in seven days.

SoftBank valued us at $1.2 billion. A billion dollars for what turned out to be an app with one million real users and nineteen million bots. That's $1,200 per real user.

We reported 20 million monthly active users. The SEC found that 95% of them were bots. Ninety-five percent. I don't know how to explain that in a way that sounds good.

The UP fitness band was supposed to be our future. We sold millions of them. But Fitbit sold tens of millions. And Apple was coming. We were stuck in the middle — too premium for mass market, too small for Apple.

We tried to be a speaker company, a wearables company, and a health data company all at once. We were good at all three and great at none. That's how you burn a billion dollars.

We raised $930 million. Nearly a billion dollars. For a hardware company that never figured out how to make a profit on a single product. That's a special kind of failure.

I started this company in 1999. It lasted 18 years. We went through Bluetooth headsets, speakers, fitness trackers, and clinical health. The pivot never stopped. Maybe that was the problem.

Our products won every design award. Every one. Red Dot. IDEA. IF. The products were beautiful. The unit economics were hideous.

I compared myself to Steve Jobs in an interview. I called juice "the internet of food." I understand now that those statements did not help.

We shut down 16 months after launch. The machine cost $400. The juice packs cost $7 each. And you could get the same result by squeezing them with your hands. I understand why people laughed.

Google Ventures, Kleiner Perkins, and Campbell Soup all invested. These are the smartest investors in the world. And none of them thought to squeeze the bag by hand before writing a check.

Bloomberg squeezed the packs by hand and got the same juice without the machine. That video killed us. One video. $120 million in funding destroyed by two hands and a YouTube upload.

SoftBank gave us $1.1 billion. With that kind of money, we expanded into everything — architecture, engineering, materials, factories, general contracting. We tried to own the entire stack. The stack won.

We opened factories in Phoenix, India, and Saudi Arabia simultaneously. We acquired architecture firms and lumber companies. We were building the plane, flying it, and redesigning it all at the same time.

Construction is local. Every city has different codes, different unions, different weather, different soil. A factory in Phoenix doesn't help you build in Boston. We learned that the expensive way.

We raised $2 billion and went bankrupt. The idea was right — construction needs disruption. The execution was a masterclass in how not to do it.

We said we had 100,000 pre-orders. The SEC found that most of them were non-binding expressions of interest, not real orders. There's a difference. We should have been clearer about that difference.

We went public via SPAC at a $1.6 billion valuation. We had no revenue, no production vehicle, and apparently no real pre-orders. The SPAC era will be studied for decades.

The Endurance truck had hub-mounted motors — one in each wheel. Revolutionary technology. We just never got to the part where we actually manufactured them at scale.

We filed for bankruptcy with $6 million in cash. We had raised over $1 billion total. A billion dollars in, six million left, zero trucks on the road. That math is hard to explain.

I'm a four-time founder. The first three didn't work. Mercury is the one that did. Four tries. That's what entrepreneurship actually looks like — nobody talks about the first three.

I founded MoviePass in 2011. It was a good idea at a fair price. Then Helios and Matheson bought it, dropped the price to $9.95 a month for unlimited movies, and turned my company into a bonfire.

Unlimited movies for $9.95 a month. A single movie ticket costs $15. Yes, we lost money on every customer. The plan was to make it up on data. The plan did not work.

We went from 20,000 subscribers to 3 million in six months. The growth was insane. The burn rate was more insane. We were losing $20 million a month.

They burned through $150 million of investor money subsidizing movie tickets. That's not a business model. That's a charity for people who like Marvel movies.

I told a conference that we tracked where users drove after the movie. The privacy backlash was immediate. I misspoke. But at that point, we were making a new mistake every week.

We sold dog food online and shipped 30-pound bags to people's doors. The shipping cost more than the dog food. We knew that. We thought scale would fix it. Scale did not fix it.

We had a Super Bowl commercial. A puppet sock dog. It was the most memorable ad of the year. Everyone loved the puppet. Nobody bought enough dog food to justify the $1.2 million we spent on the ad.

We raised $82.5 million in our IPO. Nine months later we shut down. From IPO to liquidation in nine months. That has to be some kind of record.

Amazon invested in us. Amazon. The company that would eventually dominate online retail invested in us and we still failed. That tells you how broken the model was.

The sock puppet is in the Smithsonian now. Our mascot outlived our company by 25 years. At least something survived.

Twenty years later, Chewy does exactly what we tried to do — sell pet supplies online — and it's worth $10 billion. We were right about the market. We were just 15 years too early and $300 million too short.

I blame everything on COVID. The pandemic killed us. People say that's an excuse. Maybe it is. But launching a mobile video service the month everyone was locked at home with their TVs was genuinely terrible luck.

