What's up, everybody? This is Cortland from IndieHackers.com, and you're listening to
the IndieHackers podcast. More people than ever are building cool stuff online and making
a lot of money in the process. And on this show, I sit down with these IndieHackers to
discuss the ideas, the opportunities, and the strategies they're taking advantage of
so the rest of us can do the same. All right, I'm here with Rob Walling, the creator of
Tiny Seed, the startup accelerator designed for bootstrappers, and the creator of MicroConf.
How's it going, Rob?
Pretty good, man. It's good to be back on the show.
We're here on Riverside recording this, where they are the primary competitors to your portfolio
company, Squadcast, who I also used and love.
I almost rejected your calendar invite and said, I'm sorry. Here's my Squadcast link.
I could have booted up my Squadcast account and recorded it with that. It's all on Stripestime,
so whatever. I'll pay for two podcasts for recording tools.
I haven't used Riverside yet, so this is a treat to be able to... Because we used to
use Zencaster for the start of the rest of us, and then it's obviously switched to Squadcast,
and so this is my first experience with Riverside.
Yeah. Well, this is it. Get a spy on the competition. Feed whatever learnings you get back to the
Squadcast, guys. What are you using for your podcast? I assume Squadcast. Are you doing
video? Are you doing...?
Doing a little bit of video, just toying with it, actually, over the past few weeks. I hired
an assistant producer named Aaron, and he's... I love it. He's got the get up and go. He's
just like, let's try this. Let's try that. I'm the old guy now. I'm like, is this really
worth the time? Is it really worth it?
It's cool, because he's spurring me on to experiment with things. Instead of just recording
audio now, since Squadcast supports video native, I've been recording the first five
to 10 minutes of an interview or a conversation in video, and then just switching to audio.
See, I like audio only, and we've had good luck with it with MicroConf already. I think
we have 300-ish videos. We went from zero subscribers a year ago to 7,500 now, and it's
been a mix of promoting to our audience, like emailing, hey, new videos up, and then just
this organic reach. I'll admit, I had always heard YouTube is the second largest search
engine compared to Google, but it didn't sink in to me, just the sheer volume of it. This
is one of those things where it's that investment, and it's asymmetric risk of like, we're going
to pay Aaron every week to create more of these, and how many clips can we get out of
it? We're going to get nothing back for probably months, and then we'll get one hit. For MicroConf,
the one that flipped us was the Jason Cohen, designing the ideal bootstrap business talk
from 2012, I believe. That got on Hacker News, and I think Patio11 tweeted it. Just a bunch
of stuff happened, and that went to tens of thousands of views overnight, and that got
a bunch of subscribers to the MicroConf channel. Once you get there, it's a signal to YouTube
that you should start ranking for other things. That's, I think, what I'm going to try with
startups for the rest of us is, when can we get to that point where we get that flip and
the channel becomes, I'm making this up. I'm just imagining there's domain authority. It's
like, there has to be channel authority in their outfit.
For sure. For sure. They've got the search engine, which is one way to be found, and
we've got the recommended videos. You end a video, they pop up other videos. This video's
on the sidebar. It's just super good for discovery, and people will just be like, that looks interesting.
Click versus a podcast player. I don't know. Podcast discovery seems really terrible. Maybe
it's a problem that no one cares about, except for podcast hosts. We wish you was easy to
discover. Yeah, me too. I think one of the cool things about YouTube is that, essentially,
even if you don't necessarily have a channel, you can go to other people's channels and
collaborate. I experimented with this last year as well. For example, I went on this
guy. His name is Will Kwon. I noticed people coming to Indie Hackers were kind of referencing,
oh yeah, I heard about you on Will Kwon's channel. I'm like, okay, I don't know who
this guy is. Let me check. Any of the couple of videos where you just mentioned Indie Hackers.
I emailed him and I was like, hey, can I come on? Maybe we'll do a collaborative video.
He just interviewed me. His video's got 25,000 views. Now, some single digit percentage of
people who sign up for Indie Hackers say, oh, it's because I saw this video on Will
Kwon's channel. You could also do the circuit on people who already have hundreds of thousands
of subscribers who talk about tangential things, sort of influencer marketing via YouTube rather
than just doing kind of the podcast circuit. Oh my gosh. You just made this whole recording
worth it for me. For years, I came up with this, it's not a terribly clever name, but
podcast tour. Because I did it for Hit Tale and I did it for Drip. It was like, I'm not
going to do a book tour. I'm going to do a podcast tour. I'd make this big list. I'd
tell everyone I knew and a bunch of people who I didn't know and I would go on every
podcast, just blanket the earth, right? Trying to talk about, again, Hit Tale, Drip, whatever,
Micro Gomph, Tiny Seed. But I had never considered, of course, it's just a simple copy paste,
like to do that on YouTube. Now, I don't have much of a network on YouTube, but that is
a really good idea.
I think it's underrated. People just don't think about, like the prototypical podcast
is an interview. And so everyone's like, oh, I should pitch myself to be interviewed. But
on this guy's channel, Will Kwon's channel, he's not doing interviews. He's making these
like highly edited, cool videos. You know, like the fact that he just snuck an interview
in there, it's like super easy content for him, super easy for me. And so yeah, I think
it's underrated. People should try it out.
I have actually purchased ads in Overcast and you can go to overcast.fm slash ads to
kind of see their rates. Yeah, it's interesting. I heard about it from Craig Hewitt, right?
