6 Things I have Learned as The Assistant to a Serial Entrepreneur

Today marks the final day of my tenure as the Executive Assistant to Dave Kerpen, as I transition into the role of Vice President of Sales for his company Apprentice.

For those who haven't heard of Dave Kerpen - I strongly encourage that you read about him or grab a copy of one of his NYT best-selling books, Likeable Social Media, or The Art of People.

After briefly connecting with Dave in person, and reaching back out online - I was asked to participate in an interview with his business partner, and former EA, Rob Berk, for their latest venture, Apprentice.

From there, I became the assistant to Hugh Morganbesser of Likeable Local, and later the assistant to Dave himself, and business partner on Remembering.Live.

My journey with Dave has been a rollercoaster in many ways, from closing large speaking arrangements for Dave, onboarding new clients for Apprentice, organizing large summits, planning TV shows, and building a business together, I have also made costly mistakes, through a lack of better understanding, short-sightedness, and at times being a poor listener and coachee.

I have grown tremendously as an entrepreneur, leader, and communicator. Not only have my aspirations become more real, and my career grew stronger, I have matured and developed emotionally and interpersonally both in my professional and personal life.


Here are my key takeaways of things I have learned working with Dave:

1. Listen to understand, and not to respond. One skill I have worked my hardest at improving is listening. Often times, over-confidence in our words, and self-belief about being right can paradoxically lead to failing both when receiving advice from others, and when attempting to provide our advice to them. We live in a very noisy world, where everybody assumes their opinion is valid, and everybody wants to contribute to the world through their voice. Ironically, I was very quick to vocalize my objection to Dave's enthusiasm for mirroring and validation. How can simply repeating what others are saying, and validating their feelings (even when they are wrong) be the solution to our problems? Whilst, I can't remember the pivoting moment when I realized how wrong I was - I can say, I have handled challenging sales objections, eased the anxiety of frustrated clients, maintained confidence and motivation in my teams, and saved friendships from going south. I was very recently able to build a genuine connection with someone from school, whom I have spent years in conflict with. How? I listened, and I understood. 2. The best managers are the best coaches. People love to be coached and hate to be managed. This is why we pay coaches, and managers pay us. Dave is very successful in scaling motivated teams and ambitious entrepreneurs through being an inspiring coach, rather than a dominating manager. Dave creates ideas, goals, and vision - and then surrounds himself with people who can paint that picture into a reality. Instead of checking in with me every hour of the clock, and instructing me on every specific assignment, and each detail involved, he coaches me on how to think like Dave and like an entrepreneur. When I have made mistakes or doubted myself - he doesn't remind me of my past failures or micromanage me to perfection, he acknowledges me for who I am and uses that framework to coach me into a better employee, leader, and mentee. His advice and feedback has always come from a place of wisdom and insight, and most importantly, empathy. Dave is a coach who sincerely cares about the personal growth and professional development of me and the people he mentors. 3. Hire coachable people. There are two things that you can't teach. One is intelligence, and another is coachability. Being coachable is very hard to coach. Whilst, you might have grade A experience, and unprecedented skills - without being coachable, what you see is what you get. This has been very important to me in the process of hiring and onboarding new salespeople for Apprentice. Sales is a constant learning opportunity, and so long as you stay motivated, persistent, and likeable - you can become a great salesperson. However, even those qualities, or any specific skills necessary to build rapport, increase urgency, and close deals - they are all teachable. What is not teachable is knowing how to accept feedback and learn from your mistakes and from your mentors. I am a long way away from matching Dave's proficiency in sales - but every lesson in coaching I receive from Dave narrows that gap one phone call at a time. 4. Ideas are easy, execution is everything. We all thought of that idea that eventually sold for a billion dollars. Ideas are rarely unique or original. With over 7 billion people on the planet, the chances that our ideas exist only inside our mind is quite possibly, impossible. ~ However, executing the impossible, and turning an idea into a reality takes very few people with the determination, self-belief, and competence to do so. Dave and I have discussed lots of ideas together, including the idea to scale what was a meaningful memorial service for Dave's mom into a company that has supported over 100 families. Dave came up with the idea within one day, and the next week, we were registered, featured in the press, and serving families. This is only one of the many examples in Dave's career, where he has turned what is a great idea into a successful reality. If all that was needed were dreams to be successful, I would have woken up to a new business each morning. 5. Set boundaries, time is precious. This is one area I am worst at. So my advice mainly comes from Dave. Fridays are spent with Dave and his 6-year-old son, Seth. On Friday, whether it was a client, a prospect, an investor, a partner, or even a celebrity - nobody has access to a minute on Dave's calendar, but Seth. If I did anything to frustrate Dave the most, it would be texting or emailing him on those Fridays. Time allocation is something I am working on improving with the coaching from Dave. I often reply to emails under the table when having dinner with family, answer the phone when out with friends, and complete assignments when I should be asleep. Having no control over my hours, and creating no boundaries for my time, put me in an irreversible position of expectation from others, and an inevitable infliction of self-guilt at the time spent enjoying life. In my experience so far - unless someone is dying, most things can wait 24 hours. If you become a 24-hour gas station, you will run out of fuel fast. Honor the time you set for yourself. Family & friends, work, or you; pick one at a time. 6. Show Gratitude. Gratitude is the gift that keeps on giving and never fails to lift the mood of those giving and receiving it. At each board meeting for Remembering.Live, or cohort meeting for Apprentice, Dave asks that we close the call by naming one person we are grateful for. With that being said, I am grateful for Dave. Who are you grateful for?

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