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tonight, you've won the lottery. should be easy street, right? easy to lose that money. meet some recent winners who admit they're overwhelmed. >> you're afraid of having all

this money. >> now state line's getting them help. donald trump teaching money 101. >> going to be interesting. going to have a lot of fun. >> should they gamble on real estate? should she start a business? ivanka takes this one. >> should they give to charity. advice that might help with your own nest egg. >> don't do that with your house, okay? because you'll run through that money very quickly. if you've ever dreamed of winning the lottery you may have imagined yourself surrounded by on lens and luxury in a place like this. but that's not always the way it works. sometimes the biggest lottery winners become losers, their millions gone. good evening. i'm lester holt. at dateline we're helping some

big winners, hoping that won't happen to them. we've brought in donald trump who owns this incredible penthouse. he's got some sensible and surprising advice that can help anyone. here's natalie morales. ornls whenever lotto fever hits, people go crazy for tickets. you've probably already decided what you would do if you won. buy that dream house or car. quit your job. after all, who hasn't fantasized about wenting the lottery? for these three couples, those dreams are a reality. this woman split a $224 million jackpot. >> my daughter called, and she started screaming. we're rich. we're rich, we're rich. and she said oh, i'm sorry, you're rich. >> this couple one part of it 241 million. >> i had a friend call me and

say are you a millionaire? and i said yes, i am. >> and this husband and wife won 128 million. >> i was just like wow, and then wow, and then a couple other choice words came out, holy, you know. >> we know. >> but there can be a down side to winning the lottery, because believe it or not, one study says people who win the jackpot are twice as likely to go bankrupt as the average person. some call it the lottery curse. it's a curse these two nowell. they are lottery pioneers who make commercials together. in the early 1980s, they were the first people to ever win $5 million each in a lotto. that may sound small today, but back then, it was a world record setting jackpot. it made them instant celebrities. and when curtis showed up at his

press conference, he made news for more than just winning. >> i came over there with my wife and my girlfriend. >> this is my wife barbara. and this is my wife to be jackie. >> that was really something during that time because people couldn't believe that i would go to a press conference with my wife and my girlfriend. >> unfortunately, the men are no longer known for what they won, but for what they lost. they're both now broke. curtis says he spent his money on houses, cars and women. >> there is not one dime left of that lottery money. not one dime. i spent and lost every bit of it. >> thank the lord. >> but after losing everything, he turned to god and became a preacher in tennessee, now living on about $500 a week.

lou says after a divorce and cash gifts, friends and family, his fortune was simply squandered. he now spends his time in florida trying to win a few bucks at the dog track. he ended up in a trailer and today survives on just $250 a week. he has a dire warning for new lottery winners. >> it can happen to all of you people. so don't let it happen. >> and these winners are listening, because they're terrifying of also losing it all, becoming victims of that lottery curse. >> my biggest fear is going broke. >> she is a single mom who made just $25,000 a year working for the state of missouri. she struggled to feed and clothe her three kids, while at the same time making mortgage payments on this house. it all changed in 2006, when a co-worker asked if she wanted to join the office lottery pool. >> that was the first time i bought a lottery ticket with my fellow employees.

my first time playing, and it won. >> splitting her winnings with 12 of her co-worker, sandra took home a little under $7 million. this is where she lives now. but because she knows what it's life to live hand to mouth, she wants to do something to protect her fortune. her idea start a business. >> i would love to design shoes for women over 50. >> but starting a new line of shoes could mean an investment of hundreds of thousands of dollars. a big business gamble. >> robin anderson of kentucky also knows what it's leak. they spent many years working in this car seat factory, making just about $20 an hour. >> i don't miss it too much. >> every week, was a financial struggle as they tried to raise a family. >> it does feel good to not have

