sean: tonight, on the deed chicago, an ambitious go-getter... robin: i made a lot of people a whole lot of money. sean: ...wants to make a killing on vacation rentals. laura: my nightly rate brings in $30,000 a month. robin: this is exactly what i want to do. sean: but is she trying to do the right thing... [crashing sound] robin: woo! oh my, oh my. sean: ...with the wrong people? sean: you're the contractor? q: yes. that's what they call me. inspector: the stairs aren't to code. the headroom's not to code. sean: he's definitely bull [bleep] us. sean: she's in way over her head. robin: this is out of control. sean: but if i can get her to take charge... sean: i'm obviously here to see what the hell's going on. sean: ...her dream of becoming an airbnb mogul... sean: oh-ho-ho! sean: ...could become a reality. sean: this is phenomenal! narrator: he may have been born in ireland,

but sean conlon was made in america. sean: i have lived the american dream. narrator: he's built a fortune in the hardnosed world of chicago real estate. sean: i came here with $500 in my pocket, and i worked as a janitor. i shovelled snow. i cleaned toilets. i did anything i needed to do to scratch out a living. narrator: at night, he started to sell real estate. sean: after i got my first commission cheque, i realized i was never going back to my day job. narrator: and by age 26, he was one of the top-earning brokers in america. sean: i have bought, sold, and flipped billions of dollars of real estate. there's nothing more exhilarating than taking something that's tired and rundown and breathing new life into it. narrator: now, sean's looking out for the next generation of developers. woman: we need help. sean: there's no crisis we can't handle. narrator: investing his own money... sean: so what's your ask? man: $2 million. narrator: ...and years of experience... sean: you'll see how it should be done. narrator: ...to help them create great real estate...

sean: it's spectacular. woman: wow. this is beautiful! narrator: and their own success stories. nick: you've helped me save this. sean: all right! caren: thank you. narrator: this is the deed: chicago. ♪ sean: 47-year-old robin carter spent the past two decades in corporate sales, repping one of the biggest soft drink brands in the country. robin: i love to sell, and i made a lot of people a whole lot of money. sean: but last year, robin was laid off. instead of looking for another job, she decided to use her severance money to invest in her dream career: real estate. robin: i think about people like warren buffet, berkshire hathaway. [laughs] you know, most of your billionaires, they started out in real estate. you got to take a leap, and that's what i decided to do. sean: six months ago, robin purchased this 19th century greystone in woodlawn, on chicago's south side. not only is it right next door to where she lives now; she got it for only $88,000, with high hopes of turning it around.

robin: when i walk into a place that's been rehabbed, that's super exciting to me. that makes me smile. i'm a before and after girl. sean: but what robin struggles with is everything in between. because now, four months into the reno, she's finally realized the budget she set is nowhere near enough. robin: i'm not 100 percent really mapping out how much a project costs. i'm gonna be like, "oh, shizzle," you know? [laughs] red alert. ♪ sean: about ten miles from downtown, woodlawn is one of chicago's hottest real estate markets. so the fact that robin got a historic greystone for such a steal means that it could be a great investment. robin: come on in. sean: okay. obviously you've started doing some work on it. robin: i have. we're framing. sean: the ceiling heights are great. it's bright as hell. robin: yeah. sean: you're probably thinking, like, white, white walls, dark floors. robin: i am, yep. white, or... sean: that's very cool. robin: ...light grey, which is the new white. sean: okay. will you keep the window, or... robin: i am planning to keep the window.

sean: okay. robin: yep, the stained glass. sean: it's wonderful and traditional. robin: yeah. this is my living room, dining room area. sean: okay, yeah, perfect. robin: yep. sean: and then, so back here, what have we here? robin: so, this was a change that was just made today. sean: okay. robin: this was the bathroom. sean: alright. robin: we're gonna move the bathroom. sean: okay, why? robin: we want to open up the property even more, so you can see it from front to back. it'll help from a lighting standpoint. sean: okay, yeah. makes sense. robin: people love open floor plans. sean: i get it. robin: yeah. sean: it makes it wide open. robin: yes. sean: would've been nice to make that change a couple of weeks ago, right? robin: absolutely. sean: just a little expensive to take down your framing. robin: yes. sean: i really like what robin has planned. if she moves that bathroom and tucks it away by the stairs, she'll have a bright, open first floor with a huge living space that flows into a large kitchen at the back of the house. it's the perfect floor plan for entertaining. robin: this is coming off. sean: so you'll have steps here? robin: we will have a deck here. sean: and this beaten-up old porch? she plans on demolishing it to make way for outdoor living space. sean: it'll make for a nice yard, then, with a deck, right?

