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Cameron Masters

Cameron Masters

Founder of Remote Retreats, a luxury short-term rental management company in Lake Tahoe and Yosemite; STR entrepreneur who scaled from 18 to 140+ Airbnb units through company acquisition

Aug 18, 2026

10:38
Tell me what what's kind of going through your head at the moment.
10:42
I think we learned a lot of improvements we could have made during due diligence, especially since the company was so much bigger than the other company that we're like, we're not going to drag them into our systems.
10:50
And this company does do, we do 30% direct bookings.
10:54
So we want to keep that brand.
10:55
We have people that have been staying us for 25 years in a row, every single summer.
10:59
So we have a completely different demographic where we needed to keep their systems.
11:02
And so we just assumed things like, hey, they have automated messaging.
14:12
I'm just curious your thought.
6:36
So again, walk us through what does due diligence look like when you're analyzing a management company?
6:42
Well, one, due diligence is much more expensive than I expected.
6:46
First off, if you're looking at it, I highly recommend that you speak to a lawyer before you submit an LOI.
6:51
If you get that signed, it's hard to retrade after you get into a contract.
6:54
I know some people say contrary, but based on our experience, it would have been a lot better if we would have just had our lawyer spend a half hour and even say, hey, here's the framework I would use going forward if it's not for this company, for another company.
7:06
But essentially, it's a whole bunch of documentation and a whole bunch of financial looking and getting access to all of their systems and digging in and looking at their customer concentration, what their contracts look like, what their financials are and doing the reconciliation and all that.
7:19
If we're going to do an asset or stock purchase.

9 MINS LATER

16:48
What's been the hardest part of the last two months after acquiring a 114 contract management company?

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