Jun 8, 2018 · 37m · 20vc
20VC: From Sequoia To Accel To General Catalyst: What Makes The Best Board Member & The Hiring Methodology To Attract World Class Talent with KAYAK & Lola Founder, 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 The 20 Minute VC, serial entrepreneur Paul English shares actionable insights on startup innovation, recruitment strategies, venture capital, board management, and team leadership. Drawing from his experiences founding Kayak and Lola, English discusses building high-performing cultures, managing investor relationships, and leveraging personal transparency for executive success.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Harry holds 25.9% of the talking time here. How this is scored →
Harry as informed peer 1.4 Guest teaching 3.1 Guest disagreement 0.1 Harry pushing back 0.1
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 18:27 Direct Board Rejection
In a generally mild episode, Paul describes his direct approach when rejecting board member advice, telling them bluntly that their suggestion 'doesn't sound right'.
Hardest push from Harry ▶ 22:00 Down Round Risk ChallengeHarry challenges the wisdom of maximizing valuation during early growth, pointing out the genuine risk of a damaging down round in subsequent funding.
Biggest teaching moment ▶ 28:40 Masterclass in Email ManagementPaul breaks down his strict single-touch processing rule for handling 400 daily emails, educating the host on workflow efficiency.
Harry holds his own ▶ 23:48 Calling Out PR OverhypeHarry demonstrates insider insight into founder behavior by pointing out how startup founders place far too much weight on TechCrunch articles over actual customer growth.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Career Beginnings, Software Development, and Musical Parallel | 1 | 2 | 0 | 0 | Harry asks open-ended introductory questions about Paul's career transition from music to technology. Paul explains the cognitive similarities between arranging music for a jazz band and software architecture, educating the host on how both require orchestrating complex subsystems. | |
| Childhood Influences on Leadership, Dynamics, and Entrepreneurship | 1 | 3 | 0 | 0 | Harry references background research on Paul's upbringing in a large family. Paul outlines his philosophy on problem empathy and validating business ideas through early feedback before writing code. | |
| Foundational Strategies for Exceptional Recruitment and Interviewing | 1 | 3 | 0 | 0 | Harry prompts Paul on his renowned hiring philosophy. Paul describes his proactive recruitment tactics, treating interviewees as collaborators, and training interpersonal connection skills. | |
| Addressing Hiring Pitfalls and Embracing Arrogant Humility | 2 | 3 | 0 | 0 | Harry probes into common founder pitfalls in recruitment and managing ego. Paul shares his concept of 'arrogant humility', balancing personal confidence with curiosity to hire people stronger than oneself. | |
| Top-Tier Venture Capitalists and Managing Board Dynamics | 2 | 4 | 1 | 1 | Harry asks about board management and working with top VCs. Paul provides a masterclass on managing board dynamics, describing how he handles repetitive board members by writing their ideas on a whiteboard to move on. | |
| Fundraising Strategy, Strategic Acquisition, and PR Realities | 2 | 3 | 0 | 0 | Harry and Paul discuss fundraising valuations and M&A strategies, including Kayak's acquisition of Sidestep. Harry offers an astute observation on founders overvaluing PR metrics like TechCrunch coverage, which Paul enthusiastically endorses. | |
| Executive Role Transitions, Time Management, and Email Efficiency | 1 | 4 | 0 | 0 | Paul shares granular productivity frameworks for managing tight schedules and high email volumes. He details his color-coded Google Calendar discipline and his '4 D's' email method (Delete, Do, Delegate, Defer). | |
| Quick-Fire Questions, Bipolar Transparency, and Future Vision | 1 | 3 | 0 | 0 | Harry conducts a quick-fire round covering books, quotes, and personal milestones. Paul delivers a deeply transparent reflection on being diagnosed as bipolar and learning to lead authentically. |
Statements from this episode (12)
Paul English: Music arrangement requires coordination similar to software programming
“The coordination part of music arrangement, to me, feels similar to a lot of the coordination parts of programming, so I felt very comfortable in both areas.”
Tech startup creativity requires problem empathy and relentless iteration
“In tech entrepreneurship, I think most creativity comes out of people who are empaths for problems, and when you see something that irritates you, rather than just say that's irritating and move on, you kind of focus on it, and you try to think about other peo…”
Paul English validates startup ideas by pitching collaborators before writing code
“What I like to do to validate the idea is I write up a SPAC or a design, and then I pitch it, and I might be pitching it to a family member, a friend, a colleague, and it's only when I get one person excited do I say, okay, maybe there's something here, and th…”
Paul English argues interpersonal charisma and recruiting skills are fully trainable
“And a lot of these skills you can do in personal life transfer directly into business life. So I think it's absolutely trainable.”
Arrogant founders fail by hiring subservient employees who avoid challenging them
“Well, I think either the tech founder lacks humility, and they're arrogant, and they only hire people that would be subservient to them, so they don't hire people that are daring enough, and they're going to challenge them and push them.”
Paul English omits distracting board member suggestions from official meeting minutes
“I don't write down everything the board says, and maybe this is bad. I write down the things that are the most significant or things that I'm going to take action on. But if it's something someone mentioned about some side project that I think is Defocused, ev…”
Kayak raised $200M at an $800M valuation with only 39 employees
“So we had to raise like two hundred million dollars. I remember we had 39 employees. They had 130 employees. But we were able to raise an eight hundred million dollar valuation, which was crazy given that we're only 39 employees.”
Paul English argues customers do not care about venture funding announcements
“Your customers don't care who invested in you. And for the most part, your customers don't even care if you're a private company or a public company. I think these milestones are more internal ones. They're not ones important to the customers. So I would encou…”
Paul English rejects email deferral features because they force redundant reviews
“So I really don't like email applications that allow you to defer an email to look at later because that means you've looked at it twice.”
Philanthropists should fund non-profit leaders upfront without imposing bureaucratic reporting hurdles
“Find the leader that inspires you. Write them checks first, and ask the question second. And I know from being in the boards and helping start some non-profits, a lot of donors make the non-profit leader, like, jump through hoops, do so much work in reporting.…”
Kayak co-founder Paul English discusses his experience with bipolar disorder
“So I'm bipolar, and one time early in my career, I was a young VP running a big team.”
Paul English advocates for radical transparency with co-founders during startup crises
“I believe in radical transparency. So if something goes really bad at my company, I'll reach out to my co-founder first and maybe to my management team out of my board and just say, I just really screwed something up, you know, help me think this through. So w…”