Soros Fund Co-Founder Jim Rogers on China and Global Investment

Jim Rogers has been fascinated by China since he drove his motorcycle across the country in the 1980s. The investing legend joins Real Vision to give his view of the rising Asian superpower and, more broadly, on rising Asia in general. Rogers provides his views on the Hong Kong crisis and the simmering trade war. He also weighs in on whether the era of US dollar primacy has passed — especially now that the United States has become, in Rogers’ view, “the largest debtor nation in the history of the world.” Filmed on September 10, 2019 in Singapore.

26:49
You know the rest of the story, you know what happened there, but Mr. Trump is smarter than
26:53
history so we don’t have to worry.
26:55
Mr. Trump knows he can handle history and none of us should worry, because he’s smarter
27:00
than history.
27:02
Even though people say trade wars are bad, and often lead to shooting wars, don’t worry,
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I’m smarter than history.
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MATT MILSOM: He does seem to be able to just move to the next person once he’s had– go
27:15
at somebody then it slackened off, just goes to next target is going to be Europe, once
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he’s done with China, even though nothing’s actually resolved.
27:23
JIM ROGERS: The problem, Matt, is that when things get bad, so far the American economy
has held up well because of a lot of money printing, out of government spending, cut
taxes, everything possible to hold up the American economy has held it up.
When things get bad in America as they will, Mr. Trump is not going to say, “It’s my fault.
I got it wrong.”
Donald Trump is going to say those evil Germans, those Koreans, those Canadians, and he’s going
to come back hard with more and more whatever you want to call it.
The situation, we’re going to have the worst bear market in my lifetime.
I can tell I’m older than you, so it’s going to be the worst in your lifetime, too.
What I suggest you do is watch Real Vision, and you’ll get educated, and you will see
how bad things are.
Then you’ll get there.
Most people will turn on the internet or turn on the TV, say, “Wow, look at this.
Things are great.”
Mr. Trump tells you every day, if you watch American TV, he will explain you things are
really, really very good.
You don’t worry.
Maybe you need somebody crying wolf, maybe you need somebody saying, “Wait a minute,
guys, wait a minute.
Look at this.”
Maybe Real Vision is the last vision for all of us.
MATT MILSOM: You think he gets back in?
JIM ROGERS: Get back into what?
MATT MILSOM: Trump 2020?
JIM ROGERS: I got to respect you, what I think it’s– I know it’s very hard to dislodge a
sitting president in America for many, many reasons.

