Volition

A discussion with Linda Lebrun. We talked about Substack and it’s role in helping writers achieve financial independence, the cultural divide between traditional investing and the world of tech especially as illustrated by the choice of software tools, and the value of maintaining a private life online.

Show Notes

Show Notes:
(0:53) The most interesting Substack you’ve never heard of
(2:58) Why the serial format is experiencing a renaissance on Substack
(5:29) How conventional investing is like Groundhog Day
(7:08) How tech avoids the Groundhog Day problem and how Linda ended up jumping ship
(10:52) The journey from wood panelled Bay Street to remote Slack channels
(13:11) The age divide on tools and how people struggle between MS Office and GDocs
(18:43) Why good advice should always be controversial
(21:11) Substack’s experimental posture
(24:45) The role of a company evangelist and what thoughtful outreach looks like
(29:55) How to walk the line between a Mission Statement and evangelising the product
(33:19) Creating a better future for writer’s through financial independence
(38:06) The secret life of Linda on Twitter

References made in this episode:
- Substack, the only place to write online
- SMIRK, Christie Smythe’s serialised memoir of what happened with Martin Shkreli
- Hardcore Software, Steven Sinofsky’s stories from the PC revoloution
- TechTO, Toronto’s top tech events organiser
- Ben Horowitz’s Books on Management, The Hard Thing About Hard Things, and What You Do is How You Do
- Successories, Whenever you need the reminder to be “Working, Growing, Succeeding, Together” ;)
- Alex Danco, Patio11, Ana Lorena Fabrega, whenever I listen to what these folks say about their companies I'm always convinced there’s no better product or place to work. Masterclass in company evangelism.
- Lenny Rachitsky (Lenny's Newsletter), Lenny writes about some great stories of companies doing unscalable things in this essay. If you haven't read it before, and have any interest the world of startups, the original Paul Graham essay the newsletter references is also essential reading
- Linda's Twitter, if you’re looking for good follows and a window into a great Twitter network you could do a lot worse than perusing the list of accounts that Linda has interacted with

What is Volition?

Volition is a podcast exploring how people get things done.

In this series of interviews we talk to people about how they have built new capabilities for their organisations, their countries and themselves.

Linda Lebrun Interview
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[00:00:00] Ben Parry: Hi there. Welcome to Volition. Volition is a series of interviews with people operating at the intersection of art, entrepreneurship, and intellectual production. In this episode, I had a discussion with Linda Lebrun. Linda has had a fascinating career starting in the traditional finance world and now running writer recruitment for Substack.

We discuss Substack and its role in helping writers achieve financial independence, the cultural divide between traditional investing and the world of tech, especially as illustrated by the choice of software tools, and the value of maintaining a private life online. I hope you enjoy this episode with Linda Lebrun.

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Given that you work at Substack, I thought that it might be appropriate to start by asking you about some of the Substack's that you are subscribed to. In particular, I was browsing through, your subscription list and I noticed your subscribed to something called Smirk.

Could you tell me a little bit about what Smirk is?

[00:01:19] Linda Lebrun: Yes, and I'm glad that you asked about that one. If anybody goes to my reader profile page on Substack, it's a mile long because I do subscribe to a lot of Substacks, and I wanna say, if you see that profile page, it says that I'm subscribed to something I am paying out of my own pocket. In a handful of cases, there are people who've given me comp subscriptions, but most of them I don't have any kind of unlimited expense account.

Because I work at Substack, I am actually eating my own cooking and paying for Substack. So, if you see that I pay, I do it. Smirk is one of those. So, the backstory of is that it is written by a journalist who used to work at Bloomberg named Christie Smithe, and she was covering the Martin Shkreli trial while that was going on a few years ago. And one thing led to another, she ended up having a romantic relationship with Martin Shkreli and they're no longer together, but she, wrote, about him at the time, contemporaneously. And then later on she had very extensive knowledge and understanding of his whole story, all of the capital markets related issues around it, the pharmaceutical industry related issues around it, the justice system and prison relationship...

She wanted to write a book about that whole thing, and she couldn't find a publisher for the book because of the things that had gone on in the story and her being really a charact. In the story as well as the knowledgeable journalistic interpreter of the story. So it ended up being an ideal solution for her to come on Substack, and she is doing the book on Substack and she's releasing it as a serial and anybody who was paying attention to financial news during that whole time a few years ago, when the trial was going on and things that happened before, and just Shkreli as a public figure over time.

It's a great read that actually commits to the page some historical facts and truth where there has been some distortion in the existing coverage. So, anybody can go and read it and you know, whether you agree or disagree, if you are paying, you can read it and have access to it.

