From Skeptic to Supporter: How This Billionaire Got ‘Red-Pilled’ by Trump

what was your red pill moment was there one specific thing or was it more of a trickle of things it was both right it's like it starts the wall starts crumbling and then it comes down all at once so for me it really started early in 2013 I started reading pirate wires and Mike salana and I thought he was a little crazy at first because he would write these articles one he wrote was about how the Ukrainian soldiers had swastikas on their helmets and the New York times photographers would ask them to take the swasa off for photos and I said that can't be right that can't be true and then four months later it was in the New York Times buried in the middle of the paper and I

kept seeing stories like that that that he would be early on and so I just started feeling uncomfortable and Queasy about what was going on with mainstream media and then in May of last year of 24 I read some article that talked about Trump's speech in Charlottesville and this has been well covered but but where he said there was good people on both sides and the article said it was completely you know propaganda and not what he actually not accurately reflecting what he said that uh that he denounced the Nazis a bunch of times in his speech and so then I went and watched that video and that was my red pill moment I think it was for a lot of

people because it wasn't just the media spinning it or politicians spinning it that was like one of the pillars of why you were supposed to hate Trump was that speech and and then you see Biden say that's why he had to run a second time and you see Obama go to you even see Biden bring it up again in the beginning of the DNC and it's one of their pillars and they clearly know that they're misrepresenting things so for me that was just that was beyond uncomfortable I was just like okay now I got to go back to First principles and look at the primary data and listen only to original speeches by people and I just realized I couldn't trust

mainstream media so I was I became I started questioning the Democrats as soon as I started questioning the Democrats I started getting a lot of Shame and anger and hatred oh the other thing that happened that was part of this journey is that my chief of staff parted ways with me after nine years in April of last year and he was the main person protecting me from myself on Twitter and he was the one who would say stay in your lane nobody wants to hear what you think about politics or San Francisco or anything other than you know your area of products and investing and with him gone I just started tweeting whatever I felt and thought and sometimes I got it wrong or it was a

little too emotional but first of all it was really fun and then second of all I found I got connected to this whole new audience of people people who are these kind of techno optimists I think you guys probably talked about it and that just brought me down this path that eventually I came out two days before the election publicly for Trump um and it was only because that's when I completely got there and I was trying to just be completely honest and authentic with myself and on Twitter at the same time and my daughters turned to me that Sunday and they said you're you're going to vote for Trump we know it and I said

yeah you're probably right and they said well then you have to go say it on Twitter and my daughter's like really in this with me yeah so anyway and then it was on the front page of the New York Post on the day of the election that I was uh this not that I'm such news but maybe it was just was their news Peg um that I was coming out for Trump and but I'll get back to your re question but what I love about my New York Times about my New York friends is that they did not give a f they were all pro comma and they texted me and they're just like oh that's kind of funny but it's one thing I kind of love about New York they didn't care back to your question on

Reed what I love about Reed was he was already getting pings from people saying what's going on with pinkis he's going off the rails he's becoming a Trumper you know it's you guys I'm sure have gone down got a little bit of that too about shamas in freeberg yeah so like what's wrong with him we got to bring him back into the fold you know he's he's should we lock him up is he crazy um and so Reed was already getting these I had a lot of anxiety about talking to Reed about it and finally Reed and I got on FaceTime and he just said I just want to start by saying I'm team Mark and I said I'm team Reed and it gets out a little you know a but

well no Americans can get along even if they disagree politically about a candidate it's probably where we need to get to especially you know now that Trump's going to be in office in a couple of days what was it like when for Biden yeah okay well just to finish the read part sorry but what what I love about Reed is that we followed that with a 4our dinner and he said I never questioned your principles he said I know you're a highly principled person and I just want to understand which principles it is and I'd like to convince you to change your mind but anyway so hold on one second so I you said something almost in passing but I just want to double click

I think part of what Silicon Valley actually gets wrong is that we don't embrace the tism and what I mean by that is everybody we're all a little socially uncomfortable we awkward I wouldn't say that we were the coolest people growing up and there's this virent form of blockers you called it Chief of Staff I think that these folks can be very detrimental which almost represent this filter between your true self and everybody else and there is this game that's played about being a gatekeeper I do think that executive assistants are val valuable administrative assistance are valuable the reason I can say this is that my EA

went on maternity leave I had and I experimented with a chief of staff Etc and now I use Jason service called Athena and I have a guy that works with me in the Philippines and it's about 3,000 a month and I can honestly tell you this guy is the single most effective administrative support I've ever had and what there is is all these opinions on what I can say or do and I think that when you look at a lot of these big companies if you look at zuck's current transformation or what you just spoke about there are all these Interlopers that seem to get in the middle of you and people's perception of

you I don't know if you have any comments or reactions to that idea yeah it's part of where I know you guys have talked about Zuck coming out as Lisa's based or his seemingly more authentic self or sharing more about himself and I can relate to it because I think we all go through this this struggle as you start to be more of a known person inside your company outside your company and you have people around you taking the edges off and I think that we're now in this time that I think we're having authenticity is having a moment now which is great for me because Reed said to me I I've if you Google me you'll see that there's lots and lots of bad things

written about me and a lot of it is my high school quote was some people have tacked and others tell the truth and I've always been kind of just committed to being honest even if it's nuanced and it's not an easy sound bite and Reed said to me early on you need to pick what the easy narrative is or the Press is going to make it up for you and he was right and they did or my competitors did so I think that now with long form podcasts and there's just more and the fact that we can kind of directly in a lot of ways Elon was the first one to directly defend himself you remember when well he fired his do you remember when he fired his whole PR team he fired

all those people there's just like there's none of that infrastructure between him and and everybody else but do you remember when he would be on Twitter all the time post PayPal trying to correct the story and just write long long diet tribes and then and then when a New York Times Reporter said something negative about a Tesla he just went off for weeks about them and and it seemed a little crazy and deranged and then you started to see that it worked like he actually and we were told don't defend yourself if something bad is written about you you're going to prolong the press cycle you're going to make the journalist angry and so we've we're now Unshackled

I teach this class at Stanford and I taught two backtack on Monday and I looked around and I saw half the plard said you know she her you know he him his and I got a little Pang of like oh do I have to watch one I'm say I'm like no I don't I'm Unshackled I'm just gonna this is just me and I'm gonna be Mark unfiltered and it's the better version of our so anyway I I'm glad that Zuck feels like he can be he can present more of his complete self out there now and I think we can get into it later but I have a lot of thoughts on how the culture is going to kind of move more towards base