(funky music) - Hey hey! Welcome to another episode of
Marketing Against the Grain, your show for marketing-minded
people everywhere. I'm your host, Kipp
Bodnar, CMO at HubSpot. I'm joined as always by my
co-host Kieren Flanagan, the CMO over at Zapier. And we have a very, very special guest. Today we are joined by Lenny Rachitsky, and Lenny is the host of Lenny's Podcast. He is the author of Lenny's Newsletter. He is one of the foremost
experts on product and growth in the world, to me at least. I love his content. We've been wanting to have
Lenny for a long time. Lenny, I'm so excited
to have you on the show. - Thanks for having me. Quite the intro, really appreciate it. - You deserve that kind of an intro. Are you serious? (Lenny laughs) You've got one of the top
business podcasts in the world, you've got this incredible
newsletter, and you've built on some amazing experience in
product and growth and are now taking that out to the world
and teaching everybody. So we're excited to have you
here with us today, and I know there's a bunch of places we want to go. Kieren, I wanna kick it over to you so that you can kind of kick things off in our discussion today. - Lenny, you have an
incredible background. I know we've talked before
and you may wanna give the audience some context of, you know, your kind of journey in
tech, or at least at Airbnb. The thing we'd really love to start on is in relation to that, what, if anything, has been different
or the same about growing like a content audience, an audience for content mediums, and that you manage to bring
some of those learnings from Airbnb into what you're doing today. Like I'm really interested in
how this stuff that you used to do translates to what you do today. - I think what's most interesting is it's very few things translate. (all laugh) - That's interesting. - Yeah, so, I led supply growth at Airbnb for a long time, and then I led the team that helped the booking experience, help you book on Airbnb. So I'm basically optimizing conversion, and so I spent a lot of time on growth. But interestingly, what I found
with the newsletter and with the podcast, is nothing
helps it grow other than just consistency and quality of content. - Mm-hm. No hacks? - No. Like, once in a while there's
a couple spikes here and there, but there's no, nothing like sustainable
helps to grow other than just consistently putting out good stuff. Like, I was just gonna
say, I tried referrals, I tried paid ads, I tried guest posts, and those helped early on. There's a few things that helped early on just kind of get it kick-started. But if you just look at like
the trend line of growth, nothing makes a dent other
than just keeping at it and keeping the quality bar high. - Can I say one thing that I do think from my own perspective, being like a consumer of
your content and so, okay. You, you know, obviously one thing that helps is that you are in that space, and you are very well regarded
within that space, where it does help you get the kind of
people onto your podcast and maybe get people, you know,
interacting with your content. But the thing that I think
stuck out in terms of your content early on was how
you included these kind of mini case studies, right? You just put out a post on
inflection points, and it's all real world stories and
it's case studies like, but they're miniature case studies. It's not like this like 24 page case study on how Facebook did this. It's like these kind of quick
hits of all of the things that companies did around a singular topic. So do you kind of agree that helped to differentiate you, and if so, was that on purpose or you kind
of just stumbled upon that? Like was that a very thoughtful, like, "I'm gonna try this as an
experiment," or just like, "I'm gonna do this because I wanna do it." - So with questions like that, I think if Seinfeld has this
funny thing that people ask him, like people are
like, "Hey Jerry Seinfeld, why don't you like do
other types of comedy? Like why'd you like, how'd you narrate it on
this thing that you do?" And he's like, "This is
all I know how to do. (Kieran and Kipp laugh) Like if I could do other things, I would do other things." And so with that post and a lot of posts, like if I had the answer, I'd
be like, "Here's the answer, I've got it," but I just don't. And so it comes out of like, I just want to get you
the best possible answer, when I do research and ask people that actually know what they're doing. Where it actually started. The first time I did that, I left Airbnb, I was there a long time, people kept asking me all these
questions about how to build a marketplace company and I was like, "Well here's like what Airbnb did, but I don't know if
that's the way to do it." Maybe there's other things
that could have worked. Maybe there's things we did that worked in spite of ourselves. And so what I did is I embarked on this big research project, I just talked to all
the biggest marketplace companies and see what they
did, and see if there's any patterns that emerge across
all marketplace companies. And that turned into this
five part series of how to kickstart and scale marketplace business. And that did really well. So, I kinda learned
from that experience of, "Man, this is a really
good way of doing it, I'm just kind of doing primary
research on behalf of people, and it's like very low cost for them." And I spent all this time doing the work and I could see why it's valuable. Because I've done a
lot of work for people. - That's what I wanna get into. Like, one of the things you said is like keeping the
quality bar high, right? And I think Kieran, you
and I, in doing this show, we've learned that
stories, examples, data, and more importantly, just
to what you were saying, Lenny, research matters so much. It's like, oh, you have
this unique perspective and insight that has real depth to it. That's what really resonates with people. But somehow, Lenny,
you do that constantly. And (chuckles) that's what I
don't understand, is like you, between the newsletter and the podcast, you have this like unending flow of it. And as somebody who's doing it right now, it's very hard and it takes a lot of time. Like how are you pulling it off? - The secret is lots of hard