I would suspect that’s the same to this time.
Now, we got rid of Coolidge, and Hoover.
29:08
We got rid of Hoover because the market collapsed but we don’t have much time for that because
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the election is only, what, 13-14 months away now.
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If the market really collapses in the next 13 or 14 months, then I would change my view,
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but there are enough things he can do, which is why it’s hard to get rid of sitting presidents.
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They’ll prop things up long enough to get through the election.
29:34
I would, if I were betting and I’m not a betting man, but if I were, I would bet that Trump
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will be reelected.
29:40
MATT MILSOM: A lot of speculation that he might actually start to swerve the Fed and
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play the currency markets himself for the Treasury.
29:48
JIM ROGERS: What, Trump will start buying what?
29:51
US dollars or renminbi?
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What’s he going to buy?
29:53
MATT MILSOM: He’s going to be selling dollars.
29:54
JIM ROGERS: He could do that.
29:56
Yes, and he might.
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He cannot force the Fed to do it.
30:00
No, but he could, he could browbeat him.
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He can certainly force the Treasury to do that, to sell US dollars.
30:10
First of all, I’m not sure the market would put up with it, it would for a while, obviously,
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it would for a while, but eventually, the market, as I said to you before, I mentioned
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the market’s going to say to these guys, “We’re not going to play this game anymore.
30:23
This is an absurd, ludicrous game.
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It’s never happened before.
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We know it’s not going to work.
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We’re not going to play anymore.”
30:30
Okay, maybe we’ll try.
30:32
I don’t think it’s enough.
30:34
Maybe it’s enough to save the election, I said to you before.
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It’s so difficult to dislodge a sitting president.
30:38
There are lots of things he can do.
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If he needs votes in that state, he spends a lot of money in that state.
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His opponent cannot do that, the opponent can say look, what a terrible person he is.
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He’s spending money in your state.
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The people say, thank you, thank you spend more money in my state.
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We’ll vote for you.
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MATT MILSOM: He can almost play the Fed to his own fiddle, I guess at the same time.
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He can blame them if it goes– JIM ROGERS: He certainly can blame them, whether he can
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persuade them.
31:04
He seems to be persuading them now is another question, but sure.
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That’s what I mean, if he goes in there and threatens them, or does x or does y, sure
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he can.
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That’s the problem when you’re the president, or the advantage when you’re the president.
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MATT MILSOM: I see Powell’s having a bit more backup by myself.
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I just think he’s his own guy.
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Really, he’s not a PhD Economics.
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He’s a– JIM ROGERS: That’s the best news.
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I believe PhDs, which is bad news.
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We’ll see.
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MATT MILSOM: I could see that arising a bigger conflict there, you think between Powell and–
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JIM ROGERS: No, I can see a huge conflict and that’s going to– the Federal Reserve,
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its debt went up by five, six times in 10 years.
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If I had said to you 20 years ago, a major central bank in the world is going to increase
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the debt on its balance sheet by 500% in 10 years, you’re going to say, “Get out of here.
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We’re not going to talk to you anymore.
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You’re not even smart enough to talk on TV.
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What are you talking about?”
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It’s inconceivable that it could have happened, but it’s happened.
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Sure, they have a problem, too.
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How far can they go?
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How far can any of us go?
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MATT MILSOM: It surprised me the volatility’s so cheapened right now.
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JIM ROGERS: The debt worldwide is the highest in world history.
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Interest rates are the lowest in world history.
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In 2008, we had a big debt problem.
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China, which had a lot of money saves for a rainy day, started spending the money and
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helped save the world, but even China now has debt.
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China can’t save the world anymore.
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The central bank came riding in with its printing presses, helped save the world.
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That’s getting late for all the printing presses in the world.
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It’s getting late in the day.
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MATT MILSOM: Is the rate of change as well as a debt in China that’s extraordinary just–
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JIM ROGERS: Oh, no, I know.
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To repeat, ports in China has said we’ll let them go bankrupt.
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I don’t think they will.
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Not that they’re lying, I think they believe that they’re going to let people go bankrupt
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but they haven’t had this problem in decades.
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They’re bureaucrats and they’re academics, haven’t felt the pressure of people calling
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up saying, “You must save Chinese civilization.
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This is Chinese history, our image our integrity.”
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No, they haven’t had that gigantic pressure from everybody in the country, they’re saying,
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“Save Chinese civilization.”
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What they really mean it save me.
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They haven’t had that yet.
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MATT MILSOM: Xi as a link leader seems to be much more of a Maoist than ever before,
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to me.
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JIM ROGERS: I’m not sure Maoist, but they’re certainly closing off in that sense.
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Yes.
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Deng Xiaoping started opening up and Deng Xiaoping said you open the windows, you’re
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going to get some flies, but you’re going to get fresh air and sunshine, and the fresh
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air and the sunshine are worth the flies.
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He seems to be saying we don’t want flies and the last 40 years, much of the progress
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has been 18-year-olds in a garage doing crazy things on the computer.
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Alibaba, Microsoft, the names go on, and on and on.
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These were just kids doing wild, crazy things on the internet, which was open and free to
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nearly everybody.
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You start closing these things off, and it’s going to slow progress, it’s going to slow
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things now, whether we like it, history is always showing that.
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You close off and you go into decline.
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It does seem to be happening not just in China, even in the US, but it does seem to be happening
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more and more, so maybe we’re in for the dark ages again.
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MATT MILSOM: I don’t know.
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It’s almost that you think about where you’re going to head or what currency you need to
