Jonathan Jackson

1/2 of the Dilly.

Location NYC

Number of Articles 45

Socials

Jonathan Jackson's Work 45 Articles

Free Agency - Jul 21, 2025 Want to understand an industry? Study who represents it.

Athletes have agents. Industries have associations.

by Jonathan Jackson

Free Agency - Jul 15, 2025 The New Starting 5: Small Teams in the Age of AI

The changing of the guard is here and now.

by Jonathan Jackson

Free Agency - Jul 07, 2025 Cayman for Creators: How South Africa Could Shake Up the Global Creative Economy

The law might play catch-up, but it is undefeated in forcing people to adapt.

by Jonathan Jackson

Free Agency - Jun 30, 2025 Free Agency 📈 - High Signal Brief

A speed run of some of the biggest things I've noticed in 2025 (so far).

by Jonathan Jackson

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 09, 2025 The Lion, The Wine, and the Yacht: How Cannes Makes a Killing on Creativity

Awards are a business unto themselves.

by Jonathan Jackson

Free Agency - Jun 02, 2025 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.

Sometimes, you just have to play through it.

by Jonathan Jackson