What if the most powerful thing a leader can do isn’t strategy, charisma, or authority — it’s the willingness to be truly seen?
In this episode of Rogue, Jeff Gibbard sits down with Bobby Umar — keynote speaker, 5x TEDx Speaker, and one of Inc. Magazine’s Top 100 Leadership Speakers in the world — to break down the superpower behind his entire career: Vulnerable Storytelling.
Bobby has delivered 1,000+ keynotes across four continents. His work has been built on a single belief: the most powerful thing a leader can do is make people feel seen. In this conversation, we dissect exactly how he does it so you can steal it.
Key Takeaways
– Vulnerable storytelling creates trust, deeper connection, and environments where others feel safe to open up – Intention is everything — share to help others, not to gain attention or likes; people can feel the difference – Three prerequisites must exist before anyone will be vulnerable: care, trust, and safety – Share scars, not wounds — only share experiences you’ve healed from, not what’s still raw – Vary your stories over time — repeating the same vulnerable moment turns authenticity into performance – The life story exercise: bullet-point your life (good, bad, ugly) to discover your values, personal brand, and the material that connects you to others
Timestamps
[00:02] Introduction
[01:03] Bobby’s superpower: Vulnerable Storytelling
[07:25] Why making people feel less alone is the whole point
[03:02] The dark side: when vulnerability becomes manipulation
[10:53] What must be in place before people will open up
[18:05] Bobby’s origin story and the epiphany moment on stage
[21:12] The life story exercise
[42:17] Share scars, not wounds
[33:13] Real-world applications (sales, coaching, parenting, speaking)
[31:59] The three-part framework: Intention, Method, Ownership
[37:40] Recap: how to steal this superpower
About Bobby Umar
Bobby Umar is a keynote speaker, executive coach, and one of the most recognized personal branding experts in North America. Inc. Magazine named him one of the Top 100 Leadership Speakers in the world — alongside Richard Branson, Brené Brown, and John C. Maxwell. He’s a 5x TEDx Speaker and 2x LinkedIn Top Voice whose work has reached audiences across four continents.
Over a 20-year career, Bobby has delivered more than 1,000 keynotes and workshops for leaders, entrepreneurs, and teams who want more than motivation — they want a real shift. His signature blend of vulnerable storytelling, heartfelt humour, and practical strategy doesn’t just engage a room. It changes how people see themselves.
Bobby is the founder of DYPB (Discover Your Personal Brand) and TLB Club, a thriving membership community for thought leaders and small business owners. He also coaches professionals to land TEDx talks that build lasting authority. With a background spanning brand marketing (Kraft & Unilever), engineering (Bombardier), and the performing arts (Second City), Bobby brings a rare combination of strategic depth, stage presence, and genuine humanity to every room he enters.
He’s based in Toronto. He’s a proud dad of two. And he’s built an entire career on one core belief: the most powerful thing a leader can do is make people feel seen.
Connect with Bobby
– Website: www.raeallan.com | http://www.dypb.ca | http://www.thoughtleadershipbranding.club
– Speaker website: https://www.nsb.com/speakers/bobby-umar/
– LinkedIn: https://www.linkedin.com/in/bobbyumar/
– Instagram: https://www.instagram.com/raehanbobby/
– YouTube: https://www.youtube.com/c/BobbyUmar
– Substack: https://substack.com/@bobbyumar
– Bluesky: https://bsky.app/profile/raehanbobby.bsky.social
Special Offer
Bobby is offering access to one of his private coaching calls from his TEDx Mastery Mastermind group and TLB Club membership community. Send him a DM to get a special invite.
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