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get into, where you’re going to be safe.
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Do you know what I mean?
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You start thinking about– JIM ROGERS: That’s not what I mean.
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I don’t have a job.
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I can’t figure out a way to save myself.
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MATT MILSOM: You made the move to Asia on the back of those thoughts, I guess that that’s
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going to be a Pacific centuries.
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JIM ROGERS: Well, I moved here you because I know that the 20th century is Asia, 21st
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century is Asia.
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I wanted my children to know Asia and to speak Mandarin.
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That’s the best preparation I can give them for the 21st century.
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That’s why I’m here.
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Of course, Asia is continuing to develop and boom and head of the rest of the world.
35:28
There is some debt in Asia, but nothing like in the West.
35:32
Most of the Western countries are really broke, especially when you pull into pension plans.
35:38
Europe’s got gigantic pension, US too, gigantic pension obligations, which they’ll never able
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to [indiscernible].
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MATT MILSOM: Yeah.
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Demographically, where does that end up?
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JIM ROGERS: It’s already starting to ruin a lot of people.
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Asia has probably– will have problems but nothing like some that are rising in the West.
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I can’t bear for my kids.
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MATT MILSOM: The world of agricultural investment view is still a– JIM ROGERS: Yeah, agriculture
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has been a disaster for 35 years or so.
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The average age of farmers in America is 58.
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More people in America study public relations and study agriculture.
36:12
The highest rate of suicide in the UK is agriculture.
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Of Japan, the average age of farmers is 68.
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Nobody becomes a farmer, you go to Japan now, there’re huge stretches of land, they’re just
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empty.
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They can’t find anybody to farm them.
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Farmers have died, the kids have gone to Osaka.
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There’s nobody to farm that land.
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If you want to be a former, go to Japan.
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You can get a lot of land cheap.
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That’s true.
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Australia, Canada, all of these countries have very, very aged old farmers, men and
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women.
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It’s millions of Indian farmers have committed suicide, as I’m sure you know.
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No, no, agriculture is a disaster.
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The Chinese have a word, you know the Chinese word weiji?
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It means disaster and opportunity are the same and they are.
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If you can survive the disaster, you’re going to make a lot of money with the opportunity.
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MATT MILSOM: I guess the commodity complex per se, are softer on their knees-ish for
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the last five years.
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They’re actually doing okay in the States.
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JIM ROGERS: Yeah, yeah.
37:17
Things like sugar, sugar is down over 80% in the last 40 years, what do you notice down
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80% in the last 40 years?
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My IQ.
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Other than that, there’s not much that has declined, that deteriorated like some of the
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agricultural products.
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MATT MILSOM: Difficult bet to make given the climate change, too?
37:38
JIM ROGERS: Well, yeah, climate change is taking place, is taking place for thousands
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of years.
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Go back and look at trees, and soil layers and iceberg layer, we see that climate change
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has always been taking place one way or the other, and it seems to be happening again.
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Of course, that’s going to be great for some farmers, disastrous for other farmers.
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The key is to be the farmer that it’s great for, not to be a farmer that gets wiped out
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because of climate change.
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The Sahara Desert, which is the size of the continent with 48 states, used to be a huge
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agricultural area.
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Pigs, cows, wheat, corn, everything, huge, huge.
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We had climate change.
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We had ecological change, you know the rest of that story.
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If you were a farmer in Algeria 2000 years ago, you probably didn’t do very well.
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You should have moved to Iowa 2000 years ago.
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MATT MILSOM: Would it be too much to ask your asset allocation now?
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JIM ROGERS: You can ask, I don’t know.
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I don’t sit around.
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I don’t have a committee met.
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I don’t have anybody to answer to.
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I know I can still pay my bills.
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I do own some gold and silver.
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I do own a lot of US dollars, I’ve told you about.
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I’m short some junk bonds, short the ETF, Russia, China.
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I don’t own a lot of shares anywhere right now.
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The Japanese market, I sold out of.
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I used to own a lot of Japanese shares, sold out completely.
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MATT MILSOM: Why was that?
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JIM ROGERS: I bought them so well.
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It’s not often I get it right so I’m going to brag for a minute.
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The Japanese market was very, very cheap and I started by and then the tsunami.
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Remember the tsunami?
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Everything collapsed, I bought a little, gone up a lot, it tripled since then.
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I could see wasabi and the toll got stronger and stronger and stronger.
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They’d already printed lots of money.
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The central bank said we’ll print as much as we have to.
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That’s what they said.
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They said it out loud.
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Not some crazy guy saying it.
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I said what else can happen?
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What else can go right?
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They’ve spent a lot of money on infrastructure.
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They bought a lot of securities, so I sold out.
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So far, I’m right, but don’t worry, I make plenty of mistakes.
40:07
MATT MILSOM: I guess, it changed your beast, don’t even trade anymore, eh, because there’s
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no float?
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JIM ROGERS: Nothing to trade, why would you buy them?
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Who’s going to buy them, except a central bank?
40:16
MATT MILSOM: They have to keep going?
40:18
JIM ROGERS: I told you I have.
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I’m going to Japan tomorrow, there’s been a best seller saying, “A Warning to Japan.”
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If they keep going– MATT MILSOM: That’s a book?
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JIM ROGERS: Yeah.
