NOTE: This interview was conducted in July 2025
00:55: Who is Tobi in this very moment?
1:27: On the decision to hold Black Ballad Weekender for a second year
2:54: The “from failure” origin story that started Black Ballad back in 2014 and the process of getting it off the ground — including a free-access model to start
8:10: Pivoting to a subscription model in 2017
10:39: The evolution of securing sponsorships and partnerships for Black Ballad — and that stand out moments (good and bad), plus the sometimes tokenizing process of seeking investment
24:21: The content and contributorship side of Black Ballad — and what releasing editorial operations taught Tobi about business and leadership
28:44: The value of building a personal brand
34:08: The importance of setting very firm boundaries — down to a very thorough email auto-response and rejecting low-ball offers.
