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Paul English co-founded Kayak, which he took public and then sold to Priceline for $2 billion in 2013. We pitched Paul on Endorfyn, the PopSleuth app that alerted fans to new content from and about their favorite artists. He didn’t have any interest in investing, but he had some good feedback on our UI and our strategy. What was fun about the meeting was that in addition to meeting Paul we also met Tracy Kidder, who was then shadowing Paul for his book A Truck Full of Money, about Paul’s entrepreneurial career.
… the thing that makes English unique is his passion for helping other people through mentoring.
And just as he now mentors younger entrepreneurs, he found himself in search of mentorship when he started founding companies. “Earlier in my career I would look for someone who was not my boss — maybe my boss’s boss or a peer or someone outside the company. Scott Cook, who cofounded Intuit, continues to be my mentor,” said English.
He gave me several examples of how mentoring helped him be a better manager. “Mentors helped me understand that when working with a cofounder, it is better to split a startup’s equity 50/50 because when things get challenging you will both be highly motivated to find a solution.
Finally, mentors helped me appreciate how important it is to seize every customer interaction as a learning opportunity
Paul introduced author Peter Cohan to four people who talked with him about mentoring.
Vinayak Ranade English mentored Ranade through his example and coaching — teaching him the importance of hiring the best team.
Sara Wood, He gave me advice on scaling companies; the legal obligations of an executive; and how to read the capitalization tables in a Series F fund raising to ask tighter questions. He’s helped me raise money by serving as a reference for investors conducting due diligence. And he’s helped me to give better performance reviews to build trust on both sides.He also taught me the importance of thinking and being like the customer.”
Polina Raygorodskaya, Paul helped me to understand why branding was important and how Kayak built its brand. He also introduced me to his VP of Engineering to find out how they integrated with their partners.”
David Cancel Mentoring is a way for humans to simulate how they might act by using other people’s 10, 20 or 30 years of experience to model where the might want to be in the future. Paul helped me to learn the importance of people — particularly recruiting experienced people in areas like sales leadership and finance. By taking a long view of how I can help them achieve their career goals, I have gotten better at overcoming the challenges of hiring such people.”
I love David Cancel’s quote about mentoring as a simulation! I’ve never heard anyone express mentoring in that fashion and it’s a great way to think about it.
Paul English sets a great example for other CEOs who “have made it” by paying back through his mentoring of other entrepreneurs. And, from the examples given by the four founders, his advice is gold plated. Not exactly, a truck full of money, but perhaps by following it you will get your own truck full, or at least a wheel barrow’s worth.