Real Estate Pros · October 29, 2025 · 23 min listen

Why I Skip “Good” Deals: Greg Gaudet’s Risk-First Underwriting, Safer Flips, and Rentals in Maui

Show summary

In this episode of the Real Estate Pros podcast, host Michelle Kesil interviews Greg Gaudet, a real estate investor based in Maui. Greg shares his journey into real estate investing, discussing his focus on wholesaling, flipping, and rentals. He emphasizes the importance of consistent marketing and a conservative approach to deal-making, especially in the unique Maui market, which faces challenges such as potential legislation affecting vacation rentals. Greg also outlines his strategies for finding off-market deals and reflects on his future goals following personal challenges. The conversation provides valuable insights for aspiring real estate investors.

Key takeaways

Underwrite every deal for the worst-case scenario: double rehab costs, sale at the lowest comp, and a longer timeline than expected; only do the deal if it still doesn't lose money.
Consistent marketing matters more than any single channel; split lead generation fairly evenly across direct mail, online marketing, foreclosure auctions, and cold calling, then shift focus toward whichever source is currently producing.
On off-market seller calls, ask the seller's desired price first, explain the value of an all-cash as-is offer, give a low anchor range without a hard offer, and suggest they list with a realtor instead — genuinely motivated sellers often come back asking for a firm offer.
A real example: bought a Maui condo for $415,000 (50% of a declined $832,000 offer), put in $20,000 rehab for $435,000 all-in, projected a conservative $550,000 sale, and actually sold for $590,000.
Maui faces legislation that could ban vacation rentals in apartment-zoned buildings, which combined with a broader market decline has caused some condos to lose up to 50% of their value — reinforcing the need for conservative pricing.
Save aggressively by keeping living expenses flat even after income jumps; Greg lived on about $40,000/year before and after moving to a six-figure job, funneling the difference into buying low-end cashflowing condos on Maui.
Have a clear prenuptial or postnuptial agreement that spells out an asset split (not necessarily 50/50) before scaling a rental portfolio with a spouse, to avoid major net worth loss in a divorce.

In this episode

About the guest

Greg Gaudet owns Maui Home Buyers and runs a real estate investing business in Maui focused on wholesaling, flipping, and rentals. He started as a real estate appraiser out of high school in 2002, began investing around 2016 after saving aggressively from a six-figure job, and later partnered with BiggerPockets' Brandon Turner to flip houses on Maui.

Listen to the audio

“We just finished a flip where the condo had been worth $830,000 two years ago and we bought it for $415,000.”
Greg Gaudet

“I'd rather miss a good deal than do a bad deal.”
Greg Gaudet

“I just have to do the best deals that come across my desk.”
Greg Gaudet

Maui real estateflippingwholesalingrentalsoff-market dealsvacation rental legislationconservative underwritingforeclosure auctionsdivorce and asset protection

Questions answered in this episode

How does Greg Gaudet underwrite flips to avoid losing money?

He calculates the worst-case outcome before doing a deal: what happens if rehab costs twice as much as expected, if the property sells for less than the lowest comp, and if the flip takes six months instead of his usual three to four. If the deal still doesn't lose money under those conditions, he'll do it; otherwise he passes, even if other investors later make money on similar deals.

What is happening in the Maui vacation rental market right now?

There is legislation threatening to ban vacation rentals in buildings zoned for apartment use, which puts a large chunk of Maui's vacation rental condos at risk of losing their right to operate as short-term rentals. Combined with a broader market decline, this fear has caused some condos to lose up to 50% of their market value.

What lead sources does Greg Gaudet use to find off-market deals?

He splits his effort fairly evenly across direct mail, online marketing, foreclosure auctions, and some cold calling, and shifts focus toward whichever channel is producing deals at the time. He expects foreclosures to increase given declining prices and high interest rates, so he's currently paying closer attention to that source.

What negotiation tactic does Greg use with motivated sellers?

