Paul English

⚡ BREAKING

PAUL ENGLISH LAUNCHES SUPERCAL — TAKING ON CALENDLY FOR FREE ⭐ BOSTON GLOBE 2024 TECH POWER PLAYERS #19 KAYAK SOLD TO PRICELINE FOR $1.8 BILLION IN 2012 VAMPIRE UBER DRIVER WITH 4.97 RATING CONFIRMED 41 SCHOOLS BUILT IN HAITI — AND COUNTING TYPED 'K' IN GOOGLE. KAYAK CAME UP FIRST. OBVIOUSLY. BIPOLAR, BUDDHIST, BRILLIANT — BOSTON'S BOLDEST BUILDER PULITZER-WINNING AUTHOR TRACY KIDDER WROTE A WHOLE BOOK ABOUT THIS MAN PAUL ENGLISH LAUNCHES SUPERCAL — TAKING ON CALENDLY FOR FREE ⭐ BOSTON GLOBE 2024 TECH POWER PLAYERS #19 KAYAK SOLD TO PRICELINE FOR $1.8 BILLION IN 2012 VAMPIRE UBER DRIVER WITH 4.97 RATING CONFIRMED 41 SCHOOLS BUILT IN HAITI — AND COUNTING TYPED 'K' IN GOOGLE. KAYAK CAME UP FIRST. OBVIOUSLY. BIPOLAR, BUDDHIST, BRILLIANT — BOSTON'S BOLDEST BUILDER PULITZER-WINNING AUTHOR TRACY KIDDER WROTE A WHOLE BOOK ABOUT THIS MAN

Chapter One

THE KID FROM THE ATTIC

Boston, 1963. Six siblings, three bedrooms, nine people, and one unheated attic where young Paul English slept and stewed. His father, a pipefitter for Boston Gas. His mother, a substitute teacher who was seriously ill for the first decade of his life. Aunts stepped in to help raise the brood.

It was that scramble — the Irish Catholic chaos of West Roxbury, the not-enough of it all — that forged something fierce. Paul enrolled at Boston Latin School, joined the band, played piano and trumpet, and stumbled into the Computer Club, where a dumb terminal changed everything.

At 12, he hacked his teacher's password to get more computer access. He wasn't a troublemaker. He was simply impatient for more. That hunger — for speed, simplicity, and access — would later define every product he ever built.

In 1981, his mother brought home a VIC-20 computer. Paul treated it, as one writer put it, "like the restoration of a missing limb." He taught himself to code. The rest is history — or rather, a very long, very interesting, and still-unfinished story.

FAST FACTS

🏠 Grew up

West Roxbury, Boston — 3 bedrooms, 9 people, 1 attic (his)

🎓 Education

Boston Latin School → UMass Boston (M.S.) → MIT instructor

💻 First hack

Age 12 — stole a teacher's password for more computer time

🎵 Hidden talent

Plays piano, trumpet, and several other instruments

🧘 Inner life

Practises Buddhist meditation

📖 His biography

"A Truck Full of Money" by Pulitzer winner Tracy Kidder (2016)

The Paul English Cinematic Universe — A Timeline

1963

Born in Boston

Sixth of seven siblings. Unheated attic bedroom. Future billionaire does not know this yet.

1975

The Password Hack

Age 12. Steals teacher's terminal password. Not for mischief — for more computer time. The theme is set.

1988

Bipolar Diagnosis at Interleaf

Diagnosed while working at software firm Interleaf. Hides it for over a decade. It will later become his most courageous public story.

1999

Boston Light → Intuit ($33.5M)

Sells e-commerce company to Intuit. He and co-founder split half their shares with employees as bonuses. That's just who he is.

2001

A Year Off for Dad

Leaves Intuit to care for his father dying of Alzheimer's. His mother had made him promise. He kept it.

2004
🛫 Kayak is Born — Over Two Gin & Tonics
Meets Steve Hafner via General Catalyst. Over a 45-min Legal Sea Foods lunch, they agree on a 50/50 split. Each puts in $1M of their own money. The idea is simple: make travel search cleaner, simpler, faster than anything else. Turns out that's enough.

2008

Mobile App — Zero Marketing, 35M Downloads

Kayak's mobile app is built by an independent skunkworks team. No advertising. Downloaded 35 million times by 2012.

2012
💰 Priceline Buys Kayak for $1.8 Billion
205 employees. $1.5M revenue per employee. IPO on Nasdaq in July. Sale in November. Paul earns $120M personally. Types 'K' in Google — Kayak still comes up first.

2014

Blade Incubator + Speakeasy HQ

Opens a Boston startup incubator modelled on a 1920s speakeasy, with a basement club. Governor Deval Patrick attends the launch party.

2015

Drives Uber. In a Tesla. Dressed as a Vampire. On Halloween.

