Jonathan Courtney is the co-founder of AJ&Smart, the Berlin agency that helped make the Design Sprint famous and trained thousands of facilitators through Workshopper and facilitator.com. 

In September 2026, after 16 years, he handed the company to his team and announced he was leaving to become a musician. We recorded this three weeks into that decision. 

Chapters
0:07 What entrepreneurship really means to Jonathan
2:14 Why money is just a scoreboard
4:33 Leaving his business after 16 years 
7:03 Buying a piano and a 12-hour first session
12:23 The Saturday that changed everything
16:51 "Do it on the side": the comment that made him defiant
19:38 What kept him from creative work for 15 years
25:56 The doubts: money, status and identity
32:21 Why "stuck" people don't really want it
34:45 "Next year" means never: the power of urgency
39:32 Sharing unfinished work
43:39 Accepting that people will laugh at you
48:54 The "What You Already Know" workshop
56:14 Why he waits for permission
01:06:27 The promoter mindset: business lessons for musicians

Jonathan is still finalising the "What You Already Know" workshop. Sign up at alen.me and you'll get the questions as soon as they're ready.

Entrepreneurial success has less to do with strategy than we like to admit. Two founders can have the same idea, the same market and the same money, and one wins because of what is going on between their ears. Yet almost every podcast interviews founders about The How. This one interviews them about The Who. 

Each episode a founder lies on the couch and we go into the mindset, the pressure, the stories they tell themselves and the ones they hide. Hosted by Alen Faljic, founder of d.MBA. Follow the show and catch episode one when it drops.