By skyforbes 1. "What am I overthinking that I should just be testing?"
Pure GaryVee action bias. AI cuts through analysis paralysis. "I've been planning my side hustle for 6 months. What am I overthinking that I should just be testing?" Kills perfectionism instantly.
2. "What would I do if I actually gave a shit?"
His signature wake-up call. "My social media engagement is terrible. What would I do if I actually gave a shit?" AI delivers the brutal honesty you need.
3. "Where am I making excuses instead of moves?"
GaryVee's excuse destroyer. "I don't have time to create content. Where am I making excuses instead of moves?" AI spots your self-sabotage patterns.
4. "What would documenting instead of creating look like?"
His content philosophy applied everywhere. "I think I need a perfect YouTube setup. What would documenting instead of creating look like?" Suddenly you're shipping daily.
5. "How would I attack this if I had nothing to lose?"
Risk-taking mindset activation. "I'm afraid to pitch this client. How would I attack this if I had nothing to lose?" AI removes your safety governor.
6. "What's the work I'm avoiding because it's uncomfortable?"
GaryVee on eating your vegetables. "I love strategy but hate outreach. What's the work I'm avoiding because it's uncomfortable?" AI identifies your growth edge.
The breakthrough: Gary Vee proved that execution beats strategy every time. AI helps you stop planning and start doing.
Power technique: Stack the accountability. "What am I overthinking? Where am I making excuses? What work am I avoiding?" Complete execution audit.
7. "What would I do if I were already 10 steps ahead?"
Future-state operating mentality. "I'm waiting to feel ready. What would I do if I were already 10 steps ahead?" AI fast-forwards your mindset.
8. "How can I provide value before asking for anything?"
Jab, jab, jab, right hook philosophy. "I want to network but feel awkward. How can I provide value before asking for anything?" AI designs your value-first strategy.
9. "What platform am I ignoring where my audience actually is?"
Meet people where they are, not where you wish they were. "I only post on LinkedIn. What platform am I ignoring where my audience actually is?" AI finds your attention arbitrage.
Secret weapon: Add "Gary Vee would attack this by…" to any business or career challenge. AI channels pure hustle energy and zero-excuse thinking.
10. "What would I do right now if failure wasn't permanent?"
GaryVee's long-game perspective. "I'm terrified of looking stupid. What would I do right now if failure wasn't permanent?" AI removes fear of temporary setbacks.
Advanced move: Use for personal brand building. "What's my unique voice and how do I 10x my output?" GaryVee's formula for breaking through noise.
11. "Where am I consuming instead of creating?"
Producer vs. consumer mentality check. "I spend 4 hours daily on TikTok. Where am I consuming instead of creating?" AI flips your input-output ratio.
12. "What would doubling down on my strengths look like?"
Self-awareness meets execution. "I'm good at video but force myself to write. What would doubling down on my strengths look like?" AI optimizes your natural advantages.
13. "How would I approach this if patience and speed both mattered?"
Macro patience, micro speed. "I want quick results but know building takes time. How would I approach this if patience and speed both mattered?" AI balances GaryVee's paradox.
I've applied these to content creation, business building, networking, everything. It's like having the most high-energy entrepreneur in the world personally holding you accountable.
Reality check: GaryVee's intensity isn't for everyone. Add "at my sustainable pace" to avoid burnout while keeping the execution focus.
The multiplier: These work because Gary Vee's philosophy is about closing the gap between thinking and doing. AI helps you identify that gap and destroy it.
Mind shift: Use "What would I ship today if done was better than perfect?" for any project. GaryVee proved that volume and consistency beat waiting for perfect.
14. "What story am I telling myself about why I can't?"
Limiting belief assassin. "I think I'm too old to start. What story am I telling myself about why I can't?" AI destroys your narrative excuses.
15. "Where am I playing small because I'm comfortable?"
Comfort zone explosion. "I could scale but I'm nervous. Where am I playing small because I'm comfortable?" AI pushes you past safe.
What's the one thing you know you should be doing but keep putting off? Gary Vee would tell you to stop reading this and go do it right now.
Dive into our free AI Prompts Collection, packed with categorized mega-prompts and real-world test examples.