Software Social

Colleen and Aaron gave their workshop at RailsConf! Well, a version of it.

Show Notes

Huge thanks to all of our listeners who’ve become Software Socialites and support our show! You can become a supporter for $10 a month or $100 a year at

What is Software Social?

Two indie SaaS founders—one just getting off the ground, and one with an established profitable business—invite you to join their weekly chats.

Michele: Hey Colleen.

Colleen: Hey, Michelle.

Michele: Hey Aaron.

Aaron: Hey, Michelle.

Michele: Aaron is this first
time, you've actually like,

come on here, with me here.

Like I

Aaron: Yeah.

I've heard the last, yeah, the last two
or three weeks, y'all have said my name

a whole lot and I've wanted to talk
back, but yeah, this is the first time.

Michele: That's how I feel when I'm
listening to the hammer stone podcasts.

Like I was listening to it while
I was working the other day.

And like, there's something she's
like, Michelle had this great idea.

And I was like, Ooh, I had a great idea.

Like, um, so we are all
at the edge of our seats.

How did it go at rails?

Colleen: Well, what is
Aaron's favorite phrase?

Not ideal.

He says that a lot.

It was not ideal.

Aaron: It was definitely not ideal.

Michele: Oh, no.

Colleen: I've picked that up from
Aaron which is, I feel like a

phrase, that you can, um, co-op to
me, not terrible, but not perfect.

Michele: Let's, uh,
let's get detailed here.

In what ways was it not.

Colleen: So, as we had talked about, I
think on the last episode we did together,

I had built the workshop in such a way
where you had the stepped branches.

So the idea was they would check
out a branch, they would do the

work, they would get the solution.

And I thought I was quite clever
by getting the cloud IDE set up

on git pod, which was wonderful.

And Aaron and I get up there and there
must've been 180 people in that room.


Michele: Well.

Colleen: Yeah, it was.

Aaron: It was huge.

Colleen: People were sitting on the
floor, they were standing on the walls.

Michele: Dude, sold-out crowd.

Colleen: It was a sold-out crowd.

And we get up there and we started strong
cause I had made some slides beforehand.

So I had plenty of slides like before
the workshop was like the intro.

I feel like we started really strong.

And then we get to the part where they
have to open the repo and git pod.

And there was no internet.

Like The wifi just
straight up did not work.

Michele: Wait, so it like, had it been
working the rest of the conference and

then it died at this point, or like,
had it been spotty the whole time as

conference wifi kind of tends to be.

Colleen: I have no idea.

Aaron: It was working fine
when no one was in the room.

So when we were in the room beforehand,
we were getting Colleen's computers

set up and it was working just fine.

And then when it was time to do it live,
not only would it not work for other

people, it wouldn't work for Colleen.

Colleen: Oh, right.

Aaron: Colleen's up there telling
everyone to go to git pod and

she's trying to do the same thing.

And meanwhile, I'm like standing
off to the side and watching her

computer and it is not loading.

Like not even slow, it's
just not loading at all.

Michele: So, what did you do?


Colleen: So what did we do?

So it was good.

We were there together because.

Michele: Moral support

Colleen: I was about to just be like,
okay, we're done, throw up your hands.

I wasn't really, but I did cross
my mind for a minute and Aaron

was like, we just have to keep.

He's like, we're just going to keep going.

We're just not going to do the exercises.

Aaron: Somebody from the
audience shouted, do it live.

Colleen: That's right.

So it was super, I had it locally
and I was eventually able to get

it up and running mostly locally.

So I basically, our two hour workshop
turned into An hour long talk.

Um, It was not good.

Aaron: An hour long improv

Colleen: Improv with live coding.


Aaron: With live coding, because
suddenly, at one point, Colleen was

like, okay, so now do this and we'll
give you 10 minutes to do this part.

And I said, no, we got to keep
moving that, nobody has it open.

We can't give them 10
minutes to do anything.

Cause people are just going to leave.

There's nothing for them to do.

And people are just going to leave.