work and many hours of work. One of the advantages I have is, unlike you two, you have
full-time jobs, I don't. - This is true. - So there's this kind of like
cool flywheel that kicks in once you get to a point where
you could do this full-time is you just have a lot more
time than anyone else. And I find a really direct
correlation between the amount of time I put into something and
the success of that piece. So the secret is just putting in time, and the things that you find useful, usually the person spent more
time on that than somebody else that tried to do that,
and not nearly as well. - Well while I agree with
you on the time part, the other part of that is like, what you pick to spend that time on. Because like there are a lot of people who put a lot of time in and pick bad stuff. That doesn't resonate with people. So I'd like like to hear
how you pick the stuff. - The way I picked the stuff, and I didn't think about it this way, but it ended up being really powerful, is I started the newsletter
as an advice column, like a Dear Abbey type thing
where people send me questions and I answer their question. And what turns out is smart about that, is that that content is
rooted in a real problem somebody actually has,
not just me pontificating on something that may be a thing. So that helps a lot, is just
like rooting your work on like "What does somebody actually need?" And that kind of comes back to, I think one of the most important parts
of writing and content, is there's like a job to be done
that you need to nail better than somebody else. So if you think about newsletters, what are the jobs to be done? There's like, "Entertain me." So there's a lot of newsletters
and podcasts of just like fun stuff and humor and jokes and comics. Another job to be done
is help them make money. There's a lot of newsletters
that help you invest in Bitcoin timing and stuff like that. There's a job to be done of just, "Help me be better in life." So there's like Emily Oster, and like, just like practical advice stuff. Another job to be done
which I'm in is just, "I wanna be better at work." And so, what are ways I can
help you be better at work? For me it's like, help you build better product, grow product. There's other, you know,
there's all kinds of work. So there's like a lot of opportunities, like help salespeople
be better salespeople, help engineers be better engineers. So there's a lot of
like niches within that. But I think it's really important
you figure out what's the job you're doing for someone,
and then just do that better than anyone else that's
doing it out there. And the key there is
just putting in the time. - Which does speak to your
background in product, right? Like you approached
everything from, you know, a job to be done, a problem to be solved. - Maybe, yeah. - I was gonna say that you said there wasn't that much transferrable. That is definitely a pure rip
out of the product here world. - Okay, there's one, we got one. - The thing I'm obsessed by is like, for people who have like
reached your kind of success, like how much of it is
like very thoughtful, because when you were in Airbnb, I assume like part of leading
the grow team is hypothesis, iteration, test and experiment, trying to find the thing, and
like how much of a creator success is stumbling upon the thing, versus like being very intentful
about that is the thing. And it sounds like maybe
it's part and part, like you did go through a process
when you were like, "Okay, well here are the jobs to be done. Here's one that I can
solve and I can solve it. I feel I can solve it in a better way." But then there's like a
little bit of stumbling, and hopefully this is gonna be
the thing that resonates. - Yeah, so to be clear,
I wasn't actually like, "What are the jobs to be done and what job can I do for people," that's like looking back I
could see why it worked out. It was 90% stumbling,
and more specifically, so I left Airbnb, I had this plan of like, "Maybe I'll start a," I
was there for seven years. I worked like, intense hours. It was just like a go go
go culture for a long time. And I was just like, "Man,
I'm gonna just take a break." And my plan was, "Let me
start a company again. Maybe let me explore some ideas I had. Maybe do advising on the side as a thing, maybe join a company just like, here's some options I'm
thinking about," and the thing I stuck to is, "Let
me pay attention to what gives me energy in this phase,
and do more of that." And just like lean into
that when I get energy from something, like I have
a meeting with someone, did I get energy from
that or did that suck? And if something sapped me of
energy, I did less of that. That was kind of my rule. And I just found that writing
gave me energy, and so I spent more time doing that, and the
startup stuff didn't and other things, and advising didn't. And I was just like doing advising calls. Like "I don't want, this is
stopping me of all my energy." So most of it was just leaning into what was giving me energy. And then I had this conversation
with a friend about, "Hey, I thought I wanted to start a company, but I'm doing this
writing thing on the side. What the hell am I doing writing? There's no future here." And my wife's like, "Why are you writing? There's no future in writing." (all laugh) You know, she had published some books, like there's nothing, nothing comes of this on the internet, writing on the internet. - Feel like you're just wasting
your time then, come on. - She's like, "I thought you wanted to-" - "Get a real job." - Exactly. But this friend had a great point. Like, "You enjoy doing this. People seem to value it, which is super rare, that you
do a thing that people value and want to keep reading. That's like very rare." And his advice was "Don't
take that for granted." Like, maybe see where that goes, even if there's no future
there, just double down on that. Maybe it'll lead somewhere. And so that's what pulled me down that road is just like, this is working. Maybe just explore it. And so I just kind of kept
doing that, and ended up continuing to grow mostly
by just continuing to do it. So it was a lot of stumbling. Like I hadn't written much on the internet before I started down this path. - Well, and you came from
