Sam Lessin on Technology Trends

Essays

From the Podcast

So I guess the, the world is, like, the software world. But it's funny, I actually have more apps on my phone I use now than ever before, personally. But here's the funny thing. My home screen now is almost entirely apps I've made for myself, and I love them.

— Sam Lessin, More or Less Ep 169

... the trick is the technology has convinced you that you are the one in control.

— Sam Lessin, More or Less Ep 169

I'm not as convinced as you on that. I think actually that you have the perception of agency. Like, I wake up in the morning and I'm like, "What should I eat?" DoorDash tells me what to eat. I g- where do I go? The Google Maps lady tells me turn left, turn right. I wanna mate with somebody and, and the Hinge app tells me who to mate with. Like, like, the, the trick is the technology has taken over, but-

— Sam Lessin, More or Less Ep 169

If the cost of writing software is going to zero, there is no moat on those integrations as long as those integrations are done via APIs and not done via BD deals.

— Sam Lessin, More or Less Ep 169

I wake up in the morning and I'm like, "What should I eat?" DoorDash tells me what to eat. Where do I go? The Google Maps lady tells me, "Turn left, turn right." The trick is that technology has convinced you that you are the one in control.

— Sam Lessin, More or Less Ep 169

Uh, well, yeah, well, no, we're not, but here's my problem. I'm all for, like, higher ed reform and making different types of education more accessible and creating more pathways, and, like, amen. I am woefully uncomfortable with the technology entrepreneurs being in charge for all of this, and Alpha School's a good example. I am seeing more and more people talk about moving their kids to Alpha School.

— Sam Lessin, More or Less Ep 168

But also, listeners of the pod may also know Matt Mazzeo as a prolific angel investor in the technology industry.

— Sam Lessin, More or Less Ep 168

I do think that my understanding of the Salesforce... I mean, Marc Benioff clearly is, like, it's in- he's an interesting character 'cause in my head he's, like, not a technologist, but he's, like, an incredible salesperson, right? Like, is the interesting thing. Like, so the story I've heard, and someone can correct me in comments, I'm sure someone will, is that when he started Salesforce, it was billed as, like, this cloud CRM and this platform, but it was total bullshit. He basically went to a bunch of people and sold them each individual CRMs that were completely unintegrated, right? And they were just, like, one-off software builds, right? And, like, it was just all sales tactics, right? And so, like, it's interesting 'cause, like, in this technology world you have a bunch of people like the founders of Google or whatever that are like their resume or, like, is as engineers or as builders, right? And then you have Benioff, again has been unbelievably successful, but he's not an engineer, he's not a builder, he's a sales guy. Has the interesting distinction of being in it, but he's always getting criticized 'cause he's, like, among all the founders. He's sold stock, like, every day of his life, right? So you have these guys who, like, are like, "I'm in it. This is, like, I'm playing for keeps. I own my company." Benioff is, like, the constant sock, stock sales guy, gets shit on the internet for it. He's just a very different beast, right, than, like, a lot of what the valley is, and yet it's a really interesting s- to see him operate and still care at his age. I'm not sure I'll be caring when I'm his age.

— Sam Lessin, More or Less Ep 165

But it doesn't matter. You just do it yourself. There's no technology to it.

— Sam Lessin, More or Less Ep 165

I think this is good. Can I embrace and extend? So one, interestingly, I think if you gave everyone, you said, "All your software is now customizable," the humans will be like, "More boobs." Customizable software is not gonna be, lead to restraint. The people are gonna be like, "I want more powerful marijuana strains." Like, they don't want less powerful shit, right? And so, like-

— Sam Lessin, More or Less Ep 164

Which has been like hilariously down constantly 'cause it can't keep up with all the bot traffic. Here's the funny thing to me about that. It's a great example. Like if you said, "Hey, I'm gonna launch a GitHub competitor," that used to be like a hard thing to do. Now, it's like three people like sitting somewhere in Elon's office or something or some office around. They're just like, "Yeah, like we're just gonna like..." I just think that just changes the world so dramatically when all this stuff, you're just like, "I don't care." There's no software lock-in, right? Like it, it can be distribution. It can be anything about... Like you... But you're like, "Oh, I'm like angry that GitHub is down." It doesn't matter. It's so easy to replace.

— Sam Lessin, More or Less Ep 163

I gotta actually start playing with these things again, 'cause I just like have gone down my own like crazy version of this, where I don't use any of the software. I feel like I should... If you guys think it's this good, I'll actually spend time going back to use some of the software.

— Sam Lessin, More or Less Ep 163

It's just, like, a marketing and, like, endpoint that got popular, and for instance, OpenClaus, et cetera, helped get popular, and that's useful. It's distribution in, like, a very technical zone. There's no technology that matters.

— Sam Lessin, More or Less Ep 163

One of my favorite companies ever is Constellation Software, right? It's a fucking beast.

— Sam Lessin, More or Less Ep 161

I mean, sure. Dave, but, uh, I think Dave was my second on the deal, but, like, we had Howie over, we loved the software, that we were literally, when we were building Fin, we were using Airtable. I was like, "This product's sick. We need to invest in it. Who's behind it?" Turned out it was Howie at Etax from back in the day. I knew him from his first startup. So we put 3 million bucks in at 90 post, which Dave did support me on. It was very rule-breaking for Slow at the time, 'cause it was too far along.

— Sam Lessin, More or Less Ep 161

Tweets