What's up, everyone?
This is Cortland from EndyHackers.com, and you're listening to the Endy Hackers podcast.
On this show, I talked to the founders of profitable internet businesses, and I tried
to get a sense of what it's like to be in their shoes.
How did they get to where they are today?
How do they make decisions both at their companies and in their personal lives?
And what makes their businesses tick?
Today I am talking to Matilda Collin, the CEO of Front.
Front has been described as a multiplayer version of Gmail.
It's a shared inbox that puts all of your emails, apps, and teammates in one collaborative
workspace.
Matilda, welcome to the Endy Hackers podcast, and thank you so much for coming on.
Thank you for having me.
So Front is a very impressive company.
I think you guys have over 3,500 customers now, is that right?
Yeah, I think over 3,600 now.
Okay, yeah.
And you guys have achieved a lot since you started it about four years ago.
I want to start by getting to know more about you as an individual.
What kind of person becomes the CEO of a company like Front, and what were you doing before
you started this company?
Sure.
So I started the company when I was pretty young.
I think I was 23, so I've not done much before doing Front.
Basically I went to a business school in France.
I graduated.
I then joined a startup.
It was a software startup that was doing a contract management system, and I stayed there
for a year.
What I did was launching a new product for them, and then I quit, but I was passionate
about just softwares in general, so I decided to work on a software that I was even more
excited about, which was email.
So I was in France at the time, and then a few months after I moved to the U.S., and
then Front grew, and here I am today.
Now I hear a lot of founders who start by going to business school.
I hear a lot of founders who start by working at a startup.
You did both, so now I have to ask you, with the benefit of hindsight, what do you think
was more helpful?
Definitely working in a startup.
I don't think that, like if anything, when I was in business school, the thing that was
most helpful to me was meeting with entrepreneurs that had built companies and that inspired
me.
But apart from that, I think where you learn the most is when you get things done, and
so working on an actual project was where I learned 99% of what was useful for me afterwards.
Yeah, that's what I would have guessed would be the case.
But at the same time, business school is so popular that I wonder what kind of lessons
you get out of it and whether or not it's been helpful at all.
Yeah, no, it's been helpful.
I'm sure every business school is different.
Probably in France there are different than in the U.S., but for me, I think knowing a
lot of things about how generally a business work was helpful in the first two years, then
I took a year off where I worked in two companies, a huge company, I didn't like it, and a super
small startup.
I loved it.
So in essence, internships were helpful so that I could know what I was passionate about.
And then my last year, I decided to specifically focus on entrepreneurship, and that was super
helpful.
I worked with four different entrepreneurs at different stages of their companies.
So from the moment you start, the moment you scale, and then the moment you fail, and at
the end, just working on my own project, and that was super, super helpful.
But I think that reflecting back when I was thinking about what are the things that I
learned, the main things I learned were let's talk to founders that have built businesses.
Let's try to understand what it means.
And that's the thing that really drove me to start my own company.
Because I think if you just learn in the books, I think you will always think that it's impossible
to do because it seems just so hard to start something from scratch.
Yeah, I think probably most people listening to this podcast are at least vaguely interested
in starting their own business.
Maybe they listen to podcasts like this, maybe they read books, maybe they read blog posts,
but it's really hard to take that initial plunge and get the confidence to actually
start.
How confident were you when you first decided that you wanted to run your own business?
And what were some of the things that helped you become confident besides just meeting
entrepreneurs in real life and getting to talk to them?
So it's a good question.
So the first thing that you should know is when people were asking me about what I want
you to do after business goals, and I could hear some people say, I would like to start
a company.
And I was always like, well, I wish I could say the same thing, but it just feels too
hard to me.
So I think that I wasn't confident at that time that I could start my own company.
So I think if anyone is listening to the podcast and feel that way, then I think it's totally
normal.
I think there are two things that made me believe that it was possible.
The first thing is joining a startup and actually seeing what it took to build a product and
launch it and sell it, iterate on the product and sell it and et cetera.
I think that gave me some confidence.
So being exposed to at least one young company, I think is super helpful.
And the second thing is trying to meet with one person, whether it's a friend or a mentor,
anyone that will believe in you was also super helpful.
So in my case, I was dating someone who started a company at the same time and just really
believed in me.
And today is my husband.
And I think it's helped me so much to know that he knew that I could start this company
and just hearing that from someone, whoever it is, is incredibly helpful.
Yeah, I think a lot of times if you're procrastinating doing something or if you're worried about
something being too hard, just taking that first step is the hardest part.
And in fact, even doing the thing isn't as hard as taking the first step.
And so having somebody who believes in you or someone who can sort of give you the opportunity
to get your feet wet is really helpful.
Yeah, it is.
And one thing I would tell you, so once we started building Front, a few months after
we applied to Y Combinator and we got accepted.
So we went there and at YC, every Tuesday night, you have a dinner with a successful
entrepreneur talking about their business.
It can be for me, it was this year of Stripe, Facebook, Dropbox, super successful people.
And just hearing them talk about how hard it was when they started, how non-obvious their
idea was and how hard it still is today is one of the things that helped me the most.
I'm sure that a lot of people have heard about the hard thing about hard things, but it's
one of the books that has helped me the most because just knowing that it's hard for everyone
will prevent you from thinking about, is it normal or not that I find this hard?
And so then you can just focus on actually making progress, whatever it is.
And you can stop wondering if it's normal that it's hard on that and just keep doing
what you're doing.
So one thing that's interesting about your story in particular is that Front is an app
in the email space.
And it's notoriously difficult to build an app in the email space.
