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Entitled Couple Makes Things 10X Worse

Bessie T. Dowd by Bessie T. Dowd
January 28, 2026
in Uncategorized
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Entitled Couple Makes Things 10X Worse

‘She made things 10x worse’: Meghan Markle denies royal-treatment rumours, and the internet isn’t letting it go

Meghan Markle denies diva demands for UK return, but backlash grows as fans question her motives and credibility.

Image credit : Indiatimes | Meghan Markle denies diva demands for UK return

Meghan Markle has strongly denied reports claiming she made diva-like demands about her return to the UK, but the response has only fuelled more debate online, with many now turning their attention toward Prince Harry. With Birmingham set to host the Invictus Games, speculation has grown that Meghan may join Harry in the UK this summer for the one-year countdown event. That possibility quickly sparked reports suggesting she had strict conditions for her return, prompting a swift denial from a source close to the Sussexes.

Meghan Markle denies making diva demands.

Image credit : Instagram @meghan | Meghan Markle denies making diva demands.

Meghan denies diva demands claims

Addressing the claims, a source close to the couple told the Daily Express, “This is a complete fabrication. Nothing about it is true. No demands like this have ever been made.” However, instead of calming the situation, the denial seems to have made things worse, especially on social media, where fans and critics alike shared strong reactions.

Meghan Markle and Prince Harry face fresh backlash online.

Image credit : X @hmgifs | Meghan Markle and Prince Harry face fresh backlash online.

Online backlash grows

On Subreddit, “SaintMeghanMarkel”, one user wrote, “Every time she claps back at something, it means the ‘rumours’ were true. So she has to clap back and make things 10x worse 😂.”

Another added, “I also think she publishes her demands to see what she can get away with, then publishes a denial because of course, she’s not really like that, but then she goes for a whole different selection of entitled demands. So she can set diva expectations and deny the diva attitude to appear humble or ‘real’ and still get diva treatment.”

A third user said, “I actually love how she’s so quick to clap back at ‘false’ claims, because there are many claims she has not clapped back on, indicating that they are indeed true.”

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Another comment read, “Typical Meghan tactic – puts something out there and then, when the reaction is overwhelmingly negative, denies that she ever put it out there. The problem is that we’ve seen enough of her demands over the years to believe that her ‘conditions’ for returning to the UK are perfectly plausible.”

While Meghan faced criticism, some fans shifted the blame toward Prince Harry. One wrote, “He disgusts me! When he says ‘what THEY did,’ he means Meghan was caught searching William and Catherine’s rooms, and the Queen asked her to leave..” Another added, “This is my belief too, and why Harry has been so determined to get an apology, ‘they know what they did.’”

The claims of diva-like demands

This started when Rob Shuter’s Naughty But Nice Substack reported that a source said Meghan wants to be “in total control” regarding any UK visit. The source claimed she made diva-like demands, including that none of her staff are “allowed to look at her”.

Beyond requesting a “fleet of luxury cars”, the source added, “This isn’t just protection. She’s asking for a fortress. Bulletproof glass at the Games, armed security everywhere she goes.” Another insider claimed that “anyone who has any interaction with her has to call her ‘Her Royal Highness The Duchess of Sussex’. No exceptions.”

Meghan Markle’s statement fuels more questions.

Image credit : Instagram @meghan | Meghan Markle’s statement fuels more questions.

For now, Meghan’s denial stands, but the reaction shows the public debate is far from over, and this possible UK return continues to stir strong opinions on all sides.

  1. The Civil Partnership Act and Estate planning for same-sex couples

The Civil Partnership Act and Estate planning for same-sex couples

As part of Smith Partnership’s support of LGBTQ+ History Month, we will be looking back at key moments in legal history which have advanced LGBTQ+ rights. Here, we will be looking at the effect of the Civil Partnership Act 2004 and its importance to same-sex couples for estate planning purposes. 

The Civil Partnership Act came into effect on the 5th of December 2005 and enabled same-sex couples to register as civil partners and enjoy similar legal and financial protections as marriage (which wasn’t available to same-sex couples at the time). 