We shut down after six months and returned $350 million to investors. Most failed startups return nothing. We returned 20%. That's either responsible or the most depressing statistic I've ever shared.

I ran Disney Studios. I co-founded DreamWorks. I know entertainment. I raised $1.75 billion for Quibi and it lasted six months. Turns out I didn't know mobile.

We spent $1.75 billion and got 500,000 subscribers. Netflix spends that on three movies. For $1.75 billion, we should have just bought a small country. It would have had more users.

We had Spielberg, Guillermo del Toro, Chrissy Teigen, and Liam Hemsworth. The content was expensive and the content was good. People just didn't want to pay for content they could only watch on their phones.

Quick bites. Ten minutes or less. Premium content on your phone. The thesis was perfect for the subway commute. Then COVID happened and nobody was on the subway.

We raised $100 million from Bessemer, Canaan, and Coatue. Some of the smartest VCs in tech. They invested in an AI bookkeeping platform. What they got was a CPA firm with a website.

We told investors AI was doing the bookkeeping. Investors loved it. The problem was, humans were doing the bookkeeping. The AI wasn't ready. We shipped the marketing before we shipped the technology.

I'm a CPA. I know bookkeeping. I genuinely believed AI could automate it. But the technology wasn't there yet, and instead of admitting that, we hired more humans and called them AI. That was the mistake.

We had 500 employees doing manual bookkeeping while our pitch deck said AI handled 90% of the work. When Forbes started asking questions, there was no good answer.

We shut down in 2020. Laid off everyone. Returned what money we could. The lesson is simple: don't raise on the technology you plan to build. Raise on the technology you've actually built.

Every startup exaggerates a little. But there's a line between optimism and deception. I thought I was being optimistic. The market decided I was being deceptive. The market was probably right.

We designed a cylindrical solar panel that could capture sunlight from all angles without tracking the sun. The physics were beautiful. The economics were a disaster.

The Department of Energy gave us a $535 million loan guarantee. President Obama visited our factory. We were the poster child for green energy. Then we went bankrupt and became the poster child for government waste.

Chinese manufacturers dropped the price of flat solar panels by 75% in two years. We couldn't compete on price with our cylindrical design. The technology worked. The market chose cheaper.

We had a $6 billion pipeline of customer orders. On paper, we were thriving. In reality, every panel we sold cost more to make than we charged for it. Revenue was accelerating our death, not preventing it.

I was fired as CEO two years before the bankruptcy. The board replaced me with someone who was supposed to fix the cost structure. Nobody could fix a cost structure when your competitor's costs are falling 30% a year.

The FBI raided our offices. Congressional hearings. Criminal investigations. For a solar panel company. We didn't commit fraud — we just bet on the wrong technology at the wrong time. But try explaining that to a congressman on camera.

I raised $100 million and told investors we'd be the open-source AI company. The Linux of AI. That pitch worked beautifully in fundraising. It worked less beautifully in revenue.

We bought Livongo for $18.5 billion. At the time, it was the biggest digital health deal in history. Then our stock dropped 90% and suddenly it looked like the most expensive acquisition in history too.

I failed eight startups before Toss. Each one taught me what not to build. Toss was the first time I built something people actually needed every day.

We had 200 million monthly active users and Twitter still could not figure out how to make money from it. That is the saddest sentence in startup history.

Vine created an entire generation of creators — Logan Paul, Lele Pons, King Bach. They all left for YouTube and Instagram because we could not pay them. We had the talent and no business model.

We raised $300 million to build the fashion supply chain for Southeast Asia. The vision was right. The execution — well, clearly something went very wrong.

I became the youngest female CEO to run a company valued at over a billion dollars in Asia. And then I became one of the youngest to lose it all. Both titles are equally mine.

We grew to 400 employees and then ran out of money overnight. I mean literally overnight. One day we were operating, the next day I had to tell 400 people they no longer had jobs.

Everyone talks about failing fast. Nobody talks about the 400 people who lose their health insurance when you fail. That part keeps you up at night for years.

Zirtual got acquired by Startups.co 48 hours after we shut down. The brand and the customers had value. The business model did not. That is a very expensive lesson in the difference.

The mistake was simple — we were spending more on labor than we were charging customers. The unit economics never worked. I just refused to see it until the bank account hit zero.

I have been transparent about deals that did not perform. Interest rates went up, rents slowed down, and some of our projections were wrong. That is real estate. If someone tells you every deal works out perfectly, they are lying to you.

If you've never tried, how will you ever know if there's any chance? I failed the college exam twice, but here I am. You are not defined by your failures — you're defined by what you do after them.

I applied for 30 jobs and got rejected from all of them. I applied to KFC — 24 people applied, 23 got accepted. I was the only one rejected. So I applied to be a police officer — five people applied, four got accepted. I was the only one rejected.

