Garrett Diamond built a business on a crowded marketplace, one where his app was far from
the only one of its kind, and yet he was able to cut through the noise, find hundreds of
paying customers, and eventually go on to sell his app for hundreds of thousands of
dollars.
I'm Corlan Allen from IndieHackers.com, and in this interview I'll be talking with
Garrett Diamond, the creator of Sifter, a simple application for teams to track their
bugs and issues.
There are hundreds of other bug trackers, but the reason that Garrett was able to do
well was that he picked a very specific and targeted paying point, and he built his product
entirely around that.
This led him appeal to a certain group of customers in a way that his competitors couldn't.
There's a lot to learn from this interview about how to build a product that stands out
among the competition, how to communicate with customers and get them to buy your product,
and about how to experiment and find the best ways to grow your company.
Hopefully you guys will enjoy this conversation I have with Garrett as much as I did.
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All right, this is Cortland here from NdHackers, and I am sitting down today with Garrett Diamond,
founder of Sifter, a business which he started years ago and has since sold.
Garrett, how are you doing?
I'm good.
How are you?
I'm doing excellent.
So, I want to start off by talking about Sifter.
I know you've done a great many other things besides Sifter and since Sifter, but I'd really
like to start with talking about Sifter, so can you tell us what it is and how you got
started?
Yeah.
So, Sifter is a bug tracker.
It was a really, really creative, unique idea that I had.
I founded it in 2008 and was more or less a solo founder.
I had a little bit of help with some of the ancillary tasks, but as far as design and
product and support and marketing and all that kind of stuff, that was pretty much all
on me.
I had just always been fascinated with bug and issue tracking just because my first job
out of college, I was exposed to it in a really well-oiled machine, and my second job was the
complete opposite, so just the contrast between those two jobs kind of showed me that not
everybody has the process down to a science, and I just sparked an interest, and then later
on when I was doing a lot of consulting work, almost kind of agency stuff, one of our biggest
struggles was getting our non-technical clients to participate with the issue tracking, right?
And not so much find the bugs, but find the things that you don't like about how we've
implemented this and help us fix it and that kind of thing, and we tried half a dozen different
bug trackers, and they'd log in once and kind of be like, I don't know about this, and then
they'd never log in again and they'd just email us the issues, and invariably one or
two issues slips through the cracks because they wouldn't use the bug tracker, no matter
how religious we were about putting it in, and so the fact that they wouldn't use a bug
tracker, and this is for smallish teams, for big huge teams, it's not too much of an issue
because you can kind of force people to do it, but for a team of five and a couple clients,
it's just big enough that it's helpful, but it's just small enough that if they don't
want to use it, there's not a whole lot of arm twisting you can do, and so it kind of
got to the point where it's like, well, if they won't use the bug tracker, we can't use
a bug tracker because it's two different worlds, so my philosophy kind of got to the point
where it's like, it doesn't matter what a bug tracker's capable of, if the team won't
use it, it's useless, and so big teams where they're all developers and everybody's pretty
technical, it's not too hard to get everybody to adopt something like Jira, something really
powerful and flexible, but that's just overkill for smaller teams, and so I was like, well,
I just want to create something that'll be much, much, much simpler for those smaller
teams, and a lot of bigger teams would view it as crippling almost because it was too
simple, but for the smaller teams, it's kind of just right, so kind of the Goldilocks version
of bug tracking, the just right version for small teams, and so yeah, I was just kind
of, the way it started too was the, I think probably one of the more interesting things
was I didn't really plan on building it, I just started designing it and mocking it
up and kind of thinking, oh, well, maybe I'll create something open source because I didn't
want to deal with support, and I didn't want to have to take money online because this
was pre-stripe and Braintree had just barely come around, and the idea of taking money
online just scared me.
I was like, Authorize.net, I'd heard too many horror stories, so I did not want to start
a business, but by virtue of sharing these ideas and the mock-ups and things, a lot of
people started expressing interest and encouraging me to do something more with it, and eventually
I got worn down and said, okay, I'll just start a business, and so one of the common
questions everybody asks is, how do you get your first customers?
For me, it was like, well, my first customers kind of got me.
Right.
So.
You're flipping around.
Yeah, and so to this day, I feel like that's still one of the best ways to do things is
just work on things in the open and do things, and if there's interest there, you'll find
out.
Yeah, that's really cool because you sort of took this combination of expertise based
on your own experience in school and at these companies, combined with your public writings
and the validation from other people to get this huge head start in terms of validating
what you're going to work on and finding your first customers, which is pretty much the
exact opposite of what most people I talk to did.
They're scrambling to make sure their idea is something that people need months after
they've already started building it, which is, of course, the hard way to do things and
the wrong way to do things if you can avoid it.
So that's a great way to get started.
This was in 2008 when you started Sifter, right?
And back then was the bug tracking market crowded because I know today there's like
a ton of bug trackers, but back then were you worried at all that while there's so much
competition and I'm not going to be able to target a good niche or I'm not going to be
able to rise above the level of noise and all my competitors are creating to get customers.
I think it was a combination of not being scared, but also being ignorant.
The biggest thing was it's always been a crowded market and it always will be because there's
always going to be a need for it and there's honestly still probably plenty of room in
the market for more.
The thing is most bug trackers are designed by developers for developers and I was more
of a designer than a developer, not really even a designer, an information architect.
So a lot more interested in kind of user experience.
And so for me, the biggest problem to solve wasn't can I build a bug tracker, it was can
I build a bug tracker that non-technical people won't run away from screaming.
I felt confident that there weren't going to be many other people that cared about doing
that.
There's just not a lot of people in kind of design and user experience who were really
passionate about bug tracking, right?
The only people who are passionate about bug tracking are developers and developers are
going to build the tool that they want for themselves and they're not necessarily thinking
about their clients and that kind of thing as much.
And so I just felt comfortable that I was going to take it in a direction that nobody
else really cared about or would pursue and that I'd have a unique enough take on bug
tracking that there was enough space for me to carve out a little niche and make a good
living.
And so it's so telling that focusing on a good user experience ends up being like a
unique take.
