Rebounding from His “Worst Financial Decision” to Quit at 38

Episode #557

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Have you ever made a poor financial decision? You’re not alone! But can a bad blunder disqualify you from FIRE? Today’s guest made a huge investment at the worst possible time, a move that had consequences a decade later. Despite this, he was still able to reach early retirement in just fifteen years!

Welcome back to the “BiggerPockets Money” podcast! Ryan Connell had a picture-perfect start to his financial independence journey—saving money at a young age and living well below his means. But then 2007 arrived, and Ryan made the “worst financial decision” of his life. He bought a house just weeks before the housing market began its historic collapse. But a move that could have derailed his quest for FIRE proved to be a minor setback because Ryan was still able to retire at the age of thirty-eight!

In this episode, you’ll learn why you should treat real estate as less of a “sure thing” and more like the stock market. Ryan discusses his current portfolio, which consists of 100% index funds, and what led him to pivot from real estate investing entirely. He even gives us a peek into the average day as an early retiree and shares why he has never had a FIRE number!


00:00 Intro
02:02 Buying a House...in 2007
09:42 Digging His Way Out
18:46 Ryan’s Journey to FIRE
28:25 Saving TOO Much?
35:00 Life After Early Retirement
40:49 Find Freedom Faster!