Most companies die not because they made the wrong decision, but because they made the right decision too slowly. The cost of delay is invisible until it kills you.

I failed in London. I failed in some parts of America. I failed at running other brands. But I never failed at learning from failure. That's the only skill that matters.

One win, nine losses. That is the history of my career. The key is to make that one win so big that it pays for all nine losses and then some.

The Earn situation was the worst experience of our careers. We fight every day to get customers their money back. When you put your name on a product, you own the outcome — good or bad.

We ran ConsenSys like a venture studio for years — dozens of projects, most of them experiments. A lot failed. The ones that survived — MetaMask, Infura — became essential infrastructure. That's how innovation works: you plant a hundred seeds and water the ones that sprout.

Solana went down seven times in 2022. Each outage was painful and embarrassing. But we fixed the problems, improved the network, and came back stronger. The people who declared Solana dead were wrong — they confused growing pains for a death rattle.

Production yields were our Achilles heel. In the lab, our cells were world-class. On the factory floor, consistency killed us. The gap between prototype and production is where most hardware startups die. We were no exception.

We raised $15 billion. We had $55 billion in orders from BMW, VW, and Volvo. And we still couldn't make it work fast enough. Battery manufacturing is the hardest industrial challenge on Earth.

Failure and resilience are the hallmarks of every great career. I have had nine companies. Most of them failed. The ones that worked made everything worth it.

We lost $1.35 billion on Washington Mutual. It was a reminder that even after decades of experience, you can still get it catastrophically wrong.

I have invested in over 100 companies. Most of them failed. The ones that worked paid for everything plus a lifetime of lessons.

Terran 1 reached space but did not make orbit. We learned more from that one flight than from years of ground testing.

My dad used to ask at dinner: what did you fail at today? That taught me that failure is not the opposite of success — it is the path to it.

I got fired and used my severance to start a company. Getting fired was the best thing that ever happened to me.

I spent $1 billion running for president and lost. That is an expensive lesson in the limits of money in politics.

I have started over 400 companies. Most of them failed. But I only needed a handful of winners to become a billionaire.

Self-driving is a trust problem disguised as a technology problem. We solved the technology. We failed at the trust.

GM gave us $10 billion and told us to solve autonomous driving. We got close. Close is not enough.

The July 2024 outage was the hardest day of my career. We caused the very thing we exist to prevent — widespread disruption. We own that, and we will earn trust back.

Failure is the highway to success. Every time you fail you learn what does not work and you are closer to finding what does.

We need to accept that we will not always make the right decisions. We will screw up royally sometimes. Understanding that failure is not the opposite of success is part of success.

Failure is not the opposite of success. It is part of success.

Applied for a job at Facebook. Got turned down. Applied for a job at Twitter. Got turned down. That was a great day.

We have killed more games than we have shipped. And we are proud of that.

When we kill a game we celebrate with champagne. Failure is how you learn what not to do.

We got rejected from Y Combinator the first time. Applied again and got in. Persistence is underrated.

The iBuying experiment cost us $881 million in one quarter. That is an expensive lesson in humility. The algorithm does not know everything.

I applied to work at Facebook. They said no. I applied to Twitter. They said no. Best rejections of my life.

We spent 3.5 billion on an electric car and then killed it. The car worked beautifully. The economics did not.

The SPAC fell through. The funding dried up. But the lettuce kept growing. Vertical farming will work. Just not yet.

Each scooter cost 500 dollars. It lasted about 28 days in the wild. People threw them in rivers. The unit economics never worked.

We proved vertical farming can produce beautiful food. We just could not produce it cheaply enough to compete with a field in California.

Move fast and break things works for software. It does not work when the things you are breaking are actual physical scooters.

We raised 1.8 billion dollars to deliver groceries in 10 minutes. It works in Istanbul. It does not work in London.

Nine hundred million dollars and 500 employees. Gone in a week. That is how fast it happens in logistics.

We had 150 million users. Tiger Global invested. BlackRock invested. I thought we were invincible. Nobody is invincible.

Software cannot protect you from a freight recession. When there is nothing to carry the algorithm does not matter.

From 22 billion to zero. That is not a valuation correction. That is a lesson in what happens when growth becomes the only metric.

I built something incredible and I destroyed it through mismanagement. That is the honest truth.

We raised 900 million dollars to fix trucking. It turns out trucking breaks you before you fix it.

Jeff Bezos invested personally. When Bezos backs your logistics company you think you have figured it out. We had not.

We acquired Gorillas thinking consolidation would fix the economics. Combining two unprofitable companies does not create one profitable company.

We raised 852 million dollars. We hit a 4 billion dollar valuation. And the product did not work well enough. That is the whole story.

Tiger Global. General Catalyst. Vista Equity. The best investors backed us. Even smart money gets AI hype wrong.

