Curious as Hell S01E03: No Grade 11. 170 Investor No's. The Decisions That Built the Company cover art

Curious as Hell S01E03: No Grade 11. 170 Investor No's. The Decisions That Built the Company

Curious as Hell S01E03: No Grade 11. 170 Investor No's. The Decisions That Built the Company

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Nobody would hire her. So she listed herself on Kijiji for $22/hour and built a company from that. Nine years later, she was signing exit papers, and she could not tell a single person it was happening, not even her wife. This is the version of that story she could not tell while it was happening.Bobbie Racette founded Virtual Gurus in 2016 after being turned down for every job she applied for as a queer, Indigenous woman in tech. She built it from a Kijiji posting with no grade 11 education and no playbook, through 170 investor rejections, into a VC-backed company she exited nine years later. She is now the chair of Queer Tech and the Indigenous Prosperity Foundation, and is building Tapwi, a FinTech platform for underserved founders named after the Cree word for truth.This conversation does not tell the version of the story that looks good on LinkedIn. It goes into the cost of hiding your identity, the people-pleasing trap that stalls real growth, and what it actually takes to process an exit when you cannot talk about it with anyone.Key themes from this episode:On the risk of certainty: Bobbie admits she was so fixed on where the business was going that she almost missed where it was actually heading. Certainty without curiosity nearly cost her the company.The moment she stopped hiding: A young trans woman showed up at her three-person office after hearing Bobbie on the radio and said she had saved her life. That was the day Bobbie decided to tell her story fully, every time, and everything changed.Building a culture around story: The employees who joined in the final three years of Virtual Gurus were not there for the paycheck. They were there because they had a story, and they felt it was the place where their story would be accepted.The people-pleasing trap: "I tried to make everybody happy versus understand the risks that needed to go. And I think that's where mistakes happen." It was not until Bobbie stopped trying to bring everyone along that the real growth started.Choosing to learn from the exit: She blamed the board, she blamed the new CEO, and then she chose differently. "I could choose to learn, or I could choose to really hate this. And I chose to learn from it."Tapwi and what comes next: Tapwi means truth in Cree. It is a FinTech-style platform for underserved founders, built to give them the resources and honest information Bobbie did not have when she started.Chapters:0:00 — Welcome and Bobbie's story0:50 — "I started Virtual Gurus because nobody would give me a job."1:16 — Queer Tech and the Indigenous Prosperity Foundation2:52 — The financial literacy board game and Walk Together program4:53 — The risk of certainty in the early founder days6:13 — Learning from mistakes before they go too far7:30 — Blind ignorance and brute force: what early founders actually need9:21 — The pivotal realization: the company only grows as much as you do9:49 — The 170 nos and why she stopped hiding her identity11:28 — The radio show, the trans woman, and the moment everything changed13:33 — Building a culture around authenticity and story15:28 — Psychological safety at scale: what leaders carry16:37 — The people-pleasing trap and when growth actually started19:34 — Passing the baton: knowing when it is time to go21:24 — From throwing spaghetti to calculated risks23:46 — What success really looks like versus how it looks on social media25:58 — The dual track: raise or sell, stepping into a president role28:25 — The hardest part of the exit: not being able to tell the team29:47 — Blaming the board, then choosing to learn instead31:07 — Self-help books, ceremony, and digging deeper33:17 — The last eight months: the hardest period34:23 — Money as trauma in the Indigenous world37:14 — The bias leaders carry: the belief that you're always right38:13 — Coaching vs. correcting: helping people shine41:42 — Leading up and leading down: the hardest leadership challenge45:16 — Knowing when you're no longer the right fit47:00 — The journey of self and losing the passion48:10 — Non-negotiables for the next venture50:28 — Boundaries: learning to say no52:23 — Not a victim: owning the exit completely53:36 — Tapwi: truth in Cree, and what she's building next56:11 — The book and the documentary58:29 — What Bobbie is most curious about nowConnect with Bobbie: linkedin.com/in/bobbiejoracetteLearn more about what we do at clearmotive.ca If this conversation was worth your time, subscribe wherever you listen and leave a review. It takes two minutes, and it helps more people find the show. ★ Support this podcast ★
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