Walmart paid $16 billion for a company that had never made a profit. They weren't buying our P&L. They were buying access to 1.4 billion consumers.
Google offered us $500 million in 2009. I said no. People thought I was crazy. But I believed Yelp could be worth more on its own — and it was, until Google decided to build their own version and embed it in every search.
We merged with Flight Club. A digital-first marketplace merging with the most legendary physical sneaker consignment store in the world. Online meets offline. That was the power move.
Visa tried to buy us for $5.3 billion. The DOJ blocked it. At the time it felt like a disaster. Then we raised at $13.4 billion. Sometimes the government does you a favor.
We went public at a $7 billion valuation. Then Naver bought us for $1.2 billion. That math hurts. But the company needed a global platform, and Naver had Asia. Sometimes selling is the right move even at a discount.
We acquired Penta in Germany. A French fintech buying a German fintech. Five years ago that would have been unthinkable. Europe's fintech ecosystem is finally acting like one market.
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.
Twitter bought us before we even launched. In hindsight, that was both the best and worst thing that happened to Vine. Best because we got distribution. Worst because we lost control.
UBS tried to buy us for a reason. The big banks know their model is dying. They just cannot cannibalize their own advisor fees fast enough to compete with us.
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.
Atlassian bought us because every Jira ticket, every Confluence page, and every Trello card could be better with a 2-minute video attached to it. We are not replacing their products — we are making them better.
Ten million baby boomers own small businesses they want to sell. There aren't enough buyers. That supply-demand imbalance is the biggest wealth-building opportunity of our generation — and almost nobody is talking about it.
Uber gave us their Elevate division because they realized building the aircraft was harder than building the app. We build both.
Voodoo acquired us for $500 million. Some say it was a bailout. I say it was a bet on the authenticity format having a future.
Short sellers said our AI does not work. Thoma Bravo paid $5.3 billion for it. I will let the market decide who was right.
Etsy paid 1.63 billion dollars for a thrift store app built in London. Not bad for something that started as a social experiment.
We had 13 employees when Facebook bought us for a billion dollars. Everyone said we sold too cheap. They were right.
Stripe acquiring us was the best outcome imaginable. Now we have the resources to build payments infrastructure for all of Africa.
IBM is acquiring us. It's bittersweet — great for shareholders, uncertain for the community. We'll see.
Microsoft buying us for $7.5 billion scared the community. We proved it was the right move by staying developer-first.
Amazon buying us for $970 million in 2014 looked expensive. It generates $2.5 billion in revenue now.
Zomato saw what we were building and paid $568 million. Quick commerce is the future of Indian retail.
Tata didn't buy us to shut us down. They bought us because online grocery in India is just starting.
The Solexa acquisition for $600 million was the decision that changed everything for Illumina.
Getir acquired us for $1.2 billion. Then Getir collapsed too. The entire category was a mirage.
$4.9 billion acquisition by Saudi Arabia. Mobile gaming is now a geopolitical asset.
$12.7 billion exit to Take-Two. Not bad for a company everyone wrote off in 2015.
Selling to Amazon was the right decision for the company. But I'd be lying if I said it didn't change everything.
Paying $7.3 billion for Grubhub at the pandemic peak was the most expensive lesson of my career.
Buying ClassPass was about owning both sides of the marketplace. We run the studios. ClassPass brings the customers. Together, that's an unbeatable combination.
Everyone said linear TV was dead. I said: The Weather Channel has 100 million households, decades of trust, and meteorological data that every airline and government needs. That is not dead. That is infrastructure.
This deal with Block is about scale. Together we can reach every corner of the world that Afterpay couldn't reach alone.
After we sold to Intuit, I thought I could change a $7 billion company from the inside. I was wrong. Large companies do not change from a single VP.
Gianni Versace was one of the greatest. His brand represents something the whole world knows. That doesn't come around twice.
The Shoppers acquisition was not about adding scale for its own sake. It was about where Canadians were going to go for healthcare. We needed to be there, and we needed to be there first.