E918: Stack Overflow CEO & co-founder Joel Spolsky shares lessons growing his groundbreaking Q&A site to 100m+ monthly visitors, insights on leading, pivoting, selling Trello, engaging with VCs, becoming focused & what he’s looking for in his replacement as CEO

watch

listen

about this episode

Stack Overflow CEO & co-founder Joel Spolsky shares lessons growing his groundbreaking Q&A site to 100m+ monthly visitors, insights on leading, pivoting, selling Trello, engaging with VCs, becoming focused & what he’s looking for in his replacement as CEO

Show notes:

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.

more episodes