Resilience isn’t built in moments of ease, it’s forged through challenge, curiosity, and the courage to grow.
In this episode, Heather Brilliant, CEO of Diamond Hill, shares how 38 rejection letters early in her career became the foundation for a life of resilience, curiosity, and courageous leadership. With experience spanning Bank of America, Morningstar, and now Diamond Hill, she reveals how staying open to feedback, to failure, and to change has fueled her growth as a leader and innovator in investment management.
Her journey from aspiring lawyer to CEO is a story of perseverance and adaptability, proving that leadership isn’t about following a straight path, it’s about learning, evolving, and leading with both humility and conviction.
Tune in to learn how resilience is built through feedback, why curiosity drives clarity, and what it means to lead with openness in a world that never stops changing.
Key Takeaways:
- The Curiosity Compass – How asking better questions unlocks your next opportunity.
- Feedback as a Gift – Why openness to input accelerates growth.
- Resilience in Motion – How adaptability builds confidence, credibility, and trust.
- Openness as Strength – Why listening deeply makes you a better leader.
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Highlights
The key moments in this episode are:
[00:00] Introduction to Beyond Barriers Podcast
[00:27] The Importance of Resilience and Rejection
[01:16] Heather Brilliant's Career Journey
[04:20] Networking and Career Growth
[08:02] Leadership and Personal Development
[17:24] About Diamond Hill and Heather's Role
[19:16] Daily Habits and Success Rituals
[17:24] Balancing Internal and External Focus
[19:16] Embracing AI in the Workplace
[20:22] Effective Decision-Making Strategies
[34:21] The Importance of Curiosity
[38:30] Lightning Round and Final Thoughts -
Lightning Round
Q: What book has greatly influenced you?
A: Fierce Conversations by Susan ScottQ: What is your favorite inspiring quote or saying?
A: Fight for the things that you care about, but do it in a way that will lead others to join you by Ruth Bader GinsburgQ: What is one word or moniker you would use to describe yourself?
A: OpenQ: What is one change you've implemented that made your life better?
A: Exercising at least four or five times a weekQ: What power song would you want playing as you walk out onto a stage?
A: Hit Me With Your Best Shot by Pat Benatar -
Quotes
It always looks like you have this smooth pathway, but the reality is that mine really started with a very challenging time of having to overcome quite a lot of rejection
Heather Brilliant
Everybody thinks that when they look at somebody’s résume, they’re seeing the whole story. But you’re only seeing the successes. Everyone has stuff on the cutting room floor
Heather Brilliant
I always encourage people to put their hands up for roles they’re interested in. You won’t get every role, but you gain resilience through the process
Heather Brilliant
Developing skill in something you enjoy gives you a powerful foundation for whatever you do later
Heather Brilliant
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About
Heather serves as Chief Executive Officer for Diamond Hill and joined the firm in 2019.
Heather brings more than 20 years of domestic and international investment industry experience to this role. Most recently, she served as chief executive officer, Americas with First State Investments. Prior to that role, she spent nearly 14 years with Morningstar where she served as global head of equity & credit research before advancing to chief executive officer, Morningstar Australasia.
Heather earned her MBA from the University of Chicago Booth School of Business and has a degree in economics from Northwestern University. She served on the board of the CFA Institute from 2013-2020 and was chair of the board in 2018-2019.