Who reigns Castos and is tied into all that. I purchased ads in a couple other players,
but it didn't, it didn't work. Overcast, I saw new subscribers increase. The cost eventually
got much like AdWords and Facebook ads before them. The cost became, you know, not a cost
prohibited basically. I think originally when I did it, it was like maybe a dollar per new
podcast subscriber, which sounds outrageous, but it was still like, cool. I think it's
like four bucks per now. And it's like, I just can't, I just can't not for free.
It's not worth it unless you're making a ton of money after podcasts. You probably aren't.
I don't know very many people who are, but yeah, podcast growth is such a, it's very
different than every other channel. Like I'm starting a podcast with my buddy, Julian,
and like just thinking about podcast growth, but growth for almost any sort of app is basically
like user acquisition and like retention. Like those are the two biggest numbers that
matter. And if you're sort of leaking users and like, that's really the first thing you
need to plug. So if you imagine like a blog, like James Clear's blog, he's got a ton of
traffic to his blog. Almost all of that comes in through SEO, which means his retention
is basically zero. Like every reader probably doesn't come back, probably isn't like routinely
going to jamesclear.com. Podcasts are almost the exact opposite where all the big shows
that I'm aware of, like have an extremely high retention numbers. People just listen
because they like the hosts and they kind of want to check in with the host. And like
most of the best podcasts, if you listen to their intros, it's kind of the host is kind
of like shooting the shit with each other, just saying almost nothing. And you kind of
get into it because you're like, Oh, I like these people. You know, I want to hear what
they're up to. And so podcasts are all about retention and acquisition is much harder because
like there aren't really great channels for acquiring like listeners, like there's YouTube,
there's ads, there's kind of the podcast tour, like the best thing to do is advertise your
podcasts on other podcasts. But like, that's it. And it's really hard to measure like the
tools suck. I think Apple just now revamped like their tools right now. So you can kind
of like go in and see like really detailed metrics and stuff. But like it's been like
20 years and they're just now adding tools for you to see this kind of stuff. And so
yeah, I think it's a big opportunity for people who want to take podcasting seriously to really
dive into like the strategies and think about like what makes a show retentive. You know,
for any hackers, for example, a lot of people will get bored listening to the same stories
over and over like I've heard, you know, 35 stories of a founder succeeding, that's good
enough, you know, and so they sort of graduate. And it's like, Oh, it's not that retentive,
you know, whereas, for example, the all in podcast with Jason, Kyle Conis and Jamaat,
like that's all news. And so they'll just talk about like what's going on. And headlines
this week. And like, that's never something that you turn from, you always kind of like
want to know what's going on in the world.
And there's a trade off there too, right? Because I would never go back because I listen
to all in as well. I would never go back and listen to the old episodes because they're
out of date now. But I would if I found indie hackers, if I found startups, the rest of
us, the back catalog is amazing. So I I'm sure you get these emails, but I get the emails
or the tweets. I just went back and listened to 200 episodes of your show. And I'm always
like, I'm sorry, but but that like sucks people. And then they're like, I'm in much to your
point of they love the hosts, they want to follow the story, they want to hear your thoughts
on XYZ topic. And so that's the trade off, right?
Maybe the ideal is a combo then topical educational episodes that people are always going to find
valuable and then like some sort of like current events, news, like discussion, what you do
on your show as well, or you're talking about clubhouse and Twitter spaces that kind of
like, you know, is always relevant that people are talking about that they're going to share.
And that was a big shift about well, it was about two years ago now where my former co-host
Mike Tabor took a step back to focus on, you know, on his stuff. And I had to figure out
I don't want this to be an interview show, you know, I there are already really good
interview shows like indie hackers, and you know, there's mixture G, there's all there's
all the other ones. And I was trying to figure out that balance. And over months of experimentation,
I kept hearing the feedback. Because I was so I'm an engineer, right? And I was trying
to figure out what's the formula. And I was like, every four weeks, I'm going to do a
Q&A. And every four weeks, I'm going to do this. And every six weeks, I'm going to do
a news roundtable startup news thing. And I talked to people and they said, I don't care.
Like that's all I kept hearing is I don't care. Just don't make it the same every time.
You know, there's Rob, there's Rob solo episodes there, you know, just, and I keep coming up
with new formats. And I'm willing to try it now. Because people say the variety, the fact
that I every Tuesday morning, I open it and I don't know what to expect. I actually like
I've had no one who said, Oh, there's too much variety, or I don't know what to expect.
Or I only like this type of show, right? So that's been motivation for me to start thinking,
I had never thought of recording a solo episode before that. But now I have like these 20
minute episodes where it's just me talking, almost like I would normally have done in
a blog post, if I had more time to write it, but I'm now giving it's like, here's a mental
framework I'm thinking of, right? Or here's what I see succeeding with SAS today. Or here's
a common question, I get the same question four times in two months, I'm like, I'm going
to record a segment. That's just here's the advice I'm giving.
That's cool. How much do you prep for that? Like, do you write out basically a blog post
and then sort of read it? Or do you just kind of think about a topic and just go bullets,
just bullets. I think about a topic I make, I actually sent you kind of some outline loose
thoughts. I mean, that's about, that's even more outlined than I normally would where
it's just three bullets and I talk. And sometimes it winds up the editor edited, it comes back
and I'm like, Oof, you know, but my editor is also getting pretty good at healing. I'll
say pull that entire paragraph. You know, that, that whole story that augmented that
didn't work, but definitely getting better at it. The first time you do it is very hard
and then, you know, subsequent times you get better at it.
Yeah. Maybe I should do that. Cause it's like the, it's the least guest dependent cause
there is no guest. So you could do it whenever you want. You can always like, you know, oh,
I'm missing an episode. Just like sit down, record something. I'm curious if, is your
editor the same as your producer? You mentioned you had like a new producers, like sort of
pushing you forward. Same person.
