Raising a Business and Family with Anna Maste
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Colleen: Welcome back to Software
Social today, I have a special
guest on the show and Anna Maste,
the founder of Boondockers Welcome.
Anna, thanks so much for
being on the show today.
Anna: Thank you so much for having
me Colleen and I'm so excited.
Colleen: Can we start before we
talk about Boondockers Welcome
and your company and what it is.
Can you tell me a little bit of your
background, like before you started.
Anna: Yeah, so I am a
computer engineer by trade.
I M did that as my undergraduate
degree and worked for a startup here.
I live in Kitchener, Waterloo in Canada,
and it's a pretty big startup town.
So I worked for a startup here for seven
or eight years, I guess, post university
before I went full-time on Boondockers.
Colleen: So take us, I don't even
know where to start, there's so
much exciting stuff to cover here.
You were working as a computer engineer
and tell us a little bit about the
Genesis of this idea and this company.
I was working as a, essentially
an embedded software engineer.
The company I worked for
made networking equipment.
So not at all web development,
that was all really new to me.
But I was working full time, and then
I had a baby as one does sometimes
when one is in one's thirties.
And my, while I was on maternity leave.
In Canada, we are lucky enough
to have 12 months of paid, not
incredibly well-paid, but paid
maternity leave government sponsored.
So it's actually, I think now you
can actually take up to 18 months,
but only 12 months of them are paid.
But I mean, it's a small, very small,
monthly amount compared to what
my actual salary would have been.
I did, I took the full 12 months.
And during those 12 months, my mother who
lives about a 45 minute drive from here,
came regularly to visit her new grandson.
And you know while we were visiting
one day, she brought up this idea that
she'd had for a business, which was sort
of like couch surfing for our RVers.
She had been RV for probably
almost 10 years at that point.
And had self-published like some
online travel guides that had
gotten a decent amount of traction.
She was, you know, making
a decent income from those.
And so she had quite a following of
fellow are RVers, specifically looking
for affordable camping, or free camping
really is what her guides focused on.
She had this vision for sort of
this couch surfing or driveway
surfing idea for our RVers.
A community, people could offer their
own driveway to other RV years who were,
you know, in need have a place to stay
for a night or two and couch surfing,
as opposed to like Airbnb, works on
kind of a pay it forward mentality.
You're not actually getting paid for
people to come stay in your driveway
or on your couch, in that instance.
It's more of a, you know,
just for the love of it and
for the social aspect of it.
And our RVers are do this
naturally, they, you know, we'll
meet each other at a campground.
And after like, you know, sitting around
a campfire, having beers with somebody for
the first time, they will often say, oh,
if you're ever in my neck of the woods,
come park in my driveway for the night.
The idea that my mom had brought me
was to sort of formalize this and
to an online community that we could
charge a membership for and she had
originally actually asked me how much
I thought it would cost for her to
get somebody else to build it for her.
And I, at that point was on
maternity leave and suggested why
don't I try to build it for you?
Cause I figured it would probably be
pretty expensive, and we had no real
idea how much, whether it would take off.
It seemed like pouring her life savings
into that might be uh, not the best.
So that's what we did for the
rest of my maternity leave.
My mom would come over like one
day a week for a few hours, maybe a
second day, a week that usually not.
I would put some effort into building
the website, which I, like I said,
I had no web development background.
I was pretty much learning as I went.
And actually, it took two maternity
leaves before I actually finished
it, and we launched, so I had another
child in the interim, but about three
or four months after my second was
born, we launched Boondockers Welcome.
There's a lot, there.
That's a crazy story.
So, so you know what, my background
is electrical engineering.
So I had a similar transition.
I was doing like PLC, programmable
logic controller programming,
and also saw self-taught web.
Tell me, was it easier, harder
than you thought it would be?
Like teaching yourself how
to build a web application.
Anna: I mean, I started off actually
really, really basic our iteration which,
lasted for probably four or five years was
just built on top of the Drupal, CMS with
a bunch of mods that I wrote in PHP on it.
