❝Story01:30
Six Companies Sold in a Row, and the Seventh Underway
Paul English lists the six companies he has sold consecutively: Boston Light, an e-commerce storefront business sold to Intuit that made him VP of Technology there; Intermute, internet security software built with his brother Ed English and sold to Trend Micro; GetHuman.com, which served customer service information to over 200 million people; Kayak; Moonbeam, a podcast player; and Lola, a business travel and expense company. Kayak was the biggest financial outcome at roughly two billion dollars. He does not formally count a seventh, a software company he created in high school, though he says making money designing software as a teenager remains meaningful to him. He is now on his seventh company.
- Boston Light was a Shopify-like storefront business 20 years early, sold to Intuit
- Intermute was internet security software built with his brother, sold to Trend Micro
- GetHuman.com served customer service information to over 200 million people
- Kayak was the largest financial outcome at roughly two billion dollars
- He excludes a high school software company from the count despite its personal significance
“I've actually sold six companies in a row, including Lola. I've sold even another one after Lola, Moonbeam, which is a podcast app. And now…”
“Kayak was the biggest financial outcome, which I'm deeply appreciative, and I learned a lot at Kayak.”
#serial-founder#exits#kayak#startup-history
❝Story03:00
Kayak's Origin: The 70% Orbitz Leak and Expedia as Bloatware
Kayak is the only one of English's companies that was not his own idea. Co-founder Steve Hafner, previously a founder of Orbitz, had observed that 70% of people searching on Orbitz would finish, open a second browser, and go directly to united.com to buy the ticket, meaning Orbitz did all the searching and captured none of the revenue. His proposed fix was a company that only searches and then hands the user off to the airline via a link. English and Hafner met by chance and decided to co-found within roughly 45 minutes, each putting a million dollars into the original round. English then took ownership of product, spent about an hour on market leader Expedia that night, and concluded the next morning that it would not be hard to beat.
- 70% of Orbitz searchers opened a second browser and bought direct from the airline
- The fix was to do only search and hand the user off via a link
- English and Hafner agreed to co-found within about 45 minutes of meeting by chance
- Each founder put one million dollars into the original financing round
- English judged Expedia to be seizure-inducing bloatware after one hour of use
“he had observed that Orbitz that 70% of the people that are searching on Orbitz, but then when they were done, they opened a second…”
“Cuz I looked at Expedia as bloatware. It was sort of seizure-inducing. There was so much stuff going on the screen.”
#kayak#co-founders#product-strategy#travel
❝Story04:30
Why He Sells: Ten Years of Editing the Flight Screen
Asked why he sells rather than holding companies the way Dharmesh Shah has held HubSpot, English says Kayak was his longest stint at ten years, including taking it public in 2012 and selling shortly after to Priceline, the parent of Booking.com. His reason for leaving was simple boredom: he felt he had been editing the flight screen for a decade and wanted something new. What made the exit possible was the strength of the tech leadership team he had built, with people who could own UI, product, and architecture, so he could leave without hurting the company. His first company was financed by blowing through his 401k, but by the time of Kayak he had sold a company for 30 million and could afford the million-dollar founding check comfortably.
- Kayak was his longest run at ten years, IPO in 2012 then sold to Priceline
- He left because he was bored of editing the flight screen
- A deep tech leadership bench let him exit without damaging the company
- His first company was financed by burning through his own 401k
- A prior 30 million dollar exit made Kayak's million-dollar check affordable
“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.”
“I just sold a company for 30 million, so I could have the the million wasn't that hard for me at that point.”
#exits#founder-psychology#team-building#kayak
❝Story06:30
The Famous Misses: Airbnb, YouTube, Snapchat, Dropbox
English catalogues the deals he saw early and passed on. He met Brian Chesky when Airbnb was financing at a one billion dollar valuation and found him iconic, passion-driven, serious, intense and charismatic, but could not see how many people would want strangers living in their house. At Sequoia's office, Mike Moritz introduced him to Chad Hurley and Steve Chen as guys putting videos online, and English thought it was merely cool. He met a Snapchat founder when they were financing at an 80 million dollar valuation. He met Drew Houston early and passed on Dropbox because he believed it would be plagued by security problems, a concern he still holds given that Dropbox does not meaningfully encrypt user files.
- Passed on Airbnb at a one billion dollar valuation, now worth roughly 100 billion
- Met the YouTube founders at Sequoia via Mike Moritz and did not see it
- Met a Snapchat founder at an 80 million dollar valuation
- Passed on Dropbox over security concerns he still holds today
- Read Chesky correctly as an exceptional founder but misread the market size
“I said, "This seems awesome for people who want to have strangers living in their house, but how many people are going to second to…”
“I missed Snapchat. I met one of their founders when they were financing at an 80 million-dollar valuation. That would have been a big outcome.”
#angel-investing#misses#pattern-recognition
❝Story33:30
Bipolar and Proud: The Bipolar Social Club
English was diagnosed with bipolar illness at 25 and is candid that it is a serious condition where people end up losing marriages, jobs, and lives. He has bipolar two rather than the more severe bipolar one, and says it took him a good ten to fifteen years to learn how to manage it. Rather than hide it, he built bipolarsocialclub.org, a video series where ten people with bipolar illness tell their own journey, aimed at de-stigmatising the condition by acknowledging both the genuinely bad parts and the funny ones. He wants to extend it into a clothing brand so people can wear it proudly, comparing his ability to spot another bipolar person across a crowded room to what gay friends call gaydar. He notes some people still cannot disclose because it would damage their careers.
- Diagnosed at 25 with bipolar two, the less severe of the two types
- It took him ten to fifteen years to learn to manage it
- bipolarsocialclub.org features ten people telling their own bipolar journeys
- The goal is de-stigmatisation by naming both the bad and the funny parts
- He wants a clothing brand so people can wear bipolar and proud openly
“I have bipolar illness. I was diagnosed at age 25, and it's a pretty serious illness. You know, a lot of people end up killing…”
“If you go to bipolarsocialclub.org, there's 10 people with bipolar illness who kind of tell their journey. And it's kind of de-stigmatizing it.”
#mental-health#founder-wellbeing#destigmatisation