20VC: Sequoia's Shaun Maguire: Will We See WW3 Shortly | Why DEI is a Cancer for Society | Why Iran is the World's Greatest Evil | Why Trump is the Only Hope for Peace in the Middle East | Trump vs Harris: Who Wins & What Happens

Shaun Maguire is a Partner at Sequoia Capital. At Sequoia he led their investment into SpaceX, The Boring Co and X among many others. Before Sequoia he co-founded a cybersecurity company called Expanse which Palo Alto Networks acquired for $1B. Before Expanse, Shaun worked at DARPA and was deployed to Afghanistan. In Today's Episode with Shaun Maguire We Discuss: 1. Why Iran is the Greatest Evil in the World: What specifically makes Iran the greatest danger to the world today? How should the US respond to the threat posed by Iran? Does the US have to go to war with Iran knowing that they now have nuclear weapons? How did the Biden-Harris administration worsen relations both with Iran and Saudi? Is Trump the best chance we have of bringing peace and stability to the Middle East? 2. Russia, Ukraine, Gaza and Israel: What is the Right Next Step: Does Shaun believe that the US should remove funding from Ukraine? How would Trump change the US' relationship with Putin? What does Shaun believe is the right next step for the US in Gaza and Israel? What does Shaun mean when he says the public have no idea how much crazy s**** happens? 3. Freedom of Speech and DEI: Remnants of the Past: Does Shaun believe we live in a society with freedom of speech? How does it differ between the US and Europe? Is Shaun negative on the future of Europe? Does he agree with Larry Summers that "it is a museum"? How does Shaun evaluate the state of diversity, equity and inclusion (DEI)? Why does Shaun believe that wokeness and cancel culture is one of the greatest dangers to society? When does Shaun believe that transgender becomes a problem in children? Where is the line? 4. The Election: Who Wins and What Happens: Does Shaun agree that Kamala is pulling ahead and Trump is now chasing her? How does Shaun analyse the chances of Trump winning? To what extent is it a real threat that there will be civil unrest if Trump does not win? Why does Shaun argue that too much blame is placed on Trump for Jan 6th and he did nothing that Hilary Clinton had not done in disputing prior elections? How does Shaun evaluate the appointment of JD Vance? Does Shaun agree with the echoes from the crowd for Trump to remove him? 5. Elon Musk, US Selling All BTC & Inside Sequoia: What does Shaun believe are the three qualities that make Elon Musk one of the greatest entrepreneurs of all time? Why does Shaun believe that it is a massive mistake for the US to sell all BTC holdings? Who is the best picker in Sequoia? Who is the best at sourcing? Does Shaun get told off internally for his opinions being shared so freely externally? What have been Shaun's biggest lessons from working alongside Doug Leone? 20VC: Sequoia's Shaun Maguire on Will We See WW3 Shortly | Why DEI is a Cancer for Society | Why Iran is the World's Greatest Evil | Why Trump is the Only Hope for Peace in the Middle East | Trump vs Harris: Who Wins & What Happens

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Speaker 00

  I think there's a huge difference between having freedom of speech, being willing to use it, and having lots of information warfare. I don't think we had freedom of speech before Elon bought Twitter. I think we're moving away from free speech very quickly in Europe. The modern paradigm of DEI is toxic woke ideology that is literally cancer for society. The Iranian philosophy when you're losing is to create chaos. So they're creating as much chaos in the world as they possibly can. The war in Ukraine, America could not have botched the initial response more.

• 0:30Harry Stebbings?

  Is Donald Trump the best chance we have of alleviating the soon to be World War III in the Middle East?

• 0:37Speaker 00

  100%.

• 0:38Harry Stebbings?

  Why? This is 20 VC with me, Harry Stebbings, and today we have a very special guest. Doug Leone described this individual as the most interesting man in the world. He's a partner at Sequoia. He's led deals in SpaceX, X, The Boring Company, and many more. Before venture, he co-founded a cybersecurity company called Expanse, which Palo Alto Networks acquired for $1 billion. And before that, he worked for DARPA and was deployed to Afghanistan. Come on, that has to be the coolest bio for any guest ever on 20 VC. It is, of course, Sean Maguire, partner at Sequoia. This is perhaps the spiciest show we've ever done on 20 VC. But before we dive in, when a promising startup files for an IPO

• 1:21Harry Stebbings?

  or a venture capital firm loses its marquee partner, being the first to know gives you an advantage and time to plan your strategic response. Chances are, the information reported it first. The information is the trusted source for that important first look at actionable news across technology and finance, driving decisions with breaking stories, proprietary data tools, and a spotlight on industry trends. With a subscription, you will join an elite community that includes leaders from the top VC firms, CEOs from Fortune 500 companies, and esteemed banking and investment professionals. In addition to must-read journalism in your inbox every day, you'll engage with fellow leaders in the active discussions or in person at exclusive events. Learn more and access a special offer for 20 VC's listeners at

• 2:06Harry Stebbings?

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• 2:10Harry Stebbings?

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• 2:51Harry Stebbings?

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• 3:36Harry Stebbings?

  So to learn more about the number one most active law firm representing VC-backed companies going public, head over to Cooley.com and also CooleyGo.com, Cooley's award-winning free legal resource for entrepreneurs. You have now arrived at your destination. Shaun, I am so excited for this, dude. Listen, I've wanted to do this one for so many years. I've heard so many great things. Doug Leone goes to me before this. Shaun is the most interesting man I've ever met. Impossible. But thank you so much for joining me, man. Hey, it's great to be here. Thank you, Harry. I'm a big fan. Listen, first question, dude. How did you go from a high school dropout to a PhD at Caltech? That's quite a jump.

• 4:15Speaker 00

  With a big chip on my shoulder. Yeah, I mean, look, as a kid, I wasn't stupid, but I really hated school and hated my teachers. You know, I went to public school. I got a zero on my first Algebra II test for not showing any work. The teacher wouldn't change their mind. Like, I offered to show my work, et cetera. Once I got a zero on that exam, like, the highest grade I could get in the class was a C. At that point, I was just like, I'm done with school. I'm just gonna go learn stuff on my own, be on my computer. And I did that. And then I kind of hacked my way out by doing this thing called the California High School Proficiency Exam. It's basically a test you can take that lets you leave high school early. And then I went to community college for two years and transferred.

• 4:59Speaker 00

  And because of that experience, I wanted to show that teacher that I can actually do math, and they were wrong. And I guess the ultimate culmination there is getting a math PhD.

• 5:09Harry Stebbings?

  Sean, when you were at community college in between and you have nothing to show, you have no forms of success that you can go, well, look at me, I've done this. Did you always feel that you would be successful and that it was inevitable and that you just needed to prove it? Or were you genuinely questioning yourself in those years?