And so I kept saying to Colleen, while
I'm miced so everyone can hear it.


I kept saying, Nope, keep going.


Forget about it.

Keep moving.


Move on.

Just move on.

Michele: Is there a video.

Aaron: What I was saying.

No praise the Lord, no.

Michele: Not ideal for those of
us who would like to relive this.

Aaron: Not ideal.

Michele: God.

I mean, did you like, could you get a
person from the conference in and be

Colleen: Dude, Get this.



Michele: I have wifi?

Colleen: The person who was supposed
to be overseeing the workshop track,

just, I don't know the details, but
he didn't show up to the conference.

So we didn't have like an advocate.

So Ernesto was giving a
workshop in the room next door.

So in the middle of his workshop,
he got on the speaker slack and

was like, we can't do anything.

The wifi is out.

We cannot like no one can upgrade rails.

So he tried to reach out in the
middle of his workshop, but like

no one was able to do anything.


Michele: Ah.

Colleen: It was, it was really.

I told Aaron so after it happened,
I was really mad and I was like,

I'm gonna give myself 24 hours to be
pissed and then I'm gonna let it go.

Clearly retelling you the story right now.

I haven't quite let it go.

Michele: I think that's
understandable, cause you have

been working on this for months.

Colleen: Work Michelle, right.

The other thing that was really cool is,
the interesting thing about Aaron and

I having a business together is like,
we know each other pretty well, but we

have not been to a conference together.

We've never tried to speak together
before, so you didn't really

know how that was going to go.

It was going really well.

We had, I feel like, we
were doing really good.

It felt like very natural and
like, it felt really good.

And then we got to that point and
it was just like, oh, I just felt

like the whole thing was ruined.

So yeah.

Michele: God.

I mean, so like, how did the
people in the workshop react to it?

What did they say about the workshop
afterwards or while it was going on?

Colleen: Well actually people
were really gracious and kind.

Several people, even we were having
dinner that night and some guy stopped

by us at the dinner table and was
like, was he the audio guy, Aaron?

Didn't he say he used to be in theater or

Aaron: Yeah.

He said he used to be like in
audio production for, I think

like proper bands and stuff.

And he stopped by, he was Colleen
and I were eating in the hotel

lobby and he stopped and said,
Hey, I used to do audio production.

I know that stuff goes wrong.

And I've seen people
totally freeze and crumble.

And I just want to say
that you guys did amazing.

I was like, wow, thank you for saying
that because it felt pretty horrible.

That's it, you know, to have people and
he wasn't the only one, but to have people

stop and say, Hey, I just want to tell
you, we were all feeling the pain and

you guys did incredible, like way to go.

So some comfort.

Colleen: Yeah.

A lot of people, no one said anything,
mean like a lot of people were very

kind and said, you know, it was great.

And you did the best you could
with a crappy situation and,

you know, et cetera, et cetera.

Michele: So for all the people
listening, who run developer conferences

with spotty, wifi, Colleen and
Aaron, they just, they are a lock.

They can handle it when
your wifi goes out.

Because, like, honestly, I feel like
the wifi is usually, I feel like

you get thousands of people in one,
like concentration of rooms, all

of them trying to use the internet.

And it very often goes through.

Colleen: Yeah.

And it's kind of a catch 22 because no
one, what I have learned from workshops

of time passed is you can tell people
how to get the stuff locally, but

like almost no one's going to do it.

We had one guy who had it locally.

He sat in the front row.

So I appreciated that.

Aaron: And he was giving us life.

He was the only one that had it and he
was just making eye contact and thumbs

up the whole time we, we relied on.

Michele: You always need
somebody who's sitting in the

front row who's smiling at you.

Like if they're giving any kind of talk
or workshop, that just goes so far.

Colleen: He was great, but I don't know.

I was incredibly frustrated because
you know, the thing about conference

speaking and conference talks
is you're given a stipend that

does not even cover your travel.

You are not paid.

There's a huge opportunity
cost to building these things.

Like it's tremendous.

