Snapshots Tampa Bay

From Clutter To Calm: How Caring Transitions Helps Families Downsize, Sell, And Start Fresh

• Lisa and Candace • Episode 12

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What if the hardest part of helping an aging parent wasn’t the stuff, but the stress? We sit down with Caring Transitions owners Billy and Jeff to unpack a smarter, kinder way to handle downsizing, estate cleanouts, and senior moves in the greater Tampa Bay area. From turning a “hoarder’s dream” into a market-ready listing to recovering value through online auctions, this conversation maps the steps families can take to save time, reduce costs, and protect what matters.

We dig into the full-service approach: space planning that reimagines life in a 500–700 square foot apartment, digital inventories that strengthen insurance claims and simplify estates, and coordinated teams who clean, catalog, sell, donate, and prepare the home for photography without endless weekend trips or hotel stays. Billy and Jeff share how CTBids auctions can fund the process, how donations support local nonprofits and families in transition, and why even small items—like half-used cleaners—can make a real difference when placed in the right hands.

You’ll also hear how a national franchise network creates continuity when loved ones live in different states, offering trusted referrals and a single point of contact from start to finish. In a world where scams increasingly target seniors, working with licensed, insured, background-checked professionals is more than convenience—it’s protection. If the holidays open a window for hard conversations, use this guide to talk about what to keep, what to sell, what to donate, and how to plan a move that preserves dignity and reduces friction for everyone involved.

If you’re ready to simplify the transition and ensure a smooth process for your family, reach out to Billy or Jeff with Caring Transitions for personalized assistance:

  • Contact Billy: wsigmund@caringtransitions.com | (813) 295-2950
  • Contact Jeff: jnewcomb@caringtransitions.com | (727)458-5826  

Get started today!


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Lisa:

Hi everybody, and welcome to Snapshot Tampa Bay with Candace and Lisa. Get ready to dive into the exciting and colorful world of the greater Tampa Bay area. Whether you're sorting out a military move, checking out the senior living scene, or just on the hunt for the coolest local spots, let's get started and have some fun.

Candace:

Hello there, it's Candace here with Lisa. Hi Lisa. Hey. We're excited to spend some time with you today. And today we're discussing something that's kind of really dear to both of us as we both have elderly parents and we've both dealt with clients who are elderly as well.

Lisa:

So Lisa? Yeah. Well, you know, we've talked about this a number of times, and we also went through something with my mom of being scammed, and there are a lot of people out there who are trying to take advantage of people who are aging, um, and they need a lot of help, especially in this social media AI generation that's coming up. So I didn't, you know, I took this so much to myself after my mom sort of got scammed. I went ahead and got my certified senior professionals um uh certificate just because I wanted to make sure that I could help people a little bit more. I know that you and I have talked about this a whole bunch, and we want to bring people and businesses and organizations that actually take care of our people who are aging. I don't want to say elderly, but people who are aging because it doesn't have to be somebody who's in their 80s, it could be somebody who's in their 50s and they just want to have a change of life, maybe a transition. A transition. Yeah, a transition in their life. So, with that, we have two amazing gentlemen here today who um Candace has personally worked with this company. It's called Caring Transitions, and we have Billy and Jeff, and they're gonna tell you a little bit about what they do for people who are transitioning um in their lives.

Candace:

Yes, so I worked with Billy personally on a listing for my clients who the grandparents have passed away both within the last six months of when I met with my clients. And the house, to put it mildly, was a hoarder's nightmare. And the clients I don't think it was a hoarder's nightmare. I think it was a regular person, but a hoarder's dream. That's that's the way it's a hoarder's dream. And my clients lived three hours away. They have two kids that are very actively involved in sports. They couldn't figure out when they were gonna come over and clean the house, they were just gonna order a dumpster, throw everything away, basically just clean it up, but they didn't know when they were gonna be able to do it. They would have had to get a hotel because they couldn't have stayed in the house. And Billy can attest to this, they could not have stayed in the house because it was it was a disaster. So I I asked around a little bit in the office with some other real estate agents. I was introduced to an estate company. That estate company said, Well, we don't really do that, but here's who you need to call. Oh, good. So another company you said. Is that who you need to call?

Lisa:

Yes, exactly.

Candace:

Yes. So that's how I met Billy. So Billy and Jeff, why don't you go ahead and introduce yourselves a little bit, talk about the areas that you service, and we'll just ask you a few questions.

