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I'm Ali Rae and I love building brands.
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This week we’re diving into passive real estate investing, and honestly, I think this conversation is one so many short term rental owners need to hear.
I sat down with Yasha Wells to talk all things private equity, capital raising, commercial real estate, and what investing can look like when you want your money working for you without creating another full time job.
Because if we’re being honest… a lot of us got into short term rentals after hearing the words passive income and quickly realized that wasn’t exactly the reality.
I think most short term rental owners enter this industry for one of two reasons:
You love real estate.
You love hospitality.
But almost all of us start with some version of:
“This could become passive income.”
And then reality hits.
Guest messages. Cleaners. Contractors. Maintenance. Pricing. Systems. Marketing.
Suddenly you realize you didn’t buy an investment. You built another business.
Now for some of us, that’s exciting. I genuinely love hospitality and guest experience.
But for others, eventually the question becomes:
Can I stay in real estate without creating another full time job?
That’s exactly where this conversation started.
And yes… THIRTY.
When Yasha said she had 30 rental arbitrage units at one point, I think I physically paused.
Because if you’ve managed even one short term rental, you know the operational side can become overwhelming fast.
Thirty meant:
• Guest communication
• Cleanings
• Maintenance issues
• Damages
• Contractors
• Turnover coordination
Basically chaos.
She shared that while it worked during the post COVID travel surge, eventually she realized she didn’t want another business that required constant daily involvement.
And honestly? I think a lot of listeners can relate to that.
I think private equity can sound intimidating because it feels like one of those words people throw around assuming everyone understands it.
So here’s the simple version:
Instead of buying and operating the property yourself, you invest money into a larger project being run by experienced operators.
They handle:
• Acquisitions
• Development
• Construction
• Management
• Operations
You become the investor.
Not the operator.
Or as Yasha put it:
“Real estate without tenants or toilets.”
Honestly… that line deserves an award. Because immediately you understand exactly who she’s speaking to.
Yasha repeatedly came back to one thing:
The deal matters. But the operator matters more.
And I thought that was such an important distinction. Because when we talk about investing, people immediately focus on numbers:
What’s the return?
What’s the timeline?
How much can I make?
But she encouraged investors to ask questions like:
Have you done this before?
What is your track record?
Have you ever lost investor money?
How are you getting paid?
What fees exist inside the deal?
Those questions felt incredibly practical and honestly apply to way more than private equity.
Oddly enough, one of my biggest takeaways had nothing to do with investing.
Yasha lost her Instagram account. Completely. Over 10,000 followers gone overnight with no warning, no explanation, no timeline. And if you create content online, I know your stomach just dropped reading that.
But she had one thing that saved her: An email list.
She immediately reached out to her audience, rebuilt trust, and started rebuilding momentum.
I feel like I scream this from the rooftops constantly: Build your email list.
Because followers are borrowed. Email lists are owned.
I think the biggest lesson here is that diversification doesn’t mean walking away from what you built.
You can absolutely love short term rentals and hospitality and still explore other investment opportunities.
You can build multiple income streams. You can create more freedom.
And sometimes scaling isn’t about adding more doors. Sometimes it’s about asking better questions.
Listen to the full Brand and Market episode with Yasha Wells and hear the entire conversation around private equity, passive investing, and building wealth without tenants or toilets.
And if you’re sitting there wondering whether your next investment has to look exactly like your last one…maybe this is your sign to think a little bigger.
Until next time, I’m cheering you on as you build your dream brand and business. 💛
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