I had a little bit of PHP knowledge
from just playing around when
the internet first came out.
I want to say, cause I'm, I'm
feeling old, but so yeah, that
was our first iteration was, you
know, very little web development.
I think I learned a lot more about running
a server and web hosting and that sort
of stuff, and in those first few years
and most of the development was just,
you know, piecing together things in
a CMS that, you know, forcing it to do
things that it maybe wasn't meant to do.
I did eventually rewrite it
entirely in Python using Django,
which was a huge learning curve.
But at that point, I had actually
quit my job and had, you know, a
lot more time to from scratch and it
was, I mean, it was interesting and
challenging, but the internet is so
full of opportunities and information.
And especially if you're learning
something like Django or I'm sure
the same goes for Rails, right.
There's just such an amazing community
behind it that you can find so many
resources to teach yourself that for me.
Colleen: You were working a full-time job.
You had a baby, you're on maternity leave.
Presumably, I mean, you're an engineer,
so you have a well paying stable job and
your mom shows up your mom who likes to RV
and shares with you, her idea where you,
I mean, what was your reaction to that?
What was your first reaction to that?
Anna: I mean when she said she
wanted to hire somebody to build it
for her, I thought she was crazy.
I'm like, you have no idea if
this is going to make any money,
this is going to cost a fortune.
I've since seen, you know, a number of
people who've outsourced things like that.
And you end up with, you know, garbage,
especially if you don't know enough
about the technology to really manage
the people who are doing the outsourcing
for you, you end up with just a
very unusable, garbage website that
you've spent, you know, $25,000 on.
And I didn't want to
see that happen to her.
Anyway, so when I suggested that I did
it, I thought it would be more of it
just sort of entertaining side projects,
something fun to do on the side.
And it did, it kind of stayed that way.
We eventually, you know, did launch
and start making some money, but it
took a long time before we made any
real significant amount of money.
And that whole time, it was just
sort of a fun side project thing.
That was a neat opportunity for me to
do something with my mom like that.
I mean, we were always close.
Parents split up when my sister
and I were quite young, so it was
always just sort of the three of us.
It was a really neat opportunity
to work with her that way.
And I mean, it had its ups and downs.
We certainly, but it heads in a way that
mothers and daughters are likely to do
perhaps more than, you know, co-workers
or co-founders who don't have that bond.
But, it was a really great opportunity.
Plus, you know, like I said, would
often come in and spend time with
her grandkids, so it was really neat
for her and them in that respect to.
Colleen: Were you entrepreneurial
before your mom brought you this idea?
Was this something you always
kind of sorta wanted to do or.
Anna: Oh, it never, never
even occurred to me.
Anna: parents, you know, when they were
still together, when I was really young
owned a series of well, they owned a
bar actually, and my grandparents had
owned a bunch of sort of bars and hotels.
And I don't think it had
gone all that well for them.
It was like the eighties and, you know,
they eventually stopped doing that.
And I kind of always saw entrepreneurship
in that lens is like a very risky, you're
going to lose your life savings and
have nothing to show for it at the end.
So it never even occurred to me that
entrepreneurship would be something
that I would be interested in.
You know, I already felt like I was
pushing the boundaries as a woman in tech.
The idea that you know of going
on to found a startup was just
totally not something that even.
So your mom brings you this idea.
You think I can probably figure this out.
You start building it.
Do you go back to work
after that first year?
So I had a 12 month maternity leave.
I went back to work for, I guess, a year
and a half before I had my second kiddo.
Then after that again, I
took another 12 months.
After that 12 months, I went
back full time at that point.
I kind of went back and forth between
full-time and part-time trying to just
balance, not so much the side project
Boondockers Welcome, but just trying
to balance having a family, and yeah.
It was, I think about a year and
a half after I went back after my
second maternity leave that I ended up
actually just quitting my job full stop.
Was not at all because Boondockers Welcome
was making enough money to pay the bills.
