Modern writing is very different from sitting in a reclusive
cabin in the woods secretly toiling away for years to write
the next best seller. Modern writers write in public in front
of and with their eager readers. My guest today, Dickie Bush has
helped 1000s of people start writing online. And he does this
with such kindness and the love for teaching that I just had to
talk to him about all things writing. We'll dive into
Ship30for30, building a media business and why his mom has
been such a wonderful and pivotal figure on his
professional journey. This episode is sponsored by
acquire.com. More on that later. Now, here is Dickie.
Hey, Dickie, thanks so much for being on the show today. You've
taken one of the most solitary acts, that's writing and you've
turned it into a team sport with Ship30for30. Where did that idea
come from?
Man, so we're right on the three year anniversary. We're coming
up probably a week away from the original tweet that started the
entire Ship30for30 journey, so excited to dig into that. But
first, I just want to thank you for having me. I was sharing
before this that I think that your positivity and energy that
you bring to the X Twitter timeline is something that the
world needs a lot more of. So I just wanted to make sure that we
shared that because
I've been listening to this podcast, you hear your voice and
Thank you!
just the way you bring founder's on and talk to them. And it's so
positive some what you do across the board. So just wanted to
make a point on that before we dive into all the stuff that
we're going to talk about today.
Thank you.
Okay, so anyway, on the Ship 30 side, we're about three years
since that original tweet were backing up before Ship 30
started. I was working a full time job on Wall Street as a
hedge fund trader, graduated college. I immediately started
working, it's the only full time job I ever had. I quickly saw
the writing on the wall about nine months into that job that I
did not want to be commuting to the subway at 6am sitting under
fluorescent lights for 14 hours a day leaving when the sun was
down and repeating that every day and hoping that one day I
maybe made enough money to be happy. I saw that writing on the
wall and said okay, I'm not going to quit immediately. I'm
going to start writing on the internet. This was January of
2020. And for the first nine months, I followed that
conventional path that I think a lot of people fall into when
they start writing, which is start a blog, write on that
blog, hope that readers find you someday. If your writing is good
enough people will find you etcetera, etcetera and nine
months in, I had 150 newsletter subscribers, maybe 200 Twitter
followers. And I was like, this is not what I was hoping. I'm
still working this corporate job. I have no potential new
opportunity because of this. So I was ready to give up entirely
on it. But rather than stop, I said, I'm gonna give this one
more shot. But instead of writing on a blog, I'm going to
write a daily Twitter thread every single day for 30 days.
And instead of publishing on a blog, I'm going to put it out in
social where other people might be able to find it. I wrote for
27 days. And on the 28th day I hit publish on a Twitter thread
that got zero likes zero comments and zero retweets. So I
said, well, here I am, back stuck again at square one, looks
like this challenge failed. And I'm probably done with this
writing on the internet thing. I'm gonna go explore some other
opportunities, but I wasn't wanna quit. So day 29 I ended up
hitting publish on something that I didn't think was gonna go
anywhere only for the sake of getting to my last 30 days, hit
publish, turned my computer off, went to bed, woke up the next
day, it went viral. Eval had retweeted it. Balaji had
retweeted it. A bunch of people that I really looked up to had
four or 5000 likes. I went from 200 followers to 1000 overnight.
I like to say it took nine months to get to 200 followers
and 12 hours to get to 1000. And everything compounded from
there. So I tell that full story because you mentioned that it
was a very solitude activity, right. And that exactly is how I
felt on that 30 Day Challenge. It was very lonely. I'd started
to meet some other people but realized, okay, if I want to
continue doing this, I'm going to need a community of
accountability and support to keep me going. So I tweeted out
after that 30 Day Challenge and said who would be interested in
an accountability group where everyone writes and publishes an
atomic essay every day for 30 days. And I retweet that tweet
all the time. I comment about it because it's all chronicled on
the timeline of when it started. And that was the original vision
for. It was just getting people together because writing online
typically is pretty boring and lonely if you don't have other
people doing it with you. So that was the origin and the last
three years has been kind of a wild journey of trying to get as
many people as possible to recognize all the upside that I
unlocked from my personal 30 day journey and getting them to
experience the same thing.
Yeah, oh, I bet that. That must have been quite the day when you
got the viral moment and that kickstarted all of this
community building and teaching that you've been doing until
now. That is so cool. I was there too. I was still watching
it. I remember this. I remember like the early days. And when
Ship 30 happened. I was like, what's going on here? Like,
somebody is actually trying to turn this into something that is
not just for him but for others, like you've been teaching
others. I do wonder like, how did the first cohort when you
started out, when you experimented. How does it differ
to what you're doing now?
Oh, it's nine-day difference. So the very first one, it's so
funny because so much of this story comes from that first
cohort where I tweeted out this tight form and said, who'd be
interested and I had like three or 400 responses to that. And I
was only I only had a couple 100 Twitter followers at the time.
So I'm like, oh, my goodness, yeah. Because like other people
picked up on it. And there was clearly a need here. So rather
than let everyone in, I said, okay, we need some kind of
buffer in some way to make a little bit of accountability.
But at the time, I had never made a single dollar writing on
the internet. I was terrified to charge anything because I didn't
think I had any kind of credibility. So to create that
little bit of friction, I said, okay, to join, it's $50. And
I'll give you your money back if you write every day for 30 days.
So everyone who came in, put $50 into a PayPal pot and I said,
I'll donate the rest, whatever we end up because I was like, so
terrified to charge money for this thing. And I'm like
managing a spreadsheet during the cohort, like who's written
every day and people at the end are like I wrote every day. Can
I get my money back and all this, and I'm managing it. And
really, that original cohort was just a accountability group. I
didn't have any credibility to teach writing. I did one thing
well. I could build a daily writing habit. And all I did was
prove that I could have done that for the 30 days prior. Now,
how things are different now is after that cohort, which was
November of 2020, I met Nicolas Cole. And he had written at the
time The Art and Business of Online Writing. And I was still
working for BlackRock. I partnered with him in January of
2021 to basically take his education and his way, much
Richard Denser experience running on the internet than I
had, packaged it into a 30 day curriculum and then delivered
that as part of Ship 30. So the last three years has been, it's
a community power courses, how we say it core base course
committee power course, where we teach the fundamentals of
digital writing based on his book and you have the
accountability of hundreds of other people who actually are
writing with you. And you have the structured output goal of
writing every single day. So the original cohort was a spamming
essays and a Slack channel with no structure and it was $50. And
you get your money back. And today, it's, you know, 500 to
1000 people join every single cohort. We've helped almost
10,000 people start since then. So it's been quite a journey
since that original managing of a spreadsheet journey.
