Gary Vaynerchuk, co-founder and CEO, VaynerMedia, sits down with Brian Stelter, senior media correspondent at CNN, to share about his entrepreneurial journey and lessons he’s learned along the way at the Techweek Chicago Summit 2015.

Gary first ventured into building businesses when he took over his family’s wine business from his father and grew it to become a $60M (previously $3M) business in a five-year span. As a young man in the mid-90s, he used to sell items in dollar stores to earn a quick buck. Gary’s success is a result of his natural talent when it comes to sales.

Some of our key takeaways from the conversation:

  1. Every Business Thrives on Money and Audience Analysis:
    Gary feels the concept of garage selling and posting the details on eBay is the “in” thing nowadays. This can allow an individual to earn at least $1000 per week. Money making is an art, but a social media agency like VaynerMedia does not spend money on marketing behavior. Gary invests in companies like Facebook, Twitter, and Tumblr, as social media provides the opportunity to re-assess an audience’s tastes as well as their likes and dislikes.
  2. Effective Time Management is the Key to Success for an Entrepreneur:
    Gary’s daily schedule rounds up to 18 hours of work, which to him is “80% of VaynerMedia, funds, and the rest is Wine Library TV and personal stuff.” In New York, an entrepreneur can’t afford to wrap up his or her work by 7pm and then relax with a cup of coffee. To create and successfully own a business on your own terms, requires hours of hard work.
  3.  Today’s Fake Entrepreneurship Creates Hindrance for Businesses in the Making:
    Gary considers the concept of entrepreneurship today to be quite vague and fake in nature. The reason being that today’s young entrepreneurs think they are capable of easily starting up their own business and getting funded quickly. Gary stresses that that is not today’s reality. Disruptive businesses not only need a strong foundation, but also an efficient sales team to make sure the products are sold to the right demographics and in the right locations.
  4. Creating and Distributing Content for Audience is Crucial:
    Be it Wine Library TV, the AskGaryVee Show, or VaynerMedia, Gary’s agencies are all in the process of content creation. The most intriguing way of creating content is through Q&A sessions. This allows a constant flow of original content every day. Gary believes that Facebook, Snapchat—although underestimated by techies—are the best platforms for distributing content.

Below are some of the key points and moments from the conversation:

  • 0:02 – Brian Stelter, senior media correspondent at CNN, introduced Gary Vaynerchuk, co-founder & CEO of VaynerMedia, to the audience
  • 0:28 – Gary shared his ideas on businesses and brands, tracing his entrepreneurial roots
  • 3:09 – Gary explained that every minute of his 18-hour day is allocated to his businesses
  • 4:20 – Lack of self-awareness and indulging in fake entrepreneurship can be quite dangerous for next-gen business owners
  • 12:30 – Re-assessing audience is critical as it involves a re-engineering method
  • 13:50 – Gary expressed interesting viewpoints on making strategies for building and distributing content
  • 19:52 – Q&A session begins


Co-founder & CEO at VaynerMedia