Frank’s bubble burst. Twice.

Frank, 55, has been homeless for years, but he hasn’t stopped working.

He was born and raised in South New Jersey, just across the Delaware River from Philadelphia. He was about 18 when his mom’s house burned down and they moved to South Florida. He lived in Fort Lauderdale about nine years before moving to Atlanta with his mother. He stayed there about 15 years before heading back south to Miami. It didn’t take him too long to find work in 2007 with a demolition company called Jampro.

“I knew every single contractor. I knew them all! They all knew me. They all thought I was an owner [of the company],” he said. His eyes light up when he talks about this in much the same way anyone’s eyes do when they’re talking about a job they love. Frank used to make sales for the company in a big swatch of Florida. “I went to all the [trade] events. And I was the frontman for the company. And they had three divisions. I loved it! Oh my God, as a sales guy? Oh my God, I loved it. We had demolition of course. And we had final clean up, and we also did where you, like, rent a laborer.”

That job played perfectly to Frank’s strengths. He built relationships, helped people solve problems, made connections, and was never in the same place for too long. This guy is restless — the type you can instantly tell might spontaneously combust if he were trapped behind a desk for too long.

“We were booming,” Frank said. “And then the construction business took a dive. They held on to me as long as they could. We were digging and digging. The banks weren’t loaning their money. So I got laid off.”

When the recession dealt a major blow to the South Florida real estate market (a story you know well if you saw The Big Short), Jampro let Frank know that they’d pay him for any business he could bring in, but wouldn’t be able to keep him on as a salaried employee. That was layoff number one.

“Huge hit,” Frank said.

Frank was out of work for a while until he managed to bring in some money making sales in the tobacco industry selling cigarettes — mostly Clippers — to convenience stores and other small businesses. Unfortunately things went south for his new employer. As the newest hire, Frank was the first one to go when the layoffs started less than a year after he’d gotten his start working in tobacco.

There’s layoff number two. He still hadn’t totally righted his ship, and now — having lost two jobs in what felt like rapid succession — it began to sink into Frank’s head that times were about to get desperate.

“There was something different about the market, about the jobs. I could feel it,” Frank said. That was four years ago, in April 2012. He’d lost his company car, so he took his last pay stub and used it as proof of employment to buy one for himself. He might not have known it at the time, but the car would eventually become his home.

Every day, Frank moves his bed out of his Scion XB and loads the car with the flags he'll be selling during the evening rush hour.

Just when things looked like they couldn’t get worse, Frank hurt his back and got a hernia while lifting a lawn mower when he was doing some landscaping work with a friend. Intensely physical labor was no longer an option. Desperate to make ends meet and merely survive while looking for work, he decided to “hit the streets.” At first, he was selling pens and air fresheners on busy intersections around Miami. He’d head to a corner and wait for red lights, at which point he’d look for any driver willing to buy his product or hear his pitch. As it turned out, though, most drivers were more interested in the decorations he had on the sign he carried with him.

“I used to keep two flags on the edge of my board,” Frank said. “I used to just do it as an attention grabber, and people would just stop — and they didn’t want to buy no air fresheners or pens. People would ask, ‘What about the flags?’ And I would get mad. I was like, ‘Man, I’m selling air fresheners and pens, not flags. Hello!’”

After this happened to him enough times, though, Frank began to realize he might be better off listening to all that product feedback. After all, Miami highways are diverse places, and the people here are known for wearing their national origin and immigrant heritage on their sleeves. He switched up his business model and stocked up on three kinds of flags: American, Cuban, and Floridian. Frankie's Flags was born.

“When you’re in sales and marketing, you’re supposed to listen. I’m Polish, so there was a delay,” jokes Frank, “but it finally kicked in.”

Forging a path

As we walk through a long hallway at a storage facility just a few minutes south of Florida International University, Frank chats with an old friend, Summer Sarmiento, who’s meeting him here to buy a flag for her kids. She’s looking for a pirate flag (you know, skull and crossbones or something like that) for her kids to fly over their treehouse. The conversation turns to a subject about which Frank is clearly sensitive: the friends and family with whom he’s lost touch over the years. He says he can’t be sure why they’ve abandoned him, but he figures some people just don’t want to associate with a homeless guy.