And the important thing, you know, the message around Substack is, she does not need an intermediary to give her permission to get her writing to an audience that is interested in it, which is me. She can publish it on Substack without having a gatekeeper approve of it. So, I think I'm glad you asked about that one cuz I think it is a really good example of what people can do if they have a book inside them or a story inside them and they cannot get some elite authority to rubber stamp and say, Hey, well give you a conduit to provide this to the.

[00:03:59] Ben Parry: That's an amazing story and it, I, it must be perfect for the kind of serial format as well, uh, that you can do with Substack. That's really cool. You know, she may not have got the book deal, but I sure hope she gets the movie deal because that's an amazing story.

[00:04:19] Linda Lebrun: Yes, it, it would make an incredible movie. And I think that, you know, another example of somebody who's serializing on Subsstack is there's this technologist named Steven Sinofsky and he has a Substack called Hardcore Software. If anybody is in interested in the history of tech in the nineties, he worked at Microsoft in the nineties when things were being built.

Very dynamic time and I think that he could probably without too much trouble get a book deal. But he didn't wanna do it that way. He's doing it on Substack. So I love the concept of, we're almost going back into history where serialization like Charles Dickens, was the normal way to get things out to the public and now people can do it again.

And it allows you to publish faster than hiding yourself in a garrett for two years and then coming out with a full blown product. You can actually publish as you go if you wish.

[00:05:12] Ben Parry: No, it's so cool. I've heard from some people that, the act of committing to a newsletter or committing to a podcast format and saying, w ell, I'm going to publish every week, or biweekly, or something like that. Maybe they have a book in them.

But the idea of sitting down and writing the full length book, it's just, it's just way too much. It's overwhelming, but that kind of bite size, weekly, biweekly structure is, uh, is perfect for actually getting the work done as well. It's cool. So I understand correctly, before you started working at Substan, you had a strong career in investing, uh, and you'd worked in a variety of different, uh, kind of environments with investing.

Um, I'd love to know about, a little bit more about why you made the change to Substack.

[00:06:03] Linda Lebrun: For sure, and I think this might be. Interesting to some of the listeners to your podcast who are looking maybe for perspective their own careers. My situation in the investment business was I was a CF charter holder. I was a portfolio manager for many years and the seven years before I started working at Substack, uh, myself and a few partners had a business managing pools of money.

We had a few different small-cap long only strategies. So if anybody's, you know, not into investing and doesn't know what that is, it's just you are, have a, a bunch of, uh, money from institutions and high net worth families, and you are stock picking and trying to allocate appropriately and trying to beat an index. there is much in the conventional investment industry that is like Groundhog Day, where every quarter you either beat the index or you didn't, and you write sort of a justification of yourself. And if you did, you pat yourself on the back how you were right about everything and justified your existence for one more quarter. And if you didn't, you talk about how you're right and the market is wrong, you're quite sure that next quarter will be different. So, with the pandemic, I think that the pandemic for a lot of, uh, mid-career people, middle-aged people, it kind of made us sit back and reassess. And for me, here's the thing, the, the, my job was a fun job in many ways.

It certainly is great to be able to talk to public company managers and cover them with questions and trying to figure out what is the business model of this company and which of these participants do we think is gonna be successful? It is all a great intellectual game, but if you're starting to fatigue of it, better to leave and leave that seat for somebody else who's gonna be more passionate, engaged with it, I think.

And I was starting to get burned out on it and it wasn't as fun anymore. And I think any job you can get burnt out and it's, it's not as fun anymore. And part of that was was looking at people who worked in the tech industry, and I was noticing that their work was not Groundhog Day. They were in a process of building something and every day it would get a bit better, and every day you would build something a bit more make something better for the user and maybe solve a problem and make money by solving that problem, not buy. Being one in this zero sum contest where I'm trying to be smarter than the next a hundred guys who are trying to figure out how a Quarter is gonna go. So, I was attracted to do something in tech, but again, what people are probably interested in as they listen to this is like, well that's great that you have, you know, these feelings in your heart, but what did you actually do? So I didn't have any background in it. My undergraduate degrees in Political Science, so I didn't have any, Academic or knowledge base to say that that's, you know, to hang my hat on to say that I can do anything useful. Somebody once tweeted that there are only two things that you're doing if you work for a startup.