• 5:24Speaker 00

  I mean, look, I think that's a natural response when you're like a teenager and you don't know that much about how the world works. And I was nervous. You know, and my parents, to their credit, they made me work from a young age. And so I had worked, like, on construction sites for two summers, carrying wood, like, literally carrying wood around. And I had also worked in a surf store, jack surfboards in Orange County, California, in two different stores, folding T-shirts when people would, uh, they'd go try on clothes and I'd have to fold it up right behind them. It was, that was the worst job I've ever had. I vastly preferred carrying wood. At least I was learning Spanish and was outside and stuff. But when you've had those experiences, it's very, very motivating.

• 6:04Speaker 00

  I did not want to be stuck folding T-shirts the rest of my life. But on the other hand, I did have a lot of confidence. Like, I knew that I was smart. I was a computer hacker as a kid. And when you're a hacker, you learn this mentality that you will always find a way in. You will always find a trap door, a back door, a side door. If you have to parachute onto the roof, like, whatever it is, you'll find a way in. And so I had that in the back of my mind, that I'll find loopholes to get in.

• 6:30Harry Stebbings?

  In terms of finding loopholes, I did my research before this and I heard that you were a spy and worked at DARPA. You also got deployed to Afghanistan. Can you take me to maybe how that shaped you in such a meaningful way, given the impact that it is on any person? How did that time shape you?

• 6:49Speaker 00

  Look, I worked at DARPA and I deployed to Afghanistan. I was never a spy. For me, because I had such a weird academic background, if I enlisted in the army or in the navy or whatever, I would just get the worst job possible. I mean, sure, there's IQ tests and you can go try to become a SEAL or something like that, but if you don't make it, you're going to get a really bad job. And so I had this, I wanted to have service, but I didn't know the right way to do it. And then I met this woman named Regina Dugan, who was, she was running DARPA at the time, and she was trying basically an experimental program of let's just go find some really smart, crazy young people and give them basically unprecedented access, like, I mean, genuinely insane access, you know, regular meetings

• 7:32Speaker 00

  with the Joint Chiefs of Staff and ability to call Black Hawk helicopters to take you around. And it was a very formative thing. I, and look, there's a lot of evil in the world. Like, there's real evil in the world. And I think a lot of people just don't, they can't process that. People today in the West cannot fathom that there's real evil in the world. And I can tell you very certainly that there is evil.

• 7:54Harry Stebbings?

  What is the most real evil in the world today, do you think?

• 7:57Speaker 00

  I think the most real evil right now is probably the Iranian regime. The Iranian regime is happy to oppress their own people. My wife said Persian Jew, her family's from Iran, they left in the revolution in 79. They're happy to oppress their own people. They're happy to oppress the people of Gaza. They're happy to oppress the people of Israel. Something that people don't realize about Iran, but Iran is deeply responsible in the global drug trade. Like, the global drug trade would not be anything close to what it is today if it weren't for Iran. Like, the cartels in Colombia and Venezuela basically report into Iran. Iran is, handles most of the money laundering for them and coordination.

• 8:40Speaker 00

  Processing of a lot of like the precursor chemicals, stuff like that. When Russia invaded Ukraine, for the first year or so, a lot of the munitions were coming from Iran. When America was fighting in Afghanistan, Iran was like deeply supporting the Taliban. And look, evil, there's different perspectives to what is evil. And I will just say that this is a weird analogy. Have you ever played backgammon?

• 9:02Harry Stebbings?

  Yeah, of course.

• 9:04Speaker 00

  So in backgammon, when you're losing, like when you're behind, the optimal strategy is to create chaos. If you're losing by a lot, you keep a lot of your pieces open. You want to create chaos. You want to make it so that someone will likely hit you. The way that, the only way you have a chance of coming back when you're really far behind is to create chaos. Iran basically created backgammon, the Persian Empire a millennia ago or whatever. And that's the Iranian philosophy when you're losing is to create chaos. So they're creating as much chaos in the world as they possibly can.

• 9:35Harry Stebbings?

  What would you do differently in terms of US activity that you are not doing today?

• 9:40Speaker 00

  For the US specifically, I think that the Obama administration and then now reinvigorated by the Biden Harris administration. They've had the, literally the worst possible Iran policy, which has been appeasement, believing that they can turn Iran through nice words and actions. You know, so Trump froze most assets of Iran that he could, had deep sanctions against them, made it hard for them to sell oil. Made it hard for them to operate in the global economy, basically had them financially on the brink of collapse. And the Biden Harris administration immediately went back to the Obama doctrine of let's just sit them down at the negotiation table.

• 10:23Speaker 00

  Let's unfreeze all their funds, let's remove all the sanctions. If we treat them well, then of course they'll come into our fold. To take that even one step further, like there's obviously a ancient rivalry between Saudi Arabia and Iran. Uh, you know, Iran is the ancient seat of Shia Islam and Saudi as the kind of origin of Islam. But the modern hub of Sunni Islam, there's this ancient, ancient rivalry. We have somehow when Biden came in, he was very tough on Saudi Arabia and very loose on Iran. From my perspective, Saudi Arabia, despite what the media says, Saudi Arabia has been modernizing at an unbelievable rate.

• 11:05Speaker 00

  I'm personally a big fan of MBS. I think he's been a fantastic reformer. Sure, Jamal Khashoggi was a horrible, horrible thing, but just if you look at the rate of progress, Saudi has been unbelievable. Twenty five years ago, Saudi was the number one funder of Muslim Brotherhood and like the Wahhabist madrassas. Today, there's very little of that in Saudi and Iran is at the root of almost all chaos in the region. I find it crazy. When Biden came in, he, one of his first statements was condemning MBS, saying he won't meet with MBS. These things are gifts to Iran. They show Iran that they can just keep pushing and pushing.

• 11:44Speaker 00

  I'll take this one step further. Since October 7th, Iran has carried out Iranian proxies have carried out over 300 attacks against US soldiers on US bases or ships in the region, directly attacked US interests over 300 times. And despite that, the US is still releasing funds that had been frozen back to Iran. Like, these things are insane. It's honestly, the policy has been insane.

• 12:07Harry Stebbings?

  Is Donald Trump the best chance we have of alleviating the either current World War III or soon to be World War III in the Middle East?

• 12:16Speaker 00

  100%.

• 12:17Harry Stebbings?

  Why? Because honestly, Sean, I want this show to be like very honest with me. Like, I don't know anywhere near what you know. But I speak to a lot of people and some say 100% and some say he is erratic. And with the power that he has, that erratic nature just creates more volatility.

• 12:33Speaker 00

  And I want to be clear. When I say 100%, I mean compared to Biden Harris administration. I don't mean compared to all possible options. You know, I wrote this long X post eight years ago. I was incredibly afraid of Trump and, you know, voted for Hillary and donated to Hillary. And four years ago, I didn't vote because I didn't like either option. The things that have really changed my mind are, one, I mean, like, if you go back to 2016. The number one reason why I was afraid of Trump was because in 2016, he was supported by Russia. Like Russia wanted Trump to win and they wanted Hillary to lose. And that manifested as like there were all these fake news bot farms, putting out content on Facebook.