Different two people. Yeah. I've had an, I've had the same editor for six, seven years now.
And if productized services, like, you know, cast those productions and you know, where
you can pay X a hundred dollars a month and have it done, if they had existed back when
we hired him, we would have used them. But realistically, we went to Upwork and found
someone. I do like having that tweakability. I mean, I, I probably couldn't work with productized
services because I'm just too picky. Y'all go in and be like, I'm going to slice this.
I need this whole thing rerouted. So yeah, I think the way to go is you want to like
an actual particular editor who you are on a first name basis with who knows your preferences
because then they get like, they're like a, like a, a productized service that improves
over time. You know, like they get to know you and they get to know your style, et cetera.
Whereas like, if you're using one of those companies, like you don't even know who's editing
your show and kind of give them like the same notes that you gave them last year. Cause
they switched out people. You're just like, it's not that good. So I think you will really
want to have like just one person.
It has worked for me. He is super reliable. He gets it done on time and he never takes
time off almost ever. Or when he does, he's like, I'm going to be off next week. And I'm
like, cool. I'll get you two episodes this week, which happens like once every two years.
That's the danger. If you do go with an individual is that they get sick, is that anything happens,
right? You have a single point of failure. So I do like the idea of productized services.
If you're not as picky as you and I, basically like if this was even more of a side project,
it just takes all the headache away.
I was talking to a Sam Parr, who's one of the hosts of the, my first million podcast.
And I was asking him, I was like, Hey, what did you get your, uh, intro music for your
show? It's great. It kind of sounds like an actual song where it's like most podcasts,
like we pull it off like these, uh, royalty free, you know, music sites and they all kind
of sound the same. And he's like, I don't know. To be honest, I don't even know what
it sounds like. I'm like, well, if you listen to your show, he's like, never like what he's
like, not a single time have I ever gone back and listen to a single episode of my show.
And they're like a hundred and something episodes end, which is crazy. I can't imagine doing
that, but I'm also jealous of the freedom that he has to just crank out episodes and
just not care. And the download numbers are pretty astonishing. So it's working.
Wow. Yeah. I couldn't do that because I'm too much into the iteration. I listened to
the episodes to knit pick myself and figure out how can this be better? How way, what
should I have cut? What question? I mean, all the time I'll be listened to an interview
and I'm like, why did I not ask them? This was, I'm not paying attention. Like it's so
obvious to me. I think that's probably a signal I've gotten better because I used to not be
very good interview and I think I'm getting better. And now when I go back, it's like,
oh, kind of cringe worthy naturally in conversation. I'm a very affirming person. I do a lot of
nodding. Um, you know, if, if we talk and you say stuff, I'm like, yeah, yeah, no, that
totally, yep, totally Cortland. You know, that's, I mean, you and I have had dinner,
you know how I talk. I can't do that in interviews because it's, I have to cut it all out. And
so it's almost a, an unnatural cadence of conversation because in an interview it's
distracting if I'm sitting there affirming the, the interviewee and you'll notice that
I, you and I both do this, I think now where they'll finish talking, you say nothing and
then you say the next question. So tell me about your childhood, you know, and it's,
it feels weird. Cause if, again, if we were at dinner and I did that, you'd be like, it's
not how you talk at all, but it sounds natural in an interview. Right. It's one of the things
that I've been trying to change a little bit more in my interviews, just listening to some
of the other shows that I like a lot. They're a lot more conversational. They're not interview
shows, but it's like, I kind of like the cadence and the market difference is like, there just
aren't that many questions. You know, the questions are a little bit more authentic,
but it's mostly just like two people monologuing at each other, just making statements and
then ripping off the other statement and then just ripping off that one. Yeah. The key with
that format I found is you have to have someone who is good on the mic who has experience.
Like if you get someone on and it's their first time, it's not going to work because
they're not going to bounce back and forth. They don't know how to fill air in a effective
way. Right. Cause I used to, back in the day, 500 episodes ago, I feel there and kind of
a dumb way, right? I had notes and things weren't that interesting, but you and I have
done enough episodes now, you know, just like you had been Ernst, you know, in a couple
of weeks ago, I heard that and it was like, both of you are like pros, right? And I can,
I can have Derek Rimer on. I can, you can have a Craig Hewitt from Castos, you know,
any of these folks who it can be just a back and forth. That's where you hear an all in,
right? It's like there's one or two really veteran podcasters. A couple of the other
guys don't talk that much and you can tell they're kind of, you know, pulling them along
and the show, the best podcast guest is a podcast host a hundred percent of the time
it goes well. That's that. So that's the other funny thing. Have you been invited on a show
with kind of a new interviewer, like someone who's in their first 10 or 20 episodes, a
bunch of times, the whole time you're like, I'm just going to, you know, you're, you're
like guiding them and you're, you're not actually answering the question they ask because it's
not a very good question, but you're trying to help the show be better. Yeah. Cause you
want the episodes of your own, you're on to like sound good. The hardest thing for me
is like, I don't want to go on somebody's podcast and then not tweet about it. I feel
bad. That's a shitty episode. I'm just like, I'm not going to do this. Yeah. So I have
literally inserted, I'll, I'll answer the question and then be like, and I have some
other thoughts on this tangent. Cause I know it's like, this really needs to be here,
but they're not going to ask the followup. You know, you're actually tweeting about,
I guess you said it, I'm considering creating an alphabetical index of the myriad topics
that you've discussed on your podcast over the years, which is related to what we were
talking about, how people will go through the backlog. And I've thought about this a
ton too. I'm curious what your goals are. Like why do that? What would it look like?
