Freelancing for a16z with Slightly Evil Blogger Venkatesh Rao

One of my first questions, you know, you talk a lot about sparring with executives. Who do you like to, you know, intellectually spar with? Who are the best people in your life and who have they been in prior times in your life as well?

I think I'm not actually ever in the ring enough to be the boxer. I'm always the sparring partner and that's how I prefer it. It's kind of interesting that I think to the extent I need sparring partners of my own, they are basically dead people, as in, you know, authors of older books. Not necessarily dead, but, you know, and I think that's part of the formula with which I create the sort of arbitrage value because most busy people who are actually busy doing things, building companies, building products, they have less time to do like discretionary reading, especially outside of like purely instrumental stuff, right? If you're like a CEO or like a product builder, you might read a book on like how to like growth hack and do marketing, but chances are you won't read like a 13th century history book. It's very rare to find leaders and doers who have that kind of time or frankly interest. Like many of them are like super focused on like, doing stuff. So yeah, I think I spar with authors of dead books and things like that. Museums, for example, I like to go travel, visit aircraft museums. That's a big part of like how I form opinions on things like technology. So yeah, that's the weird answer.

No, I completely understand that. I feel like a lot of the time inspiring with, you know, writers that I'm reading, and that's where I learned the most from. And I, you know, it's crazy, this arbitrage opportunity, because, you know, there's other people like Ryan Holiday and Ben Wilson, who does How to Take Over the World, who are also doing a similar, you know, arbitrage the old, old books and then make it, make it new. And it's really fascinating to see that market.

Not necessarily old, though. I want to qualify that, especially because there's this subculture of like fetishizing old for old's sake, as in like books thousands of years old, Greek classics, stuff like that. I tend to actually have the opposite bias of like reading the newest stuff, which is why I'm sort of putting dead people in air quotes because a lot of my favorite authors are actually living authors. So yeah, but I think the generalization of the arbitrage pattern is there's people who spend their time on the frontiers of like exploring ideas and thoughts, and there's people who spend their times on the frontiers of doing doing things and building stuff, right? And the arbitrage opportunities to connect the former group to the latter group. And of course, you'll inevitably be in one or the other group yourself to some extent. So I think I'm a little bit over the border on the exploring ideas side as opposed to doing things side, but not as much as other people.

Got you, understood. So I guess a question for the listeners, for them to like be able to understand what does it mean to be slightly evil?

I've been actually thinking about this a lot lately, especially because, you know, the— in the crypto world, you've had the FTX, Sam Bankman-Fried thing, Elon's takeover of Twitter, all these things have like, I think, brought up the question again of What does it mean to be a high-integrity person? And the funny thing about high integrity is nobody is ever willing to cop to being like medium-integrity, ordinary, average morality person. A lot of people are willing to cop to being middling intelligence. A lot of people will, in a very self-deprecating way, say, "I'm not that smart." But nobody will ever say, "I'm not that good," right? So that's kind of interesting to me. And if you look at like how, people present themselves in terms of ethics and morals in the public sphere, there's usually like a professional wrestling-style approach where you're either the noble hero or you're the absolute heel and who's like playing up the bad guy character for almost like dramatic effect. Whereas I think this is my sort of genuine thinking of on ethics and morality. It's actually a capability and skill that you develop as you age, similar as like, you know, Intelligence, raw intelligence is something you cultivate through like, you know, practicing of skills, particular talents and so forth. So you have raw intelligence and you become sort of more cultivated intelligence over time. Similarly, you have kind of like a raw morality and you become a more cultivated morality over time. And as with intelligence and cultivating it, the chances that you'll end up at either extreme of like being a moral moron or a moral genius or moral Einstein is, very, very low. Chances are you'll be somewhere in the middle, but it's hard to cop to it. So I think there's a long-winded answer. Be slightly evil is my way of saying I'm somewhere near the— I think I flatter myself that I'm kind of average morality, but just to like not give myself too much of a benefit of the doubt, I sort of discount that and say I'm probably a little below average. So that's be slightly evil. And I think Being honest about how moral you are is actually the first step to like, I don't know, being a higher integrity person as you age.

100%. I mean, what you were saying about a wolf, an obvious wolf is better than a wolf in sheep's clothing. Like you think about somebody like Elon versus SBF, you know, we know Elon, you know, has a sick sense of humor. He's funny, you know, has a dark side to him. Whereas SBF pretended to be this, you know, good hero, this effective altruist. And like personally, Obviously I know I trusted Elon more the whole time and that's something that I try to emulate as well, which is like, I know I could be a little Machiavellian in my thinking and my girlfriend and I talk about it. We're like, if we were ever on a dating show, we would be the villains. And that's just the reality of it. And so I'd rather just be obvious and it's some vice signal rather than virtue signal. I find that's just a lot more honest in the long run.