It's very hard to get a product out the door, it's hard to deal with all the competition.
And so in some sense, it kind of was just you doing this thing that was a little bit
harder than a lot of other startups.
Why did you decide to work on Front?
And how did you stumble onto this idea?
Yeah, sure, and I think it's a combination of two things.
The first one was being exposed to the SaaS world and looking at the impact that the contract
management software that I had launched had just made me super happy because I was very
happy to see that you could build a software in just a few months that would actually deeply
change how some people were working.
The thing is, I wasn't using contracts to get work done, I was using email.
And so I think I was fascinated by the fact that email was the tool that people use the
most today to get work done, and it's the only software that has not evolved in the
past 10 years.
So if you look at Gmail 10 years ago and Gmail today, it's very, very similar.
And so I think the space was interesting to me.
Now, the pain point that we started with, which was shared email addresses, so any email
address like support, ad sales, ad PR, ad, et cetera, is a pain point that I had identified
when I was working in this startup.
And so people were emailing this email address and then nobody knew if someone had replied
to it or we were replying twice to the same message.
And so I just thought that that could be a really good entry point in this space.
And that's why I started front.
Did you do anything to validate your idea to make sure that it was a good idea with
working on?
And were you so excited that you just jumped into it from the very beginning?
No.
So I mean, you know, I feel like the first two years of front were validating the idea.
So I did a lot of things.
I took to a ton of companies in order to understand their email workflows and trying to understand
what was broken.
I tried to write a lot of content on email and communication, have people get in touch
and especially people interested in that fit space, talk to them about just the space in
general and what pain points they've identified.
And then just start building something, even screenshots of what we had in mind, show them
to people, have them excited or not excited.
So it was constant validation for the first two years and even more true in the first
two months.
Yeah.
Two years is a long time to spend validating your idea, I guess to some degree, you don't
have a choice though.
It takes that long to really do all the steps you need to see if your company is going to
be viable.
Let me ask you, what was motivating you at the very beginning?
I think everybody's driven to start a startup for different reasons.
Some people want the money, some people want the financial freedom, some people want to
change the world in a specific way.
If I could have gone back in time four years ago and asked them until then, why are you
doing this?
What would you have said?
Yeah.
So the answer to this question is very naive, but it's true.
So when I was a kid, I was in France, and one thing that struck me is that no one in
my family liked their jobs, and so they didn't want to go to work on Monday, they were always
looking forward to being on vacation, and I was a very happy kid, and so just thought
to me that it was a bit sad that when I would grow up, I would not enjoy working.
And so for me, starting a company was a way to create a place where I would be happy to
come to work every day, and hopefully other people would be happy to come to work every
day.
And so then if I was on top of that, able to work on a product that would make other
people happier, more productive, more engaged at work, then I would be even happier and
more fulfilled.
And that was true four years ago, but it's still true today.
That's what drives me.
Whenever people join the front team, I do a presentation during their onboarding week,
and I always mention that front is a means to two ends.
One is happy employees and two is happy customers, and front isn't good in itself, it's just
good because it helps us achieve these two things, and that's really the main driver
that I have, but I think also the whole company has.
How do you like being a first-time founder, and has the journey been different than you
first expected it might turn out to be?
So one, I love it.
So I love my job, I think it's an incredibly hard job, but it's very rewarding.
Being a first-time founder, I think you just realize at every step of the way that your
job is going to change in maybe every six months, and so you need to be very humble
and be self-aware about the thing that you don't know, so that you can learn the thing
that you don't know, but I love it, and I would do it again, and I think being a first-time
founder is also really good because you can invent a lot of new ways of doing things,
and I find it incredibly exciting.
Yeah, that's super cool that when you start a company, it's pretty much you in control,
and so you don't really have to be beholden to the status quo, and you can do all sorts
of new things, and it's risky because you can spend a lot of time doing things that
aren't really helpful to the bottom line and achieving your real goals, but at the same
time, it's pretty freeing to be able to do that, especially when you come from working
a normal job where you don't have as much control.
Yeah, and I think specifically on front, working on an email product, I think it was super
important that I actually didn't have a lot of work experience because I think it's easy
when you use email so much to get used to a specific way of dealing with email and then
not be able to have a new pair of eyes on a radically new way to deal with email, and
I actually think that the fact that I was young, my co-founder was young, and most of
our early employees didn't have a ton of work experience and or no experience in the email
space enabled us to be pretty busy in the value proposition of our product, and I think
that led to us being quite successful so far.
Cool.
Well, I want to dive into the details behind how exactly you guys have done what you've
done and how long it took you to figure out that perhaps having a fresh set of eyes was
crucial to you guys.
So let's go back to the very beginning, the days when you guys first came up with your
ideas and got started.
What was sort of the first step you took to work on front?
I mean, so the first steps I took was first of all, just talking to as many companies
as possible, as I said, and then at the same time, you know, you can just keep talking
to people, so I started this company with my co-founder who is the CTO of the company
and so he started to build the product very early on.
And so the idea was super basic.
It was an email client, so you could receive and send messages, but then you had two features,
you could assign messages to people and comment internally on any message that was coming
in.
And so he was building this and I was talking to people hoping that one person would say,
happy to test it when it's ready.
And then at every step of the way, whatever I had to show, whether it was just a one pager
or then a screenshot or then a product that wasn't working that well to a product that
was working okay, then I put that in front of whoever I was chatting with.
And I feel like one thing that I've seen is founders can sometimes wait too long because
they are not proud of what they've built because it's obviously shitty because anything that
you build at the beginning is not working or is bad.
