After five companies. After launching Canada's first incubator for justice-impacted entrepreneurs. After helping 140+ formerly incarcerated people build their own businesses.
Someone looked at Lucy Cullen and said she didn't look like she should be doing that.
She looked back at them and kept going anyway.
Lucy Cullen is a five-time founder, executive coach, and the co-founder of Comeback Catalyst, Canada's first incubator supporting entrepreneurs who have been through the justice system. In this conversation, she and George unpack what it means to build a business the world isn't ready for, what formerly incarcerated entrepreneurs have taught her about resilience, and why unconditional positive regard might be the most underused leadership skill you have.
What You’ll Learn In This Episode:
Key Takeaways:
✔️You do not have to look a certain way to take on the hardest problems in the world. But most rooms will expect you to. How you respond to that moment defines the kind of leader you are.
✔️Systematic change does not come from one person doing the right thing on their shift. It comes from building something that works when you are not in the room.
✔️Justice-impacted entrepreneurs face barriers that would stop most people before the starting line. The ones who push through have a level of resilience that redefines what is possible.
✔️Unconditional positive regard is not a soft skill. It is an organizational operating principle. Adopt it from day one and it changes how your entire team shows up, inside work and outside it.
✔️Everyone is doing the best they can with what they have. They deserve to be seen that way.
✔️The businesses that matter most are often the ones the world says are not ready for yet. Build them anyway.
Timestamps & Highlights:
[00:00] — Someone said she didn't look like she should be doing this. She kept going anyway.
[01:30] — Welcome: five companies, two missions, one very clear north star
[03:45] — From environmental studies to entrepreneurship: the origin story
[06:07] — The food waste problem that launched everything
[15:00] — What is Comeback Catalyst and who does it serve
[22:00] — What justice-impacted entrepreneurs have taught Lucy about resilience
[33:00] — Keeping going when the room doubts your right to be in it
[44:00] — Lumen Onyx and the executive coaching work
[52:00] — Unconditional positive regard as an organizational operating principle
[58:21] — How it changed the team from day one
[1:00:13] — The homework: practice it once today
[1:01:48] — How to support Comeback Catalyst
Connect with Lucy Cullen
She is the Co-Founder and CEO of Comeback Catalyst, Canada's first incubator for justice-impacted entrepreneurs, and Founder of Lumen Onyx, a leadership advisory and executive coaching firm. She is a five-time founder, valedictorian of the Rotman School of Management Executive Coaching program, and one of Canada's Top 30 Under 30 Sustainability Leaders.
Instagram: @thelucycullen
Website: combatcatalyst.ca
Email: hello@combatcatalyst.ca
Your Challenge This Week:
Two things today. If this landed, reach out to Lucy.
Email hello@combatcatalyst.ca or find her on Instagram.
And at least once today, practice unconditional positive regard with one person. That is the whole assignment.
Follow George: @itsgeorgebryant
Work with George:
The Alliance — Community for entrepreneurs building businesses that matter.
1:1 Coaching — Limited spots. Apply at mindofgeorge.com/coaching-consulting/
Live Retreats — In-person experiences for entrepreneurs ready to go all in on the work that matters.