robin: and a deck, yes. sean: very cool. robin: yeah. sean: and what's going on here? robin: they're rehabbing this house next door. sean: oh, that's cool. robin: so, good timing. i'm excited about that. sean: yeah. robin: 'cause when it's time to sell it, that'll be fantastic. sean: having the house next door being renovated for sale is even more confirmation that this neighbourhood is on the up. but it is important that robin beats them to the market. sean: hmm. okay. so, this is the master bedroom. for a row house, it's actually wide. robin: yeah. it's sizeable. sean: but row houses can be dark, so i really want robin to bring back this original skylight. sean: anywhere you can get extra light from, it makes a big difference. robin: yeah. sean: aside from the master bedroom and en-suite bath, the rest of the top floor will have a laundry room, two additional bedrooms, and another bathroom. sean: right, let's take a look at the basement. robin: awesome. sounds good. sean: okay. so what are you doing down here? robin: um, so what i'm gonna do in here, there's gonna be a front room... sean: yep. robin: ...actually down here, so for lounging. then you'll have a bedroom, a laundry room, a bathroom,

storage along here... sean: have you thought about somewhere where you'll put a kitchen? might you put a small kitchenette against that wall over there or this wall? robin: i hadn't had that built into my original plan. sean: right. sean: if robin builds a kitchen in the basement and puts in a separate entrance, this space all of a sudden becomes a standalone apartment. buyers are sure to see the potential of rental income as a bonus. but it will mean more work, and i want to make sure that q, the contractor that robin has on the job, is up to the task. robin: hey, q, how are you? q: good. how's it going? sean: nice to meet you. q: pleasure's mine. sean: how are you? q: good, good, how are you? sean: you're the contractor? q: yes. that's what they call me. sean: and how do you guys know each other? q: uh, we met in the coffee shop. robin: yeah. somebody told me he did a fantastic job from a gc perspective, and it's been great. sean: so how did you start contracting? q: i started about 27 years ago. sean: okay. i like that. what else are you working on?

q: i'm working on a couple more projects, uh, on the west side... sean: okay. q: ...and on the south, near south side here. sean: q has several jobs on the go, and that means robin is really going to need to stay on him to make sure that this job doesn't get lost in the shuffle. sean: i wanted to ask you about something back here, q. i had noticed that there's a... see this, right? q: yes. sean: it's pretty slight, but obviously it's structural. it bows to the centre, right? what are you going to do here? q: we're gonna actually take this out. sean: yeah. q: and re-brick it, re-shore it up, and get it level. sean: what do you think this will cost extra? q: we estimate 7 to 10,000. you know, we never know what's gonna come down when we start moving it. sean: right, right. all right, so you borrowed $140,000 to do the renovation. robin: yeah. sean: do you think that's enough? q: no, she'll definitely need over 140,000 to finish this renovation. sean: okay. robin: yeah, we're probably looking at anywhere between 40 to 60, give or take. sean: so, potentially $200,000 total. robin: exactly. sean: when do you think you'll be finished the house?

q: we figure about 90 days. that's based on city approval. the city inspectors sign off on everything. sean: considering what's left to be done, 90 days seems just about right. and that means robin's house will hit the market in late spring, which is a real sweet spot for selling a home. sean: so you're renovating this to sell. robin: i'm renovating this one to sell. fix and flip, yep. sean: okay. robin: so then, in addition to this property, i'm also working on a property in north kenwood i'm moving into. sean: what do you plan to do with your home next door? robin: so, my house next door... sean: yeah. robin: ...i'm planning to airbnb it. sean: okay. sean: no one could ever accuse robin of lacking ambition. she's fixing to flip this place, will use her current home next door as a vacation rental to generate income, and she's renovating a third house that she plans to move into. sean: so that's a lot of moving parts. robin: i mean, it's a costly equation. sean: does it keep you awake some nights? robin: 5,800 is what i pay on mortgages alone for the three properties. sean: okay, wow, wow. robin: right, so that's a substantial amount. sean: okay. so what do you realistically think you can sell it for?

robin: i think i can sell it for anywhere between 4 and 415. sean: i'm impressed. let me noodle your request... robin: okay. sean: ...and i'll be back to you, okay? robin: okay, sounds good. both: thank you. sean: right now, woodlawn is going through a major transformation. the university of chicago is expanding their campuses here, and renovations like robin's are attracting more affluent buyers. sean: plus, the comps tell me she could easily sell her place for the $415,000 she wants and walk away with a potential profit of around $120,000. that's an incredible win for a rookie. ♪ sean: well, thank you very much for coming. good to see you. first things first. i really like the fact that you're... reinventing yourself. robin: yeah. sean: sometimes i think i'd love to reinvent myself... robin: [laughs] sean: ...but down the road. robin: yes. sean: so let's say, hypothetically, i lend you the money to flip this property... robin: i think i want to keep that property now.

it's two separate units. so i have the ability to lock off both of those units and actually have two different rental situations going on at the same time. i cannot do that in the property that i'm currently in. sean: have you a handle on what rent you can get? robin: um... it should-- it should work out well. sean: so we're changing the whole game, right? robin: mm-hm. sean: so it's not a flip. it's become somewhat of a backflip, right? robin: [laughs] that's a good one. sean: just so we're clear, you would still be borrowing the money to finish your present project from me. robin: and actually sell the property that i'm currently in. i owe about 220 on that particular home. if i sold it for 400, i would get a profit of 180. so there's actually more money in the house that i'm currently in. sean: so then you would pay off the loan i would give you when you sell the property next door? robin: correct. sean: as much as i don't like being blindsided mid-deal, what robin is proposing is actually much better for both of us.