When it comes to estate planning, marriage provides many tax advantages which can be utilised by couples when dealing with the distribution of their estates. Prior to the Civil Partnership Act, same-sex couples were barred from such benefits. 

Here are just four of the ways in which the Civil Partnership Act has changed this position for the better for same-sex couples:

1. Gifts to a civil partner are not subject to Capital Gains Tax

Capital Gains Tax is payable on any transfers of assets which have increased in value during a person’s ownership. Prior to the Civil Partnership Act coming into effect, all gifts between same-sex couples would have been taken into account for Capital Gains Tax purposes. For example, if a person purchased a painting in 1995 for £5,000 but then in 2000 the painting was worth £50,000, Capital Gains Tax would be payable if the person wished to gift this painting to their same-sex partner in the year 2000. 

However, following on from the Civil Partnership Act, any transfers between civil partners became exempt for Capital Gains Tax purposes. Gifting between couples is often an effective tool when considering estate planning options.

2. Protection for Civil Partners where one has passed away without a Will

Where a person passes away and does not leave a Will, their assets are distributed in accordance with the Intestacy Rules. These statutory rules set out who is entitled to deal with a deceased’s estate and who is entitled to benefit from the same. 

Prior to the Civil Partnership Act coming into force, if a member of a same-sex couple passed away without a Will, their estate would not pass to the surviving partner. Instead, it would be distributed between the deceased’s relatives. 

The Civil Partnership Act amends this position by giving civil partners the same rights as married couples under the Intestacy Rules. Since this time, whenever a civil partner passes away without a Will, the surviving civil partner will inherit all (or a portion of) the deceased’s estate. 

3. Civil Partners are exempt from Inheritance Tax

Currently, if a deceased person has assets in excess of £325,000, then Inheritance Tax will be payable at a rate of 40% (unless there are any other exemptions or reliefs available).

Married couples are exempt from Inheritance Tax. Prior to the Civil Partnership Act, if a member of a same-sex couple passed away and left their estate to their surviving partner, then the value of their estate would be considered for Inheritance Tax purposes.  

The Civil Partnership Act has amended this position and now provides that any assets left to a surviving civil partner on death will pass free of Inheritance Tax.

4. A surviving Civil Partner can utilise any unused Nil-Rate Band Allowance

As set out above, if a person has assets less than £325,000 in value, then there is no Inheritance Tax to pay. This is known as the Nil-Rate Band Allowance.

Under the Civil Partnership Act, if a civil partner has passed away and has not utilised their Nil-Rate Band Allowance (e.g. because they have left their inheritance to the surviving civil partner), then the unused amount can be added to the surviving Civil Partner’s own Nil-Rate Band Allowance. 

This is a benefit which is often utilised for estate planning as it means that if all assets are passed to the surviving civil partner/spouse, then on the death of that surviving civil partner/spouse, they are able to utilise their own and the deceased’s full Nil-Rate Band Allowance and leave assets up to £650,000 without paying Inheritance Tax.

Summary

Estate planning is an important matter for couples to consider to ensure that their assets are dealt with in accordance with their wishes and in a tax-efficient manner. 

The importance of the Civil Partnership Act is that it meant that same-sex couples were treated more fairly by being able to utilise advantages enjoyed previously by only married couples. It was therefore an important point in legal history for same-sex couples. 

The Marriage (Same Sex Couples) Act 2013 extended marriage to include same-sex couples.  However, many people still choose to proceed with registering civil partnerships. From the 31 December 2019, opposite-sex couples are also able to register as civil partners and enjoy the associated benefits. 

If you and your civil partner or spouse would like to consider estate planning options to ensure that you are dealing with your assets in the most tax-efficient way on your death, contact our experts who will be happy to assist.

How YC Rewrote the Seed Playbook with Garry Tan

ACQ2 Episode

We’re joined by Posterous co-founder, former YC partner and current Managing Partner of Initialized Capital Garry Tan to go deep on how YC changed the game for company creation and seed investing, how they thought about building the “cult” of startups, and what lies ahead as the early-stage world continues to globalize and evolve more quickly than ever.