But I think that putting whatever you have in front of as many people as possible is
something that helped us get to product market fit as quickly as possible.
So pretty much the early days where I was chatting with users and my co-founder was
building the product and because I was chatting with users or potential users, he was changing
how he was building the product and so on and so forth.
How did you know that was the right way to go?
Because I think the vast majority of first-time founders do exactly what you said.
They're embarrassed about what they've built.
They build it for six months or a year before they show it to a single person and by the
time they have, they realize they've built the wrong thing and it's too late to go back.
How did you know to do things the way that you did it?
Hard to know.
I think it's just that personality where I'm someone that I think is more pessimistic than
optimistic.
So I always feel like I will not think that something is great until a lot of people have
told me that it's great.
So I think it's just who I am.
I'm also someone that's very focused and so I knew that in the early days of the company,
there are just so many things you could be doing from talking to people in the same space
to talking with potential investors, to talking with potential partners, potential hires.
And I felt like being super focused on just doing two things, which were talking to potential
users and building the product, I think helped us a ton.
So I also think that you need to have a lot of confidence, you need to be low ego in order
to do what I've said you should do, which is just put it in front of people as early
as possible.
Because for sure, people will tell you that it's bad, but you just need to use that as
a data point and they're not judging everything you've done and or who you are.
And I think that if you're in this state of mind and don't have too much of an ego, then
it will be easier to do that.
It's funny to hear you say that you're a little bit more pessimistic than the average person
because I think the stereotype for the founder of a startup is to be wildly optimistic, to
believe that everything's going to work and throw caution to the wind and be extremely
amenable to risk.
What do you think that pessimism comes from?
So I don't know if pessimism is the right word, maybe it's paranoid, I don't know if
it's better, but it's basically this idea that I just always think about what could
go wrong rather than hope that things will go well because I just feel like it's so when
you start a company, things will be hard.
You will mainly have bad news and sometimes you'll have one good news.
And I think that it's incredibly important to face this bad news and so you should expect
them.
And I don't know, I don't know where it comes from, it's just that I know things will be
hard, I know that things will stop working at a point and if I can anticipate that, then
I have the confidence that we'll be successful in the long run.
So something that's funny about this pessimism or optimism is that I remember one thing,
which is when I was at YC, so we had not launched the product yet, so super early on.
And we had a batch with 100 companies.
And the partners were telling us, so in this batch, most likely about three companies will
work out.
And at that time, I was thinking about what we were doing and I hated everything about
our products.
So our batch mates were asking, oh, can we trade the product?
And I was like, no, you should use our competitor, it's much better.
So on one hand, I was very, I don't know if it's a shame, but not happy about the current
state of the business.
And so that's the paranoid, pessimistic state of mind that I was referring to.
On the other hand, when YC was saying, probably three companies will work out, in my head
I was like, I'm pretty sure front will be one of them.
And so I think I have always been that way where I'm never happy about the current state
of the business.
And I always have a lot of confidence in the fact that we'll figure things out.
So give me a sense of the timeline around the early phases of your business.
When did you come up with the idea versus when did you finish building the product versus
when did you guys get into Y Combinator?
So we started working on front in October 2013.
We applied to YC in March 2014, so about six months after.
And we launched the product in June 2014.
So nine months after we started working on it.
And how were you guys funding things before you got into YC?
Because a lot of founders or would-be founders struggle with trying to figure out the finances
behind how they can take time off or save up enough money to actually work on a business.
Yeah, so we were lucky enough to have an angel investment from a startup studio in France.
And then six months after, we got $120K from YC.
So that was fortunate.
Yeah, that's great, because that's more than enough for I think two people to really work
on a product for at least a year and try everything that you can.
Yeah, exactly.
You've written that at the beginning of front, your job was to do literally everything that
wasn't engineering.
So you're doing sales, support, product management, hiring, marketing, etc.
What do you think, out of all those jobs, was the most important to getting through
your very first year as a company?
Sales for sure.
And it wasn't my favorite one, probably my favorite one was product, but I knew that
I had to spend the majority of my time demoing the product to potential customers and then
talking to these customers about what they were liking and not liking about the product.
So I think sales is something that either you love or you hate.
And even if you hate it or dislike it, you should spend the majority of your time doing
it when you're doing a software.
Yeah, I think one of the cool things about sales is that it forces you to actually talk
to your customers.
And it's easy to sort of have this mass marketing approach at the beginning, it's what everybody
sort of dreams of.
I'm not going to talk to anybody, I'm just going to put my product out and it's going
to spread like wildfire on Google or through the tech press or on Hacker News or wherever.
But it deprives you of the ability and the chance to really talk to your customers and
find out what they like or what they don't like.
Do you remember any of the lessons that you were learning by talking to your customers
and doing sales early on?
I mean, the main things is I learned a ton about the product, so it was funny because
I remember that my co-founder was building features and every time I was like, oh, I
think we just need one last thing and then people will use it.
So he was building that and then I was doing it and then people were like, oh, and this
other thing.
So then I was coming back and I was like, oh, one last thing.
And that lasted, I don't know, probably a year.
So yeah, I think that's what you learn the most is just what people want.
Yeah.
How do you get out of that rut?
Because that's something that I talked to a lot of people who are starting companies
and hey, my product's not good now, but when I add one more feature, that's really what's
going to make it take off.
It's a pretty common viewpoint and very often ends and companies never really finding product
market fit.
How did you guys get to product market fit and get out of that cycle?
Yeah.
So I think it's different for every industry.
I think in the email space, you have to first get to an MVP that people are going to use.
And so when you're doing email, there are some features that you cannot not have.