she'll end up with a bigger profit by selling the home that she's currently living in. and that home can go to the market much sooner, and that means i get paid back much faster. sean: you wanted how much from me? robin: it was 64,000. sean: i'm going to give you a one-stop solution for everything. robin: mm-hm. sean: i will actually give you $275,000. it takes out your current lender. robin: mm-hm. sean: i will give you the 64,000 to finish the construction. you'll be paying 14 percent on that money. and i will take 20 percent of the profit. sean: and i would want to reserve the right to replace q if he doesn't perform per contract. that's my proposal. robin: i feel really good about q. i plan on working with him on other projects, so i have an issue with that particular point. sean: the general contractor gets paid for his construction. robin: mm-hm, right. sean: as the lender, your interests are perfectly aligned with me if i lend you this money. sean: q's are not. robin: right. that's fair. so then...

14 percent interest. i was thinking more of eight points. sean: if i had your situation right now i couldn't get an eight percent mortgage, okay? robin: uh-huh. sean: you have three mortgages, you've two construction projects going, and you don't have a job. robin: right, right. that's correct. sean: so, how about... i'll do 12 percent. robin: okay, i like that. that works for me. sean: you win there. robin: and we keep q? sean: you have to remember, me giving you this money, i would be investing in you. so i have to trust that you know what you're doing. robin: okay. sean: do we have a deal? robin: i think we have a deal. sean: okay. robin: alrighty. thank you. ♪ sean: i've done a deal with robin on her greystone reno where electrical and hvac are being installed. the plan is to build two separate units that robin can rent out through airbnb. chicago is the third most profitable vacation rental

market in the country, right after san diego and miami. but not all rentals are created equal, so i'm taking her to three different units, at different price points, to show her how to maximize her profit. robin: wow! this is beautiful! man: come on in. robin: thank you for having us. man: sure, of course. robin: this is awesome. wow. woman: come on in. robin: oh my gosh! sean: wow. this is rock star. uber urban. robin: i love it. sean: these properties are some of chicago's most successful airbnb rentals, and i want robin to see what makes them better than the rest. sean: i like it. woman: so i have a fully-stocked bar for all of my guests. sean: look at this. laura: if they finish a bottle, they replace it with another, so they sort of restock the bar for me. sean: i like the subway tile. man 2: i wanted the kitchen to feel like you're in a restaurant. sean: okay. so really good for entertaining, right? man 2: it's fantastic. woman 2: absolutely. sean: oh, this is cool. woman 2: the unique pieces... robin: yeah.

woman 2: ...are what brings the whole place together. sean: unique touches and vintage furnishing will definitely woo higher-end clients, but robin also needs to understand how to get top dollar without breaking the bank. robin: so i love the way you have it furnished. man: i got the furniture completely off of online websites like craigslist, letgo, offerup. robin: wow. laura: when you're doing a vacation rental, for every extra guest you have past a certain number, you charge an extra nightly fee. so wherever you can put in more beds... robin: yeah. laura: ...do it. sean: so let's say i call up. man 2: yeah. sean: i want to rent your house. man 2: yes. sean: how quickly would i hear back from you? woman 2: less than a minute. robin: wow. man 2: response time is critical. sean: if robin follows these tips, she could turn her two units into serious money makers. sean: say you rented this home for one year, right, to somebody? how much would that rent out for the year, would you guess? man 2: i would guess... close to $40,000. sean: okay, so this would rent for $40,000 per year. man 2: for a full-time rental. sean: for a full-time rental. so airbnb? man 2: um... woman 2: double that. sean: okay, so you'd double it. man 2: yeah.

man: if it were rented as a single-family home, i would expect to get, hopefully, 3,000. uh, with the vacation rental, 7,500 to 10,000 a month. sean: okay, so double-triple again. robin: i like it. okay. sean: if you were going to rent this apartment just for the year, what would you charge per month? laura: i would charge $3,000 per month. sean: but, doing what you do, the vacation rental model, what do you charge? laura: well, the nightly rate brings me in about $30,000 a month. sean: wow. laura: so 10 times what i would normally make. sean: that's unbelievable. robin: ah, yeah. this is exactly what i want to do. you've changed my life, laura! laura: [laughs] sean: mine too. i'm going back to the office and i'm selling everything. [laughter] robin: airbnb it all! sean: definitely in the wrong business. laura: [laughs] sean: these potential numbers are astounding, but vacation rentals can be risky and not everybody's going to make $30,000 a month. but after hearing these figures, i am confident that if robin gets her units rented, she can cover her $2,000-month mortgage and then some.

sean: oh-ho! robin: oh my, oh my. sean: there's a lot of bull [bleep] here at this stage. we need to get it done. robin: absolutely.

