Flipping Homes & Changing Lives: John McSherry’s Inspiring Story

Michael Stansbury (00:03.34)
Hello everybody, welcome to the Real Estate Pros podcast. I’m Mike Stansbury, with me today is John McSherry. John, originally from New York, now in Florida, how are you, sir?

John McSherry (00:17.203)
Very good, thank you for having me.

Michael Stansbury (00:19.054)
Yeah, John, good to have you here really quickly at Investor Fuel, the sponsor of our podcast. We help real estate investors, service providers, and real estate entrepreneurs, 2 to 5X their businesses to allow them to build the businesses they’ve always wanted and allow them to live the lives they’ve always dreamed of. John, always like to start off with this. When, at what point in your life did you veer off and go into real estate where you’re doing something different professionally?

Have you always been in real estate? What did that turn on the yellow brick road look like for you?

John McSherry (00:50.303)
Sure.

Sure, sure. Well, I actually got into real estate. I started learning and becoming obsessed with it probably in 2006. It was right after a series of events in my life. Finishing college, some family things that happened shortly after my father passed away. I was living in Philly, moved to New York to kind of have some big life changes. And that’s kind of when the obsession started. I was studying industrial design in college. So I studying product design and engineering. And after college, I was looking for a job in design. And at the same time, I was watching

TV and I became obsessed with HGTV and that’s all I would watch was Flipper Flop and House Hunters and all these shows and I was just so amazed by the design elements that went into creating a home, designing and selling and staging a home. So that’s really where the obsession started and then I started buying real estate in 2011.

Michael Stansbury (01:39.31)
Okay, so it started watching shows. Watching those early fix and flip shows on A &E. Did you ever see those as well? Yeah, yeah. Those guys I remember there was, I just remember for some reason, just came back in my memory. These guys in South Carolina and it was pretty wild that that show existed. But early on it was those shows that got you to

John McSherry (01:43.337)
Yeah.

John McSherry (01:47.997)
A few of them, yeah. Yeah.

John McSherry (02:04.469)
Sure.

Michael Stansbury (02:09.048)
think through, hey this could be a career. So that was your first purchase of real estate in 2011. Tell me about the first deal.

John McSherry (02:16.629)
Mm-hmm. Sure, so.

When I moved to New York or back to my aunt’s house in 2006, I actually moved into her garage because she had a half garage that was readily available. I didn’t have to pay rent. They gave me a place to go and start looking for a job in Manhattan. So that’s what I did. She lived in Long Island at the time and I ended up getting a job in Manhattan and I was going back and forth and I ended up staying with her for five years and saved every single penny I had. Saved up about $90,000 from that job that I had and I ended up buying a condo in Lindbrook, Long Island.

And shortly after buying that condo and moving in, I found out about a Rich Dad Poor Dad event in New York, in New York City. And I went to that event and I was like, man, I just spent five years living in a garage to save for this house when I should have been out buying assets. So I’m gonna sell this condo and I’m gonna go out and start flipping houses. So that’s what I did.

Michael Stansbury (03:10.86)
that’s hilarious. So you pivoted. so that what’s great about that, and this is really good tidbit for people that are listening is you got new information and you took action on it. And Robert Kiyosaki, he’s one of those folks that in that book specifically is the boomerang book that people go back to. They reread it and starts it. It really starts people down a path. But some people aren’t.

action takers but you took action so you sold it and then you’re like okay I buy I gotta I gotta figure out this part and tell me what did what did that look like

John McSherry (03:45.312)
Sure, so.

I sold that condo and funny enough, I actually started buying and selling subway franchises in 2012, but it wasn’t for me. So I was like, this, don’t want to be in the restaurant business, but it was kind of like low hanging fruit. Right. So I inquired probably like four years prior and then they got back to me and they’re like, you can start buying franchises now. And I was like, okay, great. But then once I got into it, I was like, this is a nightmare. And I knew exactly what I didn’t want to do. So ended up selling those. And then around 2014, I decided to get my real estate license. So I sold that condo.

And then I started looking for flips in 2015 Well, the main thing that I should mention is that I was telling everybody what I did and what I was looking for my family my friends social media and at some point my aunt said to me Hey, I have a friend whose father needs to sell his house. It’s a distress situation The house is in disrepair. Do you want to take a look at it? So it’s perfect timing It was right after I sold everything and I took a look at it and I ended up buying it for 305,000 I was able to put 5 % down I bought it as a primary because at that time I was renting

I sold my condo and bought that with $15,000 and then I paid for the renovation in cash. So I ended up selling it for $550,000 and made $150,000 on that flip and it was my very first flip deal. So it was pretty impressive. It felt great, but you know what’s funny? It felt great, but I was still full of fear and I still kept working at my job at a fear that I would never be able to do it again. So that was something I had to get over. Yeah.

