In this episode of Self-Directed, Mitchell sits down with real estate investor Kyle O’Hehir to discuss unconventional ways to break into the high-octane world of finance.


Kyle studied math at a state school before hustling his way onto Wall Street. He started investing in real estate on the side and went full time in 2018. Today he splits time between adding to his 300 unit affordable housing portfolio, growing his $10mm/month private lending business, and angel investing.


In this episode:

How to embark on a non-linear career journey
The benefits of becoming comfortable with rejection
Learning from failures and developing resolve
The “under-promise and over-deliver” strategy
When and how to sharpen your career growth plan from general to specific
How to evaluate advice
How to prove that you’re worthy of specific, next-level advice
The risks and rewards of entrepreneurship in the finance space vs. working for an institution

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