You're either either making the product or selling the product. So, I knew which of those two things I fall. I wouldn't be making the product, but maybe I could do something that was related to selling the product. I worked in sales in various times in my life and when you're a portfolio manager and you're trying to gather assets, there's a huge, we should, We could have a whole separate conversation about how much of a sales role that is. So I started to go. Tech related events here in Toronto. We're very lucky to live in the city of Toronto where there's a burgeoning culture. Before the pandemic, there were lots of events you could go to. I would go to TechTo events. The the TechTo events were awesome because you'd be sitting there in this huge auditorium of people. they would make you meet the person on your left and on your right and you'd have to give them your elevator pitch and why are you there? And then you have to add each other on LinkedIn. It's so terrible and scary. But then you actually do start to figure out what is going on, who's hiring. And then I also just use the discipline that you always use when you're trying to break into something from the outside, which is cold outreach. I figured out some tech companies that were in Toronto and people were very kind. You know, if you reach out, I'm not gonna say that sending a cold LinkedIn message is gonna lead to success a hundred percent of the time, or even 50%.

But if you send a bunch and the person who replies to you, there's a higher chance that that person is going to get something useful out of it and you're going to get something useful out of it. Just by definition, you go into that with some, you know, good questions and with the idea of bringing value as, as well as taking value.

I'll wrap up the rest in a few sentences here cuz it's not meant to be a life story. The way that I ended up at Substack was, I knew a couple of people who had investment backgrounds and knowledge and they'd started publishing on blogging on Substack and they'd turned on paid and they were making lifestyle incomes pretty fast.

I thought that's very exciting. They probably have a long way that they can go to expand into that. Financial investing, capital markets, people writing about economics, crypto options and maybe I could be part of that. So I reached out to one of the founders of Substack and was just able to, you know, pitch we, could we do something together.

That led to a few conversations and I started working there in, March, 2021 and I was, there were about 30 people at Substack, when I joined. So, it was not, not the earliest of the early but relatively early.

[00:11:25] Ben Parry: Very cool. And so you obviously had some idea of what Tech and, uh, kind of being an operator was gonna be like, uh, before you. Before you joined Substack, you've now been there a bit over a year. So, has that year validated your beliefs around kind of how that change would, uh, transform your day to day work?

Or have you learned new things? Like what has been your experience there?

[00:11:54] Linda Lebrun: I would say I had no idea about anything, and it's been constant surprise, like whatever I would've conceptualized in my mind coming from, Remember, I didn't just go from finance to tech, I went from very traditional Bay Street wood paneled room, mostly working with baby boomer aged people. Investment business to a tech startup based in San Francisco. I'm one of the oldest people who works there, everything very online, a hundred percent remote using Slack all the time, every day. Like it's, it's been massive cultural change. But I will tell you, it does, it feels good when you are forced to figure out new things when you're dropped into what is like... people are gonna think I'm exaggerating...

but it really, it's just, it's, it's so culturally different. And it would be the same thing if somebody had worked in tech startups all their life and then went to work at, you know, Kansas City office of Wells Fargo serving high net worth families there, you know, it's, you're going into just a different milieu with different rules, different ways of communicating, very much different tools.

And I, I feel like I, you had to somewhat figure out how to use a new piece of software every day for the past 18 months, But you know what? You do it, you, you, you figure it out. So I would say I, really had no idea what I was getting into, but it also has, like, I don't, you can tell from even just what I've said about my career, that I don't really stick around in things that aren't fun.

It has been really fun. And the best part about it, this is gonna sound like pro Substack propaganda, but the colleagues have been brilliant and highly strategic and great people to get to know. So that's, that's what it totally sounds like, great places to work, but that really has, that has been the best part.

And, and like I said, an unexpected, uh, part of it.

[00:13:46] Ben Parry: I empathize with that a lot. think the experience of a new tool every day though, is, that's a, that's a classic

[00:13:54] Linda Lebrun: Yeah, it's what it feels like, like to, to a degree, I'm exaggerating and people would probably be like, well, Slack isn't that hard to use, but it's, it's more just that in this environment. You do have to be ready to just try and figure out how to use. What else can I use for an example?

I mean, I think that there is an age divide where there's a dividing line and the people younger than. Are very, very, if they're, if they're digital natives are very comfortable with Google Docs and the people older than that are very comfortable with, with the Microsoft's office environment. And I, I, I saw funny tweet where somebody, a younger person was, he had just gotten a new job and he is like, Oh my gosh, I had to figure out Word and use all these Office things because to him, figuring out the, and working with that file structure is probably so alien because, well, what, since he was in high school, he's been working on the. Google is so smart and gives all of their, software to high schools for free So there's that. And we could think of other examples like that where there's just a, a, a digital divide between how people communicate and it isn't really a bright line at a given age whatsoever. I could tell you there have been many people who my job at, at Substack, the, the core of it is reaching out to people who we think would be good on Substack and getting them to start and launch on Substack and giving them the tools and best practices. Would help them be very successful. So, in a lot of cases, am proactively reaching out to somebody who may be writing elsewhere on the internet. And a lot of the cases, those people may be older people, they might be 65 years old, and they are having a great time writing to their Facebook group. Well, you and I both know. Uh, Facebook might debate with us, but it's probably gonna be a better experience for them if they take whatever they are doing on Facebook where it's just a melee, they can't monetize it. you know, people half the time don't even see if they choose to follow their Facebook post. They won't even see it.

