Over nearly two decades, I backed three young entrepreneurs in Mexico, the Dominican Republic, and Guatemala. Their companies took radically different paths: one collapsed catastrophically, one sold for a life-changing sum, and one grew into a holding company. What endured across all three was something I hadn’t expected to find in investing: friendships built on unconditional love. This story follows those relationships from their first uncertain meetings through boardroom confrontations, financial crises, and a recent journey through their home countries. Along the way, the distinctions between investor and mentor, friend and family, begin to dissolve. Having struggled with addiction and mental illness, I discover that the men I thought I was helping have changed my own life. From a wood-fired sauna beside Lake Atitlán to Mexico City’s museums and a celebratory dinner in Santo Domingo, the essay explores the tension between demanding results and loving someone regardless of the outcome—and examines what happens when men accustomed to proving their worth allow themselves to be loved. *** Kalil was ugly crying the last time I was in the Dominican Republic, his face contorted beyond recognition as he tried to force out words. His management team and the board members were right there with him, tearing up as he finally said, “I failed so many times, and you never gave up on me.” We are having our closing dinner. We arrive in a torrential downpour, and the valet rescues us from the car with an umbrella, so we don’t show up soaking wet. The building resembles an office complex tucked deep within a city block. We go upstairs to a spacious area with a table, kitchen, and living room; Dominican music beats off the walls, and a half dozen guys who speak no English bustle about to serve us. I assume this is where Santo Domingo’s elite hold business dinners. After an hour of signing the final deal documents and laughing, I kick off the proceedings by reading excerpts from the thousands of emails Kalil has sent me since his original cold intro just before Thanksgiving 2014, which I tried so hard to brush aside, and by tracing the years of near-death experiences up to this evening, when all deal documents have now been signed. Funds will be wired in the morning. I'm a high-stakes gambling addict, hidden behind the cloak of financial investments, who traces his ancestors back to an indentured servant who came to America from England in 1677 aboard the ship Kent. I found it attractive that businessmen from Latin America presented a high risk. No one else would back them. However suspect my motivation was, the intervening years revealed everything. From the start, my relationships with men like Kalil were an oasis amid cutthroat American culture. These partnerships let me be open in ways I couldn’t be with my American business partners. American men are taught to guard their emotions, stay rational, and be cunning. The Marlboro Man sure as fuck didn’t cry. These guys cried a lot, and I began to, too. Over the years, I have also realized that an entrepreneur who attends Yale or Harvard for business school and then returns home to buy and build a business, largely to create good jobs for his people, has a much higher probability of success than an American one buying a software business in Atlanta. Many times, I have seen the pride in one of my Latin CEOs’ eyes as we walked the factory floor and he pointed out how we had changed hundreds of families’ lives for the better. *** “I don’t know what anyone else sees, but I see a completely unrealistic sales plan!” I exploded at a board meeting inredactedThe other two board members were stone-faced, looking at their hands. “Kalil, I’ve said the same thing at the last board meeting and the one before; you have to create a predictable sales and marketing plan, not just make this shit up out of whole cloth and hope for the best!” I said, staring him right in the eyes. With a leader like Kalil, prone to overpromising, my role was fierce love. I made it clear to him from the start that nothing he could ever do would make me abandon him. We were in this together to the death. But when he made the same mistake repeatedly, I refused to give up on him, but I was determined to physically stop him from doing it again, one inch from his face, and beat reality into his soul. In 2014, I met Kalil Diaz, a gregarious Dominican at a coffee shop on Boylston Street. For the next decade, I tried as hard as I could to knock him down, as did every element of his deal and his company, and he always bounced back, to my great surprise. It was simply impossible to kill him, as much as I, and the world, conspired to try. Kalil had recently graduated from the Yale School of Management, where I had