Quibi lasted six months. 1.75 billion dollars. Zero lasting impact. I am still processing that.

I spent 144 million dollars of my own money running for governor and lost. That is the most expensive lesson in humility I ever received.

I have failed more times than most people have tried. That is not a motivational poster. That is my actual record.

There's no chance that the iPhone is going to get any significant market share.

My first company filed for bankruptcy. My second company got sold for not enough. My third company changed transportation globally. Persistence matters.

Do the one thing you think you cannot do. Fail at it. Try again. The only people who never tumble are those who never mount the high wire.

95% of coins will die, but there's entertainment in watching them die too.

We failed our creditors and our investors. I take responsibility for that.

I still believe in the long-term thesis for crypto. The execution was the problem, not the vision.

Going from the hottest company in America to a 97% stock decline teaches you everything about humility.

Our voice app failed. But the analytics tools we built to understand why it failed became a billion-dollar company.

We wanted to build the Model T of rockets. Cheap, frequent, reliable. Two out of three isn't enough.

Rocket failures on live video are humbling. But every failure teaches you something no simulation can.

Failure is just a stepping stone. The question is whether you step on it or sit on it.

Don't worry about failure; you only have to be right once.

Sears had the best brand in American retail. Somewhere along the way, we lost sight of the customer.

I generated 25% annual returns for a decade. Then I tried to run a retailer. Humility is a lesson, not a choice.

I've failed at making video games twice. Both times, I accidentally built a billion-dollar company.

iBuying was our most expensive lesson. Buying houses is not a tech business — it's a capital business.

$1.3 billion raised to deliver groceries on bicycles. The math never worked.

$8 billion SPAC valuation to zero. Cars are not software — every one is a unique snowflake of mechanical risk.

Buying, reconditioning, and delivering used cars costs more per unit than the margin on each sale.

We claimed 86% job placement. The real number was lower. That dishonesty destroyed everything.

47% efficacy versus 95% for Moderna and BioNTech. Same technology, different execution. That gap is everything.

$3 billion SPAC valuation to $50 million market cap. When the housing market turns, iBuyers turn to dust.

$647 million to build houses in a factory. Turns out the factory works. The business model doesn't.

$130 million raised, rebranded to BloomTech, then shut down. The idea was right. The execution was wrong.

Free education, pay only when you get a job. The incentives were perfect. The execution was not.

I owe $3.5 billion to people who trusted me with their money. That weighs more than any amount of money I've ever had.

Luna was supposed to be a stablecoin. A stablecoin going to zero was not in our risk models.

Twenty failures taught me more than one success ever could. Each dead startup showed me exactly what not to do next time.

I failed at 20 startups before Instacart. The only thing that changed was the idea. I was the same person.

My DUI arrests were the worst moments of my life. They were also the moments that finally forced me to ask for help.

Failure is not the enemy. The real enemy is the fear of failure that stops you from trying again.

I lost an election. Then I visited schools and saw almost no girls learning to code. The loss gave me a purpose bigger than winning.

I made mistakes. Big ones. Running a company for 16 years means you will. The question is whether you learn faster than the damage compounds.

Failure is not the opposite of success. It is part of success. Every year I failed in the playoffs, I learned something I used to win the championship.

I missed the shale revolution. Anyone who says they saw it coming at scale is lying or got lucky.

My first trade taught me everything. I made money, held on for more, and lost it all. Every trading lesson I know fits in that one story.

Losing $1.8 billion of someone else’s money teaches you things about risk that no MBA program ever will.

I spent 30 years building a reputation in healthcare investing. The math worked. The ethics didn’t, apparently.

The suicide nets were the darkest moment of my career. We failed those workers and it changed everything about how we operate.

Being fired was the best thing that ever happened to my bank account.

The Zozosuit was my biggest failure. But I would rather fail trying something nobody has done than succeed at something boring.

We had the money. We had the talent. We had two of the biggest automakers in the world. What we didn't have was enough time.

I failed at consumer delivery first. DoorDash for groceries in India doesn't work when order values are $3. B2B was the pivot that saved us.

The airline was a dream. Sometimes dreams are expensive.

Anaconda was my education. It was an expensive education, but I would not trade it. You learn more from failure than from anything else.

Success is not built on success. It is built on failure, frustration, and sometimes catastrophe.

Digg taught me what not to do just as much as what to do. Sometimes the most expensive lesson is the most valuable one.

Getting fired was the best thing that ever happened to me. It forced me to answer a question I had been avoiding: what do I actually want to build?

Failure is the universe telling you to try differently.

The idea that you have to fail to learn is overrated. You can also learn by succeeding — and then watching what breaks.

Every entrepreneur faces setbacks. What separates those who succeed from those who don't is how you respond when things go wrong.