• 13:18Speaker 00

  Hilary Clinton's emails got hacked and then released in kind of two-step process at the worst possible times. Like, you know, the bulk in October, right before the election. And from my perspective, as given what I've done in the past and working in intelligence and stuff like this, when your enemy or when Russia wants Trump to get elected so badly and like concurrent to that, there was the Steele dossier and stuff like this. I believe the lie, I believe the media narrative that Trump was corrupted, that he was owned by Russia. If he wasn't, that it'd be easy for them to own him and that he had no experience in foreign policy and would just make all the wrong decisions. If you look at what actually happened, I think that Trump was the best president

• 14:01Speaker 00

  in the modern era at dealing with Russia, the best at dealing with Iran, the best at dealing with China. I'll give you a couple of examples, one for each. With Russia, there's this famous NATO breakfast video where Trump, this is a few years ago, five years ago or so. Trump, sitting down like at a NATO breakfast, he's meeting with the kind of top German diplomats and he goes off on them for a few minutes and says like, "You guys are making every mistake possible. You're owned by Russia." He says, you know, "Your energy supply is owned by Russia." I believe it's 2% that basically that you're supposed to spend 2% of your GDP on defense. Like that is what's laid out in the NATO guidelines and you're only spending 1.2%.

• 14:44Speaker 00

  America subsidizing you guys by spending 4% on defense. If you don't fix this, like Russia's gonna invade and you won't be able to do anything about it. He lays all this out and the German diplomats are laughing at him. They're literally laughing to his face. They're smirking, these arrogant smirks and just laughing at him. And that, I think, is just symbolic for how the liberal elites treated Trump on everything of like, this guy was out They're saying the actual truth and predicting the future. But because the media was so anti-Trump and these liberal elites were so clueless. They were just happy to laugh in his face and believe their lies.

• 15:23Harry Stebbings?

  Does that not prove his ineffectiveness? I mean, that is not a story of effectiveness of Trump's diplomacy, though. If they're laughing in his face and he's letting it happen, it's like.

• 15:31Speaker 00

  I think that's a very different thing. I think that that proves the failure of European policy and of the left's policy. So I think that, sure, with Russia, he was not effective at convincing Europe to to actually do the right thing. With Iran and China, Trump had more unilateral abilities. And Trump just did the right things. Like with Iran, he sanctioned the shit out of them and he froze their funds. And, you know, he got Abraham Accords for Israel, which weakened, which weakened Iran's hand in the region meaningfully. And so at least Trump knew what needed to be done. I think that the Obama foreign policy carried on by Biden Harris. They don't even know what to be done.

• 16:15Speaker 00

  And if I were to try to put it in simple words, like the way that Western diplomacy works. Like when England and America are doing diplomacy in the 1960s. If Harry and Doug go and sit down in a room and argue about what the terms of some deal should be. And get to the end of it and look each other in the eye and say, okay, these are the terms. We have a deal, right? And you look each other in the eye and you shake hands like in this backdoor doing like, that should be it. That deal should be crystallized and should actually be upheld. In the West, your word is your bond. In the East, when you're dealing with Iran, you look the Ayatollahs in the eye. They'll tell you, yeah, we're going to shut down our nuclear program. Like, yes, we're not going to invade Israel, etc.

• 16:59Speaker 00

  They'll tell you all this stuff, but it means nothing. It means absolutely nothing. In the East, your word means nothing. And all that matters is like, what actions are you capable of and what will you actually do? And Trump is the only American leader that has understood that. All of these other ones seem to. You can just go reason with people if they say, look you in the eye and say that they're going to do something that they'll actually do it. And it's, we've been banging our head against the wall on this topic for 50 years and we need to, we need to learn from it.

• 17:33Harry Stebbings?

  Sure. What would Trump do in response to now? He comes in, in the election. How would he quell it?

• 17:39Speaker 00

  So what's happening in the Middle East or where?

• 17:41Harry Stebbings?

  Middle East and then Russia.

• 17:43Speaker 00

  In the Middle East, it depends when he comes in. Like if you were to come in today, the wild card that needs to be dealt with is Iranian nuclear program and allegedly they, they have just recently obtained nuclear weapons. You get a different answer based on whether you want to deal with those nuclear weapons or not. Like if you don't care about the nuclear weapons, you're just going to accept a new world where Iran has nuclear weapons. Then basically what you do is you, this is going to sound crazy, but basically you, um, you basically force a ceasefire between Israel and Hamas in exchange for a peace agreement with Saudi, between Saudi and Israel.

• 18:27Speaker 00

  Saudi gets cyber weapons and technology as a result. Saudi will, on a few year timeframe, take over a bunch of the policing responsibilities of, of Gaza. And I'm giving you just the very, very skeleton outline. Like if you want to go the path of removing nuclear weapons from Iran, then we're at the point now where there has to be war. When Biden and Harris came in, you didn't, Iran did not have nuclear weapons. You did not have to do that. But now if you think that, that it's too destabilizing for them to have weapons, nuclear weapons going forward, then there basically has to be war. And so I think that if you were to go back in time three years, Trump had exactly the right policy to avoid all of this, which was

• 19:10Speaker 00

  weakening Iran, preventing them from getting nuclear weapons as the top two. And then creating more anchored stability in the region through the Abraham Accords and having peace agreements between Israel and the strong regional players.

• 19:22Harry Stebbings?

  Are we at war already? You tweeted the other day about being in World War III. And if so, how does that look? It is fundamentally different to our preconceived ideas of World War I and II, cyber being obviously one of the biggest.

• 19:34Speaker 00

  The calc is very simple from an Iranian perspective and also, I think, from like an Israeli perspective. From an Iranian perspective, if they knew that Kamala Harris was gonna win, then they will happily wait six months for her to be in office and then go do whatever they want to do. If they think that Trump is gonna win, then they need to do whatever they want to do now. Like, they're very, very afraid of Trump and his ability to retaliate strongly. And so whether or not war is inevitable, I would not say it's inevitable. The polymarket election odds, as they fluctuate, like, so does the, you know, the odds of a larger regional war.

• 20:19Speaker 00

  That said, I think it's unlikely to be World War III. I think it would just be a very big regional war. Like, for it to be World War III, you'd have to have China and the US directly involved with each other, and I think that's extremely unlikely right now.

• 20:34Harry Stebbings?

  You said those two different kind of outcomes that could happen, or the two different pathways that one could take, depending on who is, you know, ultimately wins the election. We had Trump in a post-assassination attempt in the most unbelievable sign of bravery and iconic image of political power in the last, I don't know, 100 years. And everyone was like, Trump has won. What an image of ultimate bravery. And now you sit here a couple of weeks later, and you've tweeted about the swing that Kamala has seen, and everyone now tells me, no, no, no, she's won it, like, Trump is defeated. Can you help me understand where we're at?

• 21:09Speaker 00

  I think it's about 50/50, and that's not a cop-out. Like, that's what I actually think are the rough odds. Candidly, I think a big factor in that is, like, just how much better the Democrats are at the mail-in ballot, ballot harvesting groundwork. Like, I think that will be the dominant variable in this election by far. That's technically legal in most places, but in the last election, happened at an extremely large scale. You know, in the last US election, there were about 30 Million more votes for the top two candidates than there were in the election before. And that was at the peak of COVID in an uninspiring election.