So you need to be able to CC, BCC, you need to be able to add attachments, et cetera.
And so generally you need to have tags, for example.
So I think that you should get to a point where at least one customer is going to use
it and then understand how many more customers could be using it.
Because the truth is you always find people that want more out of your product, but the
goal is not to build everything that people ask for.
So for us, this period, pre-launch was good just to know what an MVP would look like in
our space.
And so what I want you to find is when can we have 10 customers paying for this product?
If we can have 10, then most likely we can have 1,000.
So tell me a little bit more about this early sales process.
What was it like finding and talking to your first customers?
And how did you even know who to reach out to?
So I hustled and I think that's the only way to go.
So first of all, I was writing a ton of content on email and communication in general.
And then we had a waiting list.
And so whenever people were subscribing to our waiting list or beta request, then I would
contact them and ask if they want you to see a demo of the product.
I did that, I asked my network.
The good thing about joining YC was the fact that they had a huge network of YC companies.
And so I probably reached out to, I don't know, a lot of them in order to know who would
accept seeing our product.
And we did a lot of things.
We launched on product hunt probably seven times.
And we were in every startup listing that you could think of.
And we, I was, I don't know, talking at a few events so that I could tell them that
frontapp.com was amazing.
And so I just did so much.
And I think there is absolutely no shortcut.
You need to hustle, hustle at every, every stage of the business.
And it's, for what it's worth, it's center today.
Yeah, it's funny to hear you talk about that and also talk about why you wanted to get
in startups in the first place, which is to create a job that you actually would enjoy
going to.
Yeah.
And then you doing all this hustling, if you didn't actually enjoy what you're doing, because
it would just be like a normal job, but even more work.
Yeah, I agree.
If you're optimizing for the amount of time you'll spend working, then a startup is really
not a good fit.
But I just love, and I've always loved, what I was working on.
And really, I think it's super important to understand then that being happy at work doesn't
mean that it's peaceful or easy or fun.
But at the end of the day, I care about our mission.
I care about the people I work with.
I think it's super rewarding to make progress, especially on something that no one has ever
done before.
And every founder can probably relate to that.
And that's what makes me happy every day.
So back in June of 2015, about a year after you guys launched, you wrote about how you'd
reached the point where you'd put some essential fears behind you regarding building something
that people want, attracting talent, securing funding, landing customers.
What do you think was the biggest turning point after a year of working on Front?
I think it's hard.
I don't think that you ever wake up one day thinking, okay, we've nailed it.
Now things will work out.
And it's still not how I feel today.
So I guess it's just, I think that the moment you realize that you have a handful of customers
that are using your product or happy to use your product or paying for your product, and
you know that there is no other product that they could use that would be better for them.
That's when you end, you realize that that's a handful of customers, but there could be
many more.
That's when you realize that you have for a market fit.
And so you can think about scaling your business.
Yeah, give me a breakdown on what it was that you were selling customers on and why people
used Front.
What made it different than the normal email experience and what made it something that
people were willing to pay for?
Sure.
So we started as a shared inbox tool.
So it was the easiest way to manage any shared inbox and a shared inbox could be a shared
email address or a shared Twitter account, Facebook account, a shared tool, your number.
And so there are a few reasons why people would use our product and find it better than
any other tool.
So the first one is we had a lot of support teams use the product and they preferred Front
over a ticketing system like Zendesk or Freshdesk or Desk because of the fact that it was an
email system at first.
So the communication looked very personal.
You didn't have to receive your ticket number 12345 reply above this line and it was also
very intuitive to use.
So if you wanted more people in your company to see support requests, then it was easy
and less expensive as well.
So I think we had traction at the beginning because it was just a better way to support
your customers.
And then what we saw is all these features around collaboration and new workflows that
we enabled when people were dealing with email were actually useful to support teams, but
also account management teams, product teams, recruiting teams.
And we started to see that these teams don't have a ton of other solutions than Gmail and
Outlook to deal with their emails, yet Gmail and Outlook weren't specifically designed
for businesses or for teams.
So whenever you need to collaborate your CCBCC reply all forward, et cetera, it's super hard
to integrate it with any other tool that you're using, like a CRM or project management tool.
And so then we got traction on these other teams.
And so that's when we started to realize that there was something very unique about what
we were doing.
That's such a, on one hand, it's such good news to see all these other types of people
and roles being able to use your product and actually find a huge benefit by using it.
But on the other hand, one of the things that you hear people tell founders all the time
is to focus.
Focus on your core user, focus on your core use case, don't get distracted by any of
the hundreds of other opportunities and features you're going to be able to build over the
course of your business.
How do you make that decision to widen your net and go after more customers and was that
a tough decision to make?
Yeah, I think it's, you know, it always depends on your space.
So email is interesting because it's one of the rare tools that's used by companies
of two people and companies of 200,000 people.
And it's used by engineers and by product managers, but also by support reps, themselves
reps, et cetera.
So I think we were in a unique situation.
I would obviously tell founders to focus, but I think one of our opportunities was the
fact that we were a horizontal product and the fact that you could have both a support
team and an account management team and a sales team on front.
So now it doesn't mean that we didn't focus.
So there are some teams where front is not good for them, there are some industries where
front is not good for them, there are some size of teams where front is not good for
them.
And we had to be very deliberate about not building the features for these people.
So let's talk about growing your team.
In the beginning, it was just you and your co-founder working on front.
How did the two of you meet?
So we met in France in a startup studio.
So I think five years ago, the community in Paris of people interested in tech and especially
in SaaS was pretty small.