Billy:

Okay, great. Well, thanks for having me. This is uh Billy, and um, you know, what working with your client, it was it was such a privilege because you know, we we interact with so many families that are just they feel so overwhelmed. And uh, you know, I think that's the rewarding part of this profession is that we come in with just a variety, a menu of services. So, you know, you really are just working with with one single company when it comes to downsizing or space planning or uh you know liquidation of their personal property, um, as well as um cleaning services to clean out the house and get it prepared for uh for make it show ready um for photography for you know to get it listed. And um my territory is um from Plant City all the way down to Sun City and all the sunshine in between. Um mainly down in the South Shore area. And um, and yeah, uh we've been we've been open for about a year and a half now and just we're uh loving every day of it. And so we it's an amazing part of being in the industry, is just helping not only seniors but but families and uh and to see the um to see the uh the relief on their faces um when you come in and uh you let them know that hey, we'll handle all of this for you. Uh it the just to see the the worry um just evaporate from their faces, knowing that they can trust a national brand company um who's licensed and insured, all of our employees are background checked. So we're we're bringing a service that is that is valuable to our clients.

Candace:

It was very, very valuable to my clients. They could not stop raving about what you guys did for them because just the release of all of that work. You ended up selling up a lot of the stuff that they had in that house.

Lisa:

And they were just going to throw that stuff away.

Candace:

They were just gonna throw it away and they ended up actually making money.

Billy:

Yeah, they paid for our services and profited.

Candace:

Yep, and then profited it, and then they also didn't have to get a hotel, they didn't have to disrupt their kids' life and put their kids through that. The stress that you took off of both of them was really, really valuable to them. So thank you very much.

Lisa:

Now, you guys are this is a franchise, which is amazing because with with us being here in Florida, people can call carrying transitions in their area because you guys service certain areas. So Jeff is from a different area. So, Jeff, what area are you uh servicing?

Jeff:

I'm South St. Petersburg, so I'm kind of the southern end of Pinellas County.

Lisa:

Okay.

Jeff:

And since we're a lot more compact, my uh zip codes aren't near as far as Billy's, but I've got just the same amount of people.

Lisa:

And just the same amount of sunshine.

Jeff:

And just the same amount. Actually, we have we have more sunshine because we've got the record for sunshine in St. Petersburg. So yeah. Um and and like Billy said, we have many services that we offer. And the last few clients that I've had literally were in tears after I got done helping them because they said before we stepped in and were able to help, um, they would sit in their place completely surrounded with the clutter, not knowing where to turn. And they felt like they had no help until they were introduced to our services. So the benefit that I get out of it is is yeah, it's it's my business. But I also I got into it because I wanted to help people and and help people that were vulnerable and didn't really have a place to turn. So for me, it's it's not only my business, but it's also kind of a ministry. My wife and I, who who own the business, have decided that we do it as as part of who we are, not just as a way to make a living.

Candace:

It's really fantastic. Yeah, that's why I love like one of people.

Lisa:

So okay, so if I was if I had a parent who had a hoarder home or even just a home, and I'm living in another state or or I don't have the availability to come, you would they would call you and you come and you assess the situation.

Jeff:

Yeah.

Lisa:

And but you guys, you also do um sales online. So you have the auctions with the things that people want to sell, so people could actually buy from other places because you can ship that, correct? Yeah, okay, so it's nationwide that these people can buy off. I know Candace actually bought a microphone not too long ago.

Candace:

I might be sucked into the auctions now. I could put the daily email.

Lisa:

It could be dangerous.

Candace:

It can it can be dangerous. I put myself I put myself a budget so that I don't get crazy. But yeah, some of the items can be shipped. Obviously, furniture can't be shipped. And what I really loved is afterwards, what didn't sell that was donatable, you guys also donate to local nonprofits for people that might need things. So that's another avenue of it as well. So if it doesn't sell, then they can also donate it.

Billy:

And they and you also bring in those dumpsters for anything that needs to be dumped and we try to keep as much as we can out of the landfill because there are families out there that don't have anything. Yeah, even half-used cleaners, like they don't have money to buy cleaning supplies. All of that stuff gets donated to families in need.

Lisa:

Oh, fantastic.

