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Timestamps are as accurate as they can be but may be slightly off. We encourage you to listen to the full context.
This episode features Gary Vaynerchuk's fourth TikTok live session where he answers audience questions with his signature unfiltered style. (01:23) The conversation centers on building businesses based on self-awareness rather than trends, with Gary emphasizing that "the business has to be very predicated on like yourself not on a trend." (02:23) He discusses why economic conditions shouldn't dictate business decisions and explores the massive opportunities in live social shopping on platforms like TikTok Shop.
Gary Vaynerchuk is a serial entrepreneur, CEO of VaynerMedia, and author of multiple bestselling books including "Crush It!" which focuses on turning passion into profit. He built his family's wine business from $3 million to $60 million and is known for his expertise in social media marketing and authentic content creation. He also runs VaynerSports and the VeeFriends NFT project.
Gary emphasizes that successful businesses must be built on understanding your own strengths and passions rather than chasing market trends. (02:23) He explains that self-awareness involves knowing whether you're a salesperson, operator, or good at promotion and marketing. This approach leads to better execution because when you love what you do and know yourself, you have a better chance of creating a sustainable business. The key is focusing on what you're good at, what you know, and what you care about rather than jumping into trendy sectors like cannabis or crypto without the right foundation.
Gary firmly states that "the economy should have no impact on what kind of business you start" because great companies have been started in poor economies and horrible companies in great economies. (01:36) He demonstrates this by showing that even "declining" markets like craft beer still represent massive opportunities - the US craft beer market reached $28.9 billion in 2024. Even a tiny fraction of such markets can provide substantial income for new entrepreneurs, proving that market size often trumps market trends.
Gary stresses that "you have to post content at scale everybody. At scale." (11:50) He emphasizes posting on main feeds rather than just stories, and recommends three posts per day for anyone trying to build a business. The more you post, the luckier you get, and this applies across all platforms. He also highlights the critical importance of engaging with your audience by replying to comments and DMs, sharing that from 2007-2011 he replied to every single tweet and email he received.
Gary identifies live social shopping, particularly on TikTok Shop, as a "monster" opportunity for entrepreneurs. (02:12) He demonstrates this by going live himself and shows how easy it is to start - "you could do it right here. I'm doing it from a phone right now." This strategy combines content creation with direct sales, allowing entrepreneurs to build brand awareness while generating immediate revenue through product sales during live streams.
When asked about overcoming years of bad habits, Gary's immediate response is "accountability." (07:19) He explains that you must take 100% responsibility for your bad behavior, regardless of circumstances like family history or trauma patterns. Gary argues that someone has always broken every trauma pattern before, so you can be the first in your generation to do it. This mindset shift from victim to owner of your outcomes is essential for creating lasting change.