‍

Topics Covered (among others):


1. How the recruiting challenge for early-stage startups led to outside-the-box thinking

  • Peter Thiel’s “crazy” (but not actually crazy) offer to Garry to join Palantir
  • Leveraging “cult” startup culture into a magnet for specific types of people

2. Y Combinator’s path from fringe to mainstream

  • Insight that those same cult recruiting techniques could be applied at a meta-level to recruiting company founders themselves
  • Initial strong reactions to YC, and knowing they were on to something
  • The beginning of “influencer investing” with Paul Graham’s essays + Hacker News

3. The blooming of Seed as an asset class alongside and around YC

  • The landmark deal with SV Angel and DST / Yuri Milner to “auto-fund” every YC company starting in 2011
  • YC scaling from ~10-12 companies per batch to 70-80 and now 200+ per batch
  • Starting Initialized Capital within YC, and then spinning it out into one of the largest independent seed funds

4. Influencer investing and startup evangelism going mainstream

  • The impact of The Social Network movie
  • Exporting the ~”YC message” to the entire world: you can start a startup
  • The power of direct, bi-directional access to people via the internet

‍

Links:

  • Paul Graham’s Essays: http://www.paulgraham.com/articles.html
  • Hackers and Painters: https://www.amazon.com/Hackers-Painters-Big-Ideas-Computer/dp/1449389554/
  • Hacker News: https://news.ycombinator.com
  • Garry’s (great) YouTube Channel: https://www.youtube.com/channel/UCIBgYfDjtWlbJhg–Z4sOgQ

‍

Sponsors:

  • Plaid

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Transcript: (disclaimer: may contain unintentionally confusing, inaccurate and/or amusing transcription errors)

David: Hello, Acquired LPs. We are coming at you today with a very special episode with Garry Tan of Initialized Fame and before that—Y Combinator, Posterous, and has a long and very illustrious career here in Silicon Valley. We are going to talk about the evolution of early-stage investing.

Garry has seen it all. I think he started back in the early days when early-stage investing meant a $2 million Series A at a $5 million poster. Maybe that was even high. 

Garry: Yeah, it’s a while.

David: Goodness, things have changed. I’m so excited to have you here. Thanks for joining us and we can’t wait to dive in.

Garry: Yeah, thank you for having me. Big fan of the show and it means a lot to me that you’d have me.

David: Likewise that you would come on. Let’s just dive right in. We’re going to weave in the story of Initialized along the way, but we thought maybe we’d start way back in those prehistoric days of what life is like?

Garry: So, Arthur Rock.

David: We’ve already done that on the Sequoia episodes. Not that far back but when was it that you started Posterous? Was it in 2005?

Garry: It was 2008, actually. 

David: It was 2008. It’s later than I thought.

Garry: 2005 I was still at Palantir, so I had just designed the logo for Palantir and built one of the major product teams. Before that, I was Stanford Computer Engineering, and the crazy story for me is that friends of mine were starting a company. And I was the lowest of the low PM at Microsoft.

Ben: What that’s like?

Garry: Great place to start, great reach. Friends of mine were starting a company with Peter Thiel. They flew me down to San Francisco to have dinner with Peter right when he wrote the $500,000 check to Facebook. He said, “Garry, what are you doing at Microsoft? You’re wasting your time.” I said, “I wanted to work at a startup, but they weren’t startups in 2003, 2004.”

He said, “I’m so sure this is the right thing. You need to quit your job.” He asked me how much a year I made. I told him it was $70,000. He said, “Well, how about this? I’ll write you a personal check from my bank account to yours. This is your risk opportunity. Quit your job.” I said, “Thank you very much, Mr. Thiel, but I might make it to level 60 next year,” and I got on a plane and went back to Seattle. That company turned into Palantir. 

David: Oh my gosh.