Anna: because I was privileged
enough to have a husband who
had a very good paying job.
At that point he had taken a job
that involved a lot of travel.
And it was me with two kids, one of whom
was in daycare, and one of whom was in
kindergarten, and trying to get to my job.
And it was just, it kind
of went a little crazy.
We decided it was better for all
of us mentally, to a mental health
wise for me to choose to stay home.
Colleen: Oh, yeah.
I mean, that's literally my story as well.
Very incredibly similar, incredibly
similar story I had as well.
I did the whole trying to have a
baby at home and work part time,
then work full-time then work
part-time then I had another child
and yeah, so I'm familiar with trying
to balance all of those things.
Anna: And there are people
who do it and do it well.
And I have all the respect in the
world for them, but I mean, our family
adjust, we're not organized enough.
We are not type a enough.
We are not yet.
I don't know.
Maybe it's not, maybe,
Colleen: I don't know.
Anna: I'm, doing a disservice to people
by saying you have to be super organized
and type a, and you can't make it work.
But for us it was something that
we were lucky enough to be able.
Colleen: So you had decided to leave,
primarily for familiar reasons.
And you have a little side project.
Tell me about that period of time
in your life, where you like,
just so busy with the kids that
you didn't have time to work.
Did you try to do both?
What was that like?
Anna: It was mostly about the kids.
Anna: At that like I said, my
older one was in kindergarten.
My younger one was still a
toddler slash preschool age.
I did eventually have my younger
guy, I enrolled them in like a one
day, a week preschool at the local
community center sort of thing.
And then eventually we got into like a
three mornings a week co-op preschool.
So I did, you know, managed to
carve out, two hours a day, three
times a week to essentially work on
Boondockers Welcome, at that point.
Daniel would go to preschool, and I
would go to the library that was across
the road and sit there with my laptop.
And that was like mostly those six
hours a week was what I worked on.
When, they still took naps you know,
I'd sneak a little bit in there,
but a little bit after bed, maybe,
but honestly it was maybe six to 10
hours a week, tops that I was working
on the side project at that point.
We didn't move the needle hugely in
that time, but it did continue to grow
even without a huge amount of effort.
I pretty much just kept up with security,
patches and little updates here and
there, and a few feature improvements.
But, at that time it was
very slow but steady growth.
Colleen: So it was making.
Anna: It was.
Essentially, it's a
two-sided marketplace, right?
We have hosts who are usually our
RVers themselves who are willing
to have people come and stay on
their property for a night or two.
And then guests who are, you know,
obviously our RVers, sometimes there
are being sort of full time either for a
year or two or indefinitely, or sometimes
they're just going on month or two trips.
Anyway, we had seated sort
of the host base with people
from my mother's mailing list.
She had this mailing list of people
who had bought her travel guides.
When we launched originally, I
think we had about 200 hosts from
that list, which was fantastic.
We started charging essentially, if
you were a guest, you would pay an
annual membership and, you know, I
think I very much remember that first.
Oh my gosh, somebody paid, we
have an actual paying member.
And you know, though, I remember that
period where it was like maybe once
a week we would get a new member, and
then it was like, oh, maybe a couple of
times a week we would get a new member.
I think by the time I quit my job, we
probably were making a bout, we probably
had about $30,000 a year in revenue.
So, I mean, it's not nothing.
It was certainly, you know, pretty
impressive for not having put a whole lot
of effort into it, but there's a bit of,
I don't know, vitality, I guess, in it.
And that people talk to each other
about where they're staying all the
time, when, your are RVing, if you
meet somebody you're always asking, you
know, oh, where have you just come from?
And where are you headed?
So there's a lot of word of mouth
advertising that happened for us just.
Colleen: So, did you think it was
going to be successful or was it
solidly in hobby project status?
Anna: I remember before I quit my job
thinking, Oh, if we could just get to
this level, then I could maybe quit
my job and feel justified in doing so.
Um, And like I said, we certainly
were nowhere near there.
Did I really think it was going to get.
