Tips From The Top: One On One With Roy Sekoff

I spoke to Roy Sekoff, founding editor of the Huffington Post and co-creator of HuffPost Live, about his journey and his best advice

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Adam: Thanks again for taking the time to share your advice. First things first, though, I am sure readers would love to learn more about you. What is something about you that would surprise people?

Roy: Here’s a shameful admission from an editor: I am an atrocious speller. If my life depended on being able to correctly spell “lieutenant,” “architect,” or “chauffeur” without the aid of spellcheck, you might as well start taking measurements for my casket.

Adam: How did you get here? What failures, setbacks or challenges have been most instrumental to your growth?

Roy: I got here (and by that I mean right here within a “Tips from the Top” column) through a combination of luck, talent, stubbornness, desperation, a willingness to take risks, the patience to play “the long game” when it came to my career, and parents who supported me – both emotionally and financially – long after it made sense to do so.

My life has been chockfull of disappointments and failures. These were often quite painful, until I belatedly realized that it was foolish to judge these perceived setbacks too hastily – and that the thing I saw as a failure might actually turn out to be an amazing opportunity. A case in point: after my screenwriting career hit a lull, I stumbled into an eight-week job working for Arianna Huffington – an eight-week job that ended up lasting 17 years and put me on a path to HuffPost, a completely unexpected stint as a media executive, and, eventually, my new adventure as an author.

Adam: In your experience, what are the defining qualities of an effective leader? How can leaders and aspiring leaders take their leadership skills to the next level?

Roy: The most effective leaders I’ve seen (and tried to emulate) motivate by inspiration rather than dread; revel in the success of those they manage (rather than fear and resent it); see their team as people first, employees second; and lead by example, rolling up their sleeves and working harder than everyone else. They also dream big — and pursue those dreams with passion and relentlessness.

Adam: What are your three best tips applicable to entrepreneurs, executives and civic leaders?


1. Trust your instincts (in the end, your gut is usually right).

2. Follow your passion (otherwise what’s the point?)

3. Never forget to laugh (especially at yourself).

Adam: What is the single best piece of advice you have ever received?

Roy: My dad, who was the most influential person in my life, used to always tell anyone who asked for advice: “One word: ‘read’.” He felt reading was both the master key that allowed you to enter any world and a weapon that enabled you to slay the darkest foe: ignorance.

I was also once given a greeting card that said: “Life is about the people you meet and the things you create with them, so go out and start creating.” That still works.

Adam: What is one thing everyone should be doing to pay it forward?

Roy: I hate to go all Golden Rule on you, but treating people the way you wish you’d been treated when you were younger/starting out is still a damn good approach.

Adam: What are your hobbies and how have they shaped you?

Roy: I love to read (thanks, Dad!); it feeds my mind. I love to ride my bike; it feeds my body. I love to make people laugh (is that a hobby?); it feeds my spirit.

Adam: Is there anything else you would like to share?

Roy: I’m a big believer in coloring outside the lines; in being willing to risk looking foolish—and embracing it when you do; in questioning authority; in speaking up and speaking out; in frequently asking “Why?”; in frequently saying “Why not?”; in understanding that daydreaming isn’t wasting time, it’s a high-intensity workout for your imagination; and in taking the road less traveled, even though it often has massive potholes, scary-looking hitchhikers, and many long, lonely stretches.

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