<ul>
<li>The odds you will get hit.</li>
<li>The average consequences of getting hit.</li>
<li>The tail-end consequences of getting hit.</li>
</ul>
The first two are easy to understand. It’s the third that’s hardest to learn, and can often only be learned through experience.

Three different sides of risk

Problem Solving

The tail-end consequences of an action or event (those with low-probability, high-impact) are all that matter.
In investing, the average consequences of risk make up most of the daily news headlines. But the tail-end consequences of risk (for example, pandemics and depressions) are what make the pages of history books.

The tail-end consequences

I grew up ski racing in Lake Tahoe. I was on the Squaw Valley Ski Team, and it was the center of my life for over a decade.At a conference a few months ago I was asked what skiing taught me about investing. This was on stage, where you can’t ponder your answer – you have to blurt out whatever you can think of.I didn’t think skiing taught me anything about investing. But one incident came to mind.“Well, let me take this to a dark and tragic place,” I said before telling a group of 500 strangers a story I hadn’t talked about much in almost 20 years.A dozen of us had grown up skiing together. Most had known each other since we were young children.By 2001 we were in our late teens, having spent the majority of our waking hours over the previous decade never far from each other. We skied six days a week, 10 months a year, spending summers on the glacier of Mt. Hood, Oregon and in New Zealand, where the seasons mirror our own. Skiing took precedence to everything. Most of us were in an independent study program that let us bypass traditional high school. After skiing all day we read a few books and filled out a few forms in the evening in what – to our amazement – led to a diploma.The amount of time we spent together created a relationship closer to siblings than friends. Ski racing is an odd hybrid between a team and individual sport. You train and travel and eat as a team, but the sport itself is individual. Our race results did not rely on each other; our daily sanity did.Any group of a dozen teenagers will find a way to butt heads. Half the time I think we hated each other. Twenty years later, few of us keep in touch.But of the dozen teenagers who, by 2001, I had spent the majority of my life with, four of us had become inseparable best friends.This is the story of two of them – Brendan Allan and Bryan Richmond.You take amazing things for granted when they become routine. Squaw Valley is one of the largest ski resorts in North America, was home to the 1960 Olympics, and attracts a million visitors a year. It’s staggeringly beautiful. To us, it was just an extension of home.Ski racing required four hours a day of training, which felt like work to us. The rest of the time – another four hours a day, six days a week – we just skied around, unstructured, having a good time. We called it “free skiing.” Everyone else just calls it skiing.On February 15th, 2001, we had just returned from a race in Colorado. Our flight home was delayed because Lake Tahoe was blasted with a blizzard vicious even by its own standards. You can’t race or train when there’s a blanket of new snow – racing requires hard-packed ice. So it was time for a week of free skiing.Earlier that month Tahoe received several feet of light, fluffy snow that comes from Arctic temperatures. The storm that hit in mid-February was different. It was warm – barely at the freezing point – and powerful, leaving three feet of heavy, wet snow on top of the light powder that came before it.We didn’t think about it at the time – we didn’t think about much at age 17 – but the combination of heavy snow on top of fluffy snow creates textbook perfect avalanche conditions.Imagine a thick layer of sand with a layer of heavy cement on top. Now imagine putting those layers on a steep hill. It’s fragile, prone to sliding down. That’s what Squaw Valley was like in late February 2001.Ski resorts are good at managing these kinds of conditions to keep people safe. Few tourists realize it, but if you visit a ski resort in the early morning hours after a blizzard you will hear what sounds like bombs going off. The sound isn’t deceiving. With a combination of mortars, grenades, and charges dropped from helicopters, ski patrol do controlled blasts of at-risk pitches to intentionally trigger avalanches when the resort is empty, preempting slides before guests arrive (check out some <a href="https://www.youtube.com/watch?v=-eQVY_KHR0A" dir="ltr">videos</a>).It’s an effective system, keeping avalanche accidents at major resorts rare.But if you’re skiing out of bounds – ducking under the DO NOT CROSS ropes to ski the forbidden terrain untouched by masses of Bay Area tourists – the system won’t help you.Skiing out of bounds is illegal, a form of trespassing. The main reason resorts don’t want you doing it is because it’s dangerous.Out-of-bounds areas aren’t patrolled, so you’re on your own if you get injured. They usually don’t lead down to a chairlift, so you have to find your own way back up.And they’re not bombed for avalanche control. So it’s here – out of bounds – that a skier is most likely to discover Mother Nature’s sliding wrath.On the morning of February 21st, 2001, Brendan, Bryan, and I met in the Squaw Valley Ski Team locker room, like we had hundreds of times before. Bryan’s mom told me years later that his last words when he left his house that morning were, “Don’t worry, Mom, I won’t ski out of bounds.”But as soon as we clicked into our skis, that’s what the three of