Serial entrepreneur and philanthropist best known as co-founder and CTO of travel search engine Kayak, acquired by Priceline for $1.8B in 2012.
Paul English says Kayak, his biggest hit, sold for $2 billion to Booking.com (Priceline). It is one of six companies he has sold in a row.
“$2 billion. I've actually sold 6 companies in a row, including Lola. I've sold even another one after Lola, Moonbeam, which is a podcast app. And now I'm on to my 7th company.”
Co-founder Steve Hafner noticed at Orbitz that 70% of users searched on Orbitz then opened a second browser to buy directly from the airline. Kayak's insight was to do only the search and hand users off to the airline to book.
“My co-founder Steve Hafner was one of the founders of Orbitz, and he had observed at Orbitz that 70% of the people did a search on Orbitz, but then when they were done, they opened a second browser and went directly to united.com, wherever to buy the ticket. And so Orbitz did all the searching for people but never made money. And so Steve basically said, why don't we create a company where all we do is search, and then if someone wants to go to United, they click the link and we'll send 'em directly to United and they could buy a fare.”
English ran Kayak for 10 years, took it public in 2012, then sold to Priceline. He left because he was bored and had built a tech team strong enough to run UI, product, and architecture without him.
“And I just frankly was bored. I felt like I was editing the flight screen for 10 years and I wanted to try something new. And I'd had an unbelievably strong team at tech leadership at Kayak. So at that point I felt like I could sneak out without hurting the company because I had people at that point that could do UI, they could do product, they could do architecture. So it gave me the freedom to try something new.”
Despite a 30.5% IRR across 60 investments, English passed on YouTube (met the founders via Moritz), Snapchat at an $80M valuation, and Dropbox (met Drew early), the last because he feared security problems.
“I have, I have some famous misses. I mean, I've been very lucky as an investor. I think my IRR is 30.5% over the last several years. So I'm doing pretty good. I've invested in 60 companies, but I've missed some. I missed Snapchat. I met one of their founders when they were financing at an $80 million valuation. That would've been a big outcome. Dropbox, I met Drew early on.”
English backed the Ksplice/Zula team across multiple startups. By the time they started Pilot, he asked to invest before he knew the idea and wrote a blind check at a $30M valuation that became a 40x as Pilot hit ~$1.2B.
“So I wrote them a check before I knew what they were doing. And that's a 40xer. I think I financed some— I wrote a check as part of their round at $30 million valuation. And I think their last valuation was like $1.2 billion or something. But that's one that the founding team had the mojo. So when you met them, you just knew those guys were going to create something serious. They were intense, high energy. They laughed a lot. They finished each other's sentences. They just really enjoyed working together.”
English's new startup Deets argues online reviews are broken: you can buy 1,000 fake 5-star Amazon reviews from PhD-run firms evading bot detection, and Yelp/TripAdvisor reviews come from people whose taste you don't share. Deets surfaces only recommendations from your friends, chosen influencers, and ML-matched lookalikes.
“What we're doing is we're saying online reviews are broken. You know, if you go to Google right now and in quotes you search for buy Amazon reviews, you'll see this 37,000 pages that tell you how to do that. If you make, you know, these headphones I'm wearing, if you make a competitor of these and you want to sell it on Amazon, You can easily buy 1,000 5-star reviews for that if you want. And these fake review companies are run by PhD computer scientists. They're evading Amazon's bot detection.”
Steal thisReplace anonymous star ratings with recommendations from people whose taste actually matches yours.
English's new startup Deets argues online reviews are broken: you can buy 1,000 fake 5-star Amazon reviews from PhD-run firms evading bot detection, and Yelp/TripAdvisor reviews come from people whose taste you don't share. Deets surfaces only recommendations from your friends, chosen influencers, and ML-matched lookalikes.
“What we're doing is we're saying online reviews are broken. You know, if you go to Google right now and in quotes you search for buy Amazon reviews, you'll see this 37,000 pages that tell you how to do that. If you make, you know, these headphones I'm wearing, if you make a competitor of these and you want to sell it on Amazon, You can easily buy 1,000 5-star reviews for that if you want. And these fake review companies are run by PhD computer scientists. They're evading Amazon's bot detection.”
