Smart Bear Live 8: Edwin from

Welcome back to Smart Bear Live … the show were Jason speaks with entrepreneurs looking to improve their businesses. In this episode, Jason talks to Edwin from MeetingKing.

Listen to this episode if you want to hear about a founder who has a product and users and paying customers … and is trying to figure out how to take his company to the next level and grow faster.

PRODUCER’S NOTE: Do you wish you could hear Smart Bear Live episodes more often? Well maybe you can help – the show needs a new producer! I’ve loved being part of the show, but now that I’m part of the growing team at Moraware, I don’t have time for a serious podcast. If you are passionate about business, good at writing, decent at scheduling, can learn to edit audio, and want to help Jason share more interviews, then contact me to see if you could be the next producer of Smart Bear Live. –Patrick


Automated transcription services provided by:
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Edwin:  At MeetingKing, our goal is to help the world get rid of bad meetings. I got annoyed with bad meetings that I attended and also the
meetings that I chaired I was not very satisfied with the results. So I analyzed why is that? Why are the meetings so bad? If you look at the
problems, it comes down to two issues: people are not prepared, and there’s no follow-up. And when you look at the tools that we use, I mean we’ve made
so many technological advances, but really to manage a meeting there’s not a practical tool available. We use email; we use Word; we use task manager;
we use a file sharing tool. And to combine all that information, it’s just not practical. So in the end, we do not make an agenda so nobody’s prepared
for the meeting. We do not keep track of the tasks that we agreed upon so things don’t get done. Everybody just scribbles their own things on a piece
of paper and three months later we discuss the same issue again and don’t make any progress.

So that is a little bit of the philosophy behind MeetingKing. We started
with the product about three years ago, development, a year later we
released it. So let’s say about a year and a half, the product has been out
for real. We did an interview before, Patrick, together with Bob. A lot has
happened since then. We now have somewhere between 20,000 and 25,000 people
that have created an account and get a decent amount of traffic on the
website. People are willing to pull out a credit card.

Jason:  So how many of those 20,000 people are paying customers?

Edwin:  I hope you don’t mind if I don’t go into details, but hundreds
of them. So conversion rate percentage, of course it can always be higher
and we’re doing a lot of stuff to make that higher, but it’s in line with
other applications.

Jason:  Yeah, one percent conversion rate is pretty normal.

Edwin:  I’d say actually I think I’m a little bit above that.

Jason:  So what are your challenges right now that you want to talk

Edwin:  Yes, the challenge that I have is the product does a lot of
stuff, it does meetings, and it organizes information. What should I focus
on in my communication? What is a simple message to convey either both or
one of the things that I can pull people in?

Jason:  Okay, and probably pull people in that convert, right? You
don’t need just more traffic; you want more people that are going to buy,

Edwin:  Correct. That’s of course the ultimate goal.

Jason:  Who is buying it today? Is it smaller business? Is it big
companies? It obviously can’t be a single person because that person
probably doesn’t have many meetings. On the other hand, if it’s a huge
company, maybe they do need this although it’s hard to imagine them
replacing a task tracker at a huge meeting with a small tool. So who is
buying it today? Is that the kind of person you want to buy? Or who is it
that you want to be the buyer?

Edwin:  Okay, I have different types of customers. So on the one hand .
. . and those are the people that are more interested in the specific
meeting part are churches, nonprofits, and small organizations. I have
schools and businesses. Now most of the businesses are small to medium-
sized businesses. I’ve had some very good conversations with a large
insurance company.

Jason:  What do you mean by a medium-sized business? How many employees
would a medium-sized business have in your definition?

Edwin:  Small to medium, so I have people that have teams of five
people in their company, 20 people in their company up to 200.

Jason:  Okay. I’m just clarifying. Some people have different
definitions of that.

Edwin:  Yes.

Jason:  For example, like in America, small business is up to 150. I
mean they have these definitions. So anyway, it sounds like it’s almost
completely small organizations, under 1,000 people, and you listed a lot of
folks who traditionally have low budgets.