And as both of, you know, this was time
away from my family, on top of my job,

like on top of my product business,
like it was just, it was just, yeah.


I dunno.

I dunno if the cost benefit analysis of
this, if the benefit was worth the cost.

Michele: Did you guys sell anything?

Did you wait, hold on, did you get the,
the pre-order landing page up before

the conference that we talked about?

Oh, okay.

Did you sell it?

Colleen: No.

Well, let me tell you.

Michele: Okay.

Colleen: No, we didn't sell
anything at the conference.

Michele: Okay.

You're burying a lead here.

Like I feel like there's
something else behind this.

You just sitting there sipping your
seltzer, like just looking at me.

Colleen: I don't know.


We have sold two licenses to presales
since we have gotten back yes, to rails.

Michele: Are they from
people you knew previous.

Colleen: One person.

I know one person I don't know at all.

Michele: money.

Colleen: Yes.

Michele: Strange or money.

Colleen: And Michelle, what I wanted
to talk to you about, as well, as

aaron and I, while we were at rails
conf, we had a big talk about sales.

Cause last time you and I talked, we
talked, you were like, okay, marketing

is one thing, but sales is another thing.

So we had a big talk about
how we're going to be making a

sales push going forward here.

Michele: So what are you going to do?

What does that look like?

Aaron: Uh, We're going to ask.

We, I mean, I, I think it was
good, Colleen and I had many

talks after our terrific workshop.

Um, and I think it was good cause I
think we've both realized that we're

kind of hiding behind, I think first
maybe development and then marketing.

Because with marketing, you can just
like, oh, I'm going to, you know,

do a landing page and send an email.

And I never really have
to talk to anybody.

And that feels like progress, right?

That feels like I'm doing marketing.

I'm so proud of myself.

Which is good.

But I think one step further is we've
decided the only thing that matters

is sales and the only way to do that
is to talk to people, one-on-one and

I think there's been some, like maybe
fear on both of our parts about doing

that, but the new plan is reach out.

We have this whole list of people and,
you know, we've been sending them an email

being like, Hey, come buy the thing that
you don't really know anything about.

And the new strategy is to email them
one by one and say, the thing is.

Do you want to buy it?

Do you want to get on a call?

Let's get on a call.

Do you want to buy it?


Why not?

Tell me why not.

Let's figure this out.

So we had this, you know, emotional
awakening, and then at rails

conf, we did, we did one of those.

We, tracked down well Colleen tracks
down a guy who was like, I think

I'm kind of interested in this.

And Colleen was like, okay,
I'm going to freaking do this.

And we're like followed him
around and finally found him.

Colleen: I did in fact follow him.

Thanks Andy, if you're
listening, I appreciate you.

Chase this guy around.

He was like casually interested and
I was like, all right, let's talk.


So I chased him down and we gave
him a demo slash sales pitch.

Michele: Nice.

Colleen: No.

Michele: He didn't Oh, he didn't buy


Aaron: It didn't not go well.

Michele: Better than the workshop?

Did the wifi work?

Colleen: Than the workshop.

Michele: I feel like that's
the, that's the bar now?

Like did the wifi work
when you gave the demo?

Anything from there is gravy.

Colleen: Right.

Like I was telling Aaron, I
think now that we're a little

bit removed from the workshop.

It's good, that that happened because
if the workshop had been awesome, that

would have been our win and we would
have been like, Oh, we're so great.

We just gave this kick-ass workshop
when reality would be, we still

wouldn't have had sold any licenses.


Like the goal here is so, so I think
the workshop not going so well, forced

us to sit down and like, reevaluate.

Like what do we do?

W what are we doing?

Are we going to do this?

Are we just going to do
all these other things?

What is it?

It's the James clear thing
work versus we action versus

Michele: versus motion, right?


Like what, like what feels like a
sort of you're doing things, but

then what is actually productive
towards doing it, I guess motion is.

Aaron: Motion versus

Michele: action.

Aaron: I think.

Colleen: Anyway, you know

Michele: Yeah.