a product background, which there is some writing,
but it's not like... - Right, not public writing. - Yeah, it's not like, you're not writing every day as a product leader. And so, clearly that
was something that like resonated with you as a
way to spend your time. I mean Kieran and I have talked
about this on a past episode with Tiki Bush where it's like, it is the best way to organize your thoughts and learn
something, is to write. - That's exactly what started
me like, yeah, I just wanted, like the reason I wrote
the first thing I wrote, which ended up doing shockingly well, which helped me to keep motivated, is I just wanted to remember
what I learned at Airbnb. So my first thing that I wrote was like, what seven years at Airbnb taught me about building a company. Just 'cause I was thinking I'd
start a company and I'm like, "Okay, I don't wanna relearn everything. What the hell did I actually learn? Let me just sit down and write this down." And that's exactly,
like there's this quote I'm sure you've heard of just like, "I don't know what I think
until I've written it down." And I fully feel it. (all chuckle) - Yeah, when people are talking to me, like, it's interesting, right? Because I'm going through onboarding, like employee onboarding for my first time in a long, long time. And when I'm in a meeting and
like learning about things and people are talking to me, I kind of like somewhat understand it, but I actually need to write
it out in some sort of like strategic memo or a two pager, and then I kind of internalize
it and it makes sense to me. And I think it's an
incredible skill that people underestimate that, you know, no matter what discipline
you do within the company, writing is such like an
intrinsic part of how you communicate in today's world, especially when we're
gravitating much more towards remote work. Like actually writing is how
you communicate anything within the company, and it's a
real skill to be learned. So I think I agree. Like I think it's a great way to internalize your learnings. - Yeah, I think a lot of people look at a, like that post you mentioned
about growth inflections. Like, I imagine many people
think I already have the answer as I start writing. Like, "Here's the answer to what causes an inflection growth." But it's the opposite. I start just like dumping
thoughts into a doc, getting quotes, talking
to people, and that forms the conclusion, like that
comes after I start writing. The writing helps me get
there versus I come into it thinking, "Here's the answer!" - Yeah, like the magic of it is like, the summarization and the framing. It's like, "Oh, I know that I
want to answer this question, but I don't know what the
most important parts are." Maybe I've got 10 really important things, but I know that there are three that are like the most important. I need to figure those out. And like that's the blend of the art and science of that. And so I kind of get
the natural progression of how you got to writing, and the ritual of the
newsletter and getting there kind of recurring. How the hell did you like then say, "Hey, you know what I wanna
do, I wanna do a podcast. That's even harder. It's even harder to
get out into the world. I've gotta, it has way more logistics. It's not just me sitting
in a room writing, I've gotta like have all
of these conversations and scheduling and everything." Like, why? - So, I may not feel like
this on the outside, but I'm trying to like keep
it chill and not do a lot. So I've had these like things
I should do, write a book, start a podcast, run a
course, and I've always like, "I will never do any of these." I just, like the newsletter
life is really good. Like I just write an awesome
email once a week and I make a meaningful income, like much
more than I made at Airbnb. And so I'm like, "Why
would I do anything more? This is great," but- - Sounds awesome to me! (laughs) - (chuckles) It's pretty sweet. (all laugh) And so I've avoided all
those things for a long time. But with the podcast, I did
Harry Stebbings' podcast 20VC at one point, and at the end
of the recording he's like, "Lenny, you idiot, you
should be doing a podcast. You're good at this,
you have things to say. There's a lot of
opportunity in podcasting." He's like, "You should do a podcast." So that's actually what
got me over the hump. Like, Harry Stebbings telling
me "You should do a podcast." And it was like years and
years of me just like, "No, I will never do a podcast. There's so many podcasts, what the hell would I add to it?" And then I just started trying it. And I just started doing it,
actually turns out it's a lot easier than the newsletter to be honest. I have a- - Oh really? How so? - So the newsletter, like the simple way to think
about it with the newsletter, I have to come up with unique
interesting insights and write them out and craft them
in a consumable way. The podcast I just, I extract that from someone else's brain, like you guys are doing here. (chuckles) And so like, you know, it
takes like maybe three, four hours per episode
of prep and recording, and I have a producer that helps edit it. The newsletter takes like
10 hours minimum per post. Some 20, some 100. - Wow. - It's also, podcast is easier. It's more lucrative it turns out, and it's a little more
energizing, you know, this is like fun and
it's like the end of it you feel kind of cool. You did this whole thing. - You get to see humans. (chuckles) - But I will say, the podcast, like a lot of stuff I did turns out to be smart looking back, it's easier to grow the
podcast with the newsletter. Every episode I share with my audience, which is large now. So I think the right order is, build an awesome newsletter
and then launch a podcast. It's harder, I think,
the other way around. - Yeah, podcast is a great add-on to engage existing audience. It is definitely a hard
like front door to build, which is like first way
to build that medium. Hopefully it's not too bad jumping around. Like one thing I'm really
curious about, just coming back to newsletter just
for for one moment is, and it kind of ties really
nicely to your latest post if anyone wants to go read
that, on inflection points. Like I'm curious like how
