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BigDeal by Codie SanchezThe Biggest Bets I Made — And How They Paid Off: Gary Vee
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Chapter summaries
How Gary Vets Founders: The Jockey and the Horse
Codie asks how Gary smells a founder who will win. Gary explains his early intuition-led investments in Facebook, Twitter and Tumblr, the era where he lost by betting on ideas alone, and his current jockey-and-horse lens.
- •Early investments in Facebook, Twitter and Tumblr were made on intuition about the person and thesis
- •A three-year era of backing ideas over people led to losses, such as Yobongo
- •Now he looks at both the jockey (entrepreneur) and the horse (business)
- •His opening interview prompt is simply "tell me everything," then he counterpunches what he hears
Hiring B and C Players, and the Candor Problem
Gary explains how fast he can read people and why he is happy to hire C players he can level up to Bs, as long as their personality is strong. He also admits his struggle giving critical feedback and firing people.
- •He can quickly tell a standout from an average C player
- •Wants an A+ personality in a C player, since a C personality is death on arrival
- •Asks candidates for a real shortcoming and dismisses answers like "I care too much"
- •Lack of candor as an executive led to sloppy firings and inspired his book 12 and a Half
Insecurity, Over-Coddling and His Mom's Influence
Asked what advice people refuse to hear, Gary rails against giving adult kids money and against labels like anxiety and imposter syndrome. He then describes how his mother accepted his bad grades and put him to work.
- •Paying for grown children tells them you don't believe in them
- •Big clinical-sounding words give people permission not to fight and fix
- •His mom ignored his D's and F's and told him at 14 that now he works
- •Baseball card shows gave him validation when school did not
Merchandising and Thinking Like a Consumer
Gary explains merchandising through his baseball card dollar rack and his dad's store, and how the same instinct carried into early internet UX and abandoned-cart emails. Codie adds her Harry Potter store observation.
- •The dollar rack with a huge sign cleared cards that couldn't otherwise move
- •Eye-level placement sells; he moved a difficult supplier's products to the bottom shelf
- •Watching shoppers in his dad's store shaped his UI/UX instincts
- •In 2000 he had abandoned-cart emails built, which crushed
Scale the Unscalable and the 10/80/10 Framework
Gary says early creators should reply to every DM, and describes how he scales Vayner with 10/80/10: involved in the first and last 10% while avoiding the middle. He also reconsiders his 15-minute meeting rule.
- •Reply to every comment and DM early; he replied to everyone on Twitter from 2007 to 2011
- •10/80/10 means opening and closing important work while staying out of the middle
- •He realized some hour-long meetings need two to three hours and is doing more off-sites
- •Small business owners often lose by spending all their time in the 80
What Young Entrepreneurs Are Sleeping On
Asked what young entrepreneurs are missing, Gary points to outside validation, trend chasing and impatience. He argues people should build around what they love and work in an industry first, and he lists the businesses he runs.
- •Youth crave validation from the masses through Lambos, watches and followers
- •People chase trends like crypto or flipping instead of what they truly like
- •Loving what you do makes you persevere through daily grind
- •He had nothing at 34 and started VaynerMedia in a borrowed conference room; it is now 2,000-plus people and $350 million in annual revenue
- •Most people aren't talented enough in their teens or 20s to build a viable business yet
How Hard Wealth Is and the Problem with Flexing
Prompted by Codie's stat on how rare it is to earn a million a year, Gary says it is far harder than people think, partly because feeds distort perception. They discuss sports and business as merit systems and why flashy displays worry him.
- •Codie cites odds of one in 1,000 making over a million in a year
- •Constant feeds of watches and vacations make success look easy; he says to stop consuming them
- •Sports is the most merit-based system, with business next closest
- •Flashy posts are often selfish funnels, and over-indexing on them tends to make people less happy
The Laundromat Playbook: Content and Store as Studio
Given one laundromat, Gary says he would build content and a personal brand, learning to run ads along the way. He and Codie argue the business itself is the best studio and that production value is often an excuse.
- •Personal brand is a moat that doesn't get commoditized, even in an AI world
- •Local businesses should run 10-mile radius Facebook ads
- •Store as studio: the best studio is the world, and he started Wine Library TV with no mic or lighting
- •Production often disguises insecurity; an iPhone is enough
Dealing with Haters and the Value of Competition
Codie asks how he handles haters. Gary answers with compassion and indifference plus a bit of competitive fire, and argues that winning and losing matter and that teaching kids nothing matters is dangerous.
- •He couldn't comprehend spending time tearing someone down
- •Noticed A players privately envying other A players, which he reads as insecurity
- •His approach is roughly 90% indifference and compassion and 10% competitive fire
- •Eliminating merit and competition is dangerous; he links nihilism to a dark place and says passion is what he can smell in people
Finding Social Media Talent and Learning It Yourself
Codie raises the common question of how to find great social talent. Gary says owners must first learn the platforms themselves, spending 50 to 100 hours, rather than handing it to a young relative, and points to his free deck and book Day Trading Attention.
- •You can't judge talent in something you don't understand
- •Handing social media to a 20-year-old niece is a common mistake
- •Spend 50 to 100 hours learning and doing, not just reading
- •GaryVee.com/attention offers a free 44-page deck based on his latest book
- •He writes contemporary rather than evergreen books
Where Underpriced Attention Is Today: Live Social Shopping
Gary names live social shopping, on TikTok Shop and Whatnot, as the biggest underpriced attention right now. He gives examples like garage sales and his own mug, cites China's numbers, and then covers Snapchat Spotlight, Substack and similar platforms.
- •Anyone selling physical products should learn TikTok Shop and Whatnot
- •Mike's Whatnot garage sale made about $648 from household items
- •He cites live shopping as roughly 30% of e-commerce in China and says QVC's CEO put the US at 6%
- •Commercetainment: selling subtly while entertaining, like pinning his VeeFriends mug
- •Snapchat Spotlight has low supply of posters; he is also eyeing Substack and Beehiiv-style platforms
AI Predictions: Oxygen, Daily Use and Robot Spouses
Gary says his craziest prediction is that many people's grandchildren will marry AI robots, and calls AI as foundational as the internet. He recommends daily use, cautions investors about how fast apps change, and argues that technology can't be stopped.
- •AI is like oxygen or infrastructure, a level above the internet
- •Use tools like ChatGPT, Perplexity or Gemini daily, for example to ask which AI apps popped this week
- •He is cautious about investing in AI because the best app changes every week
- •Predicts agent-driven shopping, real-time translation earpods and robot companions
- •Technology is undefeated, and people feared electricity at first
