How to structure collaborations so both sides feel like they won

Executive overview

Most people approach collaborations trying to win the deal for themselves. The result is partnerships that feel transactional and often fail. The goal should be 50-50 intent — but with the maturity to accept that outcomes may land 73-27 in either direction.

The deal is won when both sides feel great about it, not when one side extracts more.

The 50-50 intent principle

• True collaboration starts with equal intent, not equal outcome
• Outcomes rarely split evenly — nuances, timing, and execution shift the balance
• A deal that lands 73-27 can still be a good collaboration if both sides genuinely tried
• Feeling good about a collab that didn't work out financially is a sign the intent was right

How to build a collaboration that works

• Make pretend you are fully the other person — what would they say yes to?
• Your goal is for them to feel it was the best decision they made
• Push for something genuinely new, not just a logo slap on an existing product
• Authenticity collapses when the collaboration feels forced or one-sided
• Most people fail because they come from a mindset of scarcity

The VeeFriends x Gregory's Coffee example

• VaynerMedia employees used Gregory's Coffee from the start — the relationship was organic
• Gary requested a new drink be created, not just branded packaging
• Gregory's connected with the collaboration because of shared values: positivity, hard work, entrepreneurship
• The Jolly Jacko pumpkin chai latte was the output — a product neither side could have made alone