In this episode of The Lobster Talks, we’re joined by Wayne Crosby, a true startup veteran with a remarkable full-circle journey:

• 2007: Wayne became a Y Combinator founder in one of the earliest cohorts, quickly landing a Google acquisition that evolved into Google Slides.

• A Decade at Google: He stayed on to help grow G Suite, diving into AI and shaping how millions of users collaborate online.

• Startup #2 & Another Exit: After co-founding a second company with Google’s former CHRO, he returned to YC as a Visiting Group Partner to coach a new generation of founders.

• Today: Wayne is back to building as founder/CEO of Orgorg.com, a toolset for seamless team management and productivity, integrating AI under the hood.

We talk early YC days, Google’s culture of innovation, what it’s really like behind the scenes as a YC Partner, and why Wayne ultimately returned to his roots as a builder. If you’re curious about AI’s impact on future jobs, or just want insider knowledge on startup growth, this is a must-listen.

Key Discussion Points

• The magic (and myths) of the very first YC cohorts

• Lessons from building Google Slides and leading teams inside Big Tech

• Why AI is more than just a buzzword—and how Wayne is weaving it into Orgorg.com

• Life as a YC Visiting Group Partner—what founders should really know

• Embracing your inner builder: how Wayne found his true passion in startup creation

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Timestamps

0:00 Welcome & Wayne’s Background

4:17 Early YC Days (2007)

9:32 Google Acquisition & Lessons Learned

14:45 AI at Google & Future of Work

22:10 From Founder to Visiting YC Group Partner

28:55 Building Orgorg.com & Founder Insights

38:16 Balancing Family & Startup Life

43:00 Advice for Aspiring Entrepreneurs

Thanks for tuning in to The Lobster Talks!