graduated a quarter-century earlier. He wanted to become the first Yale graduate to launch a search fund. If that wasn’t risky enough, he wanted to run his search in the DR. I was skeptical and curtly responded to his cold email inquiries. He said he’d be in Boston, and I reluctantly agreed to the brief coffee meeting. I fired question after question at Kalil, but his enthusiasm wore me down. Up to that point, his fundraising had gone nowhere. Eventually, in January 2017, I helped Kalil buy a call center, CCD, in the DR. Right after the close, we saw each other briefly at a Yale event in New Haven. He was upbeat. Then, a week later, he called with terrible news: the company we had acquired was not what we thought it was. Instead of generating close to a million in profit, it was burning cash—a LOT of cash. The ship was sinking. FAST. We immediately implemented weekly board updates and daily cash reports. I started talking to Kalil every day as I walked my dog. It took most of a year to stabilize the company. Then we had to figure out what business we were even in, build a team, and start winning new customers. This took another couple of years. We finally realized that focusing on U.S. imaging companies, which private equity was rapidly consolidating, would give us the expertise to charge more and build a competitive moat. We endured two hurricanes. But COVID was the turning point. Our team had to figure out how to provide continuous service while setting up our agents at home in a business highly dependent on complex scheduling IT platforms, dependable dial tone, and data lines in a country with quite undependable internet, power, and phone service. Kalil’s team came together in the crisis and, amazingly, achieved this near-impossible feat in less than a week. We started to grow revenue quickly but still couldn’t figure out how to increase our profit margins. Kalil was just too nice to cut the costs needed to achieve economies of scale. I slammed the boardroom table some more over margins Kalil honestly thought impossible to achieve. In 2022, as a board, we went to an industry conference in Chicago, where I first saw signs of the coming AI wave. The team was talking about various joint ventures to keep pace, but I knew we needed to exit before the knife fell on our heads. Over the next year, with coaching from my best friend Pete Flick, who is as tough as Kalil is nice, Kalil doubled our profit margins from the mid-teens to the upper 20s. It was a perfect storm that delivered a great outcome for our investors and an unimaginable payday for Kalil. After we sold our company, Kalil had to endure two years of working for the new Indian owner after the close as part of the deal, but his life was changed forever. *** “I still can’t believe everything that happened,” Kalil confided in me when I arrived in Santo Domingo on my Latin America tour to visit my CEOs last August. “It still seems like a dream to me. I just turned forty, and I have my whole life ahead of me. Next year I’ve been asked to lead the National Association of Young Business Leaders. I’ll meet with the Dominican President and high officials regularly to ask for my opinion.” By the time I got to the Dominican Republic this time, Kalil had just returned from two months in Europe with his wife and young kids. He hadn't been around much in the prior twelve years because he had worked around the clock. “The trip was amazing,” he told me when we first met in the hotel lobby for a drink, giving me the long, strong hug that had greeted me from the start. “I remember walking into one of our board meetings after we had been at this for five or six years, struggling our asses off,” I told him at dinner. “And then I realized that the only ones talking were director-level employees, not board members, not you, and not your team of direct reports, but people four levels deep. And they were clearly the smartest people in the room by far. Then I knew we were onto something.” The next day, Kalil and I walked around the colonial part of Santo Domingo, stopping at the spot where Christopher Columbus first set foot in the New World in 1492, and then made our way to sit as far out as we could into the tropical blue-green Caribbean ocean at Neptuno’s in Boca Chica, soaked in sun and humidity, eating lunch to lively local music. Unsaid were the many tough conversations we had had, the thousands of emails we’d exchanged. Now all that was left was love. *** The first time I met Will Thorndike, his office looked more like a borrowed closet than a place of business. We were both in our early 30s. He told me about the tow truck business he was investing in with great enthusiasm. “That’s literally the stupidest idea I have ever heard of,” I said bluntly. The company, now called