40:29
MATT MILSOM: Sorry, I didn’t know that.
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JIM ROGERS: No, it’s the number one bestseller.
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MATT MILSOM: Congratulations.
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JIM ROGERS: I’m shocked.
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I’ve made two number one bestsellers.
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MATT MILSOM: What was the other one?
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JIM ROGERS: I forget that, it was some Japanese.
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It was something like, “A Warning to Japan.”
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MATT MILSOM: But this is a specific for that market, or they were– JIM ROGERS: Two books
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in Japanese.
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They were translated, my English was translated into Japanese.
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Two books in 2019 have been number one bestsellers by me.
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This is a shock.
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How could this happen?
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I’m more surprised than anybody.
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They called me up, that smarty say you got to come to Tokyo.
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I said why?
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He said your books have won bestseller.
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I forgot about the book.
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The book resulted from some reporters coming here and interviewing me like you.
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We’re out for several hours.
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I said we’re going to publish this.
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Okay, go ahead.
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I don’t care.
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Forgot about it.
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MATT MILSOM: You got a book tour now?
41:17
JIM ROGERS: Yeah, I’m leaving tomorrow.
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I’m going tomorrow for a book tour in various cities of Japan, promoting, “A Warning to
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Japan.”
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MATT MILSOM: What was the essence of that?
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Was that demographics or that– JIM ROGERS: If you’re 10 years old, you better get out.
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If you’re 10 years old, you better get an AK47 and learn how to use it.
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These are not– it’s simple.
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I say to them, they will say, of course, he’s a foreigner.
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Don’t worry.
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The Japanese don’t like foreigners, and so they will just say, he’s a– whenever they
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say they don’t like somebody, they say he’s a foreigner so you don’t have to listen to
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him.
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I say to them, yeah, okay, I’m a foreigner, but this is arithmetic.
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It’s addition, the debt goes up every day.
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That’s simple addition and it’s subtraction, the population goes down every day.
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Central bank has been printing huge amounts of money.
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This is just simple addition and subtract.
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Forget that I’m foreigner and for some reason, both of them became number one bestsellers.
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I guess it’s because nobody in Japan ever says things like this.
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I don’t know why I became, but listen, I’m shocked.
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MATT MILSOM: Do you have any views on Softbank?
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JIM ROGERS: So far, they’ve made a lot of money but I don’t know enough to say much
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more than that.
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I read that problems are developing, but I have no knowledge, enough knowledge to say
42:39
anything other than that.
42:40
MATT MILSOM: I guess WeWork is the speculation for those issues there, for the float.
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JIM ROGERS: WeWork is not their only asset at Softbank.
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What I read about WeWork, WeWork may be one of those things.
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You remember in 1999?
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I think it was called pets.com or something.
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It was one of those things that was when people talk about the end of the bull market or the
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signal, or the sign that it was over, that may be WeWork now.
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They were printed out in 1999.
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That’s the one that people often bring up, I was not sure.
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I wish I had but they bring that one up.
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Now, if you look at the current bull market, maybe someday in 10 years, we’re all going
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to look back and say, “They rang that bell.
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That bell was called WeWork.
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That was the sign that we were coming to the end.”
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It’s always something that people look back on that it may be WeWork.
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MATT MILSOM: The amount of questioning that browned the IPO pricing makes you think that
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the greater fool game may have just come to a grinding halt.
43:54
JIM ROGERS: I’ve never read the Prospectus but I’ve read a lot in the papers about the
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story, the company, that IPO, the CEO, etc.
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Just I’m sure you have too.
44:05
I read it and I say this is 1929, this is 1999.
44:12
This has all happened before.
44:14
MATT MILSOM: They have nines in them.
44:18
JIM ROGERS: Yeah.
44:20
See, 1899– well, anyway, you read, I read this stuff and I’d say oh, yeah, this has
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happened before.
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I remember reading about things like this in previous bull markets, previous bubbles.
44:33
MATT MILSOM: What brings you to an investment then?
44:36
Is there a sector or there is an idea or somebody pitches to you?
44:38
JIM ROGERS: No, it’s usually– the nature of who I am, I’m always looking or I’m always
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listening.
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If I stumble on something, I’m not out looking like I used to, but if I stumbled on something,
44:53
I often do homework and then I’m in this Russian stock that I’m buying, I stumbled on it.
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The more homework I do, the more I buy.
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I continue but it’s usually I will stumble on something.
45:04
MATT MILSOM: Public, is it a public stock?
45:06
JIM ROGERS: Yeah, it’s a public company.
45:08
MATT MILSOM: Sector?
45:10
Which sector would have been?
45:11
JIM ROGERS: You’re a very good reporter, but I’m not going to tell you because if I told
45:15
you, you would know exactly what I’m buying.
45:17
MATT MILSOM: Okay.
45:18
I’m sure it wouldn’t be that easy to spot.
45:20
JIM ROGERS: There are plenty of disasters in Russia.
45:23
Everybody hates Russia now, so Russia’s on my list.
45:28
Anyway, I will probably buy Russian government bonds and rubles again soon.
45:34
I own Russian government bonds in rubles.
45:37
The yield is very, very high.
45:38
The ruble is hated.
45:39
The Russians are hated, et cetera.
45:41
MATT MILSOM: Any other markets that are particularly hated that you fancy?
45:44
JIM ROGERS: Well, I told you Venezuela but you and I cannot do it.
45:48
I cannot do anything in Venezuela.
45:51
Zimbabwe, I bought a few shares of Zimbabwe, some of the North Korea but that’s illegal,
45:57
too.
45:58
I’m looking, but part of the problem is there are few markets that are hated so much.
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I mean I am buying Russia, it’s still hated.
46:10
Most markets, even Germany.
46:12
Look at Germany hit peak, what, two years ago.
46:15
Been going out since but it’s not cheap.
46:18
It’s not hated.
46:19
Germany still a very large and [indiscernible] economy.
46:23
No, I don’t see many now that jumps off the page to me and says, oh my God, you got to
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buy this disaster.
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I would love to find something like that, but I’m too lazy.
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MATT MILSOM: I’m thinking there’s probably a good places to stop.
46:38
JIM ROGERS: I’m too lazy.
46:41
Very good places to stop buying, I commend laziness to all of you.
46:45
Watch Real Vision and get lazier and lazier, and lazier.
46:48
MATT MILSOM: Jim, thanks for having us and thanks very much for coming on.
46:50
JIM ROGERS: My delight, my pleasure.

