How to Win Again: AI, Fear, & What People Get Wrong About Success | Tea with GaryVee 94

How to Win Again: AI, Fear, & What People Get Wrong About Success | Tea with GaryVee 94

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Prosperity Pathway
9 Video Views·Jan 1, 2026  #garyvee #teawithgaryvee #mindset

Today’s episode is Tea with GaryVee ep. 94, where I go deep on fear, insecurity, and why so many people are currently losing because they’re surrounded by the wrong people. I talk about taking full accountability for your life, breaking generational coddling, and why getting punched in the mouth by adversity is actually the foundation of real strength. Hope you enjoy!

01:18 – Interview confidence, honesty, and getting rid of insecurity
05:01 – Parenting, coddling, and why kids avoid losing
08:20 – You're not a loser,you’re just currently losing
11:36 – Growing a small-town business and using local Facebook ads
13:56 – Emotional intelligence and real human skills in the AI era
17:32 – Why people value “50 no’s” but not “50 views”
21:05 – Cutting negativity, breaking cycles, and shifting your mindset
23:03 – Dealing with trolls, insecurity, and emotional strength
32:06 – Therapy, letting out your poison, and clearing emotional weight
36:18 – Crushing content anywhere (even if your country’s features differ)
43:10 – Losing a spouse, resilience, and finding strength again
49:18 – Real adversity vs. fake problems

#garyvee #teawithgaryvee #mindset #accountability #entrepreneurship #motivation #parenting #relationships #vulnerability #ai #socialshopping

Thanks for watching!

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Gary Vaynerchuk is a serial entrepreneur and serves as the Chairman of VaynerX, the CEO of VaynerMedia, and the CEO and creator of VeeFriends. Gary is considered one of the leading global minds on what's next in culture, business, and the internet.

Known as "GaryVee," he is described as one of the most forward thinkers in business. He acutely recognizes trends and patterns early to help others understand how shifts in consumer attention impact the realities of the business world today. Gary's approach sits at the intersection of business and pop culture. He keenly understands how to bring brand relevance to the forefront. He is a prolific angel investor with early investments in companies like Facebook, Twitter, Tumblr, Venmo, Snapchat, Coinbase, and Uber.

Gary is an entrepreneur at heart – he builds businesses. Today, he helps Fortune 1000 brands leverage consumer attention through his full-service advertising agency, VaynerMedia, which has offices in New York, Los Angeles, Chicago, Miami, Toronto, Mexico City, London, Amsterdam, Sydney, Singapore, Tokyo, Bangkok, Delhi, and Kuala Lumpur. VaynerMedia is part of the VaynerX holding company, which also includes Eva Nosidam Productions, Gallery Media Group, The Sasha Group, VaynerSpeakers, VaynerCommerce, and Tingley Lane Trading. Gary is the Co-Founder of VaynerSports, VCR Group, VaynerWatt, ArtOfficial, Resy, and Empathy Wines. He guided Resy and Empathy to successful exits -- which he later sold to American Express and Constellation Brands, respectively. He also owns a Major League Pickleball team called the 5s, is part owner of a Big3 basketball team, and is an investor in the revival of the SlamBall League.

In 2021, Gary created VeeFriends, an entertainment company that has become a rising powerhouse in modern entertainment and collectibles. Often described as Pokemon meets Sesame Street, the company leverages stories, games, events, collectibles, and technology to scale its character universe. Vaynerchuk also has negotiated partnerships with brand powerhouses such as Crocs, Fanatics, Macy’s/Toys “R” Us, Mattel’s UNO, Mattel’s Masters of the Universe, Moonbug Entertainment, Reebok, Squishmallows, Topps, and more.

Gary is also the founder and creator of VeeCon – a contemporary super conference that converges business and pop culture with innovation and technology. He is a six-time New York Times bestselling author, with titles including Crush It!, Jab, Jab, Jab, Right Hook, Twelve and a Half and Day Trading Attention. In addition to running multiple businesses, Gary documents his daily life as a CEO through his social media channels, which have more than 45 million followers and garner more than 300 million monthly impressions/views across all platforms. His podcast, "The GaryVee Audio Experience," ranks among the top podcasts globally.

Gary serves on the board of MikMak, Bojangles Restaurants, Global Citizen Forum, The Paley Center, and Pencils of Promise. He is also a longtime Well Member of charity: water.

Gary's life ambition is to buy the New York Jets.

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