And it's also, there's almost like a physics of morality where people signal virtues that are like humanly impossible in a way that they don't signal intelligence. Because intelligence you can calibrate, you can like compare yourself to the smart kids and the dumb kids as you were growing up in school, and you can say that's what a smart person looks like, and I can sort of like see how well I aspire to them. Whereas sometimes when people sort of present themselves morally, I get the impression that they're claiming to be 50 feet tall, and no human is 50 feet tall. It's like heights range from like, you know, 4.5 feet to like 7 feet is, I guess, a 3 sigma distribution. And it's like anybody claiming to be 50 feet tall is like off in some very weird way, right? And even the moral exemplars we admire, like, you know, Gandhi and Martin Luther King and others, if you actually read their biographies, you can see that they're like up there, but they're well within the standard, uh, you know, normal distribution. They're not like 50 feet tall morally.

100%. I'm curious, what are your thoughts on effective altruism?

I think it's like honestly a kind of clueless and sophomoric way of thinking about everything, not just about altruism, but about everything. The world does not work the way effective altruism models it. Uncertainty and randomness in the world do not work the way pure sort of Bayesian rationalists model it. So there's like so many levels of cluelessness going on. That it's like not even wrong to me. It's like, yeah, I don't take it seriously intellectually, let alone like evaluating it morally.

Fair enough. Fair enough. I am curious, another, another one of, uh, your, your lines. I love how you make up phrases. I've like begun doing that and it's just a very powerful thing. It's like when you, when you know the rules of English, you could break the rules. And so I'm very happy to make up phrases, but Cold-blooded listening is the phrase that I wanted to ask about. How do you, how do you like to cold-blooded listen? What's your strategy?

So I came up with the phrase, as I'm sure you recall, since you said you read Be Slightly Evil. It's in the essay where I talk about the movie Glengarry Glen Ross. In that, so it's a movie about salesmen, and there's The character played by Kevin Spacey, I think, yeah, he has this scene with— I forget, I forget the other guy, I keep forgetting the actor names, but there's this guy going on this whole high moral rant about how the other guy is evil and so forth. And like basically they're playing high status games, sort of like putting the other guy on trial. And Kevin Spacey just listening, ignoring all the moral judgment and bullshit, and picking out like the one actual fact in like the 15-minute tirade which reveals that the other guy actually did something like dishonest, like, you know, broke into an office or something like that. And that struck me as like a very powerful scene. It's like people say a lot, and when you listen, it's tempting to sort of like let them do the frame control. So frame control is a term in like, I guess it can be understood in Machiavellian and sort of more benevolent ways. But frame control is when you control the frame of a conversation. And usually people who do it are doing it actively. Like they're like, they're the ones talking a lot. It's really hard to do frame control from the listener side when the other guy is talking a lot. but you control the frame simply by choosing what you respond to. And you see this in like both good and bad fun. So Kevin Spacey is an example. Another example I like, again fictional, is, uh, uh, Hercule Poirot, the Agatha Christie detective. In all the books, you'll notice that he interviews, uh, like the suspects and like witnesses in the murder case just by inviting them to talk loosely about what happened. He doesn't ask them like specific questions of like "Did you see so-and-so leave the building at 7:00 PM?" Not that kind of like focused question. It's more like, "Tell me what happened." And people just in the natural course of telling the story, because telling good stories is hard and they naturally get lazy, often reveal more than they intend to. And Hercule Poirot's skill is picking up the things that are actually relevant, which are totally accidental usually for the other side, and then control the frame of the actual narrative being built. And I think this is actually cold-blooded listening. It's controlling the frame from the listener perspective, picking out the things that actually matter.

Got you, understood. So another term moving into Art of a Gig, charismatic meta gigs or charismatic mega gigs. I love that term. I've had, I've been fortunate enough to have a couple of those, which have like, you know, I worked at the Defiant, which was huge in Web3, and then now at Launch House, which, you know, has undergone issues of its own, but is also like to me, still a powerhouse and I still respect them. And, but yeah, I'm curious how has it helped you working for Andreessen and then just, you know, how can creators leverage brands that they work for in general?