to come back. and god blessed me for a reason. i doesn't know what that reason is yet, but he's blessed me for a reason. >> can you give me a bonus? >> they were the only winners of a $128 million jackpotment they took home after taxes a cool $43 million. yet it's still hard for rob to imagine having so much money. perhaps that's because when he was a teenager, he was so broke he lived in a car for a few weeks. >> so how much are you still that young man, that 19 year old who was homeless living out of his car? you're still living with that fear when it comes to money. >> i think psychologically, yes. the public doesn't know what rob has been through to come all the way to the bottom of the rope. >> it's a big change. >> you know, it's scary. >> they have been very careful how they spend. one of their first purchases was

some kentucky land. but now the andersons want to spend, possibly millions of dollars in the risky florida real estate market, on a second home they hope might be a good investment. kelly and annie certainly know what it's like to be in the red. >> i had overdraft notice in my mailbox the day we won the lottery. >> annie worked in a greenhouse earning $8 an hour, while kelly worked in the shipping department at a quaker oats plant. >> the day that we won was like the most surreal day that i felt in my life. >> kelly and 19 other quaker employees shared a power ball jackpot for 241 million. after taxes and splitting it, they ended up with 5.6 million. >> my life in the last three years has changed so dramatically that i wouldn't even recognize myself. >> annie has had a view very

tough years, and now she wants to help other whose are struggling. >> i think we're pretty grounded people. and we're not going to just blow it. and it's going to bring a lot of good to those we know and those we don't know. >> but the lottery world is littered with people who lost it all by saying yes too many times to too many people. so we brought in someone who knows a lot about making money. he has 40 years of experience in real estate, investing and just plain making money. it was time for our winners to meet donald trump. coming up. >> sandra, we are going to speak. >> professor trump gets right down to business. these mr. clean guys, they're like a clean team. did you see mr. clean disinfecting bath cleaner killing that bacteria yesterday, just flaunting it? and did you see the magic eraser clean up that crazy kitchen mess?

it was like super dirty, super clean. how? wish i hadn't. [ sniffs ] what's that amazing smell? it's mr. clean with the amazing scent of gain. wow! you know, if i had a team, you'd be on it. [ gasps ] our mascot could be a cleanosarus rex. you're off the team. [ male announcer ] dirt and grime have nowhere to hide with the mr. clean clean team on your side. but all i do to be broadcast ready damages my hair and scalp. then i uncovered head & shoulders damage rescue. it relieved my scalp and rescued my damaged hair. the proof? see it tonight, at eleven. head & shoulders damage rescue.

we flew our three couples to new york city. we brought them to donald trump's famous headquarters and set up in his soaring lobby. >> welcome and congratulations to all of you. but when you think of making money, one man rises to the top and that would be donald trump. are you ready to meet mr. trump? >> yes. >> mr. trump. >> hi, natalie. >> it's an intimidating space for these newcomers to the world of the ultra rich.

we brought in lou eisenberg and curtis sharp. >> do you remember lou or curtis? >> i do. and it was a big deal. they won a tremendous am of money and how are you guys doing? >> winning the lotto was a real good thing. >> remember when they starred in lottery commercials they separately lost every penny of their jackpot. >> you lost your women on wine, women and song? >> yes. >> was it worth it? >> to me, it was. >> what would you advise them. >> i would advise you, there's only so much you can give out. i gave out a lot of money, and now if i need 10, $20, nobody is around. >> ironically, trump is the first to say he knows all about losing money. >> in the early 1990s, i owed billions of dollars. and the markets have totally crashed.

but the real estate, all of a sudden it was worth one third of what it used to be worth and i was stuck with billions of dollars of debt. today he's estimated to be worth 3.1 billion. and now he wants to come to the rescue of our lottery winners to make sure they don't lose all their money. >> let me start off first with sandra. >> trump has already done some of his homework. he immediately zeros in on sandra. >> so sandra, how much did you invest and how much is it worth today. >> well, actually i invested approximately 6 million, and now it's a little under 4 million today. >> sandra, we are going to speak. i don't like that. >> me either. >> that's not great. so you said four. >> yes. >> but i know you already, sandra. it's less. >> what is it really? >> 3.5, correct. >> trump's already worried about sandra's track record, especially since she wants to

