04.01.20 | Timestamp @1:00 | 10 People, 10 Problems, 1 Exceptionally Good Listener


Leon Benjamin



Leon’s Question or Topic

Leon is a social media coach who founded Triple Your Tribe that offers service packages to fitness coaches and other entrepreneurs who would love to use Instagram or other media platforms to expand their businesses. Leon asks Gary about the things that a number three or number four person in business should look like in terms of putting content and getting himself to the world. He asks this question because he feels like he is falling out of love of social media coaching, and now he wants to produce content to give him leverage to be hired as a number three or four.

Gary’s Story and Advices

Gary understands Leon’s situation of not being excited every morning about his current job and it’s something that he is proud of talking about because he is trying to create permission and self-awareness of not becoming an entrepreneur in a world where if someone is under 40, he almost feels like he has to be, which is crazy. Entrepreneurship almost becomes like school and college, where everyone thinks somebody has to be one.

Gary advises Leon that he should make a list of 25 businesses and 25 entrepreneurs he most admires. Because one of the things he can consider is spending a couple of weeks just analyzing those businesses. And focus on the entrepreneur in the sector that Leon enjoys the most. Gary introduces two things to do:

  • Creating a post on LinkedIn or actually creating content about certain businesses. He cited an example – “The three things I see The Grapefruit Shop can fix on social media.”
  • Writing an email saying that Leon admires someone’s business from afar for a long time, telling a bit about himself and offering anything he can do pro-bono.
  • Writing an email similar to a blog post putting down his analysis on the business’s social media account, therefore adding value to the company.

Gary also emphasized that to settle the problem on the lack of passion, Leon must shift his engagements on the things he is interested in such as what he mentioned that he liked vegan food and the chefs who make them.

Gary Vaynerchuk’s Quotes


“Entrepreneurship has almost become like school and college. Everyone thinks you have to.”
~ Gary Vaynerchuk


“Make a list of the 25 businesses and 25 entrepreneurs you most admire.” ~ Gary Vaynerchuk


“Figure out who you admire.” ~ Gary Vaynerchuk

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