us did.The backside of Squaw Valley, behind the KT-22 chairlift, is a stretch of mountain about a mile long that separates Squaw from Alpine Meadows ski resort.It’s good skiing – steep, wide open, with rolling terrain. And since it’s out of bounds, it was completely untouched. Our private playground.Before February 21st I had skied it maybe a dozen times. It wasn’t one of our frequent spots, because it’s a pain in the ass. The end of Squaw’s backside spits you out on a back country road, where we would hitchhike back to our locker room.Brendan, Bryan, and I decided to ski it that morning.When an event becomes life-changing, all kinds of mundane details sear into your memory. Almost 20 years later I remember Brendan duct-taping his ski pants shut on the chairlift because I had broken the side zipper while wearing them the week before. I remember Bryan cackling with joy as the three of us entered barren wilderness while the rest of the resort was packed with crowds.And I vividly remember getting hit by one of the only avalanches I’ve ever experienced.It was tiny, not going over my knees. It wasn’t scary. I remember laughing. But the feeling is unforgettable. I didn’t hear or see the slide. I just suddenly realized my skis weren’t on the ground anymore – I was literally floating in a cloud of snow. You have no control in these situations, because rather than pushing back on the snow to gain traction with your skis, the snow is pushing you. The best you can do is keep your balance to remain upright. I remember putting my hands up and shouting, “Wahooo” like I was on a roller coaster. I essentially was.The avalanche ended quickly. Brendan was to my left and Bryan was below us. No one stopped. We just charged to the bottom.“Holy shit, did you see that avalanche?” I remember saying when we got to the road.“Haha, that was awesome.” Brendan said. No one thought much more of it.We hitchhiked back. At first we had trouble getting a car to pick us up, so I decided if we took our shirts off in the 20-degree weather people would have sympathy for us and stop. It actually worked. Seventeen-year-old boys are resourceful.When we got back to Squaw Brendan and Bryan said they wanted to ski the backside again.I have no recollection of why, or how this came about, but I didn’t want to go.It may have been the hitchhiking, which I always hated. That, more than the out-of-bounds skiing, felt reckless to me.But I had an idea. Brendan and Bryan could ski the backside themselves. Rather than hitchhiking back, I would pick them up in my truck.Everyone agreed on the plan, which we made in the Wildflour Baking Company cookie shop in the Squaw Valley lodge after lunch. This was before we had cell phones, so syncing on concrete plans ahead of time was important.Brendan and Bryan walked out and skied off.Thirty minutes after Brendan and Bryan took the chair up to ski the backside, I drove to the back-country road where I was scheduled to pick them up.They weren’t there.I waited another 30 minutes before giving up. It took maybe five minutes to ski the pitch, so I knew they weren’t coming. It didn’t occur to me that they were in danger. I figured they beat me to the bottom and hitchhiked back.I drove back to our locker room, expecting to find them. They weren’t there, either. I asked around. No one had seen them.I drove to Brendan’s house, which wasn’t far from the pick-up point. No one was home. I drove back to the locker room and called his house. It went to voicemail. I remember ending the message with, “I hope you’re OK man.”I was starting to get nervous, but not enough to make a big deal. People were more comfortable being out of touch before the texting era.Later that day, around 4 pm, Bryan’s mom called me at home. I remember every word.“Hi Morgan, Bryan didn’t show up for work. Do you know where he is?” she asked.I told her the truth. “We skied the backside of KT-22 this morning. He and Brendan did it again, I was going to pick them up on the road. But they weren’t there, and I haven’t seen them since.”“Oh my God,” she said. Click.I think in that moment she pieced together what may have happened to her son. I did, too.Later that evening, after sunset, my friend Ahren and I bought heavy duty flashlights at a drug store and drove to the pick-up spot. We shined the lights up the mountain shouting, “Brennnndan …. Bryyyyyan.” I remember Ahren and I thinking they had likely broken their legs and were stuck on the hill. In the back of my mind I knew it was more serious, but it was comforting to think we could find them.We gave up quickly and drove to the locker room.I forget who made the call, but the police were suddenly taking our information in what had become a missing-person report.I don’t fault the police for this, but they didn’t take it seriously. I remember one saying, “99% of the time in cases like these the person is out drunk at a party, or ran off with a girl for the night.” I’m sure he was right – that was usually the case. But I knew he was wrong.