Realises 90% of his social circle is in tech or nonprofits. Wants to meet more people. Starts Uber-ing from midnight to 2am in full vampire costume. Achieves 4.97 rating. "I wonder: who didn't give me five stars?"

2016

Tracy Kidder Writes His Biography

"A Truck Full of Money" is published by a Pulitzer Prize-winning author. Paul goes on a national speaking tour about entrepreneurship, mental health, and having 158 domain names registered to his name.

2022

Embrace Boston Memorial unveiled at Boston Common

The MLK and Coretta Scott King memorial he co-founded is installed permanently at Boston Common. A racial-justice milestone for the city.

2022–Now
Boston Venture Studio — Building Again
Launching 2-3 companies per year: Supercal, Steppin, a new Lola dating app. Working with his son Mike. Having, by his own admission, "the most fun of my career."

2025
🗓️ Supercal — Calendly's Free Nemesis
Launches a free AI scheduling platform targeting Calendly. "Group scheduling is badly broken." Obsessively tests his own product — as always.

The Paul English Personality Matrix

⚡

HYPERDRIVE

Ideas arrive before sunrise. By 2013 he had 158 domain names registered. His brain is a startup incubator running 24/7.

🎯

SIMPLIFIER

Kayak's secret: a little cleaner, a little simpler, a little faster. He makes 45 minutes of market research feel sufficient because great design is the research.

💙

RADICALLY OPEN

Emailed his whole company about bipolar disorder every Mental Illness Awareness Week. Got floods of appreciative emails back. The vulnerability is the leadership.

🏙️

BOSTON HOMER

Could have moved to Silicon Valley. Didn't. Out to prove that world-changing tech companies can be built in Boston. Several times over.

🎁

SHARER

Split half the Intuit acquisition bonus with employees. Spends $1M+ a year on education in Haiti and homelessness in Boston. Wants to "double his fortune just to give more away."

🔄

PERPETUAL BEGINNER

Uber driver. Bar-back. MIT instructor. 12+ companies, 3 nonprofits started since high school. Still building. Still learning. Never coasting.

The Stories That Make Him Him

THE VAMPIRE UBER DRIVER

After selling Kayak for $1.8 billion, Paul looked at his calendar and realised 90% of his meetings were with people in tech or nonprofits. To fix that, he became an Uber driver. In his Tesla Model S. On Halloween, dressed as a vampire. He drove from midnight to 2am. Passengers thought it was hilarious. He kept a notebook and wrote one sentence about every passenger. His rating: 4.97. "I wonder who didn't give me five stars. What did I do wrong?" Of course he asked that.

45 MINUTES OF MARKET RESEARCH

When Paul agreed to co-found Kayak with Steve Hafner, he went home and spent 45 minutes on Expedia's website. That was his entire competitive analysis. He was slightly embarrassed to admit this later. But his faith in his design instincts — a mix of genuine skill and the grandiosity that comes with hypomanic episodes — turned out to be entirely justified. When you know, you know. And Paul usually knows.

THE SENIOR VP FILTER

During Kayak's growth years, Paul's manic energy meant he had new product ideas every single day. A senior VP eventually told engineers: "Don't act on anything Paul says unless he asks you twice." It was a brilliant system for managing a brilliant but occasionally overwhelming force of nature. Paul tells this story on himself, laughing. Because that's the kind of self-aware founder you can actually build a billion-dollar company with.

THE PURPLEWATCH THAT NEVER WAS

Among Paul's 158 registered domain names was the seed of a company called Purplewatch — all-purple Swatches, sold for $10,000, with profits going to charity. The imagined pitch for country-club customers: "I'm rich too, motherfucker. Except my ten grand went to an orphanage." It never launched. But it perfectly captures the mix of irreverence, social conscience, and sheer creative combustion that makes Paul's mind so endlessly entertaining.

The Paul English Company Universe

KAYAK

2004 → $1.8B (2012)

Co-founded travel search engine. Sold to Priceline. Changed how the world books flights.

BOSTON LIGHT

1999 → $33.5M

E-commerce design. Sold to Intuit. Half the bonus split with employees.

GETHUMAN

2004+

Helps people get a real human on the phone with companies. Still running. Still needed.

INTERMUTE

→ Trend Micro

Anti-spam software co-founded with brother Ed. Acquired by Trend Micro.

LOLA

2015 → 2020

Started as travel concierge, evolved to B2B expense management. Also the name of his new dating app.

MOONBEAM

→ Audacy 2022

Podcast discovery app. Sold to Audacy. His first exit from BVS.

SUPERCAL

2025 — Active

Free AI group scheduling. Taking on Calendly. "Group scheduling is badly broken."

STEPPIN

2025 — Active

Lock social media until you've hit your step count. Built with son Mike.