And so I met him in a startup studio.
So the funny story about my co-founder and I is that we started the company together
just a few months after we met.
And usually you hear people that our best friends have worked together, our brothers
and sisters.
And for us, it was very different.
So we actually spent a ton of time together in the first few months asking ourselves all
the tough questions that we could one day encounter.
So for example, what happens if you want to sell and I don't want to sell?
What happens if I want to fire you or you want to fire me, etc.
And we just felt so aligned.
So that was one thing that helped us decide to work together.
And the other thing was, I think that today our relationship is still fantastic after
five years.
So it's definitely one of the things I've been the most lucky with.
And I think it's because there was just a lot of respect between the two of us.
So I usually respect who he is and what he works on.
He really respects who I am and what I work on.
And so that's why even a few years after we still have a very strong relationship.
I think people really underestimate how helpful it can be to have a co-founder who you trust
and you work together well with.
And also how harmful it can be to work with somebody who you don't have a good relationship
with.
It actually kills a tremendous percentage of businesses, just disputes between two co-founders.
Yeah.
And I think the interesting thing is the fact that you get in the world with this person
is actually not the most important thing.
The fact that there is deep respect is the most important thing.
So what's it been like growing from just the two of you to a team?
How did you make your first hire?
And how did your role change as you brought in more and more people?
So first hires network.
So our first hire is still with us today.
We hired him in France.
Then he moved with his whole family in San Francisco.
He was just a friend of a friend of a friend.
And so was our second hire and third hire.
So then our jobs changed so much.
So we went from, I will talk about my job specifically, I was doing everything.
And then for everything I was doing, I hired people better than me.
So I was always doing the thing that no one was doing.
And then I was leading all the teams.
So I was head of sales and head of marketing and head of recruiting.
And then I hired people better than me to lead these teams.
And so now I have a totally different job.
Did your vision change as you were growing your company?
Because I know early on you might think, okay, we're going to be this product, we're going
to have this goal.
But as you said, you realized that you could sell your product to more people.
And it could be useful to people in different roles than you expected.
How else did the vision for Front evolve over time?
So I think it just became more and more ambitious.
The truth is, we have a super ambitious vision today.
And when we raised our Series B, we pitched it.
And people often ask me, was that your vision since the beginning?
The truth is, it's not my vision was different before, it's just that I was thinking, okay,
first, if we can be a company with 100 people one day, then I'll be incredibly successful
and happy.
And now that the team is 100 people, I can think, okay, what does it mean for Front to
be successful and for me to be happy?
And it's always bigger.
So that's how the vision evolves.
Yeah, one of the things you've written about that's related to this is that you've said
countless entrepreneurs before you got started had warned you about something counterintuitive.
And that's that things can get harder the more successful that you get not easier, in
part because the stakes get higher.
Have you found that to be true for Front?
And do you have any examples of how that's become true?
100% true.
And I think there is, I don't know, there is just so many times where I've thought,
oh, once we hire someone, things will get easier.
Or, you know, once we're bigger, then obviously we'll have product market fits, so things
will be easier.
Or once we raise money, things will be easier, whatever.
And the truth is, there are always a million things that are broken, and more and more
things as the company gets bigger, so it's just harder.
And as I wrote, the stakes are higher.
So you just have more customers, you have more employees, you raise more money, so you
have more investors, and so anything that could go wrong has a bigger and bigger impact
as your company is scaling.
And so in that sense, I'm aware that it will never get easier.
Do you think any part of that perspective is the fact that you're sort of paranoid as
a CEO and you're always on the lookout for what can go wrong?
Or do you think that every company, things get harder and more challenging as you become
bigger and more successful?
Every company.
And I've met so many founders and CEOs, and none of them have told me, oh, just got easier
over time.
Nobody.
So one of the things you've written about as well was you wrote a blog post earlier
this year called, What Does the CEO of Front Do?
And not only did you outline what exactly your responsibilities are as a CEO of this
hundred person company, but you also broke them down and you showed exactly how much
time you spent on each of these tasks.
Why did you write that blog post?
And can you sort of describe it to listeners who haven't read it?
Yeah, sure.
So why did I write it?
It's actually pretty funny.
So when the company was small, I was doing everything.
And I think everything that I was doing was visible to everyone.
And then one day, which was maybe, I don't know, six months ago, there is a...
So I do an office hour.
Every two weeks, I have 30 minutes or one hour where I'm in a room at front and anyone
that wants to talk to me can talk to me about anything.
And so one day, someone comes to this office hour and asks me, what's your job exactly?
And I found it super interesting because I actually started thinking about it.
And it's true that when I was replaying to support inquiries or selling or hiring or
all these things, it was very visible.
And so people could tell exactly what I was doing.
And then as your company is growing, you're less and less hands on.
So maybe it's less obvious what you're doing.
So then I wrote this blog post that was just a publishing presentation that I had done
internally in front of the whole company one Monday morning explaining what my job was.
And so my job is lots of different things.
I have a few responsibilities.
So one is the financial health of the company.
So I am in charge of making sure that we always have money.
The second thing is I need to make sure that I am knowledgeable enough on the product and
the space so that we always make the right strategic decisions.
And that's not true for every founder and every CEO, but I'm still super involved with
the product.
And so that's one of my responsibilities.
The third one is I'm responsible for building and taking care of an executive team.
So at any point in the business, we need new people.
For example, right now, I'm working on a head of finance search.
And so I need to work on that while working on making sure that our existing executive
team is working well together.
Other responsibility is I need to make sure that the culture of the company is always
great.
And at the end of the day, it's, of course, a lot of people working on that.
