Stack Overflow Joel Spolsky: 100m+ mo visitors, leadership, pivots, Trello sale, stepping aside | E918

Jason Calacanis interviews Joel Spolsky, discussing the sale of Trello to Atlassian, founding Stack Overflow, and Union Square Ventures. They explore anti-VC rhetoric, the Q&A space, and lessons learned in leadership. The episode also features an audience Q&A session.

Speakers

AI Chat

Unidentified

Jason Calacanis

Host • 34%

Joel Spolsky

Guest • 62%

Unidentified

Chapters

0:00	Opening
0:51	Jason introduces Joel Spolsky. Joel talks about why he sold Trello to Atlassian, founding Stack Overflow, and Union Square Ventures.
9:20	Jason thanks sponsor Segment. To see if you or a startup you know qualifies, check out segment.com/twist.
11:33	Anti-VC rhetoric and the power dynamic between investors and entrepreneurs.
17:07	Conversation around the Q&A space: missteps/triangulation that made Stack Overflow what it is today, why so many companies in the Q&A space got it wrong, the messy middle for Stack Overflow.
28:40	Jason thanks sponsor LinkedIn. Redeem your first free $100 ad credit by visiting linkedin.com/thisweekinstartups.
30:58	Joel talks about what Stack Overflow would become if he didn’t have control over the board, and Glitch vs. Git.
35:45	Lessons learned from the “second act” and leadership, and looking for a new CEO.
43:55	Jason thanks sponsor Capterra. Visit capterra.com/twist to find the right business software for you.
45:48	Audience Q&A: Explaining to investors the benefits of a past pivot, Joel’s future plans, and tactical skills that made a big impact.

Transcript

Clip

Loading transcript...