It's probably better for that person to come think about coming over and making a subst. And I've had cases like that where somebody in that age group starting on Subst stack, just Absolut. Took to it like fish to water no problems whatsoever. So that, I just say that to emphasize that by no means is figuring out stuff technically,

uh, going to be a cross reference to your age.

And by the same token, somebody might be 25 years old and they just did not have the opportunity to be, or the interest to be embedded in tech. But if you go into a job where you're expected to use all these tools, it will put you at a, a considerable disadvantage. Uh, if you, if you don't, uh, make a concerted effort to figure it.

[00:16:25] Ben Parry: Absolutely. I think that, uh, I was thinking about this a little bit in relation to the Figma acquisition by, uh, by Adobe that. You know, there's a lot of people who think that Adobe is, is the be all and end all of design tools. The customizability of the Adobe Suite is kind of beyond belief. It's actually, it's an incredible product that they've been able to produce.

However, there's this younger generation of designers who have often started their entire careers on Figma and they look at Adobe and they're like, Oh, it's so over tooled. That's so complicated. It's so difficult. And so they, you know, there is this theory, they're like, Oh, they bought Figma, they're gonna ruin it.

Something like that. But I think it is, it is, it does seem much more about, there's this cross-generational distaste for learning new tools, especially when they are just slightly adjacent to a tool that you feel is good enough for that purpose right now. Um, but I think as you, as you point out, it's important nonetheless, because tools are this, this crucial element of culture.

They, they describe and, uh, help to define the culture of a company and actually the question about that, I'm trying to tie it back to this question I wanted to ask you, which is, you know, it sounds like, you know, you think that, uh, corporate culture is, is pretty important. I think you've talked about it at Subsatck and I also heard you on another podcast about it in the context of small cap investment.

So, I'd love to know, you know, why do you think corporate culture is, uh, so important?

[00:18:00] Linda Lebrun: So, before I get into that, I just wanna say that's that. I like the way you put that, that is an element of culture, the, the different pieces of, of technology that we use. And an example of that, and people do. Sclerotic about I'm not going to use this new tool because of what I'm using is just fine. And there are people today using blogspot or stuck in something that is, it's, it's not supported.

It's not the best, but you, until you, unless you can force yourself to, you can try the new thing and reject the new thing sure. But for example, if, if I said: "Well, I'm not gonna use TikTok because I just read on the internet that it's for kids. So forget it. It's not for me". That I'm never gonna really understand what it is and what if. Writers that I work with, I find that some of them are using TikTok and that's helping them to promote their Substack. I'm not gonna have a good sense of what's going on. It's gonna pass me by. So there's, there's some of this like, you know, you're like Grandpa Simpson, where you feel like the, the world moved on without you, unless you make an effort to keep up.

And when you work with a lot of young people, it is easier cuz you could just listen to what they are doing and, and take suggestions, uh, from them. So, to talk about this culture issue though, the, my favorite. Writer on culture is, uh, Ben Horowitz, who, uh, wrote a number of, uh, books about corporate culture, how to structure a company, and, um, he talks about how corporate culture is about what you, what you do, and what you don't do.

And I think people think that it is. That there's a right way to do it, and sometimes they'll think it's kind of, this is kind of like advice, like if I gave you the advice to always be honest and be respectful of others and, you know, show respect to others at work, that's not, it's not interesting advice because no one would advise you the opposite.

The only thing that becomes interesting is if we, if it is controversial in some way where. There is a disagreement about what's, what's right and wrong. The example that Horowitz uses is your corporate culture might be okay when, if, uh, Linda flies to Paris who recruit a writer, is she going to stay at the uh, Holiday Inn or is she going to stay at the Ritz?

And people always think that they know the right answer. They always, Oh, the Holiday Inn, the cheaper one. That's the right answer, isn't. Well, maybe not. If she needs to get a good night's sleep and she's gonna wake up the following morning and meet some Nobel Prize winning writer, maybe the best thing to do is to, you know, have a, a First Class flight.

