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In this episode, we talk with Laura Simpson, the CEO and co-founder of Side Door, a platform that empowers music artists by connecting them directly with venues and audiences. Laura shares her journey from the non-profit world to creating a tech startup that’s making a real impact in the music industry. Discover how Side Door is helping artists perform in unique spaces, build connections, and sustain their careers. This conversation dives into innovation, community, and the future of live music.
LinkedIn Profile - https://www.linkedin.com/in/laurasimpsongraham/
Chapters:
00:00 - Introduction
01:10 - Laura's Background in Non-Profits
02:45 - The Birth of Side Door
04:30 - From Idea to Startup: Laura’s Journey
06:15 - Overcoming Tech Industry Challenges
08:05 - The Importance of Clear Communication
10:00 - Co-founding with Dan: How It All Started
12:25 - Building a Remote Team Across Canada
14:15 - Adapting During the Pandemic
17:05 - The Role of Venture Capital
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Laura Simpson: When I look back on
it, she really invested in technology
early, which I think helped me
not be afraid of technology.
She had, Macs before people had Macs
and then people before her were doing
recording and transcription with the
normal stenographer machine that you
would see in movies and stuff, which
is like a very few character machine.
And she started recording, basically
with a four track cassette recorder with
like multiple mics and stuff like that.
And so she had a realistic recording,
like an actual recording, instead of
just like somebody's interpretation
of what was said and she was able to
really increase the turnaround time,
by just using technology for how long
people were waiting for transcripts.
So she became the biggest in the
Atlantic provinces for her company and
got to travel all over the world with
lawyers and yeah, I grew up, like,
watching her just kick ass, basically.
Raphaël: That's so cool.
Hey folks.
And welcome to this latest
episode of the small tech podcast.
I'm your host Raph co-founder
of EC the digital product
studio, building technologies
for a more sustainable future.
And today we have another amazing guest.
She is the CEO and co-founder of SideDoor.
A platform that brings
together artists, hosts venues.
Everything you need for a musical
performance to come together.
They allow artists and individuals
who want to host a show in their
living room to come together
they also work with venues.
And they have a ticketing platform to
make it all come together into actual
shows that you can pay for to support
the artists in your community or people
who are touring and coming through.
It's a really, really wonderful platform.
And it's doing something that I care
a lot about, which is making the
arts sustainable, making sure that
artists can make a living and continue
to exist and make the cool things
that they do make us feel things
and create stuff that we can enjoy.
She is Laura Simpson.
And I learned a lot about her today,
even though I've known her for a while.
And I think it's really valuable.
So enjoy.
Laura Simpson: Hey, Laura, Hello.
Raphaël: how's it
going?
Laura Simpson: It's going?
great.
How are you doing?
Raphaël: Yeah, I'm doing all right thanks
for joining me on the small tech podcast
Laura Simpson: oh, it's a pleasure.
Raphaël: So kind of just gonna
dive into it, I want to get
a sense of your background.
How did you end up starting Sidedoor?
How did you end up where you were
career wise or life wise, uh,
that led you into this journey?
Laura Simpson: Yeah, I guess I was
like in a mid career crisis where I was
working in a non profit that supported
artists and helped them find funding for
their marketing and touring, in Canada.
And I just found, like, I sort of hit a
wall, both with, like, the advancement of
what I could do in that organization, and
also just feeling like what I was doing
wasn't as effective as I wanted it to be.
I I just found, like, there's
still so many barriers for artists.
That weren't getting acknowledged.
And on the side, I had been working
in live music quite a bit, like doing
all sorts of different kinds of jobs,
whether it's like, um, working at
the local jazz festival, doing artist
services for big artists, or, um, also
just presenting shows in my own house.
Um, so that was sort of my deep
love was to work in live music.
And so that was the main thing
that I knew I wanted to do.
Um, but really it took a trip
to California, which was sort
of my, like, work and parental
sabbatical for four months.
I lived in Los Angeles, um, where I
started to really crystallize things.
And honestly, it still took a
year and a half after that to
really get started with SideDoor.
So it was like this slow evolving process
of just kind of stumbling along until I
came across the right way to do things.
Raphaël: So was it something like
you were, you were aiming for this
or did it just kind of, you knew that
you wanted to help artists, but you
weren't sure exactly what form that
would take or
Laura Simpson: Yeah, the shape of
it was really abstract for a long
time, and I never worked in tech.
Like, I had I mean, basically I had
turned our funding program, that
was paper based into an online,
like, free software based program.
Like, that was the closest thing
I came to, you know, working in
tech, was like, making things more
efficient using free technology.
