The Education That Paid Me
"Look around," Richard always told me before takeoff. "See if you can spot the federal marshal."
I never could. But I'd spend the whole flight trying.
Then, waiting for our car service outside whatever airport we'd just landed at, he'd continue the game. "Did you see him? Row 12, Nike hoodie." Or another time: "Two marshals today. One transporting a prisoner, sitting one row behind the other marshal."
"How do you even notice these things?" I asked once.
"That's your problem," Richard said, scanning the pickup area. "You're not looking for what doesn't belong."
That conversation happened on a flight to close a deal that would change my life. But it started months earlier, in a way I never saw coming.
[NOTE TO READER: Names, cities, and certain identifying details have been changed to protect the privacy of those involved. But the essence — the texture, the lessons, the emotion — is exactly as I lived it.]
I didn't apply for the job. It just happened to me, the way things sometimes do when you're too young to know what you're walking into, and just old enough to say yes anyway.
It started in San Francisco. I was three years into investment banking, already an associate, already restless. Most people I knew were still running the treadmill; gunning for VP, chasing bonuses, grinding through decks and 2am "just one more change" calls. I was losing interest. Or maybe I just wanted something different. Something that wasn't… dead inside.
I flew to LA under the vague notion of a meeting. No email confirmation. No agenda. Just a location: a movie producer's office. Brad. Big name. Bigger real estate. His office was bigger than my entire San Francisco apartment building. The ceilings alone looked like they belonged to a former church. Original Rothkos hanging on the walls like postcards from a world I'd only read about. Brad himself was Hollywood distilled into human form; gold chains catching light over wrinkled linen, constantly checking his phone while explaining "the vision" to anyone who'd listen.
I walked in, sweating through my collar, and there they were, Richard and Michael. But they weren't alone. A Swedish hedge fund guy who looked like he bench-pressed for meditation. An actress I recognized but couldn't place. Some tech entrepreneur along with various other people floating around the office, some who seemed to serve no purpose other than to fill space and look important.
Richard was the one I'd known longer. I'd interned for him years earlier, in Chicago, back when I still thought of finance as something you got into. He was quiet, unreadable, calm in a way that was either Zen or unnerving. His power lived in the spaces between words. Michael was different. Michael filled the room with his voice and energy, the way some people walk into a room and you know the entire night just shifted its orbit.
Both men are gone now, Richard passing about four years after Michael.
They asked me questions about deals I was working on. "Anything interesting?" Michael asked like it was a joke. Richard barely spoke, just flipped through a folder like he was scanning a lunch menu. I couldn't tell if I was being interviewed, tested, or baited. I tried to keep up. At one point Michael interrupted me mid-sentence and asked if I liked boxing.
After the meeting we had dinner, then a party in the richest part of Beverly Hills. One of those nights that folds itself into your memory like a dream. But before that, back in Brad's office, we'd sketched out something that wouldn't become clear to me until weeks later. We were framing a shareholder activism business, but nothing like the traditional approach. Richard had this vision of working behind the scenes with management teams and boards to create change through operations, culture, deal protections, creativity. Real ideas before financial engineering. We wanted situations where, if we needed to or wanted to, we could finance and buy the entire company or just get it sold, as Richard would say. We had a whole rolodex of people we could drop in on a moment's notice; new board members, CFOs, sales people, IR people, anyone we could offer to management teams to help them succeed.
Our mandate was intentionally broad; venture capital deals, LBOs, activism, prognosticating on patent infringement cases, buying companies with amazing IP that needed to be commercialized or litigated. But Richard's favorite deals were the ones where we'd form and fund companies from scratch with an entrepreneur, a board of directors, and a good idea or piece of intellectual property. We'd get through the creative phase, then finance them with capital from larger firms, other families, including royalty like the Kuwaiti families.
At the party, I didn't really understand what we were building. The whole thing felt surreal; we were framing a business model while surrounded by famous people and girls who didn't ask names. I was trying not to say anything stupid. I remember standing next to Michael at one point as a woman lit one of those skinny model cigarettes. He looked at her, smiled, and said, "Why would you want to ruin skin like that? That's silk." She laughed, put it out, and sat on his lap. He wasn't conventionally attractive. He was overweight, dressed in clothes that cost more than my entire wardrobe, and his hair had clearly been worked on, pushed back and unnatural. But none of that mattered. He had pull. People wanted to be near him.