That is so cool. It's an amazing story, obviously, like as a
narrative of how something that just started out with you
figuring out oh, yeah, there might be some people out there.
And then it turned into this community driven thing, which I
love. It's such a nice thing. As a writer myself, like, I feel
like the best feedback comes just from writing and getting
people reading it and telling you what they think. And if that
happens in an organized structure, which a community is
and a cohort is that just makes you so much less afraid to
write. Right? Like, I wonder what are the common things? Or
maybe not even the common things. What are the uncommon
things that keep people from writing? Because accountability
happens when you already started writing, right? But what keeps
people from writing to begin with?
One of the beautiful things of Ship 30, is you and it goes with
the name of this podcast, we kind of bootstrap your initial
audience, where you have other people in the community, not
necessarily that are going to be that interested in your writing,
but you're going to find one or two or three people who do
really want to read whatever it is you're writing about. And
that people overestimate how many people they need to read
their writing to go and iterate and improve on it. Where in the
beginning, one of the thing that holds them back is they think
they need this massive audience if they're going to do anything
so they say, you know, I have all these great ideas, but I'm
actually not going to publish them until I have more followers
because then I'll unveil my good stuff. And what happens is they
don't write any of their good stuff, which means the handful
of people that do see what they have to say aren't impressed. So
they never get to start spinning that feedback loop. Where
instead we say, look, you only need two or three people.
Because imagine you were in a coffee shop. And you started to
read your writing aloud and two people next to you were like,
hey, I'm really interested in this. Can you tell me more? And
you go, no, no, no, I don't want to hear your opinion. I need
like 1000s of people if I'm going to go publish any of this.
It's like, no, you would just have that conversation with
those one or two people and you'd be over the moon excited
that they had anything that they were interested in any way in
what you had to say. And that's kind of what we emphasize with
writing is you don't need a big audience to start. You just need
one or two people who are going to say, hey, can you talk a
little bit more about that? And then you talk about that thing
next day. And then they read that and you talk about their
next questions, the next questions and before you know
it, the scale of the internet guarantees that if one or two
people are interested in your writing, the algorithms are
going to work overtime to take what you have to say and show it
to as many of those people as possible. And so that's what you
get to tap into.
That's a very interesting observation, like the seed
audience doesn't need to be massive. I hope that's still
true in a couple of months on Twitter because the algorithm
seems to be a bit problematic in terms of discovery from any
things, right? Is that something that should impact your writing,
like writing for discoverability not just by people, but also by
the algorithms that amplify the things that we have to say?
Well, yes, because the algorithms aren't going
anywhere, which means you do have to figure out how to put
things in a packaged way that the reader is interested in.
Where people go wrong with algorithms is they blame them
for something. It's like, oh, the algorithm is blank. The
algorithm is the same for everyone. Which means, and I
kind of internalized this idea is one of my core beliefs, but
anything that every circumstance I come across as an opportunity.
Which means if the algorithm is the same for everyone else, I'm
going to look at it and say, well, what's working about it?
That doesn't necessarily mean you become a slave to the
algorithm, where you only end up publishing like Google Chrome
hacks that go viral. But you do have to understand that we live
in an algorithmic feed age, which means there's far less and
this is something we've been learning, right? So a lot of
people might end up in my situation with a couple 100,000
Twitter followers and say, oh, I've done all this work. And now
the algorithms changed and I'm screwed and I'm gonna go
complain about it. Whereas I said, oh, great. I've been
writing for the last three years. And it sounds like and
feels like my interpretation of the algorithm changes that your
level of followers matters far less than it ever has. And
they're following more of a TikTok style algorithm where you
never know where your writing is going to go. Which means every
single piece of writing has far more upside than it ever has
because you don't know what's gonna happen to it. What's the
solution there, publish more pieces of writing to unlock that
upside. So I went on a podcast like two months ago and someone
said, how are you reacting to this algorithm change? I'm like,
I'm just going to post way more, right?
Right
Like, that's the solution because what is that going to
do? It's going to give me more data. It's gonna give me more
information on what's working. And I've had more success over
the last couple of months on Twitter because of that. Whereas
other people I heard complaining and they're like, oh, you can't
do XYZ. It's nope, that's an advantage for me. I'm going to
go publish more. And I'm going to figure out what's working
because of that.
Yeah. And that's the big difference, right? Like figuring
out how new things work in a new way. You need to kind of fall on
your face a couple times. And I think you have this concept of
micro failures. That's what you call it, right? The idea, well
do explain it, I guess this is probably a good opportunity to
I love Twitter as an idea refinery, which means the second
I come up with something that I might find interesting or I want
to explore more, I put it in a note in every Sunday for the
last three years, I've sat down and cleared that note into
individual tweets. It's like my favorite part of the week
because I end up with eight or nine ideas like, I'll really
listen to our podcast interview and pick up on one or two things
that you say that I want to go deeper on. And I've been testing
ideas for the last three years on my Twitter account. Some of
those have gone viral. Some of those were not my best writing
and they went nowhere. And because of that, I now have a
pretty good idea of what people are interested in, what I like
to talk about. All the while, all these proven data points
from my old writing are compounding for me that I can
then repurpose. But then I also have all the new ideas that I'm
putting out that, hey, I didn't know that if I talked about this
topic, people are actually really interested, cool. I'll go
double down on it. So rather than 500 years ago, if you were
I don't know how long ago, but if you wanted to publish a book,
you had to go write the full thing and slave away in a cabin
in the woods for multiple years and hope that you emerged with a
best seller. And if you didn't, too bad, you wasted 10 years of
your life. Now you have an idea, you can tweet it out into an
algorithm that's going to show it to a lot of interested
people. And they're going to give you that instant feedback.