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[crashing sounds] sean: woo! [crashing sounds] robin: oh my, oh my. [crashing sounds] robin: wow. [construction sounds] sean: oh-ho! there it goes! sean: okay, guys, well, i just wanted to catch up on our schedule in here. so, obviously, q will be able to enlighten us a little bit on the inspections? q: we haven't scheduled them yet. we won't schedule them until we have a completion. that way we make one phone call and it's done. sean: there are two ways to handle inspections-- book them, then work backwards to the date and make sure that all of the work is done. and then there's q's way-- do all of the work and then try and get the inspections booked. it's risky because it could take the city weeks to get out to the site. but i have to assume that q has it under control

because he has lots of projects in the neighbourhood. sean: okay, it would be wonderful if you could keep it on track, right? schedule-wise? q: yeah. robin: that's the plan, yeah. sean: schedule is something in your flipping career that you're gonna have to start to pay real close attention to. robin: absolutely. yep, yep. sean: very important. robin: yeah. sean: because then you're going to start selling next door soon, right? robin: yes, yes. so next door, we'll start selling it-- it's supposed to go on the market in about three weeks. sean: okay. robin: if you think about q's timeline and my timeline... sean: yeah. robin: ...it's really coinciding and working well. sean: it could be perfect. robin: absolutely. ♪ sean: robin lives right next door to her reno. since selling that property is how she's going to pay me back for the loan, i want to see how much work it needs before we can list it. sean: i'm going to look at it like i would as a salesperson. robin: got it. sean: so first things, the kaleidoscope of colours is very pretty... robin: yeah. sean: ...but it's very personal. that's your taste. robin: yes, okay. sean: i'm going to say you'll need to paint this neutral. the other thing, your furniture's very big.

robin: okay. sean: and so, you may want to store it... robin: yeah. sean: ...sell it, whatever you choose to do. sean: we might decide on a little staging. robin: yep. sean: but whatever you do, make space in here. sean: okay, now, the good news is your kitchen looks like it'll be okay. i think if we cleaned it up... robin: okay. sean: ...and polished it and stuff, it might be okay. robin: great. sean: you've got a lot of stuff. robin: i have a lot of stuff in here now because i'm moving. so i'm just storing it here right now. but this is really kind of a breakfast nook area. sean: but when we start showing... robin: yes. sean: ...we definitely need all this to be gone. robin: oh, yeah. this will be gone. sean: i mean, all this has to be addressed here, right? sean: robin's home needs decluttering, plaster repair, restaging with smaller furniture, and a new paint job from top to bottom. but if she puts the work in now, it should ensure a quicker sale. sean: it's an investment. robin: yep. sean: you'll get it back. robin: yep. sean: we have a plan. robin: sounds good. ♪ ♪ sean: while the crew is working to restore

the original brickwork on the exterior, robin and i can focus on her interior finishes-- specifically, the kitchen, since she wants the entertaining area to be a draw for people looking to airbnb it. so we will need cabinets that will look great in the listings photos and withstand a ton of wear and tear. sean: this really works. robin: and it's clean. sean: i really like it. robin: it's a good look. sean: do you think it'll be in your budget? robin: yeah. sean: it's perfect. sean: up next, countertops. sean: okay, so this is the quartz, right? robin: okay. sean: so... robin: i do like this. sean: two slabs of quartz will run us $6,000, almost double the budget. so i want to show robin something much more cost-effective. sean: this is the granite. robin: okay. yeah. we can keep moving. really quickly. sean: okay, okay. [laughs] robin: like running. sean: okay. okay, so you like none of them? robin: this one's not bad. sean: okay, we'll make a note of that. yeah, i'm sure it's the most expensive granite in the place, so we got you there. robin: i just... i don't like granite. sean: okay. no, i can tell.

the granite probably knows you don't like it, too. robin: yeah, yeah. no offence, no offence. sean: i just hope that when she hears the price difference, she'll come to her senses. sean: all right, so this was a granite. so, this was the only granite that robin liked. saleswoman: this is called thunder white, and this is $1,500 for the slab. sean: okay. did you see that? do you see why i'm leading you to granite? it's much more affordable. robin: yeah, i see. saleswoman: and the granite, it's more durable, too. robin: thank you, melissa. sean: for a rental, i would seriously lean towards this. robin: okay. ♪ ♪ sean: at the home robin plans on selling, she's followed my plan to a tee. it's gone through a complete transformation. sean: the walls are bright white, and she's staged the house with smaller-scale furniture. it's now ready to go on the market. sean: but there's bad news too. robin has a family emergency and needs to leave town, but she's agreed to meet with me about her gc's schedule

on her way to the airport. sean: where are we at? robin: don't have the inspections yet. though we should have had them by now, so we are behind on that. so he's calling for the inspections now. sean: how much do you think it's gonna push us out? robin: it could be about, i'm thinking about another two weeks. now again... sean: at least. robin: ...he's assuring me that, hey, once i get these inspections, i'm gonna go, go, go. sean: so there's no way-- you kind of need to step up the pressure on him now. robin: i agree. absolutely. sean: this impacts you much more than q. robin: yeah, and i'm spending money, so it's not a good thing. ♪ ♪ ♪ sean: it's been over two weeks since i've heard from robin, and when i drop by, there's no one on-site and the backyard still looks like a war zone. meanwhile, the reno on the house next door is completely finished. this is not what i meant about staying on schedule. robin: when we first started out it was moving well, um... and now it's really become more, hey, the inspections, this and that. sean: like, i'm not buying the inspection excuse. robin: oh, absolutely. sean: because if he was hands on

he would have figured it out. robin: absolutely. i wholeheartedly agree with you. sean: somebody's bull [bleep] me. robin: but here's the situation. he's taken on another project now, and so when we talked last week my question was, "hey, where are we from a commitment standpoint?" and it was, you know, "i'm totally committed to this project." sean: i know robin wants to take q at his word. but actions speak louder, and this flip is officially off the rails. robin: man, this is out of control now. sean: you're not finishing when you said you were. and here's the thing. my construction site, i'd clean that up, so these guys are not pissed off and she could get her house done next door. q: yeah. sean: that's how i would do it.

