Prompt Cast
Paul English's Journey from Programming Prodigy to Co-Founder of Kayak
TLDR Paul English's path from coding on a Commodore VIC-20 to founding Kayak involved struggles with mental health, successful ventures like Boston Light Software, and a dedication to creating user-friendly tech solutions that led to the company's rapid growth and eventual acquisition.
Timestamped Summary
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06:30
Paul English grew up in a crowded house with seven siblings sharing one bathroom, and his parents had very different personalities.
12:24
Paul English excelled in school with diverse interests and competitive spirit, learning to code on a Commodore VIC-20 computer at home, eventually creating a video game company in his teens and pursuing a career in computers through various jobs during and after college.
18:00
Paul English worked long hours and became obsessed with programming, eventually transitioning into management roles in tech companies while experiencing episodes of depression and anxiety in his late 20s.
23:37
Paul English experienced manic episodes that allowed him to be creative but also led to detachment from others, eventually leading to a bipolar diagnosis and a long journey to find the right medication to manage his condition.
29:39
Paul English founded Boston Light Software in 1998, which focused on helping small businesses with online services and payments before being acquired by Intuit for $33.5 million.
35:52
Paul English met Steve Hafner, a co-founder of Orbitz, who shared his frustration with the travel industry and pitched the idea of creating a comprehensive travel search engine, leading to the birth of a new company.
41:50
Paul English met Steve Hafner, who initially offered him a CTO position, but after some negotiation, they became 50-50 partners in their new venture, Kayak, which they started by raising funds and recruiting a team.
47:16
Paul English and Steve Hafner founded Kayak with the goal of creating a simpler and cleaner travel website than the market leader, Expedia, ultimately choosing the name Kayak after considering various other options.
53:09
Kayak started with a small team of smart individuals and grew rapidly through word of mouth, eventually becoming self-sustaining through direct traffic and innovative partnerships with airlines and online travel agencies.
58:51
Kayak became highly profitable and fast-growing by maintaining a lean team, reaching significant milestones in self-directed traffic, and focusing on user experience rather than complex technology.
01:04:19
Kayak went public, was acquired by Priceline, and Paul English felt overwhelmed by the fame and requests for money that followed.
01:10:07
Paul English still owns Get Human, a profitable company focused on customer support, while also running Lola, a spend management software business, and engaging in various nonprofit and startup ventures.
01:16:04
Paul English wanted Lola's customer service to be exceptional, so he drove for Uber to experience real-time feedback before implementing a rating system for Lola's service people.
Categories:
Business
