David Greene Show I Building A Badass Site For Your STR (and how to save when traveling) I Episode 125

The David Greene Show

David Greene

Entrepreneurship, Business

4.9 • 701 Ratings

🗓️ 21 April 2026

⏱️ 78 minutes

🔗️ Recording | iTunes | RSS

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Summary

When Gil Chan bought his first two STR’s, he fell in love with the industry. It wasn’t long before he realized things were changing rapidly, and it was tough staying on top of all the changes in the industry. Gil noticed he could improve on the generic direct booking websites provided by OTA’s, made his own custom site, and was told by his friends he needed to quit his job and go full time. And he did! Gil shares his story of how he built craftedstays.com, how it’s helped improve his own properties revenue, and the services he offers to other STR owner/operators. We cover common scams guests use, ways Airbnb has moved away from their original value, and how to set up a direct booking site to boost your business. Download today!

Transcript

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0:00.0	Welcome to Real Talk Real Estate, the show where we cover how to build wealth in real estate with no fluff, no BS, and no sales pitches. I'm David Green, and I've been doing this for over 10 years. I've seen the ups, the downs, and everything in between. This is the show where we pull back the curtain and show it to you too. So if you want to build wealth through real estate or you just love learning about it you found your home what's going on
0:21.7	everyone welcome to real talk real estate i'm david green and this is the david green show and i'm joined
0:26.6	today by a vanguard frontier person what would you call yourself gil chan of crafted stays
0:34.1	um describe yourself to the audience of how you see yourself in the STR space.
0:39.3	I would say maybe a disruptor, innovator. I come from the tech space, the startup space. So I feel like I'm not that unique, but maybe to the STR space, I look at things very, very differently than other folks.
0:53.3	Yeah. And that's why you're here today. Not just because you're a disruptor, but because you're disrupting something that needs very badly to be disrupted. And that is frankly, in my opinion, the guests that stay at a short term rental that hold the owner hostage because of the five star ranking system in Airbnb's algorithm. Now, I don't want to speak for you, Gil.
1:12.2	Maybe you don't see it as bad as I do.
1:13.6	So let me just give a disclaimer.
1:14.9	That was my opinion, not Gil's.
1:16.4	But why don't we just start off by you explaining what problem you saw in the industry and why you started crafted stays?
1:22.7	Yeah.
1:23.1	So I think we, my wife and I were property owners, property managers, ourselves too, or hosts.
1:30.8	And back, we started during the beginning of the pandemic, I think 2020, 2021.
1:37.2	And we bought our first cabin and we had probably 95% of our bookings coming from Airbnb.
1:42.2	And that was good.
1:43.1	It felt great because what other asset
1:45.5	class can you, or even asset that can you buy, put it in service, and immediately get revenues
1:50.4	just like that. You didn't have to do any marketing, none of that stuff. But over time,
1:55.1	we felt like we were at the mercy of the OTAs, primarily Airbnb. And we wanted to build our own direct booking website.
2:03.9	And we either had the choice of building it on the PMSs. A lot of them give you free,
2:09.2	free websites. And if we wanted anything better, we would have to pay an agency $6,000 to $10,000,
2:16.3	sometimes even more, better Lipsin.
	...

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