The next morning, I went for a run through Beverly Hills. I needed to sweat the night off. I remember thinking I didn't know if I was closer to a new job or an elaborate hazing ritual. When I got back to the hotel, I asked the front desk what room Richard had been staying in.
The woman smiled like she'd been asked this before. "There's no guest here by that name," she said.
An hour later, eating breakfast near the pool, I saw him in the distance. Same suit as the night before. Rolling a carry on to a black car. No nod. No wave. Just gone. Even in departure, Richard was a ghost who left no traces.
That's when I called my dad.
"I think I just got recruited by the mob," I told him.
He laughed, but it was nervous. Like he wasn't sure I was joking.
Back in San Francisco, I tried to follow up. I called Grace, Richard and Michael's secretary, handler, fixer, human firewall. She was the kind of woman who could get you a last-minute reservation or call your bluff with equal precision. She ran their world, and everyone loved her for it. Grace had been with them fifteen years and somehow managed to mother two ultra wealthy men without losing her mind. Her husband taught high school, a sweet man who probably made in a year what Grace made in a month. She was the breadwinner, well paid and earning a small percentage of every deal that closed. When the Kuwaiti sheik visited our office, he brought her a gift, some beautiful piece of jewelry that probably cost more than most people's cars. That's the kind of respect she commanded.
During my banking years after the internship, Richard had Grace send me emails to my personal account, keeping me apprised of their deals and what they were working on. She'd also mail me articles he'd read, along with real estate listings in Half Moon Bay. To this day, I have no idea if he thought I could afford those properties or not, but he sent them anyway.
Grace said Richard would call me "if needed." Then she hung up.
I spent three days wondering if I'd imagined the whole thing. Was this real? Did I want it to be real? I'd catch myself staring out my office window in San Francisco, thinking about Michael's laugh, Richard's silence, that world where nothing was quite what it seemed.
Then my phone rang. It was Richard.
"You'll get a piece of the deals. Some walking around money. We'll move you to Chicago."
That was it. No back and forth. No negotiation. The walking around money turned out to be triple what I'd made in banking…all three years, bonuses included. And a deal cut on nothing more than a phone call.
When I got to Chicago, I was handed an office in the Wrigley Building, the kind of office with arched windows and a view of the river, the kind of office guys 15 years older than me would kill for. It had belonged to Richard's son. A guy in his mid-30s who floated around doing real estate things and trying to impress his dad with zoning maps and "intel" from local lobbyists. He was older than me, richer than me, and resented the hell out of me. Because I was doing deals, and he wasn't.
In the early days, he'd wander into my office, his old office, and randomly grab stuff from the drawers he'd left behind. Some weird power trip. When I'd walk past his new office, half the size of his old one, I'd see him staring at stock charts, doing technical analysis with a few million dollars Richard had given him to trade, surrounded by complete chaos. Papers everywhere. Just... weird.
That resentment never really went away. Not from him. Not from Richard's other kids either. I was younger, but I had the role they wanted. I sat at the table. They didn't.
But my real education started with that $600 shoe. We were in the boardroom one day with Bill, one of our Cleveland investors who spent half the year in Milan, and we'd had a fancy meal brought in from a restaurant where the chef personally came over to say hi to Richard. Bill spilled something on his shoe and said, "Oh shit, there goes $600."
I was sitting right next to him. Remember, I'm basically still a kid at this point. "Bill, your shoes cost $600?"
He looked at me with this perfectly casual expression and said, "No, but that shoe did."
Six hundred dollars for one shoe, said like it was the most normal thing in the world. That was my first real glimpse into how wealth actually worked.
Richard himself was an enigma wrapped in a mystery. During the week, he lived at the Four Seasons downtown. Weekends, he'd disappear to his house in Highland Park, the same neighborhood where Michael Jordan lived. He took HGH and probably other stuff I didn't ask about, and it showed. This wiry man in his sixties who looked like a marathon runner could crank out 30 pull-ups in a single set, do clapping push-ups like it was nothing. Doctors were constantly coming in and out of the office, not for emergencies, but for consultations, protocols, whatever cutting edge longevity treatment he'd heard about.
