His Ship Sank. All 27 Men Survived. Here's What That Says About Leadership.

November 21st, 1915. Antarctica. Ernest Shackleton is standing on the ice watching his ship sink. The expedition is over before it ever started. Twenty-seven men are stranded over a thousand miles from any other human being with no radio, no rescue coming, and no plan left to follow.

What he said in that moment, and what he did over the next nineteen months, is one of the most extraordinary leadership stories in human history. And almost nobody knows it.

This episode is the story of Shackleton's Endurance expedition, told alongside a real estate deal that collapsed one hour before closing after two months of fighting to make it happen. Both stories ask the same question: what kind of person are you when the thing you built, planned, and believed in goes down in front of you?

Andrew unpacks why Shackleton consistently appears on lists of the greatest leaders who ever lived despite never completing his mission, what he understood about morale and human nature that most leaders never figure out, and why the mission falling apart is sometimes the thing that keeps you safe. It just takes time to see it that way.

The ship is going to go down. The question isn't whether you can stop it. The question is what you say when it does.

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Transcript

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It's November 21st, 1915. Antarctica, the Weddell Sea, and Ernest Shackleton is standing on the ice watching his ship sink. The endurance, his free massed wooden ship named after his family motto, for the two nine Vinc, by endurance we conquer, is being swallowed by the frozen sea. The ice had been crushing the hall for months, croaking and greening, slowly giving way. And then someone on board yells, She's going, boys, and she goes. Mast, cargo, supplies, everything. Gone. Down to the bottom of the Weddell Sea. Shackleton had been at sea for over a year. He had 27 men with him. They were over a thousand miles away from any other human beings. There was no radio signal to call for help, no helicopter coming, no GPS, no weather app, no Gore-Tex, nothing. And the mission, the whole reason they were there, the first overland crossing of the entire Antarctic continent. That was now finished before it even started. Here's what Shackleton said when it was done. Ship and stores have gone, so now we'll go home. One sentence that he shared with only a few men standing beside him on the ice, yet it has echoed in a century later. About two years ago, I was working on the biggest real estate deal of my life, a 19-suite apartment building, just over $2 million. I had done multiple deals by that point, flips, smaller rentals, the birth strategy, but nothing close to this size. And when I ran the numbers, I really sat down and stress tested them. The potential return on investment was 57.4%. Life-changing numbers, the kind of numbers that make you nervous just saying them out loud. And I was nervous the whole time, every step of the way, I kept second-guessing myself. Not because the numbers were wrong, because the scale was new, because I had never played at this level before. And some part of me kept waiting to be exposed as someone who didn't belong there. But every time a door closed, I'd sit with it, think it over, find a different angle. We kept getting creative, kept pushing, and eventually started getting partners invested. Real traction. The deal was alive. We got it to the final day, closing day. And one hour before everything was supposed to finalize, one of the investors called. He was out. I knew right then it was done. I tried everything. We had tried everything for two months, but this deal was not going to happen. And at some point, you have to look at that honestly and stop trying to resuscitate something that isn't going to come back. It bothered me for a long time. It shook my confidence in a way I didn't expect. Because when something falls apart at that scale, that close to the finish line, the natural question is, what did I do wrong? Why wasn't I enough to pull this off? Then about a year later, I found out some information about one of the potential investors. Without going into the details, I knew that if I had gotten involved with that individual 12 months ago, that everything would have been different. I had been carrying this weight around for 12 months and it suddenly dropped off my shoulders. If the deal had closed and all the pieces somehow had come together the way I'd fought for them, I would have walked directly in something that would have been devastating. The ship going down for Shackleton was the protection. I didn't know that when I was standing on the ice. I couldn't have known. But Shackleton didn't know what was waiting on the other side of his failure either. He just had to decide what kind of man he was going to be in the middle of it. That's what I kept coming back to. Most of us don't fail at executing a plan. We fail at letting go of the plan. We keep trying to sail a sunken ship. We keep pouring energy into something that already went down, defending it, grieving it, explaining it when there are people around us waiting to see what we're going to do next. Your kids are watching, your spouse are watching, the people at work are watching. Not to judge you, but they're watching to see if they can still follow you. That's what Shackleton understood better than almost anyone I've ever studied. So who was this man and why does this story deserve more of a motivational poster? Shackleton was already famous before his expedition. He'd already gotten closer to the South Pole than any human being in history, turned back 97 miles short in 1909 because he calculated that they'd all starve on their return trip if they pushed forever. He came back home with the prize and told his wife, I thought that you'd rather a live donkey than a dead lion. That's who this man was. Someone who cared for his people more than he cared about victory. By 1914, someone else had reached the pole, Roldo Almaston, the Norwegian. So Shackleton did what driven people do when the obvious school is gone. He raised the stakes. The pole is taken, but no one has crossed the entire continent on foot. That's still here. That's still his. He named his ship the endurance. He recruited 27 of the best men. He raised money, he organized supplies, and he set sail in August 1914, the same month that World War I began. The whole world is catching fire and Shackleton is heading south. He got a warning at a whaling station at South Georgia. Experienced whalers who knew those waters better than anyone told him the Weddell Seal was worse that year than he'd ever seen before. The ice was historically bad. They said, wait. He didn't wait. Six weeks later, Vendurance was frozen solid. One crew member wrote that it was like an almond in the middle of a chocolate bar. And here's where most people start to panic. The plan is broken, the calendar's gone, the pressure is building. Shackleton decided to