Money Tales
Money Tales
Aspiriant
Guiding Others and Finding Direction, with Caroline Gaynor
39 minutes Posted May 28, 2026 at 7:09 am.
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What happens when you realize the moments you feel most lost are the ones that end up giving you direction? In this episode of Money Tales, Caroline Gaynor, an endurance athlete who guides blind and visually impaired competitors through marathons and Ironmans, shares how helping others quite literally shaped her own path. From feeling unprepared for adulthood and money in her 20s to becoming a passionate advocate for financial education, Caroline’s story is honest and energizing.

Caroline is a vice president, relationship director and investment specialist at Avantis Investors®. Prior to joining Avantis Investors, Caroline served as a regional director at Dimensional Fund Advisors (DFA). Caroline is also a sought-after public speaker who has presented at numerous events and conferences for end-investor and advisor audiences. She received her B.A. from Columbia University.

Here are three money conversations this episode will help you navigate:

  1. The gap between confidence and financial reality in your early career
  2. How to think about investing before it feels urgent
  3. Navigating money dynamics in modern relationships

Follow Money Tales on Spotify, Apple Podcasts or YouTube Music for more real stories that inspire thoughtful, intentional decisions about money.