But if the culture is that good, it's ultimately my responsibility.
And then there are lots of things that I do on a day-to-day basis.
One of them is I'm a manager.
And so I will spend a lot of time doing one-on-ones with our employees.
I'm still very involved with customers.
So I read every single NPS comment that's made every day so that I stay in touch with
our customers.
And I make the right decisions for the product and for the business.
And I work on any ad hoc problems, so any topic that doesn't have an owner.
So for example, we might work on a new pricing.
And it's not directly the responsibility of marketing or product or sales, but it's
really a mix of everyone.
And so I will ultimately make the decision on some of the topics that don't have a clear
owner.
So that's what I do in this presentation.
I explain exactly the percentage of time that I spend every week working on these topics.
And if you follow me on Twitter, you can see that my EA sends me at the end of every week
the split of my time for the previous week.
So she tells me how much time I've spent on each of these categories.
And then I usually publish it so that people can see it.
Yeah, I've seen that.
It's really cool.
I'm going to see if I can find one right now.
Okay, it's from August 13th.
You've got, it looks like 12 different things that you spent time on during this one week.
Manager, you spent 32% of your time doing emails, 12.5% of your time.
Executive hiring, 10% of your time.
Product and strategy, 10% of your time.
That's a lot of stuff.
That's a lot of jobs.
How do you remain efficient while switching contexts so often?
I think it's hard for people to just work on two jobs in a given week, let alone 12.
Yeah, so there are a few things I do to make that work.
So the first one is at the beginning of every week, I send an email to all my direct reports
and I explain what's top of mind for me and what I will be working on during the week.
And I think that helps me structure what I will do and makes me accountable.
But then I make sure that in my calendar that week, I have some dedicated time for each
of these topics.
So I know that if I don't have that, then I will never know what to work on.
And so if at the beginning of the week, my week is pretty much set on where I will spend
my time, then I feel like I'll be proactive on a lot of different topics.
Yeah, that makes a lot of sense.
Just planning ahead is a lot better than leaving things to chance.
And I know as a programmer myself, if I don't plan ahead, I will end up spending all my
time coding because that's what I like doing the most.
So one of your responsibilities is to be sort of the guardian of the financial health of
your company.
And you mentioned earlier that you raised a Series B for Front pretty recently.
You guys raised $66 million.
What's the story behind what that process looks like?
Sure.
So at the beginning of November, I think 2017, I felt great about the business.
And at the end of the day, I feel like you should raise money when you feel good about
the business, not when you've hit specific metrics or milestones that people tell you
are necessary to raise money.
So I felt good.
I felt like we had found a way to scale the business in a reputable way.
And I felt like we could invest more money on the product in order to make our vision
become true more quickly.
And so it was a combination of I feel good, and I could use the money.
And I've proved some things since our last round.
So what I did was I contacted a lot of different partners in different firms.
And I decided to put all the partner minutes in one week.
And then I was like, either it works, doesn't work.
But at least if it works, it will be a short process.
And I could get back to work.
And it worked.
So we had term sheets, and so at the end of the week, we picked one of them.
And then I moved on and started working again.
You make it sound so easy.
But I think for most people, getting term sheets to raise $66 million and doing it on
your own terms, where every investor has to meet with you in the span of one week, would
be impossible.
Why do you think Front was in such a great position to do that?
And what were some of the tricks you used to, I guess, make that outcome more likely?
Yeah, sure.
You're right.
It's never easy.
And I think we were very lucky that it happened that way.
Reflecting back, I think the few things that we did well were, first of all, we had really
good metrics.
So I've published our series, B2X, so you can see everything about our metrics at that
time.
And I think it helps a ton.
And everything else is a detail compared to if you have strong metrics, then you should
be able to raise pretty quickly.
But then I think the other thing that helped is I had built relationships with most of
the partners that I met with, and so then it makes things easier.
When you raise money, you don't need to spend a lot of time getting to know the person that
you're partner with.
So that helps.
Another thing that helped is we had a data room with all our data available, so then
I didn't spend weeks answering questions about the data.
Everything was available.
So these are, I think, a few things that helped.
And one of the challenges of raising money is that, yeah, well, it gives you, on one
hand, the resources to move faster and do more.
It also sets the minimum bar for success much higher, because investors expect you to exit
for much higher than the valuation you're at when they put in their money.
How do you think about this trade-off as the CEO?
And do you think raising money puts more pressure on you to perform?
I think I put enough pressure on myself to not feel additional pressure when I raise
money.
So I wouldn't like give anything.
So I chose Sequoia to lead our Series B, and Brian Schreier joined our board.
And I think that maybe earlier on, I thought that having a board member could be scary
and would add pressure.
But in fact, we're already in the same team, and so if anything, so I've been working with
him for nine months now, I think.
And it gives me so much energy, because he's great, he's very talented, and I think I just
want to be a better version of me so that he is proud.
And I think that is positive for the business, and his experience is very positive for the
business.
So I don't think there is enough thing that is negative.
I think the mistake would be because you have money, you spend it.
And that's the mistake that I'm trying not to do.
What are some of the other advantages to raising money and having these world-class investors
on your team besides just having the money in the bank?
There is always a network of people that go with every fund.
Sequeya has a strong network, so it's useful.
They have resources internally that can help you, so for example, they have an amazing
recruiting team that helps me whenever I'm doing a new search.
They have events on specific topics, and so either me or other people in the team go to
these events and learn a ton.
So yeah, they can help sell candidates when you have late-stage candidates, and if they
believe that your company is great, then hearing from an investor that they think your company
is great helps a lot.