I was inspired by a podcast that I've listened to for several years titled money for the
rest of us. And in fact, he and I, it's really good. It's the one personal finance podcast
I still listen to. I contacted him. He started in 2014, I believe, and I contacted him and
I was like, Hey, I'm going to start up for the rest of us. And he said, sorry about the
name. I didn't realize you were already out there, but it turns out, you know, he's really
good. And I listened to it. So he's creating an index and it's almost like the index at
the back of a book where it's a alphabetical. So you go a, and it's just a bunch of topics,
you know, aardvarks and, uh, you know, sales funnels, that would be under S but whatever,
you know, you get all the, all the topics and you can click through and it has the episode.
Now, the thing I'm struggling with there, so I can have assistant producer Aaron go
do that. He could spend a few weeks and he can index it. I think I'm struggling with
this. So what does that take you to? Does it take you to the transcript and you don't
have to search? Does it take you to a certain point of the transcript? Does it try to take
you to a certain point in the audio or an audio clip? Cause that's going to be a disaster.
Right. I can't invest the time to do that. So that's where I'm kind of iffy about it
is like, would people use it? And so I did, I guess I asked online of what format would
you like to see? I didn't ask online if people would use it, but I do know that we get a
lot of searches on startups for the rest of us because we have full transcripts of everything.
So you can literally go and type in sales funnels or email marketing or the name of
a guest and you get all their episodes. So I know that that's used and I use it myself.
What I'm not sure is would people use an index, you know, but I think the idea of an index
is that you don't have to think of the search term. It's basically, you can kind of skim
through it and be like, Oh, I'd actually love to hear Rob's or guests Mike's take, you know,
on this topic. That would be the benefit. What do you think? Do you think people would
use it? I mean, would you use it? My show, just any show there are, um, there are like
some of these indexes out there. Like, you know, first round capital, they have like
searched at first round.com, which is an amazing resource. They're just like, let's take every
topic related to startups, fundraising, marketing, product design. There's like a hundred topics.
And then they're just like, let's get the best blog post on the web about that topic.
And we'll just like, you know, have all of them in a list. So you can go there at any
point in time, just like figure out anything. And it was like, that must have taken so much
work to build. So much effort went into that. It's so useful. And like, I never use it.
I know it's there. I know it could solve my problems. And I wonder why sometimes. And
I think it's because when I encounter like a startup problem, like my first thought isn't
go to this database. It's like, let me talk to a friend or let me talk to my brother or
let me like ask a mentor or let me like search Google or let me just sit down and like figure
it out myself. Half the time, like that's my resource. And so I'm somewhat skeptical
about indexes. It's why I haven't built one for any hackers because I'm like, well, I
just never use them. But I think people would use them. Some people for sure would, you
know, if the homepage of any hackers was like gigantic directory of startup topics for help,
like people would probably use it. And so I'm conflicted.
I think I am too. And for me, it's like, okay, so it's a hypothesis. What do you do to test
it? Well, I can ask on Twitter, would you use an index? And I'm dubious about whatever
80% will say, yes, no one will use it, right? Or the opposite. So what I was trying to do
was talking to again, it's just a producer Aaron and saying, what's the minimum? What's
the MVP of this? You know, could we just get a through D index or could we maybe just get
50 episodes indexed and you click through and it takes you to the transcript and you can
listen to the episode if you want. So then we could see, do people use it? And if no
one does, we're out what, hundreds of dollars in labor or whatever it is the exception.
And the reason I think that maybe some people would use it as on Twitter, I often will get
a, I'll get a question or on indie hackers, I'll respond to something or whatever hacker
news, just any of these forms where someone asked a question about being acquired or sales
funnels or email marketing or whatever. And I will say we talked about this for 40 minutes
in this episode. Yeah, this whole idea of sort of content reuses,
I think, criminally underutilized in podcasts, because I've been thinking about this with
any hackers. For example, if we wanted to do like an indie hackers book list, like let's
talk about the books that all indie hackers like the most. Every single time I have a
podcast episode, after I finished recording, it's like, Hey, Rob, like what are some books
that have been influential to you record that and it's like, you know, an extra like minute
or two for you, it's not going to matter. But by this point, I would have like 200,
you know, different people who told me their favorite books or their favorite resources
or their favorite whatever and I could easily like, you know, ship it off to a VA to put
together a resource somewhere else. And it's so easy to do that. But like, I haven't really
used that part of my playbook very much. I know, I know. And I think not being strategic
and playing you and I what we're saying is we kind of play checkers instead of playing
chess. And I think that's a bit of a mistake or it's a mistake, maybe it's a strong word.
But I'll tell you what, I regret it. I regret having done this podcast started to rest for
11 years now, and not having been more strategic about it and not having spent more time and
what I don't regret is the last two years because I have, I have doubled down on all
types of stuff, redesign the website, change the hosting, whatever. It got different analytics.
I was going to say better analytics, but I don't know about you, man. Podcast analytics
suck and I use three different analytics providers and they gave me wildly different numbers,
like 100% different from one to the next. And I'm just like, I don't know how many listeners
we have. I can give you an idea, but I don't know for sure. You know, are you on chartable?
Yeah. Chartable is the one, does it tell you listener count?
Chartable attempts to basically aggregate your metrics from like every podcast player.