Michael Stansbury (04:59.052)
How’d that feel? How’d that feel?

Michael Stansbury (05:07.854)
Oh, yeah. It is. It made it real, right? You had 150K that you didn’t have, but you still have this residual fear that we have. I’ll never forget, so I have a company, I live in Memphis, and I fix and flip and wholesale and do some things in Memphis. The first time I ever wholesaleed a property, I did it by accident. So.

John McSherry (05:17.087)
Sure.

John McSherry (05:22.611)
Right.

John McSherry (05:27.865)
cool.

John McSherry (05:31.465)
Nice.

Mmm.

Michael Stansbury (05:35.182)
And what happened was is I got this house at a really great deal. was, it was very early on and I was just moving some stuff out of the house. I was doing the cleanup by myself with a crew and another real estate investor who ended up being a friend of mine drove by and said, Hey, are you, are you, do you buy this house? I said, yeah. He goes, are you flipping it? I was like, yes. He goes, well, uh, I’m, got to flip down the street. I paid such and such for this property. said, Oh, that’s okay.

And I just kind of did that. goes, how much did you get this for? And I told him, and it was about $70,000 less than what he paid. And so he was like, I’ll give you $50,000 if you’ll let me get that contract. he basically gave me a $50,000 whole selfie. And I thought, well, that was awesome. That’ll never happen again. That’s kind of what I thought because

John McSherry (06:06.453)
Hmm.

John McSherry (06:30.013)
Mmm. Mmm. Right.

Michael Stansbury (06:33.366)
I just never done it before. just got lucky. But you can end up making a business out of it. So you kept your full time job and what were you doing at the time? The full time? Was that still Subway?

John McSherry (06:35.285)
Sure.

John McSherry (06:40.181)
100%.

Mm-hmm. I no, so I sold those and then I was doing design work. So I ended up getting that design job in 2006, changed jobs a couple times and I was working in packaging and product design. So I was designing packaging for toys, for fashion, for a few different companies throughout Manhattan. Yeah.

Michael Stansbury (07:01.324)
Yeah, and you kept that gig until you got your next one?

John McSherry (07:06.069)
I actually kept it until 2018. So I kept juggling everything and it was just, it was so fear-based. And it was all a mindset thing. And it wasn’t until I made that jump in 2018. even after I quit my job, I still kept dipping my toe in the water. Like I was taking these little freelance design jobs for like designing packaging and graphics and websites.

Michael Stansbury (07:25.346)
kept reeling you back in.

John McSherry (07:26.805)
Right, right. And then I went to a Tony Robbins event in 2018, Unleash the Power Within. And at that point, I made a clean break. I was like, I’m not going back into this. I’m staying in real estate. I’m staying with my passion. And I decided to go all in on the flipping and the real estate brokerage. So, but yeah.

Michael Stansbury (07:41.774)
And so now fast forward to today. Tell us what is the super power that you have now? How are you helping people the most in today’s market?

John McSherry (07:56.096)
So it’s funny you say that. like a lot of what I went through.

early in life, you know, after my father’s death and it really put me in a bad place and it actually created something really powerful. And I’ll just touch on that real quick and how and how it pushes me to serve people. So, you know, I was 26 years old, pushed me to a bad place, basically became an alcoholic, was drinking super young, lost my license, had nothing. And I was looking for that job in 2006 and I ended up going into a 12 step program and that 12 step program taught me a design for living because at 26 years old, right. So, so I’m 44 now.

but at 26 years old, I didn’t know how to live. And after losing everything, my father, I felt like I really didn’t have much to live for and I was really in a bad place. That program put me into a place where…

As part of program, you have to go out and make amends to everyone in your life, right? So it releases guilt and shame. You have to go out and serve other people on the deepest level possible. Share the book of Alcoholics Anonymous with other alcoholics. I was going to jails, rehabs, and I was getting rides to get to these places because I didn’t have a car. So what that has taught me was the power of empathy and building relationships, right? It taught me how powerful that was because the more people I helped, the better I got, right? Because now you’re serving other people. So whatever is in your head, your ego,

whatever pain you’re dealing with, you can’t really think of it because now you’re thinking of the next person, right? So it puts you in a place of serving. So for me, I feel like having the hardest rock bottom of my life, right? Turned out to be the biggest blessing and has allowed me to see the human dynamic and relationships from a whole different perspective. It’s something that’s still staged with me today. I don’t really go to meetings as much as I used to, but I’m still involved and I still find ways of serving people. It’s really interesting. It’s like you learn the more people you help, the more money you make and the more