‘This Is Not the Way Everybody Behaves.’ How Adam Neumann’s Over-the-Top Style Built WeWork.

The skills that helped fuel We Co.’s breakneck growth are piling up as potential liabilities as the company prepares to go public

Adam Neumann was flying high. Literally.

His office-rental giant WeWork was months away from being valued at $47 billion. Revenue was doubling annually. And Mr. Neumann was zipping across the Atlantic Ocean in a Gulfstream G650 private jet with friends last summer, smoking marijuana.

After the group landed in Israel and left the plane, the flight crew found a sizable chunk of the drug stuffed in a cereal box for the return flight, according to people familiar with the incident. The jet’s owner, upset and fearing repercussions of trans-border marijuana transport, recalled the plane, leaving Mr. Neumann to find his own way back to New York, these people said.

Since Mr. Neumann co-founded WeWork—recently renamed We Co.—with Miguel McKelvey nine years ago, he has led with unusual exuberance and excess. His combination of entrepreneurial vision, personal charisma and brash risk-taking helped the company surpass $2 billion in annual revenue, and made it the country’s most valuable startup.

Now many of the same qualities that helped fuel his company’s breakneck growth in the private market are piling up as potential liabilities as the company prepares to go public—helmed by a CEO who looks little like a typical public-company chief.

Mr. Neumann muses about the implausible:

  • becoming leader of the world,
  • living forever,
  • amassing more than $1 trillion in wealth.

Partying has long been a feature of his work life, heavy on the tequila.

Public investors are increasingly skeptical of the formula that has worked for Mr. Neumann so far: his pitch that We is far more than a real-estate company. With its rapid growth and use of technology, he argued, the company deserves rich valuations normally reserved for tech companies.