Like no one else cares about the user experience.
But it wasn't necessarily a good or bad user experience, right?
It was a good or bad user experience for a specific audience because plenty of developers
hated Sifters user experience.
Our audience was the developers who may have felt this doesn't serve my needs enough, but
it gets my customers actually using it so I can forego the fact that it's not perfect
for me because they're actually going to use it.
How much do you think of Sifter Success and the development of any product in general
relies on or is helped by, I should say, targeting a really specific niche and making trade-offs?
Because I know I talk to a lot of people and they say, well, I don't really want to target
a small group of customers because what about all these other people who might be my customers
and who might like the product?
It's kind of like this situation where it's easy to be afraid of losing out on potential
business and so you make a product for everybody.
Do you think if you would cater to developers' needs a little bit more that Sifter would have
been harder to succeed with?
I mean, it's a double-edged sword, right?
If you go too narrow, you limit your audience.
And if you go too wide, you blur your message.
It's almost an art to find the right degree of both.
And I feel like with Sifter, one thing I could have done more was done a better job of incorporating
things that the developers would have appreciated in ways that it wouldn't have necessarily
affected the user experience negatively.
But I think it definitely would have helped too.
So the other thing too was I was building a tool and this was, in hindsight, probably
one of the things that made it the most difficult was my target audience was never going to
be the people who were paying for the tool because my target audience was my customer's
customers.
And so Sifter's only real appeal was for customers who were struggling with the fact that their
customers wouldn't use their bug tracker.
And again, in a way, it was a good niche because there was anybody else out there doing that,
but it was a bad one because it is limited.
And so it's just one of those things, it's a blessing and a curse, and you kind of have
to make the most of it.
It made marketing difficult because I wasn't directly removing my customer's pain, right?
I was removing my customer's customer's pain.
And so it was an indirect pain for our customers.
And that made it difficult to have a compelling message for them unless they had that problem
and really understood it well.
Because for most developers, it's not necessarily a problem, it's just, oh, well, that's fine,
they can email them to me, I'll deal with it.
But yeah, it seems like a difficult thing because you kind of have to, like you said,
either they have to already be keenly aware of what the problem is or you kind of have
to educate them, like, hey, the reason your clients aren't using your bug tracker is because
the bug tracker you're using sucks for non-technical people and you should switch to a totally different
one.
Yeah.
So you got your first customers were people who were supporting what you were doing and
working on and interested in your take on bug tracking before we even launched.
What was involved in building the initial product?
How long did it take you and what kind of tech did you use and how did you get your
first users after your first user, so to speak?
So it's Rails, basic Rails, MySQL, setup, nothing super fancy.
I mean, when we launched, it didn't even have file uploading or search.
It was very, very, very simple, almost too simple, uncomfortably simple.
And it took me, I quit my job and switched to freelance, juggling freelancing and sifter
in January of 08 and I launched in December of 08, like publicly launched.
The beta started maybe a month or two before that.
And so I'd say, you know, that total time was 11 months.
Probably half of that was on sifter, so six months.
And again, you know, back then the billing stuff wasn't really there.
So like I wasted a month building a billing system, which these days you wouldn't have
to do.
You can just plug in Stripe or even Braintree is better now.
So there's, you know, there's so many options.
I mean, I love that knowledge that I have and that experience and understanding of the
billing system, but yeah, I would have loved to not have to build that.
It's interesting how like every, every few years there's always something you can look
back and say, wow, we've got it so easy today because I remember like developing web apps
back then and I wasn't implementing any billing systems, but still like the only thing anybody
was talking about in 2008, 2009 was how one developer can do what it took, you know, a
team of 10 or 20 to do back in like, you know, the nineties.
Yeah.
No, it definitely gets better.
And I think for me, that's the biggest, I mean, now that I've, um, got a regular nine
to five job by the biggest haunting temptation for me is like, oh my gosh, just imagine what
you could do now with all the experience and the better tools.
And then I've just got to kind of slap myself and be like, no, no, no, no, no, no, no, at
least with any hackers on my thesis is that we're going to see more and more independent
developers and non-developers to starting businesses because the amount of leverage that they have
with all the tools is such that like you, it's, it's an easier path now that it ever
has been to, to just completely issue reliance on a team.
But for, for better or worse, just because it's easier for you, it's easier for everybody
else too.
Right.
Right.
Right.
And, um, and, and not necessarily like I'm not a big competition person.
Like I feel like focusing on competition is almost a distraction, um, but it's important
that you kind of have your own story.
And I feel like, you know, too often too many people are like, oh, my competitors are doing
this and that.
And you know, what should I do?
And it's like, you just, it's not about what you should do so much as you just shouldn't
do what they're doing, you know, like figure out your own thing and carve out your own
world.
Um, but you know, there's going to be more and more and more and more competitors now
because it's easier for everybody to do everything.
So it's even more important to really kind of stake out your area and who you are and
what you're building and what you're offering.
I think.
Yeah.
I agree completely.
I just interviewed, uh, this guy, the audio from this company, proposal for indie hackers
and he's got online business proposal software.
And one of the things he talked about in his interview was how much he like willfully ignored
all of the competition.
Like he refused to even look at their products and he wanted to talk to customers and figure
out the, like understand the problem he was solving and come up with his own unique solution
without being biased in terms of how the product should look.
And I think that's one of the things that's going to help him and will help others in
the future too.
And with there being ever more competitors, like the importance of finding a niche is,
is only going to increase.
Like you're going to have to probably be in a market that's not winner take all and definitely
attack a niche where it's small enough that you can make, you can carve out your own territory
but big enough where you can actually make money doing it.
Yeah.
And the other thing about competitors is everybody assumes that, you know, if you imitate or
worry about what your competitor is doing, you're assuming they know what they're doing
and chances are much more likely that they're in the same boat as you and they don't know
what they're doing.
They're kind of figuring out as they go.
So imitating them isn't going to help you.
It's just going to mean you're learning a step slower than they are.
You really have to kind of make your own path because you're going to shoot yourself in
the foot by trying to follow them around and worry about what they're doing.
