What I Learned as a CEO From My Bosses, the Board

In this series, professionals thank those who helped them reach where they are today. Read the posts here, then write your own. Use #ThankYourMentor and @mention your mentor when sharing.

As a CEO, the board is effectively my boss. I report to them regularly, they set my compensation, and they approve significant decisions. I’ve been extremely lucky as an entrepreneur to have a board who is supportive and collaborative. After all, we share a goal of building a large, lasting and meaningful company. As a result, I regularly get to interact with and learn from some of the smartest, most insightful people in the industry. Here are a few of the lessons I’ve learned from past members of my boards:

You’re the best person for your job (from Bob Zipp, Founder at Amicus Capital)

Bob led the investment in my first company, TravelPost, and was my very first board member. As it was my first experience working with a board (let alone leading a company and taking money from others), I was a bit unsure of myself and how I should be interacting with and using the board. I relied on them too much for approval and frequently asked for permission before making decisions. Eventually Bob pulled me aside and told me that the board had invested in me, not just the company. He said that I was the best person to run this business and that the board didn’t want to get in the way or slow me down. This gave me the confidence I needed to take risks, run the business effectively, and ultimately have a great outcome for the business.

Keep your sense of humor (from Dave Pell, Managing Partner at Arba Group)

Dave invested alongside Bob and was on the board at TravelPost. Not only is Dave one of the funniest guys in the world (seriously, check out his newsletter), but nothing rattles him. Even during difficult discussions, he always maintained his cool and his sense of humor. His ability to keep things lighthearted really inspired me, and it’s something I use to lighten the mood during a difficult discussion, or when finding out bad news.

Leverage your competitive advantage (from Greg Jones, Founder & CEO of WorldRes)

I recruited Greg to be on the board of TravelPost. Greg comes from a consulting background and is extremely methodical and drawn of structural decision-making. This style isn’t always typical in startups – but when it works, it can help focus your energy. Greg was big on focusing on your competitive advantage, and at TravelPost, we realized ours was speed and ability to execute. He gave me confidence that this was a totally valid advantage to focus on, and encouraged me to lean into it and really leverage it for the growth of the company. Since then, I’ve thought long and hard about competitive advantage when starting a new venture – and look for more than just speed, which every startup should have!

Ask the tough question (from Theresia Gouw, then Partner at Accel Partners)

Theresia sat on the board of HotelTonight representing Accel, who co-led our Series A, until she left to start her own firm, Aspect Ventures. Theresia has the amazing ability to boil things down, get right at the heart of the issue, and encapsulate it into one single question. She asks the tough question, not questions. I may not be able to do exactly the same (yet), but her example encourages me to try.

Be passionate and enthusiastic – but concise (from Brad Gerstner, Angel Investor)

Brad is a good friend and a prolific online travel angel investor, and is extremely passionate about the companies he’s involved with. But he’s not only passionate – he’s also articulate, and can sum up why a company is going to win in a very concise yet enthusiastic way. I’ve known him since my TravelPost days, and have seen him do this time and time again. Seeing it from the inside at HotelTonight, where he served on the board for three years, was a great experience. I strive to bring the same spirit to any companies I’m involved with.