Kirupa is a Senior Director of Product Management at Salesforce. Previously he was at Microsoft for over a decade as a technical PM, where he worked on the Developer Division and Windows teams. He has a Computer Science degree from MIT. On the side, Kirupa is a prolific creator. He's built one of the Internet's top free resources on web development (kirupa.com), published 8 technical books, runs a Youtube videos with well over a million views, and presented at many conferences.

Here are some relevant links from the conversation:
kirupa.com

Doom, Quake, and Wolfenstein 3D video games
Pixel art
Kirupa's Youtube channel

Kirupa's books on web development
Microsoft Silverlight
Show notes:
2:12 IDDQD cheat code
3:03 An explanation of Product Management
4:27 Skills Kirupa looks for when hiring PMs
5:12 Solutions sometimes provided by a technical customer base
6:40 Why MIT?
7:51 Online personality = Offline personality
8:54 Working at large tech companies
10:54 Working on Silverlight tools
12:05 A love for pixel art
13:37 Gray areas of fields like design and development
15:54 Staring kirupa.com
19:31 Juggling a full-time career with side projects
20:39 Youtube videos
21:30 Kirupa's cat: a regular attendee at work meetings
22:25 Deciding what to invest time in
23:36 How working from home has changed things
24:58 Walking meetings
25:17 Influential people in Kirupa's life
26:37 The role of luck
28:36 Would any of this have been a surprise?
31:02 An 80th birthday toast
32:25 Ask for help early, ask for help often