Edwin:  Correct.

Jason:  Nonprofits, schools, churches and so on, which of course is
problematic in general unless that’s what you want. So it sounds like
you’re getting people who have low money. Not too many people involved in
the whole organization, certainly not in the immediate group, and they just
want to get a handle on things, which makes sense.

If I collect all that together and call that all small business,
which is a little unfair because of course they are different in how you’d
get after them and so on, but for now, if I collect all that and say small
business and organizations, is that what you want to target? Does that make
sense to you and you’re like yes, I can get a million of those guys just
like Fresh Books did and so forth? I’m going to do just like that and get a
million of those people over the next 5 to 10 years? Or do you not want
those customers?

Edwin:  That’s actually why we’re having this discussion. Those
customers are fairly easy to sign up, but if I look at where most of the
money comes from, and those are the larger licenses of five or ten users,
that is according to your definition then the small businesses and small
businesses include actually the Mexican Stock Exchange, Chamber of
Commerce. In Spain I have large companies.

Jason:  The question is do you want those five to ten license guys? Do
you want to try to make a thousand-license product? Do you want to go after
the ones that are even smaller? What is it that you want to do for your
business? You said you get more money off the things that are actually
businesses and the groups are at least five people, so is that where you
want to focus?

Edwin:  I think that at the moment I should focus on those. Eventually,
as it always goes, you have a lot of ideas on how you can grow the
business. Eventually I would like to go into bigger companies because I can
come up with a lot of arguments why this would be a great tool for a big
company. But big companies move slow. It needs to be more mature, so let’s
focus on the small-sized companies where my ideal customer and the people
that pull out credit cards is in general the CEO.

Jason:  Okay, so that’s a very small company in which the CEO is
pulling out the credit card for meeting software because even people with a
hundred people, the CEO is not the person pulling out a credit card for the
meeting software. They’re doing something else by that point.

Edwin:  I tend to disagree. I have a couple of guys that I interact
with very frequently. They are the CEO, and they give me a lot of feedback.
They’re early adopters. They really like the tool. They are so happy that
they finally have a tool to manage their business.

Jason:  If I’m managing my whole business with this tool, I don’t have
100 employees. That’s what I’m saying.

Edwin:  Then I communicated that incorrectly. I do think that most of
my customers are small/medium businesses. I have people from schools; I
have people from churches, etc. But if I look at my signups, most signups
come from small businesses.

Jason:  Okay.

Edwin:  And just to clarify it a little bit, small businesses, I have
people that run software companies; people that actually run a chain of dog
grooming saloons; people that run a bunch of French . . .

Jason:  I get it. So part of the dilemma is there’s meetings; there’s
the meeting management at the meeting; there’s preparation for the meeting;
then there’s follow-up from the meeting.

Edwin:  Yes.

Jason:  And to me, trying to replace someone’s to-do software or their
actual organization software? That’s a challenge. For most people, to-dos
come from a lot of places. Meetings are definitely one of those places, but
email is another primary way that that comes in. And for some people, they
want to have one tool for home and work and so you have even more use cases
and there may even be things that are shared and not shared. You kind of
get into all this stuff when you get into to-dos or project management in
general, which are not really the same thing, right? But both things,
product management and to-dos, are entire industries on their own and for
good reason:  because it’s really complicated, lots of segmentation, lots of
personal preference.

And that’s also true on the business level. Asana’s a good example of
something that’s trying to be sort of project management, lightweight
project management, definitely to-dos, definitely shared, definitely for
small teams, and they’re doing really well there, and they’re also trying
to replace email and kind of get in the way of email. So that’s an example
of a company trying to do that and be sort of unique in that way, and of
course they don’t particularly have meeting management built into it.

But what I find, and we use Asana and I know other people use Asana, but
people generally do have Asana open during the meeting and that is where
the to-dos are placed so that there is follow-up because this goes right
into the shared project/to-do system and that’s how that gets satisfied.