I kind of just figured it was a fun
project, and anything that we had from
it was gravy and just a nice addition
to our bank account, but we weren't
funneling all the proceeds back into
the company and like spending a bunch
of money on advertising and marketing
budgets or anything crazy like that.
I mean, it's a pretty, it's a very
low customer revenue product, right?
Our customers would pay an
annual membership of, it was at
first $25, and then eventually
$30, and then eventually $50.
But a lot of people would only stay
customers for one or two years sorta
of like, as they were traveling
and then they would graduate to,
you know, becoming a host, maybe.
So, it wasn't the kind of thing that
snowballed as quickly as one would like.
And it meant that, you know, you couldn't
read, you couldn't justify customer
acquisition costs of throwing a whole
ton of marketing money at it, or at
least we couldn't maybe at scale you
could, but at our level, we certainly.
Colleen: And how, by the way,
like, how cool is it that your
mother had a mailing list?
Anna: I know, she was definitely planning
ahead a little bit in that respect.
Honestly, she had built this reputation
for herself as an RV or who could
help you, you know, find free camping.
Before we even launched, she had actually
been interviewed by the New York Times.
It was like a whole profile about
her, you know, frugal, RV travel
is the name of her website, and
she still does run that right now.
Yeah, so She'd been profiled as
you know, somebody who can help you
find affordable and free camping.
And she got to the point where
she, you know, go somewhere and
people would recognize her and
say, oh my gosh, you're Maryanne.
You write those guides
are, those are amazing.
And so it was really amazing
what she had managed to build
and completely on her own.
I might be a computer engineering,
but I did not help one bit.
She taught herself everything she needed
to know to launch her own guides and
website and get all of that traffic.
Colleen: That's amazing.
Like that's super impressive.
So did you guys do any marketing?
I mean, outside of, I guess
everything she did before you
started the business was marketing.
So she just kept up with that, I assume.
But did you do anything else?
Anna: Not really.
No like paid marketing, we
never really did anything.
We definitely benefited from like
I said that the community aspect.
We did eventually launch an affiliate
program and we found that a lot of
influencers, specifically YouTube
has a lot of like RV influencers
who, you know, would either find out.
Product on their own and then just
create a video, reviewing it and leaving
all sorts of glowing reviews for it.
And that would drive a
lot of traffic to us.
Or we occasionally would reach out
to them and ask them if they would
become affiliates, but more often than
not, it was just sort of, they would
find us and sign up on their own.
And that really did help drive traffic.
So it was never other than the affiliate
fees that we paid them, like that
was our biggest marketing expense.
Colleen: It's just so wild to me.
I mean, I'm, you know, coming into
this, listening to all of the podcasts
and taking everyone's advice, and
you literally did everything the
way we're told not to do it, right.
B to C to.
And trust me, so spoiler
alert, we sold the company.
And so, I am now sort of going back to
the beginning and I am not doing it,
things because despite the fact that we
managed to have, you know, a great deal
of success doing it was really hard.
And I think we, you know,
lucked out in a lot of respects.
We had this sort of community that loves
to talk and pass things onto each other.
And we did eventually set up a Facebook
group that a lot of our members then
ended up joining and it really helped
to promote the product to people
who were interested, especially.
It's a bit of a strange idea, if
you're used to staying in an RV park.
The idea of like going and
camping on some strangers
property puts a lot of people off.
But most people say that, you know, once
you try it, you realize, most of these
hosts are just lovely, friendly people.
And it's like, we'd hear stories all
the time about, oh, skeptical to try it.
But then my first host, they had
chickens and they gave us all these
fresh eggs or they took my kids
out in, you know, showed them the
pond or they took a square dancing.
Like literally there was a one host who
took every guest who came square dancing.
That was always what happened.
It was like just all
these amazing stories.
And so, you know, eventually it
got to the point where it really
snowballed and, and these stories
just sold the product for us.
And as long as we put it up on Facebook
or people would tell the stories
amongst themselves in other forums.
