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About
Rule Breaker starts from a list of expectations its own site calls impossible: excel at work like you don't have kids, parent like you don't have a career, stay balanced like you're superhuman. Weisz's account is first-person — she followed the rules, hit her limit despite the colour-coded calendars, and concluded the rulebook was broken rather than she was. What she sells now is the rewrite: a playbook, a newsletter, and speaking and teaching aimed at working parents who want boundaries that would have horrified their former selves, and the same compassion for themselves that they give their kids. Weisz was COO of the Toronto one-on-ones software company SoapBox from 2013 to 2019, co-founded the Canadian arm of the leadership network Boma Global, and has been a venture partner at StandUp Ventures.
Backers
Not applicable — an independent practice, not a funded company.
Quick answers
What is Rule Breaker?
Jessica Weisz's practice for working parents — a playbook, a teaching program, a newsletter and speaking, built on the argument that the standards set for working parents are impossible by construction and are what should change.
Who runs it?
Jessica Weisz. She was COO of SoapBox, the Toronto startup whose software helped managers run better one-on-ones, from 2013 to 2019, co-founded the Canadian arm of the leadership network Boma Global, and served as a venture partner at StandUp Ventures.
When was it founded?
Not published. The site carries a 2025 copyright but states no founding date, so none is claimed here.