“Their shoes are right there,” I said, pointing to Brendan and Bryan’s sneakers on the locker room floor. “That means their ski boots are on their feet. And it’s now 9 pm. Think about that. It’s 9 pm and they have their ski boots on their feet. They are not at a party.”Around 10 pm I was told to go to the Squaw Valley Fire Department where I met the local search and rescue team. They took it much more seriously.I explained everything Brendan, Bryan, and I did that day. The search team pulled out maps, and I showed them exactly where we entered the out-of-bounds area, where we exited, and the path we took. I told them about the small avalanche we were caught in that morning. As soon as I mentioned it I could see the dots connecting in the rescuers’ heads. These were seasoned professionals who understood the danger of mountains. When I finished talking I remember two of the rescuers looked at each other and sighed. They knew.I drove back to the locker room around midnight. The Squaw Valley parking lot can hold several thousand cars. By this time it was almost empty. Everyone had gone home, except two cars parked next to each other: Brendan’s Jeep, and Bryan’s Chevy pickup.Search and rescue teams were on the backside of Squaw a little after midnight. It was still a blizzard, with gusty winds and low visibility even during daylight. I remember watching them ski off in the pitchblack night.With giant floodlights and a team of search dogs, they went looking for Brendan and Bryan.I later learned that as soon as the rescue team entered the out-of-bounds point where I told them we skied, they found the fresh scars of a massive avalanche field.I tried to sleep on a bench in the locker room, but couldn’t shut my eyes. I remember hoping Brendan and Bryan would come bounding through the door. The hours dragged on, and felt like days.By 9 am the locker room was packed with other ski racers, parents, friends, and family, all eager to help. It became a staging area for the search.I laid back down on the bench and finally fell asleep. A few minutes later I awoke to the sound of a scream, followed by yelling and commotion.I knew what happened. No one needed to say it.I walked to the second floor of the locker room where I saw Bryan’s mom on a couch. The scream was hers. “I’m so sorry,” I told her, bawling. It’s hard to describe a moment like that. I didn’t know what else to say then. I don’t know what else to say now.Search dogs had honed in on a spot in the avalanche field where rescuers with probe poles found Brendan and Bryan buried under six feet of snow.They were born one day apart, and died 10 feet from each other.Later that day I drove to see my dad at work. I wanted to be around family. He met me in the parking lot and said, “I’ve never been so happy to see you.” It was the only time I’ve seen him cry.It didn’t occur to me until that moment how close I was to going with Brendan and Bryan.Why did I ski the backside with them once that morning, but then decline a second run?I’ve thought about it a million times. I have no idea.Why was the avalanche on our first run a tiny little thrill, but the second run triggered a massive slide that killed two 17-year-olds?We’ll never know.The next evening, Tom Brokaw told Brendan and Bryan’s story on the NBC Nightly News. It was surreal to watch. We were laughing together 36 hours before. Now their death was national news. And the only thing that kept me from being a third name in the newscast I had watched religiously was a fluke decision I put no thought into.It’s been almost 20 years since this happened. Sometimes I think about everything that’s occurred since – college, marriage, career, kids – and remind myself that I’ve only experienced it because of a blind, thoughtless decision to decline another ski run.This story isn’t unique. Many people reading this have had near-death experiences. Most have lost someone dear to them. And everyone reading this has made what seemed like know-nothing, inconsequential decisions that fundamentally reshaped their lives. Sometimes those fluke decisions are positive. Sometimes they’re negative. But they’re always out of the blue, unforeseeable. It’s just how life works.After I told this story at the conference I had to tie it back to an investing lesson. It was easier than I thought.My risk tolerance plunged after Brendan and Bryan died. I broke my back skiing (no nerve damage) a few months later, which crushed it even more. I haven’t skied much since. Maybe ten times in the last 15 years. If I’m honest, it scares me.I’ve been risk-averse in other areas of life ever since, too. I drive the speed limit. I obey the seatbelt sign on airplanes. I invest in index funds.I don’t know if Brendan and Bryan’s death actually affected how I invest. But it opened my eyes to the idea that there are three distinct sides of risk:<UL><LI>The odds you will get hit.</LI><LI>The average consequences of getting hit.</LI><LI>The tail-end consequences of getting hit.</LI></UL>The first two are easy to grasp. It’s the third that’s hardest to learn, and can often only be learned through experience.We knew we were taking risks when we skied. We knew that going out of bounds was wrong, and that we might get caught. But at 17 years old we figured the consequences of risk meant our coaches might yell at us. Maybe we’d get our season pass revoked for the year.Never, not once, did we think we’d pay the ultimate price.But once you go through something like that, you realize that the tail-end consequences – the low-probability, high-impact events – are all that matter.In investing, the average consequences of risk make up most of the daily news headlines. But the tail-end consequences of risk – like pandemics, and depressions – are what make the pages of history books. They’re all that matter. They’re all you should focus on. We spent the last decade debating whether economic risk meant the Federal Reserve set interest rates at 0.25% or 0.5%. Then 36 million people lost their jobs in two months because of a virus. It’s absurd.Tail-end events are all that matter.Once you experience it, you’ll never think otherwise.<figure><img src="https://www.collaborativefund.com/uploads/Brendan%20&amp;%20Bryan.JPG" alt="Brendan &amp; Bryan.JPG" width="714" height="448"></figure>