• 21:54Speaker 00

  A lot of that was basically, there was a new tactic invented of of like, as there are more more mail in ballots available, they were kind of creative, again, and like, for the most part, very legal, but very creative tactics used to go and register people to vote at old homes if they were going to vote one way and then, you know, either driving them in on buses, you know, in swing states to vote or filling out mail in ballots for them and. Do you think there's validity to Trump's statement of the unfairness of the election? Of all of the topics I've ever tried to comment on, this is the one that has the most landmines. And I've commented on some very spicy things.

• 22:35Speaker 00

  But look, I'm at a point where I care about America and so I'm just gonna say what I think has to be said, even if it's unpopular. You know, when I wrote this long X post, the number one thing that people use to deposition Trump, the number one thing is January 6th, like that is by far the number one thing. All right, Harry, I'm gonna, I'm gonna give you, I'm gonna give you the goods. So the number one thing people try to do to deposition Trump is January 6th. I tried to frame it in my X post in a very different way, which is back in 2016, Hilary Clinton said that the election was stolen, you know, against her. And it was stolen, you know, for Trump through Russian interference.

• 23:18Speaker 00

  And I gave you two examples of, you know, fake news, bot farms and hacking emails. That's not direct voter interference, but it was like pretty significant mind changing and and changing whether people's motivation to go out and vote and all that. So Hillary, to this day, still says that the 2016 election was stolen. I agree with her, like, I really do. I think that there was unbelievable tampering in that election. And something that I have learned firsthand, like I worked in the DOD for a while. I had very high clearance for. A long time. And on these most controversial topics, on the election in particular,

• 23:59Speaker 00

  there's this kind of crazy phenomenon where if you go ask people like, hey, can we look into this? People say, no, you cannot look into whether the election was stolen or not. They will not let you. And the reason why, and I think this is semi legitimate, but like, the reason why is if we find that the election was stolen, that is so undermining of our democratic process that people won't even let you go look for it. And so Hillary, to this day, still says the 2016 election was stolen. Hillary says that. Hillary's pretty smart, pretty experienced. I respect Hillary a lot. And then Trump, he also says it. I think there's a pretty extreme double standard that Hillary is allowed to say it and Trump is not,

• 24:41Speaker 00

  especially in an election where there were 30 million more votes for the top two candidates, a 22% increase for the top two. That's like statistically by far the largest jump like in the modern era.

• 24:52Harry Stebbings?

  But I think people kind of blame Trump not for his statement of there being unfair election, but for inciting the violence and for encouraging violence and an uprising around it.

• 25:02Speaker 00

  I'll get there. I'll get there. I think that the two are deeply linked. Trump questioned the election a lot. In my opinion, I do think that there were extreme irregularities in the 2020 election. And as a former cyber person who did the most advanced cyber in the US government, there was an extremely large hack happening during the election called SolarWinds, which my company was deeply involved in investigating and remediating. I personally believe that SolarWinds could have been used to directly tamper with the election results. I have tried to flag that at least three or four different ways and nobody will take it seriously.

• 25:44Speaker 00

  And some people have told me directly that they can't look into it because if they found that it. Indeed, did happen, it would be so damaging for democracy, they just can't even look into it. When that is the philosophy, when the philosophy is like, we can't even investigate if there was real fraud or malfeasance, then you're never going to know the answer. For me as an American, I think that if that's our philosophy, we're never going to get to the truth. And we might have vulnerable elections going forward. And so even having this level of view is like, puts me at great jeopardy. I don't mean from a physical perspective, but just like, this is such a controversial topic that people struggle to hear my words and hear that like, I'm not saying directly that it was stolen.

• 26:29Speaker 00

  I don't know for sure, but I do know for sure that people were unwilling to look into credible paths to which it may have been stolen. And I also know that there's a double standard for when Hillary says that 2016 was stolen versus Trump in 2020. And then with January 6th, January 6th was a horrible day, absolutely horrible day. I wish it didn't happen, but I think that if you go beyond what Hillary did in 2016, I don't think that Trump did much more to incite the January 6th insurrection than what Hillary did of denying the election results. And so I just, I think that the drawing the conclusion from what Trump said to January 6th,

• 27:09Speaker 00

  I think is a, it's not as bulletproof of an argument as I think people make it out to be.

• 27:15Harry Stebbings?

  Listen, there are a lot of parties who stand to gain from different sides winning this next election. Iran would heavily like a Harris win. I think Putin would heavily like a Trump win. My question to you, is the next election not just as vulnerable to foreign parties having an impact?

• 27:31Speaker 00

  Of course it is. And that's why, that's why I'm saying it's like, I can't predict it. And I don't even think the polymarket odds or any of the odds are that reflective because I don't think that they price in nation state activity or cheating effectively.

• 27:45Harry Stebbings?

  Who is the biggest threat from a nation state activity cheating?

• 27:48Speaker 00

  No comment right now. The civilian population really misunderstands and underestimates like how much, how much spy activity and like cheating there is in the world and just, there was a really crazy anecdote that came out about 10 days ago or so. I don't know if you saw this, but basically in the prisoner swap with Russia for Evan Gershovich, the Wall Street Journal reporter, two of the spies that got returned to Russia had been like literally out of the Americans TV show. They had been deep, deep undercover pretending that they're an Argentinian couple and they had two children and their children flew back to Russia with them as part of the prisoner swap.

• 28:33Speaker 00

  The children did not know they're Russian. They had no idea of the Russian heritage and there's like videos and photos of them getting off the airplane and Putin meeting them on the tarmac. But allegedly Putin said to them when they got there, buenas noches to the kids, literally, like their parents were so deep undercover that the kids didn't know they're Russian. Like this happened 10 days ago and that is like something that was discovered. Like people have no idea the level of sophistication of some of these things. And like that is a tiny, tiny, tiny little thing that's happened in the world.

• 29:07Harry Stebbings?

  Can I ask you, when we go back to kind of the election, did Trump make a mistake appointing J D Vance? And then it seems like it's a series of faux pas and mishaps that have been made since and it's really damaged his Trump's campaign to what extent has it?

• 29:21Speaker 00

  I think it's a complicated thing to answer because I think if, if Trump gets elected, then I think it was a phenomenal pick because I think that J D is really, really smart, really capable, would be one of the best VPs you could possibly have on the job. But in terms of getting elected, I don't think that it was the easy path choice for getting elected. I think the easy path would be someone like Nikki Haley or someone that appeals to a kind of broader and different demographic. But unfortunately, we live in a time where everything is so politicized that people don't even care who you actually are, what your Views are they everything is clipped out of context. Everything is like weaponized against you on both sides.

