Paul English

Make money through clear, measurable value creation. Display these metrics visibly to keep your team connected to the actual economic impact of their work.

Kayak displayed a real-time counter of daily travel searches on a prominent screen. This connected programmers directly to their company's revenue driver, showing that every search represented tangible value: 75 cents for flights, $2 for hotels.

Recruit trusted collaborators repeatedly across ventures. Building long-term relationships with people you know and trust creates stability and institutional knowledge across multiple company attempts.

Paul worked with the same core group across multiple startups spanning decades. When Billo, Schwenk, and Rago heard Paul was starting Boston Light after previous failures, Billo immediately recognized the pattern and committed despite past losses, saying he believed this one would work.

“Someday, this boy's going to get hit by a truck full of money, and I'm going to be standing beside him.”

Pleasure is enhanced when you accomplish something with limited tools. Constraints breed satisfaction more effectively than abundance.

Paul discovered that writing software within strict memory limitations for the Atari 2600 and other constrained systems created deeper satisfaction than programming without bounds. The constraint forced elegance and optimization.

“One rather curious thing I've noticed about aesthetic satisfaction is that our pleasure is significantly enhanced when we accomplish something with limited tools.”

Share significant proceeds with your core team. Redistribute wealth among people who built the company with you to align interests and recognize their contribution.

When Paul sold Boston Light Software for $33.5 million, he gave half his own proceeds to his team. Later at Kayak, he ensured his lieutenants Billo and Schwenk owned stock worth nearly $20 million each, making them financially independent partners in success.

Learn software engineering through applied work, not theory alone. Day jobs in programming provide clinical education equivalent to any academic program.

Paul took night classes in computer science at UMass Boston while working full-time as a programmer for seven years. His jobs rewriting administrative software, programming centrifuges, controlling high-speed cameras, and working alongside PhDs at Data General provided practical knowledge that complemented his academic study.

“Paul's day jobs added up to a supplemental course, like clinical rotations in medical school.”

Being a founder requires abandoning the boundary between work and life. Your identity merges with your company in ways that make failure feel personal and success feel incomplete.

Unlike employees who clock out and separate themselves from their job, founders cannot maintain this boundary. Paul found himself obsessed with his companies, unable to disengage even after selling them, and struggling with depression when success arrived because it meant becoming an employee again.

“As of tomorrow morning when I wake up, I'm now an employee.”

Recognize that technological advancement democratizes opportunity in ways previous generations never experienced. A person with the right skills can rise regardless of family background or social class in knowledge-based fields.

Paul's rise in technology allowed him to succeed despite not coming from Boston's Anglo-Saxon elite families. Unlike the construction industry where politics mattered, software required only belonging to what Donald Knuth called the 2 percent of people born to program, making class and connections irrelevant.

Do not conflate personal mental health with professional success or failure. A company setback or personal crisis does not define your worth, and vice versa.

Paul experienced severe depression triggered by Kayak's successful sale and media attention, not by failure. The book emphasizes that successful people struggle with mental illness in ways that are often invisible to outsiders, and success does not prevent psychological suffering.

Seek clarity about your condition and what you can control. Understanding your symptoms is more valuable than abstract diagnostic labels. Focus on concrete steps to manage impact.

Paul rejected the stigma of bipolar disorder as a label and instead focused on identifying specific symptoms he experienced and testing medications that reduced them. He was pragmatic about treatment, discontinuing lithium when it flattened his energy even though it helped with depression.

“The labels are kind of dumb and meaningless because no one really knows how the mind works.”

Code offers a refuge where you maintain complete control. Unlike human relationships, computers respond predictably to your commands and don't argue or ignore you.

Growing up in a chaotic household with seven siblings, Paul found programming to be a solitary world where he was entirely in charge. In his basement room at any hour, he could create universes within code where there was no time but the present and no place but the small system he was building.

“In his basement room it could be of any time of day or night and when he was coding or watching a message being painted on his screen he felt as though there was no other time than now and no other place but the small universe he was creating in his current program.”

Keep meetings small and time-conscious. Interrupt unproductive meetings by visibly signaling that fewer people and less time can solve the same problems.

Paul would pop his head into large, long meetings and suggest that three of the dozen people present could solve the problem in half the time. He hung a tally clicker outside the main conference room as a visible reminder of his expectation for smaller gatherings.

“I'm paying attention. I want meetings of three people, not 10.”

Program yourself out of depression through focused work. When facing setback and despair, channeling energy into building something tangible can restore momentum and identity.

After turning down Yahoo's acquisition offer and experiencing three years of depression, Paul worked part-time as a programmer earning $80 an hour. He gradually built Boston Light Software through a contract with the Boston Globe, and this act of creation restored his sense of purpose and capability.

“He had programmed his way out of depression.”

View mental illness not as a complete liability but as a condition with managed symptoms and untapped capabilities. Even significant psychological challenges do not preclude building successful companies and creating value.

Paul was diagnosed with bipolar disorder and spent 30 years managing episodes of hypomania and depression through medication, trial and error, and occasional abandonment of treatment. Despite struggling with mental illness, he founded multiple companies, one acquired for $1.8 billion, and earned $120 million.

“What's really important is what are the symptoms you're having and are they that bad? And then what things can we do to make those symptoms be less?”

Negotiate aggressively by studying how others do it. Watch successful negotiators operate and apply their tactics in your own high-stakes situations.

Paul learned negotiation by observing his father at yard sales, where his dad would disarm sellers with humor, throw out absurdly low numbers, and let the unexpected offer create the anchor point. Years later, Paul used this same playbook to negotiate Boston Light's sale from $0 revenue to $33.5 million.

Ideas are cheap. Multiple failed attempts across decades can be justified if one or two succeed spectacularly. A 2 percent success rate can fund a lifetime of exploration.

Paul had approximately 50 different ideas throughout his career, with 15-20 actually being started as companies, apps, or divisions. Most failed, but two significant successes (Boston Light and Kayak) more than compensated for all the losses, teaching that portfolio approach to entrepreneurship.

Build for a big market with clear demand. Even ideas that seem unconventional can succeed if they address massive customer pain and you have the technology to execute.

Addison Gage harvested ice from Massachusetts ponds and shipped it worldwide to warm climates before refrigeration existed. The enormous market demand in hot countries justified the logistics. This historical example taught Paul that vision and market size matter more than an idea seeming obvious upfront.

“No matter how wacky an idea can succeed if it aims at a big market, all those hot places without refrigeration, and if there are technologies to execute it.”