So that's kind of the digital writing versus legacy writing
approach that we talked about in Ship 30, which is you now have
access to rapid fire feedback loops for all of your ideas such
that you have no excuse now to invest a lot of time writing
just introduce that idea, right?
something that the market has not already validated that
they're interested in. You look at a lot of the successful
writers right now like Morgan Housel, Shane Parrish, Polina
Marinova. A lot of these writers who are coming out with a lot of
successful books have proven these ideas on their Twitter
account for years.
Yup
And of course, people are going to buy it because they built up
credibility and they've validated those ideas over the
last decade.
That's a genius idea. And that's the concept I guess what you've
also been doing and I think I've been doing with like building in
public, like the idea of sharing things, everything in public and
seeing where resonance happens, right? Because resonance is the
validation that you're talking about.
Exactly! We talked about, there's two types of content.
There's reach content and resonance content. Reach content
is the nine books that will blow your mind about X thing where
those go viral. And it actually doesn't matter who writes it
because you don't even look at who wrote it, you just look at
the content. And so there's no resonance with the writer versus
when you write a story and share some lessons or you build in
public and share your journey so far, the reader gets to the
bottom of that and goes, wow, that was valuable writing and
I'm glad I read it. But now I feel more affinity towards this
person. And that is what you're going for with testing ideas, as
well as you want to figure out what ideas can I share that if I
can sprinkle on my personal story, people are going to then
say I just like reading you, not only for your ideas, but because
I like following along.
Yeah, for the longest time, I've had a lot of trouble with the
concept and the validity, I guess, of this reach content
that you're talking about. Because to me, I had this mental
limitation. So let's call it a self imposed limitation here,
that all content aimed at reaching more people that is
kind of supposed to go viral is bad content. I was like really
and even like a couple months ago against like this kind of
virality seeking because it feels to me often that the
concepts and the formulas you apply for that or to that kind
of content to make it have reach, harms often or can harm
your existing audience that is already there. Because what I
thought was, well, if I write to get new people interested in me,
it kind of doesn't serve the other people that are already
there. Right? Whereas if I write for the people that are already
there, it might also attract new people. How can you help me
overcome this limitation? Because I know that writing
stuff to attract more people is good because it will attract
more people to the things I have to say.
I'll give you two frameworks that I think about a lot for
this type of content. First is my general content raiser right
now, which is how I decide whether or not I publish
something is I want to create content that only I can create,
that I also would enjoy to consume. Now, that might mean
there are some pieces I put out that are more on the reach side
that I then have to figure out well, how can I make this
valuable? Do I care about seven Google Chrome extensions that
will 10x my productivity? No. So I'm not going to publish those.
But will I potentially look at, like I publish something today
about Gary Halbert's writing tips. And it was something I
proven in the past that has gone viral and people enjoy it. I
make sure to put my own personal spin on it of my interpretation
and how I'm using his principles. So it's only content
that I could create. And I make sure before I hit publish on
anything, would my former self have found this valuable? Then
you can dial up the size of the question. So we talked about the
size of the question dictates the size of the audience. So
something like how to be happier, how to make more money
is going to be a lot bigger than how to grow your niche podcast
from 2k to 10k downloads, right? So if you look at potential
things that you could share that would widen your top of funnel
is really the right word for it or people just to find you. And
then keep your resonance content of like sharing the more
actionable stuff that you're working on on a daily basis. The
hard part to get over. And I still struggle with this is I
think we overestimate how much of our content all of our
followers see.
Right
So when you say something like, I don't necessarily want to
publish this because it's so top of funnel that my readers who
are already reading me aren't going to get more value out of
it. I think we sit there and think we're kind of the center
of the universe. And it's like every single thing I publish.
And my fun story about this is when I wrote my newsletter for
those first, like 35-40 weeks, I had like a couple 100
subscribers. And I remember going out of my way multiple
times, like heavily inconveniencing myself to
publish on a Sunday because I wanted to keep my streak and I
just felt like, there's these 200-300 people and if I don't
publish, like, oh, no, they're never going to read me again.
And they're like, waiting, refreshing their browsers at
like, 10am waiting for me. And so one Sunday, I could not get
back to my computer and I didn't publish it. I was like, oh, no,
like it's over. I'm gonna have 50 emails in my inbox being
like, I can't believe that I've been reading you for all this
time you didn't publish. And I finally got back to my computer
on Monday and I opened up my email and there were zero people
who messaged me like, hey, where's the newsletter? And I
remember that all the time because I think we overestimate
our relative importance. And most people have so much going
on. They're way too busy thinking about themselves to be
like, oh, he's writing in a different way. And I'm not
finding you know, I think that'd be my like small, top fluff
piece of advice because I feel that all the time still.
Oh, me too. I actually had that last week as well. Similarly, I
integrated I think that the ConvertKit sponsor network into
my newsletter because I started working with them for you know,
ads and sponsorships on the newsletter itself. And I was so
afraid to send out that email with the first kind of
programmatically generated ads because I never had that in
there. I always just had like sponsors that reached out to me.
I helped them with copy put it in, but now it's just a little
fragment and they insert ads that fit the person that the
newsletter goes out to. And I was like, I'm probably gonna get
like, I have 20,000 subscribers on the newsletter and I'm
probably gonna get 10,000 emails about people complaining and
massive unsubscribes because people don't want ads or
whatever, zero, zero people.
Isn't it crazy how we can build up these stories in our head and
they just have zero evidence to back them, but can dictate so
many of our actions? I think about that all the time. It's
not an easy problem to solve. But at least we can start to
inch closer from a self awareness perspective, when
those biases start to present themselves.