So this is one of the toughest things to navigate as an independent consultant or a freelancer because typically you're in highly asymmetric relationships to people with, uh, people or organizations with a lot of charismatic influence. And it's very easy to fall into the trap of being like, um, I don't know, uncritical voices for what they're saying, or just like, uh, burging. Uh, burg stands for basking in reflected glory. Like, you know, just being associated with somebody, um, causes a lot of reflected glory. So maintaining your sort of individual, um, identity and agency in sort of what I think of as a charisma, a charismatic is it's a tough job. And when you work for like charismatic people or organizations, it's actually part of the job description because you're not valuable to those people or organizations if you don't actually manage to maintain your own identity. If you become just another, you know, yes man orbiting their little bubble of like self-validation, you're no use to them. And if they actually ask for that, that's definitely a sign to walk away. So one of the clear signs to look for is, people who not only expect you to maintain your own autonomy, but kind of demand it. So yeah, Marcus is great at that. I don't always agree with him about everything. We disagree a lot. But yeah, he has this capacity for just respecting differences and letting other people sort of own their own opinions. Another really good example is Jim Keller. He's been my client for more than 10 years. And he's a legend in the semiconductor industry, not as well known in, the consumer public world, but I got a lot of credibility in the semiconductor world simply by name dropping him. But again, that's something you have to be careful about, right? Because I am not a semiconductor guy by training. I know some stuff just by virtue of having worked in it for 10 years, but I have to be careful about like, you know, just because I walk into places with sort of Jim's halo borrowed and following me around, doesn't mean, um, that I'm like all that. Like, he has a reputation, and I have to be sort of a careful steward of, um, sort of how I play in that. So it's, it's tough. And I, I like to think of it as, uh, like, you know how Saturn's rings were formed? I don't know if you're aware, but the idea is that Saturn has such a huge gravity pull that, uh, satellites that get too close, the tidal forces rip them apart and they turn into rings. So that's kind of what you want to, uh, be wary of. Like, You can't avoid orbiting a more massive body, but you can avoid getting torn apart by them. So maintaining your own integrity is really key there.

100%. I've had that experience with a very, unfortunately, very cocky boss who, you know, wanted me to turn my face, my personal Twitter, my personal everything into their, you know, world of company. And, you know, I respected But not for me. I need to be my own person online.

There's a, there's a great line by John Boyd that really captures my heuristic on this, which is, if your boss asks for loyalty, give them integrity. And if your boss asks for integrity, give them loyalty. And it's sort of worth sitting with that line a little bit, and you'll see kind of why it works to manage your relationships with much more sort of powerful and charismatic entities, people.

So actually, that leads into the next question perfectly. Um, what are your tactics and strategies for managing your clients and how they interact with you?

So it depends a little bit, uh, on the client. Um, I do a certain amount of gatekeeping. I don't accept certain kinds of clients, people for example who expect me to produce polished deliverables. I don't accept such clients. People who are so much younger than me that they kind of start looking to me for almost like mentorship and, you know, as an elder advisor kind of person, I kind of walk away from those. There's certain frames where that's an effective way to be a consultant, but I think, for example, my band of effective consulting is probably -10 years to +15 years. I can consult for people about 15 to maybe 20 years older than me and people maybe 10 years younger than me. Younger than that, it gets too hard. Older than that, it gets too hard. So a lot of it comes down to just gatekeeping who you work with. Within that, there's some minimum disciplines I maintain. So for example, I, pretty much only charged by the hour for working with people. And there's like psychological reasons for that, because if you charge by the project or deliverable, you kind of get into other kind of relationship, relationship patterns which are not always healthy. So there's a lot of little things like that, like how you bill, how often you talk to them. So yeah, for example, there's people who I work with where I talk to them once every you know, 6 to 8 weeks for a couple of hours. There's people who I might go spend a day with once a year. There's people I talk to every week. So there's a range of tempos, but there's sort of a relationship management, that's a powerful relationship management knob of how often you like live interact with them and what you do during those interactions. So I prefer to keep those sparring sessions kind of at a particular predictable tempo. And then what I do in those sessions depends on how frequent it is. So weekly conversation client is kind of different from like an annual conversation client. If you're talking to somebody weekly, you can help them spar on like, you know, the ongoing battles they're fighting every day. If you meet them every year, then typically you're gonna be talking to them about like more philosophical, big picture stuff that they only maybe do sort of think about, uh, once a year in a leadership retreat. So there's a lot of that kind of thing. But I would say all those like little heuristics only account for maybe 20% of dealing with a relationship. Um, the other 80%, it really comes down to just getting to know the specific individual and growing together with them. It takes, I would say, 4 to 5 meetings, at least a few weeks apart, before you kind of like start to gel and your thinking styles start to mesh enough that you can think effectively together. And that's really what you're going for, where you're really trying to grow together and then it sort of becomes sustaining, self-sustaining.