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has come to a complete standstill. it's bleeding both time and money. so i've asked for a meeting with her and her gc, q. sean: i'm obviously here to see what the hell's going on. q: so, uh, major problems we found out here. every time we touched a window, it collapsed, so we had to reconstruct all the windows. so if you want to come up, we'll take a look at that. sean: we can walk through,

but here's the argument i'm gonna make. you're not finishing when you said you would. like, how are these guys getting all their stuff done? they started after your one. i mean, they're well done before you now. q: yeah. robin: this is not only impacting me in trying to sell my house; it's also impacting my neighbours and what they're trying to sell. i don't like to be the one that's causing people issues with all that garbage in the backyard that we were supposed to already clean. q: it's a construction site. it's gonna have have garbage. it's gonna have everything. sean: but i've seen a few construction sites. i mean, here's the thing. on my construction site, i'd clean that up so these guys are not pissed off, and she could get her house done next door. that's how i would do it. sean: well, let's take a walk through, okay? we'll see what's changed. ♪ sean: what q is saying just isn't adding up. framing out the windows should take a week, at most. q: every time you remove one of the windows... sean: yeah. q: ...all of the bricks collapsed. sean: okay. q: so each one of these had to be rebuilt, and headers put in every last one of these windows.

sean: i guess the thing that probably is frustrating to robin is we did talk about you calling the city two months ago for the inspections. robin: right. sean: you're now talking about calling them, calling them again, or... q: electrical's been called. hvac has been called. construction has been called. sean: and they were called in... when? q: they were called friday. sean: obviously not gonna hit any of the deadlines initially discussed. sean: the way q is dragging his feet, this could go months over schedule. and in the meantime, robin's paying $2,000 a month for the mortgage. that's real money she won't be getting back. robin: so are you fully done with your other projects, so these guys can truly focus on this? or where are we, honestly? q: no. they're here. robin: but they worked over there, too. q: yeah, they had two days over there. robin: they worked over there too, which... they've been over there, q, more than two days. q: it doesn't matter, but if i got an emergency on a site... robin: it does, because it's impacting my project. so they have been over there more than two days. so one thing you said to me last week was, "i'm fully committed to your project." q: right. robin: but nobody's here today.

q: i explained to you everything that went on, right? robin: that somebody was sick. q: i said tomorrow everybody was gonna be on point. sean: that's it. i can't listen to one more excuse. as of right now, q is off the job. sean: he's definitely bull [bleep] us. robin: yeah. sean: now, not sure what the background is. he might've got too busy... robin: yeah. sean: ...but then he should've told you. right now there's a lot of bull [bleep] here at this stage. we need to get it done. robin: absolutely. ♪ ♪ sean: with q off the job, it's time to get this reno back on track. sean: morning, guys. robin: hi, how are you? luis: hey, good morning, sir. robin: hi. sean: i've brought my contractor, luis, to finish the job. sean: so we're ready to start construction? luis: we're ready to rock and roll. robin: let's go. luis: after you. sean: but just as we're getting down to business, the city building inspector shows up, and we haven't even had a chance to review any of q's work.

sean: a city inspector is kind of like being stopped by the police. i'm just always nervous around them. i have been my whole life. even when they still walk in, i get nervous. luis: how, how much? oh [bleep]. luis: yeah. inspector: well, you're eight and a quarter on your rise already, and that's eight. luis: uh-huh. inspector: you're over eight already, so... the stairs aren't to code; the headroom's not to code. luis: i have to redo this whole thing. okay. inspector: you got to reframe the whole stairwell. luis: yep, yep. inspector: so really there is no bearing wall in here, you know? this isn't-- we're not counting this as a bearing wall. there is nothing underneath it, so... we can't pass that. ♪ inspector: you know, obviously it's... it's [bleep]. luis: it is sloppy [bleep]. okay. inspector: all right. there's a ton of stuff here we denied.

we went through a lot of it. luis: there are things that we need to do. inspector: i'll put everything in the system for the next inspector. luis: please, thanks. sean: i can't say for sure, but part of me wonders whether q put off booking the inspector for so long because he knew the work would never pass. sean: first things first, i can tell by the expression on your face you know that that was pretty bad, right? robin: yeah. i mean, it was denied, so... we got work to do. luis: there is no supports on the stairs. robin: mm-hm. luis: the steps are too high. robin: mm-hm. luis: that's construction 101. robin: mm-hm. luis: sorry. sean: it's substandard work. it's interesting, you know, sometimes you don't know till you get rid of somebody that great expression that warren buffet had-- "it's only when the tide goes out "you know who's been swimming naked." robin: mm-hm. yeah. sean: and you being at this inspection was a great thing. had your previous contractor been here, this would've gotten glossed over. robin: yeah. sean: good news is, this should be your absolute bottom today, right? robin: right. sean: i mean, it can only get better from here. luis: yep, yep, true. sean: so, new day.