So as you get into to-dos and follow-up and management, that side of you’re
talking about? As you get into that side, my feeling is, if I’m giving you
a gut reaction, my gut reaction on that is “whoa, that is a whole universe
of stuff and it’s going to be really hard to make something that is unique
and awesome.” And Asana is obviously one of a hundred companies doing
something like this. On the one hand, it’s massive. I grant you it’s

On the other hand, it’s a whole universe and you’d need an interesting
perspective on why you should go attack that market and face all that
competition and noise and everything that’s in the market. Now as you scoot
over to the meeting side of things . . .

Edwin:  May I . . .

Jason:  That becomes more interesting to me because for example, we had
the top product person at Asana at our office showing us around and talking
to us about how we use it. And in particular, we talked about how we use it
for meetings. And so they described it, “Well, we often use it like this.
We’ll put a meeting in Asana in the following way and use tasks in the
following way,” and basically showed me how you can use it that way and
it’s useful that way to an extent, but it’s really clear that it’s not
designed for that and that it’s sort of a hack or a bolt-on or a way to try
to put it in when it’s not really a part of the tool.

And so if you have something that makes meetings truly good, and maybe some
of that is scheduling because scheduling’s always a bear; prep is
definitely good, as you said; maybe it integrates into some other tools,
I’m not sure for follow-up, but the more you get into that meeting side of
things so that rather than sitting in front of Asana or a Google Doc that’s
shared or as you said just notebooks and pencils, that we have something
that’s actually making this meeting move quickly. We’re hitting the agenda.
We’re not running over. We’re hurting people who come in late so that they
stop coming in late. That’s a big meeting problem. What happens if someone
can’t make it?

There’s all these things that happen in a meeting that are in fact really
annoying, and no tool that I’ve seen, and what I mean is like Asana and so
on, addresses those things. Getting through the agenda is a really
difficult thing and time boxing stuff and setting conversations aside to
come back to. These are all really important things that happen in meetings
that people are generally really bad at managing, and a tool like Asana
certainly does not help you manage that.

So the more you move into addressing the problem meeting specifically and
not about managing to-do tasks and certainly not the whole business, but
even minor things, the more interested I personally am that you’re carving
out something interesting and novel. So when you’re thinking about
marketing positioning to me, that side of it is the interesting side of it.

Edwin:  Correct, I fully agree and the name MeetingKing already says
that my initial focus definitely was on meetings, right? Now what I’ve
found is that especially the larger licenses, 10- and 25-user licenses, in
the beginning I lost those customers after a couple of months. Their
challenge was that they couldn’t manage the tasks afterwards. I had all
kinds of filtering functionality in there, but it wasn’t very practical. So
with that feedback, we worked on the new version. The new version has
actually a very, very strong task manager.

I would like to make the argument that MeetingKing has a better task
manager to manage your tasks related to a general manager than Asana. The
reason is that let’s say you have a general management meeting. So what you
can do is you add a group or a tag to the meeting, general management. And
then you and the CFO and the marketing guy and . . .

Jason:  Hold on, wait, hold on.

Edwin:  Yeah?

Jason:  This is too complicated because we’re talking about marketing
messaging, right? So give me in one sentence why your task management is
better than Asana, or maybe two sentences. But you don’t have all this time
on your homepage to describe how it works.

Edwin:  That’s exactly my challenge. That’s why we’re having this

Jason:  It’s not clearly better if you can’t articulate it really
briefly. Then it’s not clear why it’s better. So like for example, with
Asana, just to give you an example, they would say what’s better is they
reduce emails because there’s all kinds of emails of coordination that you
don’t have to do when it’s coordinated in the tool. And on top of it, it’s
real-time and all these other things. So that’s a very simple way of saying
it’s task management, but it’s getting rid of emails that of course no one
wants emails. So what is your nutshell? Because saying something like, “My
task manager is better than Asana,” or “It’s better than Remember the
Milk,” or it’s better than . . .

Edwin:  There are a million others.