take another chunk of her fortune to start her own company. charles is her fiance. >> charles, do you think she has what it takes to succeed as a businesswoman? >> of course. >> you better say that, charles. you have no choice. you know that, right? >> right. i know. >> sandra, what do you think? do you think you have what it takes to beat the odds? >> yes, i do. i have great confidence in myself. >> i have to say. come here sandra. you're beautiful. >> thank you. >> it looks to me like you do have sha-- but you do have to b careful. >> yes. i don't want it to blow. >> what about the freshman? >> we just won in june. we're babies. >> remember, they've had their own hardships. and now they want to help others with some of their money. but trump's concerned about how they're handling their millions

and said they've already made a rookie mess take. >> so how much money did you invest? >> well, we haven't invested anything at this point. >> where is the money now? in a bank? >> in a bank. >> it's drawing 1% interest. >> if that. >> when it's sitting there at 1% or less it's loses money. >> last we had the former kentucky factory workers. they now have over 38 million in the bank. a far cry from the days before their lottery win. >> you were actually sleeping in your car for a while, right? >> yes, i was. >> now they want to invest in real estate, and they've obviously come to the right man. and they want to buy in one of the most risky housing markets in the country. >> do you think south florida would be a good place to put your money? >> yes i do. i think the market will come back. >> not all of your money. the worse would be if you ended up in ha worse position than you

were before. we will not let that happen to you. >> who will listen to trump's advice and who won't pay attention? what he's going to tell them will be useful for any one who wants to make and protect their money. >> it's going to be a lot of fun. coming up, sandra wants to risk lots of money for a business. >> do you believe she has a good idea? >> but will sandra get the

sandra has big ambitions and even though she's seen her investments lose money, show's thinking of gambling her remaining money to start a business. she needs trump's help because after all he's started a lot of successful enterprises. and sandra, as we already know, could use some advice on protecting hermon eye. >> oh, man. i had a fit last year because i was like i have a million dollars. >> her $6.5 million fortune has sh rungs.

>> sandra's an interesting case. but i think before anything else, we should go out and hire a forensic accountant. find out what happened to her money. where is her money. because i have a feeling that some money is gone and maybe not for the right purposes. >> so we recuted randy wilson of rgl. a top forensic accounting firm. think of him as kind of a csi investigator of money. he went to sandra's missouri home to gather as much evidence as possible. >> our plan of action is we're going to look through all of your documents. >> that's six years of financial records. >> there's always a possibility of fraud. when someone's concerned like sandra was about what happened to the money. >> a team of three accountants expects to spend two weeks going through all of sandra's records. their mission, solve the mystery of her missing money. in the meantime, sandra wants to move forward with her business

idea. >> now you are thinking about an investment in a shoe business? >> when i go shoe shopping, it's like man, the heels are too high. after ten minutes, i'm screaming. i can't do this any more. so when i go and i find shoes with short heels, it's like there's no bling to it. they're plain. >> bling means shiny, makes a statement, leak these store bought shoes. so she came up with an idea, comfortable blingy shoes for older woman. >> you know, i'm a young 53. >> yes, you are. >> and perhaps i need to look into designing my own shoes. >> but a key factor why so many small businesses fail is lack of experience, and sandra doesn't have any serious business experience. her fiance charles says that's not going to stop her. >> has she changed much since she won her money? >> no.

she always had a little fiery personality. but now that she's won, you might say it kicked it up a notch. >> and sandra says she is up to the challenge, because she's faced major hardships before. she suffers from lupus. and years ago had an addiction. >> what happened is i hung out with the wrong owd, experimented with crack cocaine. i did not like the fact that, you know, my children, you know, had a mom that smoked crack. and i looked at myself in the mirror, and i did not like what i saw. and i asked god, i said this is not me. i said lord, i said would you please help me. >> sandra says god answered her prayers, and she stopped cold turkey. she feels especially blessed having later won the lottery. now she hopes to be blessed again with her shoe idea. >> sandra loves shoes, and