Richard had three phones. One was for Grace. The other two he took calls and text messages on, but to this day I have no clue what they were for. I had one of the backup phone numbers but I never used it. His rolodex extended deep into politics too; politicians, lobby firms, connections that explained some of those mysterious calls.
The secrecy extended to everything. Richard's son would disappear from the office for weeks at a time, but Richard would still need things delivered to his house. Large envelopes. No idea what was in them; I never asked, never wanted to know. But I'd make the trip because I didn't want Grace to have to do it, and because I loved Grace, and because I knew staying on her good side meant she'd share the secretive stuff with me every so often. Richard was particular about messengers depending on what was being delivered and who was involved. Sometimes it was me walking downtown or taking a cab to make the drop. I'd ring the doorbell, hand over whatever it was, and head back. Just another errand in a world where nothing was quite what it seemed.
Flying with Richard was an education in paranoia and preparation. He'd buy every newspaper and magazine at the airport; pounds of reading material including the National Enquirer, US Weekly, People. Anything with information, no matter how ridiculous. We never sat together unless it was some tiny commercial plane flying to a small city. I'd be in first class sometimes or near the front of the plane, he'd be in the back, reading everything, tearing out articles.
"Look around," he'd always tell me before takeoff. "See if you can spot the federal marshal."
I never could. But I'd spend the whole flight trying.
He'd continue the game in the taxi from the airport. "Did you see him? Row behind the exit row, Nike hoodie." Or another time: "Two marshals today. One transporting a prisoner, sitting one row behind the other marshal." The man was reading twelve newspapers and eleven magazines per flight while simultaneously identifying federal air marshals like it was a casual hobby.
It took me months to realize this wasn't a game. Richard was teaching me to see what others miss, the same skill that made him millions in deals. While everyone else saw a random passenger, Richard saw patterns, inconsistencies, things that didn't belong. That's how he spotted undervalued companies, management teams lying about their numbers, and opportunities everyone else walked past.
Richard had a knack for spotting bad actors too. He didn't always replace them right away if they were already part of the management team or when they pitched a deal, but he would make sure to structure deal terms with protections to remove them or put them in different roles. Richard honestly hated to fire people and tried to give them second chances even when he knew he needed to part ways. It was basically his one major flaw, but it came from a place of believing people could change.
When we landed, he'd hand everything to Grace. By the end of the day, I'd have a manila folder on my desk, articles with his illegible margin notes, things underlined, connections drawn between stories that seemed completely unrelated. His handwriting looked like a doctor's prescription, but somehow those notes always led somewhere.
Our office was a museum. Ancient Asian artifacts that probably belonged in the Met. Vases from dynasties I couldn't pronounce. Wall art that made you stop and stare. Michael had a real Warhol in his Chicago home office, not a print, an original. The kind of thing that made you realize you were playing in a different league now.
Monday mornings in the Wrigley boardroom were something else. It was a ritual, the kind that doesn't exist anymore. Stacks of newspapers, physical newspapers, would be spread across the table. Wall Street Journal. Barron's. Niche trade journals. Value Line binders so thick they could stop bullets. We'd stand around clipping headlines, scribbling notes, reading aloud. Old men in sweatpants. Michael in a cashmere hoodie. Richard quiet, hovering like a crow.
Grace would walk in with a coffee in one hand and a stapler like a weapon. She never raised her voice, and never needed to. Her authority was absolute, but so was the affection everyone felt for her. The acrid smell of her cigarettes mixed with fresh coffee and the musty scent of old newspapers created an atmosphere that felt both urgent and timeless. She chain smoked through everything; board meetings, client calls, even when we had special guests in the office. The FedEx guy knew her by name. So did all the messengers. She'd give them the time of day, sort of, but there was clearly history there, relationships built over years of packages that probably shouldn't be talked about.
