How does a traumatic brain injury turn into a founder mindset? In this episode of the Bizz Bitch Podcast, host Jazmin Cornejo talks with Rylie Jennings, founder of Outspoken Management Group, about surviving a life-altering accident at 17, building a career through strategic volunteering, and why she recently stepped away from an executive role to build her own brand full time.
Rylie shares the full story of the car accident that left her with a fractured skull and brain bleed, how that experience became the foundation of her "live now, not later" philosophy, and the winding path from a shelved health tech startup to running experiential events for organizations across the country.
Key talking points:
- The volunteering strategy that gave Rylie access to rooms she couldn't afford to enter
- Her traumatic brain injury at 17 and how it reshaped her risk tolerance
- Building a TBI survivor support startup as a college freshman, and why she shelved it
- Why she left her Chief Programs Officer role at Stella to build Outspoken
- Setting boundaries and charging appropriately as a service-based entrepreneur
Timestamps
0:00 - Intro and how Jazmin and Rylie actually met
2:07 - Who is Rylie: founding Outspoken Management Group
3:06 - Trusting gut instinct as an entrepreneur
7:17 - The volunteering "cheat code" for getting into any room
7:38 - Becoming the connector and curator
12:06 - Why weddings aren't Rylie's lane
13:01 - Growing up in a big Polynesian family
16:33 - Lessons from entrepreneurial parents
20:29 - The car accident and traumatic brain injury
24:56 - Turning trauma into a "live fully now" mindset
29:12 - Building and shelving a TBI support startup
34:08 - From Baddies Mean Business to Outspoken
38:56 - Stepping away from Stella as Chief Programs Officer
41:52 - The vision for Outspoken's future
44:00 - Money, worth, and charging for your time
44:28 - Advice to her younger self
45:15 - Where to find Rylie and closing thoughts
(Timestamps are approximate based on the recorded conversation and may need adjusting to final edit.)
Guest Links
Rylie Jennings – LinkedIn / Outspoken Management Group
Website: sooutspoken.com
Sponsors / Affiliate Links
HoneyBook: https://share.honeybook.com/jmcbizzsupport
Granola.ai: https://join.granola.ai/t/gj8nuwvchd
Rakuten: www.rakuten.com/r/JAZMIN13048
If this episode hit different, subscribe so you never miss one, leave a review to help more people find the show, and share this with a mate who needs the reminder that trauma doesn't have to be the end of the story.
🎧 Stay Plugged In with Jazmin & the Bizz Bitch Crew:
📱 Let's be Insta besties:
@jazminmcornejo — raw biz truth, CEO vibes, and luxury lifestyle
@bizzbitchcommunity — for women building bold, unapologetic empires together
💎 Become a Bizz Bitch Member:
Tap into exclusive content, mentorship, and premium support:
jazmincornejo.com/bizz-bitch-membership
🎙️ Interested in being a guest?
DM me with your story, your spice, and what you're bringing to the mic.
Loved this ep? Leave a review + tag me on IG!