Asurion, became one of the single greatest investments of all time. Will still owns his original shares thirty years later. Will and I met just after I sold The Providence Journal Company inredactedWill’s dad, Nick Thorndike, a founder of Wellington Management, served on The Journal Company board and was a pivotal mentor as I navigated a series of complex, controversial, and huge transactions as a barely 30-year-old CFO. Nick introduced me to his son when the dust had settled, and Will and I became fast friends despite my arrogance as, at least in my mind, a Wall Street wunderkind already. Will soon upgraded his office, taking over the 5th floor of #11 Newbury Street, a few steps from the Boston Public Gardens, and asked me to join him on the 4th floor and encouraged me to think about starting a venture firm, building on a fortunate investment I had made just after selling the Providence Journal in a company called Art Technology Group, in which my investors made 500x in three years. A decade later, now 43, I was exhausted from firing and shutting down companies. Unfortunately, my luck did not continue. It took a decade, through the teeth of the internet bust and the financial crisis, to scrape out a return based on 2 of 25 investments in my fund that kind of worked. Will had watched my VC woes from the front row. By then, he had become famous for publishing Warren Buffett’s favorite business book, The Outsiders. Housatonic was a top-decile performer. When I asked what to do, he told me about another way to invest, called a search fund, which involved backing a bright top-level MBA to buy and run a company designed to be unbreakable, where it was hard to lose money, unlike my VC fund. Asurion, and many of Will’s key investments, started that way, so he quickly became the go-to search investor in the country. I made many Search Fund investments, served on several boards, and was the first to write regularly about various aspects of the ecosystem—becoming a thought leader of a sort. One of my random blog posts argued that the way search CEOs had always been compensated had unexpected negative consequences—it incentivized CEOs to sell quickly, even though, as investors, we wanted more time to compound returns. I developed a different approach and published it inredactedTo my great surprise, it became the industry standard. It even started appearing in deal documents, referred to simply as the “Matlack Formula.” Corporate lawyers now routinely approach me when they hear my name to ask if I am “the” Matlack, which I find weird and mildly embarrassing. *** For my 60th birthday in December 2024, I invited ten guys, including my brother, Augusto, and my eldest son, to Tucson for a few days of hiking and biking, highlighted by a ride up Mount Lemmon, an infamously challenging ascent. Each day, we began by watching the sun rise over the desert, then sat in a circle to meditate and share our lives. On a particularly hard hike, Augusto turned to me and said, “I know how to suffer, Tom. Let’s see who gets to the top first!” I still find myself looking at the photo I took that day of Augusto, grinning at the summit with his arms raised. Augusto gave me an Oaxacan wood carving of a Red Bull, which sits on my desk to this day. Like the bull, he grew stronger each day, fueled by long talks with the other men on our walks. By the time we reached the base of Mount Lemmon, an unrelenting 6,500-foot climb, Augusto stormed off the front. My brother and best friend from college are serious riders, but Augusto is in a different class. He would circle back to check on the peloton, ride down the hill, and ask, “You guys, okay?” We were hurting but making steady progress. He’d take off again, only to return half an hour later to check on us. Finally, Augusto and I sat alone on a bench outside the little grocery store in Summerhaven, the Mount Lemmon summit village, at 8,500 feet. I tried to get an orange creamsicle, my safety food after near bonking, down without puking. Augusto told me about his mountain-biking exploits in Mexico and the Triple Bypass he completed the prior summer in Colorado, and he invited me to ride it with him the next year. *** Will introduced me to Augusto Alvarez and José Luis, two Mexican students at Harvard Business School. Augusto recently told me we first met in January 2008 near the Barking Crab in downtown Boston. I can’t quite remember it now, 18 years later. All I remember is that he spoke with an artist's precision. Augusto’s close-cropped beard and slightly receding hairline made him look older and wiser than his more traditionally handsome, baby-faced partner. Augusto did most of the talking. I was drawn to the way he spoke, formal in word choice yet a street fighter in execution. During all