Startup Insights From the Co-Founder of Kayak

Key points (worth reading the expanded version, though):

1. “I've started four or five companies now, based on how you count. There is one I am trying to forget.” Most serial entrepreneurs that I know don’t have a 100% “hit rate”. Just about everyone has had at least one venture that didn’t quite turn out the way they had hoped. I like that Paul’s able

2. Like me, Paul also started a company with his brother. I have to remember to chat with him about that over a beer someday. [Note to self: Write article titled “Starting Something With A Sibling: Understanding The Tradeoffs”.

3. Like many of my favorite software entrepreneurs, Paul’s a programmer by training. Interesting side note: In my recent travels and interactions with entrepreneurs, I’m finding that an increasing number of founders have a design/UI/UX background.

4. When asked “Why do you start companies”, Paul has one of the best answers I’ve ever heard: I start companies because it gives me an opportunity to create teams.

5. “Our priorities are always team first, customer second and profit third.”

6. The difference between an A team and an A+ team is the difference between a million in revenue and a billion in revenue.

7. Sometimes people Paul is interviewing say “I’ve heard a lot of great things about you.”. Paul: “Trust me, after a few months, you’ll learn that the reason you’re here is not me, but the people around you”

8. Paul English on recruiting (I’m paraphrasing this from a meeting I had with him and some pieces from this interview): When someone mentions the name of a person that they’ve worked with that they think is exceptional, a little clock starts ticking in my head. My world goes to black and white, and this clock is in color. From when the clock starts, I give myself seven days to track them down, back channel, get them in for two series of interviews that are intense and focused, and make an offer and have them accept it. That's seven days from when I hear the person's name.

9. At least one of the co-founders needs to be passionate about recruiting because that absolutely makes all the difference in the world.

10. When Paul started Kayak, one thing that was very important to him was building something that his friends could use. Before Kaya, when people asked "What do you do?", his response was "I work in an operations research group at data general, and we're studying advanced processes for doing disc drive manufacturing." Clearly, unlikely to be fascinating to most people. With Kayak he wanted it to be different. I have had almost precisely this experience. For my current startup, I wanted to work on something that when random strangers asked me what I did, I wanted a decent chance that the answer would be relevant to them.

11. “I had sold two companies. I didn't want to sell a company again. So my venture guys would sometimes say, "You know, explore it." And I'd have the meeting knowing in my mind that there is no way I am going to sell this company.”

12. When Paul was hiring his early team, he refused to hire people from the travel industry. He didn’t want travel people, he wanted consumer product people.

13. One of Paul’s investors said, “You’ll name this company Kayak over my dead body.” Paul: “Thanks for the input.”

14. The Red Phone: Paul found the most obnoxious, loud-ringing red phone he could find and plugged it in right in the engineering office. About 30% of the time, when a Kayak web visitor saw a support phone number on the website, it was the number of that phone. The idea was to build a culture that was centered around the customer.

15. “I guess this is the first time I'm talking about this. But I'm at the beginning of a new project, which will be my next 10 year project. I'll be at Kayak, of course, pushing it, pushing it, but I'm starting a new project that has an audacious goal of creating free low-bandwidth Internet for the whole continent of Africa. [This super-cool.]

16. In an uncharacteristic moment, I actually asked Paul a question in the session about how his advice around recruiting as a company grows from 5 to 50 to 500 people. He had two points: First, make sure you identify the stars. He does this by asking people on his team who the brightest people they’ve worked with is. Then, make sure that they know how much emphasis you put on the team and go after them — aggressively.

17. If you visit Kayak.com and hit the feedback button, you will get a response via email. Kayak responds, individually, to every email. That’s impressive. What is crazy-impressive is that the email response comes from either Paul or someone on the engineering team. He gets flack for using a $150k/engineer to answer support emails when the rest of the world is outsourcing it for $8/hour or something. Why does he do this? Because, when engineers respond to support issues, when the same issues arise time and time again, they are more likely to stop what they are doing and go fix the problem so that they don’t have to answer that same question again. And, because it sends a message to the entire team that they take these issues very seriously.