How I Built This with Guy Raz

Episode: KAYAK: Paul English (September 27, 2021)

Episode Overview

In this episode, Guy Raz interviews Paul English, co-founder of KAYAK, about his journey creating the travel search engine and several other startups. English, a serial entrepreneur, opens up about his working-class Boston upbringing, grappling with mental health, his path through the Boston tech scene, and the thrill of building creative teams and products. The conversation delves deep into English’s philosophies on business, luck, design, and leadership, concluding with insights on philanthropy, innovation, and managing personal passions.

Key Discussion Points & Insights

Early Life and Upbringing

• Working-Class Roots: Paul English grew up in a crowded, working-class family in Boston, sharing a three-bedroom house with eight other family members. He reflects on the practicality and simplicity of his childhood.
  • “The brothers, the four boys slept in the attic which had no heat and no air conditioning. The worst part of it was we had one bathroom with nine people… but it was fine. Like we didn't know anything different.” — Paul English [07:43]
• Parents' Influence:
  • Father was a pipefitter for nearly 50 years—charismatic, strict.
  • Mother suffered from a debilitating muscle disorder but recovered through what she believed was a miracle.
  • “My father had really good influence and skills. He was very charismatic and very confident.” — Paul English [08:36]
• Marriage and Family: Married young, had two kids, remained close with them and his ex-wife after divorce.

Academic & Early Technical Interests

• Restless Student: Struggled with classroom settings, possibly had undiagnosed ADHD, but excelled in science and music competitions.
• First Computer: Mother bought a Commodore VIC-20, which sparked his interest in coding and led him to write his first video game, "Cupid."
  • “I selfishly took it over and I learned everything I could. I learned how to code, I wrote software, I wrote a video game. And that to me taught me like, whoa, this way to make money programming.” — Paul English [14:33]
• First Business: Sold his game to GBA for a brief payday (though the company went bankrupt before paying the full fee).

Early Career

• Diverse Experience: Worked for companies like Data General, wrote software for US Air Force spy planes, and explored different industries while completing his degrees at UMass Boston.
• Interleaf: Found real success here—learned both engineering and, unexpectedly, product marketing after being thrust into new management roles.
• First Startup Miss: Left Interleaf for the startup Netcentric, losing out on stock options, but gained valuable lessons on what not to do in a startup.

Mental Health Struggles

• Diagnosis: In his mid-20s, English was diagnosed as bipolar after experiencing alternating depression and mania—key to both his creativity and his challenges.
  • “I would go between these depressive episodes… and then manic episodes where I couldn't sleep. …I became detached from other people… I had trouble communicating.” — Paul English [23:56]
• Impact on Work: Initial treatment dulled his creative side, leading to cycles of starting and stopping medication for many years.
• Resolution: Found a balance of medication, meditation, and therapy; hasn’t had a major depressive episode in 20 years.

First Major Exit: Boston Light Software

• Bootstrap Beginnings: Founded in 1998, initially focused on e-commerce for small businesses, then pivoted toward invoicing and services.
• Rapid Acquisition: Sold to Intuit in about a year for $33.5 million, walked away with $8–10 million personally after splitting more with his team than originally planned.
  • “It was actually uncomfortable for me to have that money… so I started giving money away. And that began a journey where I spent a lot of hours a week on philanthropy.” — Paul English [34:16]
• Surviving 9/11 by Chance: Was booked on American Airlines Flight 11 on 9/11 but switched flights to save company money—his son later attributed the “save” to his grandmother’s spirit.

Meeting Steve Hafner & Founding KAYAK

• The Meet-Cute: Introduced by venture capital partners; after a lunch (and gin and tonics), Hafner impulsively offers English a 50/50 co-founder split on the spot.
  • “I said, at a minimum, 50/50. Just kind of joking. And he put his hand across the table and he said, done.” — Paul English [42:18]
• Team Assembly: Quickly brings on core engineers from his previous startups, offering much lower salaries but meaningful equity.
• Two-Office Model: Tech based near Boston, commercial in Connecticut—a rarity before remote work tools were common.

KAYAK’s Differentiator: Simplicity & User Experience

• Design Obsession: English focuses on building a "cleaner, simpler, faster" flight search engine—contrasts vivid, distracting competition like Expedia.
  • “The first day Steve and I met… I spent probably 10 minutes on Expedia… and I thought, this is not gonna be hard to beat this because… there was so much stuff going on.” — Paul English [47:31]
• Origin of the Name:
  • Brand agency selected "Kayak" (palindromic, short, evokes freedom).
  • “I liked the letter K… it meant like freedom. It's just like a great word. And it's very difficult in branding to take a word which means one thing and change it to mean something else. But if you're successful and you own that word, it's incredibly valuable.” — Paul English [48:12]
  • Received angry emails from kayakers about “stealing” the word. [49:33]
• Product Launch: May 2004 beta release, public later that year.