Because yeah, I was the same way with sifter.
I mean, I was familiar with lots of bug trackers from years of earlier experience.
But once I started building sifter, I couldn't have cared less about any of the other tools
out there.
I mean, I was interested from a user of tools, but from a like, I totally avoided even looking
at other bug trackers.
I was like, Oh, another one launch.
Okay, cool.
And then I don't know, probably half the ones that kind of flew across the radar were out
of business within a year of launching, you know?
Right.
So I think everybody just thinks, Oh, it's going to be real easy.
I'll just launch and I'll be a millionaire.
And you know, definitely doesn't work that way for some people, but you know, not everybody.
That's pretty rare.
If you had between.
Yeah.
And I think that's one of the things that is really cool about doing podcasts with people
like you, because people can listen and they can hear about like the actual nitty gritty
that's going on behind the scenes.
I'd be like superficial information that I got from, you know, the Facebook movie or
a tech crunch article is the tip of the iceberg.
Yeah.
So Sifter, you started with a small set of users, you launched it, you had a beta over
the course of, I think the eight years that you were running it, were there any like really
big things that you changed that like drastically increased your revenue or any big lessons
you learned that really changed the course of the business?
No, there wasn't anything big that drastically changed the course.
There were lots of little things that kind of adjusted the course.
And I think the biggest thing I learned is that there's rarely anything that will change
the course, at least in terms of features.
There's certainly a lot of good and targeted marketing that can really change the course
of a business if it's done well.
But even marketing, you really have to stick with it, right?
There's not, you know, go spend $10,000 on AdWords and all of a sudden you're going to
have more customers and you know what to do with like it's still marketing is hard work
too.
There's not a silver bullet with marketing.
Right.
What are your marketing strategies like?
Just keep blogging and sharing and we spend a fair amount on ads over the lifetime of
Sifter, probably something like $20,000 over eight years on everything from Daring Fireball,
which was a lot cheaper back then.
And that was a really effective one for us.
The deck, definitely spent some time experimenting with AdWords, but it was just not fun.
And I wasn't excited about it, so it was hard for me to keep at it.
And then lots of display ads here and there and sponsoring some sites that we liked and
sponsoring podcasts that we liked.
Stuff like that.
I think a lot of people's hope when it comes to advertising is that they're going to measure
the lifetime value of their customers and then hit on some sort of like repeatable winning
formula where they can buy a customer for a dollar and make $2.
Yeah, I mean, that's the holy grail.
Yeah.
And so there was never a point where you were like, okay, well, this one form of advertising
is it and we can just do this to infinity and it'll work every time.
Yeah.
I mean, for us, I don't think there was any one kind of thing that really was powerful.
Like I said, the Daring Fireball ad, I think we spent $2,500 on it.
And that was like probably early 2009.
So we spent $2,500 and it got us probably 30, 35 customers.
But that was the only thing I think that really moved the needle.
And that was only moving the needle because we had probably, I don't know, 100 customers
at that point maybe.
And so 30 customers, 30, 35 customers, that's a big deal when you've got 100 customers.
But down the road, 30 customers, that would have been like, I mean, it would have been
nice, but it wouldn't have been life changing.
It's just like gets harder and harder for any sort of individual effort to move the
needle once you start growing.
But in some ways too, that's all the more justification for experimenting and trying
different things to find the thing that could do that.
I think the problem is, it's a healthy balance, right?
You want to be improving your product, but you still need to do marketing.
And especially as a small team or even a solo founder, somebody who's doing everything,
it's really, really difficult to juggle the two and balance the two in a meaningful way
because so much of the marketing stuff, you do it and it does nothing.
And so it can be really, really defeating and you're like, oh, well, nothing's going
to work.
I've tried five things and nothing's worked.
Well, you just haven't found the one that will work.
And a lot of them too, it's not just whether or not they will or won't work.
It takes time to get them to work, right?
To build a following and do things that are of interest to people.
And I mean, a lot of it too, I think probably one of the biggest mistakes people make is
just the mindset, like developers are so, we want our products people, I should say,
because it's developers and designers.
We want to believe if we build a great product, people will just talk about it, right?
Like, but you look, even Apple markets, like they spend a lot on marketing, you know, and
they've got some of the highest quality products in the world, whether you like them or not,
like they make good products and they still invest a lot in marketing.
So there's just, it's, you have to juggle both.
You have to spend time on both.
And it can be really hard to do if you're not constantly seeing wins and reassurance
that your time is being well spent earlier, I guess later last year in November, I decided
that I was going to make November, like my month of growth, I'm going to start trying
all these different marketing efforts.
And I kind of burned myself out like posting on every single form that I could find and
doing guest blog posts and getting a newsletters.
And it turned out that only one or two of my efforts really moved the needle at all.
And the rest, it was either never going to work or it was going to be a super long slog
that I was probably going to, to completely burn me out.
And so I kind of decided to focus on just like the big wins, you know, posting on Hacker
News for indie hackers worked really well.
And other than that, going on Reddit or small sub Reddit and getting 200 or 300 page views
for a site that's already getting like 300,000 a month just didn't move the needle at all.
Yeah.
Well, and so I think the other thing too, that as product people, as developers who
aren't marketers fail to think about is they go out and start screaming from the mountaintops
about their product or whatever it is they're working on.
And like marketing isn't about shouting about your product, right?
It's about communicating to people how you can solve their problems.
And so, and I mean, I made this mistake, it took me forever to figure it out.
And it's, it's not rocket science.
Like people have known this for years, you know, professional marketers, but you know,
you're not selling your product, you're selling something to help improve their lives.
If you just go out and say, Hey, look, I built this, come use it, you know, that's not going
to be effective.
You're like, Hey, if you're dealing with this, I have something that can help you.
Here it is.
You know, try it out.
And it's more focused on your customer's problems than, you know, then you're starting to get
into marketing.
Whereas a lot of times people, you know, if you go out there and you just post everywhere
and try different things and you're talking about your product, but you're not talking
about your customers and their problems, then they're like, Oh, well, it didn't work.