I think having a conversation like this where two people who
do this reality still share this. It's like impostor
syndrome, which we all have in many different ways and
different intensities. I think that's important. And I think
it's also and just kind of what I tried to hint at with the
whole solitude solitary thing of writing. The creator life is a
fairly kind of encapsulated, isolated life, right? A lot of
the things we do happen in here and they barely leave our head
before we turn it into the shape in which we want to deliver the
thing. So, you know, there's a lot of involuntary feedback
mechanisms and feedback cycles in the brain that we probably
shouldn't have running most of the time.
Yeah. And so I agree, having a couple people that you can
stress test the absurdity of some of these beliefs with is
very powerful. Like, I'm lucky to have my co founder, Cole,
right? I sit down, I'm like, oh, it's all over. I'm freaking out
about this. He's like, no, that's just not gonna happen,
like and then all you need one person to tell you that that
idea kind of doesn't make any sense. And you get out of your
head, you're like, oh, yeah, you're right. Okay, thanks. On
to the next thing.
Yeah, yeah, you do get stuck with this. I'm fortunate to have
a partner. My girlfriend, she's amazing with this. She just
pulls me back out. And she has this kind of bird's eye
perspective on what I'm doing. You know, I'm in the trenches.
I'm in the arena. But she gets to see like, the bigger picture.
And it's nice to have this conversation. So I guess have a
great partner, either in life or in business to help you out of
this is interesting. And that's, I guess, something new for
creators. I see this accountability group thinking
that you have like, where you find people who are on the same
journey and masterminds, you have that too, right? The idea
of having people that are your peers that are in the same kind
of stage of what you're doing and having consistent exchange
with them. I feel that's new. I don't think I've ever really
been part of these kinds of groups. And now I am and it's so
Yeah, it's also kind of a almost a side effect or kind of a
much better.
It's so much better because you recognize how difficult is it
for you to find people to have a conversation about the biggest
problems you're facing as you scale your podcasts from X to Y,
like, you can't talk to your high school friends. You can't
talk to the people that you work out at the gym with. You can't,
like the amount of context to have the conversation that you
actually need to have the number of people are so few that you
consequence of doing this in public in front of people.
have to go and intentionally find and set those groups up
yourself to make sure that you have that feedback of ideas.
Because otherwise, you just end up in that spiral where you're
playing a solo game for no reason other than you haven't
found those people. But once you find them, this game becomes so
much more fun because especially early on, like I wish I had
built more of those relationships at the beginning
Right? Not just writing in complete solitude and then
of my journey. And I have and I'm so close with some of them.
And I've gotten to grow with a handful of people throughout
kind of my creater journey. But you get that double compounding
because you're getting better, your relationship is getting
better and the other person is getting better, which means the
conversations you can have further and further down the
line, you both have more skills. So anyone's like, yeah, I feel
very lonely in this journey. It's you just intentionally
figure out how to take the same attitude positive some that you
bring to Twitter all the time. If you just bring that, you're
going to attract people at the same stage of your journey. And
publishing every now and then. But being this enigma of a
those relationships are really the main bread and butter of why
you should be creating in the first place is because as those
compound, those are the most fulfilling.
person. I think that used to be a thing for writers right? Where
you were so untouchable and you were so mysterious and it still
is but I don't think it's in the creative space particularly in
an audience driven creative space. This just doesn't work
anymore, right?
It really doesn't. And the evidence is in the people who've
had the most success. They are not spending years slaving away
over their manuscript hoping that a publisher picks it up.
It's no, I've built a newsletter to 200,000 subscribers. Here's
your seven figure book advance because of that. That's the new
game that we're playing. And so the more that you can tap into
it, you're just at a bigger advantage. And it's more
fulfilling. You get to engage with your readers the entire
time on your journey up, rather than hoping that you just
dropped this masterpiece at the end.
Yeah. And they also get to tell you if it's good or not, while
you create it. That was my experience with my second book.
Right
But it was incredibly powerful because the book that came out
I think I had, what was it like 500 beta readers, which was
of it was a different book that I intended to write. And I'm
quite an interesting group of people to wrangle, but you know,
it was a lot of feedback, let's just say that
glad for it because that's the book they needed. Right? It's
not the book I wanted. It's the book they needed, which is yet
again, a validation of necessity and problem rather than just a
solution looking for a problem.
Is this Zero to Bootstrap, what's the name of it? Can you
remind me?
The second one I wrote is called The Embedded Entrepreneur.
Right. What was the one before that?
Zero to Sold, that's my first one.
Yeah, absolutely. That is one of the biggest things I've learned
Zero to Sold. That's right. I remember and it's so funny you
say this about the beta readers because I remember watching your
over the last also like three years, just like you kind of
Twitter as you were writing it, where you would post the Ulysses
started around 2020, late 2019, like,
word count of like, knocked out this many words. Here's what I
Yup
wrote about today. And the comments were like, oh, my
goodness, can I read this chapter? And it makes sense that
when you published that book, you had voracious readers ready
to knock it down. And it was solving the right problem. So
you're the perfect example of what we call lean writing, which
is you are validating those ideas as you go just like the
Days before the world changed, right? That's kind of when I
best startups are validating their product as they go. It's
really the same thing. You're just the CEO of your writing and
that your product.
started there. So I've noticed the same thing. I've been
running software businesses before and they had their own
internal dynamics. And now that I run a media business, which is
being a writer is all about kind of, I guess, a media person.
A media product creator, it's the exact same thing. The
Yes
structure, the exact same thing. You have a product, which is
whatever it is, right? Might be a writing, might be a software
thing. It's both writing just one is for machines. The other
one is for people. And the mechanisms with which it grows
into a better product is the exact same, small iterations,
close feedback loops with the people that the iteration is
supposed to help, right? And the product in general. I've seen
the exact same thing. SaaS business, media business,
structurally exactly the same, which is funny because I wrote
Zero to Sold thinking, this is for SaaS businesses only, that's
kind of what it says, bootstrap SaaS business on the title. But
I could cut the SaaS part out and take a couple chapters about
tech stacks out there even though even these articles where
I talk about choose the tech you know. That translates to writing
just to say, right? You don't need to install Scrivener or
Ulysses or whatever. Just use word if you want to write. The
words matter, not the tools. And it's the same for software.