Raphaël: Yeah.
Laura Simpson: But, yeah, I had no idea
what being a start up would mean, or
raising money, like, I literally went to
Volta, which is our tech incubator here
in town, to hang out and find a developer.
Like, it was a singles bar,
which I always joke about.
I was just kind of, like,
waiting around to meet people
in tech to learn what they did.
But it was, yeah, when I was there,
I was like, oh, you should maybe
join an accelerator program that
will help really give you a break.
Your abstract thoughts, some shape.
So that's what I did.
Raphaël: How, how was that?
What was the
accelerator?
Laura Simpson: It was really good.
It was called Propel, still in existence.
and it was in person in those days.
It's virtual now.
but I found a lot of value in just
kind of being in a cohort of other
founders, knowing that they were
kind of stumbling along as well.
Raphaël: Yeah.
Laura Simpson: And they brought
enough folks in to meet with us.
To give us guidance that helped to
answer some questions in my head.
And some of those people they
brought in actually became our early
investors, which was really nice.
Um,
Raphaël: Awesome.
Was there, what was the most, um, like
surprising or unusual thing when you
sort of stepped into this tech world,
um, coming from, from your background?
Laura Simpson: I found the tech and
business world language really hard.
Like I found people speaking codes
and it's shorthand for them, but I,
especially the acronyms, I still,
Google things while I'm in meetings.
Raphaël: Yeah, totally.
The KPIs and, I don't know, Shred and
all of these
Laura Simpson: All of it.
And it's like, it's like people
want to have a secret language.
So,
Raphaël: Yeah, it's So,
true.
Laura Simpson: you know, I used
to work in journalism where it
was like really beat into us.
Like you need to speak in plain language.
Like I worked in radio.
So it was like, how do you put
things into 30 second bytes?
So that anyone can understand.
So that was the biggest
shift I found, honestly.
Raphaël: Yeah, that background in
journalism, and radio, I mean, that feels,
of course, like, very tied, at least
the radio, to, to music, but journalism,
how does that fit into your way of
thinking and operating in this space.
Laura Simpson: Um, customer discovery
Raphaël: or does it?
Laura Simpson: Customer
discovery is a lot easier
Raphaël: Okay.
Yeah.
Laura Simpson: Like asking strangers
constantly or even our users, just talking
to people really curious and asking good
questions comes really naturally to me.
I have no problem doing that.
So that's really helpful.
And being a journalist kind of means
you're a generalist, so that you
just learn about different things
constantly, and so you have little
bites of experience in different worlds.
And that helps you be empathetic
too when you're approaching
different things, you know?
Yeah.
So it did really help.
Raphaël: Awesome, before Sidedoor,
did you ever, do anything
sort of, uh, entrepreneurial?
Or was this kind of your first
shot at, like, building something,
Laura Simpson: Uh, oh yeah.
Raphaël: or product
or
Laura Simpson: No, no.
I mean, my lemonade stand
Raphaël: ha ha
Laura Simpson: Like really, like I
was in a busy street and I used to go
out at the like time when there was so
much traffic, cause it was just like
a log jam at five o'clock and I sold
loads of lemonade and then I added
different products and stuff like that.
I did that for a long time no, but
seriously, I did, my first real company
was, I started a company right out
of college that was called Document,
which just was sort of pre, would be the
equivalent, ancestry.com, like, so it
was pre that, and so I would interview
people and document, their stories and
their lives, for different purposes,
for like retirements, for memorials, for
you know, all these different occasions.
And I would, I would put it into a
hardcover book and it was sort of
like putting it together with real
pictures and stories and just like kind
of having this like artifact that is
your life at a certain point in time.
And, um, yeah, I did that for a
couple of years and really loved it.
Then I also had an artist services
company right before, side door began.
So that actually is just winding up now.
I, I passed it along to my partner and
she's been running it for this whole
time for I think nine years now.
But she's just at a point where
she's moving on to other things.
And then I also ran an off grid
camp for adults, for two years.
So yeah, I've had a few different
ventures, if you call it.
Raphaël: That's awesome.
So a lemonade stand.
Amazing.
Um, hahaha I love that, so I guess
entrepreneurship and building
things from the ground up has
always been sort of in your DNA.
Laura Simpson: Yeah, my mom,
my mom was a small business owner,
Raphaël: Oh, cool.
Laura Simpson: I worked in
her business growing up.
Her business was in our basement, and
so I learned how to do everything from,
you know, managing their garbage, to
deliveries, to accounting, to, like,
Raphaël: That's so cool.