I grew up ski racing in Lake Tahoe. I was on the Squaw Valley Ski Team, and it was the center of my life for over a decade. At a conference a few months ago I was asked what skiing taught me about investing. This was on stage, where you can’t ponder your answer – you have to blurt out whatever you can think of. I didn’t think skiing taught me anything about investing. But one incident came to mind. “Well, let me take this to a dark and tragic place,” I said before telling a group of 500 strangers a story I hadn’t talked about much in almost 20 years. A dozen of us had grown up skiing together. Most had known each other since we were young children. By 2001 we were in our late teens, having spent the majority of our waking hours over the previous decade never far from each other. We skied six days a week, 10 months a year, spending summers on the glacier of Mt. Hood, Oregon and in New Zealand, where the seasons mirror our own. Skiing took precedence to everything. Most of us were in an independent study program that let us bypass traditional high school. After skiing all day we read a few books and filled out a few forms in the evening in what – to our amazement – led to a diploma. The amount of time we spent together created a relationship closer to siblings than friends. Ski racing is an odd hybrid between a team and individual sport. You train and travel and eat as a team, but the sport itself is individual. Our race results did not rely on each other; our daily sanity did. Any group of a dozen teenagers will find a way to butt heads. Half the time I think we hated each other. Twenty years later, few of us keep in touch. But of the dozen teenagers who, by 2001, I had spent the majority of my life with, four of us had become inseparable best friends. This is the story of two of them – Brendan Allan and Bryan Richmond. You take amazing things for granted when they become routine. Squaw Valley is one of the largest ski resorts in North America, was home to the 1960 Olympics, and attracts a million visitors a year. It’s staggeringly beautiful. To us, it was just an extension of home. Ski racing required four hours a day of training, which felt like work to us. The rest of the time – another four hours a day, six days a week – we just skied around, unstructured, having a good time. We called it “free skiing.” Everyone else just calls it skiing. On February 15th, 2001, we had just returned from a race in Colorado. Our flight home was delayed because Lake Tahoe was blasted with a blizzard vicious even by its own standards. You can’t race or train when there’s a blanket of new snow – racing requires hard-packed ice. So it was time for a week of free skiing. Earlier that month Tahoe received several feet of light, fluffy snow that comes from Arctic temperatures. The storm that hit in mid-February was different. It was warm – barely at the freezing point – and powerful, leaving three feet of heavy, wet snow on top of the light powder that came before it. We didn’t think about it at the time – we didn’t think about much at age 17 – but the combination of heavy snow on top of fluffy snow creates textbook perfect avalanche conditions. Imagine a thick layer of sand with a layer of heavy cement on top. Now imagine putting those layers on a steep hill. It’s fragile, prone to sliding down. That’s what Squaw Valley was like in late February 2001. Ski resorts are good at managing these kinds of conditions to keep people safe. Few tourists realize it, but if you visit a ski resort in the early morning hours after a blizzard you will hear what sounds like bombs going off. The sound isn’t deceiving. With a combination of mortars, grenades, and charges dropped from helicopters, ski patrol do controlled blasts of at-risk pitches to intentionally trigger avalanches when the resort is empty, preempting slides before guests arrive (check out some videos). It’s an effective system, keeping avalanche accidents at major resorts rare. But if you’re skiing out of bounds – ducking under the DO NOT CROSS ropes to ski the forbidden terrain untouched by masses of Bay Area tourists – the system won’t help you. Skiing out of bounds is illegal, a form of trespassing. The main reason resorts don’t want you doing it is because it’s dangerous. Out-of-bounds areas aren’t patrolled, so you’re on your own if you get injured. They usually don’t lead down to a chairlift, so you have to find your own way back up. And they’re not bombed for avalanche control. So it’s here – out of bounds – that a skier is most likely to discover Mother Nature’s sliding wrath. On the morning of February 21st, 2001, Brendan, Bryan, and I met in the Squaw Valley Ski Team locker room, like we had hundreds of times before. Bryan’s mom told me years later that his last words when he left his house that morning were, “Don’t worry, Mom, I won’t ski out of bounds.” But as soon as we clicked into our skis, that’s what the three of us did. The backside of Squaw Valley, behind the KT-22 chairlift, is a stretch of mountain about a mile long that separates Squaw from Alpine Meadows ski resort. It’s good skiing – steep, wide open, with rolling terrain. And since it’s out of bounds, it was completely untouched. Our private playground. Before February 21st I had skied it maybe a dozen times. It wasn’t one of our frequent spots, because it’s a pain in the ass. The end of Squaw’s backside spits you out on a back country road, where we would hitchhike back to our locker room. Brendan, Bryan, and I decided to ski it that morning. When an event becomes life-changing, all kinds of mundane details sear into your memory. Almost 20 years later I remember Brendan duct-taping his ski pants shut on the chairlift because I had broken the side zipper while wearing them the week before. I remember Bryan cackling with joy as the three of us entered barren wilderness while the rest of the resort was packed with crowds. And I vividly remember getting hit by one of the only avalanches I’ve ever experienced. It was tiny, not going over my knees. It wasn’t scary. I remember laughing. But the feeling is unforgettable. I didn’t hear or see the slide. I just suddenly realized my skis weren’t on the ground anymore – I was literally floating in a cloud of snow. You have no control in these situations, because rather than pushing back on the snow to gain traction with your skis, the snow is pushing you. The best you can do is keep your balance to remain upright. I remember putting my hands up and shouting, “Wahooo” like I was on a roller coaster. I essentially was. The avalanche ended quickly. Brendan was to my left and Bryan was below us. No one stopped. We just charged to the bottom. “Holy shit, did you see that avalanche?” I remember saying when we got to the road. “Haha, that was awesome.” Brendan said. No one thought much more of it. We hitchhiked back. At first we had trouble getting a car to pick us up, so I decided if we took our shirts off in the 20-degree weather people would have sympathy for us and stop. It actually worked. Seventeen-year-old boys are resourceful. When we got back to Squaw Brendan and Bryan said they wanted to ski the backside again. I have no recollection of why, or how this came about, but I didn’t want to go. It may have been the hitchhiking, which I always hated. That, more than the out-of-bounds skiing, felt reckless to me. But I had an idea. Brendan and Bryan could ski the backside themselves. Rather than hitchhiking back, I would pick them up in my truck. Everyone agreed on the plan, which we made in the Wildflour Baking Company cookie shop in the Squaw Valley lodge after lunch. This was before we had cell phones, so syncing on concrete plans ahead of time was important. Brendan and Bryan walked out and skied off. Thirty minutes after Brendan and Bryan took the chair up to ski the backside, I drove to the back-country road where I was scheduled to pick them up. They weren’t there. I waited another 30 minutes before giving up. It took maybe five minutes to ski the pitch, so I knew they weren’t coming. It