And it's like, well, it's not that it doesn't work, it's that you took the wrong approach.
Right.
And I think it's too easy for people to think, Oh, well, I tried it and it didn't work and
not think about, Oh, I did it wrong.
Maybe I should have tried this or I, you know, put more emphasis on my customers instead
of the product.
Yeah.
It's so hard to, I remember doing Y Combinator and hearing people talk about Airbnb a lot
and Airbnb, I don't know if you know, but like there's their whole story is like how
many years they spent totally believing in their product and they were changing it and
tweaking it and iterating, but they were also iterating on their marketing and it got to
the point where I think 99% of people would have quit.
They would have been like, Oh, this is not working.
It's never going to work.
And for some reason they didn't.
And it ended up, you know, being the company that is today, but yeah, finding that balance
between it, am I doing it wrong or have I not been doing it or am I doing it right?
I just haven't been doing it for long enough.
It's just really tricky.
Yeah.
And it was just, I think it just boils down to you've got to have the tenacity to know
that a lot of things aren't going to work and you've just got to keep going until you
find out what does work and it's too easy to give up, uh, early on and say, uh, none
of this works.
I'm, am I focusing on the wrong thing and then give up.
And so much of, so much of it boils down to tenacity.
I think that's kind of the, the toughest thing to explain to people is like, well, just keep
going and they're like, Oh, I don't, I've been going like, well, okay, keep going in
a different direction.
You know, try something different and like try to kind of get outside of your company
comfort zone.
And, you know, it's, it's hard.
It's not, it's definitely not easy.
Otherwise, everybody would be figuring it out, but there's, there's certainly opportunities
out there.
Was there ever a point in developing sifter that you came up against some sort of challenge
that felt insurmountable at the time or any particularly difficult points in sifter's
history?
Um, I mean, you know, there's always difficult points.
I mean, everything from dealing with, uh, fraud, you know, consumed a couple of weeks
of attention, which in hindsight, you know, it cost us a couple hundred bucks of credit
card fees, but that was it, but it consumed me for two weeks.
And so I, you know, it emotionally, it took a toll far beyond what it should have.
Um, in hindsight, I would have just probably been like, okay, whatever, and just dealt
with it and moved on by the biggest thing was at one point without going too much of
the backstory, I screwed up and lost eight hours of customer data when I was trying to
resize some servers and do some things.
And this was when the, the, the architecture was still pretty immature and the database
and everything was on one virtual server.
And uh, I just made a stupid mistake being in a hurry and lost eight hours of customer
data.
We recovered about three hours of it and it was thankfully at a time when there was less
traffic.
So it wasn't as much.
Um, I think we did something like $700 worth of refunds, giving customers that were affected
a free month.
Um, but ultimately everybody was really understanding.
I mean, when it happened and I realized it happened, I was like, crap, this is it.
We're out of business.
It's done.
And, uh, you know, I was like, all right, well, just gotta do what I can and hopefully
we'll pull through.
And, you know, sure enough, we pulled through and, uh, everybody was surprisingly understanding
about it.
Like, you know, I was doing everything I could to help people kind of recover because, you
know, there were notifications for everything.
So theoretically everybody kind of had a backup in their email because of the notifications,
um, or back most of the data.
And you know, it worked out just some refunds.
It was tedious that issuing the refunds was the hardest part just cause it took time.
Um, but ultimately like, uh, I forget all about it all the time.
Like, Oh yeah, that's right.
We had to go through that.
Oh yeah, that happened.
You know, and I guess that the biggest lesson out of that or not really a lesson because
I knew it, the biggest validation out of that was that even when you screw up and make a
really big mistake, like, cause losing data, it doesn't get a whole lot worse than that
with, uh, cloud services and, um, being honest and transparent and, you know, just really
working to help your customers and make life as easy as possible on them.
When you screw up, uh, people are human, they are forgiving.
And as long as they know you care and that you're taking steps to make sure it doesn't
happen again.
Sure.
A couple of customers might leave and not trust you, uh, but by and large, your customers
are going to stand by you.
Um, as long as you're taking care of them and being honest, it's nowhere near as bad
as what you probably imagine it will unfold like now, if you're dishonest and misleading
and then the truth comes out, that can be a problem.
But as long as you're straightforward and transparent, it's, it's a lot less painful
than, than we all probably imagine.
It's basically be, be human and don't, don't be an asshole.
Yeah.
It seems so simple, doesn't it?
But so many companies do not do it.
Yeah, they don't.
And I understand like the psychology behind it because when anything like that happens,
it's like the pit drops out of your stomach and it's, it's scary.
It's all, I mean, I feel terrible if my own website goes down, it doesn't hurt anybody.
Like literally no one's effective.
So sifter went on and it sounds like, aside from a few minor bumps in the road, it was
growing steadily and you ended up selling the business.
Can you tell us about the process of selling the business and, and I know that since you
sold it, there's a little bit of a, you know, an aura of secrecy when it comes to the numbers
and stuff.
Aura.
That's, that's just, that's, that's up to JD now.
I think he's, he's, he's approved me sharing that it was a kind of low six figures, um,
but healthy enough.
So you know, people can, can use their imaginations, but, um, uh, yeah, so it was doing well.
I mean, I, you know, it was making a comfortable living from it.
Um, but I had business wise, um, everything was, was great.
I think, so I, I had, I spent the last three years dealing with leg issues and foot issues.
As you know, I, at the time I decided to sell, I didn't know for sure that I was going to
end up amputating, but it was still a very feasible, um, thing.
And between all of those medical issues and the ups and downs, the recurring revenue was
fantastic and made it very, very easy, um, to focus on health issues because sifter still
maintained and went on, um, and did just fine.
I, you know, could keep up with support, but it was harder to stay on top of new development
and things like that just between all the surgeries and downtime and recovery and physical
therapy and doctor's appointments and all of that stuff.
And so the business was great in that fact or in that, that respect.
But by the time it was all starting to wind down and I felt like I had it under control,
I was just exhausted from trying to juggle it all.