Laura Simpson: calling on accounts that
were not paid on time, to, like, doing
the actual job of, like, recording and
transcription, which is the company, and,
Raphaël: Oh,
Laura Simpson: yes.
So all sorts of different things.
Raphaël: Interesting.
So also, I guess, working
with audio from an early age.
Laura Simpson: Yeah.
I mean when I look back on it, it
really, like, she really invested
in technology early, which I think
helped me not be afraid of technology.
Um, like, she had, Macs before people
had Macs and then people before her were
doing recording and transcription with
like the normal stenographer machine that
you would see in movies and stuff, which
is like a very few character machine.
And she started recording, basically
with a four track cassette recorder with
like multiple mics and stuff like that.
And so she had a realistic recording,
like an actual recording, instead of
just like somebody's interpretation
of what was said and she was able to
really increase the turnaround time,
by just using technology for how long
people were waiting for transcripts.
So she became the biggest in the
Atlantic provinces for her company and
got to travel all over the world with
lawyers and, um, yeah, I grew up, like,
watching her just kick ass, basically.
Raphaël: That's so cool.
Nice.
Um, so actually you bring
up the Atlantic provinces.
Is there do you find,
okay, so you went to LA.
Were you, did you go basically, from
Halifax to LA and back to Halifax or?
Yeah.
Um, do you find that there's anything,
particular to the Atlantic provinces,
to Halifax that helped you or that made
it like a particularly like suitable
environment for a company like Side Door.
And yeah.
How do you think about the relationship
with LA and the time that you spent there?
Laura Simpson: yeah, I mean, I think
being from the East Coast, we're pretty
necessarily laid back about things.
It just, That's a mindset that I think
some people would think is a deterrent
or a bad thing in business, but I think
it really helps you, not get too anxious
or wound up about things and kind of
ride out the storm a little bit and
the other thing is that it's, you're
naturally, I think, out here curious
and interested in meeting people and
talking to people and really getting to
know them, which I think also makes you
really good at sensing a good vibe and
like understanding how people operate
and honestly, LA had a bit of that.
Like, there was a lot of like checking
out each other's vibes and like, you
know, yeah, like our first investor
in our seed round is definitely like.
we, we got along with really well,
just cause we ended up talking about
music and he's still a big music fan.
And a lot of our investors and
their partners are like that.
Like we get each other, you know?
So I think that's an important thing
that I sort of picked up living out here.
Raphaël: Yeah.
That makes a lot of sense.
Um, so yeah.
Your co founder, Dan, is on
the other side of the country,
Laura Simpson: Yeah.
Raphaël: uh, here in Vancouver.
How did you connect and decide, you
know, let's start this thing together?
Laura Simpson: Yeah, I mean, the
music community is pretty small,
but I did not know Dan before this.
But I do the thing which I still tell
people all the time is a good tactic
is if you have an idea about something,
just keep telling people about it
and eventually it will come true.
Raphaël: I love it.
Laura Simpson: Not that
I'm not working at the same time,
but like, I would tell people
about my desire to do something in
a small DIY shows in that world.
Raphaël: Yeah.
Laura Simpson: And
I had been talking to my friend Rich
O'Coyne, who's a local artist from
here, and he had known that Dan was
working on a house concert network and
so he connected us, it's so funny I'm
telling this because I literally just
saw him at the lake yesterday when we
were streaming, still a small community.
But yeah, he introduced us, actually
when I was still in LA and so we started
corresponding, online just about our
ideas, which were still pretty loose.
And then he was at doing a performance
with the symphony here in Halifax.
And when he was here, we met up and I tell
this story cause it's fun, but like we met
up for brunch at the Lord Nelson and had
a really nice, like, just brainstorming
about what we wanted to see in the world.
Not necessarily like how we could like,
not the shape of it necessarily, but like
what we both desired, like shared values,
shared goals, and that sort of thing.
And we, and we started to
come around to an idea.
And at the end, he's like,
I think we should do this.
Notes And I think you should
be the captain of this ship.
And I was just like, just so
excited, because when I had
thought about it before, it's
scary to think about things alone.
But when you understand that there's
super value in specially somebody
like Dan, who's so well loved in the
community, having his endorsement, but
also his outreach power to join forces.
And it's just proven, like, we've
been through the ringer and back,
and it's just incredibly wonderful to
have somebody in your corner who knows
exactly what you're going through,
just to go through it with you, really.
Raphaël: Yeah.
That's awesome is there anything you
would, I don't know, like advice you
would, give someone, a new founder
on how to decide, like, okay, let's
actually like do this thing together.
When you decide let's formalize
the thing and like actually build
a product or a company or whatever.