the trips that followed, I never even went outside. I stayed in a hotel connected to our office building in the Santa Fe section of the city. The focus was always work. Nothing else mattered. We left the Mexico City office only once for a soccer match in all those years. At Azteca Stadium on November 13th, 2013, I hear the roar of 99,832 Mexican fans shouting obscenities at the New Zealand national team goalie before Mexico even kicks off. I ask José Luis, Augusto’s co-founder, what they are saying. We are in the 10th row with Miguel, the head of sales. Someone has already poured a beer over my head, assuming I am supporting the Kiwis. Apparently, he didn’t even care that I had bought a green Mexico jersey for the occasion. “You don’t want to know,” José Luis quips. Augusto is at the hospital. His daughter, Natalia, is about to be born. Mexico scores. And scores again. I begin to feel a little safer in the cavernous shrine to soccer, hostile to anyone who isn’t obviously Mexican. The final is 5-1. We go to dinner to let the horrific traffic die down. *** December 3, 2017, Will interviewed Augusto and José Luis at Harvard Business School. I sat in the back of the massive auditorium, a thousand people hanging on their every word. They were rock stars in bright lights on a stage of blond wood and stylish chairs. Will asked them what their exit plan was. “We don’t ever plan on selling,” José Luis replied. Will turned to the crowd with a grin that silently said he approved of the answer. AlphaCredit was a rocket ship, peaking at 1,300 employees. The company operated as a credit union for federal and state employees in Mexico. In this cash-based country, consumer loans had always been made on the grey market at exorbitant rates. I wasn't on Augusto’s board of directors, but if he called anyone in the middle of the night in a crisis, it would be me, whether to architect a new financing structure for the company or to sort out a thorny HR problem. The story did not have a happy ending. On April 20, 2021, AlphaCredit announced major accounting errors. The company had hired a new CFO, who reviewed the prior Comptroller’s accounting and found the mistakes. Soon, the company became a house of cards and a living hell for my friend Augusto and his business partner. He endured two years of excruciating bankruptcy negotiations and proceedings until, in 2023, their dream was officially dead. Throughout, the press and the investment community were ruthless in their judgment. Most investors and board members were incredibly frustrated with Augusto, turning something that wasn’t his fault into a personal issue. I'd been through enough personal hell to know that true friends show up when the world gets dark. We had frequent Zooms, calls, and texts. My message was always the same: “I love you; we will get through this.” *** “This is where I came every morning,” Augusto tells me on a sunny Saturday morning this summer. “To gather my strength for another day of hell.” I flash back to a Zoom meeting we had shortly after the 2021 crash. Augusto was at home with his dog, and then one of his daughters appeared in the background. He told them to go away, and when he turned back to the camera, I could see the pain and desperation in his eyes. I listened, wanting to reach through my computer to hug him. We stood in front of a giant underwater reservoir called Fuente de Tlaloc. “All the water flows here and collects the city’s water. The hydraulics were very advanced for their time,” Augusto told me. “Depending on the Mexico City Mayor, they either clean this whole area up to celebrate it, or let it go completely wild,” he went on. “I like it like this, overgrown and wild.” We turned the corner, and Augusto pointed to the large open field atop one of the reservoirs and told me his daughters loved to run up there when they were little. Then we walked a little farther to a giant effigy. I couldn’t quite make out what was going on in the massive pool with bright-colored tiles. “It’s a sculpture by Diego Rivera,” Augusto said, “to honor Tláloc, the Aztec god of rain, with two faces, one looking up into the sky and the other toward the reservoirs. It is meant to be seen from the air. If you look down as you fly into the city, you may be lucky enough to see it. But you must pay attention.” *** We started Saturday morning at the Museo Nacional de Antropología, founded in 1964 and housing the most prized Aztec relics. “Look at the architecture of the building,” he told me as we walked in. “The walls are all covered in Aztec patterns of wood, repeated throughout.” Then we walked to the Museo de Arte Moderno. “In 2024, I came here with my wife and daughters,” Augusto started, and I did the math: this was the year after AlphaCredit's final