So You Want to Get Rich Quick?

Illustration by Mark Matcho

You never really learn much about life from your triumphs. You learn from your mistakes. I’ve been in the investment world for decades, and my biggest takeaway is that you never really know anyone until you’ve dealt with their money, be it personal or business. It brings out the best and the worst in people, and it offers great insight into their character.

I was perhaps 34 years old when I made my first foray into getting rich through the work of others. At the time, there was a stock-market fad involving “the power of youth.” The theory was that young people had more discretionary income than any other generation, and their spending on clothing, sports equipment, concerts, and cosmetics would make fortunes for the people who sold it to them.

Stock markets embrace the fads of the day. Until they don’t. Riding this wave was a friend of mine, Steve. He created a travel business sending teenagers abroad, a fast-growing market. Steve said to me, “Why don’t you raise money for the business and come aboard? Then your firm can take us public. No one in this space does it like we do.”

I’ve been in the investment world for decades, and my biggest takeaway is that you never really know anyone until you’ve dealt with their money.

I was a young stockbroker, subject to fear and greed, just like everyone else. I’d have a piece of the new company. So I booked an event room at Copley Plaza and invited about 20 clients, along with several rich friends of my parents. One of them, a very large man in the corrugated-box business, came up to me before we began. “Look,” he said, “don’t waste your time with these pishers. I’ll take the whole deal.”

“Appreciate it,” I said, “but I have to spread the joy around, give everyone a chance.” The large man wasn’t happy.

During the meeting, Steve, the CEO, was charismatic, spinning the dream of purchasing power in the hands of the young. Everyone there could feel it. I felt it myself. Steve had produced a greedy response, and I sensed that the seed money would probably be oversubscribed. While Steve took questions, I took a men’s room break. At one point in the bathroom, I bent down to flush when my glasses fell off, dropping into the toilet bowl. It was a flush of giant proportion, and even though I plunged my arm in to retrieve my eyewear, the whoosh of the toilet carried them off to Boston Harbor.

I was excited by Steve’s deal, but I felt like an idiotic, klutzy fool. When I returned, Steve’s assistant was writing down the names and addresses of the investors. Six months later, the company paid a dividend to everyone.

Still, fads in the stock market inevitably fail: bowling companies in the 1960s, double-knit fabric companies, the dot-com era at the end of the century, the “meme” stocks during the pandemic, and on and on. After a year, even the youth-revolution fad faded. The company so greedily wanted by the large man went down the toilet, along with my glasses.

Evidently, though, I didn’t really learn my lesson. I continued to believe in characters. And people’s dreams. I believed I could still hit the jackpot.

Photo via Getty Images

When it comes to investing, people cannot resist restaurants. Everyone loves them. In the early 1970s, Julia Child was a phenomenon on WGBH (now called GBH) and around America thanks to The French Chef. She put cooking shows on the map. Also at WGBH at the time was a cameraman from Rome, Franco Romagnoli. He was a creative force at the station. He could write. And he could cook. He and his wife, Margaret, catered lunches and dinners at the station for the employee gatherings. At Julia Child’s peak, the Romagnolis confided in a few GBH employees that they’d like to be the channel’s next breakout chefs—this time, for Italian cuisine.

And they were. Franco and Margaret had perfect chemistry together, like Steve Lawrence and Eydie Gorme. Franco was sly and mischievous; Margaret was no-nonsense and the foil to his impish improvs. Their show was a national success, and their cookbooks a hit. At the height of their success, they called me out of the blue. “We’d like to tell you our concept for cashing in on our success,” Margaret said to me. “We’re in many cities with our show, but we’re making nothing really. We want to do a restaurant chain. Pasta bar, pasta boutique—for Italian food never served before in Boston. Not even a hint of red-sauce Italian from the North End.” It all sounded good to me. But I needed help with the deal, so I enlisted a friend who was a consultant at Arthur D. Little, went to Harvard, and had been signed by the minor leagues out of college as a left-handed pitcher. He was also a bachelor who loved to cook and had the time to be our business manager.

My friend did the negotiations when we opened in Faneuil Hall. The Romagnolis were the chefs and the creatives. I raised the seed money. At the time, I really knew nothing about business, so I cared about the quality of our investors, not so much about the money. We were raising $150,000, and I wanted modest entry costs: 10 people (five couples) at $15,000 a unit. In my naiveté, I wanted interesting people who would become friends. We held a dinner for potential investors at the Romagnolis’ big Victorian house on a hill in Watertown. All anyone had to do was taste the food…and they were in. Friendships quickly formed among the group; after all, this was the rare private investment that was about pleasure, not about getting rich—although we all thought that the artistry of the menu and the concept would set us free.