John McSherry (09:42.427)
money you make.

you the more people you can help. So to me, I consider that as unfair advantage, the ability to to feel what other people are feeling and to really empathize and to really, you know, really hone in on relationships and serving other people. Because when I go into a house and say, listen, I could buy the house cash right now, right? You could just walk away, lock the door. The house isn’t disrepair, it’s not mortgageable. Or I could help you renovate your house. I could recommend contractors. Or three, the house isn’t so bad, I could put on the market because I’m a broker and maximize the profitability.

So it’s really coming to every situation from a problem-solving perspective and just to serve your clients. And to me that really became, I believe, my unfair advantage.

Michael Stansbury (10:24.04)
So you using the that you know the valley as the event in your life and that is what that that it was drives your purpose now that you understood how to operate with maximum efficiency and that is by not thinking about John McSherry is thinking about that person as a human being and how can you solve their solve their problems that’s that is that is awesome and it’s a great it’s a it’s a great

John McSherry (10:33.429)
correct.

Michael Stansbury (10:52.29)
you know, redemption story and the fact that, you keep that like right in front is, is why you’re, you’re probably doing as well as, as you have, cause you know, you know who you are. So that’s awesome. And so, you know, now you’re, you, you’ve been in New York and a New York sounds, I have interviewed some New York realtors, some New York investors, and it just sounds hilariously funny. And of course,

John McSherry (11:03.551)
Thank you.

Thank you.

John McSherry (11:13.546)
Mm-hmm.

Michael Stansbury (11:19.922)
I, yeah, everybody’s familiar with the president of the United States and Donald Trump and we’ve all followed, we all know what his exploits are in New York. It just sounds like a different animal than, you know, regular real estate. So how did you survive that, the concrete jungle of New York? What was that like? and do you still, yeah, do you still operate in New York? What does that look like?

John McSherry (11:32.319)
Hmm.

John McSherry (11:36.511)
Sure.

John McSherry (11:40.894)
I do. So sure, it’s funny when they say if you can make it there, you can make it anywhere, and it’s really true. feel like New York created me on top of finding sobriety and finding this design for living.

looking for work in New York City, all the competition, then getting a job and then getting into real estate in New York City and Long Island with some of the fiercest competition. And if not, the world really teaches you a lot, right? It teaches you also like how to fail forward, right? And to accept rejection and to keep pushing forward, right? Whenever you’re cold calling, because that’s really how I cut my teeth in the business. It was cold calling, obviously building relationships and serving people. But, you know, it is difficult, but it’s a place that you could really make a great business if you’re doing the right thing.

build a great reputation because your reputation is everything. If you just keep working on it slow and controlled eventually you start to make it and you start to do things. It’s just that a lot of people they give up they give up way too soon. You know it’s

Michael Stansbury (12:42.734)
The ability for somebody just to, especially in the high pressure situation that you have in New York City, just to, I mean it’s high pressure, life is tough.

But it just seems like whenever you add in the mix that you have that many people on that small of an island doing all the economies, the economy of scale that you’re having, it seems like that is not just a pressure cooker, that’s a high pressure cooker. And to walk through that and have some success is a banner basically for most people, because most people can’t handle that kind of pressure.

John McSherry (13:24.209)
I agree. It’s something that, you know.

It’s kind like what they say about New Yorkers as well. It’s like people always think that New Yorkers, you know, don’t care or they’re rude. You know, the fact is that they really do care. You just have to really put the work in to get to know them. So New York really does have a very hard like shell, but once you kind of break into it, it starts to be like a little community. for me though, I cover a lot of New Yorker cover from New York City all the way up to Montauk. So I cover Long Island, Brooklyn, Queens, and you know,

it’s something that even though I’m here in Florida and it’s funny that I’m actually building a lot of recent New York business because I have a lot of past clients. I’ve been doing a lot of mailers. So even though I’m here in Florida and I do go back and forth like 50 50 my New York business has taken off even more. And it’s interesting because just to get specific about the market right now in New York the inventory is so tight and like people have to be there for jobs for schools and so forth. So that’s always a good market. And right now the prices are

still climbing, the interest rates are still really high. But as in Florida, like South Florida, and even parts of Texas now, the areas that really exploded the most are now starting to kind of calm down, you know, the most. for me, I do like being in multiple markets and being diverse, multiple businesses, right? So I’m a real estate agent and a real estate investor, but I’m also in New York and Florida. So it kind of gives me that diversity. I usually don’t recommend that, but for me it works because I’m in both areas and a lot of New Yorkers do buy in Florida. So for me, it’s a perfect combination.

