On our most replayed episode, Gary ‘Vee’ Vaynerchuk talks about how being scrappy wasn’t just a choice for him; it was his only way forward. After years of growing his family’s wine business, he was left with nothing of his own. With no money to rent an office or hire employees, Gary leveraged his grit, relationships, and opportunities to launch VaynerMedia.

Overcoming the financial, mental, and emotional hurdles of entrepreneurship, he built his company into a multi-million-dollar media empire. In this episode, Gary joins Ilana to reveal the mindset and strategies you need to overcome obstacles and build your own multi-million-dollar business.

Gary Vaynerchuk, famously known as GaryVee, is a serial entrepreneur, chairman of VaynerX, CEO of VaynerMedia and VeeFriends, and a six-time New York Times bestselling author. Recognized as one of the most forward-thinking minds in business, culture, and the internet, Gary helps brands stay ahead by spotting trends early.

In this episode, Ilana and Gary will discuss:

(00:00) Introduction 

(01:40) VaynerMedia's Scrappy Beginnings

(06:56) Why Businesses Fail Financially

(10:01) Navigating Tough Business Days

(17:21) The Risk of Over-Transparency in Leadership

(19:44) Dealing with Failure and Public Ridicule

(22:10) GaryVee’s Dream of Owning the New York Jets

(26:06) The Role of DNA and Accountability in Success

(28:35) Finding Joy in Entrepreneurship

(31:02) How to Build a Personal Brand as an Employee

(32:30) Empowering Employees with Honest Feedback

(34:27) Embracing Change and Executing Relentlessly

Gary Vaynerchuk, famously known as GaryVee, is a serial entrepreneur, chairman of VaynerX, CEO of VaynerMedia and VeeFriends, and a six-time New York Times bestselling author. He is a prolific angel investor with early investments in companies like Facebook, Twitter, Tumblr, Venmo, Snapchat, Coinbase, and Uber. Recognized as one of the most forward-thinking minds in business, culture, and the internet, Gary helps brands stay ahead by spotting trends early.

Connect with Gary:

Gary’s Website: ⁠garyvaynerchuk.com⁠ 

Gary’s LinkedIn: ⁠linkedin.com/in/garyvaynerchuk⁠ 

Resources Mentioned:

Gary’s Book, Day Trading Attention: How to Actually Build Brand and Sales in the New Social Media World: ⁠https://www.amazon.com/Day-Trading-Attention-Actually-Social/dp/0063317591⁠ 

GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire: ⁠https://podcasts.apple.com/us/podcast/garyvee-from-earning-%242-an-hour-to-running-a/id1701718200?i=1000689595539⁠