So the point is, and that just sounds self-serving, like, I wanna stay at the Ritz, but the point is, you've ha I think culture is what you grapple with and make decisions. It's not just like a successories post - that's a dated reference - it's not just like a poster in your office that's saying "Teamwork makes the dream work".

It's actually making tough decisions about allocation of resources and allocation of attention, which brings us back to investing because that is the central job of a CEO. CEO's central job is not in the weeds operational. He or she should be delegating that. It's, but the, the capital allocation is critical, critical, critical thing.

And I, so I think with any, any leader, thinking through those sorts of trade offs and then making tough decisions about those trade offs, I think is what shapes corporal culture. Now I'm saying all this, I'm an individual, a contributor at Substack. To be clear, I was a manager in my last job, so I have some experience of being in management, but I'm not an entrepreneur.

So any theory that I have about entrepreneurs and how they behave, um, is totally from the peanut gallery.

[00:21:24] Ben Parry: I guess then, uh, with your view from the peanut gallery, how would you describe Substack's culture in particular, given this importance and what makes Substack unique?

[00:21:36] Linda Lebrun: Oh, this is, this is such a good question. I would love to ask 10 of my colleagues this question and see what they would say about it. And I think sometimes, I think certain things are tech culture. Because I am naive of, I haven't worked in tech for my whole career. I've only worked at one tech company, so I'll, I'll think certain things, Oh, this is how tech people are, and that could be just delusional.

And this is just how this one company is, so I'll just talk about this one company. But I, I, one thing I think I, I'm not telling any tales out of school to reveal this because I think this is trait of, well run startups in general is a, a very keen and pointed. Experimental attitude, which is, and coming from traditional investment a lot of sea to the pants.

Rule of thumb, gut feeling that would go on. And really the modern way to do things is not to do that. You don't work on instincts because our instincts can fool us all the time. Uh, I'll give an example. So I remember when I first came to a subs stack, writers gave me feedback and the initial screen that comes up when you go to a subs stack for the first time, it's a welcome page and it's very, uh, clean and simple.

It doesn't have a lot. On it. It it, in some cases, if you have other people have written blurbs about your publication, there might be some blurbs that are sort of serving as social proof, but there's not a lot of ornamentation on it. And some writers would complain. They'd say, I wanna be able to have, you know, scrolling ticker or to be able to have more pictures.

I wanna my best three, I want more on the welcome page. I wanna control the welcome page and have more on it. And I remember I went back and I was like, Why does the welcome page look like this? Well, of course, The three years that they were building subs before I got there, they extensively down to the floorboards.

AB tested what the welcome page ought to look like, and this was what performed best and what we might think performs best. Must be tested against and tested against uh, uh, contact with the user, the writer, the reader, to figure out what works for an, So I would, I would just say that men, the mentality of don't have somebody who's like a God king and oh, he has amazing taste, and whatever he says goes.

It's more like if he has great taste, we're gonna take what he thinks we might take what this other person thinks, or maybe take what Linda thinks and figure out an appropriate experimentation structure, which is also a craft. not an easy thing to do, to figure out the right experiment, and then we will interpret the results.

And again, it's not so easy to, Again, there is a, um, a prior art in all this. So this was all very, very new to me. Very new to me. So I, this was an, an element of corporate culture that, and I, I say that it's corporate culture because it goes, runs all the way through everything you do if the people at the top have this mentality, and I think for our company that that's the case.

[00:24:31] Ben Parry: To switch gears slightly, um, I, I've heard you describe yourself as a company evangelist. Uh, and you know, obviously you are going out and talking to people, you're reaching out to people all the time. and so I think it makes sense in that context. But the, the phrase company evangelist also made me think of Alex Danko at shopify, anna Lorena Frebrega at synthesis School, patio11, um, at Stripe. And there seems to be something with these, this role, this evangelist role, that that brings something slightly, more than kind of marketing to it. It's slightly more than a sales and and marketing perspective. So, um, know, what do you think a good company evangelist looks.

[00:25:19] Linda Lebrun: I th comparison is flattering. When you mentioned Patio 11 and Alex Danko, because I'm, I'm, uh, fans of both of them. I think of an evangelist: what I think what people see in terms of somebody who's evangelizing the company. They might see them tweeting, they might see them going on podcasts, but there is a very important, I talked about experimentation and things being quantified and measurable.

There is a part that you may not see, which is doing cold and trying to, somebody is a prospect who would be absolutely gangbusters on subs stack to actually. Reach out to them personally and not in the form of a, of. Form letter, but a specific, you know, I have read your book. I have, uh, listened to this interview with you.