we're starting over. we know we've major structural issues which need to be addressed. we're gonna move forward together, the three of us. luis: yes, sir. robin: okay. good deal. sean: okay, all righty. robin: yes. robin: i got some good news. sean: okay. i always like good news. robin: yes. i got an offer on this place. sean: you did? robin: i did. sean: how much?

♪ sean: we've had to spend weeks fixing the problems that robin's former contractor left behind.

sean: load-bearing beams are installed where previously there were none. the staircase that didn't pass inspection is reframed to code. sean: the exterior brickwork is redone, and the backyard is cleaned up. all the work passes inspections. this reno is finally moving forward. but today robin says she wants to talk about her home next door. robin: i've got some good news. sean: okay. i always like good news. robin: yes. i got an offer on this place. sean: you did? robin: i did. sean: how much? robin: 375. sean: okay. i think that's good. robin: yeah, and i accepted it, yay! sean: excellent. that's really good news though. robin: i'm excited. sean: i'm excited! closing soon? robin: closing soon. sean: shall we go and have a look at this? robin: absolutely. let's do it. sean: over at the reno, luis's crew is working hard to make up for lost time. as a new roof goes on the garage, the back deck is floated with concrete, insulation goes in, and the drywall begins. [construction sounds] sean: looking good.

robin: there's a ton of progress. i can actually see it, you know, now coming to life. it's a great feeling. sean: this process has obviously been way more complicated than it should have been. robin: yeah. sean: like trying to catch smoke in a bottle. robin: i know, yeah. sean: how much had to be redone, because the previous contractor obviously didn't do it properly. robin: right. sean: lesson learned, right? robin: oh my gosh, yes. definitely. sean: feeling good. robin: oh, these guys are doing a great job. ♪ sean: all the drywall work has been done, so the whole house is getting primed and painted. new hardwood flooring is installed... [construction sounds] sean: the trim is in place, and all the bathroom tile is set and grouted. sean: meanwhile, i've found an estate sale online where we might be able to find a piece of vintage furniture. robin: i can't wait to see this bar! sean: that will bring style and function to robin's vacation rental. joe: nice to meet you. sean: and this is robin. robin: hi, joe. how are you? joe: hey, robin. come on in. sean: oh, this is something. robin: oh my. wow!

sean: so, what's the story here? joe: well, the story is we lived in this home for 62 years, and my grandmother and my mother, like, made it like a museum. sean: i love this; the plastic on the couch forever. robin: my grandma had that. joe: no one was allowed to touch anything. sean: so you were never allowed to sit on there? joe: no. off limits, guys. robin: oh my gosh. is that a kodak camera? sean: where? joe: yes, it is. robin: i came here to get a bar, but i gotta get this camera. i am serious! joe: that's the original instamatic 44 with the flash cubes. robin: i gotta buy this camera. sean: this really is like a snapshot of history. joe: and there's our lovely bar. sean: the bar, robin. robin: oh, i like the bar. joe: vintage bar. joe: no one was allowed to even sit on it or... robin: so the bar's never been used, joe? joe: no. sean: as an irishman, a lightly used bar is a very novel concept. robin: [laughs] sean: very excited about that. robin: it does look brand-spanking new. sean: this is perfect, right? robin: yes. i love it. sean: so we went and looked at some airbnbs and they had, like, a nice bar area. robin has a nice new airbnb,

so we want to have something we can put the alcohol on. robin: this is super cute. sean: 395. i need to sit down. robin: yeah. [laughter] joe: i know robin would pay me for what it's... what i have on there. [laughter] sean: all right, joe, so... if i was to say like $250, what would you say to me? joe: um... i think we could counter at 325. this is family history. sean: so that would be your final no bull [bleep] price? joe: right. sean: might you help us carry it to the car? joe: yes, i will, and i'll even throw in the camera. sean: all right, deal. there you go. robin: hot diggity dog. thank you, joe. you're a good man. sean: we have a deal. robin: i'm gonna carry the stools. i'll leave the heavy lifting to you guys. sean: that's some interesting paintwork. robin: well, this is a chalk wall! sean: okay. oh-ho-ho... this is phenomenal!