And so like all of your MP3 links on your podcast feed will go through like a chartable
link and they use like, what do they call it? Like the IABV2 certified statistics, which
like requires them to like just do a bunch of stuff to try to give you the most accurate
download counts. They need to filter out bot traffic. They need to filter out like repeat
page on the same IP address. And like, as far as I'm aware, like podcasters, it's like
it's the Wild West. Like I was on this weekend startups with Jason Calconis and I was like,
how many downloads are you getting? It's like, oh yeah, a couple hundred thousand per episode.
I was like, really? Who's your hosting provider? He's like, Oh, we just throw our MP3s on an
Amazon S3 bucket and we just count the number of downloads. I'm like, that's not accurate
at all. That's like the least accurate possible way to do it. And so his numbers are probably
inflated like 510 X at least. So like, who knows, right? He might tell advertisers that's
what they get and they might be able to charge based on those rates and nobody really knows.
Right. And that's the thing that, so no, I haven't, I obviously I'm not uncharitable
because I had thought I'd heard of it and I'm using a service that tells me where we
are in the Apple podcast charts. It tells me where I rank because I care about that
for discovery. It's a good time to be podcasting. It's one of those like mediums that if you
invested in 10 years ago, which you basically did, uh, it's a risk, you know, it's going
to be around and like, obviously it's bigger than ever. It's humongous. Apples get into
it more than they ever have. Spotify is getting into it more than they ever have. Google's
got their podcast player. Let's talk about some other trends. I saw you tweeting about
your Oculus quest, uh, VR VR is near and dear to my heart. Cause I've been so bullish on
VR for so many years and it has not taken off and it's not become anywhere near what
I would hope it would be. And I just got an Oculus quest, I think in January and I was
super excited. It's the Oculus quest to, was that the one you have? Yeah. And it's $300.
And then if, if you are going to use it with multiple people, cause I have, there's four
of us in the family, right? With two kids and you get the little head headband. I think
it's 50 bucks. That's adjustable. So everyone can use it. But if you're even more baller,
you spend 150 and you get the one with the battery pack that attaches to it to give you
extra battery life. My kids love it. And we will attach a beat saber or something else
to actually crank it up to, to experts. So they get some type of exercise in the winter
cause they can do it in, you know, they enjoy it, but they also move around a bunch. Yeah.
I've been playing through what's the, there's a star Wars, Darth Vader thing. You know,
we're in the second part of that trilogy. It's so deep. I mean, you don't, you're not
attached to anything. All you just buy an app on your phone and it's 15 to $30 usually.
And then suddenly it's just in your headset. And, and I'm kind of becoming the, I'm, I'm
an old guy now, you know, I'm not that old, but like, I don't like new things. It's like,
ah, get off my lawn. And I put this thing on the first time and I was like, this is
unbelievable. Like VR has arrived with this thing because you're not attached to any,
there's no wires, right? It just, that's the amazing thing. And the graphics aren't, they're
not like the, the rift, you know, or not like, I mean, there are other VR headsets that are
so much better, but it has not slowed down for me. I'm bullish now. I've always been
bullish on all new stuff cause I'm a technologist right now. I want this stuff to work, but
I've been really disappointed with the VR headsets and the cost. And it's like, I'm
not going to get a big windows machine and attach it to it. But I think VR and AR are
arriving like as we speak. Yeah. I've been hoping that they would. And I got the quest
and I, unlike you, I have not continued to use it. It's like in a drawer over there and
it's like, I'm just so excited about it. Like I want it to be great. And the experience
actually is pretty great. Like the first time I put on my headset, you can kind of choose
like your home environment, what's your background going to be? And like, it shows this like
cool cave and a canyon with like a living room and like stone tables and stuff. I'm
like, oh, this is awesome. And then like the apps for me, it's just mostly games and I
like games just as much as the next person, but like I'm thinking like, okay, I want to
be like, you know, floating in space with like 10 monitors around me and like managing
like any hackers on my Twitter account and everything, right? I want like the coolest
VR experience possible. And for me, the apps just aren't there. Like I can't be productive
and VR like it's not better for me. Like it's better for me to chat to my friends on my
phone than it is to chat in a VR environment, which is crazy. If you read any sort of like
sci-fi book about VR, like think about all the coolest apps, like everything makes way
more sense because it's an entire digital world created from the ground up. So I'm bullish
on it, but I think the apps aren't there. Like there is no Twitter for VR, you know,
there is no Asana for VR, there is no Gmail for VR. And so you just kind of like end up
playing a lot of games.
I would agree with that. I think that the fidelity of paint writing or typing or anything
is it's not there yet. And in fact, there's a whiteboard app because this was a big thing
like when Derek and I were building drip is when we were separated for any length of time,
it's like we can't whiteboard together. This is really hard because he and I would sit
from whiteboard for three hours, you know, and just like hash out really hard problems.
And I kept saying once VR, once we can VR headset into a whiteboard, we never need to
see each other again. And, and there is a whiteboard app and the fidelity is too low.
You get when you write, it's you're like writing with a big crayon because it, it's the detection,
it's not there, but it'll get there, right? It has to, it has to get there. And once it
gets there, it'll, I think it'll be game changing. I agree with you. I want it. I want to be
able to work in it. But what I will say is that when COVID hit and we couldn't do even
the tiny seed group, uh, tiny seed microconf, right? It's four of us. We wanted to get together
in person to hang out, do a one or two day hangout time. Instead, we did it in VR and
we did a few games that are, that are cooperative games. Like there's one layer preparing food,
right? And you're chop, chop, chop. And then you like canned the sandwich to the person
next to you and they're supposed to put the cheese and the thing on and the customers
are all huffy if you do it wrong. And so we were gaming, but also hanging out and talking
in between and we were chatting and it was a way for us not because the four of us will
sit on a zoom call and it's like, this is great. You know, it's like, let's do more
work. I feel like I'm working right now, but at least then we could, elven assassins, another
one, right? Where you're like shooting, you know, orcs from far away. So that was, that
was nice. It was like team evening, team retreats where you, you know, each of us having a frosty
adult beverage and hang out. So I think that's been a valuable thing.