He asks the seller what price they want, then explains the value an all-cash, as-is, quick-close buyer brings versus listing with a realtor. He gives a low anchor range (for example, low 400s) without making a hard offer and tells the seller they'd likely do better listing with a realtor, which often prompts genuinely motivated sellers to come back and ask him for a firm offer, flipping the negotiation dynamic.

What example deal illustrates Greg's conservative approach paying off?

He bought a Maui condo for $415,000 that had been worth $830,000 two years earlier and had a declined offer of $832,000. The lowest comp on market was about $600,000; he put in $20,000 of rehab for $435,000 all-in, projected a $550,000 sale in a worst-case scenario, and ultimately sold it for $590,000.

Why does Greg recommend a prenuptial or postnuptial agreement for real estate investors?

After going through a divorce while most of his rentals were titled in his name, he lost a significant portion of his net worth. He suggests a prenup/postnup doesn't have to mean the other spouse gets nothing; it can simply spell out a fair split (he mentions he might have proposed 25% rather than the 50% default under state law) to avoid disputes and asset loss if the marriage ends.

Resources and links

Full transcript

Greg Gaudet (00:00)

We just finished a flip where the condo had been worth $830,000 two years ago and we bought it for $415,000. So we actually paid exactly 50 % of what the seller had an offer for $832,000 that she didn’t take. And we bought it for $415,000. The lowest comp on the market was about $600,000.

So we said okay, and this was a good unit corner unit next to the pool great location Didn’t really need much rehab. I think we put 20,000 into it just to make it make sure it was like the most attractive unit on the market and we ended up so we’re 435 all in and We I projected that we would sell it for 550 sounds like the lowest sale 600 Markets going down will be the best unit on the market

if everything goes wrong, like I don’t see a way that we get less than 550. Well, we ended up selling it for 590, so we did make money.

Michelle Kesil (02:33)

Hey everyone, welcome to the Real Estate Pros podcast. I’m your host, Michelle Kesil, and today I’m joined by someone that I’m looking forward to chatting with, Greg Gaudet, who owns Maui Home Buyers and has his real estate investing business in Maui. So excited to have you on the show today, Greg.

Greg Gaudet (02:54)

Thanks for having me.

Michelle Kesil (02:56)

Of course, think our listeners are really going to take something away from how you’re working on the Maui market with your rentals, your flips, your wholesales, and everything that you’re up to. So let’s dive in.

Greg Gaudet (03:14)

That’s it.

Michelle Kesil (03:15)

First off, for those not yet familiar with you and your world, can you give the short version of what your main focus is?

Greg Gaudet (03:25)

My focus is split pretty equally between wholesaling flipping and rentals. ⁓ basically My focus or I should say my focus is on finding deals and then as the deals come in My business is spreading pretty evenly amongst those three ⁓ Disposition methods when a deal comes in. I just figure out is this deal

something that I want to flip and have the bandwidth and ⁓ ability to flip right now? And can I make the profit I want to make? And if not, can I wholesale it? ⁓ Or does it make sense as a rental and am I in a position right now to, ⁓ with the capital to buy a rental?

Michelle Kesil (04:06)

Awesome. How did you get started as an investor?

Greg Gaudet (04:12)

So I’ve always wanted to become an investor. I was a real estate appraiser right out of high school in 2002 up until the recession hit. And at that time I was seeing people that were flipping houses and that was really attractive to me because I’m just passionate about the real estate industry and I saw all the success that people were having with that.

I unfortunately didn’t take action and start at that time, but the seed was planted and around 2016 2015 actually from 2012 till 2015 I was working in the real estate industry and you know again the seed was there I was like really interested in eager to invest But it wasn’t in 2016 when I got my first

Well-paying job that I felt like okay now I actually have the ability to start investing and at that time I found all of the podcasts like yours and you know online resources and started educating myself and I wish that I had found these things sooner because I could have started I didn’t need the high-paying job. I didn’t know that ⁓ I could start with like

very little money, but once I got the high paying job, I saved aggressively. ⁓ You know, I had been living off of something in the $40,000 a year range before. And so when I started making six figures, I kept living off 40,000 saved all the rest and ⁓ was able to quickly save up enough to buy ⁓ some low end condos here on Maui that cashflow really well. And that was kind of my foot in the door. ⁓ From there, I,

I met another real estate investor influencer, Brandon Turner from BiggerPockets, and ⁓ I basically sold myself to him and became business partners with him to flip houses on Maui, which just further ⁓ scaled my ability to earn more income that I could just continue saving and adding to the pile to buy more rentals.