quickly you got to the inflection point where you were like, "Oh, like this could be a business," right? Because one of the things you mentioned is perseverance, right? And perseverance is a really
underrated skill because everyone's looking like, I started off looking for the hacks. It was like, well if
anyone can gimme the hacks, Lenny can gimme the hacks because like, he has growth principles
baked into the work he does. And it was like, no. Like consistency and perseverance. And so how long did you
have to have that kind of perseverance for until you saw some sort of inflection
point where like, "Wow, like I could actually tell my wife this could be a business, right?" Like, I'm actually doing
something real here. - Actually when I started the newsletter, I actually called it Project
Avoid Getting a Real Job. (all laugh) And that was the goal, like,
can I make enough money? Can I make more salary than
I made in salary at Airbnb? That was like initially actually the goal was can I make 100K a year? 'Cause that's like wow, holy shit, 100K for my writing a thing once a week. And then I set that goal to 300K and then it's gone far beyond that. So there is actually a couple hacks, I wouldn't call 'em hacks, but that have led to some inflections. So early on, the way I got my, say, first 100 subscribers is, I wrote like a popular thing on
Medium, and that got me some followers on Medium, and that
turned into Twitter followers and I started tweeting nuggets
from that post on Twitter, and that started building
a Twitter audience. So there's kind of like
flywheel of Twitter and Medium. So that got me about
about 100 subscribers. And this is like one of the examples of, I wouldn't call it a hack, but it led to a spurt, is
doing guest posts on other newsletters with the same audience. So for me, I got the next 1000 subscribers by doing a guest post on
the First Round Review, and also Andrew Chen's blog. And so those helped a lot. That was just me getting started,
and the key there was like I had interesting things to say, and they wanted to share
it, so that was the key. So it comes back to quality again. So that got me to the
first 1000 subscribers. Then to get to the next 10,000
was just writing every week for nine months, just keeping at it. And it's just, if you
look at the growth chart, it's just linear growth
through those nine months. So then I was about 10,000
subscribers and that's when Covid hit and I was making no money for a year. Airbnb stock was like dead, (all laugh) which I was- - "I'd like some money
now, please!" (laughs) - Yeah, like I assumed I could do this because I had some savings in Airbnb stock that one day would IPO, and
it was not looking good. They had to like, take this
massive $2 billion loan and it was just like, travel was
gonna not happen again maybe. So I got really worried. And so that's when I actually
launched the paid plan. I was like, "Okay, Project
Avoid Getting a Real Job, Let's do this for real. Let's see if I can make money doing this." And so I launched the
paid plan about eight, nine months after I started writing. And it did like okay initially, but basically just doing
that for another year, two years every week helped
it continue to grow and kept growing, growing across 300K. So then the actual next big
inflection came actually fairly recently where SubStack launched this feature where you can
refer other newsletters, you can recommend other newsletters, which seems like a really
simple, no big deal feature. But it turns out a lot of newsletters are recommending my newsletter. So when you sign up for my newsletter, you get recommended 10 newsletters that I love, and I picked them. And so there's this like really cool network effect that's happening now. So about 1000 other newsletters
recommend my newsletter. And so as soon as they
launch that feature, I just have this like
hockey stick of growth that's happening, and
it's still happening. And I think I'm in the
onboarding flow when you sign up because I'm the number one
business newsletter you kind of get recommended my newsletter. So, there's never been an easier time to grow large newsletter,
because of that one feature. If you write awesome stuff
and people recommend you, you can grow really quickly now. - I remember back in the day, the problem to solve for their
audience was distribution because newsletters
somewhat like podcasts, or most of the newsletters, and Kipp and I talked to all
of the big newsletters when we went through the kind of research phase of trying to find the hustle. Like they're predominantly
all paid advertising in some respects, because there's no like one built in core
mechanism to like grow those. And so they really did nail
that it sounds like, SubStack. Do those thousand newsletters
get any type of affiliate commission for recommended you, like- - Nope. - They just do it organically? - Yeah. It's just like, what do
you think is awesome? And yeah, it's just like, what do you think is
great for people to read, and it feels nice to
recommend great stuff. That's it, yeah. You know, I tried referrals
and it doesn't work. Like, I think for some
newsletter it would work, obviously Morning Brew
and stuff like that. But I think it has to be a certain personality of a newsletter
for it to be like, "Send this to all your friends,
get a hat, get stickers." You know, it's a different- - Well it needs to be more, you know, higher altitude versus
the depth that you go to in your newsletter, right? - Right. - Because the thing I
was gonna ask actually, and you kind of maybe
answered it with SubStack, and I'm interested what both of you think is, if you were going to go down that original path and you started a company, the thing you were gonna have
to really think about and most founders do, is like defensibility. Like how is this like thing defensible? How about not to be commoditized? And what's interesting content is the feedback loops are really quick. Like Kipp and I talk about
this, where you see someone has figured out like threads on
Twitter and then like everyone does threads on Twitter, right? Or someone figures out like
shitposting is a thing and then everyone is shitposting, right? And so everyone can replicate