Um, I didn't want to be running a business anymore.
Um, you know, loved aspects of it, but, uh, the foot stuff took so much out of me and
I wanted to kind of just step back and just reset and all of that.
And so decided to sell it, um, and I'd been thinking about it for a while through the
medical issues, but, um, at that point it was just kind of good timing.
Uh, Patrick McKenzie had just sold bingo card creator.
And so I asked him about that and, um, he said great things about FE international.
I was like, wait a minute, so I can actually sell the business.
Okay.
It's realistic.
Let's give it a shot.
And so I did, and I think that was probably one of the key things, um, and then joined
wild a bit and have been working on, uh, on that stuff and it's been great.
Tell me, tell me about wild bit because I wasn't familiar with well, but until I kind
of started reading more about you and sifter a couple of months ago, and we talked a little
bit about it before, before the show, and you mentioned how much you liked their culture.
So what is wild bit?
What is it like working?
Yeah.
So wild bit is they, we make beanstalk was the first product, uh, which launched, I'm
going to say 2007 ish that's all right.
No, it was before that.
I don't know back then.
Uh, then they launched postmark and then deploy bot and I say they, cause when they launched,
I wasn't there, but, uh, sifter used postmark and it was literally like out of every product
we paid for postmark was the one I just, I loved giving them money because they just
did such a great job with the product.
Um, and so I over the years had talked to them a lot and interacted with them sifter
integrated with beanstalk.
So I'd worked with, uh, them from a development standpoint to get the integration and all
the kinks worked out.
And it was just one of those things where over time, working with them, interacting
with them, and just really admired how they did things and got to know them better.
And kind of when it came around that I was thinking about selling sifter, I mentioned
it to them in passing.
And we just started the conversation was like, well, why don't you come here?
I was like, well, I don't know if I'm really going to sell it yet.
And so we decided it made sense and, uh, went and joined them.
And a lot of the reasoning was a lot of the reasons I wanted to sell sifter and not run
a business after, after all this stuff was that I wanted to take a step back, be able
to spend more time with the family, go on vacations without worrying about or being
on call and that kind of stuff.
And wild bits culture is very family focused, not just family friendly or family accommodating,
but family focused.
And it's not just writing on the website.
Like it's really kind of the way we do things, um, you know, half the teams remote.
We've got 26 people are more than half the teams remote now, I think.
And it's, it's just a really welcoming environment.
Uh, you know, when the teams in Philly or member team members are in Philly traveling,
uh, to the, to the pain office, like they get, everybody gets together, not just for
like a team happy hour, but like everybody's spouses and children come and the kids all
play together and like, it's just, it's just more of like a small family friendly setup
that, uh, you know, it just works, right?
It meshes with kind of where I'm at.
Sounds like, uh, the exact opposite of, uh, Silicon Valley typical program, almost, almost
by design.
I mean, yeah, I don't know.
I mean, I would say that there's probably a lot more in common with, uh, the base camp
crew and mentality than, uh, with Silicon Valley for sure.
Right.
We're going to have some of our own opinions on things too, but for the most part, yeah,
it's, you know, it's, we don't want to, we don't believe in working crazy hours, right?
If, if it's a long day and you're exhausted and your brain's just not firing anymore,
don't sit at your desk, go home.
If you're working on something and you feel like you need to finish it and it's not like
critical, quit working on it and go home, spend time with your family, that kind of
thing.
Like I was literally in Slack with Natalie, our CEO the other day, and, uh, she just randomly
sent me a picture of her daughter asleep in the crib and it was her daughter's birthday
and our two youngest are about the same age, uh, as well.
And she's like, Hey, I'm just going to take the rest of the day off and go spend it with
my daughter on her birthday.
I'm like, awesome.
Cool.
Have fun.
You know?
And so it's not just like, we don't just talk about it.
Like everybody kind of does it and it's embraced and encouraged.
Like as long as you're not holding anybody up and nobody's depending on you, we really
kind of work to make sure that that's rarely the case.
You can go do that.
Right?
Like, you know, take, take a half a day and go spend it with your family or whatever.
So without people thinking that, Oh, that guy's lazy.
So that's the other thing too.
Right?
Like a lot of companies, you know, they'll say that, but then if you do it, especially
well, so there's the remote policy, right?
Like a lot of companies are quote unquote remote friendly, but then the people who are
in headquarters look down on the people who are remote, like, Oh, they're probably not
working or, you know, whatever.
They're just home goofing off.
Or you know, in that case, like if somebody's like, Oh, I've got to go take care of my
kid.
It's like, Oh, whatever.
They never, they're not committed.
They're hard.
Um, but the reality is when you let people feel comfortable doing that kind of stuff
and taking care of the things they need to take care of, then when they're working, they're
more focused on work.
They're not distracted or stressed out by things that are going on in their personal
lives.
And it just makes for a healthier environment.
And it's, you know, it's something that Wildbit gets intrinsically and Natalie and Chris,
uh, they've talked about, you know, in a large part, they feel like it kind of happened.
They always, you know, felt that way, but having kids kind of helped them see that and
realize that.
And so by virtue of that, like it's kind of just extended and the whole company embraces
it.
And it's just, it's cool that way.
Like it's one of those things that it's in hindsight.
It's like, why is this so rare?
Like this is like a much healthier way to run a business.
Why do more companies not embrace this?
Yeah.
My girlfriend tells me all the time that she's like, all you tech people or you guys are
all just, uh, she calls us producers who are obsessed with productivity and we're the types
of people who might, you know, tend to push ourselves to, to work 16 hours a day.
And so we tend to create cultures that glorify that, you know, uh, going back to one of the
things you were saying about selling sifter, you're talking about it being a SaaS business
with monthly recurring revenue and how that helped you, uh, through the period where you
were dealing with your leg.
And that really reminds me of, of the topic of, uh, of passive income in general, which
I think is such an attractive idea that it's, it's, it might be the main reason why a lot
of people decide to become, as I call them, ND hackers and, and start web applications
that charge monthly recurring revenue.