On deal days, she'd stand at the copy machine and fax for hours while we scrambled to close. The mechanical whir of the fax machine became the soundtrack to our biggest moments. Page after page, call after call. I'd watch her talk to the most expensive deal lawyers in the city, guys charging serious money, and she'd speak to them like she was the CEO. Because in many ways, she was.
"This quote doesn't match their last guidance," Richard said once, pointing at a paragraph. "Let's find out who's on the board."
We didn't have CRMs. We had scissors, intuition, and paper trails. Deals started from clippings, from vibes, from noticing what didn't add up. That boardroom made money. A lot of it.
There were other players in our orbit; guys who'd made their money and now played with house money for fun, but each brought something different to the table. Bill, who I mentioned earlier, had stories that could keep you up all night and board instincts that were surgical.
The Palm Beach guy was a serial COO/CFO and board member who only came to Chicago twice a year, but when he walked into that boardroom, he owned it. Large, imposing, spoke directly. Everyone let him finish. He never sourced deals, but his diligence questions were razor sharp. He'd look at me and say, nicely but firmly, "Go track down those numbers in the model for me." And I would.
Then there was Tom. The operator. The turnaround guy. Less rich than the others, but the one who actually got his hands dirty. Tom called me every single day for updates on our companies. Every day. How's the cash flow? What did the CEO say about Q2? Are they hitting their milestones? Tom lived in the spreadsheets and the reality of whether these deals would actually work.
Conference calls with these guys would go for hours. I'd listen to them dissect companies, industries, management teams with the kind of precision that only comes from decades of seeing every possible way things can go wrong. I listened. I learned. I grew up without realizing it was happening.
Richard's power came from seeing patterns others missed, from making connections that shouldn't have made sense but did. He'd sit through two-hour calls and say maybe three sentences, but when he spoke, everything shifted. I watched him once negotiate a bridge loan with a tech CEO who was hemorrhaging cash. The CEO rattled off numbers, projections, desperation disguised as confidence. Richard said nothing for what felt like minutes. Just breathed.
Then: "Your runway's shorter than you think. Let's talk about what happens when you run out."
The CEO's voice cracked. Deal done.
Richard never raised his voice, never showed his cards. His silence was a weapon sharper than any argument I'd learned in business school. But when it came to negotiating with banks, he was pure Jedi mind trick. We'd have credit officers come pitch us with bound decks about their capabilities, ending with their terms. Richard would skim the materials, create some tension, then calmly tell them a rate lower than what they'd pitched and ask them to strike the two key collateral conditions they needed. "Draw up the paperwork," he'd say. "We'll have Kirkland review the docs." They'd say yes. Every time.
Richard always structured deals so we got superior terms…better equity positions, better debt terms than anyone else we brought into the deal. He had a gift for making sure his team came out ahead.
When he finally approved something, a nod, a grunt, sometimes just the absence of objection, it felt like being knighted by someone who'd forgotten he was royalty.
Michael was different. Michael had a place in Old Town; a Frank Lloyd Wright house that was a work of art. Walking into that house was like entering a temple designed by someone who understood light the way other people understand mathematics. The air smelled of cedar and something else I could never place…leather, maybe, or the ghost of expensive cigars that had been smoked by men making decisions that changed other people's lives.
Everything was horizontal lines and warm wood, built-in furniture that seemed to grow from the floors like it had always been there. The light moved differently, filtered through geometric windows that cast shadows like art installations you'd pay admission to see. Michael had incredible stained glass windows that turned the afternoon light into something almost sacred. He had that original Warhol prominently displayed, and a Calder mobile that hung in the living room, turning slowly in air currents you couldn't feel. The house had three kitchens because Wright apparently believed in redundancy, though Michael used only one. He used to joke he needed one for each version of himself.
I was often there, but I also visited him many times at his Miami mansion. In Miami, he'd hand me the keys and tell me to drive him around the city. Michael rotated cars like moods; the prototype BMW when he felt experimental, the Ferrari when he wanted to remember he was alive, the Jaguar when he was feeling elegant, the Mercedes when we were going somewhere that required actual driving instead of making statements. There was also an Aston Martin, but I never drove that one.
