#122 President & Board Member at Freshworks, Dennis Woodside: What If This Goes Really Well?

Guest: Dennis Woodside, President and Board Member at Freshworks In this episode, we cover: Google’s acquisition of Motorola and how Dennis went from ad exec to first-time CEO (02:00); Did Dennis like being the CEO of Motorola? (08:04); The stress of the new job and dealing with it through exercise (13:02); Dennis’ impressive résumé and what dinner conversation was like growing up (18:37); Going to Korea and choosing the harder path (23:00); Joining Google in 2003 as a general problem-solver (26:23); Hiring “scouts” all around the world to better understand the internet (30:41); Leaving Motorola to mentor Dropbox CEO Drew Houston (39:12); Checking your ego and the listening tour that wasn’t (42:20); Dropbox’s IPO and why the stock has been relatively flat (48:38); Changing jobs without breaks, and spotting new opportunities like Freshworks (52:19); Tips for working with founders and interrogating the status quo (58:02); Dennis’ most unique OKR at Dropbox (01:02:39)