Garry: I ended up joining a year later, they had hired away some of my closest friends who were way smarter than me. Bob McGrew, who now runs stuff over at OpenAI. Just so many smart people you get to meet in Silicon Valley over time. Once they hired away people smarter than, I was like, I need to quit my job at Microsoft. At the moment, when your friends are starting a business and you don’t know anything about startups, tech, or how these things are funded. You say, well, I have a real job, and you say no.

David: We’re talking about this with Kevin and Julia Hartz on the Eventbrite episode. I imagine you’re right out of college. Your parents were probably (if you even told them about this) like, no way would they let you do this.

Garry: They’re like don’t do it. That seems unsafe. Yeah. The immigrant mentality for sure.

Ben: Garry, that’s an amazing story, and it is absolutely one of survivorship bias because I want to share my story. I had a friend who was starting a YC Company. I had just moved to Seattle, and I was about to start my job at Microsoft. This friend lobbied and lobbied and lobbied. They’d come and get me to co-found the company with them.

For years, it looked like a huge mistake that I said, are you kidding me? I’d have to give back my signing bonus. I just moved here. This person told me something very similar that they would help definitely pay back the signing bonus. […] your risk thing, they’d pay for my move. But as years have gone by, that company sold for exactly the preference. It would have been completely awash.

Garry: Yeah. That’s tough.

Ben: For a while I was like, wow, that’s one of several examples in my life where I really blew it on joining something early. Sometimes, not that my choice was the right choice, but unless it’s Peter Thiel calling, the story doesn’t always end the way you’re—

Garry: Yeah. These things are crazy risky. I often think about, wow, he was willing to pay that much upfront for an engineer. The rest of my career—even as an investor today—is now actually the inversion of that. Which is now I realize actually, it’s the software engineers, designers, product people, and the builders who create the future. That’s why we’re able to do early-stage at all is that we look a lot more like them at that stage and so they’ll pick us.

On the flip side, because I can still code a little bit and I still do design. I’m probably better at marketing now than I was 10 years ago.

David: You’ve diversified your skillset.

Garry: Yeah. That’s right. We look more like them. Then that’s the cool thing. I think that fits with the overall series. It’s like we’re talking about the traitorous eight—sending real typewritten letters across the country to financiers who were totally different from them. Now, what we’re talking about—what you guys do and what we’re doing—is we’re no different. I think that time was for venture capitalists to say we’re set apart, we’re different.

David: We’re in this ivory tower.

Garry: Yeah. The ivory tower is different. There’s actually a ritualistic aspect that I was talking with Geoff Lewis at Bedrock. He has this theory that is really interesting. There is something to be said for I’m walking up the steps of Sequoia, this is what legends before me did, and I can be a part of that.

Now it’s Zoom. If anything, now it’s flipped. Now it’s about the one on one conversation that you can have right here. That’s why you have the rise of influencer investing. I know, we’ll talk about it later, but that’s part of the reason why I think YouTube is so important, for me anyway. I’m investing very deeply into it because I think it’s a very interesting innovation in the course of how ventures are created.

David: VCs historically take a long time to catch on. YouTube was founded right around this time that we’re talking about, and here we are in 2020 and people only just were starting to catch on.

Garry: 2005, yeah.

Ben: Garry, you talked about your time as a builder, and we’re going to put a pin in this influencer investing and definitely come back to it because I think it’ll be a nice way to round out the full story. Take us through founding Posterous, leaving Palantir, how you raised money for that, and how you went about getting enough proof that there’s a there, there to invest more of your time.

Garry: There’s nothing quite like seeing a super early-stage startup for your own eyes. Actually, I’ve always been really thankful for my time working with Stephen Cohen, Joe Lonsdale, and Alex Karp—just the founders of Palantir. Being able to build software from scratch. The more subtle interesting thing that I feel like I learned was how important it is to basically continue to hire people way smarter than you actually.

The cult making and the mythmaking of the startup very early are really underplayed. I don’t feel like people talk about it enough, and Palantir, I think remains very good at it. The only cult that was stronger than our cult was the Facebook cult (I think). But it’s interesting to see. Years later, that’s an order of magnitude bigger as a company, which is fascinating to me. I think that actually is directly proportional. How strong your cult will result in how big your company ends up being.