Those Miami drives stay with me. We'd drive to meetings with his business partners, hit Miami Heat games, attend social events where Michael networked effortlessly. The city would blur past us in waves of heat and color, salt air mixing with exhaust and something tropical I could never quite name. The leather seats would stick to our backs in humidity that felt personal, and Michael would crank the AC while rolling down the windows anyway, claiming he liked the contradiction.
Between meetings, Michael would point at gated mansions rising like fortresses from manicured lawns, their Mediterranean facades gleaming in sun that never seemed to quit. "That one belongs to a pharma CEO who got rich off other people's pain," he'd say, or "The woman in that house invented three different ways to hide money from the IRS." That one over there is Shaquille O'Neal's home.
We'd stop for Cuban espresso in little paper cups that burned our fingers, hunt down the perfect cannoli while Michael told stories that somehow became lessons about reading people, about when to trust your instincts and when to ignore them completely. Those drives taught me more about human nature than four years of college.
In Chicago, we'd walk to dinner at restaurants down the street from his Old Town house. No driving there, just walking through the neighborhood like normal people, except nothing about our conversations was normal.
He always hugged me. Always. And when we were out, which was constantly, he'd run into people he knew or they'd find him. Michael knew everyone, and everyone seemed to know Michael. Either he'd walk up to their table or they'd come find ours. No matter who it was, he'd introduce me with pride, like I was some prodigy he'd discovered. "This is Mojo," he'd say, then exaggerate whatever deal I'd closed or insight I'd had until I sounded like someone I wasn't sure I actually was.
My father didn't like it. He didn't like Michael. Too much charisma. Too much intimacy. He was jealous of our relationship, though he'd never admit it. Once, we had dinner; me, my then-girlfriend (now wife), my parents, and Michael. The tension was thick from the moment we sat down. My mom didn't like him and made no effort to hide it. My dad liked him and worked hard not to show it. Michael was amazing that night, constantly trying to ease the tension, asking my parents about their lives, their work, making them laugh despite themselves.
But the next morning, it was just me, my dad, and Michael having breakfast at my parents' hotel. Three men, no buffer, real conversation. They talked about things I can't remember, but I could feel something shift between them. They never saw each other again after that.
There was a time when Michael was sick and didn't make his usual trip back to Chicago. I knew there was a big boxing match that night, so I called him. He was watching the fight with his gardener and the gardener's 15 year-old son. Later, when Michael got really sick, he made that gardener his driver to take him to doctor appointments, obviously paid him a lot more and probably changed that guy's family's entire life. That was Michael. He collected people like other people collected art, and he took care of them.
Then came the beach house party. The one I'll never forget.
It started with a private car. Then a beach house that defied physics, the kind of place where wealth had bent the rules of reality. Studio heads. Models. Movie stars. Hulk Hogan. I'm not making that up. He was there, impossibly large and sun damaged, holding court near a tiki bar that probably cost more than most people's houses.
The whole scene pulsed with that particular Miami energy; money and heat and the smell of coconut oil mixed with something darker, something that whispered about the cost of all this perfection. Women in designer swimwear that cost more than most people's rent draped themselves across Italian lounge chairs, looking bored and beautiful and somehow separate from the rest of us.
Michael was holding court…girls on each side, drink in hand, shirt unbuttoned just enough to let the world know he didn't care anymore. He was in his element, a little sunburned, a little stoned, surrounded by chaos. In the midst of all that madness, with two girls draped around him and one kind of leaning across me, he leaned in just slightly and said: "In every deal, there are five negotiating points. You want to win three. Give up one. Lose one."
I stared at him.
"If you win all five, it wasn't a good deal," he said. "Not for them. And if it wasn't good for them, they'll fuck you later. You want a deal people can live with. That's what sticks."
He took a sip of his drink. "Take that digital payments company we're funding. They want governance rights, protection from CEO replacement, anti-dilution and tag-along rights, control over any sale process, and input on IPO timing. That's five points." He held up his hand, counting on his fingers. "We take three: governance rights, CEO replacement ability under certain conditions, and control over sale process and IPO timing. We give them one they really want: the anti-dilution and tag-along protections. And we lose one we don't really need: some of the other governance nuances."