100%. I struggle with that at times, doing per hour versus per project, and really find that it really depends the case. Sometimes some are, some are better than not. I am curious, moving on to, uh, this is actually a quote from, yeah, a quote from Tempo is, uh, the tempo of free agent life is driven by the broader patterns of activity in big cities, activity on mailing lists, and other such freeform substitutes for institutional rhythms. When I went freelance, I found my life wasn't driven by my boss hitting me up on Slack anymore, or like, you know, waking up at 9 for, you know, our, our daily standup or whatever. You know, it, it was driven by You know, what newsletter did I just get in my mail? You know, what do I want to read for the next half hour and go down that rabbit hole, which will hopefully inspire some writing or just keep me busy on the elliptical or whatever, you know? So I'm curious, you know, what does your average day look like? Is there an average day?

Yeah. There is more of an average day in the last few years than there used to be. And I think part of it is Until the pandemic, I was mostly relying on these larger sort of global rhythms. So like, you know, newsletters, Twitter, things like industry sector trends. For example, if you work in the semiconductor industry, there are like, you know, seasons of like big new releases that kind of drive activity. So there's like more subtle ones like that too. But what's happened in the last couple of years is Through the pandemic, public social media has become less and less of sort of a productive context to be in. And honestly, Elon buying Twitter, and one of— I'm one of the people who's kind of like backed off on Twitter as a result of that. It's almost like I was headed towards that direction anyway, and him taking over and taking the platform in directions I don't agree with is kind of like a convenient excuse for me to back off and like start rebuilding a different kind of set of patterns. But yeah, the big one actually has been a Discord I'm part of called the Yak Collective, and it's kind of just a group of us studying a lot of topics, tinkering on projects, and we've actually created like almost office-style rhythms. So we have a few study groups that meet at specific times weekly, and those have become almost the equivalent of like weekly meetings at a traditional organization. And I'm kind of enjoying that. Like it's recreated free agent office rhythms. So, and I think there's gonna be more of that in the future. More and more people are gonna like draw on these contexts.

Yeah, I, I really like that, the idea of office hours. I do a lot of coworking in New York with friends and whatnot, but the idea of virtual coworking isn't something that I do too often. But I like that. I'm not, I struggle with weekly meetings and that kind of stuff. The rhythm of it. I am curious as well, what tactics do you do to prioritize deep work in writing?

I don't believe in deep work. I think it's a bullshit framework for people who kind of want to withdraw from just being in the world and sort of responding to it live. So I don't even try. To me, it's like, all right, the world is a place I'm in and sometimes it's like stormy weather out there and I'm caught up in it and it forces me to like react second by second, and I can never get more than 10 minutes in. Other times, there's like calm periods, and I'm thinking about ideas that draw me in certain directions, and I can sit for 8 hours and do certain things. And I think this shows in my work. I'm primarily an essayist. Tempo is one full-length book I've written, but even that was derived from my postdoctoral work where I had the sort of privilege of being secluded from the world, just working on a big research topic for a couple of years. And I think there's sort of natural sort of form factors for types of work. So if you wanna write a novel, it is a certain chunk of work and you're gonna have to work in certain ways to do it. Essays are a different kind of thing. Making YouTube videos or podcasts like you do is another kind of thing. So I think you have to respect the logic of the work you're doing and not get attached to like, weird notions of deep in the sense of like, oh, I have to go off and work 8 hours a day without talking to people and only have deep meaningful conversations with a few people once a month. No, I think all that is like bullshit LARPing. You kind of have to be in the world and sort of respect the contours of the work you're trying to do.

100%. That's what I love about essays too, is I could do it, bang it out, tweet, do everything in the combination. I, I don't know, when I was younger, I thought the only way to make it as a writer was, was novels and, you know, locking yourself up in your house for, for months or whatever. But, um, those were all the main questions. I like to keep my podcast like under 30 minutes, and, um, this was really enjoyable conversation that I've been looking forward to for a long time and, uh, wasn't sure if I'd have. So thank you so much. I really appreciate it.

It's great to be here. Thanks for having me on.

All right, have a good one.