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  1. The GaryVee Audio Experience
  2. The Fastest way VS The Happiest Way To Make Money
The Fastest way VS The Happiest Way To Make Money

The Fastest way VS The Happiest Way To Make Money

The GaryVee Audio Experience · Nov 18, 2025

Success isn't about speed. Gary Vee discusses the power of self-awareness, kind candor, hiring fast, and monetizing your passions.

Avoiding Candor Creates Entitlement and Resentment

A leader's failure to deliver difficult feedback, even with good intentions, doesn't protect employees. It fosters entitlement in the underperformer and resentment in the leader, leading to a toxic dynamic and an inevitable, messy separation. True kindness is direct, constructive feedback.

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The Fastest way VS The Happiest Way To Make Money

The GaryVee Audio Experience·3 months ago

Hire Fast, Fire Faster, and Promote Fastest

Challenge the 'hire slow' mantra. Hiring is an intuitive guess, so act quickly. Once a person is in the organization, their performance is a known fact, not a guess. This clarity allows for faster decisions—both in removing underperformers and, crucially, in accelerating the promotion of superstars ahead of standard review cycles.

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The Fastest way VS The Happiest Way To Make Money

The GaryVee Audio Experience·3 months ago

The Fastest Path to Wealth is Rejecting 'Fast'

Chasing trends for quick financial gain is a trap. The most effective and sustainable path to $100k is monetizing what you are genuinely good at and passionate about. This approach builds a joyful, long-term business rather than a stressful, short-term gamble on things you don't truly love.

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The Fastest way VS The Happiest Way To Make Money

The GaryVee Audio Experience·3 months ago

Cross-Pollinate Audiences for Local Business Growth

The Taylor Swift/Travis Kelce effect demonstrates the power of combining disparate audiences. For a local business, this means collaborating with another non-competing local business (e.g., a mechanic and a restaurant). This strategic cross-pollination can unlock significant growth by exposing each brand to an entirely new customer base.

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The Fastest way VS The Happiest Way To Make Money

The GaryVee Audio Experience·3 months ago

Successful Early-Stage Investing Requires a 'Two for Two' Mandate

When making early-stage investments, avoid the common pitfall of betting on just a great idea or just a great founder. A successful investment requires deep belief in both. Every time the speaker has invested with only one of the two criteria met, they have lost money. The mandate must be 'two for two.'

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The Fastest way VS The Happiest Way To Make Money

The GaryVee Audio Experience·3 months ago

Your First 100 Hires Are Your Scalable Culture Engine

To scale from 100 to 1,000+ employees, you must stop interviewing everyone. Success depends entirely on the cultural foundation built with the first 100 people. By personally hiring and imbuing them with the company's core values, you create a group of leaders who can replicate that culture as the organization expands.

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The Fastest way VS The Happiest Way To Make Money

The GaryVee Audio Experience·3 months ago

Your Biggest Mistakes are the Opportunities You Never Saw

While it's easy to regret known bad decisions, like passing on an investment, the far greater mistakes are the unseen ones. The meeting you canceled or the connection you didn't pursue could have been the pivotal moment of your career. This mindset liberates you from the fear of making visible errors and encourages action.

The Fastest way VS The Happiest Way To Make Money thumbnail

The Fastest way VS The Happiest Way To Make Money

The GaryVee Audio Experience·3 months ago