From Dorm Room to $1B+ Outcomes: The Decisions That Matter Most

​This event is part of 1871’s Behind the Builder Series  - a recurring conversation that goes beyond founder stories to unpack the real decisions, trade-offs, and systems that shape enduring companies.

​We will sit down with Bob Casey, Founder & CEO of Santa Barbara Management, in a fireside conversation hosted by Scott Holloway, Managing Partner at Starting Line. Drawing on Bob’s experience building and scaling companies, from an early Yale startup to leadership roles at Tegus, IGSB, and Santa Barbara Management, the discussion will focus on what actually helps companies win early, scale thoughtfully, and sustain value over time.

​This session centers on practical lessons founders can use today: how experienced operators and investors think about risk, focus, governance, and growth.

​Featured Speakers

• ​Bob Casey: Founder & CEO, Santa Barbara Management

• ​Scott Holloway (Host): Managing Partner, Starting Line

​Member Exclusive (5:00 PM – 5:30 PM)
A closed door founder session for 1871 members for unfiltered candidness and conversations with speakers before public session.

​Public Session (5:30 PM – 6:16 PM)

​Discussion Focus

• ​From first startup to breakout outcomes — the practical decisions, trade-offs, and “unsexy” choices that actually move the needle.

• ​Building in Chicago — what makes the ecosystem durable, and how founders should decide where to build.

• ​Concentration & systems — lessons from long-horizon investing on focus, risk, and what makes companies exceptional.

• ​Scaling with discipline — lessons from growing a company to $120M+ ARR, and how founders can scale without losing focus or quality.

​Happy Hour Networking (6:15 PM – 7:30 PM)

​Attendance is acceptance-based only. Request to attend. Priority acceptance for 1871 Members.