Jeff:

Yeah, we know that a lot of thrift stores right now have a really hard time with some of the larger furniture items, but I work with a couple of people that work through churches and local organizations with those uh families that are in transition, so that they'll actually come in as long as I've got it all kind of boxed up, they'll come in and just take it all to disperse to their families.

Candace:

So I want to add, as you said, transition. So we discussed my clients and the grandparents have passed away, but it's not just people who have passed away. You also assess like maybe somebody needs to go into a nursing home. And so now their house and their belongings need to be downsized, correct?

Billy:

Or even they're moving into an active community where they're they just want to be minimalists and move in and spend more time, you know, enjoying their later years. Um not their stuff. That's right. And so we can essentially downsize them. And um, but as you had mentioned, moving into assisted living, that's where our space planning comes in because they're typically in a 2,000 square foot house and they're moving into maybe a five or 700 square foot apartment.

Candace:

I I wouldn't know what to do. Yeah, I might need to hire you to downsize eventually.

Lisa:

But with the amount of purses that I like to purchase, I would need you guys just to assess my person.

Candace:

My husband won't let us get rid of our CDs because he says that's the next thing. Vinyls are really big now, CDs are coming back.

Billy:

DVDs are coming back, actually, because of the streaming services, the pricing's going up, so people are going back to DVDs, believe it or not.

Candace:

So, yeah, so my husband will let me have a closet full of CDs that we're not allowed to get rid of. So I will eventually lead him. I think we all do. Downsize my house. I think we all do. So talk about some of the other services that you guys do. We talked about downsizing, we've talked about cleaning out of houses. I know that there's a few other things that you guys do too that people might not think of.

Jeff:

So we can do everything from inventories. Um, I'm dealing with a client who they live in the north, and they had a person who passed away, and they needed to do an inventory for an attorney up there to handle the estate. So we can come in and do a complete inventory, take photos, uh, give them all the information, and that way it helps the attorneys to do that, and and they can plan for the survivors of the estate. Yes, ma'am.

Lisa:

Oh, I just had a thought. So you're saying that you're just doing an inventory for them. Um, could you do an inventory for people who are living here but they want that for insurance purposes? Absolutely. Yes. That that is fantastic because that adds to my list because so many people have lost everything in certain storms and things like that. Luckily, we haven't had anything this year, so things are much better. Woo-hoo! That's wonderful. But that is a great idea to say to someone, hey, look, for insurance purposes, because there's a number of people that the value in their property has gone up so much, but they have not insured their house for that.

Jeff:

Yeah.

Lisa:

And that's when or there's stuff that's in it that may have been flooded during the last storm.

Jeff:

Yeah, so they get full descriptions and photos of everything.

Candace:

Ah, amazing. Do you put it digitally then? So everything's like on a drive, or that's fantastic. Yeah, that's really great. I like you guys even more.

Lisa:

Okay, what else do you do?

Billy:

Well, I think one service that's near and dear to my heart is our charity estate auctions. So uh with with the nonprofits that we work with, some of the donations that go to them, they'll try to resell. So we can actually we can actually host a sale for them through our online CT bids auction. And when we do that, we actually do it, we donate a portion of our commission. Um, and the nonprofit gets essentially you know 100% of the sale.

Lisa:

That's amazing. That's amazing.

Billy:

I think that that's that and I work with a charity directly called um Safe Families for Children, and we work very closely. So they'll take a lot of the donations and then we'll donate employee time to essentially photograph and um load the items through our online auction CT bids, and then we'll run an auction for them so they're able to raise money for their foundation.

Lisa:

That's fantastic. That's good to know. Yeah, okay. Sorry. I just I like you guys a lot.

Candace:

So you got she mentioned earlier you guys are franchises. So in the greater Tampa Bay area, how many franchises are there that cover the territory?

Billy:

13. 13, and that's and that's the Tampa, St. Pete, Pinellas, yeah, uh Central Florida essentially, right?

Candace:

Does that go up to like Pasco, Hernando? Oh yeah, okay, perfect.

Billy:

Yeah, I've worked with all of those owners up there.

Candace:

Okay, perfect.

Billy:

So we've got we have we have um owners pretty much in every area, and then if we don't have an owner in that area, it'll go to the closest zip code or owner.

Lisa:

Nice. Okay, nice. Nice. I need to um get in touch with the people in Wesley Chapel just so that way I have a relationship with them because I feel like you know, we have a relationship now, which is wonderful, but even getting to know those people in your area, I think it's beneficial for just anybody to get in touch with caring transitions, just to have that relationship for when the time comes.