Instead, many potential investors now see a fast-growing office subleasing company with losses of more than $1.6 billion last year.

Since We filed the prospectus for its initial public offering last month, it has been besieged with criticism over its governance, business model and ability to turn a profit. It is now expecting an IPO valuation as low as a third of the $47 billion sticker price it garnered in a January funding round—a drop without recent precedent. This week, We postponed the offering until October at the earliest.

Wall Street and Silicon Valley investors have been dismayed by the number of potential conflicts of interest disclosed in the “S-1” IPO prospectus, including Mr. Neumann leasing properties he owns back to the company and borrowing heavily against his stock. Even some of We’s private investors said they were angered to learn that an entity Mr. Neumann controls sold the rights to the word “We” to the company for almost $6 million—before public pressure led him to unwind the deal.

“This is not the way everybody behaves,” said Dick Costolo, former CEO of Twitter Inc., who led the company through one of the larger tech IPOs of the past decade. “The degree of self-dealing in the S-1 is so egregious, and it comes at a time when you’ve got regulators and politicians and folks across the country looking out at Silicon Valley and wondering if there’s the appropriate level of self-awareness.”

Given the prominence of the IPO, he added, “that is a big problem.”

Mr. Neumann, 40, declined to comment through a spokesman, who cited rules surrounding the planned IPO. Mr. Neumann told We employees Tuesday the process had been humbling and he would learn from it, say people who heard him. We executives have previously said he is strongly devoted to the company, and many of his personal transactions were made with the company’s best interests at heart.

This account is based on interviews with current and former employees, investors and friends who interacted with Mr. Neumann as he built We.

For startup investors, the 6-foot-5 Mr. Neumann has always had the qualities they crave in Silicon Valley founders, despite being based in New York. He is intensely ambitious and a masterful storyteller with a magnetic personality who can inspire and sell.

Raised in Israel on a kibbutz, Mr. Neumann moved to the U.S. when he was 22, where he attended Baruch College and tried to start businesses. One was a collapsible heel on women’s shoes that didn’t get off the ground. Working out of his Tribeca apartment, he started Krawlers, which sought to make baby clothes with knee pads to make crawling more comfortable. The slogan, he has said: “Just because they don’t tell you, doesn’t mean they don’t hurt.” It never gained traction.

He and Mr. McKelvey started a small co-working space on the side during the recession that followed the financial crisis and were amazed by the demand.

By 2010, they had started WeWork, with essentially the same core business model that exists today: They lease an office long-term, renovate it to make it hip and inviting, and sublease smaller desks and offices short-term.

Early on, Mr. Neumann painted a picture of how WeWork was connecting entrepreneurs and others who in the past would have worked from home or in coffee shops; how the company would bring a new way of working to a changing world.

The founders planned for the “We” brand to expand beyond office space into other categories such as housing and finance. Mr. Neumann ramped up its image as a tech company as it grew.

It introduced a mobile app for network members, meant to facilitate a “physical social network.” The company emphasized its data and how it was using artificial intelligence to glean insights about buildings.

Past funders and employees tell stories of how an animated Mr. Neumann convinced them within minutes to believe in the company’s epic future.

“When I met him, after a couple of minutes, I wanted to invest,” said Joey Low, whose Star Farm Ventures put money into the company in 2013 and multiple subsequent funding rounds. “He was hungry for success—that was for sure.”

Even former executives who disliked Mr. Neumann give him credit for an extraordinary ability to motivate employees and push the company.

He forgoes many conventions of the standard, buttoned-up CEO. He pushed for rowdy parties in the early days. He often walks barefoot around the office. In an earlier office, he blared songs by pop-star Rihanna while a trainer held a punching bag for him, and then walked around afterward while still sweaty from the exertion.

Like some high-profile CEOs in tech, he hopes to live forever, according to three people who heard him say this, and has invested in life-extension startup Life Biosciences LLC.

It says its mission is “to create a future where age-related decline is not a fact of life.”

As WeWork grew, Mr. Neumann took on ever more investment, bringing in tens of millions of dollars from venture capitalists, then hundreds of millions from mutual funds T. Rowe Price and Fidelity Investments. Crucially, he secured full control of the company in 2014 when investor demand was high—getting shares with 10 times the votes of others.