Michelle Kesil (07:05)

Amazing. That’s so cool that you were able to really work your way and get those partnerships and have that stepping stone into this career.

What are some of the main keys that you would say have allowed your business to be able to scale and run smoothly?

Greg Gaudet (07:34)

⁓ I would say consistent marketing has been really important. ⁓ It’s easy to kind of, you know…

rest on that and get tired of like you’re sending out all this direct mail, right? And like getting calls, but not getting deals. So being consistent, and then I would also say what’s been critical to us has been being conservative. I’ve seen a lot of investors, ⁓ you know, there’s been deals that we’ve passed up on and ⁓ I’ve seen other investors do those deals. And a lot of them have

made money, right? Just because, but I also believe a lot of them made money because the market was good. The market made them money. Like the investor didn’t make the money. they had, if the market had not been as good as it was, they would have broken even or lost money. So, ⁓ as, as much as it hurts to see another investor do a deal that I looked at and came so close to doing, ⁓ and then to see them make money on it, I’m also, I also just remind myself like, well, it’s great that it worked out for them, but it still wasn’t

right for us because if things didn’t go as planned, they wouldn’t have made money. And so that’s kind of my approach to it. So every deal we look at is

What will be the outcome if like everything goes wrong? So if rehab costs twice as much as we expect, if we sell for like less than the lowest comp, ⁓ if it takes us, you know, six months or something, because our flips are usually really quick, we’re usually in and out in three to four months. ⁓ If everything goes wrong, what…

what price do we need to be at so that we’re still, we don’t lose money. And so that’s been our approach and I think that’s been the key to ⁓ us, our longevity and even though we’ve seen some investors come in and fail and leave during the time we’ve been operating, ⁓ I think that that’s what’s given us the staying power.

Michelle Kesil (10:16)

Yeah, absolutely. Can you expand on how that is maybe unique to the Maui market? know when we chatted before, you were mentioning some of those points, and I think it would be good to share with the audience.

Greg Gaudet (10:35)

Yeah, well, some of the unique things that we’re dealing with on Maui is legislature to ban vacation rentals ⁓ in buildings that are zoned for apartment use, ⁓ which I won’t get into the details, but basically a huge chunk of vacation rental condos on Maui are being threatened to lose their right to operate as vacation rentals, which has.

The timing is crazy, right? Because the market has already been kind of in a decline, I think nationwide. Most markets at least are seeing at least a slight decline in pricing. And that specifically, that has been exacerbated on Maui and condos especially because of the fear that it’s creating. And a lot of condominiums have lost up to 50 % of their market.

market

value. So again, we’re just the same thing as we’re just really conservative.

if everything goes wrong, like I don’t see a way that we get less than 550. Well, we ended up selling it for 590, so we did make money.

It worked out and again, that conservative kind of just real careful approach has been working out for us pretty well.

Michelle Kesil (12:50)

Yeah, that’s amazing. Sounds like that strategy is what you need to continue to do.

Greg Gaudet (12:59)

Yeah, and we are potentially missing a lot of deals by being so conservative. But like I said before, I mean, we’d rather miss a good deal than do a bad deal. And I’d rather see somebody else succeed and make some money on a deal that we missed than be overeager and over like greedy and have to get every deal that comes over my desk and then end up.

losing a ton of money and wiping out a year or two worth of profits or potentially even putting us out of business if it went really bad. So yeah, there’s a little bit of, I think, humility that I need to practice in that and accepting that I don’t have to do every deal that comes up on Maui. I just have to do the best deals that come across my desk.

Michelle Kesil (13:58)

Absolutely. What is your strategy for finding the deals?