And for those who don't know what passive income is, which is probably nobody, but,
uh, it's, it's the idea that you build a product that's, it's a moneymaking machine, right?
It makes money when you're asleep and makes money when you're shopping for groceries.
And so you're not trading hours for work or trading, uh, trading hours of your life for
dollars, but instead you, you build something that brings in dollars on its own.
Having talked to, I think 92 founders now at this point, passive income seems almost
illusory to me.
Uh, there's very few businesses that I've talked to you where the founders aren't either
a working to grow their companies or, you know, be running a company where if they were
to leave the income would just completely drop.
Have you ever seen a truly passive business?
Um, I mean, I'm sure they're out there and I mean, for me personally, I feel like a truly
passive business, it would be boring, right?
Like we want to create things you want to challenge and this isn't just people just
human nature, right?
Like if you're not challenged in some way, you know, we don't, we don't grow like that's
how we grow.
And so a purely passive business to me, it's kind of like a perpetual motion machine, right?
There's probably things that are really, really close, but technically it's just, it's not
possible.
Um, it's a nice thing to have.
Um, it certainly helped with all my recovery and my leg and all of that.
But I think the other thing is people think that it's, it's, it's maybe too glorified
now or too magical and it's hard to lose passive income, but it's hard to grow passive income
too.
Right.
Right.
You've got to create, you've got to justify that person or that business giving you money
month after month after month.
And SAS is a nice model for that.
Uh, but at the same time, you know, you have to justify them to them every month.
You have to kind of keep up your end of the bargain.
And so with SAS churns going to kick in, it's going to fade away.
Um, if you aren't maintaining it, you aren't taking care of your customers, that kind of
thing.
I think the biggest thing though is no, I think the biggest thing is just people think,
oh, well it's, it's, it's this holy grail and it's glorified and think, oh, well, if
I, you know, made X thousand a month, I'd be, you know, all set.
But the thing is you just, you don't just jump to, I mean, some businesses I'm sure
do, uh, but you don't just jump to, you know, $20,000 a month or whatever it is overnight.
Like you get there slowly.
And I think the biggest problem, at least listening to people who are frustrated and
having gotten there, it's just that this, that it happens overnight and it doesn't like
gail Goodman of constant contact had a great, great, great talk at a business of software.
And it's out there.
If you just Google gail Goodman business of software and it talks about constant contact
and they're slow, I forget the exact title, but it's like the long, slow SAS ramp of death.
And it's because when you're talking about recurring revenue, it grows slowly and steadily.
And it's a slog.
You've got to keep working and that's not attractive to people, right?
To know that it's going to take years and years to achieve success.
So you know, then there's people like Nathan who grow convert kit from to $5 million like
he did so quickly, but nobody's been talking about the two years he spent working on it
before that.
Right.
Exactly.
Yeah.
He's got a really awesome story that I hope to get him on the podcast or for an interview
for Andy hackers, but he spent a lot, I think his goal was to get $5,000 in five months
and he only got to two and a half thousand and should have quit, right?
Yeah.
Can you imagine, uh, like now he's making, you know, convert kids bringing in 5 million
a year, I think, or that's the, that's the run rate maybe, um, you know, and he could
have given up and that's the thing, you know, it's, yeah, it's just, it's mind blowing to
me that something can be going so slow and it's so tempting to give up and that you could
have missed out on that opportunity because you didn't necessarily want to stick with
it.
Or maybe there was another thing you thought might be a better bet or whatever it was almost
every business story that I've read from like Virgin, right now I'm reading, um, Nike's
book or the Nike, uh, what's the title?
I don't know.
It's about the founding of Nike.
Every major company got to be major.
They went through some shit, sorry, language, um, they didn't just, it wasn't just an easy
thing.
Like they really, like the things they went through where, you know, and you're not talking,
you know, $10,000 here or there, you're talking millions or, you know, hundreds of millions
of dollars.
You don't get to be that big without having kind of a handful of those bet it all moments.
And you know, you read those stories and you see the kind of scary decisions they have
to make.
And I know like the more I've read it, the more I'm like, I don't ever want a big company
like that.
That's the kind of decision.
Like that's stressful.
Like, how is that enjoyable or fun?
And you really have to have that type of personality.
That's like, I don't care.
I'm just going to deal with it and push through it and fight through it.
It's not as easy as we all want to believe, but yeah, the more stories you read like that,
the more you find out how, just how hard it was for all these big companies to achieve
what they've achieved.
One of the things that I've thought a lot about since starting indie hackers and talking
to all these people is, is in the future, assuming I launched other ideas is trying
to avoid putting myself in a situation where I think that, you know, I might fail.
So that means doing things like having a really quick MVP where I can validate my idea and
two to three days, you know, a week or two tops rather than having something that takes
months to get out the door, you know, doing it the way that you did it, I think is really
smart and really awesome.
And I've got this at this point, like a checklist of all the different things that I would run
my ideas through before I decide to work on anything just to minimize that chance, even
if it means giving up on, you know, maybe a potentially riskier but better idea that
can make more money.
Well, and then the catch there is you run the chance of over analyzing your idea to
death and then giving up on it before you even try it.
That's very true.
So it works both ways.
It all does.
It's you're constantly towing the line.
Yeah, I've got like this list of 100 ideas now and I probably add like one or two ideas
to it every week and it's it's more for me a process of like, I'm sure there's a lot
of ideas on there that could work if I put the effort into it.
And it's it's me it's just like filtering down to like one or two that I have time for.
Speaking of this, you are now running a website called starting and sustaining, where you
talk all about starting building and launching online businesses and bootstraps SaaS applications
and you do interviews with founders.
Can you tell us a little bit about you know, what got you into that when you started it?
And what your goals are?
Yeah, so I wrote a book about it about five years into sifter and a lot of that was driven
by there's a lot of talk about starting a business, but it's really easy to launch something
like it doesn't become difficult until you're hanging on for five years and really kind
of trudging along if the business isn't growing and like things you're trying aren't working
and nothing's improving it.
That's when it gets hard, right?
Like anybody can announce something, launch it, build it.
It's far fewer people stick with it.