• 30:04Speaker 00

  I don't want this to be a partisan take. But so take with Trump, like one of the very formative clip for me was the Charlottesville clip. I'm Jewish a few years ago when he made the comment that they're very fine people at the Charlottesville rally. Like, you know, I was offended by that and I thought that was crazy. I try to really pay attention to what's happening, like to what people actually say and from first principles and all this. But even I had never seen the full clip of what he said in Charlottesville until about four months ago or so. And I tweeted about this, but he basically said the opposite. I mean, he said very explicitly that he condemns neo Nazis. He condemns white supremacists. He says that three times in this in the full clip. But somehow it's like spun to mean the opposite of what he said.

• 30:49Speaker 00

  This is happening with J D Vance. J D's comments on abortion have been more moderate actually than what has been presented to the world. He's being clipped in the most out of context, most adversarial way possible. And for this happens to Kamala Harris as well. This was happening to Joe Biden. I think Joe Biden probably does have, you know, he's clearly in mental, mental decline. But going back a few years, like some of the clips that went very viral to evidence that like were clipped out of context. You know, and like makes it seem like he's trying to sit down at the wrong time. But like, he was just maybe two seconds ahead of people like there were like, we live in this sadly in a very adversarial media environment on both sides.

• 31:31Speaker 00

  Where nobody like listens to the full length of what people say. And I think this works against J D more than it works against someone like Nikki Haley. Candidly, just because of the package of how it's delivered.

• 31:45Harry Stebbings?

  Do you think he'll swap out J D Vance before the election?

• 31:49Speaker 00

  No.

• 31:50Harry Stebbings?

  Do you think he should?

• 31:51Speaker 00

  No, he's doing what he thinks would be best for America, which is having a very, very smart VP that if they get in office, like, like knows exactly what needs to be done and can help them do it. And candidly, like, we need a lot of reform in the US government. And I think JD would be much more effective at helping with some of this reform than many of the other candidates.

• 32:13Harry Stebbings?

  I spoke to a very knowledgeable, informed political figure in the US the other day, and they said, if Trump doesn't win, my real fear is that will be just incredible civil unrest, like, his supporters will go nuts. Is that possible?

• 32:28Speaker 00

  Look, I think it's way more likely the other way around. I think almost everything that we've been told about the world has been, like, the opposite has been true. Like, the BLM riots and, like, anything that Antifa does is way more extreme than what the far-right has done. I don't believe it.

• 32:44Harry Stebbings?

  You think there's civil unrest if he wins?

• 32:46Speaker 00

  I'm not saying there will be. I personally think that there is more risk of civil unrest from the far left than from the far right.

• 32:55Harry Stebbings?

  Can I ask you, something I love about you, Sean, is you're not afraid to say how you feel and answer tougher questions. Do you think we live in a society where you have freedom of speech?

• 33:05Speaker 00

  Great question. I think there's a huge difference between having freedom of speech, being willing to use it, and having lots of information warfare. And so just to unpack this quickly, like, I don't think we had freedom of speech before Elon bought Twitter. Things like Trump getting banned from X and many, many right-wing voices getting banned from, you know, Twitter at the time. I think we're moving away from free speech very quickly in Europe. And let me be clear, I think we have free speech in America right now. I don't think you have it in Europe. It's pretty crazy. I mean, and first of all, do you agree with that or not?

• 33:39Harry Stebbings?

  I do agree.

• 33:40Speaker 00

  There was this, like, this one was crazy, and most Europeans don't even know this stuff is happening because you can't talk about it. So maybe, like, two months ago or so, there was, like, the final legal proceedings of this, just like, one of the most horrific rape incidents I've ever heard of. It was a young woman, I'm almost certain it was in Germany, basically like a young white Girl was in a park at night, basically a group of four men who were migrants. All raped her, all four raped her, then they let her go, but they had been sending WhatsApp messages to their friends, saying that there's like a white girl in the park. Come rape her. And so she start, you know, she started running away.

• 34:20Speaker 00

  She made it to another group of men. I think this one was three. Those three men all raped her. Then she started, she got away, she started running away. Another group of two men found her, they raped her. Then she got away, she kept going, another group of two men found her and they raped her. So she was raped by eleven men in the park in one night. I think that seven out of eleven had, there was video evidence of them, or at least photographic evidence of them. I think nine out of eleven had DNA evidence, like where there was semen in the woman. So like the most evidence you can possibly have, after that happened, like after sentencing.

• 34:59Speaker 00

  I think only one of them got jail time and it was, it was like two years. I think only one got jail time. But some hackers released the contact information of the rapist, like to try to get revenge because of this. And there was some woman, she sent a bunch of nasty text messages to one of the rapists. And she ended up getting two days in prison for like hate speech and two years of community service for it. So she got more of a sentence than like ten of eleven rapists, a bunch of whom had DNA and video evidence. That is the world that Europe is in today. That's state of Europe. It's, it's pretty insane. And so people don't even know these things are happening because you can't talk about it. The media is not talking about it. It's insane.

• 35:43Harry Stebbings?

  Unpack that. Why are we not talking about it? We, we are able to talk about it. You know, why, why don't I talk? Because I am fearful that bluntly, that there is no upside to me talking. I obviously have beliefs. There is no benefit to me saying what I obviously see. Because it could challenge one of my LP's beliefs, it could challenge one of my founders. It is better to just say nothing.

• 36:05Speaker 00

  I think that this is a offshoot of cancel culture, like cancel culture primed people to become so afraid to say what they think that people just became silent as it's evolved. We've gotten to a point where like the people that made it to the top in many situations made it by not only not saying anything, but by like saying like one position is acceptable, the other side is not. And so like, there's a lot of leaders in Europe that have been maximally on the train of pro-migration or, you know, like never ever condemn a migrant. Migrants can do no wrong. And like, that was part of how they got elected to senior

• 36:48Speaker 00

  positions. And now that kind of the data has reversed, their positions can't reverse because they have too much vested in this.

• 36:55Harry Stebbings?

  Do you think migration is Europe's top challenge? When you look at the migration into particularly France from North Africa, when you look at the migration patterns that we have in the UK, Scandinavia is terrible for migration.

• 37:06Speaker 00

  So I've been to over a hundred countries. My biggest trip was in 2008, 2009. On that trip, I went to like all over the world, but I had a pretty formal experience in Sweden, where I was on the train from Stockholm to Malmo and, you know, half of the train were migrants. And it was just clear they were not being assimilated at all. And at the time, like, I don't remember the exact statistics, but Sweden's obviously a very small population, you know, nine million people or something like that at the time. And at the time, the country of Sweden had taken more, more refugees from the Middle East than America. And I don't remember exactly which country I'm drawing the lines like from Iraq or from Afghanistan

• 37:49Speaker 00

  or from the combination or but like, even though America had started the wars there, Sweden had taken more refugees, not on a per capita basis, on an absolute basis than America. And they were taking them at a rate that you just can't assimilate them into the culture of that population. You know, there's not like enough schools to teach people Swedish, you know, for adults, there's not enough jobs. Like, it started to have cracks in the hospital network, the refugees. Go and live in their own little cities and my family were migrants to America. I'm a huge, huge believer in like orderly immigration and skilled immigration. And I have empathy for refugees, but I think that it's kind of insane.

