Jan 18, 2021 · 33m · we-live-to-build
The Roles You Played at Home Are Killing You at Work
gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
Serial entrepreneur Jason Todd joins host Sean Weisbrot on the 'We Live to Build' podcast to discuss how childhood behavioral conditioning shapes workplace conflict, sharing insights from his journey building multi-million dollar ventures and advising founders.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Sean holds 29.3% of the talking time here. How this is scored →
speaking balance: gold is Sean, purple is the guest (3 minute bins)
When Sean asks what unasked question Jason wishes he would pose, Jason playfully shuts down the line of questioning with 'Nothing. Don\'t ask me more questions.'
Hardest push from Sean ▶ 27:02 Challenging the advisory pathSean pushes Jason on his career shift, pressing him on why he chose to advise others instead of building another venture of his own.
Biggest teaching moment ▶ 24:27 Family dynamics in the workplaceJason provides an in-depth conceptual breakdown of how unaddressed childhood family archetypes are unconsciously replicated in office hierarchies.
Sean holds their own ▶ 31:59 Psychological hiring criteriaSean asserts his own interviewing methodology and psychological assessment expertise by explaining how he screens candidates on self-love.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Sean as informed peer | Guest teaching | Guest disagreement | Sean pushing back | Why |
|---|---|---|---|---|---|---|
| Jason Todd and the 'Coffee with Humans' Experience | 3 | 1 | 1 | 1 | The conversation is friendly and collaborative as both discuss how they met via Audrey and their early programming/IT backgrounds. Sean contrasts his own customer-facing strengths in his father's dental office with Jason's phone customer service misadventures. | |
| Launching Alpine Home Air and Embracing Constructive Conflict | 3 | 3 | 1 | 1 | Jason recounts founding Alpine Home Air and learning to embrace heated disagreements rather than retreating. Sean brings up his psychology background to reinforce the importance of understanding interpersonal dynamics. | |
| Childhood Origins of Conflict Avoidance and Workplace Roles | 4 | 4 | 1 | 1 | Jason explores his childhood tendency to hide from anger and cites the book 'Don\'t Take It to Work' regarding how family dynamics manifest in executive leadership. Sean shares how his healthy upbringing gave him high emotional intelligence in business. | |
| Transitioning from Company Operator to Business Advisor | 2 | 2 | 1 | 2 | Sean probes why Jason decided to consult rather than build another company, prompting Jason to candidly admit to creator hubris and the mistake of making products before validating market demand. | |
| Practicing Self-Kindness and Finding Joy in the Journey | 3 | 1 | 2 | 1 | Jason jokingly pushes back when asked what else should be discussed, then shares his core philosophy of self-compassion. Sean validates this by sharing how he asks job candidates whether they love themselves. |