Sep 27, 2021 · 1h 12m · how-i-built-this
KAYAK: Paul English
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this episode of How I Built This, host Guy Raz interviews serial entrepreneur Paul English, tracing his journey from a working-class Boston childhood and struggles with bipolar disorder to founding Boston Light Software and building Kayak into a $1.8 billion travel powerhouse.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Guy holds 34.4% of the talking time here. How this is scored →
Guy as informed peer 1.7 Guest teaching 0.5 Guest disagreement 0.1 Guy pushing back 0.1
speaking balance: gold is Guy, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 24:30 English recalling his explosive compensation fight at Netcentric
English describes forcing raises for underpaid engineers by getting signed proof from the CFO, triggering a fierce fight with the CEO that ended his tenure.
Hardest push from Guy ▶ 38:00 Raz questioning Hafner's sudden jump to 50/50 equityRaz expresses incredulity that Hafner immediately went from offering 4% equity to 50/50 based purely on an initial lunch meeting and handshake.
Biggest teaching moment ▶ 51:00 Embracing being merely a thin UI layer over complex enginesEnglish explains that when backend developers mocked Kayak for merely being a thin UI layer, he treated that observation as a compliment and core strategy.
Guy holds their own ▶ 57:30 Raz framing Kayak as a brand rather than a technology companyRaz synthesizes English's career arc, observing that a lifelong backend programmer succeeded at Kayak by building brand identity and UX rather than novel core technology.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Guy as informed peer | Guest teaching | Guest disagreement | Guy pushing back | Why |
|---|---|---|---|---|---|---|
| Listener Survey Announcement | 0 | 0 | 0 | 0 | Guy Raz delivers the standard podcast survey request, opening teaser clip, and narrative intro about serial entrepreneurship and Paul English's background. | |
| Boston Childhood and Mother's Miraculous Recovery | 1 | 0 | 0 | 0 | Paul English recounts his working-class upbringing in a large Boston family, his charismatic pipefitter father, and his mother's recovery from Myasthenia Gravis. | |
| Family Dynamics, School Struggles, and Boston Latin | 1 | 0 | 0 | 0 | Raz asks about Paul's schooling and church life; English describes his struggles sitting in classrooms and testing top scores for Boston Latin. | |
| First Computer and the Creation of Speed Games | 1 | 0 | 0 | 0 | English details getting his first Commodore computer, programming his first game Cupid, and licensing it for a small initial check before the publisher failed. | |
| College at UMass Boston and Early Career | 2 | 0 | 0 | 0 | English describes balancing full-time software engineering work during college at UMass Boston, marriage, and an unexpected promotion to VP of Marketing at Interleaf. | |
| Joining Netcentric and Assembling a Core Tech Team | 2 | 1 | 0 | 0 | English clarifies that he met key technical colleagues Bill O'Donnell and Paul Schwenk at Interleaf before bringing them to Netcentric, emphasizing the role of talent and luck. | |
| Confronting Mental Health and Bipolar Diagnosis | 1 | 0 | 0 | 0 | English openly discusses experiencing severe depressive and hypomanic states in his twenties, receiving a bipolar diagnosis, and his cautious relationship with medication. | |
| Leaving Netcentric and Mid-Roll Tease | 2 | 1 | 1 | 0 | English recounts his falling out with Netcentric's CEO over promised engineer salary raises, subsequently bootstrapping Boston Light Software and selling it quickly to Intuit. | |
| Navigating Sudden Wealth and Early Philanthropy | 1 | 1 | 0 | 0 | English explains feeling uneasy with sudden wealth after the Intuit sale, voluntarily giving away half his equity to staff engineers, and beginning his philanthropic efforts. | |
| Narrow Escape on September 11th and Impermanence | 1 | 0 | 0 | 0 | English recounts narrowly avoiding American Airlines Flight 11 on 9/11 due to personal frugality, reflecting on impermanence and his son's comforting words. | |
| Family Loss and Becoming Father's Caretaker | 2 | 1 | 1 | 1 | English details acting as his father's caretaker before meeting Steve Hafner over drinks at Legal Sea Foods, quickly negotiating a fifty-fifty co-founder split. | |
| Securing Funding and Assembling the Kayak Team | 2 | 0 | 0 | 0 | Raz and English review the initial fundraising from General Catalyst and English recruiting his core engineering team by granting equity and office location choice. | |
| Defining the Brand, UI Philosophy, and Mid-Roll Break | 2 | 1 | 0 | 0 | English breaks down the agency branding process with Wolff Olins, the rationale for choosing the palindrome Kayak over names like Lola and Rice, and early kayaker complaints. | |
| Launching Kayak and Building Direct Traffic | 2 | 1 | 0 | 0 | English explains the upside-down unit economics of early Google AdWords user acquisition and how word of mouth converted traffic into 70% direct navigation. | |
| Developing the Business Model and Staying Lean | 3 | 1 | 0 | 0 | English outlines leveraging Orbitz as a stalking horse to get direct airline merchant deals and leaning into being an ultra-lean UI skin over ITA Software. | |
| Scaling Up, Creative Mania, and Rapid Iteration | 2 | 0 | 0 | 0 | English discusses his manic late-night sketch iterations and playfully acknowledges the internal team joke of ignoring ideas until he asked twice. | |
| Prioritizing Simplicity and Speed over Tech Complexity | 3 | 1 | 0 | 0 | Raz and English reflect on building speed and simplicity over complex backend tech, the $1.8B Priceline acquisition, and English's discomfort with post-sale public attention. | |
| The Side Venture: Building GetHuman | 2 | 1 | 0 | 0 | English describes creating GetHuman, launching Lola right as his non-compete expired, pivoting to spend management during COVID-19, and color-coding his schedule. | |
| Reflections on Success, Recruiting, and Luck | 2 | 1 | 0 | 0 | Raz asks the signature luck vs intelligence question; English breaks it into equal parts work ethic, creativity, recruiting, and luck, and shares driving Uber to test rating mechanics. |
Statements from this episode (18)
English licensed his teenage video game for $25,000 but the publisher folded
“The deal was, it was 25,000 dollars up front, and then a dollar revenue per game cartridge, which sounds really great, especially for a teenager. The bad news is, I licensed the game to them, and they immediately went out of business.”