And it started to just build its
own reputation and brand that way.
And that is nothing that I can really
take credit for other than choosing
a market where people love to talk.
Colleen: So, I mean, it sounds like the
value proposition here for most people was
the community less, the driveways less.
So the driveways.
And that was we totally didn't realize
until probably four or five years into it.
At the beginning we were marketing
ourselves as free cheap, affordable,
you know, and it turned out that
no, it was 100% about the community.
It was about, you know, unique
opportunities and great ways to
meet fellow RV years and share your
stories and meet locals who can
tell you about all the neat places
nearby that you should be visiting.
And eventually we tried to change some of
our messaging to, to position ourselves.
Colleen: So did you know, like
when you started this, did you
know other people doing this?
Did you have any examples
or community or friends?
Anna: people building their
own companies not are RVing.
Not RVing, I people
building their own companies.
Anna: Not really.
I mean, I have one friend who, you know,
has always been very entrepreneurial and
has built his own mini empire, but not
online, not online business, like not
website, building products like this.
And, I didn't even know.
I didn't even know to go look out on
the internet for other people like that.
It was just, I did eventually start
listening to startups for the rest of us.
And I kind of was like, Okay, there
are other people like that, but at the
same time, I kind of found excuses,
why my business didn't fit the model
of everybody else that was doing that.
And I'm like, oh, well,
it's not really SAS.
And it's not really, you know, all
these things that they say to do.
I'm not really doing those things.
Therefore, I guess I don't qualify.
It's a lot of imposter syndrome going on.
Colleen: So you had been building
the business like five or six
years solidly aside project.
I wanted to ask you when your
kids were in preschool, were you
doing nights and weekends then?
Or were you just doing when
they were at preschool?
Anna: I mean a little bit of
nights and weekends, but it
was certainly not hardcore.
Colleen: Okay, so you weren't doing any
kind of big push, you were just doing
work as it kind of fit into your life.
So you'd been building this
for like five or six years.
And then what happened?
Anna: Well, and then my, my younger one
started school full-time that was really
a, sort of the, the magical moment, right.
When it was like, instead of six hours
a week, I suddenly had six hours a day.
And it was like any parent who is
working a full-time job knows that
like you, or even a part-time job, like
you can fit more into six hours as a
parent than you could before, because
you're like, oh no, this is my window.
And I have to get stuff done.
Once, once my youngest started school
full-time then I, you know, we did like
some customer interviews and surveys
and sort of tried to figure out what
features our customers really wanted.
And that's when I totally
rewrote it from scratch.
And like, you know, we switched to Django
and I implemented a bunch of new features.
We changed our business model quite a bit.
The change allowed our hosts
previously had, were also guests.
So they were also paying, which meant
that when people stopped traveling,
they often dropped off as hosts.
So at that time we made a change to
all hosts, could sign up for free.
That really helped accelerate our
growth that had been, you know,
definitely slowed down from that before.
So it took me probably a year.
It was a little bit more than a year.
So about 14 months after my younger
one started school, before I launched
the sort of newly built site.
And that was really the
turning point for the business.
When all of a sudden, you know,
instead of 30, $40,000 a year, we were
within about a year and a half of
that, I think we had about a hundred
thousand dollars a year in revenue.
So it really started pushing
things in the right direction.
So you were basically working on that
full-time for, I mean full-time six hours
a day for a year to get you to that point.
I mean, there were vacations in there.
I'm sure that, you know, there
were times when I didn't.
And because it was no longer sort of
an MVP, I wasn't trying to get it out
the door as fast as humanly possible.
There was like a lot of, I probably
over-engineered at a bit, but honestly
I didn't want to break anything.
I had all of these customers who had
sort of expectations of at least making
it as good as what they've got now.
So unlike an MVP where you're like willing
to just push stuff out that might be
broken, I really wanted to make sure
that it was solid enough that all of
our current customers would be happy and
nobody would get lost in the shuffle.
I spent a full year essentially
rebuilding it from scratch.