Business Model and Growth

• Lean, Profitable: Kayak starts with no revenue, scrapes data without permission, and slowly negotiates deals with airlines.
• Referral-Based Revenue: Instead of commissions for selling tickets, Kayak gets fees for referrals to airline and hotel sites.
  • “Originally Kayak had no revenue. And also we were scraping these websites without their permission…. It took us about a year, year and a half till the software felt really good. And then we started growing rapidly.” — Paul English [52:17]
• Word-of-Mouth and Brand Building: Spent money on Google AdWords, but focus was always on making the product memorable and easy to recommend.
• Team Size: Extremely lean—only 200 employees and $300 million revenue by IPO.
  • “It was one and a half million per employee. We were crazy profitable and fast growing.” — Paul English [56:20]
• Key Metric: Percentage of users coming straight to Kayak’s site—proof of powerful brand ("K" in Google autocomplete was “Kayak”).
• Role and Mental Health: Mania fueled productivity and creativity; had a culture of rapid iteration and was known for sending prolific idea emails, not all of which teams acted on.

Exit & Aftermath

• IPO and Acquisition:
  • 2012 IPO, then acquired by Priceline/Booking Holdings for $1.8 billion by the end of that year.
  • Majority of Kayak employees became millionaires from the deal.
  • “My first thought was always how happy I was for the team. …As far as the fame that came along with it, that gave me anxiety. I'm an introvert by nature.” — Paul English [63:09]
• Transition: Stayed to help transition business, then left; was not comfortable with fame or sudden wealth.
• Philanthropy: Channeled much of his wealth into nonprofit work and thoughtful giving.

Later Ventures & Life Philosophy

• Side Projects: Built GetHuman (customer service directory) during Kayak, runs it still via friends.
• Lola: After non-compete, launched Lola (spent management for business travel), adapting business model during the pandemic.
• Multiple Parallel Projects: Schedules life with a color-coded calendar to balance startups, non-profits, self-care, and family/friends.
• On Being an Uber Driver: Drove Uber to experience customer feedback firsthand and to lead by example.
  • “Being an Uber driver was the easiest way to do that because you get real time feedback. In the driver app, you get feedback every day about how your rating is.” — Paul English [73:29]

Notable Quotes & Memorable Moments

• “Many times I'd say, I have to go to detention. I said, I can't. I'm an altar, but I have to go to church. And they wouldn't believe me. …I'm still amazed...who came up with this idea to make kids sit in a chair at a desk for eight hours? It just seems crazy.” — Paul English [12:20]
• "I said, at a minimum, 50/50 [partnership]. ... And he put his hand across the table and said, done. And I thought, whoa, I like how bold this guy is." — Paul English [42:16]
• “We literally got hate mail from kayakers…who said this was terrible, that we took this over and this is like a blight on the Internet, you know, that someone would take over their precious hobby.” — Paul English [49:33]
• “Failure is okay. We built a lot of technology at COG that we threw away. …So that happened many times at Kayak.” — Paul English [60:11]
• "To build something simple takes years." — Scott Cook (quoted by Paul English) [61:42]
• “My success leads to maybe three things. I do think work ethic is a part of it. …I think the creativity is a part of it. …And then the third thing, which is probably the biggest: I love recruiting and I love being amazed by other creative people.” — Paul English [72:02]
• "Kayak was tremendous luck...I don't know. Maybe it's those four things. 25% each." — Paul English [72:58]
• “As kids say the most amazing things…my son said Mimi took care of dad to make sure he didn't get on the wrong plane today. And then he fell asleep.” — Paul English [36:22]

Segment Timestamps

• Early family and upbringing: [07:43]–[15:12]
• First computer/video game business: [14:33]–[16:58]
• College and early jobs: [17:01]–[21:00]
• Mental health and life changes: [23:56]–[27:15]
• Early startups & Netcentric: [21:37]–[29:08]
• Boston Light exit / 9/11 story: [30:25]–[36:49]
• Caretaking for parents, set up for Kayak: [37:13]–[39:54]
• Founding Kayak, team assembly: [41:15]–[46:00]
• Design/user experience focus: [46:20]–[47:38]
• Naming Kayak, public response: [48:12]–[49:45]
• First launch and business model: [50:29]–[53:59]
• Growth, partnerships, profitability: [54:00]–[57:32]
• IPO and sale to Priceline: [62:01]–[65:06]
• Philanthropy and discomfort with wealth: [63:55]–[64:48]
• Later businesses/side projects: [66:06]–[70:00]
• Personal philosophy, calendar balance: [70:28]–[71:40]
• Luck vs. hard work: [72:02]–[72:58]
• On being an Uber driver: [73:09]–[74:29]

Final Themes

• Creativity > Business: Paul English thrives on imagining, building, and iterating on products—constantly seeking "day one" start-up energy, rather than managing or scaling mature businesses.
• Product Simplicity: True innovation for English is relentless focus on clean, intuitive user experience, even if technical innovation is built atop others’ tech.
• Luck, Team, and Giving Back: Luck, team-building, and sharing success are recurring themes, as English discusses luck’s role in tech, the joy of recruiting, and his philanthropic drive.

This episode offers a thoughtful, candid look into the mind of an entrepreneurial maker—not simply a manager— driven by curiosity, collaboration, and a passion for making better experiences.