Assuming you’re in the right market and 10 other things that you need to survive. You need to be one of those survivors. A lot of things have to break your way.

Ben: What’s an example of something that was done at Palantir to help build that cult brand?

Garry: Honestly, I think the simplest thing was even just trying to get the smartest, most capable, and hardworking people, which sounds really stupid simple. It seems like everyone should do that, but honestly, people just don’t. When you think about hiring, the mistake that a lot of founders make—and honestly, I made this mistake at some level too when I worked on Posterous—was who can I get? And that’s the wrong question.

You should start with who is the smartest person I know, and it doesn’t matter where they’re at. Because if I get them, then our self-fulfilling prophecy becomes destiny. If I don’t, then it doesn’t. I’m not doing myself or them a favor by not going after them. We would just go. 

People would pass out yellow legal pads, and we would force everyone to step away from their computers, and it’d be like, write down the names of 20 people who were the smartest people you’ve ever met in any walk of life. It didn’t have to be engineering, design, or whatever. It was just, who are the smartest people you know in your life. We take it into a backroom and cross-reference it and then those are like our hit list. It’s like let’s go get those people. We’re going to take them to dinner, we’re going to take them to lunch, we’re going to meet them, we’re going to chop down the tree, and we’re going to go get them.

David: That mindset leads to doing things like what Peter offered to you. I can’t believe I’ve never thought of that before. Yeah, you were ungettable. You were at Microsoft, but what if you just offered to personally cover the gap in your salary? It didn’t work for you then, but a certain number of people, that’s going to work with. And if you’re not in that mindset of okay, I don’t even go to try to get this person. Well then, you don’t know, but once you’re like, no, I’m going to try and get them. Well, what can I do?

Garry: Yeah. It just compounds from there because smart people want to work with smart people. I think that is testament and credit to what they’ve been able to build over the years. That becomes a self-fulfilling prophecy and then self-impelled because if you have a group of smart people who are very driven, it’s a magnet that attracts a lot more people. Even if they know nothing about the mission.

Past 30 or 40 people, they started doing really awesome campus hires. That is actually very, very hard for companies to do. I actually haven’t seen anyone do it that early. It tends to be in the hundreds of people by the time they feel like they have the cycles to do it. But if this is a 15-, 20-year business, it actually is really smart to start on that campus hiring sooner. And then it pays off in 2 or 3 years when you get the Stanford section leaders for 1-6, X, A, and b.

You have the best people from CMU. You have the best people from MIT. Generation to generation, the software engineers know. I need to go there because the smartest person I knew from that year went to that company.

Ben: You’re surrounded by all these incredibly smart people (to keep using the word cult) at Palantir. Why leave and start a company?

Garry: I’ve always also had this thing where I can’t really follow directions. What I realized is that’s actually a founder mindset at some level. At Microsoft, it felt like I was caged. There were things that were obvious, but I was nine levels too deep in the organization to make the call. In retrospect, the most successful people I remember from the Microsoft days were amazing at hopping to level five or level six.

They knew their palm. They knew their VP. Those people would answer emails. I don’t know how they did it, but that’s actually the advice I give to incoming PM classes, Uber, Google, and elsewhere. It’s like, hey, this is an org like any other. You just treat people like people. That I wish I spent more time doing earlier in my career. It was like, oh, all of these people are just human beings and they have wants, needs, and desires. Actually, you as the youngest person in the org will know more about reality than that person who’s been in a bubble for years, and they want that.

That exchange, I think is fascinating. I think intrapreneurship is actually quite possible, but it’s probably as hard or harder than entrepreneurship. Because entrepreneurship, you just say, hey, well, I’m just going to do it this way. That was for me the inevitable. Even today, I don’t really care about power or control. What I realize is when things are broken, I do need to make the call.

That wasn’t me when I was 22, 23, and 25. Even when I was a dev lead and I worked directly for the founders. It was like, even that wasn’t enough because I do have a very intransigent streak, and when I get something in my head, I must have it. The people who are founders like that just know that about themselves, I feel like.

