The Ledger, every show

“CEOs are surrounded by people telling them what they want to hear. That's their incentives, right? The reason why the VP is attacking me is because he's worried I'm going to make the VP look bad in front of the CEO, right? That's the concern. Whereas the CEO i…”

“The reality is interviews don't drive subscriptions. And so I do it because again, I want to push the tech product. I want people to use my podcast product.”

“There were tons of sites writing about technology, but the vast majority, all of them basically were writing about technology from a product perspective, from sort of product lens.”

“I start from business models. I start from trying to gain an understanding of a company's culture, you know, which I think goes back to a company's founding and the lessons it learned early on. And from that, look at what they do, look at what they might do, l…”

“The metric that I used when figuring out when I wanted to actually launch it was I was looking at the number of visitors to the homepage on days that I didn't post. Because those were people that were searching out new content. They were going to trajectory sa…”

“And the, you know, I've never done any marketing, you know, and this is, I think a thing where the internet is, is very, A huge benefit for publishers if you have this sort of model, because the friction for my subscribers to tell other people to try it out is…”

“The way to truly scale, the truly have impact is not to just influence the people who read you directly. It's to influence the influencers as it were.”

“I think from my perspective it's less the coming up with opinions that is difficult and more the, Trying to keep a very strong sort of guard up against like confirmation bias where, where things happen and, oh, that, that, that fits my view of the world. I'm, …”

“A friend of mine once said I love to be right, which is why I always say when I'm wrong, because that's the fastest and shortest way to be right. You know, as opposed to sort of like, double down it. So, so one, if you want to be right, like, admit you're wron…”

“That's no excuse, because to be wrong in timing is, is, is to be wrong.”

“If you're not precise and understand exactly how the business works, then your analysis may be right in spirit. But it's not right because of the details are wrong. And more importantly, the people that matter are not going to hear what you have to say because…”

“And if you had two search engines, and they had, they started out with identical technology, and one at 51% share, one at 41% share. The 51% share would grow and would improve just because they have a data advantage.”

“Whereas on the, if you go to Amazon for deodorant, You search for Dioran. You search for Old Spice, or you search for Reichardt, which means the recollection of a specific brand name is much more important than the sort of recognition of a brand, if that makes…”

“And given that these companies gain their power through owning the customer relationship, the greatest danger is always a turn in customer sentiment.”

“VC is the financial equivalent of software. It is is, is the mechanism by which to put a lot of money in upfront such that you can earn, you know, uncapped returns on the backend.”

“What used to be a series A today is a pre-seed, and then there's a seed, and then there's a series A, which is basically the old series C.”

“It turns out the music industry is actually in fantastic shape, and their revenue has been increasing a lot, and they're actually going to have, they're on pace to have like their best year ever in like the next couple of years, like even more than like the CD…”

“I could write the exact same things, the exact same sort of person I was, and I've come along 10 years earlier, or five years earlier, and would not be successful. Yeah, absolutely. I'd be writing for like, you know, some like, magazine or whatever, make, you …”

“Like BNSF in twenty-twenty-five or something, they're, the amount of free cash they've threw off in one year was more than these candies that throw off its entire lifetime. Even though you're talking about a low margin business compared to a very high margin b…”

“The best place to live is undoubtedly Taiwan. The one word everyone says for Taiwan sounds not that impressive, but the word is convenient. Like, it is the most convenient place to live.”

“Taiwan is arguably the greatest Uber Eats market ever, because there, there's amazing options. It's all delivered by scooter, so it's always like 10 minutes to get dinner and things along those lines.”

“Actually, my life is very, very optimized around. I write three pieces a week. I do an interview and I do three podcasts and all my focus and energy needs to be on that.”

“And at six months actually hit my one year goal, which was a thousand subscribers, thousand true fans, you know, it was a 100,000 dollar run rate.”

“I really try to not break news. That's actually an explicit choice on my side.”

“I had 500 Twitter followers when he posted that, and within 12 hours I had 1500 Twitter followers.”

“In November, I put a little post out. First, I simplified my model. I said, no more of this 300 level, cheap level, one price and one product. That's all you're getting. And then number two, I'm like, hey, I got a thousand subscribers. Business model works. Yo…”

“Every link to myself in a strategy email is tokenized and that token goes one link deep. So even if that email is forwarded to you can go read old stuff.”

“Half my subscribers now listen instead of read, which is amazing.”

“So if a CEO wants to talk to me, it has to be on the record and it's going to be the full transcript and the full interview is going to be available to my subscribers. And I want my subscribers to have all the same information I do.”

“And, you know, at this point, for a long time, they're actually fifty-fifty, but at this point, my annual membership is actually a fair bit larger than my monthly membership, and I think that's great.”

“I am well aware of how expensive credit cards are. It's my largest expense by a lot.”

“My goal when I started trajectory was that in five years, it could become my job. It actually became my job in a year, and I am now five years in, and, Far more successful than I would have ever imagined or made possible.”