• 38:32Speaker 00

  If there's an idea that people can immigrate to a company and not assimilate into the culture of that country. That's what Europe has gotten wrong. Like they've let people come in with open border policies and not assimilate. And now Europe doesn't have, is, is on the verge of not having European culture anymore. It'll be, they're importing, you know, the culture of North Africa.

• 38:52Harry Stebbings?

  Do you think it is immigration that is the problem? Or do you think it is simply the reduction in living standards and not having enough jobs? And then everyone goes, it's the immigrants. Are we actually looking at the wrong thing for a different problem? Hey, why don't we embrace data centers from the biggest incumbents? Why don't we embrace technology as the UK? Why don't we not tax the shit out of the rich so they actually choose to be here? Are you sure Europe, Larry Summers is like, it's a museum.

• 39:21Speaker 00

  I love Europe. I try to see the best in everywhere. I think you can still have a great life in Europe going forward. I think there'll still be great companies created in Europe. I just think that the rate, like the probability of those things happening will be lower than in many other places and lower in Europe on a proportionate basis than it was 20 years ago. I think the place that's doing the best right now of anywhere is probably Dubai. Like UAE is

• 39:48Harry Stebbings?

  Crushing.

• 39:49Speaker 00

  You go, just go look at what they're doing and their policies. Like they're doing better than anywhere. And so, yes, I think Europe is on the way down. You know, I think the whole West is in decline relative to the East. But I think you can still have a great life and there's still a lot of opportunity.

• 40:05Harry Stebbings?

  We mentioned kind of being cancelled or feeling like I was being cancelled. People tried to have you fired.

• 40:11Speaker 00

  Yes, that's true.

• 40:12Harry Stebbings?

  Talk to me about that and, and how did that go down? Like you called into an office and said, hey, some important people have tried to get you fired.

• 40:19Speaker 00

  I'm not, I can't, look, I'm not going to go into all the details. Many, many different people tried to get me fired in many different ways. Look, After October 7th, I was one of the most outspoken people in the world and one of the first. Yeah, people don't like that. Or I'll give you a more recent experience, not about myself, but in my inbox, the last, you know, I feel happy that I got spared from this, but in my Sequoia inbox, the last 12 hours, 20 climate people have emailed most Sequoia partners saying that like Doug Leoni is problematic for supporting Trump and that Trump has anti-climate positions and they don't know how they can support, how they can believe that Sequoia supports climate anymore. But just really quick, like,

• 41:03Speaker 00

  like 20 people, obviously there's some climate mailing lists, there's some climate group and they basically all sent the same language, but they're trying to cancel Doug for supporting Trump because of Trump's climate policies. And it's like, obviously it's not going to work. It's Doug Leoni, but I just find it crazy that it's like one partner in a firm that has made great climate investments. It's this cancel culture ideology and it's this belief that, you know, like someone disagrees with you and so you can just send an email and maybe someone will take action on it. I just think that's very sloppy and I hope we can get back to a point where we can have civil, civil discourse, civil debate, not assume that every side is stupid or wrong or villainous, like.

• 41:46Harry Stebbings?

  I would really love to see that meeting happen. I would love to see Doug called in and sat down and told that you're a naughty boy.

• 41:54Speaker 00

  I don't think he, I don't think he will.

• 41:57Harry Stebbings?

  I, I think somehow it might not happen. I, I do have to ask, I spoke to many of your founders and they said I had to ask about this. They said, you have to ask what he thinks about DEI. This is one of the most important things to us. And how he feels should be spoken about more. So when it comes to DEI, how do you feel?

• 42:14Speaker 00

  Oh man, good question. First of all, I think that the modern paradigm of DEI is toxic, woke ideology that, that is literally cancer for society. I'm not going to mince words with that. But I think that's, I think that DEI means something different than what Mark Cuban thinks. I, I think that. You know, D I is not diversity. And I deeply believe in diversity, like diversity matters a lot to me. D I, like one piece of is equity. And the definition of equity is not creating equal opportunities. It's to have equal outcomes. That is insane. The idea that no matter what someone's work ethic is, or no matter like what their talent is,

• 42:59Speaker 00

  that everyone should have equal outcomes, like that is communism. That will literally destroy the West from inside. And so I have this kind of, I have this really polarized views where I am very supportive of diversity and have been a champion of diversity my entire life. But D I means something different than people think it does. Like D I means you can have quotas against hiring white men.

• 43:25Harry Stebbings?

  A lot of journalists say, how many female founders do you have in your portfolio? Do you think that is the wrong question to ask?

• 43:31Speaker 00

  I think that that's a fair question to ask. It's helpful to have reminders. You should go hunt for new opportunities like outside of your base network. And, and like, it's helpful to have reminders of like, oh, wow, you only work with white men. Like, that's a good, it's helpful to see that statistics. It's kind of a reminder that, hey, maybe I'm doing something wrong. But I will say there is a venture fund that I know very well. It is not Sequoia, that for a period of time had a policy that every investor was supposed to back at least one female founder per year. Even if you did zero investments, it's like if you did zero investments in that year, you were not meeting that policy.

• 44:12Speaker 00

  And so I just, for me, my issues are more with like poorly implemented policies.

• 44:18Harry Stebbings?

  How do you feel about the pronouns and the he, her compliance stuff that we have to do today?

• 44:24Speaker 00

  I have no issues at all with people living their lives however they want. But I have strongly allergic reaction to imposing your views on other people. With the transgender stuff, the things that, the issue that I think is really wrong is.

• 44:45Speaker 00

  Basically how we're handling transgender issues in schools. And the idea that like, schools don't need to report to parents. You know, if a twelve year old child says they're transgender. In the most extreme, that like, affirming children's gender is taken into like custody battles in Canada. And other places, and it can even be seen in the most extreme case as child abuse. To not affirm your child's gender. And like, just things like that are really insane to me, especially for twelve year old kids. I think that that is a batshit crazy flock.

• 45:24Harry Stebbings?

  Did you see Elon's interview with Jordan Peterson where he said about the loss of his child to kind of the woke mind virus and this?

• 45:31Speaker 00

  I didn't watch the full interview, but I watched part of it.

• 45:34Harry Stebbings?

  What did you think?

• 45:35Speaker 00

  So I have two sons and I hope to have more kids. For me, I think that if I felt like I lost a child or had a damaged relationship with a child because of what schools or the state did, I would, I would be beyond furious and beyond pained. That's like the crux of what it comes down to is if other people are able to groom your child, that is not okay to me. But on the other hand, if you do like genuinely have a child that is transgender, I think they should be supported.

• 46:11Harry Stebbings?

  Where would you want your children to grow up, Sean?

• 46:13Speaker 00

  Israel.

• 46:14Harry Stebbings?

  Why?