Yeah, it sounds like it was
like, the workshop was almost

like a productive failure.

Aaron: Yes, absolutely.

Colleen: it was good.

Michele: It was kind of, I don't know
if you guys recorded this after you came

back or what, but I feel like you guys
were talking on the Hammerson podcast

recently about, this kind of like
marketing and sales thing and how like,

Aaron, I mean, I think marketing is in
your job title if I remember correctly.

Aaron: It is.

Michele: So, and like this kind
of like shift from, from marketing

to, to sales which is, it's
kind of like a big shift, right.

And how you're thinking
about selling this.

Aaron: Yeah, it's a big shift for me.

I think I am prone to, one
wanting to develop things, to

wanting to do things in bulk.

And so transitioning to like a one-on-one
sales model is a huge shift for me.

I think it's going to be super valid.

Even the conversation we had with
Andy was really helpful because

he kept saying things that almost
were a surprise to both of us, you

would be so proud of us, Michelle.

We did the whole, we like
customer interviewed and Colleen

asked a question and then tried
to fill some awkward silence.

And I told her.

Colleen: Aaron, like we was
like, stop, I mean, you were.

Aaron: I reached out and put
my hand on her arm and I said,

no, no, no, let him talk.

Michele: It's good to
have an interview partner.


Colleen: It yeah.

Aaron: It was great.

Colleen: I thought that was good.

Aaron: Yeah.

So I think, I think this is going to be
hugely valuable for us one, hopefully,

because we make sales, obviously that
would be goal number one, but it's

also going to make our marketing a
lot better because we're going to know

what, like what words the customers are
using and what pains they actually have.

And Michelle, you probably are
unfamiliar with all of this.

I'm telling you this for the
first time, um, talking to

your customers is a good thing.

Michele: You didn't hear it

from me.

You heard it from Aaron.

Aaron: Yeah, that's Right.


So, and it, I don't emotionally, it feels
better, cause it feels like something new.

It feels like, okay, we can try this
new thing and we can make some progress

because I do feel like we've been in,
I don't know what it has been in motion

a lot, but haven't been making a lot of
progress and this feels like progress.

Michele: Um, I think it's also like,
you know, if you start out on it like a

one-on-one sales model, like you're not
committing to that forever, like, right.

You could do that for a while until,
you know, you get enough feedback

doing this sort of combination
sales, interview type conversations,

which is, you know, pretty common.

You can't dive too deep emotionally,
but you can get a lot of really

good information from it.

But like, you don't
have to do that forever.

You just need to do that until
the point where, you know, you're

growing enough where, you know, the
landing pages have the right words

on them, the pricing model is right.

Like, the delivery that like, you
know, you've kind of ironed out

all of those different barriers
that people have to, to purchasing.

And so like this could be, you know,
a couple of months or six months or

whatever, like it's not forever that
you're going to have to do one-on-one.

Colleen: Right.

Michele: Colleen.

What are you thinking about this
after doing that, I guess also

unsuccessful, but productively
unsuccessful sales demo in the hotel

lobby, what was that like for you?

Colleen: Well, I'm not gonna lie.

What was that?

Last week we were at rails conf.

It was not awesome because we
give the sh crappy workshop and

then Andy's like, yeah, I'm not.

Like he, he liked the product.

He was like, that's cool.

But his need profile didn't match up
with we were trying to sell him, I guess.

And basically the reason that was is
because he has a co-founder and they have

a successful business, and we were leaning
in, one of the things we've been leaning

into is like this concept of, we enable
you as the developer, no longer to have

to write these custom SQL reports that
your marketing, your customer success

team, your co-founder is asking for.

And so, andy we've said his name.

So the person we were discussing this
with is the technical co-founder, and

he made the interesting point that he
was like, you're trying to sell this to

me, but I need to know if my co-founder
is going to be happy with the product.

And so it was interesting.

So it was really

Michele: Oh, because the end user
is actually not the developer.

It's the non-technical or non,
you know, the non-developer right.