"Why give one up intentionally?"
"Because you give it up to win goodwill. Shows you're reasonable. Winning everything makes you an asshole. And assholes get fucked in the next deal."
He leaned back. "Here's what most people don't get…every negotiation has a next negotiation. Maybe not with the same person, but word gets around. You want a reputation as someone tough but fair. Someone who drives a hard bargain but leaves room for the other side to save face. The governance rights? That's our real power, we control the board, we control the big decisions. CEO replacement? That's our insurance policy. Sale process control? That's our exit strategy. The anti-dilution we give them? That's their security blanket, and it costs us nothing if we do our job right."
"What if they're desperate and will take anything?"
"Then you still leave them something. Because desperate people remember who kicked them when they were down. And desperate people sometimes become very powerful people."
Then he kissed a woman on the cheek, stood up, and walked into the house.
That lesson fundamentally changed how I approach every negotiation. Not just in business, but in life. The art isn't in crushing your counterpart, it's in crafting something both sides can live with long term. I've used this framework in million dollar deals and buying cars. It works.
That night still plays in my head like a film I only saw once, but remember every frame.
Another time, over sushi at Nobu, he taught me the five questions he used with CEOs, entrepreneurs, lawyers, consultants, bankers…everyone. They weren't five specific questions, but five types of questions, including one that helped you figure out if you had a lifeline or not. I still use them. Still teach them to people. Maybe I'll write about them someday. Or maybe not.
There was a night at a swanky old boys restaurant in the Wrigley Building. Richard, Michael, me, and members of the Kuwaiti royal family, including a teenage prince with a watch I couldn't afford if I liquidated my whole net worth. Richard kept looping me in. Asked what I thought about a deal. Made it sound like I was the one who had greenlit the terms. I wasn't. But I played the part.
After the dinner, Michael didn't look right. Quiet. Slower. He told me he didn't feel well. He couldn't get up from his chair without my help. As everyone else shook hands and walked out, Michael asked me to stick around. "Stick around, kiddo," he said.
I felt his full weight as we got into the taxi, all of it leaning on me like I was the only thing keeping him upright. Even then, even feeling that bad, he was charming the cab driver, asking about his family, making him laugh.
I took him to Northwestern. Sat with him for hours in a waiting room while doctors tried to figure out what was going on. This was very early in our relationship, and I think that night changed everything between us.
Eventually, I took him back to his house in Old Town. I basically put him to bed that night and slept on a couch in a little nook outside his bedroom and library.
That night, we sat in the basement kitchen. Neither of us said much. He just looked tired. Like something had shifted. We would spend plenty of other nights in that same kitchen, him lighting a cigar, pouring Port older than I was, sharing joints and stories. But not that night. That night was different. That night just bonded us without any of the usual accompaniments.
He never really came back from that.
There are more stories. Deals we did that required surgical structuring…not the clean, textbook stuff they teach you in business school, but ugly, beautiful Frankenstein monsters of finance that somehow worked when they shouldn't have. We'd carve out slivers of equity so thin you could see through them, layer convertible notes like armor plating, negotiate board rights that gave us levers to pull when everything inevitably went sideways.
Sometimes those levers got pulled hard, and I'd find myself in situations no business school prepares you for.
Like the video game streaming company; a deal Richard had found through his contacts before I was there. The founder was an inventor, but he was also a semi-professional mixed martial arts fighter, a serious guy with tattoo sleeves back when only Allen Iverson and fighters had tattoos and it was still considered edgy. He'd show up to meetings in Metallica shirts or fighter hoodies, which should have been our first warning sign about fit.
When that deal went sideways, I had to help manage the investment and ultimately fly to Birmingham to shut down the company. The office was a piece of shit next to a storage facility where people kept stuff that didn't fit in their houses. Not exactly the kind of place you'd host investors. Me, basically still a kid, hiring lawyers, finding a bankruptcy trustee, navigating a mess that should have been handled by someone older with three times my experience.
