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

In this episode of "20 minutes VC," host Harry Stebbings interviews Paul English, co-founder of Kayak and Lola. Paul shares insights from his journey as a programmer with a passion for music to a successful entrepreneur, emphasizing the importance of creativity, empathy, and problem-solving in tech startups. He discusses his approach to hiring, aiming to work with inspiring and smarter individuals, and the significance of building a strong culture within a team. Paul also touches on his experiences with fundraising, IPOs, and the value of smart money over higher valuations. Additionally, he highlights his method of managing a high volume of emails and the importance of balancing personal and professional life. As a philanthropist, Paul advises finding inspiring leaders to support and shares his personal challenge of being bipolar, advocating for transparency and shared problem-solving. Looking ahead, Paul's goal for Lola is to create an electrifying work environment that fosters growth and passion among its team members.

• Harry Stebbings introduces Paul English, co-founder of Kayak and Lola.
• Lola focuses on improving business travel experiences.
• Paul English's companies have raised significant funding from notable VC firms.
• Paul is also recognized for his philanthropic work and has been featured in media, including a book by Tracy Kidder.
• Harry thanks Fred Destin for introducing him to Paul English.

"So I'm very excited to welcome Paul English, co-founder of both Kayak and Lola."

This quote introduces Paul English as a significant figure in the tech and startup industry, highlighting his successful ventures and philanthropic efforts.

• Paul English is a programmer with interests in music and computers.
• He compares the processes of arranging music and writing code.
• English's upbringing in a large Irish family influenced his sensitivity to team dynamics and culture.
• His father's entrepreneurial activities at garage sales inspired Paul's understanding of entrepreneurship.

"I look at it, arranging music and writing code are very similar to me, and I did both in college, and then I ended up working full time as an engineer, going to school kind of at night and then just taking it from there."

Paul English draws parallels between music arrangement and programming, indicating a creative and structured approach to his work in technology.

"I think to be a successful entrepreneur, and this has been said many times by a lot of people, but I believe that the most important thing you can do is build the culture and the team and the interactions."

Paul English emphasizes the importance of team culture and dynamics in entrepreneurship, linking it to his early life experiences.

• Paul believes creativity responds to problems and requires empathy.
• He stresses the importance of focusing on a problem to iterate and find solutions.
• English reflects on how his approach to idea generation and creativity has evolved from programming to broader entrepreneurial contexts.

"I think most creativity comes out of people who are empaths for problems."

This quote highlights Paul English's view that creativity in business is driven by a deep understanding of and empathy for problems.

"It's the radar lock on the problem that allows you to keep iterating and trying and trying and trying different things so eventually you find something that works."

Paul English explains that persistent focus on a problem is key to developing effective solutions through continuous iteration.

• Paul shares his method of validating ideas by writing specs and pitching them to others.
• He seeks to inspire excitement in others before pursuing an idea further.
• English's validation process involves gauging interest and willingness to collaborate on an idea.

"It's only when I get one person excited do I say, okay, maybe there's something here, and then I pitch it to more and more people."

Paul English describes his process of idea validation, which relies on sparking interest in at least one other person as an initial litmus test.

• Paul English is always focused on hiring and considers it a critical aspect of his work.
• He actively engages in hiring-related activities, even during personal time, like Uber rides.

"I'm going back and forth on my phone, and"

Although the quote is incomplete, it suggests Paul English's dedication to the hiring process, indicating that he is constantly involved in recruiting talent for his ventures.

• Harry Stebbings discusses a TaskRabbit interaction with a woman he was impressed by, considering hiring her again.
• He emphasizes the importance of recognizing and matching talent, even outside his own company, Lola.
• Networking and introductions are a part of his approach to talent management.

"And there's a woman who did a task, like a year ago, and I vaguely remember I never met her in person, but being really, really impressed with her organizational and writing and all that."

This quote highlights Harry Stebbings' ability to remember and appreciate talent, even from brief or indirect interactions, and his consideration of future opportunities for collaboration.

• Paul English believes storytelling and humility are key to hiring effectively.
• Creating a personal connection with potential hires is crucial.
• He aims to make candidates feel valued during the interview process.

"I think it's a couple of things. I mean, one is you need to be a storyteller and get people excited in a vision."

This quote encapsulates Paul English's perspective that a compelling vision and the ability to communicate it are fundamental to attracting top talent.

• Paul English comments on the natural charisma of individuals like Bill Clinton.
• He asserts that connection skills can be trained, referencing techniques to help autistic children.
• Personal and business connection skills are transferable and teachable.

"But it's also trainable, for sure."

Paul English stresses that while some people may have an innate charisma, the ability to connect with others is a skill that can be developed and honed over time.