Here are the reasons why I think it would work for you to be on Substack. Here are why my theory about why it might fit into your life. But you come humbly and say, I don't really know if it would work for you. But I think maybe it would. And can we talk about it? So while you might see this, this sort of public face of evangelism with the people who is there nine to five, I think a lot of it is behind the scenes, making sure you... again, like sound, total NBA cliche, but like you're moving the boat forward every day. It's not just, okay, I, you know, I, I, I did a bunch of tweets and I made a post and that's that. What is the piece when you are building that doesn't scale is the individual one on one with, with people have to make a decision.

If you're in a conventional sales role, nothing happens until somebody takes out their wallet and pays or they, they say, Okay, our, our company will go ahead and buy 10 seats of this software as a service. Something like Substack is very different because it's not, It's on a sale.

It. When we are going out and trying to explain what it is to people so they can think about whether it might make sense for them to set up an online publication that has some pay wall gated content and provides a subscription based revenue for them, they have to think, you know, is that a fit for me? Or how can I fit into that structure? What is it, What are the pain points of my current publishing that could solve? Or if it's not something, you know, a lot of the time I will talk to people and they already have a number of other ways that they make money. It's all very well for me to say if Substack is free, if your content is free, we only get paid when you do for them, the more meaningful cost is opportunity cost.

They've got to decide if they do a sub stack, and that's one less, If they're doing a few YouTube videos a week, I think they, it would be great for them to start a Substack because then they can start to, and run on around the platform and gather email addresses. But they have to consider, well, the algo is gonna punish me if I don't do as many YouTube videos, so maybe it's not worth my time.

So, evangelist, I think it, gets into both having some kind of, uh, public facing, you know, if we do a podcast like this, gives me the chance to talk about Substack. But a really important thing is just the nons scaling part when you're fairly new in the game to try to get people to come one by one.

I always think of Chesky, who is on Substack now. He has a great post where he talks about. Some of the great tech companies of recent years and the things they did that didn't scale like Airbnb when they went door to door, handing out flyers in New York saying, Would you like to turn your house into a hotel or Uber?

When they went to the BART station and they, again, handing out flyers, just trying to get people to be one of the first people to go and get a, a ride at a car from a stranger, you don't know. I mean, these ideas seemed crazy, but they had to, they had to do some hand-to-hand combat. So I think evangelism might be, uh, partly. You know, to out in any way you can, the message, but also a lot of it is just talking to individual people. Like I guarantee you there's gonna be someone who listens to this and it's like, maybe I should start a podcast and they're gonna send me a DM on Twitter and we'll get in a conversation and hopefully they will.

So I think that's a lot of it. And that is the thing that makes work very interesting because you never know what the next conversation is going to be.

[00:29:21] Ben Parry: So, one thing that's to me about this kind of hand hand combat that you're describing is it sounds like it's halfway between sales pitch and an interview. Um, you're trying to, you know, if you've got a full sales pitch and you've got like a deep script, then you kind of run through it, maybe making modifications here and there.

Um, and then you have, and you have the other end of kind of like, there's uh, kind of basically customer interviews where you're just trying to understand something from the person you're speaking to. Um, and. So when you're evangelist, you have this mission statement that you're trying to get out there, the message that you're trying to get out there, but you're constantly also receiving feedback from these people that you're talking to.

And so does any part of your role from that angle also involve kind of modification of that mission statement or trying to, or maybe a, a refining of what that mission statement is.

[00:30:19] Linda Lebrun: I would say that there is an interplay between what Substack's user base of writers want from it and what Subst roadmap is, and this is how any consumer facing tech company would be. So for the people on my team who are doing writer development, writer recruitment, and feedback that we get from prospective writers and existing writers on Substack, I think is the most powerful. That the product team can have as to where we should go next. Of course, we don't just prioritize based on, okay, if enough people have asked for something, we do it. It still has to be the underlying mission that was set when the founders started the company five years ago. I think that doesn't change. Uh, so we wouldn't. just trying to think of an example of, of something we would not do. Like we would not, Okay, I'll, So sometimes when I'm talking to a prospect, they'll say, I have a blog. So what I'd like to do is have, have the Substack and I just want my Substack post to be a frame within my existing blog.

Would you guys build that? Can you guys do that? So the question of is that technically possible? Of course, yeah. Yeah, it would. It would be technically possible, but it's not what we're going to do. It works much better for subs. You have everything as a self-contained unit on your Substack. That is where you collect the email addresses.