“You’re working hard to keep above water,” said Summer, pirate flag in hand. She went with a skull over crossed swords. “You’re doing something. You’re not blowing money on, like, drugs or anything.”

They hugged as Summer assured Frank she would be back for more flags the next time she had a little extra money for more treehouse accessories. When he talks about it, you can tell how much Frank values the support of friends. His tone swings back and forth between a giddy I’m-so-pumped excitement and a deep, trembling sobriety that comes from a deep appreciation for how important that support is. It’s what keeps him moving when so much else seems to scream at him that he should throw in the towel.

A look in his storage unit shows not only that he’s refused to give up on this flag thing, but that he’s actually come quite a long way with it. Longer than I would have imagined anyone could go selling these things on busy intersections, anyway. The unit is packed with boxes containing everything from American flags to NFL team banners to the kinds of novelty flags that Summer stopped by to get her hands on. Not all those friends have known him since before he went into the flag business, though.

Flags were never a dream of Frank’s. The top of the storage unit has no ceiling; instead, it’s covered by a net of cables that let’s all the air conditioning come in. Hanging from those cables are all of Frank’s clothes, including a number of dress shirts and ties — each one a stark reminder that this is a man still looking for a way out of homelessness. His Instagram page is littered with videos he’s recorded while wearing those shirts just before or after job interviews that didn’t pan out. Every day that he’s been out selling his wares over the last four years, Frank’s been accompanied by some version of a sign that explains he was laid off, is looking for work, and has a stack of resumes for anyone who might be able to give him a chance.

“I’m very big into self-help stuff — Tony Robbins and some of the other great personal development people,” said Ivan Osorio, who has been a marketing consultant for 10 years. “And part of what’s listed in these books is to be grateful and to do things for others so that your problems become smaller.”

Ivan’s parents live near one of Frank’s favorite intersections, so when Ivan visits his parents on Sundays, he often crosses paths with the upbeat flag salesman.

“He was asking for an opportunity. He was asking for business cards. He was asking for contacts. And so, what I saw was a guy who was trying hard, but he didn’t have a lot of good ideas. He didn’t need work ethic; he needed some marketing help to get across to these opportunities, which is what he was looking for. So I gave him my card and I had him call me. And the challenge became, ‘Can I help this guy?’ I want to help him help himself by training him, by teaching him stuff.”

Ivan says that since he and Frank met two years ago, they’ve touched base about twice a week (generally by phone). Ivan has helped Frank improve his reach online, including fine-tuning his use of social media (you can follow Frankie's Flags on Instagram and Facebook, and you can find Frank's website at frankiesflags.com) and even creating a page on GoFundMe.com to raise money for a bartending course.

“So, people make decisions in survival mode that may not necessarily be the best long-term,” said Ivan. “But he needs somebody to help him. Because there’s a lot of people who can see him and say, ’Oh, this guy’s a great opportunity for a publicity thing.’ They don’t actually want to help him. They’d actually be predatory and want to take advantage of him.”

Frank has come across some predators since he became homeless. He talks as disdainfully about companies like Amway as he does about the guys who once ran up on him on a Hialeah intersection and stole all his flags. But he’s been lucky enough that Ivan’s not the only person who has lent a helping hand.

T.J. Lago is 25. Four years ago, he was a manager at an L.A. Fitness in Cutler Bay (he’s since been assigned to another location). That was where he met Frank, who, though he was already homeless, was a member  — in large part primarily for the safe place to take a shower.

“He was a nice guy,” T.J. said, “The first time I met him was because he left his stuff [in a locker] and they cut the locks. They would have a cleanup day once a month and you’re not supposed to leave your lock there overnight.”