And so I really wanted to kind of talk about that and say get past like, yeah, talk a little
bit about launching and stuff, but really wanted to get past that and talk about how
do you stick with it?
You know what happens when you have to deal with fraud and chargebacks and you know, you
got into this to build software, but you're spending most of your time running your business
or dealing with support or whatever.
And kind of in a way helping people see into the future and see kind of what things were
going to look like and understand, you know, I guess in some ways help them understand
if that's really what they want to do.
And in other ways, if it is what they want to do, help them know what's coming and how
to avoid it and how to, you know, not make mistakes, some of the common, easy mistakes.
And so I wrote that and then after going through all of my medical stuff and then selling sifter,
selling in particular, you know, when you go through due diligence and you're looking
at your business through somebody else's eyes, you start to see a lot of things.
And you know, you go through the, a lot of the, am I going to regret this?
Is this the right thing?
What would I have done differently?
What should I have done differently?
And so the more I did that and went through the process of selling the business, I obviously
learned how to sell, you know, a small SaaS business.
But I also saw a lot more of the mistakes that I made and what I should have done differently.
And I felt like I need to write this up.
You know, this needs to be out there for other people so they can save themselves from all
the mistakes I made.
I mean, I know if I were to go back and do it all over again right now, sifter would
probably turn out a lot better or whatever I built would have turned out better.
I just would have made better decisions.
It would have been less painful.
I would have enjoyed it more.
There's just so many decisions in particular that you think you would do differently.
Yeah, there's countless.
All right.
The, I mean the two biggest ones are well, there's so many.
One of the biggest mistakes was one that I knew, but I felt like I was doing a good enough
job and that's talking to customers.
There was no shortage of feature requests for sifter.
People did a lot and that, you know, really helpful, useful feature requests.
I implemented a lot of them, but there were a lot more that I just philosophically didn't
totally buy into.
And I spent so much time talking to people via email that I thought that was a good enough
proxy for understanding our customers, our target customers.
But in hindsight, like getting on the phone and talking to people was a totally different
story.
You can find out different things, things that are small enough that somebody's not
going to take the time to email you about.
If you're having a phone call with them, they'll take the time to dive into it and explain
and you're like, Oh, I can fix that in five seconds and do a release.
You know, there's just a lot more understanding and insight.
So I didn't do a good enough job talking to customers because I felt that email was a
good enough proxy for that.
And in hindsight, that was definitely, you know, that was wrong, completely wrong.
I talked to Josh Pickford of Bear Metrics recently and he said almost verbatim the exact
same thing about how he would talk to people over email and they would give him like, you
know, a limited amount of feedback and he felt pretty good about it.
And then he started as part of his sales process is talking to people on the phone and just
something about about being able to talk and being kind of unfiltered.
And maybe, you know, there's something about like the over email, you can think about exactly
what you're going to say.
But in a conversation, it's kind of like there's pressure when there's a silence to say whatever's
on your mind.
And people just reveal a lot more about about their actual thoughts and opinions and their
needs over the phone.
So that sounds like like really good advice that's pretty consistent for anyone who's
got customers.
Yeah.
And the thing is to getting on the phone and talking to people is simultaneously sales
and research and especially for those first customers and you're trying to validate and
figure out and kind of shift what you focus on.
It's just, it's priceless and on every way in relation to the business.
So it's just so, so valuable an email or any kind of text based chat or whatever.
It's not enough.
Like get on the phone with people.
If you can meet with people in person, to me, that's kind of the key.
That's the heart of it all really.
Which once you've gone through it, you know, and you hear people say it, you're like, yeah,
yeah, yeah, okay, whatever.
You know, but once you go through it and you look back, it's like, golly, you know, um,
like a whole categories of advice that like on their surface, they just get repeated so
often and they seem so basic, like talk to customers, make something people want.
And people are just like, ah, yeah, yeah, of course I'm going to do that.
And then they, they don't understand like the, like how amazing that advice is.
If you actually take it really seriously, I think it's, it's just people probably they're
like, that's so simple.
It's too simple.
Deceptively simple.
Yeah.
Deceptively simple.
Exactly.
Um, even with just like a product design stuff, just the basic user interface stuff, you're
always relying on assumptions and you go into a coffee shop and you ask someone to use stuff
like I've never ever built something and then shown it to people and not been surprised
by the way that they use it or their feedback.
There's always going to be things that people do that break your assumptions.
Yeah.
As a designer or, you know, building any software, there's very little substitute for watching
somebody struggle through your brilliantly crafted interface and then realize just how
not brilliant we all are.
And then, so there's one other thing too, that I think in hindsight, I miss the boat
on and it's a tough one to get right.
And that's automation.
You don't want to automate something too early, but if you wait too long to automate something,
you're wasting your time.
And this is something that I've spent a whole lot more time thinking about and in the heat
of everything, I looked at automation as does it save me time?
And if so, is the amount of time it would take me to automate it less than the time
I just kept it very simple, right?
Can I save myself time by spending a day working on this now?
And in hindsight, that was a really, really naive perspective because when you automate
something and with software, there's plenty that you can automate.
I mean, endless, endless options.
You're not just saving yourself time and it's, you're not just saving yourself the 30 seconds
it takes to perform the task.
And so like one of the examples I use for this is trial extensions.
People had to email in to ask for a trial extension if they signed up over the holidays
and didn't get a chance to try it out.
You know, if they, if that was the case and they hadn't created any issues in their account,
they don't need to email me for a trial extension sifter.
I could have written logic that would have been smart enough to say, Oh, they haven't
created any issues.
Give them, you know, sure.
Give them some more time.
Let them extend their own trial.
On the surface.
I was like, Oh, well, it's easy.
I just click a button, but I wasn't factoring in that, you know, inconvenience for customers,
you know, for them to write an email versus for them to click a button for themselves.
Like that's a huge win for customers.
It's not just about me and saving me time.
Yes, I get to save time, but that's almost a bonus at that point.
And there's a lot of tasks like that, that there's almost a progression for automation
that I see now, you know, kind of first you just do it totally manually until it hurts.