Yeah, just to double click on that because there's so many
people out there who are paralyzed getting started
writing because they're like, I can't write anything until my
Notion dashboard is perfectly optimized, ready for this
content flow that it's just beautifully optimized. I hit
every, no, my ideas? No, I've been using Apple notes to write
for a long time now because it's the only thing that
intentionally doesn't have anything shiny that is going to
go pull my attention away from doing the writing itself.
Yeah, that's great. Yeah, I've recently started like writing an
audio a little bit like I started just talking. Because to
me, writing is thinking and I think that it's just a different
word for that, right? A different kind of way of
thinking in a specific kind of technical term. But I started
just dictating stuff into, I use audio pen. I had Louis Pereira
on the show and I talked to him about his tool, which is just,
you know, it records you and then it kind of slightly
summarizes it using like open AI. And I use that as my
baseline outline. Then I start like, you know, filling it up.
Two things there. First, so Louis Pereira was the very first
paying customer of Ship 30 that I didn't promise their money
back to
So I still remember his name $99. And it's legendary to see
Oh, wow.
all the cool stuff that he's gone on and built. But Louis
will always hold a special place in my heart because right when
you said that, I was just brought to so many memories of
seeing that first Stripe of 99 bucks when I put it for sale
with no money back if you wrote every day for 30 days. So, so
funny you mentioned that. Shout out to Louis if he's listening.
But on top of that, yes, I find writing is the best vehicle for
thinking because you've experienced this too, as you've
been writing. Now, when people have conversations with you,
when they ask you a question, 90 plus percent of the time I would
wager that your head jumps to a topic or concept you've already
written about. And because you've already written about it,
you've thought through it clearly. And you can articulate
it better than other people who just riff off the cuff. And so
writing is really pre thinking future conversations you're
gonna have and you just are figuring it out during the
writing process.
Oh, I love that. That is such a great way to explain it. And
beyond pre thinking, which is definitely an amazing part. It's
also you have a tangible asset to give to people, right? Here
are like a week's worth of thoughts distilled into 1000s of
words on the exact thing that you just asked me about.
Yes
Enjoy, right? You lead them, which is such a wonderful thing
to be able to do. Yeah, I mean, you don't have to convince me
that writing is amazing. But I think the potential for it to
impact not just money concerns, which are important, but also
just the scope of the topics that you have consciously
confronted with your mind. And then having this kind of long
tail of like evidence of your thinking out there for people to
find that is just such a massive investment into your future.
And the key thing to keep in mind here and what keeps a lot
of people from writing in the first place is they think they
don't have anything valuable to say. And so we have them conduct
what we call the two year test, which is over the last two
years, you look back and you reflect on skills you've built,
life transitions you've made, hobbies you've started, jobs
you've started, jobs you've quit, topics you've learned,
rabbit holes you've gone down, etc. And picture for a second,
that your two years ago self got to have a conversation with
current you. Think about how valuable they would sit and talk
to you for hours, they'd ask you hundreds of questions of all the
things that you've gone on and learned. That's the same thing
that writing on the internet is. You're going to take the ideas
that have now become painfully obvious to you, but would have
been incredibly valuable to your earlier yourself two years ago
and you're going to write and share those ideas. And the
internet, again, guarantees, like we talked about earlier
that there are tons of people at that old stage of the journey
that you used to be on who would find it valuable. And that is
really the entire game that I've been playing for the last few
years is learn a topic, write about it to my former self where
in that process of writing it, I better understand it. At the
same time I build credibility with people behind me while also
learning from people ahead of me. And I've just been
continuing that path all the last three years and I intend to
for the next 50 years of my life.
Oh, I bet. Well, I'm gonna be there for those 50 years if I
physically can. But yes, that's super stringently put because we
tend to only look at the people ahead of us, right? That's the
kind of the star appeal that we just I think we're socialized
with, look at the people who are better than you so you can
learn. But the fact that you can actually teach to the people who
are behind you on the same journey, that seems to be
somewhat, you know, suppressed in terms of where we get taught
about it. But I think it's such a central part of why we should
write and why we should create
Yeah, you want a better understanding the ideas that you
thought you understood well, like if you think you understand
something, try to teach it to someone who's two years behind
you. And you quickly realize that maybe I don't and maybe I'm
not as good as I think and that writing just forces you to level
up.
Yeah. And in a funny way in doing that, you also get to a
level where you can teach to people ahead of you as well
because the thing that you create gives them a different
perspective on the thing that they also think they already
know. But they are learners, too, right? I had Aaron Francis
on the podcast just a couple of weeks ago. And he's just
screencasting and all that kind of stuff. And he knows there are
way better people that do like screencasts and videos. But his
style, his unique style is also an inspiration for them, not
just for the people who come up behind them who want to do
things like he does, but also to the people that he learned from
and he admires. I think that circular thing that in you
teaching you learn things that you can teach the people who
teach you, it's kind of a mobius band of feedback, right? This
infinite thing that just wraps around you and the people that
you care about in this interesting and multi
dimensional way.
A great example of this was in February of 2021, I kind of hit
an inflection point when I published a Twitter thread. That
was probably two months before that of 12 questions that
changed my life, 12 journal questions that I reflected on
and that was inspired by Tim Ferriss's article, the 18
questions that changed his life. I saw those and was like, wow, a
handful of these, I'm going to ask myself so I'm learning from
him. And then I was getting a haircut. And I get a text
message with a screenshot from one of my buddies. And it's a
screenshot of Tim Ferriss's five bullet Friday. And the first
item that he linked to was my Twitter thread talking about
questions that I was reflecting on and he said, adding a few of
these questions to my list really enjoyed it. And there's
the perfect example of someone that I learned at the time I've
listened to every Tim Ferriss episode. So I still remember I
was getting my hair cut. I'm like halfway through and I see
this text and I tell the barber I'm like, you got to stop and
I'm like got like half my head shaved. And I walk over and I'm
like freaking out because what do I do with all of this? I'm
getting a bunch of text now. And it starts to go viral on
Twitter. So, so funny and just a great example of yes, you learn
from the people ahead of you teach those behind you because
that's all I was doing, was saying, wow, I'm learning from
Tim. I'm behind him. But I also have a bunch of experience from
the last couple years from these questions. I need to publish
those because I feel morally obligated to the people behind
me. And then in the meantime, he got to pick up a few as well. So
it is so fun when that comes full circle.