That is where your posts live. And the reason for that is the entire raison detra of a subst stack is to have some things behind the pay wall, and the whole system works much better with the ability to send out emails and have a post on the same place. Have a, a free preview of a paid post. Have lots of subscribe buttons you're dropping. It works much better. If it is all on the one place, it's, this is not, Some people will think, Oh, that's just self-interested. Substack wants to, to drive all the, the traffic to themselves. It really just does work better, and we never sought to be a tool that would fit into WordPress. There were many, many tools that fit into WordPress that's a crowded market.

We were trying to solve a problem that hadn't been solved before. So that's an example of where, that's feedback that I've gotten more than once. But hopefully I can give the same answer I've just provided here and some people will say, Okay. I love WordPress. That's not for me. I'm gonna stick with what I've got.

I'm not too concerned. The other thing is there's an interaction where the writers and the people who use Subst Stack are the best advertisement for it as well. So they are often making posts about, Well, this is why I prefer, like one writer wrote a post and he said, I wish everybody would just come on subs. Because he was, he's a, he was a blogger for a long time. He said, Most bloggers don't realize how much better it is when the whole experience is centered around capturing the email address. It's, it's much better to have that front and center and always be urging people to get the email, because once you're in the email inbox, it's.

It's very intimate. Uh, they never miss a post from you, and it's way better than having a blog that just has a enter your email here, box over on the side. So a post like that, I'll save that post. I'll send that to people who are thinking about it and say, Way more than me who works there just trying to sell them on it.

It somebody who's actually walked the path and has, uh, had the experience of being a writer and developing an audience and choosing the best tool, which is an important decision. They're, they have decided that it's better and they, they make the argument why they think it's better. So I'd say, yeah, but just go, to go back to your original question, I would say that we are always gathering information from what, what users wanna see.

And that heavily, heavily, it has heavily shaped the roadmap over the past year. If you look at the fact that our podcasting features have gotten just miles better than they used to be, that's heavily related to what people have been asking us for, for example.

[00:34:01] Ben Parry: That makes, that makes total sense. So it's kind of, uh, you know, the mission never changes, but the, uh, ways of articulating that mission, both in terms of how you talk to people about it and in terms of the product itself is in this kind of constant, uh, feedback loop, uh, that makes

[00:34:20] Linda Lebrun: Well, the mission of Substack is create a better future for writers by letting them achieve financial independence by publishing and having a direct relationship with the reader. That what I just said, that that won't change and can't change, but how we actually affect that, uh, It looks very different today than it did five years ago, but that, that kernel of that reason for subst existing, uh, remains.

So it's very easy for me to tell people. For example, if I'm talking to someone and they say, Well, I have my email list. I'm never going to have. Paid content on my email list. What I use it for is just to market my merchandise line and I sell swag and that's how I make money. But I know I'm never going to, to, to turn on paid on the newsletter itself.

It's, it's just to, to market the swag. I know for sure that I can say to them, Substack is not the right place for you. You, you know, we, you wanna be technical and don't have product market fit. If you wanna just be practical there, you should probably be on MailChimp. MailChimp is really optimized for e-commerce subs stack.

Because of what I said about what the mission is, it would make sense for us to. Optimized for eCommerce. Might we build eCommerce features at some point? If enough writers want it could be, yeah, maybe. But it will never be optimized for that because it's always optimized for the independence of writers, uh, you know, being on their own, building a platform on their own online.

[00:35:40] Ben Parry: Makes lot of sense. So, I have one last question a little bit. Maybe this doesn't go anywhere, but you have a, uh, Twitter account where you're very active lInda@substack, I've really enjoyed in preparation for this, uh, interview going into your Tweet replies, uh, and seeing you in interact with, a bunch of people.

I, I saw for instance though, when, uh, you seem to be trying to convince, uh, Visa for a long time to get onto the Substack.

[00:36:14] Linda Lebrun: Oh, you dug back into the archives. Wow, you scrolled. Yes. I, And he has one, by the way, but I just don't think he's posting actively on it. I just, of course he'd be wonderfully as this huge following. He's wonderful writer.

[00:36:26] Ben Parry: Yeah, I, Well, I, so I was gonna ask, cause I know he has one now. If you, if you know, if you were the reason he fi uh, he finally got convinced to sign

[00:36:34] Linda Lebrun: I am not the reason for anything that happens. People decide whether they want to do it a Substack. I think that he knew, Look, he is on Twitter. He's highly connected. He knew that subst existed. Sometimes go back to the being an evangelist thing. Sometimes the, the role of the evangelist might just to be that person who says, You know, I think it would work for you if you did this, because I've seen other people like you for whom it has worked.