things much faster 'cause the barrier to entry is much lower. And I was gonna ask you like as a founder of a content brand, like how do you think about defensibility, but maybe your defensibility as, well, I've got inserted into
the SubStack, you know, framework, and so it's gonna
be really hard for anyone to replicate that. - On the one hand, I don't
really think about that. I think if you just keep providing
valuable stuff to people, they're going to keep wanting it. So I think the question is, will someone come around
that does much better than I at the same thing. Like I'm not that smart. (Kipp and Kieran laugh) People have more time,
they have more experience. It could definitely happen, 100%, but I will say I don't like, I don't know why it
hasn't happened, honestly. I have found a lot of people are modeling their newsletters now after my newsletter. Like I see welcome emails
just like completely copied my welcome emails. (Kipp and Kieran laugh) There's a lot of like, advice
column style newsletters. Exactly like I, like
the intros are the same. So there's a lot of, like you know, it's the sincerest form of flattery, people modeling the approach. No one's come like right at
exactly what I'm doing yet. I wouldn't be surprised if it happened. Obviously I have a headstart, I don't think about it too much, but it could definitely happen. I don't think there's
much of a moat, you know. - Let's talk about that though
because I think your moat is, you know, the grind that
you've done obviously, but then it's also like
that quality of content, like that taste and knowledge which you have on the core subject area. And you've talked about
a lot on the show so far, but I guess I'd love to, you know, take a trip inside your head
like what are the questions you ask yourself to know if something is meeting your bar, that it's like, it's really great and like
this is gonna be something that is valuable in the world, and
gonna be more valuable than anybody else could do this week. And subsequently like,
"I feel great about it." - Like, I wish I had like a formula of like, "Here's what I look for." A lot of it comes down
to, I just look at it again and again and again. Like, most of my writing is just editing. I start with just like a bunch
of content and writing and bullet points, and then
I form it into something, and then I just look at it like a hundred times
as I keep reviewing and editing, I email it to myself, I look at it on my phone, and
I basically get to a point where I just feel like, this
is strong enough and there's nothing I can cut and
there's nothing that's just like consistently confusing me. And that's kind of the core of it. I just look at it a thousand
times and keep looking and looking and looking, and what can I cut? There's this really influential
book on my writing, book that's been really
influential in my writing, called On Writing Well. - Oh yeah, Darmesh loves that book too. - Basically it's just, cut everything. Is the conclusion just
cut, cut, cut, cut, cut. (Kipp and Kieran laugh) And it's like a hundred chapters on all the things you should cut. So that actually had a big impact on me and I just kind of look for that, like, what is not necessary
and then how do I just tighten and simplify and bullet point
it and charts and table it. So that's the core of it. Like, you know, I try to find like ways to engage
people in the beginning, like make it a surprise
or make it interesting or story at the beginning. That's what I'm trying
to work on a little bit, is like actual writing writing, not just, here's content information, but mostly it's just
looking at a thousand times, and that comes back to the time. Like I just have the time to do that and I think that's what makes it better. - Yeah, so really your
bar of quality is like, "Oh, I have a feedback loop of topics that people want because of the
format I'm doing this thing in," I'm in, have a research process that I go and validate that topic through through my own first-party research talking to people. And then you're like, I
try to be a ruthless editor and break that down and
make it the best, clearest, most simple distillation of that solution. Like I remember having a
college journalism professor, he was like, "Go through
and underline every just, and every very, and then
cross them all out." (laughs) You know, like, get rid
of like all these things that don't do anything. And you're saying like that's a really important part of just getting the idea as tight as possible. - Yeah, so let's look at the example of that growth inflections
post, which was super recent. So the question there was, what causes an inflection in growth? And what I do with those is,
I think about what are the companies I would love to get insights from and stories of like
what helped them grow? So the way I start there
is just make a list. Here's the companies I would
love to capture stories from, and then I just go email people that I know at these companies. And what's cool, another
flywheel that kicks in with this is the more of this I do, the more connections I've built, the more companies I'm close with. So I just kind of email these
people, and I try not to bug 'em too much, but often people are excited to, you know, contribute. So I just sent an email, "Here's my question, what can you share?" And then I just capture all those and see what comes out of it. That's roughly the approach. - I think that is like, understated in how powerful it is. Like there's a, you and I
talked about this, right? I brought it up in the last podcast Kipp, there's a Twitter handle where
there's a sales community and they tweet like real stats
from that sales community. And that sales community, it's anonymous, so I don't actually know, 'cause they do tweet things that you can't really share
as a public company. (all laugh) But whatever, but whatever. It's really like, but it's anonymized and it's aggregated, right? But being able to get like, you know, the look behind the scenes, there's kind of two ways I
think about your content. First of all, like you
described it, like I'm learning, like when you're putting a case together, like you're the curious learner that's kind of learning on their behalf. And you're framing it up in