Greg Gaudet (14:05)

⁓ I would say, you we don’t have any particularly unique strategies. It’s kind of the same as most ⁓ investors and everybody we, you know, we listen to, but it’s pretty equal, I would say, amongst ⁓ direct mail, ⁓ online marketing, foreclosure auctions, ⁓ and some cold calling. And there’s not one strategy, I think, that produces the deals.

So we make sure we’re covering all of them and…

we pursue whatever deals, whatever method they come through. ⁓ We do, if I see more deals coming through direct mail, then I start to focus a little more on those. Right now, I’m starting to see, it maybe hasn’t fully happened yet, but I fully expect that we’re gonna see more foreclosures. And so I’m paying a lot more attention to those just because again, what I’ve talked about in the Maui market especially, but also in the market just nationwide,

with prices kind of on the decline, interest rates too high for people to refinance. I think there’s a lot of potential for an increase in foreclosures. ⁓ So it does ⁓ ebb and flow between the different lead sources, but we cover them all and ⁓ we focus more on one if there’s a particular need or the market indicates that that’s the strong one at the moment.

Michelle Kesil (16:20)

Yeah, of course. You know, when we chatted before, you were mentioning that you really are centered towards the off-market buys. Can you expand what that looks like?

Greg Gaudet (16:33)

Yeah, so actually I’ve only ever bought one property that was on market. It was the second condo that I ever bought. But besides that, I’ve never bought anything from the MLS. ⁓ And not that there’s anything wrong with that. I have plenty of friends who make a great, you know, grow investing businesses by only buying on the MLS. But ⁓ for just the way that my business has developed has… ⁓

has just organically grown through buying off market. so I basically my phone is where the deals come from. They call me most of the time. Again, except cold calls. I do some outbound calls myself. ⁓ But yeah, so a call or a seller’s sellers call me all the time. ⁓ I have conversations going on with them where ⁓ I feel them out.

figure out like, okay, what’s your motivation? What kind of price are you looking for? And right off the bat, the first thing is I want to know how much are you hoping to get for the property? And then once they tell me that, and it’s usually market value, right? And they usually want to close quickly for all cash as is, and they need repairs and all this stuff, but they still want the same amount as the perfectly good condition comp that just sold on MLS. So I kind of give them a quick explanation, like, look, here’s the deal.

when you’re selling to an off market, you know, all cash investor, we’re bringing a lot of value. I explained the difference ⁓ and I let them know like if…

We couldn’t get anywhere near so again right now i’m working on a deal on the big island of hawaii where the seller Said she wants 550 and i’m like, okay. Well after we put 100,000 into it. It’s gonna be worth 600 So obviously we can’t pay 550 So i’ll explain all that to her let her know. Um, I often will just let them know up front like hey I don’t want to make an offensive offer But I mean we would be somewhere like in the three some like our offer would start with a three or we would be somewhere

in the 300s or high 300s, know, something like that. I just give them kind of a ballpark idea. Like, look, this is, so I’m setting that low anchor. And then I’m letting them know, like, I don’t, I don’t want to offend you. So I’m not going to actually like make a hard offer. think in this case, if you want 550 by all means, the best thing for you to do is call it realtor and listed on the MLS. It’s going to take, you know, it take six months. You’re going to pay commissions. You’re going to make repairs, you know, you’re going to, I’m going to list all the kind

downsides of listing with a realtor, but I’m going to tell them like, you’ll get, may not get 550, but you’ll, you’ll get a lot more than what I’m going to offer. ⁓ And what I’ve found is that approach has actually been really productive for me. I think.

you know, in the right case for, for a most, for a lot of people, say, okay, I’m going to call a realtor, but for the people that are actually motivated sellers, the right people that I want to reach, they come back. Like the condo I just spoke about that I bought for 415. I ⁓ told her that exact thing. said, you should call a realtor. You’ll probably get 550. ⁓ My offer would be low 400s. And, ⁓ and she, she came back to me she was like, well, I really want to sell to you. Like, can you, can you actually like give me a,

⁓ a firm offer. And so that turned the tables from like me trying to sell her to her trying to sell me and saying like, well, wait a minute, will you make me an offer? Because again, the response was like, I’m not even gonna make you an offer because it’s gonna be offensive. You should call a realtor. I would be like low 400s. And then that kind of triggers her to come back and say,

Well, what is the offer? mean, I’m really interested in working with you. And so anyways, that approach has been working for me.