• Paul English observes that some tech founders fail to hire challenging and daring individuals.
• He advocates for hiring people who are smarter and can push the founder to improve.
• The focus should be on collaborative relationships rather than hierarchical ones.

"So they don't hire people that are daring enough and they're going to challenge them and push them."

This quote reflects Paul English's belief that a common mistake among tech founders is not hiring individuals who can provide constructive challenges and drive innovation.

• Paul English introduces the concept of "arrogant humility."
• Successful individuals should have confidence but also a desire to learn from others.
• The balance between confidence and curiosity is key to building a strong team.

"What I mean by that is you want people that have been successful for sure, and they don't have to have done what you need them to do right now."

Paul English explains that past success is indicative of transferable skills and that confidence combined with humility can be a powerful attribute in team members.

• Paul English discusses his experience with VCs like Mike at Sequoia and Joel at GC.
• He values their ability to synthesize and articulate a simple vision.
• Exceptional VCs are also good at coaching, encouraging, and pushing entrepreneurs.

"I look at them both as incredibly bright."

This quote highlights Paul English's admiration for VCs who possess intellectual acuity and the capability to guide entrepreneurs effectively.

• Paul English talks about the importance of a high-functioning board where members get along.
• He shares a strategy for managing repetitive suggestions during board meetings.
• Clarity on the board's role and effective meeting management are essential.

"So I've had to coach board members about how I want them to operate in my board meeting."

Paul English shares his approach to directing board members to ensure productive and efficient board meetings.

• Paul English discusses how to gracefully reject board suggestions that don't align with the founder's vision.
• Honest and direct communication, with a focus on the company's top priorities, is his approach.

"I'll say, I think that's a really great idea, but I don't think we can think about that until we get x, Y and Z done."

This quote illustrates Paul English's method of diplomatically addressing board suggestions by prioritizing the company's immediate goals.

• Harry Stebbings discusses the importance of prioritizing tasks and not overloading board meeting agendas with too many action items.
• Focus should be on the two or three most important things to execute between board meetings.
• Harry writes minutes by hand during the board meeting and transcribes them to a Google Document to email out the same day.
• He only includes significant matters or things he will take action on in the minutes, leaving out what he considers defocused or low priority.

"We can't leave a board meeting with 50 action items to really effective. You have to think about what are the two or three really most important things and then make sure you crush those between board meetings."

This quote emphasizes the necessity of focusing on a few critical tasks rather than an overwhelming number of actions post-board meetings, which leads to increased effectiveness and productivity.

• Paul English believes in acquiring "smart money" from investors rather than just seeking the highest valuation.
• The early years of a startup should focus on the individuals who will be part of the journey for an extended period.
• Paul mentions his experience with Kayak and the influence of Joel Cutler, a founding investor, on the company's success.
• It's important to partner with ethical, kind, and brilliant individuals who the team will be excited to work with for many years.

"I am a believer that you want to get smart money, and I'd rather take smart money at a lower valuation than dumb money at a higher valuation."

Paul English's quote reflects his investment philosophy where the quality and compatibility of investors take precedence over merely obtaining a higher valuation for the company.

• Paul English discusses a strategic fundraising round at Kayak to acquire their biggest competitor, Sidestep.
• The focus was on raising funds at a high valuation to minimize dilution and afford the acquisition.
• The acquisition was successful, significantly increasing Kayak's traffic and commercialization rates.

"We were able to raise at an 800 million dollar valuation, which was crazy given that we're only 39 employees, but we raised on our growth rate was looking really good."

The quote illustrates a specific instance where maximizing valuation was crucial for Kayak to achieve a strategic acquisition without excessive dilution of equity.

• Paul English agrees with Harry Stebbings that founders often overvalue the importance of PR from funding rounds or going public.
• Customers are generally indifferent to a company's investment sources or whether it's private or public.
• Founders should focus on building an excellent team and products rather than on fundraising or public perception.

"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."

Paul English's quote suggests that customer-centricity should be the primary focus for founders, rather than the prestige or public relations benefits that might come with investment milestones.

• Paul English found the Kayak IPO to be a fun and defining event, but it did not change the company's day-to-day focus on customer service and product improvement.
• Being the CTO allowed him to concentrate on product and customer support without the added responsibilities of finance that come with being a public company.

"It was great. But it didn't change things one day to the next day for our customers."

The quote conveys that while an IPO can be a significant financial event for a company and its employees, it does not necessarily impact the fundamental business operations or customer experience.

• Paul English has transitioned between the roles of CTO and CEO multiple times across different companies.
• His core skill and preferred role is that of a product manager, focusing on product design and evolution.
• As CEO, he delegates tasks he's not great at to others who excel in those areas.