• 46:15Speaker 00

  This is gonna sound crazy. I want my kids to grow up a lot of resiliency and grit. And when you're under attack and misunderstood and stuff like, it is a shield from all of the insanity that is happening in the rest of the world. And so even though they're physically under attack, you know, and there's, you have to go into the bomb shelter regularly when rockets are fired and Iron Dome has intercepted them. Growing up in Israel gives you a shield against information warfare. Because when you're on the receiving end of information warfare all the time, every day, it shows you what the tactics are and makes you immune to it. Growing up in that environment gives you.

• 46:55Speaker 00

  You immunity against complacency and laziness puts a chip on your shoulder. It shows you what the world actually is. It gives you a sense of camaraderie to be amongst a community where kind of everyone is going to do the same thing. And that if if you don't cooperate, then you won't make it.

• 47:15Harry Stebbings?

  Why do you not move the family there then?

• 47:17Speaker 00

  Well, I am buying a house in Israel right now. I close on it soon.

• 47:21Harry Stebbings?

  Do you fear for your safety in the US?

• 47:23Speaker 00

  I do, especially because of how outspoken I've been. I get recognized pretty regularly now. It's kind of insane. You know, I've had dozens of death threats, some of which were pretty credible after October seventh. Fewer now than like at the peak when I was really, really active. And simple things like whenever I'm in an Uber, I don't ever want to mention Judaism or Israel. And like, these are very simple things, but I mean, first of all, there has been a lot more Jewish hate crimes in the West in the since October seventh than people realize. It is not reported on. There are murders of Jews that are not reported on. Like, I know of two people that were murdered that is not is barely reported on by the mainstream media. It's insane.

• 48:06Harry Stebbings?

  Why?

• 48:07Speaker 00

  Because it is against the narrative. If you go report that a Jewish dentist in San Diego is stabbed to death by a patient named Mohammed. This actually happened, a Persian Jewish dentist who my family knows in San Diego was literally stabbed to death by a former patient named Mohammed. Like just randomly, it was not reported and it was not reported as a hate crime, et cetera. Because it's just, it's against the narrative and there's media capture on one side. And there's actually been quite a few incidents like that since October seventh, and they are not reported. And on the opposite side, the things have been reported out of proportion, but anyways.

• 48:42Harry Stebbings?

  Can I ask you, how do you get away with the things that you say, Sean? I mean it in the nicest way, but within Sequoia, it is a firm. You have to toe the party line often. You don't. How?

• 48:53Speaker 00

  Um, well, you should ask Ruloff, but look.

• 48:57Harry Stebbings?

  Did they sit you down and say you have special microphone access?

• 49:01Speaker 00

  Look, I could get fired at any moment. It's possible. I think Sequoia is a really special place. I think it's a more special place than people realize. Part of the secret of how Sequoia has stayed so successful for so long is by having a culture where you can have people with opposite personalities, opposite points of view, that still work together really well. You know, like Mike Moritz and Doug Leoni could not have more opposite political perspectives or more opposite personalities. They worked together for almost thirty years and I think there were many disagreements, but like when those two guys would disagree on something and you know, have a long debate, what whatever they led to as the compromise, whatever like

• 49:46Speaker 00

  that process is polishing a diamond. Like you start with a lump of coal and through this extreme, you know, like combative process, like you can polish it into like a diamond of an idea. Why am I not fired? One, I try to only say things that I have researched to an unbelievable extent and can back up to any level of detail. Second, I try to have a lot of empathy. And so like, even if it doesn't come across this way, like I have pretty nuanced views and I try to have empathy for people. And three, I really care about my partners and try to support my partners. And so even if it doesn't come across that way, like.

• 50:23Harry Stebbings?

  Talk to me about the time you ran seventeen and a half miles to see your partners at SpaceX.

• 50:28Speaker 00

  Yeah.

• 50:30Speaker 00

  As I have an insane amount of energy I have my whole life. If I don't exercise, like if I don't just burn my energy into the ground, I lose my mind. I'm like a wild animal, feral animal if I don't exercise. And so this is something I do like a lot, like all the time. I timed it out and mapped it out and you know, it was fifteen miles and scheduled a bunch of phone calls. And I literally, yeah, ran to SpaceX in my jeans from West Hollywood. And I did phone calls most of the way while running in my jeans. And part of it was through the deep, deep ghetto. Probably really stupid to do it. I won't do it again. It was middle of the day and so I felt a little bit more comfortable, but yeah, I'm stupid like that.

• 51:14Harry Stebbings?

  Final one for the quick fire, I promise. You said we were ridiculed for investing in Axe. I'm long Axe. Total respect for for you and for Elon and for X. I love X, but it was at forty four billion. Can you paint the case for how that is a good investment at a forty four billion dollar entry price and what that needs to be?

• 51:34Speaker 00

  Well, I wish we paid a lower price, obviously. The price was what it was at that point in the public markets. Like you, when you do take private, you have to pay a premium to the public, you know, price. And so I wish it was half the price. But I think that X is one of the most strategic assets in the world. And I think Elon is the best operator in the world. And I think that usage is at all time high on the platform. I think the relevancy of the platform is at all time high. I think X is still weeding the garden, or, you know, like, just removing all of the dead weight and clearing through

• 52:14Speaker 00

  the brush before kind of the whole next gen of product ideas and like enhanced monetization of of X will happen.

• 52:24Harry Stebbings?

  What makes Elon so good?

• 52:26Speaker 00

  I think for him, many things. One, I think he is one of the greatest first principle thinkers of all time. Two, I think that he is has some of the best instincts of anyone out there. I think that people don't quite appreciate just how good his instincts are. And sometimes, back in twenty thirteen or so, he was saying that eventually SpaceX will launch Starlink, and that it would be a huge deal. Like, the technologies of how you would make Starlink were science fiction in twenty thirteen, like the phased array antennas and like, you know, the costs. And I don't think anyone could have laid out the exact blueprint of how you would build Starlink five years later back then. But

• 53:11Speaker 00

  I think he he had such strong instincts that it all would happen. And almost visually see the price changes and the technology improvements and kind of can put that together to see where things are going. So anyways, he has incredible instincts. Next thing is that I think he's one of the best reads. Of young talent ever. He is an absolute superhuman at identifying young, off the charts talented people that are from non-obvious backgrounds. Like, he doesn't need someone to be from like the most obvious backgrounds to, he doesn't need that, oh, they were an IMO gold medalist, and so therefore I'll hire them. He can go meet someone off the street and just like,

• 53:52Speaker 00

  because he's such an expert in so many things, he can ask them to go deep on things and he can assess like just how far deep they can go. And I can't begin to stress to you how important that is. And then I think one last thing is that, and this is something that John and Patrick Carlson do very well too. They all randomly sample every single part of the company at all times. So like a day for them would be, follow a junior engineering candidate, like interview that person, be the first interview and see how they go through the pipeline, join a junior sales stand-up, join like a meeting of managers of managers, like, you know, meet with the president. It just by looking at every business function on different length scales

• 54:33Speaker 00

  kind of randomly lets you basically diagnose problems in these organizations early and just gives you a lot more leverage than if you are set in your ways.