Frank’s heart must have skipped a beat when he first realized his stuff was gone. Lucky for him, T.J. had set it aside. That was the beginning of a friendship that made Frank’s life a little easier. When he found out that Frank sometimes got held up working the streets too long to make it to the gym in time to shower, T.J. started letting him in after closing time (which is when T.J. does his own workouts, anyway). T.J. also introduced Frank to Instagram, which has become the centerpiece of his flag business’ social media marketing efforts.

“I know how it is to not have anything. And he was really, like, a great person. He wasn’t a dick or anything,” said T.J., recalling a period during which family issues — including his mom’s leaving to California for cancer treatment — left him unexpectedly forced to live on his own for several months. He was 18 and ended up on his feet, but it was enough to serve as the foundation for the empathy he’s shown Frank.

“I hope that one day, if I’m ever in that position, bro, that someone gives a handout to me. Even though I don’t really ask for handouts, but it would still be nice, you know what I’m saying?”

When Frank met Ivan, Ivan advised him to use the Instagram account T.J. had created to reach out directly to local business owners looking for work. That was how Frank met Kevin Danilo, one of the owners of Batch Gastropub, a popular bar and restaurant in Downtown Miami’s Brickell neighborhood.

“It sounded like he had had a rough time,” Kevin said, “but [he is a] super positive guy. He was trying to do things the right way and it was impressive to see somebody who had been kicked around a little bit, but still had it in him to pick himself back up, do it on his own, do things the right way.”

Unfortunately, Kevin wasn’t able to help Frank out with employment. All he could offer Frank was work during night shifts, and because Frank sleeps in his car, getting shuteye during hot Miami days would be practically impossible (not to mention unsafe). Still, much came of the connection. For instance, when Frank posted some photos on Instagram of his dangerously worn-down tires, Kevin gave him a call and told him to have them replaced. Kevin would foot the bill.

“I’ll put it on the resume for when I get up to the pearly gates,” Kevin joked. “You know, you’ve got to show your credentials.”

Frank’s not exactly sure what motivates these people (and many others like them) to help him out. After all, not every street vendor has a marketing professional, a gym manager and a restaurateur in his corner. Maybe, Frank said, it’s that they see him refuse to quit despite having the odds stacked against him. Maybe they became invested while pulling for an underdog.

“Even now it gives me goosebumps,” said Frank as he remembered the day that Ivan told him he was “on board” to help. “I said, ‘Man, if I have somebody like him in my corner, somebody who’s a consultant, a marketing guy, and he wants to help… Wow.’ It’s hope. Man, you take hope from somebody like me, depression will kick in. You’ll give up. He gave me hope. That energizes me. It does something. When you’re down, you look for things that will motivate you. If you don’t look, you’ll stagnate and you’ll perish ... You don’t want to stay in the reality of what my life is. It sucks. But you’ve got to find things that make it not suck so bad, you know?”

Powering through

Frank is really good at finding things to be optimistic about. But to say that a lot of Frank’s life reality sucks is putting it mildly. Not too long ago, Frank had a boat. These days, during fishing season, he works some days cleaning and waxing boats for a guy named Captain Mario, who has a small fishing charter business. Except for this summer, that is; Mario’s on an extended trip, which leaves Frank without some of the income he usually counts on to eat and pay the bills during South Florida summers, when frequent downpours make selling flags an even less viable way to make a living.

I tagged along with him for the better part of a day to get a look at what his routine looks like. Here’s how that went. We started at that L.A. Fitness in Cutler Bay, where Frank had showered before meeting me. He stuck around there a while waiting for a UPS driver and checking in with him by phone to find out when he’d be arriving. He was waiting on a small shipment of 4”x6” “thin blue line” flags that he was hoping to sell to some local cops. Not having a permanent address means that when Frank gets his inventory, he needs to use the addresses of friends or friendly businesses, where he either meets delivery drivers or hopes he can count on management to accept shipments and hang onto them for him. Needless to say, this isn’t the ideal way to run a business, but he doesn’t have many better options.