And then you automate it a little bit to make it a little less painful for you to the point
where you kind of slide all the way down the spectrum to where customers can do it themselves
without asking you for anything.
So like imports and exports is another thing.
Like at first you might do things manually like that for customers, and then you might
open those tools up to customers, let them do it themselves.
And then in some cases you can even completely automate it, you know, just have the system
be smart enough to recognize situations and handle it proactively.
And the other huge bonus to all of that, and this is part of the reason that it really
got me thinking about automation was when you go to sell a business or when you go to
train somebody else to do a certain role, the more automation you have in place, the
less painful that is because when you sell a business, you have to teach another team
how to run the business the way you do.
And the more things are automated, the less you have to teach.
And the simpler that process is, the more attractive the business is, the higher evaluation
you're going to get because they're not going to be like, Oh, this is going to be really
painful for us to do.
And if you, you know, even if you don't ever sell the business, eventually you're probably
going to hire somebody to help you.
And by having that stuff automated, it's trivial to train them because now they're, you know,
they've got all the stuff they need already there in place and you can focus on the things
you need to focus on.
So it's one of those things.
It's just an all around when you don't want to just arbitrarily automate everything.
But if you're mindful and looking for those opportunities, it can really, really, really
make a difference in how you run the business and how much you enjoy running the business.
The other thing too, depending on the type of task, like there are a lot of things for
me that will be like 30 second tasks.
But anything that's like 30 seconds, once you're at 30 seconds or a minute, you've,
you've got some context switching costs in there too, right?
So like, it's basically 10 minutes.
Yeah, it's, it's basically 10 minutes or even longer if you get distracted because you're
switching apps or whatever and you get sidetracked by Twitter or whatever email, then who knows
it could be 30 minutes, right?
So like the cost isn't ever simply how long does it, let me time myself performing this
task.
So there's a lot of risk in losing time by distraction.
Yeah, that's the worst for me, by the way, Twitter, because one of the tasks of my weekly,
weekly to-do list is, is, you know, tweet, I need to be sending out tweets every day.
And inevitably like I go to send out a tweet and I just read tweets for like an hour.
One of the things that I've noticed about like, I think it's interesting about your,
your starting and sustaining book in your, in your blog is really that you're giving all sorts
of advice.
It's based on your experience and based on things that you've learned and I have a question
for you.
Is there any particular, is there anything that, that any books or movements or philosophies
that you find particularly true or compelling?
About development and business or just, yeah, about like, about entrepreneurship specific.
Yeah.
Um, you know, for me it's more, it's kind of two things.
One it's that drawing a lot of inspiration from what other people are doing, trying to,
you know, just like I'm trying to share things so that other people don't make the dumb mistakes
I made, um, trying to, you know, learn from everybody else's mistakes and what they figured
out over time.
Uh, but at the same time kind of trying to pull it all together and synthesize it into
something that feels right for me and that, you know, that I'm comfortable and happy with.
So you know, there's countless influences, uh, um, you know, there's, there's tons and
tons of people.
And the more people I interact with, the more I learn and figure out.
And uh, there's just so many people that have a lot of great insight and wisdom that it's
kind of hard to point to one place and say, this person, they're, they're my, you know,
they're the wind beneath my wings.
Um, but there's not just different sources, but opposing sources, right?
So you know, I'm very much kind of in, you know, most of the people I know of bootstrapped
their apps and, you know, talked to a lot of people about bootstrapping extensively,
but I've also made a point to try and talk to people who've raised money and the pros
and cons and to read about, you know, the opinions of people who've raised money, what
they regret, you know, whether they were happy with it, um, you know, that kind of thing.
So that I have some context and kind of understand and can form a stronger opinion about why
I, you know, feel the way I do about different topics.
Yeah.
It makes a lot of sense.
I think, uh, the worst thing that anyone can do is, is to make decisions without being
aware that they're making them or without being aware of like why they're making them.
Yeah, absolutely.
And on that note, I'd like to ask, is there any advice that you have in particular for
aspiring entrepreneurs, people who are starting their businesses or mistakes that you see
people making often, um, beyond the stuff that we've already covered.
I'm not sure.
I mean, I would say kind of two things and these are more of my personal things that
they may not be super relevant for others, but I feel like they, they probably are.
One is to, uh, before doing it, make sure you know that you want to start a business.
I feel like too many people and now I know better and understand, but I feel like I wanted
to start a business because I wanted to start a business and sifter kind of happened, but
I knew someday I wanted to start a business.
I just didn't want to do it then.
So really make sure you want to start a business, understand what it means to start a business.
Don't just start a business because that's what everybody's doing and that's what you
feel like you have to do.
Um, and then the other thing is kind of an extension of that, which is to, that's the
best way.
And this kind of goes back to the philosophies emerging of start a business your way, right?
Like there's too many stories out there where people are sharing what worked for them.
And I feel like people see that and then, oh, I'm going to do that, but it doesn't always
work.
And I think it just would help for people to go, I want to blaze my own trail.
And so focus more on do what works for you.
Don't try to copy what other people have done, learn from other people, you know, see what
they've done, but then factor that into your decision making.
Don't just let that be the decision.
Cool.
I think that is excellent advice.
And on that note, I think it's a, it's pretty good place for us to stop.
Can you tell everybody where they can go to read more about yourself and what you're working
on now?
Um, yeah, so Garrett diamond.com with two R's, two T's, D I M O N dot com and starting
and sustaining.com, which, uh, right now it's a medium site, but it's going to be a little
more ambitious here in the near future, um, with the podcast and, uh, the second edition
of the book.
Cause I start kind of working on that in the open, hopefully in the next couple of weeks.
Awesome.
Thanks for, thanks for coming on the show and hopefully I can talk to you again on the
teacher at some point.
Yeah, of course.
Thanks for having me.
If you enjoyed this episode of the Andy hackers podcast, you should join Garrett and me on
the Andy hackers forum, where we'll be discussing this episode, our conversation and answering
your questions too.
Just visit www dot Andy hackers.com slash forum.
Thanks and see you guys next time.