• 54:45Harry Stebbings?

  Sean, I could talk to you all day, but I want to move into a quick fire. So I say a short statement, you give me your thoughts in 60 seconds or less. Sound good?

• 54:52Speaker 00

  Yes.

• 54:53Harry Stebbings?

  Is AI overrated or underrated?

• 54:56Speaker 00

  Overrated in the short run, underrated in the long run.

• 54:58Harry Stebbings?

  How do you feel about the US selling off Bitcoin?

• 55:01Speaker 00

  One of the stupidest decisions of all time. It's just such an obvious hedge for America, like, and selling $2 billion of Bitcoin today just doesn't matter for America. But in the world where China and others basically weaken the dollar deliberately, kind of reduce dollar dominance, which they're doing right now. People don't understand how much this is happening right now, especially after the war in Ukraine, where US sanctioned Russia, Russia basically moved off swift, like a lot of oil trade is now happening in yuan, not in dollars, the petrodollar is breaking, blah, blah, blah. Like, you look at the cross-border trade in China and like the percent of it that's happening yuan now, it's now like 60% is happening yuan, which is insane compared to a decade ago. And so I just think it's

• 55:44Speaker 00

  a very obvious hedge for America is to hold Bitcoin.

• 55:48Harry Stebbings?

  Should the US stop funding Ukraine?

• 55:50Speaker 00

  I can't do this one in 60 seconds.

• 55:52Harry Stebbings?

  Take 120.

• 55:53Speaker 00

  I first visited Ukraine in nineteen ninety two. My great grandfather, Arthur Cohen, was a geologist who worked in the Black Sea. And he took my family to go visit the region after the Soviet Union collapsed. So we could go see it. Ukraine in nineteen ninety two was like, it was the saddest place I've ever been. Cause after Soviet Union fell, there was a couple of year period where there was still enough like inertia from the Soviet Union of the economy of like output of oil and commodities and stockpiles of goods, et cetera, that were being sold, that there was still some money coming in, called in nineteen ninety one. But by like end of nineteen ninety two, early nineteen ninety three, it was the absolute low point in terms of the economy there.

• 56:32Speaker 00

  And five year old kids were just begging in the street, swarming you, you know, if, when they could tell that you were from America and might have some money or whatever, like you'd go in a grocery store and there'd be ten items in the entire grocery store. Like it was very, very poor and I, I love, so kind of that was a formative experience for me. And I've studied Ukraine very deeply since I have a lot of love for Ukraine. But I, I think the war, the war in Ukraine, I think that America could not have botched the initial response more. But I think that now we're in a situation where I don't think a forever war is in the interest of the Ukrainian people. Over time, like in a war of production, the East will win.

• 57:16Speaker 00

  I think that China will just wildly outproduce munitions compared to the West. The thing that's in Ukraine's interest is to have a ceasefire and unfortunately cede some of the eastern territory. There needs to be some security guarantee with teeth that is not NATO, but is something else to have a deterrence against Russia. Just kind of doing the same thing again and just eating away more and more territory. Another landmine topic, I love the Ukrainian people. I believe in them and there's a lot of nuance around him saying, but I don't think of forever wars in their interest. Who's the best picker inside the choir? I really think it depends on the topic, like if it's a SaaS company, Pat Grady.

• 57:59Speaker 00

  If it's, you have to read someone, you only get like ten minutes. It's to read the person that is Doug Leoni. If it's a like a biotech company, it's definitely Ruloff. If it's a operationally heavy company, it's Alfred. If it's a fintech company, it's probably Andrew Reid. If it's a AI company, it's David Kahn, Sonya and Konstantin. Like it just, it really depends on the type of company.

• 58:27Harry Stebbings?

  Who's the best at sourcing? You can't give me that variant.

• 58:32Speaker 00

  Daphne Jean and Josephine Chen and Konstantin.

• 58:37Harry Stebbings?

  Which VC would you most like to swap portfolios with today?

• 58:39Speaker 00

  Nobody. I think I have a pretty good portfolio.

• 58:42Harry Stebbings?

  Come on, Pat said my moon. You've got to have a buddy where you're like, oh, I'd definitely take that one. What's your biggest miss?

• 58:48Speaker 00

  I have many, many, many misses. It's Andrel for sure. Trey Stevens and Peter Thiel led the seed round in my company. You know, I, I've known Palmer since before I started the company. And I don't know how I didn't invest in that company. It's insane.

• 59:05Harry Stebbings?

  Did you have the chance to?

• 59:06Speaker 00

  I should have had the chance to, like my, yeah, I should have had the chance to. I was right around those guys and yeah, I'm a moron for not finding a way.

• 59:15Harry Stebbings?

  What do you know now that you wish you'd known before you had your first child?

• 59:19Speaker 00

  Look, when you have kids, you figure it all out. Just do it. Go have kids. It's great.

• 59:25Harry Stebbings?

  Final one, what's been your biggest takeaway from working with Doug for these years?

• 59:29Speaker 00

  Doug is the man. I absolutely love Doug. Let's see, I'd say there's three things. One, to have a sense of humor with everything you're doing. Two, be maximally direct, you know, go for it. And when you combine those two, like being extremely direct, but doing it with love and humor, it's game changer. Next is do not waste anyone's time, your own time or their time. And related to that, as few of words as possible to get the point across.

• 59:58Harry Stebbings?

  Sean, dude, I've wanted to do this one for a long time. I cannot thank you enough for being so understanding with my prime questions and you've been amazing.

• 1:00:07Speaker 00

  You're the man. I've wanted to do it for a long time too. Uh, thank you for having me. Keep doing what you're doing.

• 1:00:13Harry Stebbings?

  I mean, that was such an incredible show to do. I want to say a huge thank you to Shaun for being so open. That is not the usual openness or level of openness that we get from guests. I think it's a real testament to him. If you want to watch the full interview, you can find it on YouTube by searching for 20 VC. That's two zero VC. But before we leave you today. When a promising startup files for an IPO or a venture capital firm loses its marquee partner, being the first to know gives you an advantage and time to plan your strategic response. Chances are, the information reported it first. The information is the trusted source for that important first look at actionable news across technology and finance, driving decisions with breaking stories, proprietary data tools, and a spotlight on industry trends.

• 1:00:57Harry Stebbings?

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• 1:01:39Harry Stebbings?

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• 1:02:22Harry Stebbings?

  And venture capital. Since forming the first venture fund in Silicon Valley, Cooley has formed more venture capital funds than any other law firm in the world, with 60-plus years working with VCs. They help VCs form and manage funds, make investments, and handle the myriad issues that arise through a fund's lifetime. We use them at 20 VC and have loved working with their teams in the US, London and Asia over the last few years. So to learn more about the number one most active law firm representing VC-backed companies going public, head over to Cooley.com and also Cooleygo.com, Cooley's award-winning free legal resource for entrepreneurs. As always, I so appreciate all your support and stay tuned for an incredible episode this coming Wednesday with Kaz at Shopify.