Colleen: So when your youngest started
school, was there ever a period of
time where you were like, I should
just get a job because I'll make
more money and it's more stable.
Did you ever have that
conflict while you were.
Anna: You know what I really didn't.
Colleen: That's awesome.
Anna: I mean, part of that speaks to our
privilege that, you know, we had a house
that was paid off and my husband is also
an engineer, so I had a very good job and
Anna: But I didn't love
working all that much.
Like I never felt I enjoyed my
job as an engineer, but I never
really felt passionate about any
of the work that I was doing.
It was always just, well, this is
what they've told me to work on, so
this is what I'm going to work on.
Whereas, I loved building stuff
that I got to choose what to build.
And I got to decide
what tech stack to use.
And I got to decide whether
or not this was an important
feature and prioritize things.
That side of it, not just the technology,
but the actual, you know, product
management side of it was something
that was completely new to me.
And that I really, really enjoyed.
Colleen: So I'm calling you for
pep talks because about every six
months I freak out and I'm like,
I need to get a job right now.
Anna: It also, I mean, anybody who
has kids, you know, at that age
will recognize that it's so hard to
balance a full-time job, even once
they're in school full-time, right.
Like there's here anyway.
It's like, oh, it's a snow day today.
There's like somebody sick.
This person threw up that, you know,
they're the doctors appointments
and just all sorts of things.
And we had like teacher strikes and
just so many things cut into your
ability to work a full-time job to
the expectations of your employer.
And so even when my kids went back
to school, it was just going to be too
much of a pain to try and balance that.
Colleen: Yeah, so I did actually take
a job like eight months ago and then
I left it it's a whole thing, but
once I was there, I realized that I
was the only woman at the company.
The company was amazing.
Like they treated me really well,
and we technically had unlimited
PTO, but I have three kids.
Someone always has to be at the
dentist or at the doctor or they're
sick, or they have in California,
they get out at one 30 on Wednesdays.
Anna: Oh, my God.
Colleen: what's that about?
So, yeah, I think that is something I
have really noticed and I didn't notice
it until I took the full-time job that
with the kids, and like, I'm still the
primary caregiver, there's just so much.
And I know, there are men out there
who are the primary caregiver too,
and it applies to them as well.
But I think that more than anything is.
holds women back.
I mean, you know, obviously there's
maternity leaves and things, but
just somebody has to be on call
for all those things all the time.
And if it is always one parent, one
primary caregiver, then it is so
hard to commit to that full-time job.
And to not feel guilty all the time
about, you know, either you're feeling
guilty because you're not where you need
to be as a parent, or because you're
not where you need to be as an employee.
I feel like that's incredibly accurate.
Anna: And it's funny.
I have a friend who is she's like a
professor of social work and she told
me something the other day that was
apparently the women or people who
have sort of salaried jobs, where you
have the flexibility to, you know,
work at different hours end up feeling
way more guilt than parents who have
sort of like scheduled, you know, nine
minimum wage or whatever shift work
job, because for them, you know, it's.
This is when I have to be there and I'm
not going to feel guilty because I had to
miss your middle of the day school recital
or whatever, because it's out of my hands.
Whereas parents who have some flexibility
to, you know, I could skip work for
two hours and go watch your Christmas
concert, but then I have to make up that
time later on, those parents are the ones
that struggle the most with that balance.
That like speaks to me.
No one has ever said that, but it
makes sense because that's exactly
what would happen is I'd be like, oh,
my daughter has her ballet recital
at two in the afternoon, but then you
come home and you're like, oh, I should
work for those two hours that I missed.
Anna: Yep, exactly that.
I mean, that still happens when you're
self-employed to some degree, but
at least it's your own internally
imposed deadlines and not some deadline
that somebody else has imposed upon.
Colleen: So I want to ask you a
question about your appearance
on startups for the rest of us.
I mentioned this before the show, but it
was you and Rob didn't really dig into
it, but it was like one of my favorite
things you said is you were talking about
going to Microcom and you were talking
about identity and how hard it was to
be a business owner when you didn't.