Like the like, oh, but it's the developer
who's aware of the problem that they're

annoyed dealing with all of these.

Colleen: Right.

So the developer has the problem
because they have to build the

reports, but the end user of the
product is the non-technical team.

Michele: right?

Colleen: So it's kind of an
interesting, so it was actually a

really useful piece of information.


Michele: I mean, cause you've kinda
talked about this at like the manager,

you know, that like developers don't
necessarily value their time, as

much as they should like, and like,
oh, I could build this in a week.

Whatever right.

You know, we've all seen the, you
know, the thing about Dropbox,

like, oh, this is trivial.

You just spin it up and Linux
and then do these 10 steps.

That'll like take you like
two days and then it's easy.


We also got one of those comments
when we launched you geocodio.

Thank you.

Hacker news.

Um, but like, it's, you know, it's
the manager, who's like, dude, you

cannot spend a week doing that.

Let's just pay for
something, that'll do that.

And so we interestingly like re those
people, especially if, I mean, a

lot of your list is like people who
were at lara conf on like that's the

developers themselves, not their manager.

Colleen: I think as we do more and more
of these one-on-one calls, we're going to

get better exposure to that because, okay.

So I have this experience and like
he's interested, but not totally sold.

But then we get back and
then two people buy it.

So I think people like this
guy we talked to at rails conf

is not our customer right now.

There are people out there who
are excited, who are pre-buying

it before it is even done.

I think we need to lean into those people,
and that's our first set of customers.

Michele: Talk to them first.

Colleen: Right,

Michele: them

Colleen: Right.

Michele: And figure out like, what
is leading them to pre-buy it?

What are those problems?

Who is the decision maker on buying it?

You know, like how did that process
go internally to even say that

they could pre-order it right.

Set up interviews with.

Colleen: Yeah.

So I don't know.

I feel like that was
really good information.

And now we can really dive
into these customer interviews.

Aaron and I have a goal of doing a
call a week and we're going to be more

aggressive about finding those people.

We have 500 people on our email list, so
should be able to have plenty of calls.

Michele: Yeah.

But hold on before we go, we need to thank
our wonderful supporters of this podcast.

I guess I'll do the read today.

I think you did it last time.

Colleen: I did.


Michele: Okay.

So we want to give a huge thanks to
all of our listeners who've become

software socialites and support our show.

You can become a supporter for $10
a month or a hundred dollars a year

at software

Chris, from chipper CI, the
daringly handsome, Kevin Griffin.

I still can't believe
he has me reading that.

But, um, Mike from gently used
domains, Dave from Recut, max of online

or not, Stefan from talk to Stefan,

Brendan Andre of bright bits,
Aaron from Tuple, who is that?

Uh, that sounds like a cool guy.

Maybe we should have him on the show.

Alex Hillman from the tiny MBA, Ramy from, Jane and Benedikt from userlist,

Kendall Morgan, Ruben Gomez of signwell,

Corey Haynes of swipewell,

Mike Wade of crowd sentury,
Nate Ritter of room steals, and

Anna Maste of subscribed sense,

Geoff Roberts from outseta,

Justin Jackson from MegaMaker, Jack
Ellis and Paul Darvis from fathom

analytics, Matthew from appointment
reminder, Andrew Culver at bullet train,

John Koster, Alex of corso
systems, Richard from stunning, Josh,

the annoyingly pragmatic founder,
Ben from consent kit, John from

credo and editorninja, cam Sloan,
Michael Koper of nusii proposals,

Chris from URL box, Caeli from tosslet,
Greg park from traitlab, Adam from

rails autoscale, Lana and Alex of Recapsy,

Joe Masilotti of,

Arvid Kahl, James Sowers of,
Nathan of develop your UX,

Jessica Malnik, Damian Moore of
audio audit podcast checker,

and Elden from nodlestudios.

Thank you so much to all of
our supporters, and Aaron,

Colleen wraps us up for.

Aaron: Thanks for having me on.

Michele: See yah.