that's the business she wants to go into, and it's a tough business. but my daughter ivanka has a very successful shoe business. i'm going to set sandra up with ivan ca. she can learn something. >> that's one of trump's key pieces of advice. get expert advice. sandra's idea has got eye advantage ca curious, but she has concerns. >> i think you have to recognize your strengths and your weaknesses. i'm a big believer in being honest with where i know i can deliver. i have a very specific design's threatic. with that said, i know nothing about shoe construction. >> that's why ivanka partnered with the fisher company. they make guess and tommy hilfiger. we met with its founder, mark

fisher. >> do you think she has a good idea. >> i think the idea is a good idea for blingy shoe, but moistly for younger people. i think the concept of having a well priced shoe that has the comfort aspects to it, i think there is a niche for that. >> the experts think show has a good idea. but a good idea is only the beginning. >> you have to do your research. and whatever you think you're going to spend, it's going to cost you a lot more. >> fisher says just launching one shoe design could cost hundreds of thousands. even with her lottery winnings dwindling and her fear of losing it all, sandra wants to gamble. >> sandra, you have 3.5 million left, right? something like that? >> are you comfortable with spending some of your own money? >> i don't mind investing my money. because if it's handled properly you're going to get double what

you put in or even more. so the answer to the question is yes. >> later donald trump holds nothing back when he gives sandra his opinion on her shoe idea and her plans to double her money. coming up, rob and tuesday go on a five star tour of prime real estate, but first trump has a warning about cash flow. >> don't do that, okay? a how to guide to buying property. save them. woolite everyday, cleans your jeans and won't torture your tanks. woolite washed clothes look like new, longer.

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bob and tuesday anderson are former car seat workers, have about 38 million sitting in there bank account. right after they won the lottery, they bought their kentucky land, hoping it was a good investment. now the couple wants to do more

deals. they're willing to spend up to several million to buy a second home they hope will grow in value. but their time, they want to enter the risky florida real estate market. first, they're going to see how to do it right. >> this is where the cream delaw come, right here. >> we took the couple to florida and brought them to donald trump's palation winter estate. sitting on 20 acres, it has a total of 126 rooms. trump bought the property in 1985 for 10 million. and businessman that trump is didn't just use it as a residence. he converted it to a private club and built a huge ballroom for events and weddings. trump says his initial $10 million investment is now worth well over $100 million. >> rob, tuesday, natalie, how

are you? >> for rob and tuesday, this isn't just lifestyles of the rich and famous. it's a first hand look at how to invest in real estate. >> this is a beautiful place. tell us about it. >> it's a very special house, right on the ocean, fronts on the lake and the ocean. >> now this was a house that originally was owned by. >> marjorie weather post, who was the wealthiest woman at the time of her death. and she built this with ef hutton. >> what is this room that we're in? >> this is the living room. you see the gold bouillon ceilings. don't do that in your house. okay? because you'll run through that money very quickly. >> now it's time for rob and tuesday to pick out their dream home that they also hope will be a good investment. trump suggested that francis webster show our couple three different properties. >> all right. are you ready to come in and see

house number one? >> yeah. yeah. >> so, welcome. this is a modern dream house. >> wow. >> our first property we called the modern house. what makes it distinct is its unique, simple but elegant design. >> a lot cleaner than what i've got. >> lot of house, right? >> you have a little over 8,000 square feet. >> how do you change the light bulbs? >> you have somebody do it for you, rob? >> oh, yeah? >> sitting on the water, it has an incredible pool, hot tub and boat dock. along with four bedrooms and seven baths. >> i love this place. kind of reminds me of miami vice. but i think it's better. it could be ours. and. >> yeah. it could be. >> tells what it goes for. it is 5 million.

>> across the way in palm beach is millionaire's row. >> on to the next property. >> this is the build your dream home property. >> it's a vacant lot. what makes this property unique is that there are only a handful of lots still available on the west palm beach water front. they could build around a 6,000 square foot house. >> and you also could have a dock right out your front door. >> so you like this idea right here? >> i love this idea. >> all right. well, francis, how much? >> it's $995,000. >> well, that's not bad. >> check out the third property. >> thousand with time to see our third and final property. it is by far the largest. >> what do you think so far, looking at this house? >> it's very attractive. it's pretty. >> does trump own this? >> no, but it kind of looks like he would, right?