collapse. He goes on to tell me he revered his grandfather, Augusto H. Álvarez, an innovative architect who designed, among many other important structures, the Mexico City Airport and Torre Latinoamericana, one of the most iconic buildings in the city’s historic center. “We went in, and there were my grandfather’s drawings,” he says, getting misty now. “I just started crying hysterically in front of my kids. I couldn’t help it or stop.” We sat down to a traditional late Mexican lunch at Augusto’s friend’s restaurant, Ricochet Apéro in Roma Norte, a fringe neighborhood. The restaurant is housed in an old, run-down building filled with junk that had to be cleared before a 1970s French Riviera-themed restaurant could open. The moment we sat down, the skies opened, and torrential rain crashed down on the metal roof, making it hard to hear each other. Augusto’s wife, Valeria, and his 14-year-old daughter, Isa, joined us. “Bad Bunny is my favorite musician,” Isa told me. It was the best I had seen my friend in a very long time. He had just taken a new job as #3 at a large, successful company. While he still mourned the loss of his company, he talked a lot about how the dark years had opened him up and given him a more grounded perspective, even as he had to make new friends who shared his new values. *** The steam overwhelms my body with heat. Juan, a dark, handsome man in his mid-30s who generally listens intently, taking in the whole person while he thinks and speaking only when he has something important to say, has just sprayed a metal box containing a red-hot wood fire with a hose. I am sitting on a plastic chair, menthol in my nostrils. Three other Guatemalan men accompany us into this squat, traditional cement sauna, with a door low enough that I must stoop to get inside. “In a ceremony,” Juan explains, “everybody holds hands, and no one is allowed to leave until the shaman says so.” Finally, overcome by the heat, we walk gingerly down the dark rock path to dive off the dock and into Lake Atitlán, surrounded by three volcanoes. The cool water against my skin, as I look up at the stars, makes me feel the closeness of my creator, while Juan treads water nearby. Last year, we held our first management retreat at the lake, where all these men grew up and have come for spiritual retreats their whole lives. I shared not only my business experience but also my struggles with addiction and mental health. Others did the same. “What are you doing?” Juan asked me incredulously the next morning on the Lake, sleep still in his eyes, looking at me like he had seen a ghost. He shook his head, clearly disturbed. Juan described grinding local beans and preparing a pour-over coffee as a religious experience. I was caught red-handed with a bottle of Nescafé Instant Gold, spooning it into hot water, in the home of the world’s greatest coffee. Each of my friends appeared to see what was going on, laughing but not happy when they realized my American ignorance. And that ribbing has continued ever since, with constant references to my poor judgment and taste when it comes to coffee, at the heart of Guatemalan identity. *** In 2016, I sat on a park bench outside the Charles Hotel in Harvard Square on a cool spring morning with Juan de Dios Aguilar, a Guatemalan who spoke so softly I could barely hear him. He was impossibly young at 26. This was my craziest idea yet: to invest in a search in such a small, less-developed country, but I had a gut feeling about Juan. Juan’s innocence, his youth, and his dream captivated me. I pushed my chips all in. I believed in his dream for reasons I couldn’t articulate, and I later even second-guessed myself. He was intensely shy and introverted. Yet when he spoke, he was brilliant. And courageous. And humble. “What did I just commit to?” I thought when I got home and reviewed Juan’s deck. But then I remembered his demeanor, and the surprise and joy in his eyes when I told him I was in at the end of our meeting. It was almost like he wanted to leave as quickly as he could to make sure it was real, and I couldn’t change my mind. “I can’t let this guy down,” I told myself, despite the questions that snuck into my brain. *** “There he is!” Juan’s dad, also named Juan, said, pointing at his son on the TV. Juan’s brother had just come on the field during a Guatemala national team soccer match against Israel. Juan’s wife, Danny, very pregnant with their first child, Pilar (now 9), hosted us in their new home. That night, I officially became part of the family and kept sneaking glances at this beautiful young couple: Danny, so pregnant; my friend Juan. And sharing the joy of the soon-to-be grandfather, so proud of both of his sons. Less than a year after agreeing to back Juan, he bought a door manufacturer