Ultimately he found a kindred spirit in Masayoshi Son, CEO of SoftBank Group Corp., who, like Mr. Neumann, is a risk-taker who respects giant bets. Mr. Son, a telecom veteran who raised the world’s largest tech fund in 2017, met Mr. Neumann in India in 2016 and pondered an investment.

SoftBank first committed $3.1 billion in new funding in 2017. Mr. Neumann has told others that Mr. Son appreciated how he was crazy—but thought that he needed to be crazier. A SoftBank spokeswoman declined to comment.

Many former employees said they didn’t always know how seriously to take some of Mr. Neumann’s pronouncements. Early on, he would throw out seemingly random ideas, like adding a pool in the basement of the company’s headquarters or starting an airline.

He told at least one person directly that his ambitions included becoming Israel’s prime minister. More recently, he said that if he ran for anything, it would be president of the world, according to another person who spoke with him.

“The influence and impact that we are going to have on this Earth is going to be so big,” he said last year at a “summer camp” southeast of London, where the company’s staff were all flown for a music festival-like event. One day, he proposed, the company could “solve the problem of children without parents,” and from there go onto other causes such as eradicating world hunger.

Alcohol flowed in great quantities; bartenders handed out free rosé by the bottle. Employees from around the globe posed for photos with the CEO. Some seminars had a spiritual component, including one with holistic health expert Deepak Chopra, who advocates regular meditation and yoga.

Mr. Neumann has told several people over the past two years that a personal goal is to become the world’s first trillionaire.

He relishes trips in private jets. Last year, We bought one for more than $60 million, people familiar with the sale said. Mr. Neumann has borrowed more than $740 million against his stock and has sold multiple hundred million dollars of shares, people familiar with those sales say, eliciting widespread criticism from analysts and Silicon Valley investors. These share sales weren’t disclosed in the IPO prospectus.

In a 2015 investment round, Mr. Neumann sold tens of millions of dollars of shares. Soon after, the company launched a buyback program offering to purchase employees’ shares too. But the company gave employees a different arrangement, giving them a payout per share worth substantially less than what Mr. Neumann was paid, people familiar with the sale said. Mr. Neumann’s sale wasn’t publicized within the company.

We executives have said the buyback price couldn’t be higher for tax reasons. More recent stock sales have been more equitable.

A recent change to the company’s corporate structure puts Mr. Neumann and a group of executives in a position to have a lower tax rate on some of their stock compensation than the rest of the employees in the company. We said the new structure was created in part to make it easier to expand into new businesses beyond co-working, according to IPO filings.

In private, Mr. Neumann often talks about the company’s valuation, according to people involved with the conversations. He has insisted that We’s valuation will eventually be many times what it was earlier this year, when it reached $47 billion, the people said.

For Mr. Neumann and the investors, the premise has always been that the market would look at We as more than real estate. The high valuation—twice that of United Airlines Holdings Inc. —has enabled the company to continue to raise money to fund new desks and offices and keep growing, even as losses persisted.

He has created a distinct culture in his mold. T-shirts and signs sport slogans such as “hustle harder” and “Thank God it’s Monday.” Employees are often big company boosters, creating a work-hard, play-hard office, with a millennial hipster vibe.

Alcohol has been a big part of the culture, particularly in We’s first half-decade. Mr. Neumann has told people he likes how it brings people together, and tequila, his favorite, flows freely. Executive retreats sport numerous cases of Don Julio 1942, with a retail price of more than $110 a bottle, and pours sometimes start in the morning.

A few weeks after Mr. Neumann fired 7% of the staff in 2016, he somberly addressed the issue at an evening all-hands meeting at headquarters, telling attendees the move was tough but necessary to cut costs, and the company would be better because of it.

Then employees carrying trays of plastic shot glasses filled with tequila came into the room, followed by toasts and drinks.

Soon after, Darryl McDaniels of hip-hop group Run-DMC entered the room, embraced Mr. Neumann and played a set for the staff. Workers danced to the 1980s hit “It’s Tricky” as the tequila trays made more rounds; some others, still focused on the firings, say they were stunned and confused.

Mr. Neumann also enjoys marijuana, his friends and former executives say. As with the Israel trip, multiple people who have been on planes with him say he often smokes while airborne.