>> this house sits on 1.6 acres. it has eight bedrooms and 13 bathrooms. it's highly stylized and very ornate. oh, and it's 23,000 square feet. >> now we're up on the second floor, which is the main living space. >> there's a movie theater, gym, bar, arcade room. and it even has its own workshop. >> now is this a good man cave for you? >> oh, this will work. this will work. >> outside, a gigantic pool and a dock right on the water. and there's a special bonus. the owners are throwing in all the furniture plus his and her bentleys, currently parked in the garage. >> this is listed for 11 million 700,000. what do you think? >> that's really not bad for all the kit and caboodle you're going to get.

>> now most people would find this experience fun, but something surprising happened during the middle of our property tools. the andersons opened up about the pressure of suddenly winning so much money. >> you're afraid of having all this money in some way. >> in some way. it's kind of scary. you look back and you say oh, i was so happier. >> when it was simple. >> you had a job to get up and go to work. you knew what time basically you were going to get off. and we had a lot more energy when we worked than we do now. i think it brought the laziness out in us. >> they don't want people to think they're not grateful because they are thankful for winning the lottery. >> you need something new. >> you need to keep your mojo going, you know what i mean? >> is it a good idea to pie any of these places? what will trump say? >> i love the fact that you're doing a second home. number one, you can afford it. number two, look at it as an

investment. because second homes can be phenomenal in investments. >> a lot of people look at south florida and may be a little hesitant about the market bubble that burst. >> i believe the market's going to start going up very substantially. >> it was time for a decision. the first house they looked at was the $6 million modern house. >> the first home, it wasn't for me. >> so forget it. don't buy it. >> that's mr. trump's instint, you have to love it. >> property number two is the vacant land. it may have looked like a bargain for under a million dollars, but trump, a developer, says building is often one big headache. >> building is very, very hard. you just don't want it. it's very hard. >> not worth building a dream, though? >> you know, you can buy a dream. and by the way, you're living your dream the following day. you don't have to be building two years, three years.

>> the last house we called the big house. >> it had a lot of amenities and the detailing was nice. >> in the end, the andersons picked the big house. >> you really liked it? >> oh, my gosh. >> is it new? >> 2003. >> the house has been reduced from 15 million to 11.7 million. >> still too high. >> trump thinks it's too much for the anderson does spend and too much for that house. but if they still want to buy it, he offers this negotiating advice. >> you have something people don't have, you have cash. say we'll give you the money tomorrow night. incentive for them. they'll probably tell you no. and a week later you'll probably get a phone call, well, let's talk about it. >> can the andersons be as tough as trump wants them to be? we'll find out later if they get the house. coming up. annie and kelly want to share the wealth especially with those

they love. but how do you decide whom to help and how much? >> a lot of people give their money and give their money. and in the end they end up with nothing. >> when dateline continues. need a tow or lock your keys in the car, geico's emergency roadside assistance is there 24/7. oh dear, i got a flat tire. hmmm. uh... yeah, can you find a take where it's a bit more dramatic on that last line, yeah? yeah i got it right here. someone help me!!! i have a flat tire!!! well it's good... good for me. what do you think? geico. fifteen minutes could save you fifteen percent or more on car insurance. where does goddess begin?

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it's one thing to lose a lottery for tune to bad investment. but what about losing it by

having too big a heart. they have plans to give some of their nearly $6 million away. >> right away, we knew we wanted to share it. >> the thing i see is we can help the communities. you know, we can help our families. >> but that kind of generosity can lead to big problems. for annie and kelly, setting themselves up to give away too much of their money, trump has an idea. >> i think really appropriate for kelly and annie. i have a son eric who's very smart. but he's a very charitiable guy. so i'm going to ask them to go see eric trump. >> but before we meet eric, you need to know why annie and kelly are so insistent on helping others. >> my life in the last three years has changed so dramatically that i wouldn't even recognize myself. >> kelly is annie's second husband. before that, she was happily married for 25 years to her first husband, paul, but sadly