a really like interesting way and then you're actually able to help take people behind the scenes. Like they feel like an insider, right? "Oh, like I'm an insider. I get all of the kind of hot stuff." If you actually pay for
your pay subscription, you're kinda like the insider now. And I know you actually have a huge community as well, as part of that. And so I think there's like
something in that like that there's like, core things that
really make that content much more powerful than the
just the average post you're gonna actually read. - Even more, basically like I'm just doing a lot of work for people that
would cost a lot of money. (all laugh) - Yeah, people like that. - I'm just creating a
crap ton of value guys. It's not that hard. - Yeah, I'm just spending tens of hours, answering a question for
you and it's like not that expensive to get the answer. - Well, building on that though, like that makes total
sense for the newsletter. But it's very different when you're doing the podcast, right? Like, 'cause you're having
this realtime interaction, you're trying to pull
the right things out. You don't control what the
other person's going to say. So like, you know, what
does Lenny know today that he didn't know when
he started the podcast about how to actually do those things really well, like get the
best information from people? - So one I've just like upgraded the look of the podcast, like, I look back at my first
episodes I was just like so frumpy and funny looking, (Kipp and Kieran laugh) like very basic look. So there's a look of it. I think mostly it's just working on the interview techniques and continuing to follow
up on questions where someone has a really vague
answer is a big part of it. Same with the newsletter. Like, I just tried to get
to like real concrete stuff. Not just like, "Here's a general theory
I have on something." - Keep diving. - Just keep diving, and then I can cut stuff that doesn't work. So that's a big part of it. Part of it is just vetting guests a little bit better. Like, you know, some guests come on and they don't actually
know as much as you think. And so trying to get to
that a little bit earlier. Mostly it's, and then also, I don't know, it's all the interview technique,
is kind of what I find. Just like not having to like
respond to every answer someone gives and just like
onto the next question. Onto the next question. People don't want you to
be like, "Awesome, great. That was so interesting." (all laugh) - No they don't. - Let's do something else. It's like fun, you know, it's a balance. So it's a lot of interview, and
I try to watch my interviews and try to like see what's
annoying and dumb most- - Yeah, we do the same thing. It's painful to watch yourself that much. - It's so painful, I hate it. (Kipp and Lenny talk over each other) It's the downside of starting a podcast. You have to like listen
to yourself all the time. - Kieran, did you just say you loved it? - Oh, I can't get enough of myself (Kipp laughs) (Lenny and Kieran talk over each other) I watch myself on my
big screen, the AI Wars. I'm like, "Oh look I'm on YouTube, with all these other people." (laughs) - I mean, to a Lenny's point, if I had a dope sweater
like you're wearing. YouTubers hate your sweater. If you like, or hate- - [Kieran] It's not this one. You're getting confused. - The sweater, comment on
YouTube right now. (laughs) - But hey, I would love to actually hear how you vet guests because that could be kind of like, you don't like bring them up for initial conversation and say- - I don't. - "No, no I'm not bringing you back (laughs) 'cause you suck." Like, you just vet them up
front without them knowing? - I'm trying to rely more on referrals from other guests that
I've had that are awesome. So that helps a lot. And then watching their other
talks and videos helps a lot. Just like, what have they got to say? That kind of thing. But you know, you never know until you actually talk to someone. - Are there some interviews
you just don't use? - Not yet, not yet. Everything's been good enough. - So you have a community,
you have a podcast. Let's say you had infinite
time and infinite resources, or you just had the motivation to do it. What is the other thing
you would like to do? Like as a creator that you're not doing? Like what's the thing
that you think would, when you apply that energy would
make you feel the same sort of ways you do about
newsletter or podcast? - This would make me feel in the same way, but I think I would do a book, is the- - I think you have to do a book man. - Yeah, but it's so painful. (laughs) It's so much work. - It's so much work. Especially on the topic you're
gonna do it on, and how much information you already have put in it. But you gotta do it. We all want it. - [Lenny] One day. - You gotta give the
people what they want. - (laughs) I guess. I think they'll all get smarter and it'll be better the longer I wait. That's how I tell myself. - (laughs) Can I say
that about everything? (Lenny laughs) Is that a new procrastination hack that I can use for my own life? - Yes, take it. - But seriously what's the
hold up in doing in a book? - Just the workload that it's gonna, my wife actually has
published a couple books, and I see the process. It's so hard. It's just like, you know, it's like a year of intense work. You don't make much from it, you know, maybe 0.1% of people make some from it. It's just the workload. Like, life's good, you know, like I talked about the newsletter, (Kipp and Kieran laugh) like why would I want to bash my head against the wall for a year? But I think I'll probably
do it at some point, I just, I don't think it's time yet. - Why can't you do a book that's just a collection of the newsletters? - That's what, I think- - All us dorks would love to just like have on the
shelf behind us, you know? - Tim Ferriss did that, right. - I think though, that's
the mistake people make. They think it's gonna be that
easy if they have a bunch of content and they're just like, "Oh, let's throw it together." But it never is. If you wanna make it awesome, like I have a high bar and I'm very detail-oriented about this stuff, so I just wanna make it super awesome, and it would just suck up my life. - Yeah, okay, so I gotta ask you my favorite question for
