Feeling stuck in a job that takes up your time and energy but doesn’t lead to financial freedom? Casey Gregersen once felt the same way.
He worked long shifts in the oil fields, often away from family, and started to question whether there was a better path. With $10,000 in savings and one strategic real estate purchase, he began building a more flexible and secure future.
Today, Casey leads a business that helps others generate passive income through real estate. His approach combines house hacking, creative financing, and real estate tax strategies, the tools that helped him transition from a traditional job to financial independence.
Want to hear Casey’s story in his own words? Watch this short video where he explains how real estate helped him build long-term income and flexibility.
How Did Casey Start Building Passive Income?
Casey now leads a vertically integrated real estate business. His team manages all aspects of the process, like acquisitions, renovations, and property management.
This structure allows passive investors to participate without having to oversee tenants, contractors, or deal sourcing.
Each year, his company completes around 100 transactions. Approximately 40% are fix-and-flips, 20% are wholesale deals, and the remainder are long-term rentals.
Many of these involve creative financing in real estate, such as seller financing and loan assumptions, which reduce the need for large upfront capital.
Can You Learn Real Estate While Working Full-Time?
Yes, and Casey’s experience demonstrates that clearly. After his first property purchase, he continued working in the oil fields on a two-week-on, two-weeks-off schedule.
He made use of long drives between job sites to listen to audiobooks on personal finance and real estate investing.
One book that made a lasting impact was Rich Dad, Poor Dad. It shifted his thinking from earning a paycheck to building long-term assets.
When his first property appreciated, Casey chose to refinance rather than sell. He pulled out $50,000 in equity and used it to purchase a second property, which he converted into a duplex.
That single transaction generated an additional $1,000 in monthly real estate cash flow, without the need for additional savings.
What Are the Best Tax Benefits in Real Estate?
Real estate provides significant tax advantages, which are central to Casey’s investment strategy.
One of the most valuable tools he uses is bonus depreciation. This allows investors to deduct a substantial portion of a property's value, often up to 20%, in the first year.
On a $1 million property, that could amount to $200,000 in write-offs, helping to reduce taxable income from other sources.
Another key strategy is using a cash-out refinance to access equity instead of selling. Because refinance funds are considered loans, not income, they are not taxed.
This allows investors to retain ownership of appreciating assets while accessing capital without triggering capital gains taxes.
How Do You Avoid Mistakes When Flipping or Renting Homes?
Casey’s early investing years weren’t without setbacks. At one point, he overextended himself with multiple fix-and-flip projects financed through hard money loans. When a major sale fell through, he experienced a serious cash flow challenge.
From that experience, he learned several important lessons:
- Keep adequate cash reserves
- Make sure every property has more than one viable exit strategy
- Build relationships with lenders who offer both capital and support
While one lender immediately initiated a default process, another provided mentorship and guidance. That contrast influenced the way Casey now chooses financial partners and supports his investors.
How Did Casey Leave His Job Using Real Estate?
The decision to leave his W-2 job came after a personal moment of reflection. During a baseball game, Casey realized that continuing on his current path would mean missing future milestones with his family.
That clarity helped him take the final step into full-time real estate.
“When I’m sitting on my deathbed,” Casey says, “I don’t want to be glad I stayed at a W-2 job a couple extra years. I want to know I showed up for my son.”
Now, he works with investors, many from oil and gas backgrounds, who want to build passive income through rental properties and gain more control over their time and lifestyle.
His company offers three ways to get involved:
- Lending capital to fund real estate projects
- Purchasing turnkey rental properties that are fully renovated and tenant-ready
- Investing in a diversified fund that includes both fix-and-flips and long-term rentals
Is It Too Late to Start Investing in Real Estate?
Not at all. Casey encourages new investors to begin, even if conditions seem challenging. He sees opportunity in today’s market.
“In five or ten years, people will look back and say, ‘I wish I started in 2025 when interest rates were high and there weren’t as many buyers.’ You just have to start.”
With the right strategies as house hacking, bonus depreciation, and creative financing, real estate remains one of the most accessible paths to long-term financial growth.
Frequently Asked Questions
Q: What is passive income in real estate?
A: Passive income is earnings from rental properties that do not require daily effort. It may come from rent payments, tax benefits, or property appreciation.
Q: How does house hacking work?
A: House hacking involves living in one part of a property while renting out the other spaces to help cover the mortgage and reduce expenses.
Q: What is creative financing in real estate?
A: Creative financing includes alternative methods like seller financing, lease options, or assuming the seller’s existing mortgage to purchase a property with minimal upfront cost.
Q: What are the best tax benefits in real estate?
A: Common advantages include depreciation in real estate, mortgage interest deductions, bonus depreciation, and the ability to refinance without paying capital gains tax.
