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Jonathan Jackson

1/2 of the Dilly.

Location NYC
Number of Articles 41
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Jonathan Jackson's Work 41 Articles
Free Agency   -   Jun 17, 2025 Deal or No Deal: How a creator takes investment, and what it means

Much has been made about the future of what creator economy is, could be, and is turning into. So here’s a real deal, with an actual person, and what the thesis was. Hopefully the gives a tangible example of both how a business is being built, and why an

by Jonathan Jackson
Free Agency   -   Jun 02, 2025 Pricing is a game. It should be treated that way.
Pricing is a game. It should be treated that way.

Playing not to lose, is not playing to win. Pick your hard.

by Jonathan Jackson
May 20, 2025 Some thoughts on writing, thinking, and building.
Some thoughts on writing, thinking, and building.

Sometimes, you just have to play through it.

by Jonathan Jackson
Free Agency   -   May 13, 2025 Free Agency Vol. 35 - Real Yearners Only
Free Agency  Vol. 35 -  Real Yearners Only

Community is what people want and need. So why is everyone afraid to care?

by Jonathan Jackson
Free Agency   -   Apr 28, 2025 Ryan’s World: Obsession, Deep Collaboration, and Deal Terms
Ryan’s World: Obsession, Deep Collaboration, and Deal Terms

Coogler is unprecedented. His deal is not.

by Jonathan Jackson
Free Agency   -   Apr 15, 2025 The Vibecast is Here to Stay
The Vibecast is Here to Stay

Can you feel it in the feed?

by Jonathan Jackson
Free Agency   -   Apr 07, 2025 Free Agency - Lessons from the Slutty Vegan Restructuring
Free Agency  - Lessons from the Slutty Vegan Restructuring

The money always comes with terms and conditions.

by Jonathan Jackson
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