David: This is actually the perfect tee-up back to early-stage investing and how that’s evolved. This cult idea, I think YC really took that whole concept and started applying it to a community of founders rather than just a company. You were then leaving Palantir, going to start this company. How did you first hear about YC? You must have been applying in 2007 or 2008?

Garry: Yea, I remember the moment when I heard about the Y Combinator cult because it waltzed in the front door of our first office at Page Mill Road. It was like a CMU friend of one of the first employees. They came by for lunch. Obviously, the catered lunch things like come on by. I think we were trying to recruit them, honestly, and they had just gone through the YC batch.

It was the talk of the office afterward because they were like, ha, ha. This Y Combinator thing, it’s like $17,000 or 7%. What a bunch of chumps. That was like what people said in the office. I was like, huh, 7%. I mean, that’s not a lot of money, but they are their own founders, and they did raise money afterward. That was the kernel.

It was interesting to see the mockery because here’s our cult in opposition to their cult. Anytime cults have bumped up, it’s actually like mockery—it’s war. I think that’s one of the interesting things. It’s like that was my first interaction with the Y Combinator cult was actually like, oh, that’s garbage. I mean, that was what my team said. Even my other co-lead, he was like, I would never do that.

That was enough to get my attention because I was like, oh, that’s interesting. Today, I do this all the time where anytime there’s a very strong reaction to something. There’s something there actually. I heard about it and later I found myself applying just a year later.

David: Do you remember who that team was that you have met that day?

Garry: I think it was ZumoDrive, and they ended up selling actually. I ended up getting to know David Zhao. He’s a good angel investor now. It’s just funny actually, how these things work out, but I applied. It was really Paul Graham’s essays. I started reading Hacker News. I found Paul Graham’s essays and then, of course, once you own the media, you own a little part of the 20 million developers and the world’s brain.

I think Hacker News was actually a really powerful thing for Y Combinator and Paul Graham. He had his essays. He converted into media. I remember that the essay that did it was the one that said, hey, Garry, you weren’t meant to have a job. I was like, oh, my God. You’re like putting voice to this feeling that I’ve had for my entire life. I have just been in a cage this whole time, and I’m ready to be let free. 

It’s funny because years later, I ended up working for Paul Graham. One of the big criteria that he and Jessica would often talk about after we met a team in those 10 minutes of an interview—often we would ask, were those founders animals, and what animals were they? Which is just this crazy heuristic, but very valuable. That was the feeling I got when I became a founder which is like, oh, it’s finally my call. I have been uncaged from the systems that have prevented me from doing the things I want to do.

David: Obviously, you worked for Paul. You know him quite well. How purposeful was he about Hacker News and his essays being part of this? It’s so hard to remember now. We’re talking 2006, 2007, and 2008—so long ago in startup time, but he knew that the media gave you this direct pathway. You read that and you were like, Paul is talking to me. These are my people. How intentional was that?

Garry: I think it was highly intentional. If you read Hackers & Painters—his original book, which was his essays—he had always been that magnet for people like him. He could write about things that didn’t even have anything to do with startups, and I thought that they really resonated. I don’t intend to speak for that much of a startup done, but a lot of us were nerds and so was Paul.

He wrote about that very eloquently like secondary school and high school. That whole experience for a lot of people is like being babysat, actually. It’s like horrible crushing amounts of boredom. Plus a social dynamic that designed to torture people like us, actually. It’s like, are you serious? You zoom out a little bit and you’re like, oh, actually.

I think like that was a breath of fresh air because it’s like, oh, giving voice to the type of person like me. It’s like that’s me. I saw him go on to find success in a world that—we want to believe the real world is like college. It’s that we get to really expand our minds, follow what is true to us, and we’re deeply going down the rabbit hole of the thing that interests us the most. But the reality is, you go into the world and it’s actually like high school. It’s unfair.

David: Maybe even middle school sometimes.