My first real business lesson came after we decided to add a line of pasta sauces to sell to the public. We were hiring a food consultant to ease us into the sideline. He estimated what his services would cost us. “Wow,” I said to my friend. “This is a lot.”

“Don’t worry,” he said. “Don’t you know that a bill is not really a bill? It’s the beginning of the discussion.” Golly, and I’d always thought a bill was a bill, and you had to pay it. Ultimately, we settled with the consultant for half  what he originally asked.

I received another lesson right before we opened, when Marriott approached us to perhaps buy the whole enterprise and roll out the concept to many of their hotels. We thought, Gee, if they want us before even opening, wonder how much more we can make if we have a giant hit on our hands running it ourselves? Greed is good.

Romagnoli’s Table opened in 1979 and was packed almost every lunch and dinner. We were profitable in our second month and were paying dividends after a few months. The investors were making friends with one another. The food was fantastic; I had lunch there every day. But the Romagnolis wanted to expand. We opened two other Romagnoli’s Table locations, one in Burlington Mall and one in Salem, on a wharf.

Guess what? The restaurant business is a killer. The Romagnolis, challenged with one successful restaurant, were having their lives destroyed running three locations: staff problems, broken cash registers, no air conditioning. Times three. All of the profits in Boston were going to shore up the other locations. Marriott, where were you when we really needed you?

We bumped along for a few more years. Finally, my friend put the lease on the Boston restaurant up for sale for $1 million. We settled for $25,000. Everything is negotiable.

I’m glad I had the experience, but I’d never invest in a restaurant again. I’d rather invest in a comedy troupe. Oops. I did.

I’m glad I had the experience, but I’d never invest in a restaurant again. Masochism never appealed to me. Having a great chef guarantees nothing in running a restaurant; it’s more about who’s watching the cash register. I’d rather invest in a comedy troupe.

Oops. I did. It was an improv group in Boston, a smart, very funny band of jesters, boys and girls, who were going to be more successful than the Brits’ Monty Python. A few thousand bucks would pay the investors back many more thousands. My wife and I went to some rich person’s house in the suburbs to watch the group perform. That evening, the group urged us to throw them any topic that interested us, from presidential elections to our children’s schools to professional sports. They would improvise sketches on everything and anything. And they would become bigger than Saturday Night Live. The investors would share in the spoils.

A year later, they disbanded. Lesson: You cannot have a band or a theater group of creative people and not have serious human-nature squabbles that eventually break them up. Martin and Lewis, Sonny and Cher, Lucy and Ricky. On and on. The cards are stacked against you. Investing in plays, musicals, or movies may be fun and give you bragging rights to “being in showbiz,” but mostly, you’re greeted by producers with a thought balloon over their heads that sings to them, Hello, sucker.

I loved the players in the improv group. Individually, they all went on to successful, interesting lives. So please, go to the movies, go to the theater, watch documentaries. If you invest in them, though, rub your rabbit’s foot for luck. You may, of course, hit that dream of “the three cherries” on the slot machine. But it will never be quick.

“I have money in a deal” is a line some use to brag about their private investments, like they’re in a special club. It sounds important, mysterious. It smacks of real money.

People often like to make themselves seem a little grander, a bit smarter. “I have money in a deal” is a line some use to brag about their private investments, like they’re in a special club. It sounds important, mysterious. It smacks of real money. “I own stocks”—that sounds boring. Investing in a “deal” makes you sound like a big shot.

Here’s one time I entered a deal, partially to tell stories about it at cocktail parties. I put money into a friend’s public relations business. He was moving from the financial business in Boston to Hollywood, where his heart was. He was a salesman—charming, smart, funny. Perfect for Hollywood. He was a big man, but one of those big men who was agile and coordinated, a fine athlete. He had something that Hollywood loved and aspired to. He went to Harvard Business School. So he should know. Right? He could build a roster of clients where he could use his charm and his résumé. I gave him a check, thinking he could create another CMA Entertainment with super-agents and, eventually, producers of content.

He had the vision and the energy. But he thought he was the smartest guy in the room, and he loved to prove it to himself by the amount of alcohol he could bring on board. When he lit himself up, he was prone to tell people around him about their various shortcomings, like the comedian Jim Carrey in Liar Liar. The people he insulted were often the clients he was courting—producers, studios, execs, actors. It didn’t take long for him to become persona non grata in Hollywood. His money, and our money, went south. He came back East.

The lesson from this? There are people, friends and relatives, who we’ve tried to save over the years. But these are people who cannot be saved from themselves. No matter how we try, they will do themselves in.

Sometimes, even prospective suckers like me can see through a proposal that will likely end in tears. One year, a gregarious golf buddy came into my office after lunch. “It’s get-rich day,” he said with a giant grin. It had been raining out, and he shook himself like an animal, the rain from his coat spraying around him. He was drunk, slurring his words. It was a time when it was common to drink at lunch.