throw a party. They played football on ice, they had birthday celebrations, they sang, they put on performances. One of the expedition's photographers, Frank Hurley, took some of the most extraordinary images ever captured in polar exploration. Because Shackleton understood something about morale that most leaders never figure out. He knew that the mood of a leader becomes the weather of a team. And if he walked out of his cabin looking defeated, 27 men would feel the permission to be defeated. So he didn't. Not in front of them. He did something else too, something that doesn't get talked about enough. He noticed who the pessimists were in his group, the men whose attitude could spread through the camp like a cold. And instead of isolating them, he put them directly in his tent. He kept his enemies close, not to punish them, but to personally manage the contagion. He absorbed all their negative comments before it could spread to everyone else. Ten months drifted, 10 months on a ship that was slowly being crushed by ice. And Shackleton kept the thing together. Then, November 21st, 1915, the ship goes down. And now we're back to that sentence. Ship and stores have gone. So now we'll go home. What happened after that sentence is what I actually want to talk about. Because this is where the real mission started. They were on the ice, three lifeboats, limited food, no shelter, hundreds of miles from any other human beings in the most dangerous stretch of ocean on Earth. And Shackleton made a call. They'd camp on the ice and let them, the drift, carry them north toward open water. They called it Patience Camp. Can you imagine? Patience camp on a floating ice sheet in Antarctica in winter and they waited four months. The ice drifted, sometimes the wrong direction, but in March 1916, the flow they were camped on split in two in the night, separating the men from the lifeboats. They scrambled in the dark and got back. Then finally, in April 1916, the ice broke up enough to launch the boats. 16 days of open sea sailing in free small wooden lifeboats through the southern ocean, one of the most violent bodies of water on the planet. They made it to Elephant Island, a remote, inhibited outcrop of rock, the first land that they've stood on in 497 days. But Elephant Island was not safe. No ships passed there. No one knew that they were still there. They were still gonna die unless someone went and got help. So Shackleton took five men. He took the best lifeboat, the James Card, 22 feet long, and pointed at South Georgia Island, 800 miles away, across the Drake Passage, 17 days, storms, ice, navigating by stars through clouds, sleeping in wet gear, frostbite, dehydration, and they finally made it. But they landed on the wrong side of the island. The whaling station was on the north coast, where they landed on the south coast, and it was separated by a mountain range no one had ever crossed. No map, no gear built for it. Shackleton left the three weakest men on the coast and took two others, and they climbed. 36 hours straight with no rest, crossing glaciers and mountains in the dark, guided by moonlight, knowing that if they stopped moving, they would freeze. When they stumbled into the whaling station at the Stomess, the workers who saw them didn't even recognize them as men at first. They were weathered beyond recognition. The station manager, a man named Sorley, who had met Shackleton before, turned to his colleague and asked, Do you know who that man is? It was Shackleton, 19 months after he'd left. And the first thing he had asked about was the 22 men on Elephant Island. He tried four times to get back to him. Pack ice turned him back three times. But on the fourth attempt, August 30th, 1916, he got through. All 22 men were alive. Thin, cold, some of them barely holding on, but alive. Twenty men went into ice. Twenty-seven men came home. The mission failed. Every single man survived. Here's the thing I keep coming back to. Shackleton never crossed Antarctica. That's the history. That's the record. The expedition he announced that he raised money for and sailed toward never happened. And yet, when you look at the list of the greatest leaders who ever lived, Shackleton is consistently on them. Harvard Business School wrote a case study on him. Management textbooks quote him. Exploration historians rank him above people who actually achieved what they set out to do. Why? Because we have the definition of success wrong. We think success means completing the objective, reaching the poll, closing the deal, hitting the number, getting to where you said you were going. But what Shackleton showed is that real measure of a leader and honesty of a person isn't whether you finished the mission. It's whether you brought your people home. And sometimes, sometimes the mission falling apart is the thing that keeps you safe. I didn't understand why that apartment deal collapsed until a year after the fact. Shackleton didn't understand the full story of his expedition until he was sitting back in civilization with all 27 men alive around him. You rarely get to see the full picture while you're still standing on the ice. That's the part nobody talks about. We're so focused on what we lost that we never stop to ask what might have we been protected from. So who are your people? Who's on your ice? For me, it's Emily, it's my kids, it's the people I work with, it's my friends, it's whoever's listening to this podcast right now. The ship is going to go down. At some point, something that you've built or planned or believed in is going to sink in front of your eyes. That's not pessimism. That's just what it means to take risk and actually live your life. The question isn't whether you can stop it from happening. The question is what you say when it does. Can you look at your people or even just yourself in the mirror and say, that's gone? So now we go home. Not self-pity or blame, just a turn toward what's still possible. Shackleton said once, Optimism is true moral courage. And I think about that often because optimism is easy when things are working out. It costs nothing. But optimism when a ship is sinking in front of your eyes is something different. It's a decision that you have to make every morning. Shackleton's men called him the boss. Not sarcastically, but with genuine reverence. For the rest of their lives, many of them said they would sail back into that same situation if he asked them to. Not because the mission succeeded, but because he never left them. Results build respect. Loyalty comes from people knowing you won't leave them on the ice. So whatever your ship is right now, whatever you're grieving or whatever you're rebuilding from, are you still leading the people who are watching you? If this episode resonated with you, can you do me one quick favor? Can you write a review wherever you listen to podcasts? Your voice matters. It helps us to reach others who need to hear stories like Shackleton and build a life of meaning, even when they feel like their ship is completely crashing around them. Thank you.