Gary Vaynerchuk: Fear, Candor, and Building a Personal Brand in the AI Era
Post Run High
iHeartPodcasts
1.1 • 4.5K Ratings
🗓️ 24 November 2025
⏱️ 34 minutes
🧾️ Download transcript
Summary
Gary Vee reveals the mindset and resilience that took him from a Jersey kid hustling baseball cards to building Wine Library into a $65M business and launching VaynerMedia. He breaks down the confidence he developed early, the immigrant values that shaped his work ethic, the health transformation that changed his approach to fitness, and why mastering personal branding and adapting to AI is now essential for entrepreneurs and creators. Gary also opens up about the one leadership skill he wishes he learned sooner — candor — and how it would have saved him years of personal and professional frustration. Packed with insights on business growth, self-awareness, and the future of media, this episode gives you the motivation and strategy to level up your career.
Post Run High Instagram: https://www.instagram.com/postrunhigh/
Kate Mackz YouTube: https://www.youtube.com/@KateMackz
Kate Mackz Instagram: https://www.instagram.com/katemackz/
See omnystudio.com/listener for privacy information.
Transcript
Click on a timestamp to play from that location
| 0:00.0 | When people are talking, if they're talking about my career, it's that I understood when there was |
| 0:04.6 | consumer shifts. I think I understood what life was about at 12, and I wasn't willing to listen to any |
| 0:10.0 | grown up that wasn't my mom telling me that I wasn't shit. Your family in New Jersey had a liquor brand. |
| 0:15.4 | You took it from like a $3 million business to $65 million. I was early in understanding the power of personal brand as a |
| 0:24.2 | business leverage. I knew the internet was a big one and I bet the farm on it. Did you ever have a |
| 0:28.4 | moment of doubt? Doubt doesn't scare me. I'm not scared to lose my reputation. I'm not scared to be |
| 0:33.5 | judged by other people. When you're not scared, you're dangerous. What's up, guys? It's Kate Max, |
| 0:39.9 | and today I'm chatting with entrepreneur, investor, and social media pioneer Gary Vaynerchuk on |
| 0:45.8 | post-run high. Don't go anywhere. We will be right back after this short break. |
| 0:53.8 | This is an I-Heart podcast. |
| 0:56.7 | Guaranteed human. |
| 1:01.5 | Gary V, welcome to post-run high. |
| 1:03.5 | Thank you for having me. |
| 1:04.6 | Post-walk high today. |
| 1:05.7 | Yes, post-walk. |
| 1:06.7 | So Gary and I just went for a stroll on the high line. |
| 1:10.2 | I haven't walked on the high line in probably years. |
| 1:12.9 | I'm glad we did it. |
| 1:13.6 | So it was special. |
| 1:14.6 | Good. Although I was kind of bummed. We didn't see the big pigeon statue. Yeah, that was to the side. I knew when you said it, but I wanted to make, you told me to go tight on those answers. I didn't want to sidetrack and tell you where the pigeon was. You were very tight on the answers. |
| 1:25.5 | And I know you're typically like a long-winded death of guy. |
| 1:27.6 | Yes, I like a good, deep contextual answer. |
... |
Please login to see the full transcript.
Disclaimer: The podcast and artwork embedded on this page are from iHeartPodcasts, and are the property of its owner and not affiliated with or endorsed by Tapesearch.
Generated transcripts are the property of iHeartPodcasts and are distributed freely under the Fair Use doctrine. Transcripts generated by Tapesearch are not guaranteed to be accurate.
Copyright © Tapesearch 2026.