didn’t occur to me that they were in danger. I figured they beat me to the bottom and hitchhiked back. I drove back to our locker room, expecting to find them. They weren’t there, either. I asked around. No one had seen them. I drove to Brendan’s house, which wasn’t far from the pick-up point. No one was home. I drove back to the locker room and called his house. It went to voicemail. I remember ending the message with, “I hope you’re OK man.” I was starting to get nervous, but not enough to make a big deal. People were more comfortable being out of touch before the texting era. Later that day, around 4 pm, Bryan’s mom called me at home. I remember every word. “Hi Morgan, Bryan didn’t show up for work. Do you know where he is?” she asked. I told her the truth. “We skied the backside of KT-22 this morning. He and Brendan did it again, I was going to pick them up on the road. But they weren’t there, and I haven’t seen them since.” “Oh my God,” she said. Click. I think in that moment she pieced together what may have happened to her son. I did, too. Later that evening, after sunset, my friend Ahren and I bought heavy duty flashlights at a drug store and drove to the pick-up spot. We shined the lights up the mountain shouting, “Brennnndan …. Bryyyyyan.” I remember Ahren and I thinking they had likely broken their legs and were stuck on the hill. In the back of my mind I knew it was more serious, but it was comforting to think we could find them. We gave up quickly and drove to the locker room. I forget who made the call, but the police were suddenly taking our information in what had become a missing-person report. I don’t fault the police for this, but they didn’t take it seriously. I remember one saying, “99% of the time in cases like these the person is out drunk at a party, or ran off with a girl for the night.” I’m sure he was right – that was usually the case. But I knew he was wrong. “Their shoes are right there,” I said, pointing to Brendan and Bryan’s sneakers on the locker room floor. “That means their ski boots are on their feet. And it’s now 9 pm. Think about that. It’s 9 pm and they have their ski boots on their feet. They are not at a party.” Around 10 pm I was told to go to the Squaw Valley Fire Department where I met the local search and rescue team. They took it much more seriously. I explained everything Brendan, Bryan, and I did that day. The search team pulled out maps, and I showed them exactly where we entered the out-of-bounds area, where we exited, and the path we took. I told them about the small avalanche we were caught in that morning. As soon as I mentioned it I could see the dots connecting in the rescuers’ heads. These were seasoned professionals who understood the danger of mountains. When I finished talking I remember two of the rescuers looked at each other and sighed. They knew. I drove back to the locker room around midnight. The Squaw Valley parking lot can hold several thousand cars. By this time it was almost empty. Everyone had gone home, except two cars parked next to each other: Brendan’s Jeep, and Bryan’s Chevy pickup. Search and rescue teams were on the backside of Squaw a little after midnight. It was still a blizzard, with gusty winds and low visibility even during daylight. I remember watching them ski off in the pitchblack night. With giant floodlights and a team of search dogs, they went looking for Brendan and Bryan. I later learned that as soon as the rescue team entered the out-of-bounds point where I told them we skied, they found the fresh scars of a massive avalanche field. I tried to sleep on a bench in the locker room, but couldn’t shut my eyes. I remember hoping Brendan and Bryan would come bounding through the door. The hours dragged on, and felt like days. By 9 am the locker room was packed with other ski racers, parents, friends, and family, all eager to help. It became a staging area for the search. I laid back down on the bench and finally fell asleep. A few minutes later I awoke to the sound of a scream, followed by yelling and commotion. I knew what happened. No one needed to say it. I walked to the second floor of the locker room where I saw Bryan’s mom on a couch. The scream was hers. “I’m so sorry,” I told her, bawling. It’s hard to describe a moment like that. I didn’t know what else to say then. I don’t know what else to say now. Search dogs had honed in on a spot in the avalanche field where rescuers with probe poles found Brendan and Bryan buried under six feet of snow. They were born one day apart, and died 10 feet from each other. Later that day I drove to see my dad at work. I wanted to be around family. He met me in the parking lot and said, “I’ve never been so happy to see you.” It was the only time I’ve seen him cry. It didn’t occur to me until that moment how close I was to going with Brendan and Bryan. Why did I ski the backside with them once that morning, but then decline a second run? I’ve thought about it a million times. I have no idea. Why was the avalanche on our first run a tiny little thrill, but the second run triggered a massive slide that killed two 17-year-olds? We’ll never know. The next evening, Tom Brokaw told Brendan and Bryan’s story on the NBC Nightly News. It was surreal to watch. We were laughing together 36 hours before. Now their death was national news. And the only thing that kept me from being a third name in the newscast I had watched religiously was a fluke decision I put no thought into. It’s been almost 20 years since this happened. Sometimes I think about everything that’s occurred since – college, marriage, career, kids – and remind myself that I’ve only experienced it because of a blind, thoughtless decision to decline another ski run. This story isn’t unique. Many people reading this have had near-death experiences. Most have lost someone dear to them. And everyone reading this has made what seemed like know-nothing, inconsequential decisions that fundamentally reshaped their lives. Sometimes those fluke decisions are positive. Sometimes they’re negative. But they’re always out of the blue, unforeseeable. It’s just how life works. After I told this story at the conference I had to tie it back to an investing lesson. It was easier than I thought. My risk tolerance plunged after Brendan and Bryan died. I broke my back skiing (no nerve damage) a few months later, which crushed it even more. I haven’t skied much since. Maybe ten times in the last 15 years. If I’m honest, it scares me. I’ve been risk-averse in other areas of life ever since, too. I drive the speed limit. I obey the seatbelt sign on airplanes. I invest in index funds. I don’t know if Brendan and Bryan’s death actually affected how I invest. But it opened my eyes to the idea that there are three distinct sides of risk: The odds you will get hit. The average consequences of getting hit. The tail-end consequences of getting hit. The first two are easy to grasp. It’s the third that’s hardest to learn, and can often only be learned through experience. We knew we were taking risks when we skied. We knew that going out of bounds was wrong, and that we might get caught. But at 17 years old we figured the consequences of risk meant our coaches might yell at us. Maybe we’d get our season pass revoked for the year. Never, not once, did we think we’d pay the ultimate price. But once you go through something like that, you realize that the tail-end consequences – the low-probability, high-impact events – are all that matter. In investing, the average consequences of risk make up most of the daily news headlines. But the tail-end consequences of risk – like pandemics, and depressions – are what make the pages of history books. They’re all that matter. They’re all you should focus on. We spent the last decade debating whether economic risk meant the Federal Reserve set interest rates at 0.25% or 0.5%. Then 36 million people lost their jobs in two months because of a virus. It’s absurd. Tail-end events are all that matter. Once you experience it, you’ll never think otherwise.