detail-oriented people. It's like, how. do you know when to stop? Like how do you know, like you're editing that newsletter
and you were just like pounding your head against the wall. Like how do you know like,
"Okay, we're good here, I'm gonna stop and move
on to the next one." - I think very concretely, it's when I don't find
anything else to tweak when I look at it. So I look at it, I'm like,
"Okay, let's fix this, fix that," and then come back to it later in the day. Look at it, okay, maybe there's the title, I
can make it a little better. And when I find that there's
just nothing I'm changing, that tells me it's ready to go. And you know, could always be better. But you know, I'm publishing once a week and people aren't paying me like 100 thousand dollars,
like, 150 bucks a year. Like it's not gonna be
perfect, perfect forever. But it's mostly when I'm
not changing something. That's the sign to me. - Follow up to that is like, you've worked really hard
to build all this stuff and you were like, "Yeah this Operation Not Start a Business, and you kind of now
ended up with a business- - Getting a real job. - You're making stuff, but what are the unintended positive
consequences of all this? Like what are the really good things that have happened that you're like, "I didn't expect this but
like my life is way better because of like doing this creating." - I also wanna share the downsides 'cause I think people don't think about that, but there's like so many
upsides like angel investing, it's so much easier. - That's what I was
hoping you'd talk about. - Yeah, like most founders would love to have me involved in helping. So that helps a lot. And so I get just like access to a lot of cool founders and companies. That's one thing. And the other is, you know, I just get things like, at
least once a day if it's just someone saying really nice
things about how much the stuff I've done has helped them. So that's always nice. And then just meeting, I think meeting a lot of really
amazing people through the community, through the
founders that I talk to. Like the network has gotten
really big and interesting. On the downsides, I have
no time off, you know, no PTO, no one's gonna
pay me to take time off. No 401K matching, no health insurance. Like I just have to go
Obamacare, no disability. You know, if I like get injured, I don't know what happens. Like you just, you know, stop. - Yeah, if you can't type,
well that's concerning, right? You're like, "I don't know
if I can go skiing guys. I need my arms." - So I worry about that a little bit. Hasn't been a problem yet. - Like one of the great things, but I always say like where
everyone really wants to end up, even when people talk about like, I wanna semi-retire or retire, it's like I just don't wanna be answerable to someone else's schedule. Like I actually wanna dictate my own time and own my own calendar. And I think there's, obviously
you still have to work, you know, a certain amount of hours a week to do the work that you do. Like you control your own time. And there's just something
I think magical about like, being answerable to your own calendar and not being answerable
to someone else's calendar. - 100%, that part is amazing. There's this book that you probably read, The Subtle Art of Not Giving a Fuck, and he talks about how like
people think they want just freedom from everything, but it turns out, we
still wanna solve problems and do interesting things. So I actually thought I'd, I was like, I was trying to try to
mini-retire a little bit. I was like, I'll just
do the simplest thing just to make enough money
and that'll be great. But like, at this point I
have full-time job hours, I work a lot, and it's hard to resist I think for folks like us. Like we just don't wanna
sit around and just, you know, check Twitter
all day and watch TV. (Kieran laughs) - Well we don't want the brain to fade. You know, we wanna go and do something that helps people, right? - You just wanna do
interesting things and yeah. We'll end up finding work for ourselves. That's kinda what I've done. I just keep finding like the podcast, like I don't wanna do a
podcast, I don't need more work. But it's hard to resist 'cause
it's just like there's a big opportunity and it's interesting and people are keep asking you for it so. - Well and it's also collaborative. You get to meet a lot of really
awesome people that maybe you don't talk to as much if you're just heads down writing, right? So it's probably a different kind of modality of working too, right? - There is another downside
of the creator life is like, it's kind of, you're alone. Like at least in the newsletter life, and it's kind of fun to work on a team. The other downside I forgot
to mention is there's like, people think they're gonna
create this like viral TikTok video or some amazing post or
some amazing podcast, and it's just gonna go blow up and
the life will be so great. But you realize that's
just like one thing, one time, and then it
fades and you're done. No one cares about it again,
like a few days later. And you realize it's this never
ending treadmill where you consistently have to keep
putting stuff out forever. Like, I don't know how I
even get off this treadmill. (all laugh) - I don't either. - Like, a podcast you can stop, 'cause it's app based I'm guessing, like the newsletter subscription and people are paying for the next year, every day there's an annual
plan being bought every day. So at least for a year
I have to keep it going. But like, stopping it sounds really scary 'cause then I lose the income. So I don't really know the exit path for something like this. I don't think about it too much. (all laugh) But that is one downside is
like, you think it's like, "Cool, I'm gonna get a viral video, it's gonna be so great," but you have to keep
doing that for a long time and it gets less fun. So I will say a lesson there is, make sure if you go down this path, work on something that
really is interesting to you, that you're curious about, that you really care about,
versus creating this job for yourself that sucks. Where you're like writing about, I don't know, Bitcoin all
day and you're just like, "I don't care about this stuff." (all laugh) - Trying to scam people. - Those are terrible work