I interpreted what you were saying is when
you didn't see anyone else like you doing.
I mean, I know people who run startups
here, like venture funded startups,
you know, almost exclusively men,
but the people that I interacted with
every day were the other moms who
are dropping their kids off at school
and picking them up every day and to
them looks like just another stay at
home mom who would drop my kids off at
school and then walk home every day.
And, when my kids were younger, you know,
those kids, the parents of my youngers
classmates in preschool, you know, I
would sometimes go have a coffee with
them while their kids were at preschool
because I had that flexibility, but
it became increasingly difficult for
me to I identify as an entrepreneur
when from, you know, the outside and
by all the people who surrounded me,
I identified as a stay at home mom.
There was just such difficulty balancing
those and making sort of that internal
decision that no, I am an entrepreneur,
and I can focus on my business and
that can be part of what defines me.
So let's get back to your business.
You ended up selling it, right?
What's the exciting punchline.
This is exciting part.
Anna: So essentially we at the beginning
of the pandemic, things are RVing
really got popular in case you hadn't
noticed, there was a whole sort of,
it's the only safe way to travel.
You don't have to stay in a hotel.
You have your own kitchen with you, so
you don't have to eat in restaurants.
You don't have to fly anywhere.
So our RVing really took off during the.
And camp sites became even
more difficult to come by.
So alternative camping opportunities
like we provided were very in demand, and
essentially last year, at the beginning of
the year around March, we were approached
by another company in the space.
They're called harvest hosts.
They have a very similar business model
to ours in that it's an annual membership,
but instead of staying on other, our
RVers property, you stay at wineries,
breweries, museums and things like that.
So, they had grown quite substantially,
as well over the years prior to that.
And they had actually just
taken a whole bunch of funding.
We actually had for a company that had
never really anticipated, we were going
to go anywhere, we actually had several
investors reach out to us, as well after
the pandemic started and things started
really taking off or RVing, we had
several investors reach out, interested
in, you know, whether we wanted to take
investment money, and that was not
something that I was really interested in.
I didn't even like having a boss, the
idea of having it, investors just was not,
not something I wanted to even approach.
Anyway, but harvest host had
taken a bunch of investment money
and they were looking to expand.
And so we, I knew that our
customers already about half of
them were also members of the
harvest host membership group.
So it was a real good fit.
It wasn't just selling to, you
know, some big conglomerate.
it was it.
So I knew that it would probably
sit well with our users and that
was important to both me and my mom
cause you know, we really did our
very best to sort of, we were very
a customer centric company, right?
We listened to our customers as much as we
could, and we made lots of decisions that
were probably poor business decisions,
but very customer centric decisions.
So w we wanted to make sure
that we did right by them.
And anyway, so when harvest
hosts approached us, we kind
of said, well, maybe, and then
the uh, the price was right.
So it was hard to say, no.
Colleen: Do you guys have to like,
so you're this the first time
you've sold a business, right?
Do you need, did you have to get lawyers?
Did you have to get one of those
merger and acquisition people?
Anna: We did get a lawyer.
I definitely would not have
done it without a lawyer.
I would not recommend
doing it without a lawyer.
Yeah, so, I mean, it's
just a local law firm here.
Harvest hosts, having just taken a
bunch of investment money had like
highfalutin, New York city lawyers.
And my lawyer joked that like
their secretary probably made
more than she did per hour, but
my lawyer did, I just find jobs.
She did an amazing job of helping
us through the whole process.
Colleen: Now that you guys have
sold it, are you still involved
or is it like a clean break?
Anna: For about six months
after the sale, I stayed on to
just help with the transition.
But then after that it was a clean break.
So those six months we
sold in may of 2021.
So those six months
ended back in November.
So now I am a free agent.
Colleen: How do you feel about all of it?
Anna: At the beginning it was kind of
bittersweet, and you're always kind
of like, oh, did we sell too soon?
I didn't really feel that way too much.