I grew up ski racing in Lake Tahoe. I was on the Squaw Valley Ski Team, and it was the center of my life for over a decade.

At a conference a few months ago I was asked what skiing taught me about investing. This was on stage, where you can’t ponder your answer – you have to blurt out whatever you can think of.

I didn’t think skiing taught me anything about investing. But one incident came to mind.

“Well, let me take this to a dark and tragic place,” I said before telling a group of 500 strangers a story I hadn’t talked about much in almost 20 years.

A dozen of us had grown up skiing together. Most had known each other since we were young children.

By 2001 we were in our late teens, having spent the majority of our waking hours over the previous decade never far from each other. We skied six days a week, 10 months a year, spending summers on the glacier of Mt. Hood, Oregon and in New Zealand, where the seasons mirror our own. Skiing took precedence to everything. Most of us were in an independent study program that let us bypass traditional high school. After skiing all day we read a few books and filled out a few forms in the evening in what – to our amazement – led to a diploma.

The amount of time we spent together created a relationship closer to siblings than friends. Ski racing is an odd hybrid between a team and individual sport. You train and travel and eat as a team, but the sport itself is individual. Our race results did not rely on each other; our daily sanity did.

Any group of a dozen teenagers will find a way to butt heads. Half the time I think we hated each other. Twenty years later, few of us keep in touch.

But of the dozen teenagers who, by 2001, I had spent the majority of my life with, four of us had become inseparable best friends.

This is the story of two of them – Brendan Allan and Bryan Richmond.

You take amazing things for granted when they become routine. Squaw Valley is one of the largest ski resorts in North America, was home to the 1960 Olympics, and attracts a million visitors a year. It’s staggeringly beautiful. To us, it was just an extension of home.

Ski racing required four hours a day of training, which felt like work to us. The rest of the time – another four hours a day, six days a week – we just skied around, unstructured, having a good time. We called it “free skiing.” Everyone else just calls it skiing.

On February 15th, 2001, we had just returned from a race in Colorado. Our flight home was delayed because Lake Tahoe was blasted with a blizzard vicious even by its own standards. You can’t race or train when there’s a blanket of new snow – racing requires hard-packed ice. So it was time for a week of free skiing.

Earlier that month Tahoe received several feet of light, fluffy snow that comes from Arctic temperatures. The storm that hit in mid-February was different. It was warm – barely at the freezing point – and powerful, leaving three feet of heavy, wet snow on top of the light powder that came before it.

We didn’t think about it at the time – we didn’t think about much at age 17 – but the combination of heavy snow on top of fluffy snow creates textbook perfect avalanche conditions.

Imagine a thick layer of sand with a layer of heavy cement on top. Now imagine putting those layers on a steep hill. It’s fragile, prone to sliding down. That’s what Squaw Valley was like in late February 2001.

Ski resorts are good at managing these kinds of conditions to keep people safe. Few tourists realize it, but if you visit a ski resort in the early morning hours after a blizzard you will hear what sounds like bombs going off. The sound isn’t deceiving. With a combination of mortars, grenades, and charges dropped from helicopters, ski patrol do controlled blasts of at-risk pitches to intentionally trigger avalanches when the resort is empty, preempting slides before guests arrive (check out some <a dir="ltr" href="https://www.youtube.com/watch?v=-eQVY_KHR0A">videos </a>).

It’s an effective system, keeping avalanche accidents at major resorts rare.

But if you’re skiing out of bounds – ducking under the DO NOT CROSS ropes to ski the forbidden terrain untouched by masses of Bay Area tourists – the system won’t help you.

Skiing out of bounds is illegal, a form of trespassing. The main reason resorts don’t want you doing it is because it’s dangerous.

Out-of-bounds areas aren’t patrolled, so you’re on your own if you get injured. They usually don’t lead down to a chairlift, so you have to find your own way back up.

