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Sandy Lee
Engineer-turned short-term rental investor and founder of STR JumpStart, a masterclass for new Airbnb investors
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Jul 31, 2026
How a Mom of 3 Makes $50K a Month With AI (No Experience) - Ep. #322
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17:55Sandy LeeGUEST
That's when, when I was working for this client, I just had this thought of AI is enhancing too fast.
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18:03Sandy LeeGUEST
I'm not saying this to create FOMO, by the way, just because I'm a believer of using AI as a tool, not to replace us, right? However, people who's using AI could replace people who's not using AI, if that makes sense.
Sandy Lee | Short-Term Rentals: How to Know If the Numbers Work
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5:06Sandy LeeGUEST
starting in your 50s? I've always been the crazy one in the family, but not with money.
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5:19Sandy LeeGUEST
I was also getting into that point with my career where I just wasn't sure that I wanted to stay in my career for decades more.
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5:27Sandy LeeGUEST
And interestingly, the last position I had in my corporate career was running our private equity arm in an engineering and construction firm.
6 MINS LATER
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11:27Liz FairclothHOST
When you were looking, okay, do I buy this property or not? When you're saying I looked at it from a 10-year, 15-year kind of vision or landscape, if you will, what did you put into your spreadsheet? What numbers, what considerations did you make to say, okay, in 10, 15 years, this is going to be a strong investment for me? What did you think about, especially with your background in private equity?
How to Build Retirement Income With Short-Term Rentals
3:26

Joseph CroomsHOST
First of all, why did you how did you make the transition? from your prior career and what advantage did it bring you into this real estate?
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3:43Sandy LeeGUEST
And the last couple of years of my business, I ran our private equity arm within our company.
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3:48Sandy LeeGUEST
So that was just a huge, great, um, great education on how investing really worked because I was one of their very traditional people, had a big old 401k, saved really nicely.
How She Went From $0 to $50K/Month With AI (As a Mom)
5:02
24:12

Ryan DoserHOST
Can you break this down for the audience exactly? You know, what percent is what? What's making more money here? Just kind of break that down for us.
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5:11Sandy LeeGUEST
So when I first started this journey, my first client was actually an AI SEO, Ryan, in SEO world.
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5:20Sandy LeeGUEST
I just applied this a lot of different gig on Upwork and I record the Loom video and they got my first deal within the first two weeks.
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5:32Sandy LeeGUEST
and the results that i had been giving to them was really good like it's working yeah the keyword research was up by like i think it was a thousand percent i can share the data with you later on too but anyways it was a pretty good deal but that was 3 000 deal we eventually increased it to 5.5k so that was my monthly recurring revenue that was the first time i'm like oh This is actually working.
18 MINS LATER

Ryan DoserHOST
Like those are the people you want finding your content, not just people who are gonna consume 24 seven looking for freebies.
Why the STR Market Isn’t Scary: Data-Driven Investing and Opportunity with Sandy Lee
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17:08Sandy LeeGUEST
So in that particular case, I would want to see some evidence that the government was about to put $500 million into that town before I thought, no, there might be something here, right? So my first investment was in Steamboat.
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17:23Sandy LeeGUEST
But what was happening in Steamboat that was the typical beyond-the-numbers thing that was magic there was that Aspen had just bought Steamboat.
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17:31Sandy LeeGUEST
So they were investing a ton into the base and the land, more ski area and extra gondola.
She Started Investing in Her 50s, Now She’s Retired with 4 Rentals
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38:16Sandy LeeGUEST
Often it was taking over a department where I didn't have any background and go in and learn the processes, and then try to make everybody happy on the customer service side and within the department while I'm changing everything to make it work, right? So lots of different moving parts, um, when you manage departments or come up with new operations.
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38:35Sandy LeeGUEST
But with short-term rentals specifically, you've got to have all the same skills.
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38:39Sandy LeeGUEST
You need organized, clear, good operations, but you also need to be able to problem solve really quickly and efficiently in order to not let it take over your life or stress you out really badly.
7 MINS LATER
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45:52Ashley KehrHOST
What do you think rookies need to do right now to maybe stay ahead of that curve?
The Mom Who Mastered Claude: How To Build An Audience That Buys Using Claude Code (Step by Step!)
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42:15Sandy LeeGUEST
It's like, "I tested five AI coding tools for non-techies." Obviously, you can change your title as well, but then just it came up with the title and as well as seven different hooks right here like we talked about.
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42:26Sandy LeeGUEST
The pattern interruption, the hook, and the mirror to viewers, which is you're recognizing the viewer.
22 MINS LATER
Making $5,000/Month Cash Flow from One Rental Property (And Retiring in 4 Years)
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39:09Tony J. RobinsonHOST
Can you give us, m- like, what is an example of what that looks like in, in action?
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39:20Sandy LeeGUEST
Often, it was taking over a department where I didn't have any background and go in and learn the processes and then try to make everybody happy on the customer service side and within the department while I'm changing everything to make it work, right? So lots of different moving parts, um, when you manage departments or come up with new operations.
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39:38Sandy LeeGUEST
But with short-term rentals specifically, you've got to have all the same skills.
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39:43Sandy LeeGUEST
You need organized, clear, good operations, but you also need to be able to problem solve really quickly and efficiently in order to not let it take over your life or stress you out really badly.
7 MINS LATER
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46:56Tony J. RobinsonHOST
What do you think rookies need to do right now to maybe stay ahead of that curve?