There's a lot of stress in running
a company, once it gets to a certain
size, especially, you know, there were
always sort of liability questions.
Like, should I be worried about somebody
getting hurt on somebody's property?
Should we have insurance or,
you know, or my terms protecting
me, should anything go wrong?
I think more so than, you know,
what a S small SAS or anything that
particular company stressed me out.
That made me happy to walk away,
and you know, that there was always
sort of a lot, because you're dealing
with people and consumers, you know.
W we had a very popular Facebook
group, but people are people, and
every once in a while you get the
trolls and it just goes crazy.
And there are some people who can let
all that stuff roll off their back.
And I was just not one of them.
I was always sort of very emotionally
invested in like, oh gosh, these
people are being mean to each
other on our Facebook group.
And I can't let that happen.
And it was always.
Just stresses that I was happy
to not have to deal with anymore.
Colleen: So have you done
something cool with all your money?
Like, did you ever have a goal?
Like if I sell this, I'm going
to Tahiti cause that's what
I'm going to do by the way
Anna: Ah, yeah, Well, unfortunately, the
money hit our bank account and it was
like, you know, peak COVID, we're not
really comfortable traveling anywhere,
it was nobody had their vaccines yet.
And yeah, so the money has done
nothing, but probably decrease in size
because the stock market took a tank.
So That's pretty much All
that's happened at this point.
Colleen: All right.
Well, let me suggest to Tahiti
in two years, once it's safe to
travel again, it looks beautiful.
Tell me what you're doing now.
Anna: So, I'm starting another
company because I loved doing it.
I mean, my kids are still in school,
you know, we're not really ready to
retire yet, and it's still COVID.
I was still not really going anywhere.
So retirement seems just
silly and pointless.
And I mean, I'd have to
do something with myself.
So one of the problems that, of
course the standard story, right?
If you want to figure out a problem to
solve, start a company, and then you'll
find problems that need to be solved.
One of the things that I ended
up noticing, we had a very active
or, or well-read newsletter
that we sent out every week.
Send a, you know, very quick, here's
a listing of all of our new hosts.
We had probably like 20,000
people on that mailing list.
And every Monday we would send that
out, and we'd see a nice bump in sales.
So it was a really great marketing
tool for us, but very late in the
game, actually, after we'd sold, I went
and looked and realized we had like a
double opt-in mail list where you have
to, you know, subscribe, and then go
back to your email and confirm in that
that is in fact what you wanted to do.
And I went and managed to you couldn't
see this on any dashboard, but I was able
to like download a bunch of CSV files and
sort of dig into it and be like, wow, only
60% of the people who try to sign up for
our mailing list ever actually confirm.
I finally, I went and did a little
bit of research and it's like, Yeah,
that's pretty much the norm is that
only about 60% of people signing
up for newsletters letters actually
finished that confirmation step.
So I am starting a company now
called subscribed sense that tries to
help people help a mailing list and
owners increase that confirmation.
So where can people find
you on the internet?
If they want to learn more about
you and follow your new journey?
Anna: Yeah, if you want follow me, I am on
the Twitters pretty regularly these days.
So my handle is a school girl, spelled
S K U L E G I R L .School the name for
our engineering, the engineering program.
I went to calls itself S K U L E school.
So that was the joke there.
That's been my internet
handle since I graduated from
university a long, long time ago.
Yeah, so the best place to find me.
Well, Anna, thank you so
much for coming on today.
Anna: Thank you so much Colleen.
I'm so excited to have been here.
I gotta say I was Twitter
friends with Michelle before
you guys launched the podcast.
And when, you ended up with her co-host I
was very excited because I know Michelle
has, you know, all the business acumen,
but you're a tech girl and there are so
few of us who are not just women running
their own companies, but technical
women running their own companies.
So I was really excited
to, to get to meet with.
Colleen: Well, thank you.
Thanks for joining us for this week's
episode of software social, please let
us know what you think of the episode.
You can find us on Twitter
at software soc pod.