Much of this culture has been pared back as the company has matured. The summer camp was canceled this year.

Mr. Neumann has mellowed some too, friends say. He sometimes stays away from alcohol for weeks or months at a time, and raucous parties are less frequent. His wife, Rebekah Neumann, has helped pare back the partying, former executives say.

Ms. Neumann, a first cousin of actress and wellness guru Gwyneth Paltrow, has said she and Mr. Neumann clicked when they first met, when Mr. Neumann was broke and struggling to make a business.

“It felt like time stopped,” she told a podcast interviewer last year. “I just knew he was the man that was, hopefully, going to help save the world.

Mr. Neumann and his wife, Rebekah Neumann, in 2018. PHOTO: EVAN AGOSTINI/INVISION/ASSOCIATED PRESS

Former employees who worked with her say she pushes to infuse spiritualism in We—which has a mission statement to “elevate the world’s consciousness”—and enjoys broad autonomy at the company. She is the chief brand officer and head of WeGrow—the private company’s preschool and elementary school that costs up to $42,000 a year and is open to anyone. She is an important counsel for Mr. Neumann, and he has told staff they often make decisions together.

The two split time between some of their many homes—they have at least five—including a 60-acre Tudor-style estate north of New York City. They have told staff they started WeGrow after they were dissatisfied with schooling options for their five children.

The two have committed giving $1 billion to charity over the next decade.

Ms. Neumann had been slated to play a large role in choosing Mr. Neumann’s successor if he were ever incapacitated, but was recently removed from that position amid pushback from investors.

Both Neumanns could be impulsive at times, former executives say. Ms. Neumann has ordered multiple employees fired after meeting them for just minutes, telling staff she didn’t like their energy. She and Mr. Neumann have sent maintenance and IT staff to their homes to fix various items.

When Mr. Neumann announced in July 2018 via video call from Israel that the company was banning meat, executives in New York were caught off guard. With little explanation from Mr. Neumann, a group huddled to determine a rationale—they settled on sustainability—and the mechanics of what would be banned and how.

They determined employees couldn’t expense meals with meat, but they could eat it in company offices, so long as the company didn’t pay. Former employees say they have since seen Mr. Neumann eat meat.

He previously has instructed staff to fire 20% of employees a year, bemoaning the number of “B” players hired amid rapid growth. Managers were unable to hit the target even when they included attrition.

Still, former executives believe his outlandish targets for items such as reducing construction costs have forced better results than more realistic goals—and are a driver of the company’s continued growth.

That growth has remained remarkably consistent, roughly doubling every year for most of We’s history, and remains the main selling point to investors.

“This guy is pushing hard, but he’s all in,” said John Caddedu, managing director at early We investor DAG Ventures. Building something as big as We, he said, “requires extraordinary devotion and focus and will and a lot of the things that throw some people off.”

Mr. Neumann had been expecting the revenue growth rate would also be well received by the public markets. Companies such as Netflix Inc. and Amazon.comInc. were growing at slower rates nearly a decade in, though they were losing far less money.

Instead, after the IPO prospectus was released in mid-August, the company became the butt of jokes in Silicon Valley and among Wall Street crowds. Analysts and competitors critiqued its lack of detail around the economics of its offices. Corporate governance proponents were aghast at the long list of potential conflicts. Some observers noted the irony of personally profiting off the trademark for the word “we.”

Years leading a private company left Mr. Neumann unprepared for the negative reaction, people familiar with the IPO discussions have said. Every time he raised money—often at in-person meetings where check-writers could see Mr. Neumann’s charm—the valuation went up, money rolled in, and the business expanded.

Some investors said when they raised concerns about Mr. Neumann’s self-dealings, he brushed the issues aside. Despite We’s growing size, its losses have been increasing at the same rate as revenue, creating a constant need for fresh investments. That is contrary to earlier projections from Mr. Neumann, who said the company wouldn’t need more money.

Meanwhile, numerous other business lines, including a residential arm, a gym and an office design and management arm, have all been scaled back or failed to deliver the high profit margins once expected, people familiar with the businesses said.

In a videoconference with the whole company Tuesday, Mr. Neumann, dressed uncharacteristically in a gray suit and a white button-down shirt, told the staff it has “played the private market game to perfection,” listeners said.

As for the public markets, he said, the company was still learning the rules of the game.