Editorial Note:
This story comes from our Co-founder Bernie Richter’s early lending days. We’ve updated it to highlight a timeless lesson: real estate can be a powerful wealth-building tool — but for most investors, it works best when it supplements, not replaces, the stability of a career.
Most of our rehab clients have a steady job with real benefits. They flip one house at a time because they enjoy the work — and they make money doing it. Many have successfully rehabbed one property at a time for over a decade, a few for two decades. Occasionally someone takes on two projects at once. Very few go beyond that.
That’s why the advice we often give is simple: don’t quit your day job.
But every rule has its exceptions. Years ago, Bernie financed a project for a young engineer named Don Julian. He started by building one home for himself. Then he built another to sell. Then another. Over time, he left engineering behind and launched what became one of the largest homebuilding companies in Kansas City, with over 2,000 homes built totaling more than a billion dollars.
His story proves that sometimes, the leap works out. But most of the time, smart investors keep their financial foundation — both personally and professionally — while building their portfolio step by step.
So, When Should You Not Quit Your Day Job?
For most investors, real estate should start as a side path to building wealth. Ask yourself these questions before considering whether you’re ready to go full-time:
- Do I have reliable income and benefits outside real estate?
A W-2 job not only provides steady cash flow but also makes financing easier — lenders see you as lower risk. - Have I proven success across multiple deals?
One or two successful flips are a good start. But it usually takes 10+ well-managed projects to establish a track record strong enough to scale. - Do I have systems in place?
Full-time investing requires more than passion. You need processes for acquisitions, contractors, financing, and selling. - Am I financially prepared for the dry spells?
Markets shift. Even experienced investors can face months without a profitable exit. Having savings and a safety net is essential.
The North Oak Approach
At North Oak, we encourage new and experienced investors alike to balance ambition with sustainability. Real estate investing is about freedom — but freedom is best built on a solid foundation.
Want to start investing without risking your financial stability? Let’s talk about how to structure your next deal so it fits your life today and supports your future freedom. Fill out a loan app or call us today.