After lunch, while on our way to the storage unit about 20 minutes from the gym, we stopped by a dry cleaner. Frank had realized that the button on his shorts had fallen off, so he was looking for a safety pin to close them back up. Thankfully, these people know and like Frank, too. The elderly Colombian seamstress who gave Frank a button and put it on the shorts for him told me he’s good people and that she wishes she could understand how a guy like him can’t find a steady job. Of course, there’s a lot she’s never understood about him; she doesn’t speak English and he doesn’t speak Spanish. But still, she’s seen him around enough to know he’s worth helping. Frank gave her a big hug and they kissed each other’s cheeks before parting ways, Frank going on loudly in his born-a-salesman kind of way, and the Colombian seamstress telling me, “Es un loco,”through a grin. That guy’s crazy.

After we arrived at the warehouse and Frank got through helping Summer find the right pirate flag, the next order of business was prepping flags for a day on the street. Helping him out with it was a time-consuming process due to the fact that he’s got limited space to keep his inventory and even less space to transport it in his Scion. I imagine it usually takes much longer since the norm is for him to do it all himself. The ritual involves a lot of unpacking (his flag distributor sends them individually wrapped, but Frank sells them without their plastic packaging) and counting (he keeps them in bundles of 10 so he can get quick at-a-glance counts. Until recently, the smaller flags came to him wrapped tightly around their flagpoles, so Frank would use an outlet about 50 feet away from his unit to iron them one by one. These individually wrapped flags might seem insignificant, but they’ve made a difference in his day-to-day.

Everything goes into a wire cart about three feet tall, and he’s got packing that thing down to a precise science. A combination of plastic bins and milk crates keeps everything accessible, while a couple of dumbbells at the bottom keep the wind from knocking it all to the ground. Two five-foot flags — one American, one Cuban — are affixed to the cart, making him pretty hard to miss no matter which red light you’re at on his intersection.

The finishing touch is a rigid plastic sign — with several dozen flags stuck into the top of it. One side reads:

"LAID OFF 3 YEARS
HAD TO CREATE A JOB
IT'S BEEN A LONG JOURNEY
I'M MAKING PROGRESS
Broke and trying to survive
PLEASE BUY SO I CAN EAT"
#Frankiesjourney

It's been four years since Frank was laid off, but he hasn't had the money necessary to create an updated sign. The other side (he flips it around periodically to make sure you see the whole message) reads:

TERRITORY & ACCOUNT MANAGER RÉSUMÉ

The sign Frank carries with him on the street every day is loaded with flags and résumés.

Under that text are about 120 flags and a blue folder containing résumés for any and everyone who might see him and think they have a job opportunity to offer.

Every day, just before people start their evening commutes, all this stuff comes out of his storage unit and gets packed into his car. To make room, he’s got to move his bed from the car into the storage unit. When he opens the doors of the Scion, Frank taps me on the shoulder. He wants to make sure I’m recording this bit. His eyebrows come up a bit, and he begins to gesture with his thumb and forefinger touching in that “Wait till you get a load of this!” sort of way.

“This is a class-A homeless place here, OK?” he says, directing my attention to the two blankets hanging in front of his rear windows. “I have blue matching curtains. I just want to point that out.”

Eventually, with the large white comforter and a long foam couch cushion (which serves as a mattress) out of the way, he’s ready to roll. Most of the time, all this is just enough to pay for the essentials. His car (and all the related expenses), his phone, his storage unit, his food, and laundry are all paid for with flag money — except when they’re not. He only ever asks for help when things get really desperate. For instance, there are the tires Kevin offered to buy. And then there’s the time that he was so far behind on paying for his car insurance that Captain Mario had to help him get current.

Those are the short-term problems, though. Frank’s real problem might be that he is, in more ways than one, stuck in a cycle that only gets more difficult and hopeless the longer he’s in it. Is he in a hole of his own making? There isn’t a simple answer to the question of how he got there, but there’s no question he’s in deep.

“Even though he works extremely hard, his age is against him, his education is against him,” said Ivan, “the fact that he has no permanent place of residence is against him — even though the guy will do anything at any amount of hours. He wants an opportunity badly. He would outwork so many people. But he doesn’t present the perfect case for an employee.”