I can't imagine like, if you wanted to like craft an experience from the ground up to
just make people feel like they're in some sort of corporate work environment while talking,
like you would make it look exactly like zoom. Just everything is ugly. Everything is spartan.
It's just completely stripped down. Like they are aggressively trying to bore the hell out
of you, but I'm a fan of multitasking. Like my brother and I will do calls pretty much
every day and we usually just use telegram because we'll be typing in telegram. You click
like one button and you're on a call. It's just the lowest friction, but like it's hard
for me to just sit there and talk and do nothing else. Like even right now I'm like animated
like moving my hands and stuff. So like with him, like we're both like pacing around our
apartments and then half the time we're zoning out because we're trying to multitask and
do other things while we're talking. But if I was like playing some cool VR game at the
same time, like that will be super interesting. And the reason it doesn't happen for me is
because like the friction to get like go get my VR headset, make sure it's charged, put
it on is too high. But if I had these other productivity apps, I was kind of like there
all day. Like I'm going to stare at a screen all day and might as well be a VR screen.
Then it wouldn't be high friction because I'd already have the headset on and just press
a button. Now I'm in like a chat. No, I think that I think the friction pieces is a big
part of it. Interesting tidbit that I'll throw in it tangentially related. You were saying,
cause I'm the same way where I need to be moving around or I like to move my hands.
I like to talk. I have switched my, my sat, I use Savi Cal instead of Calendly. Savi Cal
is a tiny seatback company. I've switched my Savi Cal link now to where it does not
default to zoom. It defaults to enter your phone number and I will call you because I'm
just kind of done because I can walk. I can go, I live near a lake and like it's 65 and
sunny out today. And I want to, I've been walking almost every day for just an hour.
Not even as exercise cause I do other stuff harder. You know, walking is not exercise
for me, right? I'm just in decent enough shape, but I just want to be outside and not sit
in front of a damn computer for eight hours a day and not stare at the screen, right?
So I'm going a little analog. It's an experiment. I'm only about a week into it. So far it's
been amazing and I have no qualms about it. Obviously there are some that need to be zoom
because you're going to share screens. You're going to do Excel. You're going to walk through
Google sheets or whatever.
There's also these, a lot of these companies out there that are trying to make these like
team meetings better gather, gather.town, which is the coolest. I think it's like, it's
so fun to, you have like a little virtual world and you have a little character, you
move them around and you know, when your character is next to somebody else's character, then
it connects you in an audio chat. So it's almost like you're, you know, a real experience.
And there's a bunch of other competitors to this that are trying to basically capitalize
on the fact that everybody's working remote, but zoom is super boring, super dry, and just
isn't engaging.
Yeah, for sure. So we use them for microcomf remote about a month ago. And to your point,
it's like an eight bit version or 16 bit version of a like Zelda or an old King's quest game
and people were blown away. Most people, now we had some curmudgeons who were like, this
is super, you know, like a fad, right? This is too kitschy, like for a professional conference,
but only a handful. And overwhelmingly, aside from, you know, those few people, people loved
it because it was, it does kind of almost a little bit replicate the hallway track.
It's my favorite thing about like the sort of COVID ecosystem apps. And maybe like two
years ago, it was like, you know, pushing it forward to even have video chats at your
company, you know, like people just didn't do it. The adoption rate was super low, most
people were working from the office. And then with COVID, it's like, okay, well, now everybody's
on zoom. So like, we can think about the next level is and it's gathered and it's all these
other tools are just look cool or look a little bit more fun. You know, now we have a clubhouse
and we have Twitter spaces, we're like, what if we have audio only, like the fact that
like remote conversations has just been so mainstreamed now means that people can just
push the envelope and try new things. And so I think that's what's kind of fun, you
know, like the idea that you can build an app that looks like a video game, and real
companies are using it like that would be unheard of two years ago. But like now it's
like, yeah, fine, let's try it. You know, or like, a lot of people building like these
icebreaker apps where they're like, hey, companies are all remote right now, their employees
don't know each other, don't get to talk to each other. Like what if we put like a goat
on your zoom, on your zoom video, and you could like talk to this goat, you know, or
what if we like, you know, design like these sort of like cool icebreakers, and people
are making real money doing this kind of stuff, where, you know, it's just in the past, not
a viable business.
Yeah, it's picks and troubles, right? It's you build the, you know, if you're in the
gold rush, do you want to be the miner? Or do you want to prospect? Or do you want to
sell picks and shovels? And that I've viewed sass as picks and shovels forever, right?
So 15 years ago, when I started talking about it, and that's really the bet that we're making
with tiny seed is that, you know, when we get, we get more, we don't get more applicants,
we get more applicants with revenue, every batch we've done so far, and even more revenue
than, you know, batch one and batch two had more revenue and batch three had more revenue
than batch two. And so there is this trend of more people using sass today, then a year
ago, and are those going to go, you know, those users going to suddenly go away? Are
those needs going to go away?
I think we see the same thing with the funding environment, where from where I said, it seems
like there's so much money looking to go into startups right now, like everyone is investing
in every sort of they can, Riverside just announced like, I think on their homepage
right now, it's like they just raised nine and a half million dollars, and there's some
crazy valuation. It's like every startup is just like, yeah, worth $100 million now.