Yeah.
The reason I'm asking about fundraising is because I sort of oscillate between having
VC-funded founders on the podcast and having self-funded bootstrapped founders on the podcast.
And it's a lot of conflict between these two camps.
I think the bootstrappers tend to believe that raising money from venture capitalists
is selling your soul in a way.
You're giving up control of your company, you're giving up your dream, and it's oftentimes
a bad deal that founders regret, whereas the VC-funded founders tend to believe that you
can't build a significant or big company without raising money.
What would you say to a founder who's on the fence between these two camps?
Sure.
So I mean, first of all, I don't think that raising money is good in itself.
If you could generate enough money to never raise money, then obviously do that.
But now the question is, if you don't have a choice, and so the two choices that you
have is either you don't grow as fast as possible because you don't have money, or you try to
grow as fast as possible, then it really depends on what motivates you as a founder.
For me, as I said, I care about having an impact both on customers that are using the
products and on people that are in the company.
So the bigger the company is, the higher the number of customers we have is than the happier
I am.
And so for me, growing quickly without threatening our culture is incredibly exciting.
And that's what I want.
And so we're a young company, but we've been growing pretty fast.
And I would have never been able to grow that fast without capital.
And if I could have, then I would have done it.
But it wasn't possible.
So that's how I would think about it.
It's funny because raising capital helps you grow more quickly, yes.
But the reverse is also true that growing really quickly helps you raise capital.
And it helps you with a bunch of other things too.
Helps you with hiring.
I've talked to a lot of companies with co-founder issues, and it's almost always the case that
these issues prop up when things aren't going that well and growth is stagnant.
And so in some ways, growth is the answer to a lot of problems.
Yeah, that's true.
But then you could also think about companies that just want to have a lifestyle business
and they don't want to be a billion-dollar company.
And I think that's totally fine as well.
I think people should just do what makes them happy.
For some of them, it's being in a high-growth environment, and for some of them, it's not.
Let's talk about what makes you happy, Matilda.
You mentioned that there are two reasons that you started this company.
One of them is to build something that improves your customers' lives.
And the other was to create a company that both you and your colleagues could actually
enjoy working at.
So what does the culture look like at front?
It's always a tricky question to describe the culture in just a few words.
But there are a few values that we have that I think we would describe really well.
Our team, so one of them is low ego and combined with high standards.
So those are two values.
So I think we're a team of talented people that are super humble and know that there
is so much they don't know.
This third value is care.
I think we're a team of kind people that care about each other and about our customers.
Transparency is our, I think, most surprising value in a sense that when people join, they're
always so surprised at how transparent the company is.
So it means lots of different things.
It means that employees always know what's happening.
There are a few examples of that.
We have a public roadmap so anyone can see what we're working on.
Every Monday we do a presentation.
We go over all our metrics.
Everyone knows the runway we have, the amount of money we have in the bank.
Everyone knows the feedback that's good and bad from our customers.
And at an individual level, everyone knows how people and their manager feel about them
and their manager knows how they feel about them.
So there is a culture of radical candor.
So that's what I would say.
Now we have two offices.
We have one in SF and one in Paris.
So I think our culture is also defined by the fact that we have these two cultures.
We like board games.
We do off-sites, company-wide off-sites twice a year where the whole company goes somewhere
for a few days.
So that's how I would describe the culture in just a few seconds.
What's your favorite board game?
So I have a new one, Predo Rico.
A lot of people know Settlers of Catan.
So it would be a version of Settlers of Catan without the dice.
Because the problem with the dice is that there is too much luck.
So much luck.
Yeah.
So I love Settlers of Catan because I think it's an entertaining game.
But I don't like it that much because I think there is too much luck.
And so Predo Rico would be the same but without luck.
It's funny because after a game of Settlers, you can sort of forget about the dice rolls.
You just see the results and you don't really remember how much luck went into it, which
I think is analogous to running a business in some ways where a lot of things happen.
And of course, you're working as hard as possible.
But there are some lucky things that happen too that are really easy to forget about.
What do you think have been the luckiest things that have helped you get to where you are
with Front?
Yeah.
So first of all, I think that I've been incredibly lucky.
I don't think that there's been a few things where we've been lucky.
Overall, we've been super lucky that I met my co-founders.
Super lucky that our first employees worked out.
Super lucky that we went into AC.
Super lucky that the first customers that we had were very patient and gave us enough
feedback.
Super lucky we got funding from the people we got funding and then helped us.
There is just so much.
I was very lucky to have people help me along the way.
I have amazing mentors, amazing people that have believed in me and told me about it.
I have an amazing husband who believes in me and tells me every day.
So just a combination of a lot of things.
Has there ever been a time where you were looking at your business and thought the ship
was screwed?
I don't know how we're going to get out of this one.
And you weren't really sure that Front could survive?
Yes.
So that's the spoiler that it happens every month.
Oh, wow.
What do you think is the scariest moment where you've had those thoughts?
I don't think there is a...
I'm just used to it.
So I don't think it's scary.
It's just the reality.
Like those thoughts that I have all the time that I've always had and I think if I keep
having them, then that's how we'll make the best decisions.
Let's talk about the business model behind Front and some of the numbers and the decision
making that have gone into that.
Because I know to get Front to the level it is at today, you've got to put a lot of thought
into your pricing and into what kinds of customers you want to target and what kind of customers
you don't want to target.
How have those decisions evolved over time?
So we always had a price per user per month or a price per user per year, but then very
early on we invested in a system that would allow us to iterate on our pricing pretty
easily.
So we went through 17 iterations of our pricing already.
