In this episode, John Harbison, veteran angel investor and longtime member of Tech Coast Angels, joins Shubha K. Chakravarthy to deliver a masterclass on how investors actually think about risk, founders, and funding decisions. Drawing on decades of experience as a founder, board member, and investor, John breaks down why every startup carries multiple dimensions of risk—and why the winners are those who score, prioritize, and actively mitigate them rather than deny them.

Check out his hard-won insights on:

The 30-minute scoring exercise that quietly predicts which startups won’t survive
Why a company with “balanced” risk can be more dangerous than one with obvious red flags
The founder response that instantly shifts an investor from skeptical to interested
The one signal that collapses multiple risk categories at once
Why “we have no competitors” is worse than you think
The subtle way founders lose credibility during competitive analysis
The coachability test founders don’t realize they’re taking in every meeting
The board dynamic that multiplies outcomes — and the one that destroys them
The winning company that only worked because they abandoned their original pitch early
The difference between pivoting wisely and panicking after one data point
The personality trait that saved six doomed companies — and killed six others
The financing contingency one experienced CEO refused to build — and what happened next
Why you don’t need most of the room to believe in you (and why that changes how you should pitch)

and much more!