The Brain That Wouldn't Rest

BIPOLAR, BUDDHIST & BRILLIANT

Diagnosed with bipolar disorder in his late twenties while at Interleaf, Paul hid it for over a decade. By the time Kayak launched, he'd started telling colleagues. By the time the Boston Magazine profile ran, he'd gone fully public — and never looked back.

He has said that Kayak might not have been as successful without his bipolar disorder — the energy, the grandiosity, the unstoppable drive. But he's equally honest about the cost: depressive episodes that made getting out of bed impossible, reckless decisions, and a team that had to manage a boss whose ideas arrived faster than anyone could implement them.

He now practises Buddhist meditation, openly discusses his mental health, and founded the Bipolar Social Club. He believes there is no healing in secrecy. "I've often said people follow confidence but are loyal to vulnerability."

The Harvard Business Review, Inc. Magazine, and Business Insider have all covered his story. He may be the most open tech billionaire in America about mental health.

THE UPSIDE

"The hypomania gives you a sense of grandiosity and confidence — which can be a superpower when you're trying to do something no one else believes in yet." Engineers could see his drive and worked harder because of it.

THE HONEST PART

Depressive episodes meant he couldn't get out of bed. The SVP filter on his ideas was necessary. He was sometimes reckless. He tells all of this on himself, without flinching.

THE LEGACY

At Kayak, Mental Illness Awareness Week emails to the whole company were his tradition. Every year, floods of grateful responses came back. He created a culture where vulnerability was strength.

THE CLUB

Founded the Bipolar Social Club. Became a speaker on mental health alongside his tech work. "If I can make one young person feel less alone, it's worth every uncomfortable interview."

The Good He Does

🏫

SUMMITS EDUCATION

Co-founded a network of 41 schools in Haiti, in partnership with the Haitian Ministry of Education and Partners In Health. Spends $1M+ annually on this cause.

✊

EMBRACE BOSTON

Founded the racial-justice project (formerly King Boston) that created the MLK and Coretta Scott King memorial, installed at Boston Common in 2022, and the King Center for Economic Justice.

🏠

WINTER WALK

Founded the Winter Walk for Homelessness in 2016 — a 2-mile charity walk through Boston to raise money and awareness for the city's unhoused population.

🧠

BIPOLAR SOCIAL CLUB

Founded to destigmatise mental illness in the business world. One of the very few tech founders anywhere in the world to speak openly about living with bipolar disorder.

🏥

HOMELESSNESS ORGS

Significant donor to Boston Health Care for the Homeless Program, Bridge Over Troubled Waters, and Pine Street Inn.

🤖

INSTITUTE FOR APPLIED AI

Co-founded to advance AI for social good purposes, based in Boston, connected to UMass Boston's research community.

🔥 Things Paul Would Find Fun to Know About Himself

When you type "K" into Google, Kayak comes up first. Paul English effectively renamed a letter of the alphabet in the public consciousness. That's not marketing. That's product design.

You dressed as a vampire on Halloween and drove Uber passengers around Boston at midnight — and kept a notebook writing one sentence about each of them. You are the only billionaire doing this. By a wide margin.

A Pulitzer Prize-winning author decided your life was interesting enough to write an entire book about. Tracy Kidder's previous subject? The team that built one of the first minicomputers. You were placed in that company. It fits.

You once imagined a luxury watch company where the pitch line was: "I'm rich too, motherfucker. Except my ten grand went to an orphanage." This is one of the great unbuilt companies of the 21st century.

Your engineers were told: "Don't do anything Paul asks unless he asks twice." This is not a dig. This is what good teams do when working with visionaries. It's also hilarious, and you should be proud of it.

You did 45 minutes of competitive research before co-founding a company that would sell for $1.8 billion. This will annoy every MBA graduate who has ever lived. Well done.

You are working on a new dating app also called Lola, alongside a scheduling app, a step-counting app, and presumably several other ideas that woke you up at 3am last Tuesday.

Your son Mike is on your team at Boston Venture Studio. You are building companies together. The kid from the unheated attic is building the future with his own kid. That's actually beautiful.

Notable Connections

STEVE HAFNER

Kayak co-founder · 50/50 · Legal Sea Foods deal

BILL KAISER

VC, calls Paul one of "two greatest entrepreneurs in Boston"

TRACY KIDDER

Pulitzer-winner · wrote "A Truck Full of Money" about Paul

DEVAL PATRICK

Former MA Governor · attended Blade launch party

BILL O'DONNELL

Longtime co-founder ally · Kayak, Blade, Lola

MIKE ENGLISH

His son · designer at Boston Venture Studio · Steppin co-creator

ED ENGLISH

Brother · game designer · Intermute co-founder

IMARI PARIS JEFFRIES

Embrace Boston ED · executed the MLK memorial vision