Candace:

I think this is a it's a great time of the year to be talking about this because we're it's gonna be the holidays and you're gonna be spending time with your elderly family members and friends. And maybe you can it's an easier time to kind of bring up these tough conversations when you're all gathered together. Like I know that when my grandmother, my grandfather passed away, and my grandmother was not doing as well as she should be, and she refused to move out of her 4,000 square foot house. Like it was tough conversations when my my aunts all got together and were like, we need to start downsizing now. She wouldn't do it. So we ended up, and I wish I would have, I mean, this was up in Maryland, but I wish I would have known about this organization then because they all had to come together on her basement. She was filled up with so much stuff.

Jeff:

Well, and the other benefit is because we're franchised across the nation. Within the last week, I've had two past customers that asked me, I've got a sister in Connecticut, I've got uh another person in South Carolina. Could you please find me, you know, who would be the caring transitions person there because of what I was able to do here? That's awesome. And they've made that referral. And and if we've got someone moving into our area, those franchises will work with us to transition the person at this end so that it's you're hand holding them from the first step to the last step.

Candace:

I love that. Wow. I really love that. And in our area, I mean, Florida is a big retirement area, so there's a lot of people that move here and retire here, but their families don't live here. So it is a lot that you guys take off of their plate if somebody does need to downsize or it's away. It's a it's a big piece of mind.

Billy:

And you're just working with the one company. Yeah, I think that's what they enjoy the most, is they're not working with three or four different companies. And having to coordinate all that. Yeah.

Candace:

Yeah. Yeah. You guys took care of like, because my clients were so far away that we had to have contractors come into and some other things done after you guys cleaned the house out. But it was nice to that you guys just took that, and then I I just stepped away. My clients just stepped away for the three weeks that that went on. That's right. And then we were able to come in and get the contractor and then a clean at like really like deep clean and get the house ready for photos. So that was it was because she had really had no idea when they were gonna be able to come over, and it would have sat on the market, like sat not on the market so much longer had you guys not been there.

Billy:

So I think that's the important part is that um the value is in the home, not necessarily the stuff in it. So the longer that it takes you to spend three weekends trying to do it yourself, you know, that's already a mortgage payment. That's utilities. So all of those bills add up.

Candace:

Yes.

Billy:

And and usually we can complete a project in 12 days.

Candace:

Wow. Yeah, they were it was amazing. Like you saw the pictures of it. I did, I just like I don't know how long this is gonna take. It's gonna take a really long time. And then when you said it was done, I was like, it was it was crazy. Yeah, yeah, crazy good. Crazy good. I was just gonna say that, reading my mind.

Lisa:

How to that? Well, you know what? Thank you so much, Jeff and Billy, for joining us today. Um, we're gonna make sure that we have especially your contact information, also just carrying transitions, have that information out there for everybody. Um, and we hope this episode gave some insight to you as a family member for people who are um maybe have somebody who will be transitioning soon. It might not be today, but it's definitely gonna be tomorrow. And we need to take care of our family members because it's so super important right now, especially with AI and people like I said, my mother getting scammed or people trying to take advantage of them. They they need to have people like you guys, and I truly appreciate you and I thank you for doing that and and being healers for people. So thank you so much. Oh, thank you. Um, Candace, anything else?

Candace:

No, I don't think so. Unless you guys have anything else to add?

Jeff:

No, nothing. That's great.

Candace:

So, this is a partnership that we have with you guys. We will add your contact information on the podcast description.

Jeff:

And if anybody has any questions, they can always reach either of us and and we can get them directed into the right uh franchise.

Candace:

We'll have that all that information on the on the website so that you guys they can contact you directly. So, yeah.

Lisa:

Thank you guys so much. Look, we're here, we're trying to make real estate simple, supportive, and fun again. Even if it's assisting a family member through difficult situations, don't hesitate to reach out. And we hope you have a wonderful, wonderful week.

Candace:

Until next time. Until next time. Take a deep breath, enjoy the journey, and know that we'll get through this together. Together, girl. Together.

Lisa:

All right, thank you.

Jeff:

Thank you.

Lisa:

Thanks so much for joining Snapchat's Tampa Bay. Hit subscribe to catch our latest episodes, and let us know in the comments what you want us to explore next. Keep loving the Tampa Bay vibes. See you guys soon.

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