Another problem: Frank’s impressive story of entrepreneurial perseverance was, for a long time, at odds with his unwillingness to admit he was homeless. Though Ivan encouraged him to “own his story,” Frank just couldn’t bring himself to admit any of that to prospective employers. Who knows? Maybe someone would have given him a shot. Maybe not. Regardless, Frank is now homeless in his 50s and increasingly forced to rely on the business (and sometimes goodwill) of passersby and his own sheer will to survive while refusing handouts. Frank says he’s not on food stamps or any other kind of welfare, and Ivan says he’s been repeatedly frustrated by Frank’s refusal to consider going to a shelter. Even when there’s a light at the end of the tunnel, it can be dim. That GoFundMe campaign got Frank bartending classes; he says he aced the written portion, but didn't do so well on the second part. He plans to go back to school and try again to master the technique, but getting there takes more time and gas than he can usually afford. Still, while they haven't been enough to solve all his problems, he has managed to get a few gigs.

“‘Why didn’t he just get a job?’ That is the million dollar question,” said Frank. “But if [people] understood the truth ... Well, when you’re down like that, it’s simple things: [having] clean clothes and everybody asks you to go do the interview. Or no gas. Or, in the beginning, no car.”

Something to hang on to...

Frank’s story can seem alien at first. Sure, we all know someone who’s fallen on hard times … or we’ve fallen on them ourselves. But how many people know a guy who’s been laid off and spent years working to get out of homelessness by selling flags — flags, of all things! — on the street?

And yet, in his own extreme way, Frank is living the experience of hard-headed, entrepreneurs we all know: the ones who become so committed to the product and the path they chose that they cling to it for dear life, believing there’s progress on the horizon even to the point of seeming delusional.

“I’ve never agreed with [flags] as a great business, but he thought of that himself,” said Ivan. “He became enamored with the idea of the flags. And that’s a problem with a lot of business people you run into. You fall in love with your idea, and the marketplace never wanted this; it never accepted it. But he fell in love with the idea of starting this business and getting out on his own without having to go to a homeless shelter, which is commendable.”

I mentioned to Frank that Ivan had told me about his criticisms of the business model. A wide grin showed up on Frank’s face.

“This is him and I,” said Frank, binging his two fists together in a crashing motion and ending his sentence with a collision sound effect.

Frank walks between lanes of traffic while cars are stopped at a red light.

“I know it’s nuts. I know it’s nuts. I’m nuts, but I want to see it through. I want to take it as far as it can go … I struggle with that. I never quit. You need to know when to wash your hands. I’m so aware of that, but I’m thinking that I’m a little bit closer to just sealing it up. I’ll tell you another reason: because the flags will always provide me a little bit of money. Just something,” he said, adding that he can see his flag business growing to include shirts, mugs, and other products.

“I’ve always seen him as kind of a representative of the average person, just at a different scale,” said Ivan. “You know, you get your family of four. They make enough money to pay the bills. Very little gets left for saving, and if something catastrophic happens then everything goes out the window. In his case, catastrophic is, you know, his tire blowing out. And that’s his house.”

If Frank’s intransigence has hurt him by keeping him from letting go of a bad idea, it’s helped in that he’s never been willing to give up hope that he can get himself out of homelessness while retaining his dignity and his sense of self worth. That’s the reason he keeps his clothes clean, his hair cut, his face shaved and his résumé at the ready.the

“It’s just, like, crazy how someone can live the way he lives but still keep like a good sense of humor, you know? He stays very positive,” said T.J. “Honestly, that’s the one thing that I love about Frankie. It’s that he’s a very positive person. Even though he has shitty days, unless you asked him, you wouldn’t even notice that he had a terrible day.”

 Author's Note:

After our interview, Frank sent me a text message insisting that I attach this image to the article I was writing. He wanted to make sure people who have helped him along his journey didn't feel unappreciated. Here are some people he wants to thank publicly.