within months of be being diagnosed with a rare lung disease, he passed away. >> a couple weeks after his funeral, i had a notice that we were being foreclosed on. and i didn't have a clue that it was that bad. >> paul handled the finances and never told annie their farm was in foreclosure. her children were out of the home and grown. now her husband was gone. she felt so alone. >> there were mornings i drove home from work and i didn't want to go in the house, because i was so empty, i thought you're going to lose it all. where are you going to live? i'd sometimes turn the car around and go somewhere else because i didn't want to come in the house. >> but then something happened. annie decided to use the little money she had socked away to take her kids on a vacation to st. thomas. and that's when everything changed. starting off by buying a lucky ring. >> a jeweller came up to mow and said you look like you need a

layer march. i said what is an larimar. she said lucky stone. i said lady, if you knew how much i needed good luck, you'd sell me continue of them. >> kelly was in st. thomas too. and on that same day annie bought her ring, he made a rash decision and suddenly changed his hotel to the same place annie was staying. they met, fell in love and eventually married. >> it was a treatment come true. i was really a dream come true. >> but the newly weds still had the problem of saving annie's farm. they didn't have the money. and then three months after they married, kelly and 19 of his co-workers from a kwaeker oats cereal plant hate the power ball. >> the day we won the lottery, that was like oh, my god. all these things start going in your head. what can we do with that money? well, du, we got to save the

farm. >> not only could they save the farm, they now had the money to rebuild it. the couple is tearing down the old barn to build their dream home. >> what's happening today is so unbelievable, building a new house and starting a new life and everything. so it feels great. well, then there's this other little thing i got today. >> well, what? >> and on the anniversary of annie's first husband's death came a letter. >> the mortgage has been satisfied. >> the couple was able to fully pay off the mortgage. and annie says it all started when she bought that ring. >> i have had people want to buy this ring. they want to rent it. they want to wear it on vacation. >> whatever the reason for their good luck, the couple has pledged to help others. >> congratulations on everything that you've accomplished. >> so when annie and kelly met up with eric trump at trump

national golf club in new york, that was the first thing on their mines. >> how many people ask you for their support, i mean? >> eric knows about helping others. >> thank you for everything you do. >> since 2006, his foundation has raised over 6 million for the needy. eric who works for his dad, says his family gets asked every day for money. >> we were born into such fortune and we grew up in places like this. and we realized how fortunate we were. it would be great to have that blank check and write one to everybody. >> but eric says you just can't do that. he adds the key is to use both your heart and your brain. for example you don't always have to give money to help others. you can volunteer with your favorite charity. that's what eric trump does. here he is running a benefit at his dad's golf course to raise money for the kids of st. jude's

hospital. and ton ald trump adds that sometimes you just have to be tough. there's no better tip than learning to say no. >> how do we say yes and how do we say no. >> well, for one thing, you have to be very careful. because a lot of people give their money and give their money and in the end they have nothing left for themselves. >> virtually all lottery winners get letters asking for money. they have heartfelt pleas. >> there are so many different problems in the world. some of them are big. some of them are little, but they are just horrible and horrific problems. there are people that come to you with unbelievable stories. >> trump says the hard part is to emotionally ignore those letters or risk become being a charity case yourself. but even he admits sometimes you make an exception. >> i remember years ago a woman, annabelle hill, and she was going to lose herb farm, had no money, and i helped them out. it was just a story that

bothered my. >> that's a story certainly annie can relate to. so will this couple be able to say no? will they use their heads and not just their hears when it comes to giving to others? we'll find out later. coming up, donald trump gives his thumbs up or thumbs down to each of our lottery winners' dreams. and a big revelation for the woman who want does go into shoe business. >> i think that she's

after six months, have our lottery wenters learned anything from the trumps? >> so welcome to my boardroom. >> time to face the boss, today with another one of his sons. >> i see you brought along one of your trusted advisers, donald trump junior. >> first up sandra and charles. she's down to about half of her original 6.5 million in winnings. donald junior says he relates to losing money, especially when it's been given to you as a gift. >> he took a lot of risks to create something.