English walked away from $1M in unvested Interleaf equity at age 29
“I made I made my first million when I was, I have to do the math, but I think I was 29 years old. But I remember after I had vested half my options, which is a million dollars, I then got convinced by a very gregarious recruiter in Boston to leave my big fancy…”
Paul English was diagnosed with bipolar disorder in his twenties
“And I went to see a psychiatrist at Newton Wellesley Hospital. They had diagnosed me as bipolar.”
Meds, meditation, and therapy kept English free of depressive episodes for decades
“And I have not had a depressive, like a full-on depressive episode in 20 years now, so I'm hoping, knock on wood, that I've licked that with the meds and with other, ah, with meditation and therapy has helped me with that.”
English forfeited $10 million of his Intuit acquisition payout to his engineers
“When we sold it that soon, I felt bad the engineers didn't make enough money. So Carl and I canceled half our stock and just gave it to the engineers. So instead of making twenty million, I only made Ten million.”
English avoided a hijacked 9/11 flight to save his employer money
“I think flight 11 was, if I remember correctly, it was 1418 hundred dollars, and it was a corporate travel department that Intuit had the book flight, so it wasn't my money, but I grew up frugal, and so I didn't want to spend that much of the company's money, …”
Hafner agreed to a 50-50 Kayak equity split on the spot
“He said, what would it take to have you join me as co-founder? I said, at a minimum, fifty-fifty. Just kind of joking. And he put his hand across the table, and he said, done.”
Kayak launched with $5M from General Catalyst and $2M from its founders
“General Catalyst put in five million, Steve put in a million, I put in a million, and then we started Kayak, and the middle thing we did, immediate thing we did was start recruiting.”
English: Early Expedia was 'seizure-inducing' and cluttered with excessive animation
“To me, Expedia was epileptic, seizure-inducing. I mean, it was really terrible. There was so much animation and graphics and so much stuff going on the website.”
Kayak founders wanted to name the company 'Lola' but lacked the domain
“And the first name, the one we really wanted, which we tried to buy, and we could not buy the domain name, was Lola.”
Early Kayak scraped airline websites without permission to build its inventory
“So originally Kayak had no revenue. And also we were scraping these websites without their permission. It's one of these things sort of ask for forgiveness, not permission.”
Kayak initially lost 80 cents per transaction on paid user acquisition
“In the early years of Kayak, it cost us about a dollar on average to buy someone to come to our website from us spending money on Google AdWords or other websites. We made on average 20 cents per user, so we were losing 80 cents a transaction in large numbers.”
Eventually 70% of Kayak's traffic came directly from users typing the URL
“It got to the point where 70% of the traffic on kayak was self-directed, meaning someone typed kayak.com in their browser”
Kayak used Orbitz as a stalking horse to secure direct airline deals
“And we use Orbitz as a stalking horse to get all the airlines to pay us directly, so we could send people directly to the airline sites.”
Kayak reached $300M in revenue with just 200 employees at its IPO
“When we took it public in 2012, we only had 200 employees, which is pretty small for a public company, and we had three hundred million in revenue. So it was one and a half million per employee.”
Over half of Kayak's 200 employees became millionaires at the 2012 IPO
“We had 200 employees. Over half of them became millionaires that day.”
English plans to launch multiple bootstrapped companies yearly instead of VC-backed startups
“I think for the rest of my life, Rather than doing a VC-backed company, I think what I might do is just have fun with these creative outputs and try to crank out, like, two to three or four companies a year, because the most fun for me in starting companies is…”
English drove for Uber to experience customer ratings before rating Lola staff
“Before I inflicted that upon our customer service people, I wanted to show that, okay, I'm happy to get rated. I want to see what it feels like to get rated. Being an Uber driver was the easiest way to do that because you get real-time feedback in the driver a…”