Laura Simpson: I mean, I'm pretty
big on managing expectations really
clearly , recently somebody gave me
that phrase, which is "clear is kind",
you know, like if you can clearly
define what your expectations and hopes
and dreams are and in my case, I was
really, wanting to put it in writing.
And so like early on, I think I came
back home and I wrote up an MOU, know,
I just was like, here's what, I still
have it, like we, here's what we want
in this partnership and here's you
know, I ended up going back out to
Vancouver after that and, when we were
in corporate, I think right before we
incorporated and we followed up the MOU
with like deal breakers and like rules and
Raphaël: that's good.
Laura Simpson: and like just kind of
wrote it all down, but like kind of
figured out each other's edges and
boundaries and needs and wants and
just like no goes and that changes
sometimes over time but like that's a
really great baseline to start with.
Raphaël: I love that.
I hadn't come across that as a way
of, setting things up and yeah,
I feel like that's really good.
Really setting those expectations.
Um, you're both on different
sides of the country.
So
Laura Simpson: Uh,
Raphaël: how have you managed that?
Laura Simpson: Zoom.
Raphaël: Okay.
Yep.
Laura Simpson: Yeah, we spend a
lot of time on Zoom, and phone
calls, I'm often walking the dog
while we're talking on the phone,
Raphaël: I love it.
Laura Simpson: the
time difference, and you know, and
he's got kids and I've got kids too, so
there's, you know, we're always juggling
around the schedules, um, but, you know,
except for the pandemic, like, I was
sort of the operational founder, and he
was more the out in the world founder.
That kind of set those roles pretty
clearly, and, you know, we have Slack and
all the other things, but I think that the
main thing is always coming back to those
roles and responsibilities, and then using
the tools we have, like Slack and GitLab.
Zoom and everything like that
to make it work and we went
together to San Francisco.
We went together to South by Southwest,
you know, being at those places
he's come out here and toured of
course and we try to get together as
often as we can but it's funny, the
Zoom relationship was pre pandemic.
And so when the pandemic happened,
that's why we were so ready to
jump on Zoom for online shows.
Cause we knew exactly how it worked and we
felt like we could tackle it, you know, it
Raphaël: remember thinking, wow,
they made this happen really fast
yeah,
Laura Simpson: but so
was our initial product.
Like we were doing shows before we had
a platform and before we had ticketing
and you know, we had revenue before
we had any proprietary products.
That's the kind of approach we take.
We're just like kind of build the
plane as it's taking off kind of thing.
Raphaël: yep.
I love that I remember seeing
that first setup with, what
was the tool you were using?
It was like, I forget what it
was, but yeah, like this sort of
project management slash podio.
There we go.
Laura Simpson: so Podio is the software
I used for the funding program.
That's why I ended up bringing it up,
because I'm like, I know how this works.
And so, yeah, the early days
of matchmaking, because it
was like a CRM, kind of.
So the early days of booking part of
our platform where we help match make
artists with spaces, we would just get
people, it was basically like getting
them to fill out a form and then just
like holding them up literally next to
each other and be like, do these match?
You know, it wasn't, you had some
filtering ability, but it was really good
early days trial and error, because you
would, you kind of do it and then you'd
be like, Oh, well, I wanted to do this.
It'd be so much faster
if it would do this.
But like practicing with a free
software was really helpful.
Raphaël: Yeah the ability to test things
out and just sort of work with what
you got is, so useful and so important.
Like, do you have any other stories of
things that you just kind of like, all
right, we're just going to try this
out this way and see what happens.
Laura Simpson: Yeah.
Well, first of all, I should say like,
I'm again, not a technical person.
Like I don't have like the
resources and the knowledge to
do, like to make something myself.
So I do have to rely
on off the shelf stuff.
So.
I mean, I'm trying to think, like we
used Eventbrite for the early ticketing,
Raphaël: Nice.
Yeah.
Laura Simpson: and we used, like, just
different iterations of Stripe after
that, and we were using Zapier to, like,
put everything together, Zapier, I never
know if people are like, is it Zapier
Raphaël: They used to have at the bottom
of their site, tiny little letters.
They said Zapier makes you happier.
Laura Simpson: Ah, thank you!
Raphaël: like that.
Yeah.
Laura Simpson: makes
more sense, it's a Zap,
so, that makes more sense.
Um, Yeah.
so like, little tools like that
would help stitch things together,
I think, and I'm trying to think.
You know, we still have a Facebook
group for the hosts to meet.
We never put that in our platform.
We're just like, everybody's on, all these
people who are hosts, most of them are on
Facebook, so let's just leave them where
they are and they can talk there, you
know?