Wow.
What did you learn from that?
Just that pricing is super hard to get right and even today, I think it's completely wrong.
So you just need to...
I think investing in a system that would allow you to change it pretty quickly is a super
great investment.
What about the competition?
How do you think about other players in the space?
Because for most businesses, they're paying $5 or $10 a month for something like Google
Apps.
They're paying for Outlook.
They're paying for other help desk software.
How do you make decisions about the pricing?
How do you experiment with your business model at Front knowing that you're part of this
wider competitive landscape of companies and products that charge their own prices?
Yeah.
So it's true.
At the same time, you should think about pricing as a return on investment.
I think email can be so critical to some teams that they would actually be willing to pay
a lot of money if the tool was significantly better.
So yes, we compete with Gmail and Outlook.
We also compete with, as I said, help desk solutions.
And then on one hand, help desk solutions are super expensive.
On the other hand, email solutions are super cheap.
And so our pricing is pretty much in the middle, and it's tough.
I mean, it's tough in a sense that it's never right, but you have to accept that it's never
right and you have to keep iterating on it.
Have you guys ever had any big disagreements over major decisions around pricing or your
product or just the direction that you should head in with Front?
And if so, how did you resolve those issues?
So first of all, the fact that we all use Front at Front.
So everything is shared, every customer feedback.
And I think the reason why we've never really had a disagreement on the product is because
we use the product.
So we know what you need to improve, and then we see what our customers like and don't like.
So we know what we need to work on.
And so that's something that I would recommend to any company, which is the more you can
share the feedback of your customers and leads to enter a company, the more alignment you'll
be able to have.
So Front is one good tool to do that, but there are other ways you can achieve that.
I think transparency in general is just the best way to create an alignment in your company.
So I don't think there's been a ton of disagreement.
We agree, and then we make mistakes, and then we change it.
But I don't feel like we've spent a lot of time at Front arguing.
We've just spent a lot of time trying to fix problems.
Let's say you could go back in time to the very beginning of Front when you guys first
started working on it.
What would you tell yourself and your co-founder that you didn't know at the time?
I think I would just tell myself that it will be hard, and I shouldn't think too much about
the fact that it's hard along the way.
Well, you've got a time machine here, Matilda.
You wouldn't tell yourself any answers to specific questions, any decisions or predictions
about the future or stuff like that?
I don't know, I would say move to San Francisco at that time.
It was better, and it took a lot of time for us to convince ourselves that we should make
the move, and so I would say that.
What if you could go forward in time and ask the future Matilda any questions, and she'll
tell you the answer?
What would you ask yourself?
I don't know.
I would ask myself if I'm still happy doing this job.
Oh, yeah?
Yeah, just because I want to make sure that it's always true at any time in my life.
It's such a simple question to ask yourself, but also such a good North Star to have.
I mean, it's the basics.
Am I happy?
And if not, I need to change things up.
And I think it's tough sometimes because I guess different incentives can come into conflict.
For example, if on one hand you want to make your customers happy and you want your company
to succeed, but on the other hand, you want you and your team to be happy, things might
be in conflict, which one wins?
So that's the thing.
When I do this presentation at the beginning of every onboarding session, I do tell them
that I never want to compromise and I do never want to compromise.
And I do think that happy employees lead to happy customers and happy customers lead to
happy employees.
So I actually don't think that you need to make a trade-off.
That's fascinating.
How do you balance things so that you never have to make that trade-off?
That sounds very hard to do.
I don't know if it's hard.
There are some companies that will just focus so much on customer happiness.
And so, for example, for us, it means that everyone does support.
Every week we highlight a customer.
It's just a choice that we've made.
It's not good in itself.
I think it's totally fine if you don't have a customer-centric company.
You can have an employee-centric company.
You can have a product-centric company.
So I don't necessarily think that you need to do a trade-off.
You've been incredibly successful as a first-time founder.
You've grown your company to 100 employees.
You've raised millions of dollars.
You have thousands of paying customers.
What is your advice to people listening in who are considering becoming first-time founders
themselves?
So one is do it.
You should just get started because if you're in and just make a leap of faith and nothing
that has been built was obvious, otherwise it would have been built 10 times before.
So that would be number one.
And number two is as I've worked with entrepreneurs, one thing that I've realized is once you start
building your company, focus is so important and being organized is so important.
So one thing that I find surprising is I help entrepreneurs and usually they keep me posted
on their progress.
And so some people will keep me posted every week or every month, it doesn't matter.
And the format of their email is always the same.
So these are the metrics that we track.
And they always send it to me at, I don't know, same day or whatever.
And there are others that don't do that.
And I can tell you now that I've followed these people for a few years that every single
time a founder does it in such a structured and focused way, their company works out.
And every time they don't do it, their company doesn't work out.
So obviously, I'm not saying that it's because you will do it, your company will be successful.
That's not at all my point.
But I think the ability to be super focused and to face the reality and to just be organized
will be a huge reason why you will succeed or not in the early days.
That's great advice.
Well, listen, Matilda, thank you so much for coming on the show and sharing your story
and your learnings and your wisdom with all of us here.
Can you tell listeners where they can go to learn more about what you and your team are
up to at Front and also what's going on in your personal life?
Sure.
So you can go on frontup.com and you have a link to our blog and I think that's the
best way to know more about Front.
And I have a Medium blog and I post a lot of things.
I have a Twitter account that I use every other day, maybe.
So you just have my name and Twitter and Medium and you'll find a lot of things in it.
Alright.
Thanks so much again, Matilda, for coming on the show.
Thanks for having me.
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