Steal thisReplace anonymous star ratings with recommendations from people whose taste actually matches yours.
English credits TikTok's lookalike/user-clustering as his inspiration for Deets: it figured out his interests (bass players, dogs, gardening) and matches him to strangers with the same weird taste, all without a single onboarding question.
“TikTok's an amazing app. They don't ask you any questions. They don't say, What's your interest? But if you look at my TikTok feed, there's a lot of bass players. I'm a bad bass player, but I like bass players. There's a lot of dogs. I have a new dog. There's gardening. TikTok has figured out the stuff I'm interested in and without ever asking me a question.”
English argues tech rarely kills startups anymore because the stack (AWS, open source) makes building easy. Companies die either from a founder implosion that creates a toxic culture, or from building a beautiful product for a rare problem nobody cares about.
“Companies fail today for one of two reasons. Either there's a founder implosion and they create a toxic culture and people like hate their boss and they hate working there and they all leave, which unfortunately happens all too often. They, they fail the culture code. Or number two, they built a nice product, but it's a rare problem that no one cares about. And unfortunately, a lot of founders have an itch to scratch, as you were saying earlier, Sam, and they get really obsessed about it. Like, I have this little problem, I'm going to work on it for 10 years. And they don't realize that not a lot of people have that same problem.”
Steal thisBefore obsessing over your itch, validate that many other people share the same problem.
English's core recruiting principle: recruit all the time and keep your spidey sense out everywhere, because your next great CMO might be at an event you attended for an unrelated reason.
“The main thing is just recruit all the time. Always, always be recruiting and always be trying to connect with people. And you might be going to a, you know, a coffee social to learn about why crypto is terrible. Or whatever, and you don't realize there's someone going to be there that will be your next unbelievable CMO. You weren't expecting to meet them, but if you always have your spidey sense out for looking for amazing people, and then once you see them, do whatever it takes to get them to come meet your team.”
Steal thisTreat every social event as a recruiting event and keep your antenna up for great people.
English's recruiting leverage rule: a founder can only get a candidate to show up, but a great first 5 hires will close every future candidate. He also asks every great hire if they know anyone even more amazing.
“And I've always said that the first 5 people hire you the next 50, who hire you the next 500. And it's one thing as a founder to convince someone to come meet your company,. But if you've been really good at recruiting that first 5, those 5 will close the candidate for you. When they meet those 5, they'll say, oh my God, I need to work with this team.”
Steal thisObsess over your first 5 hires; let them sell the next 50.
English owns about 300 domain names, each paired with a Google Doc describing the company idea behind it, and is willing to spend big to buy a great name.
“I own about 300 domain names and every domain name has a Google Doc associated with the idea for the company. Um, I'm obsessed with brand and names and I'm, and Dharmesh and I share this, that we're prepared, prepared to spend big money to buy a good name.”
Steal thisPark a domain for every idea and attach a one-doc spec to each.
English owns about 300 domain names, each paired with a Google Doc describing the company idea behind it, and is willing to spend big to buy a great name.
“I own about 300 domain names and every domain name has a Google Doc associated with the idea for the company. Um, I'm obsessed with brand and names and I'm, and Dharmesh and I share this, that we're prepared, prepared to spend big money to buy a good name.”
Steal thisPark a domain for every idea and attach a one-doc spec to each.
English wants to build a Twitter competitor modeled on TikTok's positivity: eliminate trolling and cruelty and flag misinformation (like 'COVID vaccine causes autism') without filtering out legitimate independent voices who need anonymity.
“And so what I want to do as a Twitter competitor is create the kind Twitter where there's no trolls, there's no cruelty, and then also deal with the misinformation. When you see a tweet that says COVID vaccine causes autism. Like, how do you smack that down? And I'm very interested in those two problems, getting rid of cruelty and flagging misinformation, but doing it without filtering out independent info.”
English paid $500,000 to acquire the Lola.com domain after a bidding war. The name is for sale again because Capital One, which bought the company, wanted everything rebranded as Capital One.
“We paid $500,000 to buy Lola. We were in a bidding war.”