Yeah, I'm really happy for you. That must have been a wonderful
experience. But it just shows that if you just your authentic
self and you are taking things from other people and adjusting
them and you know, making things your own and then sharing that
back, which is the big part, right? The big part is not just
keeping them to yourself, but actually sharing them back. A
lot of interesting things can happen.
Especially just one final point on that, especially in the age
of algorithmic timelines. You never know who's for you page
you're going to end up on, which means you right now could
publish something that pops up on Jeff Bezos's timeline. Never
before in human history has that been possible. So again, if you
need another reason to actually go and publish your thoughts,
there's another one.
Digital writing is the great leveler, right? The great like
equalizer in many ways. Like if what you do is good, it doesn't
really matter how well you connect it or who you know or
you know, who follows whom, like it will get to the weirdest and
most interesting opportunity spaces possible. So cool. Yeah,
I'm really happy for you and really happy for everybody who's
writing to be honest. And I'm glad that's the thing why I'm so
excited to talk to you about all this. That Ship 30 even exists
because that to me, conceptually, it has unblocked
so many people and 1000s and hopefully soon 10s of 1000s at
the same time. That is an interesting business. And I
think it's just a calling that you've fell into or that you
found, I guess, which is super cool. Beyond Ship 30, I know
you're doing a couple more things. And that's also
something that I found very interesting looking at you not
just as a writer, but as a business owner, right? As a
person running businesses, you've diversified in several
different ways. And one of the interesting things that I found
is Typeshare, that is something that you also build, which is a
software business, which is I said it earlier, it's
structurally the same as a media business, but it is technically
something different. What drove you to build that, in
particular?
So Typeshare was born, we had been writing our atomic essays
during Ship30 cohorts, like via the apple notes app or like
screenshotting, you know, your word and Sam, the founder came
to us and said, hey, I built this thing that I think your
students would love. It would allow them to publish high
quality visual atomic essays. We're like, this is great.
Absolutely. And so that was in August of 21. So a little over
two years ago, we've been building, basically, the
software version of Ship 30, which is if our mission within
Ship 30 is to help a million people start writing on the
internet, we can reach a good bit of them. But at the end of
the day, the most helpful thing for people will be to set up the
publishing and everything that could take someone who's never
written about. I use my mom is an example who's writing. She's
been a part of 20 cohorts. And I try to think, how could we have
gotten her to write with software two or three years ago.
And that's kind of the entire project vision is someone who
has some kind of ideas in their head, they open up Typeshare,
and it pulls all of those ideas out of them. So ask them
questions, it preps the page for them, it gives them templates,
it shows them analytics, it helps them write headlines, it
helps them format, it helps them do everything. Well, basically,
like you said, they could just speak like that's where we're
headed, is that the ideas in your head. The amount of
friction to go from idea that you have to publish to asset in
the real world. We're trying to minimize that time and minimize
all the friction that keeps millions of people from being
able to do that. So yeah, Typeshare is founded by Sam and
then Cole and I are co founders with that as well. And we
onboard people during Ship 30 into Typeshare and they get to
use that and then also people find Typeshare from other areas.
But a lot of fun, a lot more difficult to build a software
business as I'm sure you know, that in media business like
they're similar, but one is a lot harder. And there's a reason
why people raise money for these kinds of things because you do
need a talented team. So we've learned, we're still learning
and still growing Typeshare and figuring out what role it wants
to what role we wanted to play in kind of our overall business
portfolio. But it's been a lot of fun. A lot of lessons.
Yeah, I bet. Yeah. And software unlike people, either it works
or it doesn't, right? There's no in between. That's one of the
big problems there. And since you mentioned your mom and her
blog, it is I don't know how it feels. And I do want to ask you
how does it feel to have your mother blog on your software?
So it's funny because my mom's story. She has been pivotal to
the entire Ship 30 journey where backup to Ap, no May of 2018. So
I'm a senior in college and I'm about to graduate and I received
a phone call from her that she's been diagnosed with stage four
ovarian cancer. And that shook me pretty heavily at the time. I
ended up going home right after that emergency surgery, whole
nine yards. And that was right as I was about to go into the
real world to work at BlackRock. I took care of her for two or
three months. She was on the path to recovery. And then I
went and started working in New York, but it gutted me to be
away from her and recognized that I didn't have the freedom
if I wanted to, to go spend more time with her. Fast forward a
year and a half into 2020 when they sent us to work from home,
I got to go live back with her during that time. And she was
actually re diagnosed with a small recurrence while I was her
primary caretaker then, during 2021. During all of the Ship 30
cohorts, she was writing and that was one of her vehicles
through recovery was I could write and share my ideas and
talk about stories. She shared tons of information about how
to, you know, best care for someone dealing with cancer, how
to talk to them, how to conversations. She's recently
started a nonprofit, all based on the ideas that she's shared
and attention she's generated. So it's so fun to have her back
for every cohort. She's kind of like a mini celebrity where we
do breakout rooms at the end of every live session. And I always
get a bunch of messages from people like, oh, I got to be in
a breakout room with your mom. It was so much fun. And so she
loves being a part of it. And it's so cool to see she's
writing right now. We did a trip to Greece over the summer, which
was kind of a dream trip for her. She always wanted to go
there. And I had made that promise when she beat cancer for
the second time that we'd go to Greece. And so now, during this
cohorts Ship 30 that we're currently on, she's writing a
bunch of essays recapping our trip. So I get to read those.
It's super special and a lot of fun. And I appreciate you asking
that because she's been such a pivotal part. She was there from
that original tweet. She's supporting me every step of the
way. It's been great.
I would like to give her a massive shout out because I've
been reading all her blog posts.
Amazing.