That might be the piece that's missing because people might not know, Oh, you know, I'm, I think I might wanna do a Substack about golf, but I don't think there are any Substacks about golf. So it probably won't work. Well, I could probably say, here are three Substacks about golf. Or if there isn't one, I would say you have the chance to be a category creator.

Here are some other people who were the first ones who right about something. And by being the innovator, they succeeded. So I think a lot of the time is just to, to say to people, You know, you're coming. A punitive authority and I can say, Well, I work there and I, I think it would work for you. That works better if you're being honest and sincere.

You can't just say to everybody, it'll work for you and that, you know, you're gonna get the reputation as a blow hard. But if you, if it's somebody like visa and I can a visa con and I can actually say, Given your, your personal style, your writing background, I mean, it would, it would be a slam dunk. So a good use of Twitter can be to, uh, encourage people to, to DM people or just to, to also to be there where if somebody has a question, they could feel like, Hey, that's somebody who's approachable. Uh, and think platforms like Twitter, Facebook, they don't really have people that you can reach out to. So as, as a, as a startup, that should be something where we can develop an advantage.

[00:38:14] Ben Parry: Yeah, absolutely. And it is, I think it is. It provides a personality for the company in a way that a company like Facebook can't, You know, even if, uh, actually, I guess I take that back. I think that companies like Shopify and Stripe have managed manage this surprisingly well. Uh, but there's a certain, you know, that first, uh, wave of kind of like the Facebooks, the Twitters of the world.

They never, they never quite got it. But it's, no, it is amazing. But what I wanted to ask you is this, uh, this Twitter seems pretty optimized around Substack. You've got linda@substack is your name. You've got all of the tweets seem to be at Subst. Um, do you, did you have, or do you have, uh, a Twitter account that you, uh, used prior to this one?

Uh, and if so, uh, what was that like? What did you use Twitter for?

I'm just interested.

[00:39:07] Linda Lebrun: I've always had a number of Twitter accounts. I enjoy Twitter. If you look at my Twitter, you can tell it's not somebody who their first day using Twitter was when they made that account. So, I have a number of accounts which I won't disclose on this, uh, a podcast partly because I really feel like everybody has the right to have an online life that is, aside from their work. And, this is a controversial idea now, okay, somebody, some wa uh, equipped that we are the first generation who can be fired for something we do on the weekend. It's at the point now where any utterance of anybody, if it has their real name attached, is considered to be a formal statement of whatever corporate body they're employed by, which I think is nuts.

People should be able to have a, a private life. So, and also we, all of us have many identities. You may have your. Account where you talk to your friends, you may have your account where you talk about your political views that some of your friends might not totally agree with, so you, you don't necessarily wanna bother them with it, et cetera.

So I for sure, I love social media. Look, I've been posting online since php, BBB bulletin board days. Anybody who's listening, who's over 40, that's gonna ring a bell. But I would say, Gen X age people. My age people were the, were the, the the last people who remember a time before the internet and then a time with the internet.

I think millennials that, most millennials, they had like a Facebook page when they were very, very young, or they had an email address very young. But I think that Gen X is the people who, like we were still unfolding a paper map when we were teenagers and then, Uh, um, you know, we segued into this world of everything being online.

For some are cynical about it and feel like something was lost, although there's others like me who think that it's a huge innovation, very helpful, uh, alleviated a lot of inconvenience from the world and opened up audiences to people. So that might sound like super pollyanna, but that is how I, how I feel about it.

[00:41:02] Ben Parry: I, I couldn't agree more. Uh, and so that's, uh, that's wonderful to hear. Um, but thank you

[00:41:11] Linda Lebrun: Thank you Ben

[00:41:13] Ben Parry: I mean, I, I feel very lucky. I feel really, really lucky that, uh, you, uh, would, you know, give this time and, um, it's been, it's been a real pleasure to speak with you.

[00:41:24] Linda Lebrun: Let me, because I would be remiss not to end with a plug. So anybody listening, if you wanna start a Substack, just go to subst.com, click on create Your Substack. It's very easy. You don't need to talk to me to do it. You don't need anybody's permission. And you can start posting. And Ben has himself has a Substack too.

Say the URL of your subs.

[00:41:46] Ben Parry: It's Ben Parry dot Substack dot com.

[00:41:48] Linda Lebrun: easy to remember. So join us. Join the Fun on Substack, please. I thought was my little commercial, sponsorship that I wanted to finish off with.

Thank you

[00:42:00] Ben Parry: so much,

Thank

[00:42:00] Linda Lebrun: you Ben.