Insights in Hindsight is a bi-monthly series where operators share hard-won lessons, candid insights, and practical strategies for navigating growth. Each session brings together leaders who’ve been in the trenches to reflect on what worked, what didn’t, and what they’d do differently, creating space for honest dialogue and actionable takeaways.

Insights in Hindsight

This series is presented in partnership with the Operators Guild, an exclusive membership community of over 1,100 senior leaders in operations, finance, and business strategy across 20 global chapters. OG empowers leaders to scale with confidence by connecting them through a trusted peer network, investing together through its operator-led syndicate, and hiring through Guild Talent. Its members and advisors are the builders and scalers behind some of the tech industry’s most impactful companies including OpenAI, Slack, and Salesforce.

Interested in joining their membership? Learn more and apply at the Operators Guild.

“Serial Entrepreneurs”

September 24, 2025 | IMA Offices, Bellevue | 5–7 pm

What do seasoned entrepreneurs do differently the second — or third — time around? Hear candid stories of what worked, what didn’t, and the lessons they wish they’d known earlier. From team dynamics to performance management, attendees will leave with practical takeaways and peer connections. 

Featured Speakers: Nigel Sharp and Scott Nagel