First off, she loves you from such a deep place. It's really
incredible. That is such a, you can really feel it. I was
tearing up a couple of times during those blog posts. And I
really mean it. It was a wonderful and it felt like a
very private thing. But it was still public that I'm really
happy that she shared that and that she shares how proud she is
of you and how amazing you are as a son and as a person, as a
human being. I mean, there's a lot of stories in there about
you as a kid and all that. If I know you from Twitter, I know
your adult fully realized self but through her stories, I also
get the person into the story that taps on. Yeah and yeah, a
lot of texture and a lot of heartwarming, a lot of embrace
around it. It's really cool. And to see her and her story. And as
you said, pivotal part in all this and her pivotal part in
your story. I love this. I really, I was so happy that I
found her blog on your product. Right? It was such a perfect
storm of love and kindness all in one. It was really wonderful.
I appreciate that. And I know she's gonna love listening to
this. So shout out mom, if you're listening to this.
Thanks. This is proof that you need to keep writing. Right?
Sometimes she wakes up. She's like, oh, no one's reading this.
I'm like, you have no clue the amount of impact that your
writing has every single time, so my cheeks hurt from smiling
so much. Thanks for telling that story. And I know she's smiling
listening to this.
And you seem to be a great teacher of writing as well if
she is not also a great writer to begin with and taught you all
these things. But her part in particular, like if she's part
of Ship 30, let's just talk about her writing for a second
here.
Yeah
They're short blog posts, but they're impactful. They're
thematically focused, they're narratively rich. Texture is the
word, they add so much to just a learning like I could turn what
she wrote in a tiny little two sentence tweet and it would have
none of the richness and the feeling that comes from these
stories that you write. So you must be a great writing teacher
if that is the outcome of Ship 30, man.
I think I was born with it from her and it just took me a few
years to encapsulate it so it's been fun to have. Like I said
with Typeshare, it's like she's the best Typeshare product
critic because I just talked about like the what is it? The
Collison installs, where the Collison brothers used to sit
over their shoulder and they'd watch people like click on their
software, right? I've been doing that with her in Typeshare. I'm
like, alright, team. My mom can't find this button. That
means we got to redo this thing because if she can't find it,
that means no one else can either. So it's been fun across
the boards where she gives feedback on just about
everything, for better or worse, you know?
Well, that's the thing
For better, exactly!
Probably for better. And if it's worse then it's still better,
right? It also puts a completely new meaning to the Mom Test,
which I think Rob Fitzpatrick would really like conceptually.
Right?
Yeah, exactly.
That's wonderful. I'm really happy to hear this. And I think
that's, now you are my favorite family business now.
Oh, man! I appreciate that. That's awesome.
Well, okay, so you've Typeshare, you have Ship 30. Is there
anything else that you're currently working on that's
interesting?
We have a couple of other that we are dabbling in. So one is
our right with AI paid newsletter. So we have a paid
newsletter that we're growing right now that's $20 a month
that gives ongoing updated information on how to best turn
ChatGPT bard other AI writing assistants into your personal
intern. So that is a paid newsletter on substack that, we
find that is one type of information that is going to be
changing so rapidly, that you want to stay on the cutting edge
of it, which is why it's a paid subscription newsletter. Why?
Because you get two editions every week that's going to show
you how to stay on the cutting edge of using AI as a digital
writer. So that's been a lot of fun. We have a vision for kind
of a suite of paid newsletters, where we're getting to the point
of our business where we're interested in decentralization,
where rather than focus on one product from one type of person,
we want multiple products. So we have software, we have paid
newsletters, we have group coaching, we have cohort based
courses, we have digital courses, we have everything to
kind of build out this entire ecosystem that as you mature as
a business is really the goal. So you're not dependent on one
thing or for the first year, we sold one thing to one person and
got to a million dollars and that was Ship 30. And then as
you get to different levels, you want to expand who you market
to, who you sell to and how reliant you are on all those
people. So that's one with our paid newsletter. And then the
one that we've been giving a lot of focus is our premium ghost
writing academy. So this is a group coaching program that
helps freelance writers become premium ghost writers. We teach
them everything they need to avoid the freelance writing
hamster wheel. And we also help people who are stuck in nine to
five like I was, of escape that nine to five job using ghost
writing because of everything. There's no startup costs. You
don't need a big audience. You really don't need that much
skill. That's a very trainable skill. You don't need 1000s of
people to say yes, you need one person to give you $5,000. And
then boom, you see an entirely new world. So we're currently
building and growing that as well. So it's kind of a
portfolio of different writing businesses all through the lens
of our goal is to help people start writing online and
monetize and build a lifelong, sustainable career out of
writing on the internet.
Wow, that is quite the portfolio. And I'm really happy
to see it honestly. Because the more I talk to successful
creators and entrepreneurs like yourself, the more I see people
intentionally starting with something clearly defined and
then growing a portfolio of derisk and diversified bets in
many different ways and different kinds of products as
well. So it's really interesting to see you going from the cohort
thing, which is a pretty high presence thing, I guess.
Yeah
Into SaaS, which is a low presence, but high, you know,
brain melting stuff and high frustration, if doesn't work,
right?
High frustration is the term there.
Yeah, but wherever you have customer service, that's gotta
be a problem, where people send you emails and then going into
the special consulting and also, you know, just teaching people
in different ways that is really, really interesting to
see. That would also be an interesting topic that I would
like to hear your long term learnings from one day when it
turns into like a bigger portfolio of things.
Yeah, we've been doing that with our podcast, which is basically
Cole and I. We're sitting down twice a week, Monday and Friday.
Monday, we'd set the plan for the week. Friday, we would recap
what happened with the business. And one day, we're like, why
don't we just record this? And people loved it because we were
just like, there is no one that you can get the level of depth
and richness of insight from a group of two guys building a
portfolio of internet companies. And so we love doing that.
Because again, it goes back to this free upside. Worst case,
we're gonna record it anyway, best case people pay attention.
And now we have new product ideas. So we have a massive
problem in our business right now, which is we have too many
ideas that we want to go and execute, which is a great
problem to have that I've reframed of like, I know that
we're gonna grow forever because we have 50 low hanging fruit to
improve every single product on top of the 50 other product
ideas that we eventually have. So it's a fun game to get to sit
down and play and I'm sure you feel the same way every day.