And they’re not bombed for avalanche control. So it’s here – out of bounds – that a skier is most likely to discover Mother Nature’s sliding wrath.

On the morning of February 21st, 2001, Brendan, Bryan, and I met in the Squaw Valley Ski Team locker room, like we had hundreds of times before. Bryan’s mom told me years later that his last words when he left his house that morning were, “Don’t worry, Mom, I won’t ski out of bounds.”

But as soon as we clicked into our skis, that’s what the three of us did.

The backside of Squaw Valley, behind the KT-22 chairlift, is a stretch of mountain about a mile long that separates Squaw from Alpine Meadows ski resort.

It’s good skiing – steep, wide open, with rolling terrain. And since it’s out of bounds, it was completely untouched. Our private playground.

Before February 21st I had skied it maybe a dozen times. It wasn’t one of our frequent spots, because it’s a pain in the ass. The end of Squaw’s backside spits you out on a back country road, where we would hitchhike back to our locker room.

Brendan, Bryan, and I decided to ski it that morning.

When an event becomes life-changing, all kinds of mundane details sear into your memory. Almost 20 years later I remember Brendan duct-taping his ski pants shut on the chairlift because I had broken the side zipper while wearing them the week before. I remember Bryan cackling with joy as the three of us entered barren wilderness while the rest of the resort was packed with crowds.

And I vividly remember getting hit by one of the only avalanches I’ve ever experienced.

It was tiny, not going over my knees. It wasn’t scary. I remember laughing. But the feeling is unforgettable. I didn’t hear or see the slide. I just suddenly realized my skis weren’t on the ground anymore – I was literally floating in a cloud of snow. You have no control in these situations, because rather than pushing back on the snow to gain traction with your skis, the snow is pushing you. The best you can do is keep your balance to remain upright. I remember putting my hands up and shouting, “Wahooo” like I was on a roller coaster. I essentially was.

The avalanche ended quickly. Brendan was to my left and Bryan was below us. No one stopped. We just charged to the bottom.

“Holy shit, did you see that avalanche?” I remember saying when we got to the road.

“Haha, that was awesome.” Brendan said. No one thought much more of it.

We hitchhiked back. At first we had trouble getting a car to pick us up, so I decided if we took our shirts off in the 20-degree weather people would have sympathy for us and stop. It actually worked. Seventeen-year-old boys are resourceful.

When we got back to Squaw Brendan and Bryan said they wanted to ski the backside again.

I have no recollection of why, or how this came about, but I didn’t want to go.

It may have been the hitchhiking, which I always hated. That, more than the out-of-bounds skiing, felt reckless to me.

But I had an idea. Brendan and Bryan could ski the backside themselves. Rather than hitchhiking back, I would pick them up in my truck.

Everyone agreed on the plan, which we made in the Wildflour Baking Company cookie shop in the Squaw Valley lodge after lunch. This was before we had cell phones, so syncing on concrete plans ahead of time was important.

Brendan and Bryan walked out and skied off.

Thirty minutes after Brendan and Bryan took the chair up to ski the backside, I drove to the back-country road where I was scheduled to pick them up.

I waited another 30 minutes before giving up. It took maybe five minutes to ski the pitch, so I knew they weren’t coming. It didn’t occur to me that they were in danger. I figured they beat me to the bottom and hitchhiked back.

I drove back to our locker room, expecting to find them. They weren’t there, either. I asked around. No one had seen them.

I drove to Brendan’s house, which wasn’t far from the pick-up point. No one was home. I drove back to the locker room and called his house. It went to voicemail. I remember ending the message with, “I hope you’re OK man.”

I was starting to get nervous, but not enough to make a big deal. People were more comfortable being out of touch before the texting era.

Later that day, around 4 pm, Bryan’s mom called me at home. I remember every word.

“Hi Morgan, Bryan didn’t show up for work. Do you know where he is?” she asked.

I told her the truth. “We skied the backside of KT-22 this morning. He and Brendan did it again, I was going to pick them up on the road. But they weren’t there, and I haven’t seen them since.”

“Oh my God,” she said. Click.

I think in that moment she pieced together what may have happened to her son. I did, too.

Later that evening, after sunset, my friend Ahren and I bought heavy duty flashlights at a drug store and drove to the pick-up spot. We shined the lights up the mountain shouting, “Brennnndan …. Bryyyyyan.” I remember Ahren and I thinking they had likely broken their legs and were stuck on the hill. In the back of my mind I knew it was more serious, but it was comforting to think we could find them.

We gave up quickly and drove to the locker room.

I forget who made the call, but the police were suddenly taking our information in what had become a missing-person report.

I don’t fault the police for this, but they didn’t take it seriously. I remember one saying, “99% of the time in cases like these the person is out drunk at a party, or ran off with a girl for the night.” I’m sure he was right – that was usually the case. But I knew he was wrong.

“Their shoes are right there,” I said, pointing to Brendan and Bryan’s sneakers on the locker room floor. “That means their ski boots are on their feet. And it’s now 9 pm. Think about that. It’s 9 pm and they have their ski boots on their feet. They are not at a party.”

Around 10 pm I was told to go to the Squaw Valley Fire Department where I met the local search and rescue team. They took it much more seriously.

