What if your biggest investing setback wasn’t a market call that went wrong…
…but simply trusting the wrong system?
That’s the honest story Josh Wedding brought to the Not Your Average Investor Show last week. And it’s one of the most powerful stories we’ve shared in a long time, because it’s real, it’s raw, and it sounds a lot like where a lot of you are right now.
Let’s dig in.
The “Why” Born in the Oil Fields
Josh’s story is a masterclass in using “financial stress” as a catalyst for change.
At 20 years old, the pressure of living paycheck-to-paycheck convinced him that he never wanted a lack of money to prevent him from being the best version of himself as a husband and father.
- The Grind: Josh worked 90-hour weeks in the Texas oil fields, trading his physical and mental well-being for high pay.
- The Realization: He saw older colleagues in the industry who were physically broken after 20 years and realized he was working hard for money, but his money wasn’t working for him.
- The Pivot: He used high-risk, high-reward assets (like crypto mining and trading) to build a “pile of cash,” but he always had a pact with himself: once the money became “life-changing,” he would flip it into a stable base.
A Tale of Two Operators
Before finding a system that worked, Josh experienced the pitfalls of poor management.
👉 The Impact of Misaligned Values on Property Management
His first turnkey property in Ohio turned into a “constant headache” due to a lack of infrastructure and misaligned incentives with his property manager.
But after connecting with JWB, Josh was able to execute a high-growth strategy in Jacksonville. In just four years, Josh achieved:
His 4-Year Results (5 Properties):
| Metric | Result |
| Total Profit | $333,000 |
| Internal Rate of Return (IRR) | 16.3% |
| Acquisition Strategy | 5 properties in a single year (2022) |
| Projected Net Worth Growth | Refinancing to grow from $2M to $4M |
Josh then concentrated his investments in Jacksonville, not for the sake of diversification, but because he believed in the operator and the market.
Matching Strategy to Life Stage
Josh is a firm believer that “personal finance is personal”.
Because he still has active income and a long-term horizon, he chose a strategy that prioritizes equity growth over immediate monthly cash flow.
- The Refinance Decision: Josh recently refinanced his entire portfolio to pull equity for future acquisitions.
- Long-Term Math: His analysis showed that by “serial refinancing”, reinvesting equity every few years, he could potentially double his real estate net worth from $2M to $4M over 15 years.
- Legacy Over Income: For Josh, the goal isn’t $1,000 in monthly cash flow today; it’s building a machine that creates massive options for his future self.
👉 Personal Finance: Tailoring Real Estate Goals to Life Stage
This strategy only works because Josh is building for his specific reality, rather than following a generic script. If your active income already covers your bills, stop obsessing over the monthly “grocery money” and start focusing on the size of the legacy you’re leaving for your future self.
NOT YOUR AVERAGE INSIGHT: Regret Is a Better Compass Than Rates
👉 A Framework For Making Every Financial Decision With Clarity
The real shift in Josh’s life wasn’t just moving money from crypto to real estate; it was the move from working for money to building a system that works harder than he does.
Instead of chasing “perfect” market conditions, Josh got clear on his goals, which allowed him to make bold moves because he knew exactly how those moves served his 15-year legacy.
He chose to minimize future regret rather than obsess over pennies in the short term or interest rate spikes. Josh learned to frame every financial decision around the minimization of regret, asking himself which choice his “future self” would thank him for 15 years down the road.
True wealth is built by putting one foot in front of the other until your money creates the foundation of freedom you once only dreamed of.
“When you know what you are building, progress becomes more important than perfection.”