Yeah. Oh, for sure. And it's really nice to see you like the
podcast in particular. That's so building in public. This is
literally allowing people to be a fly on the wall behind the
scenes. Like if you're not listening to this podcast, what
are you doing? It's kind of wondering, so listen to the
podcast. Where else do you want people to go and find you and
follow you along your amazing journey here?
I spend too much time on Twitter and X sets @dickiebush, right on
LinkedIn, right on Instagram on the same there. I'd say it
depends on what you're looking to do. If you are looking to
start writing on the internet, the best place to go is
startwritingonline.com. That's our free seven day email course
with everything you need to get started. If you're already
writing and you want to start writing with AI, you can go to
startwritingwithai.com. And that'll have a free email course
that will help you there. If my story about working on Wall
Street and eventually leaving kind of resonated with you, I'd
recommend exploring the world of ghost writing. So you can go to
premiumghostwritingblueprint.com. And you'll get a bunch of
information there. So those are kind of the big three. And then
Typeshare, if you're interested in, hey, I love writing and I
just want a better software platform to go and do it all.
You can go there too. So a lot there could be changed, it could
all change by the time, you know, this episode goes out
because that's just the way this all goes. So I appreciate that.
And it's been just a fun journey in it. I do I think back to when
we met, where this is really the first time, we've exchanged and
chatted. We've been kind of Twitter friends for a long time.
But it really was like that early 2019, 2020 when I watched
you write the Embedded Entrepreneur book. And I
remember seeing that. I'm like he's just doing everything that
we talked about. It's awesome. You're validating your ideas,
you're bringing the public with you. They're all ravenously
ready to read it. So I'm excited. Do you have any other
books in the works?
Oh, yeah, I'm writing my third one on building in public
probably surprisingly, but right, you know. That's where
I'm currently at. And I'm not self publishing this one. This
time, I'm going a bit bigger, which is also fine.
Oh, cool!
And it introduces me to new issues with the actual feedback
cycle because now specialists are involved and they tend not
to one people involve too much. So
Yeah
Trying to juggle that, which is going to be a whole other little
challenge for me. But yeah, I can't stop writing. I mean, I
write every week, right? For my podcasts and stuff. But I do
want to get the new one out too. Yeah, I'm excited.
Like, well, definitely keep us in the loop on how that one's
going in. Reach out to Cole too, because that's one of his
favorite topics. He has such a strong opinion on self
publishing versus going the traditional publishing route.
Like if we eventually write, I think the pinnacle book on
building a daily writing habit that we will go published or
work with a publisher or work with a book deal because the
goal would be to get it to as many people as possible that the
rest of our books, we want to publish in a niche way because
we don't want that bureaucracy and specialists to say, hey, we
own your next 10 books. It's like we're publishing one under
your name to get as many people as possible, try to play the New
York Times bestseller game, but otherwise, it's self publish all
the way.
That's an interesting observation. I feel the same
way. Like the first two I wrote were kind of Indie Hacker News
specific. But this one has the potential to just help people
generally, build whatever they want or do whatever they want in
front of an audience, right? And benefit from those. So I think
there's a lot of overlap between what we're doing because
effectively, we're just teaching people to build their own legacy
in different ways, right? I'm really happy that you shared all
these insights and all the plans with me today. I'm like, I was
already like, 99.8% excited to follow your journey. Now with
like, 157% excitement.
Amazing!
I'm super happy. I'm happy to finally get to talk to you. I'm
happy to see how all of this fits together. I'm glad we
talked about your mom because she's awesome. And I'm really
happy to see where this is going. So thank you so much for
being on the show. That was a wonderful conversation. Thanks
for all the things you shared.
Arvid, thanks so much. And again, I really appreciate just
the warmth and energy and positivity you bring to the
timeline, this podcast. It's awesome. So I'm excited to keep
listening in. And hopefully we do another one and a couple
years, we look back on this one and go, here's all the things
we've gotten done since then. Here's all the books and all the
good times we've had. So I appreciate you having me.
Well, thank you so much.
Awesome.
Boom, boom, indeed, what a guy! That's just something about a
founder who has a plan, a vision for their future. I will now
briefly thank my sponsor for this episode today: acquire.com.
Imagine this, you're a founder who's built a solid SaaS
product, you acquired customers, and all of this is generating
really consistent monthly recurring revenue. It's the
dream of every SaaS entrepreneur, right? Everybody
wants to build this company. The problem is, you're not growing
as much as you like, for whatever reason, maybe it's a
lack of focus and lack of skill or plain lack of interest and
you just feel stuck in your business. What should you do?
Well, the story that I would like to hear is that you buckled
down and you reignited that fire within and started working on
the business, not just in the business. And you did all these
things you always wanted to do. You built an audience, you do
marketing, sales and outreach and six months down the road,
you made all that money, you've tripled your revenue, and you
have now a very hyper successful business. Wouldn't it be great,
but reality is that unfortunately, it's just not
that simple. And the situation that you might be in, well it
looks different for every founder who's facing this
crossroad. But too many times, the story here ends up being one
of inaction or even stagnation until the business itself
becomes less and less valuable over time or at worst,
completely worthless. So if you find yourself here already or
you think your story is likely headed down a similar road, I
would consider just another option, a third option, that's
selling your business on acquire.com. Because
capitalizing on the value of your time today, that's a pretty
smart move that you can also make and acquire.com is free to
list. They've helped hundreds of owners already. Just take a
look, go to try.acquire.com/arvid and see
for yourself if this is the right option for you and your
business at this time. Again, just take a look, won't hurt.
Thank you for listening to The Bootstrapped Founder today. You
can find me on Twitter @arvidkahl. And you'll find my
books and my Twitter course there too. If you want to
support me and the show, which I would really appreciate, please
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That's where you want to show up. Any of this will help the
show. I really appreciate it. Thank you so much for listening.
Have a wonderful day and bye bye.