in Guatemala, and I started making annual trips to visit Juan and his team. *** In the middle of the first pitch of La Nariz del Indio (“The Indian Nose”), overlooking Lake Atitlán, I was in trouble. The grade was unrelenting, and the altitude, seven thousand feet, was crushing me. I dropped back with Ian, the slowest in the group despite being a college soccer player, pretending to make sure he made it up, but just holding on. “I have held onto your words from our conversation last fall,” Ian, who now runs our door company, confided. He had been in the middle of a crisis caused by inventory mismanagement at the factory, followed by the sudden resignation of his sales leader. Our operation's financials had fallen off a cliff. I remember the conversation, sitting in the study of my mother-in-law’s house in Florida, telling Ian I loved him and that one year’s results didn't matter; this was a long-term game. “I didn’t know it,” Ian said. “But that was the point at which things started to get better. I learned so much.” The first hour is the hardest. Then the path flattens out, and we get back to where we turned around last year because we ran out of time and rushed back to the city for a shareholders’ meeting. The summit looks right there, but it’s not. The trail snakes around the back and through a mountain town, completely unmarked. Then we are back on the path and the final push. I fall in with Juan. “Last year was so pivotal for Ian,” he says. “I’ve thought a lot about how every great leader must go through a crisis like that. It forces them to grow. You really helped him.” *** Last summer, I had a 4 a.m. flight out of Guatemala. The hotel arranged a car for me at 1:45 a.m., but after I checked out and got to the street, no car showed up. The hotel had mistakenly reserved it for the following day. Luckily, someone else had hired a car for the airport at the same godawful hour and was about to leave. They were fine with me joining them, but their driver wasn't. He kept telling me in broken English that it was illegal. For a good ten minutes, I was sure I would miss my flight. I finally just started waving U.S. dollar twenties at him, and he relented. Squeezed into the front seat and moved all the way up so I wouldn't disturb the original passengers who had so kindly let me join them, I looked out the window at Guatemala City passing by in the dark. I thought of climbing the hand of God, a bright yellow twenty-foot structure with black, white, and blue steps, with Juan at the summit of La Nariz del Indio two days earlier. I have always been terrified of heights, unable even to go up a tall ladder. Behind the outstretched palm, a sheer drop fell thousands of feet to the deep blue of Lake Atitlán and the volcanoes beyond. I wanted to take a picture with Juan in that spot so badly, but I couldn’t bring myself to stand. We sat cross-legged for a while, knee to knee. Then he stood up, and I stood up too, leaning on him for strength, holding him in a death grip even though he was half my size. All I remember now is blue sky and sunshine. Something shifted in that moment. I could see the vastness of our journey, of my journey, and take in its beauty right along with the view. My heart filled with gratitude for the insane long-odds miracle of me being in that incredibly beautiful spot, shoulder to shoulder with this guy I had met on a park bench in Harvard Square more than a decade earlier. Before my visit last summer, Juan and his business partner, Ramiro, hosted my son Cole, a rising senior at Brown University, as an intern in Guatemala. They left such an impression on Cole that when he came home, he openly talked about the kind of man he most wants to become. He went to Ramiro’s house to watch the first U.S. World Cup match on a Friday night, expecting to meet Ramiro’s wife and kids. “The whole extended family was there!” he told me later, enthusiastically. “Siblings, cousins, nieces and nephews. And each one of them was so well-spoken, so kind, so bright, so accomplished,” he said with awe. “Yeah, dude, it’s Guatemala; that’s every night of the week there.” *** Tom Matlack is a writer, investor, and mentor whose work explores the intersection of business, masculinity, recovery, and human connection. A former chief financial officer of The Providence Journal Company and founder of The Good Men Project, he has spent decades backing entrepreneurs and helping them navigate both business challenges and personal crises. He created the “Matlack Formula,” a widely adopted approach to compensating search fund CEOs. Today, he mentors business leaders, people in recovery, and college students, drawing on his own experience with addiction and mental illness. He lives in Massachusetts with his wife, Elena. redacted