Saying Yes Before You’re Ready, Creating Community, and Lessons from Shark Tank with Megan Reilly
- mgraziano45
- Apr 28
- 3 min read
In this episode of Adventures in Business, Amani and Mandi chat with a real firecracker – Megan Reilly, a professional speaker, top 12 podcast host, and President of Events & Coaching for Jesse Itzler's 100 Mile Group. Megan shares her inspiring story of realizing her own value, how she cultivates a durable community, and the lessons she learned from being on Shark Tank (and getting an offer from Mark Cuban!).
Meet Megan Reilly
Megan Reilly’s path has been anything but linear – from walking on a D1 basketball team, to building a multi-million dollar company, to creating a chart topping podcast, to developing a powerful network with the biggest names in business – Megan walks the walk and loves sharing all the gritty details with audiences around the world.
When Megan became a mom her perspective changed forever and for the best. After years of running her company and raising three daughters Megan was ready to build her personal brand with plans and hopes of supporting working parents, women, moms. She created the concept of Who is Your Momma Podcast and through her work she met Jesse Itzler.
Her podcast gained momentum and Jesse asked Megan to be a part of various projects he was running including being a daily radio host discussing business and family and later he invited her to be a mentor in his Elite Mastermind group along with world-renowned experts handpicked by Jesse. She continues to work with Jesse today as Director of Members for Adventure Club.
Today, Megan ignites audiences as she authentically shares her journey and lessons.
Megan’s Story: Never Disqualify Yourself
Before the keynote speeches and building a franchise to 70 locations, Megan Reilly was a college freshman who walked on the University of Oklahoma’s basketball team. It was a stacked roster filled with elite athletes – and Megan saw everything she wasn’t.
She wasn’t the fastest or the strongest, and she didn’t feel like she belonged. So she quit.
And then? That same team went on to the national championship. Megan watched it all unfold – from her couch. That moment became a defining chapter in her life – what she now calls “Megan on the couch.”
She realized that she didn’t need to be the star player to contribute to the team’s culture, to be a positive force in the locker room, or to show up and work hard. Now, when something feels big, she doesn’t walk away; she leans in.
Designing Events That Matter
Mandi shares her experience attending one of Megan’s events, and it’s clear this isn’t your typical conference. From start to finish, the experience at Megan’s events is intentional, thoughtful, and deeply impactful.
Megan’s secrets are these:
Obsess over value
Curate diverse, complementary voices
Build experiences, not just schedules
It’s like a puzzle. Every speaker, every moment, every interaction needs to fit together in a way that creates something bigger than the sum of its parts.
Building a Durable Community
Megan emphasizes that the real power lies in the community that continues long after the event wraps. It’s about making people feel like they’re part of something and empowering them to take ownership of the community.
So how does she create a durable community between events? Megan doesn’t rely on rigid formulas.
Instead, she focuses on:
Staying true to the community’s purpose
Adding value consistently (especially during lulls)
Creating space for members to lead and engage
Facilitating (not controlling) the conversation
On top of all of this, she’s slow with people. In a world where we are rushing from one thing to the next, Megan makes a point to make eye contact, remember details, and create connections that keep people coming back.
Megan Reilly on Shark Tank
Megan didn’t submit her own name for Shark Tank – her brother-in-law did. She decided it was worth the risk (because, as she shared, you become qualified through action – so calculated risk is just a part of that).
And so when she was standing in front of the Sharks, she knew there was a lot she couldn’t control – like how the show was edited or if the Sharks liked her. But what she could control was how prepared she was. She studied the Sharks – their backgrounds, their interests, even their families – and walked away with an offer from Mark Cuban.
In the end, the deal didn’t work out (she wanted to expand their brand, which wasn’t part of the offer). But the experience was important for Megan to get to where she is today.
Resources Mentioned
🔗 Learn more about Jesse Itzler’s events
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