♪ sean: i've been helping robin renovate this greystone in order to jumpstart a career in vacation home rentals. and while the construction crew works on the finishing touches, i've asked her to brainstorm some ways to make her new airbnb stand out from the crowd. sean: owners who brand their rentals get more bookings than owners who don't, and robin has cleverly combined her last name with her favourite colour to come up with the carter blue. i think that's quite creative. robin: what do you think? sean: this has come together really nicely. robin: you like it? sean: yeah, i really do like it. robin: this is a fireplace i added. because if you think about it, although this is gonna start out as an airbnb, eventually i want to sell it one day...

sean: okay. robin: ...and most places have a fireplace. sean: makes sense. robin: so kinda two living spaces right here. sean: that's some interesting paintwork. robin: well, this is a chalk wall! sean: okay. robin: so that's where i'm gonna brand the carter blue. sean: okay. robin: and it'll also say, "places you wanna see, "places you wanna go. "welcome, sean. "enjoy your stay!" sean: i like that. that's really creative. robin: you know, people today love to take pictures, so envision carter blue. they take their photos, they post them on instagram, facebook, whatever... and then we've got instant advertisements. sean: so... i notice the blue door. so that's carter blue? robin: you get it. sean: i see the theme. robin: you like that? sean: i think this is really cool. and this is great. you can put two stools here, yeah. robin: a couple stools, one on the end. we had a little situation and luis informed me that there were no more white cabinets. sean: these are much cooler. robin: i love these, and i love them much more than what i would have liked the white cabinets. sean: they're way cooler. robin: yes. sean: so let's see upstairs. robin: all right, it looks great. robin: this is the master.

sean: i like it. robin: right? sean: what's your plan for the room? it's a really nice size. robin: i'm gonna do two beds. sean: okay. it's a good idea. robin: yeah. i mean, more occupancy. sean: so how many people can this home accommodate then? robin: eight. sean: okay. and then this is your master bathroom. i'd spend some money on the toiletries and stuff like that. robin: okay. sean: i had a property and the person handling it for me had insisted that i get better toiletries, that i get better dishware... robin: yeah. sean: ...that i get better pots and pans and i was so irritated, but the comments were better. robin: really? sean: it increased my rental price significantly. robin: i like that idea. thank you. sean: all right. let's head downstairs. robin: all right. good stuff. sean: you have a skylight. robin: you like it? sean: i do like it. sean: so, right now, you have a perfect canvas here. like, this is fantastic. robin: yeah. sean: it's beautiful. robin: yeah. sean: well, have you thought a little bit about what you're going to charge per night? robin: i have. we want to start out at $200 a night, but the beauty of the situation

in this deal... sean: yeah? robin ...is that i'll have somebody living here permanently who's gonna pay me a permanent rent every month. sean: okay. robin: so i've got a base. sean: so you have a rental income downstairs. robin: correct. sean: upstairs, robin will only have to book five nights at $200 each to cover her mortgage. anything above that is pure profit since she'll be getting $1,000 a month in rent from her downstairs tenant. robin: she's gonna be my hostess for this place. sean: the real key... robin: yeah. sean: ...to airbnb, responsiveness. robin: yeah. sean: so this person who's going to be your hostess, test her. call in. robin: yeah. sean: okay, so then the next thing is your reviews are so critical, right? robin: exactly. sean: so, cleanliness is the most important thing. robin: so, i have hired a person that's going to maintain it and keep it clean. sean: okay. robin: in order to pay for it, though, i'll also charge a cleaning fee from like 100 to 125 bucks. sean: plan of action. robin: okay. sean: come in here and pore over the cleaning of the place... robin: yeah. sean: ...first several times, and consistency in cleaning.

robin: yeah. sean: let's agree on a one hour... robin: one hour. sean: ...response time? and you'll test it. robin: okay. sean: and that's our plan. robin: yeah. i like it, i do. that's a good job. sean: we got a deal, again. robin: welcome to the carter blue. sean: oh my god! this is incredible. sean: for more about this flip and others, go to thedeedchicago.cnbc.com. (vo) they're adapting to supporto their communities.s. but many need our help. if you're a small business in need, or want to help a local business, go to quickbooks.com/smallbusinesshelp intuit quickbooks.

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sean: when robin bought this greystone, she planned on a quick fix and flip-- reap the rewards and start a new career in development. as if that wasn't a big enough change, we ended up revising the old floor plan and then robin decided she was not going to sell, so i had to fire the old contractor and hire a new one. now, robin's reno and her vision for a future in vacation home rentals is finally complete. sean: hello? robin: sean, how are you? sean: oh! [laughs] this is phenomenal! robin: do you love it? sean: oh my god. this is incredible. robin: welcome to the carter blue! this is my chalk wall. this is my branding chalk wall. sean: top eating spots... robin: yeah. sean: ...top bars. robin: and...

sean: top guy in the whole city ever, sean colon! this is a really interactive, proactive thing you're doing. robin: like, who would not want to take pictures in front of this? sean: it's brilliant. robin: i got a brilliant from sean! sean: no. i love it. let's do the first selfie. robin: [claps] let's do it. sean: come on. alright... excellent. robin: awesome! sean: it really brands it and it personalizes it. robin: yeah. the branding is going to resonate throughout. robin: so i have my own logo, "the carter blue." sean: very nice. robin: right? and different hues of blue throughout. right? sean: i really like it. and then, from a real estate perspective... robin: yeah. sean: ...with this wall gone this space feels spectacular. robin: it does. i mean, it opened it wide open. now, from the time you hit the door to the time you come through, you can see all the way through the hall. sean: it's great. i'll tell you what i really like too. you've got lots of different zones for people to gather in. robin: yeah, yeah. sean: the place just feels good. robin: yeah.