It’s not like I’m doing New York and Memphis or you know like you know Florida and LA. It’s like New York and Florida go together so well. So it actually works perfectly, you know.

Michael Stansbury (15:07.086)
They do, yeah. Yes, so the, you know, it’s always.

You know, it’s known, I’ve been in real estate for a while, but it’s known that a lot of people from New York, from New York state and from New York City have a place in Florida. They escape sometimes the winter for a little bit. And then the folks from New York, when they want to retire, where do they go? They go to Florida. And that’s where my actually, and you know, I’m from Memphis. My mom went to Florida to retire. I’d like to go to Florida to retire. And it’s, yeah, it’s great. I’m coming.

John McSherry (15:29.322)
Exactly.

John McSherry (15:34.877)
cool. You should. Let me know when you’re ready. Yeah. Yeah.

Michael Stansbury (15:41.122)
You know, what’s interesting about Florida too now is yeah, the markets, there’s some areas that are, that are a little bit softer, but the, the long-term for Florida, if they get the, you know, I just, and again, you correct me if I’m, you’re in that market, but I was just there about a month ago and I was in Fort Lauderdale. I was there for a week and I rode the bright line to, from Fort Lauderdale all the way up through Miami to I think West Palm. And then I looked at their plans and that’s, you know, the plans for the

John McSherry (16:05.812)
Hmm.

Michael Stansbury (16:09.934)
the rail is pretty cool, they’re gonna go across Florida, not just north and south. Yeah, and to Tampa, and that’s super cool. So even though Florida has its issues right now with the insurance and the inventory and maybe a little bit overbuilt, I still am very, very bullish that those problems will solve themselves. But yeah, so with that being said, are an investor, are you…

John McSherry (16:12.787)
Yeah, to Tampa.

John McSherry (16:25.663)
But soon.

Michael Stansbury (16:36.3)
Are you mainly right now wholesaling and fixing flipping in Florida or tell me what that part of your business looks like?

John McSherry (16:42.133)
Sure, sure, we have this new company called Smile Homebuyers and it’s a wholesaling company at the core but…

You know, we are really a marketing company. So whatever deals we come up with, we may choose to flip it, redevelop it, knock it down and develop it. It really just gives us those options. We’ve really perfected and become a world class wholesaling company. When my business partner, James, moved down to Tampa, I saw an opportunity that was about a year ago and I’ve been wholesaling for a very long time. And so as he, we decided to combine efforts because I was going to make my way down to Florida as well. And we started in Tampa. We saw a tremendous opportunity to where we’ve become one of the top wholesalers.

companies in Tampa. We’re doing about two to five deals a week. That’s wholesale flipping, burst strategy, redevelopment, and we’re raising a lot of capital for upcoming development projects and multifamily projects. So Tampa became our primary focus and then we brought it over to the East Coast because I’m here. We opened up an office in Fort Lauderdale and we’re growing that team as well and we’re still kind of just hitting those two coasts and it’s been going really well so far.

Michael Stansbury (17:46.19)
Alright, so that’s a lot of growth in a short period of time. Like, what does the team look like today?

John McSherry (17:48.906)
Yeah.

Hmm, sure. So it fluctuates a little bit, right? Because we’re always hiring and firing, but our core team is probably about 10 people. It’s acquisitions, dispositions, lead manager. I brought over my COO from my real estate, my whole real estate company. She’s come over to help operate the wholesale company and she kind of helps with like the day to day. I have my business partner and I, and then we have a bunch of cold callers. So we’re really just always testing and trying different software. We’re doing everything from, you

pay-per-click so PPC PPL we’re doing we’re pulling a lot of data text messaging cold calling still doing some mailers to some highly motivated sellers so we’re doing whatever we can to really get in touch with motivated sellers yeah

Michael Stansbury (18:32.771)
Yeah.