I explained everything Brendan, Bryan, and I did that day. The search team pulled out maps, and I showed them exactly where we entered the out-of-bounds area, where we exited, and the path we took. I told them about the small avalanche we were caught in that morning. As soon as I mentioned it I could see the dots connecting in the rescuers’ heads. These were seasoned professionals who understood the danger of mountains. When I finished talking I remember two of the rescuers looked at each other and sighed. They knew.

I drove back to the locker room around midnight. The Squaw Valley parking lot can hold several thousand cars. By this time it was almost empty. Everyone had gone home, except two cars parked next to each other: Brendan’s Jeep, and Bryan’s Chevy pickup.

Search and rescue teams were on the backside of Squaw a little after midnight. It was still a blizzard, with gusty winds and low visibility even during daylight. I remember watching them ski off in the pitchblack night.

With giant floodlights and a team of search dogs, they went looking for Brendan and Bryan.

I later learned that as soon as the rescue team entered the out-of-bounds point where I told them we skied, they found the fresh scars of a massive avalanche field.

I tried to sleep on a bench in the locker room, but couldn’t shut my eyes. I remember hoping Brendan and Bryan would come bounding through the door. The hours dragged on, and felt like days.

By 9 am the locker room was packed with other ski racers, parents, friends, and family, all eager to help. It became a staging area for the search.

I laid back down on the bench and finally fell asleep. A few minutes later I awoke to the sound of a scream, followed by yelling and commotion.

I knew what happened. No one needed to say it.

I walked to the second floor of the locker room where I saw Bryan’s mom on a couch. The scream was hers. “I’m so sorry,” I told her, bawling. It’s hard to describe a moment like that. I didn’t know what else to say then. I don’t know what else to say now.

Search dogs had honed in on a spot in the avalanche field where rescuers with probe poles found Brendan and Bryan buried under six feet of snow.

They were born one day apart, and died 10 feet from each other.

Later that day I drove to see my dad at work. I wanted to be around family. He met me in the parking lot and said, “I’ve never been so happy to see you.” It was the only time I’ve seen him cry.

It didn’t occur to me until that moment how close I was to going with Brendan and Bryan.

Why did I ski the backside with them once that morning, but then decline a second run?

I’ve thought about it a million times. I have no idea.

Why was the avalanche on our first run a tiny little thrill, but the second run triggered a massive slide that killed two 17-year-olds?

The next evening, Tom Brokaw told Brendan and Bryan’s story on the NBC Nightly News. It was surreal to watch. We were laughing together 36 hours before. Now their death was national news. And the only thing that kept me from being a third name in the newscast I had watched religiously was a fluke decision I put no thought into.

It’s been almost 20 years since this happened. Sometimes I think about everything that’s occurred since – college, marriage, career, kids – and remind myself that I’ve only experienced it because of a blind, thoughtless decision to decline another ski run.

This story isn’t unique. Many people reading this have had near-death experiences. Most have lost someone dear to them. And everyone reading this has made what seemed like know-nothing, inconsequential decisions that fundamentally reshaped their lives. Sometimes those fluke decisions are positive. Sometimes they’re negative. But they’re always out of the blue, unforeseeable. It’s just how life works.

After I told this story at the conference I had to tie it back to an investing lesson. It was easier than I thought.

My risk tolerance plunged after Brendan and Bryan died. I broke my back skiing (no nerve damage) a few months later, which crushed it even more. I haven’t skied much since. Maybe ten times in the last 15 years. If I’m honest, it scares me.

I’ve been risk-averse in other areas of life ever since, too. I drive the speed limit. I obey the seatbelt sign on airplanes. I invest in index funds.

I don’t know if Brendan and Bryan’s death actually affected how I invest. But it opened my eyes to the idea that there are three distinct sides of risk:

<ul><li>The odds you will get hit. </li><li>The average consequences of getting hit. </li><li>The tail-end consequences of getting hit. </li> </ul>

The first two are easy to grasp. It’s the third that’s hardest to learn, and can often only be learned through experience.

We knew we were taking risks when we skied. We knew that going out of bounds was wrong, and that we might get caught. But at 17 years old we figured the consequences of risk meant our coaches might yell at us. Maybe we’d get our season pass revoked for the year.

Never, not once, did we think we’d pay the ultimate price.

But once you go through something like that, you realize that the tail-end consequences – the low-probability, high-impact events – are all that matter.

In investing, the average consequences of risk make up most of the daily news headlines. But the tail-end consequences of risk – like pandemics, and depressions – are what make the pages of history books. They’re all that matter . They’re all you should focus on. We spent the last decade debating whether economic risk meant the Federal Reserve set interest rates at 0.25% or 0.5%. Then 36 million people lost their jobs in two months because of a virus. It’s absurd.

Tail-end events are all that matter.

Once you experience it, you’ll never think otherwise.

Bite‑sized knowledge
to upgrade
your career

The Three Sides of Risk

Three different sides of risk

The tail-end consequences

Where did skiing come from?

Can a Worry Journal Help You Manage Stress?

Want to Improve? Ask Yourself These Two Questions

Bite‑sized knowledgeto upgradeyour career

The Three Sides of Risk

Three different sides of risk

The tail-end consequences

Where did skiing come from?

Can a Worry Journal Help You Manage Stress?

Want to Improve? Ask Yourself These Two Questions

Bite‑sized knowledge
to upgrade
your career