and here's the other thing that was good about this too. i used a little bit of new. sean: yeah. robin: but then some of this stuff is a lot of my old stuff from my other house. sean: and it worked. robin: you want to repurpose this stuff. you don't want to go out buying a bunch of new stuff. sean: and the kitchen turned out perfect. robin: thank you. this is also a place where folks can kinda chill out. sean: so this isn't the granite i was pushing you towards, no. robin: from a budget standpoint, because the project went long, the people that were working on the house next door, they got their fence up before me. so when we had to do fencing in the front, i was like, "we'll repurpose some dollars." sean: fair enough. i'll allow you to rationalize your behaviour. robin: thank you. sean: it looks really cool. robin: good! sean: the cabinets, fully stocked. robin: bam! gotta be ready. sean: and i see joe's bar. it's found a new home. robin: it has! i love the bar. thank you so much for that. sean: and it's fully stocked. robin: and check out the mugs. sean: carter blue coffee cups. robin: yes. sean: i mean, you're really going for this. robin: yeah. sean: okay, i want to see the rest.

robin: all right. let's take a look. sean, you remember this? look at it now. sean: yeah. it was a complete disaster. robin: i know. it has come a long way. sean: this is great. robin: thank you. sean: i mean, it's clean, some chairs... robin: yeah. sean: some tables, some plants, a barbecue... robin: maybe a little firepit! sean: see, that's something they won't get in a hotel. they'll have this outdoor space. robin: yeah. sean: this is great. robin: thank you. sean: this really came together wonderfully. robin: i'm very pleased. sean: let's go in through the blue door. robin: carter blue. sean: all right, sean, we're headed into the master bedroom. sean: this is great. you put the two beds in. robin: i did. sean: more guests. robin: i put the two beds in. more guests, more money. sean: still tons of space. and it's a proper master. if ever for resale... robin: yes. sean ...this room size is great. robin: agreed. sean: and the master bathroom. this turned out fantastic. you've got a huge shower. you've got the double vanity. fantastic bathtub. you've the jets in it. sean: you've done it all, and you actually got all the little bits and bobs... robin: i did. sean: to personalize the place. robin: i did.

i took your recommendation, so it was a small expense. people will love this stuff. sean: what's amazing about this is, you know, you're in a price point where... robin: yeah. sean: ...people won't get this in a normal hotel, and that kind of sets you apart. robin: my goal with the carter blue is to really make this a home away from home experience. and if you think about that, that's exactly what this does. sean: so, robin, where are the rest of the bodies going to go? robin: [laughs] robin: right here. i've got two bunkbeds in here, so folks can sleep in here. sean: cool. robin: yeah. sean: bunkbeds, i like that. robin: and then lastly, this is the last bedroom for two as well. sean: so eight people up here. robin: right. sean: okay, that should make you some money, right? robin: it should. sean: this is a really cool airbnb. robin: thank you. sean: i mean, i think it will do spectacularly. robin: thank you. i'm ready to make some money. sean: now, on that subject. how did you do here? robin: i went over my budget. sean: okay. robin: but , but, but, but-- it was warranted. so for the fireplace... sean: okay. robin: ...i had to fix the things that the first contractor screwed up.

sean: which were numerous. robin: exactly. sean: i must confess, i never thought we'd be here. when we did a deal, we stopped discussing flips, you did more of a backflip on me, and... to overuse a tammy wynette term, you stood by your man. robin: [laughs] that was not my man, but keep going. sean: you stood by your contractor. robin: there you go. sean: that being said... robin: mm-hm. sean: we're here. [laughs] robin: we are. sean: which is unbelievable. robin: abso-freaking-lutely. sean: i can't speak highly enough of your ability to listen. you listened. robin: i learned a ton along the way. so, number one, have a good plan. sean: right. robin: and then a plan b... sean: c, d, e... robin: [laughs] then a plan c... robin: d, e, f, all the way to z. 'cause something's going to go wrong. sean: yeah. robin: number two. don't look for the least expensive gc. that was like the worst thing i could have ever done. sean: absolutely. robin: you get what you pay for. sean: i'm proud of you.

robin: i never would have gotten through this without you, and it's been amazing for me. sean: well, thank you. robin: so, thank you so much. sean: now you're going to be a super hostess here, at the best airbnb in the south side. robin: best airbnb, period, sean. [laughter] ♪ tonight on the deed chicago: ♪ a couple on the rebound from the real estate crash. bernette: i had a great four-year run. then when it south, it went south. they're rebuilding their business with a house-buying spree. sean: so we're seventeen or eighteen houses? bernette: we're eighteen right now. sean: you've been out buying houses like drunk sailors! but owning too many houses is stretching them too thin. sean: when do you get the...? bernette: tomorrow. sean: and the appliances? bernette: tomorrow. sean: so it's all manana. there's no way this is finished. if they can't focus on growing smart... kai: i am strategic enough to not become so heavily leveraged. sean: but you don't have a strategy. they risk losing it all again. sean: where we sit today right now,