"I think at the core, I mean, I'm an engineer by training my best skill. If I had to put me functionally on an.org chart, I would say would be product manager."

This quote reflects Paul English's self-awareness of his strengths and the recognition of the importance of delegation in leadership roles.

• Paul English uses color-coded Google Calendar for time management and maintains a balance between work, nonprofit activities, and self-investment.
• He ensures that his schedule includes a healthy mix of initiatives he is passionate about and responses to others' requests.
• Paul regularly reviews and adjusts his calendar to maintain this balance and avoid being overwhelmed by his commitments.

"I am pretty disciplined about my time."

Paul English's quote highlights his structured approach to managing a busy schedule, ensuring he dedicates time to various aspects of his life while keeping his priorities in check.

• Balancing personal projects with helping others is crucial for a fulfilling work life.
• A lack of balance can lead to stressful and miserable days.

"And then also balancing that with time that you're helping other people with their projects. And I think unless you have a good balance between those two things, you end up having really stressful, miserable days."

This quote emphasizes the importance of finding equilibrium between focusing on personal tasks and assisting others, which is essential to avoid stress and unhappiness.

• Paul receives around 400 non-spam emails a day.
• He uses three main inboxes for different purposes: work, personal, and e-commerce.
• Paul believes in handling emails in one touch and not deferring them.
• He applies the "four Ds" to manage emails: Delete, Do, Delegate, and Defer.
• Delegation should be trusted without micromanagement.
• Aiming to keep the inbox at ten items or fewer helps maintain control over email.

"So the first one is I delete it... The second thing is you have to do something about it... The third thing I do is delegate... And then the fourth one is defer..."

Paul outlines his systematic approach to email management, which involves making immediate decisions to delete, do, delegate, or defer emails to maintain efficiency and control over his inbox.

• Paul recommends "The Trumpet of Conscience" by Martin Luther King Jr., finding it inspirational and visionary.

"There's a collection of essays I've read with him recently called the Trumpet of Conscience. It's just remarkable in sort of the breadth and depth of his work and what a visionary he was and what a citizen of the world."

Paul suggests this book due to its profound impact on him, highlighting the significant influence of Martin Luther King Jr.'s work on his thinking.

• Personal feedback from former employees, such as being told it was their best job, is a highlight for Paul.

"I think it's, last night I met for drinks with someone who worked for me twelve years ago, and I met her and her colleagues that she works with now, and she told them that, she said, working for Paul was the best job I've ever had..."

This quote reflects Paul's pride in creating a positive work environment that leaves a lasting impression on his team members.

• Paul believes in supporting nonprofit leaders without burdening them with excessive requirements.
• He advises to trust and fund leaders who inspire you, letting them use their expertise without micromanagement.

"Find a leader that inspires you. Write them checks first and ask the question second."

Paul's philosophy on philanthropy focuses on identifying and financially backing inspiring leaders, allowing them to operate effectively in their areas of expertise.

• Martin Luther King Jr.'s quote about doing what's right resonates with Paul.

"One of his quotes that I've always really liked is, it's always the right time to do what's right."

This quote is a personal motto for Paul, reflecting his commitment to integrity and ethical action in all situations.

• Being diagnosed as bipolar and learning to balance his condition without losing his energy was an inflection point for Paul.

"I'm bipolar... I remember one of my guys who worked with me said, you seem really depressed... you don't have the energy you used to have."

Paul shares a personal moment that led him to embrace his natural tendencies while managing his bipolar condition, highlighting the importance of authenticity and self-acceptance.

• Paul believes in radical transparency and sharing problems for collective problem-solving.
• He values shared pain and the support of a good team during difficult times.

"The first thing is I do is I share information about it. So I believe in radical transparency... I'm a big believer in shared pain."

This quote underlines Paul's approach to crisis management, which involves open communication and relying on a supportive team to navigate challenges.

• Paul's goal is to create an exciting and fulfilling work environment at Lola.
• He wants to foster team growth, skill development, and a passionate work culture.
• Creating an electrifying team environment is a priority for him.

"I want to create the place that's the most exciting place of people's career... Creating this electrifying environment where people are very brilliant but passionate, they love working together."

Paul's vision for the next five years includes building a vibrant and dynamic team culture that enhances career satisfaction and development for his employees.

• Paul is appreciated for his time and insights during the interview.
• Listeners are directed to follow Paul on Twitter and engage with the podcast's social media.

"What an incredible guest to have on the show. And I want to say a huge thank you to Paul for giving up his time today to appear on the show."

The host expresses gratitude to Paul for his contribution to the podcast and encourages the audience to connect with him and the show online.