And like two years ago, that was not the case. I mean, funding wasn't bad, but it wasn't
as easy as it is now. And I think with tiny seed, you just finished your second fund.
And you raised, how much did you raise?
I wound up being 27.7 million.
That's crazy. Like that's an insane amount of money.
It is. Our first one was four and a four and a half or 4.4. And I remember when we first
started raising the first one, I told my co founder, I was like, I think if we can raise
like a couple million dollars to do a batch, like I'll be great. And we got to four and
a half. And I was like, this is amazing. And now here we are, you know, five, six times
the size. Their money's cheap right now, and it won't be forever. So that's the thing I've
been through booms and busts. And a lot of folks like if you've only been a professional
for 10 years, you don't remember 2008 2009. And you don't remember the dot com crash right
of 2000. And you don't have to remember them to take this advice. Like in 2000, it felt
like money was free. And it was being sent to I mean, people with a business plan were
just getting all this money to do whatever, right? And then it eventually crashed. And
from from that crash rose Google. And I think Facebook was a few years later, but blog spot
and blogger and YouTube came out of that a few years later. And and then sass came out
of that in 2005 to 2010. And then there was a big crash. And there again, there was a
bunch of money, bunch of money, because it was cheap, because the Fed was printing it
and you could borrow it historic lows, and then crash 2008 2009. Now, the places that
didn't crash is like if you're bootstrapping and you're super cash efficient, you might
see a few rough months, or you might even see six rough months. But if you're not just
burning through cash, like you'll stay alive. And you come out way stronger on the other
side of that, right? And you can slingshot and it's good to have it's good to have that
wind at your back. And you're right, money is cheap right now. Don't think it will be
forever. And and I do are we in a bubble? And I mean, kind of we're kind of we go through
cycles, you know, and if you think about it, the last bust was 13 years ago. Now, I mean,
we really haven't had a major, you know, we had the obviously last March, during COVID,
there was a one month crash. And then in 2016, January, there was a kind of a one month crash,
but really a sustained bear market.
Is there an argument to be made that there could be some sort of almost irreversible
shift? Like things will always go in cycles, there will always be boom and bust periods.
But there are some things that are happening nowadays that are like, just different, right?
Like people are more used to the internet and more, I think, confident and internet
based companies today than they were 10 20 years ago. It's easier for the average person
to invest, like so many more people are becoming angel investors today than we're in the past.
There's now like, increasing crowdfunding limits. So you can crowdfund a startup like
Sihill from gum road basically raised like five or $6 million or something from just
random people who weren't even like, I don't know, they're just putting in like five or
10 bucks, you know, they're just like, okay, well, I'll invest, who knows, you know, this
sounds cool. Like my mom asked me about investing in startups, you know, like she wasn't asking
that 10 years ago. And so maybe to some degree, like just the number of people who are trying
to get in at an early stage, it's just going to keep going up and up and up. And I don't
know if the number of people creating startups is increasing at the same rate.
I think there's two factors at play or multiple factors. One is you're right, the crowdfunding,
even the kickstarters, you know, that whole ecosystem has allowed there to be way more
products created. And you can say there are way more tabletop games because tabletop gaming
is like one of the biggest Kickstarter categories. I should know I've backed literally hundreds
of them. Remember how we remember how we mocked me profusely last time about my audible addiction
how I have like 800 audible books, you do not want to see I believe it's 250 300 kickstarters
back. I do think crowdfunding with startups is going to do similar things. I do think
there will be a pretty big failure here in the next six to 12 months. It'll either be
an out and out scam, or it'll be someone over representing, or it'll just be something that
fails big. And that happened with Kickstarter and indigo go and it kind of level set people's
expectations people backed off on things. There is a lot of growth happening now. But
man, there is across the board, because there's so much money. There's none of us are traveling.
Most people are not eating out. None of us are taking vacations, we have money to put
into other things. And so I'm in collectibles. And if you look at sports cards, you look
at comic books, you look at art, it's all crazy. Like it's these things are up 35 to
50% over the past 12 months, you look at startups, similar more money going in that you look
at crypto Bitcoin from a K to 56k or what you know, a 60k in the past six to eight months.
There's just a lot of money going in. That is great for us in the short term. It's not
sustainable in the long term. But there's secular trends. And there's cyclical and secular
short term and cyclical are these long term changes, right? That's the two things we're
holding holding intention is that crypto and collectibles and maybe money going into startups
can't sustain itself like it is today. But to your point, there are a lot more people
coming in with crowdfunding and and the accreditation laws are hopefully going to be changing,
you know, to where more people can be accredited. It's not just a revenue based thing. It's
you can take a test, right and become accredited or to raise a fund when we raise tiny seed
fund to one of the biggest limiting factors. We could have raised a lot more money than
27.7. But we could only have 99 investors. That was our limit. And that's what kept us
from raising 40 50 million, we had to turn a bunch of people. There were people who said,
I want to write you $100,000, $150,000 check that we had to turn away. Because if you just
do the math, 100 people, 27.7 million is $277,000 minimum, our minimum was not that high. But
that's the kind of thinking you you're gonna raise a $50 million fund from 99 people, 500
K a piece, right? So we are actually, we started we got in touch with a nonprofit, and it's
an entrepreneurial organization. And we have had phone calls with the SEC to try to change
this, as he has told us, you have to lobby Congress, or you have to get like, this is
a law, like you literally need an act of Congress to fix this. And we're like, ah, we thought
the SEC could do it. So now they're like, we're getting in touch with someone on the
hill. And we're gonna try to be we've gathered a group of, you know, general partners of
funds, also think that the 99 investor limit is a problem, you know, and it's keeping folks
from being able to invest. So we're hoping to change that over the few years to Yeah,
a ton of this stuff, the crowdfunding limit got raised, the sort of rules becoming an
accredited investors you mentioned, or sort of getting lacks, and also these other limits,
which just is going to mean more and more people being able to invest. And typically
people think about, okay, what can I invest in like the stock market? But now it's like,
okay, well, crypto as well. And also, like maybe angel investing into startups. And so
it's crazy to me that there's so much money going in. And there's just so many different
things you can do. You know, you don't have to necessarily create a SAS business and do
this sort of tried and true thing that you and I have been talking about for years, you
can maybe make a tabletop game and put it on Kickstarter, you can make some sort of
crazy crypto thing, you could start a newsletter, right? I bet you, you know, a couple years
from now, people will be raising lots of money to build newsletter companies or today, like
that's not really a thing that people do, it's got this individualistic pursuit. And
so I'm optimistic, I just like seeing things moving and shaking and things changing up.
