Is Real Estate the Key to Time Freedom Or a Trap? My Conversation with David Olds
Real estate is often pitched as the ultimate path to time freedom, financial independence, and passive income. But if you’ve ever been knee-deep in paperwork, chasing down contractors, or wrestling with title companies, you might be wondering is it really that simple?
In this podcast episode of The Money Ripples Podcast, I sat down with David Olds, a seasoned real estate investor and founder of Easy REI Closings, to cut through the hype and talk about what real estate investing really looks like when it comes to creating freedom not another job.
From Broke and Burnt Out to 8,000+ Closings
David didn’t start with a million-dollar fund or a silver spoon. Like many of us, he started broke, with zero investing experience, just a lot of grit and a background in manual labor. His first big break came almost by accident fixing up his own home and selling it for a $52,000 profit. That flipped a switch, and he realized: There’s something powerful here.
Over the years, David built a portfolio, flipped hundreds of homes, and eventually launched Easy REI Closings, a business that now helps investors streamline the most overlooked (and most frustrating) part of the process: getting deals closed efficiently and on time.
Why Real Estate Can Be Hands-Off But Usually Isn’t
Let’s be real. A lot of people get into real estate for passive income, but what they end up with is another job. That’s because they’re trying to do it all themselves from replacing water heaters to chasing down contracts.
David shared something that hit home for me: you’ve got to do the thing only you can do. You might be great at finding deals, negotiating, or raising capital but if you’re buried in paperwork, you’re losing money and time.
As he put it, “Real estate can absolutely be hands-off if you find the right people to trust with the parts you shouldn’t be doing.”
Why 50% of Deals Fail to Close (and How to Avoid That)
This blew my mind: half of all real estate deals fail to close, and it’s usually not because the buyer flaked out or the numbers didn’t make sense. It’s title issues. It’s paperwork. It’s messy trust documents, family estates, or bankruptcy complications.
And if you’re a real estate investor, that’s not just frustrating it’s expensive.
That’s where David’s company, Easy REI Closings, comes in. They’re like the secret weapon for real estate investors who want to scale without getting bogged down. His team handles all the communication with title, collects the documents, coordinates closing everything you don’t want to spend your precious hours doing.
The Shift That Changed Everything: Buying Back Your Time
There’s a reason I talk so much about financial freedom and becoming work optional. It’s not just about having money it’s about owning your time.
David shared how he learned to let go. Like many entrepreneurs, he started by doing everything himself. But once he embraced the concept of buying back his time (shoutout to Dan Martell’s book), his business took off.
He realized he shouldn’t be the one calling realtors to confirm a document came through. He shouldn’t be sweeping the loading dock. And neither should you.
If you want to grow whether that’s 10 deals a year or 100 you need to get crystal clear on what your time is worth, and spend it doing only what grows your income and impact.
The Ripple Effect: Helping Others Scale
One of the things I respect most about David is his heart for creating a ripple effect. He’s not just doing this for himself anymore. Now, he’s helping his team, his partners, and even newer investors get in the game and level up.
He’s buying deals with his team. Helping them buy their first rentals. Coaching others through their first investments. That’s the kind of legacy I’m all about and I know many of you are, too.
Takeaways for Real Estate Investors
Here’s what I want you to walk away with after this episode:
- You don’t have to do it all. Focus on the part of real estate that lights you up and delegate the rest.
- Title issues kill deals. Having a trusted team to handle this can mean the difference between scaling and stagnating.
- Real estate freedom is possible. But it only comes when you own your time—not just more properties.
- Systems scale wealth. If you’re still managing every detail yourself, it’s time to rethink your model.
Final Thoughts
At the end of the day, real estate is just a vehicle. How you drive it determines whether you end up free or frustrated.
But with the right systems, support, and mindset, it can absolutely deliver the freedom and income you’ve been dreaming about.
So don’t do it all alone. Don’t let paperwork and processes become your bottleneck. Start building the kind of business that actually serves your life.
Let’s keep building that ripple effect together.