Episode 432: Creating a Future of Flexibility & Financial Security with Jackie Kasper

Jun 25, 2025

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This week on the Journey to Launch podcast, I’m joined by Jackie Kasper, a fellow Journeyer who’s intentionally building a life of connection and financial freedom. Jackie is a mom of two, a director of operations at a Chicago-based fintech startup, and someone who's actively pursuing Financial Independence (FI) within the next 2–7 years.

We also dive into how she and her husband are navigating the journey together (even if they’re not always on the same financial page), the influence of motherhood on her long-term goals, and what reaching Coast FI means for her family’s options and freedom.

In this episode, Jackie opens up about:

How she got into the FI movement after being introduced by her sister-in-law
The mindset and financial shifts she made to go from spending freely to strategically investing
Buying her first multi-unit property with her brother at 25 and how real estate plays into her FI goals + much more.0