a lot of my job is about preserving. >> he better not lose it. if he loses it -- >> i don't know if i'll be looking up or down at him. but i'll be saying you're fired. >> and i'll be in trouble. >> first, as to sandra's money trail, the forensic accountant thinks he knows what happened and thinks sandra is responsible. >> as far as fraud, in my scrvi that was not there sflchlt one reason, she simply spent too much of her money. >> what he found is you spent a lot of money paying taxes. there were purchases of cars, homes, and boats as well. >> sandra, what's going on here? >> actually, one of my investments was with like real estate. >> right. >> and it did good up until 2008. >> well, a lot of people got hurt around that time. >> it turns out sandra probably sold that investment too soon. >> so it went down. but then it was coming up, and

you decided to get out. >> correct. >> if she had just left it there, today, it would most likely have come back in value. but sandra really want does know is what trump thinks about her starting a shoe business. remember the experts thought she had a good idea. >> do you think it's still a good idea? >> it's a lot of work. a lot of work. >> are you ready to do that kind of work? >> well, yes. because now i'm about making money. >> but trump has a different idea about her plan. >> well, i absolutely would not go into the shoe business if i were you. i think it's highly competitive. i know a lot of people in the business. they're total killers, maniacs. the chances of you making it are leak one in a thousand. you will have absolutely nothing. >> sandra's taking trump's advice and not going into the shoe business and show's taking his cue by learning more about money. >> my advice would be go and

take classes, an investment. my money, i feel right now is in good hands. and it's growing. >> i think, natalie, that san twra's learned an amazing lesson, pretty expensive lesson, and you're in the process of building it back up again. >> now what about rob and tuesday and their real estate hunt? remember they saw a $6 million modern house, a vacant piece of land, and the big house, 23,000 square neat for 11.7 million that they liked the best. >> we didn't have a lot of money prior to. and we can afford it. and it was, it was all that plus some. then it came with two bentlies. >> but trump sees the two cars as a red flag. >> is that a plus or minus? >> a minus because that means they can't sell the house. houses are really going up. >> you're saying now's the time

to get in? >> you can get a mortgage for 3% interest. it's like they're giving you the money. >> trump also told the andersons they need to get over their anxiety about being reluctant millionaires. >> you are so different from some of people we've dealt with. because some of these people have lost everything. and you're the opposite. you don't want to spend anything. i like you much better. because your thinking is much better, but you're being overly conservative. trump's marching orders? >> i think it's time to buy a house. >> i would say you can't take it with you. enjoy it. but think of it like an investment but do your homework. >> i'm ready to take off in his jet right now and go down there and buy one, you know. >> it turns out rob and tuesday decided not to buy the big house, because the location wasn't right for them. but they're taking trump's advice and going back to florida

to look for a home. >> we're passionate about our charity. >> as for kelly and annie, donald thinks their story gives inspiration about others. >> i think people learning about your story can promote such hope because you really overcame the worst possible adversities and you kept going. >> and the best ending of all is that they are sticking to their dream of giving some of their money away. $75,000 to the united way. but they promised the trumps to not only give with their hearts but also use their heads. >> i have great respect for what you do. i think they're solid. i don't think they're going to be blowing that $5 million. just keep up the good work. really fantastic job. >> with that, our lottery winners are on their own. after spending time with donald trump they're more confer dent, more determined to remain

millionaires for the rest of their lives. as for the rest of us, if you're in it to win it, just remember, it takes a whole lot more than a winning ticket to make your dreams come true. >> the smell of money. that's all for now. i'm lester holt. thanks for joining us. this sunday a critical phase for the obama agenda -- guns, immigration, and can gridlock in washington be broken? my lead guest is the key gop player in the immigration debate, florida senator and prospective 2016 presidential candidate marco rubio. also had morning the gun debate. high emotion as newtown families fight for tighter gun