Michelle Kesil (20:26)

Yeah, that’s such a cool strategy. haven’t heard many people talk about that. So I love that you’re having something that works for you.

Greg Gaudet (20:27)

Yeah.

Michelle Kesil (20:39)

Awesome. So what are some of the goals that you have for where your business is heading?

Greg Gaudet (20:49)

I think right now so I just

went through a divorce and basically that after having been, I was married for the majority of the time I grew my business and all the rentals I bought in my name. ⁓ So I did lose a significant portion of my net worth and what I’ve built due to ⁓ the divorce. so ⁓ quick note on that is like, I strongly recommend having a very clear prenuptial or if you’re already married postnuptial agreement. ⁓

I think everybody thinks of a prenup as something that says if you get divorced, the other person doesn’t get anything, but it doesn’t have to be that. ⁓ can be just, think the way I think of a prenup or a post-nup is just like spelling out what would happen. So you might spell out that the partner, ⁓ husband or wife is gonna get half of the other partners.

⁓ net worth in a divorce, which would be the same as, you know, what a lot of state laws are. But, ⁓ but you could also say like, okay, in my case, I, I probably would have said like, how about if I give you 25 % of what I’ve built? So it’s not that I didn’t don’t want to take care of my ex-wife. It’s that, that like, I didn’t want to give her half of everything that I built. ⁓ so

Yeah, I would say going forward, my focus right now is gonna be first off is paying down debt because the divorce, ⁓ I’m having to pay off a few mortgages ⁓ to give her some, I’m giving her four condos free and clear. So I have to pay off all those mortgages and I have to give her some cash too. So I’m gonna have some debt that I have to pay off as well as debt just from buying other rentals. So while the market’s in this weird funk that it’s in, my focus is to do flip.

pay off those debts and put myself into a position where I can be ready to start acquiring more rentals once the market conditions improve or once I feel like prices aren’t going to drop in a significant way or they’re not going to drop significantly from where they’re at now. Right now I feel like they’re going down. I think it’s a good time to buy but there could you know

they haven’t stopped going down yet. So I’m kind of waiting for that to happen and to get my debt paid off and then to acquire some more rentals to make up for ⁓ what I lost in the divorce.

Michelle Kesil (23:26)

Yeah, absolutely that makes sense. You never know how different obstacles can affect you. yeah, it’s important that now you have those takeaways and lessons to share with others.

Greg Gaudet (23:44)

Yeah, and hopefully that resonates with someone. if any listeners are dealing with a divorce or an unstable marriage or getting married maybe, you know, in the process of acquiring rentals and scaling. And I think ⁓ it’s really important to… ⁓

Michelle Kesil (23:44)

Awesome.

Greg Gaudet (24:03)

to have those tough conversations and say like, okay, look, in the case that things don’t go as planned, let’s just spell out what we think would be fair and right for everyone.

Michelle Kesil (24:16)

Yeah, definitely.

So before we wrap up here, if someone wants to reach out, connect, learn more from you, where can people find you and reach you?

Greg Gaudet (24:30)

They can find my website is MauiHomebuyers.com or they can reach me directly. ⁓ My Instagram is at MauiHomebuyers ⁓ or my personal Instagram is at investor.Greg.

Michelle Kesil (24:47)

Perfect. Well, I appreciate your time, your story, and your perspective. Thank you for being here.

Greg Gaudet (24:54)

Thank you for having me.

Michelle Kesil (24:55)

Of course. And for the listeners tuning in, you got value, make sure you’ve subscribed. We have more conversations with operators just like Greg who are building real businesses. And we’ll see you on the next episode.