Dave Kerpen is a serial entrepreneur, New York Times Best-Selling Author, and Global Keynote speaker. He currently works as the Co-Founder and CEO at Apprentice, a platform that connects entrepreneurs that are looking for a driven Executive Assistant that is committed to professional growth and Remembering Live, a company that provides virtual memorial services, shivas, wakes, websites. Kerpen is also the President of the Entrepreneurs’​ Organization, a nonprofit organization helping entrepreneurs achieve their full potential in their business and personal lives.

Where did you grow up and what was your childhood like? Did you have any particular experiences/stories that shaped your adult life?

I grew up in Brooklyn, New York in the 1980s in the diverse neighborhood of Sunset Park. I was one of the only Jewish families in our neighborhood and took a bus to a public magnet school 30 minutes away. My dad has chronic bipolar disorder, and his illness deeply impacted my childhood, as I became independent and learned to take care of my two younger brothers by the age of 13.

What is something you wish you would’ve realized earlier in your life?

I wish I had written more, earlier. I’ve published 4 books and over 1,000 articles but didn’t start writing until I was 30. If I’d started at 15, I’d have done twice as much. I wish I had taken more risks, earlier – asked more girls out on dates, and become an entrepreneur earlier. The only way to get to a YES is to ask.

What are bad recommendations you hear in your profession or area of expertise?

Always be closing. Better: Always be listening and asking good questions.

Tell me about one of the darker periods you’ve experienced in life. How you came out of it and what you learned from it?

The darkest period in my life was when I was in love with a married woman who I worked with at Disney in Boston. She loved me too but was committed to her husband and trying to make her marriage work. It took a lot of hard work in therapy, but I learned to let go of the desire to have her leave her husband for me since I couldn’t control it. The lesson of learning to let go of what we cannot control is an important and challenging one!

As a nice epilogue, she moved to New York to focus on her marriage, and I left Disney to go on the reality TV show Paradise Hotel to find true love. A year and a half later, I called her up and she had left her husband independently of me. We began dating, and 17 years, 1 marriage, 3 kids, 5 businesses, and 5 books later, we had a pretty happy ending.

What is one thing that you do that you feel has been the biggest contributor to your success so far?

Being genuinely curious about people’s problems and my own, listening to understand vs to reply, and always thinking about solving these problems.

What is your morning routine?

My 5 ½-year-old son wakes me up at 7:00 am every morning, and I play with him ferociously for 90 minutes while downing coffee, and take him to the school bus at 8:30.

What habit or behavior that you have pursued for a few years has most improved your life?

The most important habit I have is the consistent practice of feeling and expressing gratitude. It’s been a total game-changer for me with respect to improving my mood, my relationships with others, and my productivity. I write thank you cards, make gratitude lists, and go around the dinner table every night with my family sharing who we are grateful for.

What are your strategies for being productive and using your time most efficiently?

Most important is saying NO to meetings and opportunities which are off focus. I always try to keep meetings short as well (15 minutes vs 30, or 30 vs 60). Finally, I start “next steps” during my meetings:

What book(s) have influenced your life the most? Why?

Give and Take by Adam Grant and The Go-Giver by Bob Burg helped to reinforce the notion that givers gain. How to Win Friends and Influence People by Dale Carnegie inspired me to write The Art of People and to continue to work on my people skills.

Do you have any quotes you live by or think of often?

I had no idea that being your authentic self could make me as rich as I’ve become. If I had, I’d have done it a lot earlier. – Oprah Winfrey

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