The Hardest Lesson I've Ever Learned | 20VC Podcast

Our reading notes on Gary Vaynerchuk

• Why You Need to Forget Your “Mistakes” and Focus on Your Next Thing

  The episode listing describes Vaynerchuk’s conversation with CRWD founder Ryan Chen about paying people to try products, visit a store and give feedback. For someone planning a sampling day, that raises two separate questions. Did someone take the free sample, and did the experience give them a reason to look for the product again?

• The Real Reason Why You're Not Winning on Social Media

  Vaynerchuk’s episode notes connect two jobs a livestream can do. During a shopping session a host can respond to a question as it arrives. Later, the answer can reach someone who missed the session. The edit needs to restore the product, the question and any qualification that viewers saw earlier in the stream.

• How to Grow a Your Brand on Social Media in 2027

  In the publisher’s account of his conversation with the founders of fashion label Nude Project, Vaynerchuk raises their concern about overexposure alongside live shopping and discoverability. Seeing the same campaign repeatedly inside the company can make a collection feel familiar before a prospective customer even knows it exists.