But that wasn't even the hardest part. I had to fire all the employees…sixteen people, including the founder. After I finished delivering the news to everyone, I looked at him and said, "I need you to give me the keys." He forcefully slid the keys across their conference table to me and angrily walked out. Honestly, I thought he might be waiting in the parking lot for me, so I sat there for twenty minutes before I locked up and left. Missed my flight back to Chicago because it was so late.
The company failed, but we got the intellectual property through litigation in bankruptcy. Then we sold that IP to a major gaming company. Later, we tried to buy that same gaming company, but a famous activist investor installed his own CEO, so we walked away from the situation.
The term sheets looked like medieval torture devices; liquidation preferences stacked on participation rights, anti-dilution provisions that could choke a company to death if triggered wrong. But they worked. They kept dying companies breathing long enough to find their footing, gave entrepreneurs lifelines when banks wouldn't even return their calls.
The fires were constant; cash crunches, founder disputes, competitors trying to poach key customers like vultures, but the exits were glorious when they came. Medical device turnarounds that should've failed but didn't, powered by pure stubbornness and Michael's ability to convince doctors to keep working for equity when the payroll ran dry.
We weren't heroes. We weren't villains either. We were something in between, operating in that gray space where most real business gets done.
Our boardroom was lined with deal tombstones. LBOs with 10x returns, patent settlements worth more than most people's net worth, activist campaigns that never made the papers but changed entire industries. Richard always got a better deal than anyone else thought possible.
But I never stopped being "kiddo" to Michael. That's not what he called me all the time, of course, I go by Mojo now, have for years. But that's how it felt. Like I was his. Like I belonged to something bigger than myself.
When my daughter was born, I brought her to Miami so Michael could meet her. We met at the Ritz. He looked hollow, but his eyes lit up when he saw her.
"She looks like a fighter," he said. "She's got your eyes."
Then he hugged me. Longer than usual.
"You did it," he said.
He meant I'd become the person he saw in me from the beginning. Someone who could navigate his world, make the hard calls, be trusted with what mattered. I was no longer the kid from San Francisco trying not to say anything stupid.
A few months later, I was in Mexico. The phone rang. It was Greg, one of Michael's closest friends. I didn't even know he had my number.
When I saw his name, I knew.
I picked up. Tried to speak. Couldn't.
Greg didn't fill the silence. Just waited. Then he told me what had happened; Michael had a fall and had been in the hospital days earlier, but he didn't tell me because he didn't want to worry me.
"He talked about you a lot," he said eventually. "He was proud of you."
I walked outside. Stared at the light.
And cried.
I never cry.
At his celebration of life, the stories came from everywhere. CEOs shared podium time with his favorite Italian restaurant owner who doubled as a bartender. Business colleagues I'd only known as voices on conference calls stood alongside friends who'd known him for decades. They all said the same thing.
Michael saw them. Lifted them. Made them feel like they mattered. Everyone had a story. A moment. A lesson.
And I started to wonder, maybe I wasn't special. Maybe he just had that gift.
But then many came up to me.
"You're the one he always talked about."
"He said you were different."
"He said you were the one."
His sister, who I had only met in person once, sent me a 2 page email…
And that's when I knew.
The world I'd entered years earlier in that Hollywood producer's office had fundamentally changed me. Everything was different back then. Or maybe it's just that everything felt new when you're young enough to think the world is being created specifically for you. We had email, but used fax machines to close deals because that's how Richard liked it. We had three law firms on retainer: one for restructuring, one for IP, one so big their name alone scared people into moving faster.
Richard and Michael…they both died before Bitcoin, before social media changed everything. A different world entirely.
Some educations you pay for. Others pay you. This one did both.
Michael loved people. He collected them like other people collected art, and he'd send you books, dozens over the years. I still have mine, pages dog-eared and annotated in my handwriting from when I was young enough to think I could learn everything by reading it.
I learned more about human nature, about money, about power, about the distance between who we are and who we pretend to be in those few years than I learned in all the years before or since.
This is just the surface. There are stories I haven't told yet. The five questions that can crack open any room. Deals that shouldn't have worked but did. Moments that made me wonder what I'd really walked into.
Some of them I will share.
Mojo
You can find me on twitter at @MrMojoRisinX.