examples, Bitcoin, it's great. - It is interesting, right? Like we talked about this in
an episode before about the creator, for very few creators
the exit will be some sort of sale, because they are the brand. Like Mr. Beast, you know
apparently got offered a billion dollars for his YouTube channel, and I suspect you can maybe say, "Oh, maybe he can like get himself out of being on the brand." Like, Mr. Beast is a brand
but it's not his face. Although it's still very hard to imagine. But that's one thing for creators, is like they are the brand. And you have to like, I think you have to be explicit over time. If you want to make that into
a brand that's not you front and center, or like they'll
always be the brand, but I'm not sure then what my exit is. - Maybe don't call it Lenny's Newsletter if you wanna do that. (all laugh) - Or you're gonna have to
just sell it to another Lenny. There's one Lenny out there. They love this stuff. (Lenny and Kieran talk over each other) - Oh, the Lenny's newsletter. I mean it's you also underscore the importance that name doesn't matter, the content matters. - [Lenny] That's right. - Which, everybody spends like six months coming up for a name. Finding the perfect name for something, or the perfect domain name, and that does not matter. What you hit matters is like, hey, no, find something you like, have a process, and grind it out. - Grind it out. - Like, yeah the name came from, I was just signing up for a
SubStack, and their default recommendation when you're
signing up as like your first name newsletter, 'cause I
had no plan with this thing. So I'm like, oh, Lenny's newsletter. (all laugh) - That's hilarious. That's a great story. As as we're closing things out, one last question from me, and then Kieran if you
have anything jump in. It's like if somebody is
listening to this and they've been on the sidelines and
they're like, "You know, I've been thinking about
a newsletter, podcast, like kind of, that's what
gives me energy not my job." Like what would you tell them
to try to persuade them that it's a worthy thing for them
to do, or to tell them, "No, you don't wanna do that
because it's just gonna be a complete miserable grind." - This is gonna sound obvious, but honestly it's just, do it. Stop thinking about it. Just like write a thing,
and see what you think. See if you enjoy it,
see if people value it. That's the more important part. And like I will say writing
is like, I don't know, Hemingway never said this probably, but people attribute it to
him, that "Writing is easy. You just sit at the keyboard and bleed," (Kipp and Kieran laugh) and that's how it feels a lot of times. And so it's not gonna be easy easy, but just like, that's all you have to do. Just like SubStack, you sign up, it's free, you write a thing, you could put it out there. Nobody's gonna remember if it sucks. All you need to do is
just like write the thing, write that something that you
want to get outta your head. Write something you're trying
to remember or crystallize and just see how it feels. Is this cool? Do people care about what you're writing? And part of it is just realizing, do I enjoy this and do
I wanna keep doing this? And you only know if you start doing it. So yeah, it's like such cliche advice, but I think it's just like,
it's so easy to write. You're not gonna record
a video, that's harder. Just like write a thing, see how it goes. - The thing I really took away as well, is if you look at Japan, 10 year olds, there's a higher percentage
of 10 year olds in Japan that wanna be a YouTuber than anything else. Like, everyone wants the creator life. But really your kind of points are, it's really the
perseverance and the grind. Like everything is a grind, it's just a grind that you choose. And the other, I think lesson that's really important for people to take away is, what makes great writers great is not what they put on the page, it's what they take off the page, right? Like that editing is
like so, so important. And I think that's a really
great takeaway for everyone. - And I think to add to
that, like introductions, everyone always such long introductions, like just skip the intro
and just get right to it. That's something that I've learned also. - I Love it. This was a great conversation Lenny, I know you are busy and you're taking time away from your own creating to come and and and help us create. So thank you first and foremost. - [Lenny] Absolutely. - And everybody should go subscribe to Lenny's pod and Lenny's Newsletter. And the last thing I wanted to ask you before we jumped off is, like, who else's writing do you love? Like what are the other
newsletters you're reading? Like, what else would you
have people take a look at? - I always feel worried
not mentioning everyone that's awesome. But anyway- - Well, I'll limit you to three. You just have to name three, and if they don't make it, it's okay. Whatever you think. - Noah Smith, he's got a
newsletter called No Opinions, which I just learned so
much from reading his stuff. He's on SubStack, he's actually like right
below me in the rankings. So it's like counterproductive
to recommend him, (Kipp and Kieran laugh) but he's that good. And then Emily Oster, like family, kid stuff is always great. I don't know if y'all know
her but she writes incredible stuff on kids stuff. So that one is awesome. And she is on SubStack also. And then Tyler Cohen is the other one that comes to mind immediately. He's got this podcast called
Conversation with Tyler. He's got a blog called Marginal Revolution I think it's called. And I always just learn so much
every time I hear him talk. And he's an amazing interviewer too. - Love that. I'm gonna go check out Tyler 'cause I'm always looking to
be a better interviewer. Speaking of that though,
Lenny, thank you so much. We really deeply appreciate you coming on Marketing
Against the Grain today. Thank you so much for your time and we'll talk to you again real soon. (funky music) - This data is wrong every freaking time. - Have you heard of HubSpot? HubSpot is a CRM platform where everything is fully integrated. - Whoa, I can see the client's
whole history, calls, support tickets, emails, and here's
a task from three days ago I totally missed. - [Announcer] HubSpot, grow better.