And I spent a lot of time thinking about what I would be doing if I wasn't doing any hackers,
you know, would I do another startup, but I do some sort of unicorn targeted thing,
you know, what I do, like, some just random side project, what I write, you know, and
there's just like a million things you can do now that like you couldn't have done 10
years ago, because the market just wasn't there, there weren't enough people consuming
and it would have been much harder. You see a lot of companies, obviously, you just raised
like a $30 million funds, you've got to invest that and a lot more companies. What do you
think any hackers should be thinking about? You know, what are you interested in? What
are some of the trends and spaces that are sort of up and coming that you think people
can basically build successful businesses in?
Something that enables remote work is big, remote work is not going away. And it's only
going to be more adapted, the creator space, the maker space, like you're saying, newsletters,
I mean, these things are all on on our radar. And the third space isn't just one space.
But there's almost this refresh in a bunch of different verticals that happens every
so many years. So like, constant contact started in 1999 2000. And then MailChimp came in 2009.
And it's like, we're the new, their new interface, a new approach. And then you saw a drip and
convert kit come in like 20, where are we like 13, 14, 15. And it's like refreshing.
So these big, and now you see like savvy Cal, right? With Derek Rimer is a Calendly came
five, 10 years ago. And then transistor replacing the older podcast hosting companies. Yep.
Transistor and Castos, right? Replacing with Libsyn, I think is a big one. I think there
are a lot of spaces that are ripe for a refresh, if that makes sense. And it takes, here's
the thing, like, you know, I always talk about the Stairship approach. And if you're if it's
your very first app, don't go into these big competitive spaces with a hated, you know,
a hated large competitor, because it's really hard. And usually you need to either raise
some money or have some have a lot of experience or be a really good app maker. If it's your
first time pick a small idea, I would probably go into an app store, or you know, a plug-in
repository because your distribution is taken care of. But if you are at that point where
it's like, I'm going to really tackle something big, and you do want to be, you know, in these
ecosystems, I think looking at these large spaces where competitors are getting just
a little crufty. And frankly, a SaaS app that's maybe six, seven years old, it's a little
crufty. They're usually a little crufty. Most are not maintain, you know, most are you did
that you can't keep the UX and I can't keep the new paradigms because of just legacy gets
almost built into them. Right? Yeah, there's a sort of takeaway from the state of independent
SaaS survey that you did for 2021. And you kind of talk about where people are getting
their ideas from. And then like the average sort of revenue based on where you source
your ideas. And the highest category was I copied a competitor, which is shocking to
me, I didn't expect that to be like that beat out. I pre sold my product that beat out like
I had, you know, I bought this company or asked my audience what to do, or I built in
a prototype or MVP, like the best way to sort of valid an idea. Apparently, it's just copy
what's already working from the competition is great.
Yeah, I so I would have expected I bought the product to kind of be number one and then
copying the number two. Now copy is a strong and that's the verbiage we used when I if
someone wants to copy, do I think that's a viable approach? Absolutely I do. But I think
you need one of two things or both to do that one. Just a straight copy makes no sense,
right? Because everyone's going to keep using the one with the brand. So you have to either
have some pretty like proprietary traffic channels, like you're really good at SEO,
you know, or you're really good at integrations, or you have a network or an audience that
you can use, or you can build in public, or you have a really unique feature or positioning.
And that's so you can take like MailChimp was and it still is the number one email marketing
in the world, right by volume. And so when drip was launching, we didn't just say, Look,
we're MailChimp clone, we said, we're MailChimp plus automation, right? We're MailChimp plus
something they don't have that people were asking us for. Later on, of course, we position
that was our positioning. And then people were like, well, MailChimp is cheaper. And
then we realized we want to position ourselves against the more expensive competitors, which
were the infusion softs, hub, Spartan market. Oh, and that's a lesson that I learned. But
so you need one of those two things, just a copy. No, but a copy with Yeah, proprietary
channel, you know, kind of a unique position that resonates with people.
Very cool. Well, listen, Rob, it's been fun. I like these sort of casual chats. And I'd
love to tell listeners where they can go to learn about what you're up to.
Absolutely. Yeah, folks want to listen to me talk about this kind of stuff every week
for 35 minutes. That's startups for the rest of us.com. And Rob Walling.com. If you know,
they want to keep up with me, I write essays now and again, and I guess Twitter, right?
Yeah, at Rob Walling. Maybe that's a good one. All right. Thanks again, Rob. Absolutely.
All right.