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Sandy Lee

Engineer-turned short-term rental investor and founder of STR JumpStart, a masterclass for new Airbnb investors

Jul 31, 2026

17:47
Now, how did you get your second and third and fourth clients?
17:50
Yeah.
17:50
So it was coming from inbound lead.
17:53
The second, third, fourth client, they were all different.
17:55
That's when, when I was working for this client, I just had this thought of AI is enhancing too fast.
18:03
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.
18:16
It's not AI replacing, it's the people.
21:03
Yeah, please.
5:02
What gave you that confidence, right, to move forward, especially
5:06
starting in your 50s? I've always been the crazy one in the family, but not with money.
5:11
So this was a whole different thing.
5:14
My son had gone to school in Colorado, so that helped.
5:17
I live in Texas.
5:19
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.
5:27
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

11:27
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?
3:26
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?
3:36
Yeah.
3:36
So this is kind of a fun story.
3:38
I loved my career.
3:39
I was in engineering and construction for more than 30 years.
3:43
And the last couple of years of my business, I ran our private equity arm within our company.
3:48
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.
7:52
so then
5:02
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.
5:10
Yeah, 100%.
5:11
So when I first started this journey, my first client was actually an AI SEO, Ryan, in SEO world.
5:18
I got my first gig through Upwork.
5:20
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.
5:29
And that was a blog automation for SEO.
5:32
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

24:12
Like those are the people you want finding your content, not just people who are gonna consume 24 seven looking for freebies.
17:06
What are your thoughts?
17:08
Right.
17:08
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.
17:22
We talked a lot about it last time.
17:23
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.
17:31
So they were investing a ton into the base and the land, more ski area and extra gondola.
17:38
And none of this had actually happened yet.
21:54
This is
38:07
Like what is an example of what that looks like in, in action?
38:10
Sure.
38:10
I think, I think you hit the nail on the head.
38:12
I'd have to go into situations without a lot of information.
38:16
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.
38:35
But with short-term rentals specifically, you've got to have all the same skills.
38:39
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

45:52
What do you think rookies need to do right now to maybe stay ahead of that curve?
42:08
Let's go to the, let's go to the next, next step.
42:10
Yeah.
42:11
So I love that.
42:12
So here's the script.
42:13
Now, um, it came up with the title.
42:15
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.
42:26
The pattern interruption, the hook, and the mirror to viewers, which is you're recognizing the viewer.

22 MINS LATER

64:30
Jay Sh- you could do Jay Shetty.
39:09
Can you give us, m- like, what is an example of what that looks like in, in action?
39:13
Sure.
39:13
I think, I think you hit the nail on the head.
39:16
I'd have to go into situations without a lot of information.
39:20
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.
39:38
But with short-term rentals specifically, you've got to have all the same skills.
39:43
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

46:56
What do you think rookies need to do right now to maybe stay ahead of that curve?

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