Raphaël: a lot of sense.
Yeah.
Cool.
Um, is there anything, if you
had to like, think back to when
this first got started, is there
anything you would do differently?
Um, or any advice you would give yourself?
Laura Simpson: It's really funny, but like
definitely hindsight is 2020, but like,
we probably wouldn't still be in business
if we hadn't raised venture capital.
But.
We're at this point now where I'm
like, all the investors are like,
okay, this is going to be a slow burn.
Like we're finally catching
up after the pandemic.
Cause we basically were going to a
point with live shows, went online,
had a huge bubble of success.
The online shows raised our
seed round during that time.
And then had to basically start back
from almost zero with live shows,
Raphaël: yeah.
Laura Simpson: pull everything apart,
build it back up again, and then try
to make it happen for live shows.
So it's just been a really slow grind,
trying to get to, you know, the scale
that we really require to be successful.
I don't think it's impossible, but
it's just like, On the one hand, I'm
like, we probably would have died if we
didn't have venture capital, you know,
Raphaël: Yeah.
Laura Simpson: but at the same time, like,
the, the pace at which we're able to go,
like, our industry is still pretty archaic
and still slow and still relationships
based and stuff like that, and people
are very adverse to technology in the
music industry, as much as they like
their gadgets and their production stuff.
Like I was just at the National
Independent Venue Association conference
in New Orleans and I was sitting with
a guy from a venue and a booking agent
and they were like, I wish we had
something that would just like tell you
when artists are all free, like when
they want a tour so that we could just
access it and then we could just book
them from like, you know, like maybe we
should start a spreadsheet or something.
And I'm like, are you kidding me?
Serious?
Right now?
Like, I'm right here.
I've built this, you know?
It was so frustrating.
But like, I think there's just still
an aversion to learning something new.
So you're constantly trying to
make this thing that is technology
as, like, dead easy as possible.
Like, people want it to be,
like, Apple level easy, you know?
Um, without Apple level
investment, that's the challenge.
Raphaël: a disconnect there.
Yeah, I guess, yeah, that's
the, that's the work.
Laura Simpson: That's the work.
Raphaël: Yeah.
Nice.
what's, what's next?
Laura Simpson: Um, probably more travel,
like I'll be in and around the U.
S.
a little bit this year in different
parts of Canada like I said, relationship
building is still a real thing so I
spend almost all my time with other
music related people and groups.
Raphaël: Mm hmm.
Laura Simpson: Um, I don't really
spend, like I don't really indulge in
the tech community too much, honestly.
Raphaël: that's fair.
Laura Simpson: Although I am now on
the Board of Directors for Volta, which
is nice, and like, I get to be a very
different voice in that community and
then we're actually starting out
with a indie promoters program, which
actually allows for more people to be
our quote unquote boots on the ground
for shows and so we're rolling that out
in Toronto and then if it's successful,
we'll be rolling it out in other cities.
And it just means that there's more, like,
human interface to making the shows, which
again, you know, as much as you're a tech
company, we're in a people based business.
So we have to work around that.
Raphaël: Yep.
Awesome.
Cool.
Well, thank you so much, Laura.
Do you have a small tech product
that you can think of on the
fly, that you want to plug?
Laura Simpson: Yeah.
I guess I'm not allowed to choose
my Fitbit, which has been helping me
with my athletes triathlon training.
You know, there's, there's so
many great local companies.
And, There was a company I actually just
heard about on the radio this morning
that I was really going to look into.
So like early days knowing this, but
they're called Carbon Run and they
basically help make the water better,
like make rivers better, manage the
fact that, um, there's erosion and
like pollution and that sort of thing.
So I heard this clip on
the radio about them.
I'm like, I love companies that combine
real solutions for the earth, like,
and addressing all the terrible things
that are happening with climate change.
And, but also it's, That's a carbon
credit business so that, you know, it's
like giving those other companies like
a way to feel a little bit better about
not contributing to the environment.
Um, so yeah I really get behind
companies like that, that are, like
either good for social, good for
the environment, good for the heart.
Raphaël: Yep.
I love it.
Awesome.
Cool.
Well, thank
you so much.
Laura Simpson: You're welcome.
Thank you.
Raphaël: was
great talking to you.
Laura Simpson: you.
too.
Raphaël: Folks.
That was my interview with
Laura Simpson CEO of side door.
I really enjoyed chatting with her.
I loved learning about her life, the way
that she started working with her mom.
Her journey to California, the way
that she worked with Dan to come
together and build this company.
So, if you want to host a show in
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Good folks.
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See ya.