Garry: Yeah. It’s worse.

Ben: It’s like the American corporate industrial complex. More people work at big companies than ever have before, and there are fewer small companies. If you look back 100 years—I’m going to be ethnocentric here—say in America, people’s professions were way more distributed. Way more people worked for themselves or the local thing and not 500,000 people for the national bank.

Garry: Yeah. You go off into this world, you take people who are founders—who are basically fish out of the water their entire lives, and then you give them a voice. Of course, you become the Pied Piper.

Ben: Oh, man. I remember sharing those religious texts. I remember startups equals growth and stuff. There are so many that I would like. I think I assembled my list at one point as these are my favorite of Paul’s writings so that I could share them, sort of easily referenceable way with people.

Garry: I still do that.

David: Gosh, you had the Acquired book club back in the day.

Garry: That’s right. All of the startups done period is also its own cult, and then we have our high priests.

Ben: Since we’re going to talk about the evolution of early-stage investing here. I want to ground some truths and some numbers. In this timeframe, when you’re starting Posterous, could you have raised from VCs before going and doing YC?

Garry: In retrospect, yes, and then I just didn’t know, honestly. My co-founder Sachin Agarwal was the lead engineer for Final Cut. I think he actually built maybe the first version of the rebuild. He’s a world-class engineer, still a world-class engineer. A great PM. For me, I had left Palantir. The funny thing about Palantir is leaving Palantir—nobody had heard of it yet.

2007, it was like, oh, the startup who knows something to do with Peter Thiel. Cool logo. Was it Lord of the Rings? What’s going on over there? Actually, that’s one of the very interesting patterns I find. When I left Palantir, nobody had heard of Palantir, nobody cared. It was another 10 years until it became a thing that people really paid attention to.

By then they were on a path. They had 1000 employees and made hundreds of millions of dollars. That’s, in a nutshell, the magic that happens. Y Combinator was the same thing. 2005, it was a fringe thing, like if you read Paul Graham’s essays. He spoke at MIT, Harvard, and a few schools. That was the very first YC batch.

David: Were you in the California batch or the Boston batch?

Garry: I was in the last Boston batch in summer ‘08. I actually lived in Mountain View.

David: No way. OG.

Garry: This was 2008. We felt like our startup idea actually had a very short fuse because the iPhone was brand new, our idea was post by email, and we both had iPhones. Flickr, WordPress, and all of these other social media services had post by email, but it was like secretpassword@ flickr.com (or whatever it was). We figured out—it was actually my co-founder who figured out—we can just do a post@ and then you don’t have to remember and then it’s just a brand. It’s post@posterous.com. Easy. 

I think Facebook and Twitter probably each had less than 10 million users still. It was really the proto era of social networks. It turned out that we were the way people wanted to post to their networks because it was easy to post photos that way. It’s funny because I can point to the month Posterous stopped growing, and it was actually the day Instagram was released.

David: Oh wow.

Garry: Instagram, on the share page today, we see it every day and use it all the time. Billions of people use it every day, but on the day it launched, we were one of the checkmarks. It was Facebook, Twitter, Foursquare, and Posterous.

David: As the share sheet official that Apple launched?

Garry: Yeah.

Ben: No.

David: Oh, the one on Instagram.

Garry: On Instagram, yeah. Today, it’s only Facebook, obviously, but back then, we supported 20 other social networks. I think we were in the top 200 sites by then.

Ben: You stopped growing when Instagram launched?

Garry: It was that plus we didn’t share the database properly. I was a bad manager. You know how startups fail. It’s like a litany of different reasons that in the confluence, recently, I did a video about why planes crash, and it’s a similar reason to why startups fail. Which is like it’s not one thing. It’s actually five different things that all come together, and they become intractable and the plane crashes and kills everyone.

This was like one of the mistakes or one of the things that we weren’t aware of. This is the fog of war part of it and Paul Graham would always talk about if you’re an engineer, it’s like being a physicist. You know what the next element on the periodic table will be, but at the moment, we didn’t understand. I remember pitching Benchmark this.

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