“I want you to come on board, be my partner, set you free,” he said. He took several little bottles that looked like nips out of his pockets. “You’re out at a pub, reeling from the feeling of too many see-throughs (martinis). You get on the road. Then you see the blue light behind you, the siren on. You pull one of these out of your pocket. Open it, drink the liquid. In a minute, it goes to work, and you’ll pass the breathalyzer. Genius.” Then he breathed all over my assistants and told them he could make them rich. My assistants looked at each other and nodded. Both got up and headed toward the door. One of them looked back and said, “We don’t drink. Good luck.” He made a few pitiful attempts to take one of my assistants to lunch. “I’d eat dog food in the street before I’d have a meal with you,” she said. He grabbed his “sobriety nips” off the desk and left.

I gave another pass to a persistent young man who was a neighbor. He was the kind of person we all know, well meaning and nice. But you didn’t want to get trapped by him. “Just one more thing,” he’d cry out.

“I’m late for a dentist appointment” was just one of many excuses I once used to get away from his pitches and earnest obsession with never letting me get away. He nabbed me one day while I was heading for my
car. “I love chatting with you,” I said. “But no time…”

“I’ll just give you the elevator pitch,” he said. “You want to get rich, right? I want it worse than you. Here it is: More people are getting to be billionaires because they invented something. They filled a need. Rich people worry about their kids. A rich kid gets born. I’ve got a chip. The docs put the chip somewhere in the brain of the baby. Someday, the baby gets kidnapped for ransom. Police track the kid through my chip. Brilliant? Fills a need.”

“I’ll mull it over during my root canal,” I told him.

Another time, someone wanted me to invest in a deal he had already entered. He said he wanted to do me a favor. He was John Keane, the brilliant founder of Keane Associates, the company that helped save us from the Y2K scare that predicted all computers would crash on New Year’s Eve, 2000. “I’ve just met a young man who is a senior at Harvard. I think he’s got something interesting going. Would you see him? Hear him out?”

“Sure,” I said.

The young man came into my office the next week. His name was Bom Kim, and he came from South Korea. After we said the usual polite intros, he told me, “I have an idea for a new magazine. It’s modeled on Vanity Fair. About Harvard. All the characters, all the gossip, a shiny splash full of all things Harvard. We’re calling it 02138, the Cambridge ZIP code.”

“Gee. They already have an alumni magazine,” I said. “And a limited audience, I would think. The world doesn’t need another Harvard magazine.” He gave his best shot to win me over, telling me that the minimum investment in the deal was something like $50,000 or more.

“I’d really like to write for the magazine,” I told him. “I think I could add a lot of value to the enterprise. Tell you what—I’ll give you $15,000.”

Bom Kim hesitated. “The units are $50,000,” he said.

“I think what I can contribute entitles me to a discount. Come back to me.”

He called me the next day. “You’ve got a deal,” he said.

A few issues of glossy Harvard stories and profiles came out. I hadn’t written anything for the magazine. Bom Kim called me after the issues were released. “Guess what?” he said.

“Not a clue,” I answered, expecting the worst.

“We’ve just sold 02138 to the Atlantic Monthly. You’ve doubled your money.”

Not quite enough to set me free, but maybe my luck was changing.

Several years later, I received a phone call from Bom Kim. He told me he had gone back to South Korea and wanted to know if I could help him find John Keane again.

“I’ll email you his info,” I told him.

Then I reached back out to Keane. “Do you remember Bom Kim?” I asked. “The Korean kid with the Harvard Vanity Fair magazine? He’d like to reach out to you.”

“Do I remember him?” John said. “He’s like the richest man in Korea, a billionaire.”

“What?”

As it turns out, Bom Kim had started the Amazon of South Korea, which he called Coupang. It went public some weeks after he called me, making the young man even richer than he had been. The stock jumped as high as $48 the first week. It sits now at $17.

My really big score would have happened if I’d had the opportunity to buy into Coupang early. But I didn’t.

My really big score would’ve happened if I’d had the opportunity to buy in early. But I didn’t. Who could’ve known that the young man producing a slick magazine would become a billionaire?

Still, I have hope. Just this week, I got a call from a friend’s grandson who developed an app focused on sports gambling. The young man tried to explain the methodology behind his app, which he promised would turn users into successful gamblers. I told him that gambling was not my forte and I had to take a pass.

“Well,” he said. “Think about it. The country is getting betting crazy.”

I declined again. But a few nights later, I woke up at about 4:30 a.m. with one thought.

Maybe this is it. Maybe this is the big one. Gambling. A sure thing.

Then I thought again: Investing in cannabis was also a sure thing.

How’s that going?

First published in the print edition of the December 2023/January 2024 issue.