So inbound and outbound, do you have a preference as you’re looking at your data, over the last six months, what has been more profitable for you or where most of the leads, the good leads come from, your inbound or your outbound marketing, would you say, John?

John McSherry (18:50.453)
Great question. the inbound, the pay per lead has been the most effective and the joint venture. So we do a lot of this a lot of dispositions for other wholesalers. We actually almost became kind of like a disco house in a way to where now our ability to to market and find buyers has been really efficient. We’re able to get great prices and we’re able to serve a lot of people pretty quickly. You know, we use Investor Lift and other other sites to find their cash buyers. We pull out of data. We have teams just working on pulling data.

everything from just you know different lead sources you know Facebook and whatever we can to just find the opportunity and help other people so we’ve been able to sell deals very quickly so if anybody ever needs help selling a deal definitely let us know yeah and we can move it very fast

Michael Stansbury (19:31.072)
If they acquired something. Yeah, yep.

Yeah, that’s a great, that is just a really great thing to have is be the best at that. And then the wholesalers, the ones that are hungry and that get a deal, we want to close fast, right? We want to make sure that we can execute on the contract. And so that’s a really great thing to have in the marketplace. Well, John, what else? Let me ask you this. are you…

John McSherry (19:42.484)
Right.

John McSherry (19:49.685)
Correct.

John McSherry (19:58.326)
Sure.

Michael Stansbury (20:02.734)
You’re in Tampa 50 % the time, New York 50 % of time. What does your life look like outside of real estate? What kind of hobbies do you have, family, what is, yeah, tell me about that.

John McSherry (20:12.671)
Sure, sure,

Love to stay pretty active, working out and all and I want to get into pickleball. I know that’s the new craze so that’s something I want to get into. My partner is like insane about it. He loves it. Something else and you know I have an 11 year old son. Well he’s actually turning 11 in two days. Thomas. So he’s like just everything to me. I actually shoot a lot of content with him he’s great. So it is a little challenging traveling around but you know we do whatever we can to make it work and we’re just really trying to build this business and build build wealth long term.

Michael Stansbury (20:20.194)
Yeah, it is.

John McSherry (20:46.067)
And yeah, and then most of my family lives in New York, but I have a lot of family down here in Florida too. So a lot of people I know are moving down here. We actually have some new acquisition guys and new money raising guys that are gonna move down here right like within the next month from Long Island. So we’re doing what we can. And now I’m actually in Fort Lauderdale or close to Fort Lauderdale. My partner James is in Tampa and I just go back and forth to Tampa and then back and forth to New York. So it’s a little challenging, but we’re in just like a heavy growth mode right now. So it’s a little crazy, but I’m looking for

it to things calming down once we have more systems in place and you know we’re implementing more software. We’re creating Smile Home Buyer software as well so that it could be used by our team. Also we may actually sell access to it as part of our training potentially. And we’re just doing whatever we can to make it easier for the people that work for us in order to get the leads, get the CRM, get the follow-up and get things moving. So

Looking forward to things to calm down a bit more so I can focus more on family, for sure. Yeah.

Michael Stansbury (21:43.726)
Yeah, yeah, well, we’ll keep making hay right now. Well, John, where can people find you on the internet, social media? Where’s the best place for, if people were saying, know, I need a deal in New York or I need a deal in Florida and want to deal with you, let our audience know, where can they find you at?

John McSherry (21:48.937)
For sure.

John McSherry (21:52.458)
Mm-hmm.

John McSherry (22:03.189)
So I think best is my Instagram because it’s kind of like a visual storyboard of what I’m doing and I try to be very transparent. I’ve been doing it for over 10 years, really just documenting my journey. So you can follow me on Instagram. It’s my name, John, J-W-H-N dot Mick Sherry. That’s M-C-S-H-E-R-R-Y.

Michael Stansbury (22:21.664)
Okay, well folks, you have it. We’ll put that information in the show notes, about John’s Instagram so you can see that. John, thank you for being part of the Real Estate Pros podcast. We appreciate your story and a really great, redemptive story, folks, if you find yourself in a situation like that, I really would love for you to just reach out to John. He’s probably a guy that if you’re in that position, he’s a guy that will help out.

And we appreciate your time and thank you for listening to this podcast, folks. We’ll see you next time. Remember, like and subscribe and do all the things that all the podcasters and all the Instagram and all the content creators tell you to do on this, folks. I appreciate your time and we’ll see you next time.

John McSherry (23:08.053)
Thank you.