Jason:  There’s a million, but people love them. They have many, many
man-years of development and customer development in them. So to just say
look, in the last three months we made one that’s way better? That’s fine,
but you must have a simple way to articulate why that is. It can’t be some
really complicated, detailed description of why that is.

Edwin:  Okay. MeetingKing is like an accounting system for all your
discussions and your tasks. In an accounting system . . .

Patrick:  Can I interject a second?

Edwin:  Sure.

Patrick:  This is Patrick. I’m looking at the homepage. Personally, and
Jason, correct me if you disagree, but I see this as a mistaken features
and benefits. And even what you were just going into is a feature. I don’t
care about features per se, I care about the benefit. So I don’t want . . .
the first headline you have is collaborate before, during and after
meetings. I don’t want to collaborate before, during and after meetings; I
want a successful meeting. So how can you translate the reason I have to
collaborate before, during and after meetings into the feeling I’m going to
get of having a successful meeting? And same with all information in one
tool and one place. I don’t care about that except for the result that it’s
going to get me.

Edwin:  No, and I completely agree. My messaging at the moment is too
much on features and not enough on the user point-of-view. What do I gain
from it? That needs to be improved. That’s why I say okay, I have these two
main areas that the product does. And what I was just saying is with
MeetingKing, I can say . . . like in an accounting system, you can say, “I
want to know exactly the expenses that Jason made for product ABC related
to marketing in that period of time.” And that is what you can do with
MeetingKing. If I run a chain of restaurants, I bundle all my information
that I have from one discussion with the manager of restaurant 25. But in
that one discussion, I talk about HR; I talk about inventory management; I
talk about local marketing campaigns.

Then, at the end of the week or during the week, I have ten meetings with
ten different managers. At the end of the week, I sit down with the VP of
marketing at the corporate level. And what you can do with MeetingKing is
then filter out from all of these meetings everything that has to do with
marketing activities, and the same for HR, etc. So you have this cross-
filtering or cross-information. It’s bundled in different groups. You have
your general management meeting and in your general management meeting you
talk about product development, about marketing and about finance.

Jason:  All right, but you can’t talk for five minutes then say . . .

Edwin:  I know. I know, that’s . . .

Jason:  All you just described is that things are tagged and I can look
at things by tag instead of by meeting. I get that, but that’s kind of any
to-do or project management system has tags and you can view it that way.

Edwin:  Well, it goes a little bit beyond that because these tags, also
you can define it as a project group and a department. So you have your
marketing department, and everything that’s created with the marketing tag
will be visible to the marketing department. So it goes a little bit beyond
just simple tagging.

Jason:  Okay, but you have people that have only got five people using
it. Is that what they’re doing? The five people are doing all this stuff?

Edwin:  Oh sorry, so the business model . . .

Jason:  That’s not what you described.

Edwin:  The business model is that the organizer has to pay. So
companies that have a five user license, it means that they have five
organizers, but they probably have something like 20 or 30 people on it.

Jason:  Okay.

Edwin:  Yeah, like I said, the marketing guy can then filter out
everything that’s relevant to him. The filtering is very simple and I even
want to make the filtering because we have functionality for file sharing.
If you make an agenda, you can include attachments in the agenda. So the
file sharing, we can use the same filtering method. So organize your
information; that is the USP.

Jason:  Okay, organizing information is not a unique selling
proposition. I’m still having trouble, because you’re all over the place
with stuff. I mean now you’re telling me you’re into file sharing. I’m head-
smacking because it’s like oh my God, now we’re going to compete against
Box, too.

Edwin:  No, actually I want to integrate with Box. I don’t think I
would want to compete with Box or Dropbox. No, no, no.

Jason:  I think looking at the problem with trying to find your
marketing message is you yourselves do not know what it is that you want
your product to be and want your customers to think of it and what benefit
they want from it. Like for example, you said you had some of these bigger
accounts and you lost them because there wasn’t sufficient task management.

Edwin:  Right.

Jason:  So you said, “Well, I can now do much better task management.”
In that case, you’re a task management system. You’re a project management
system. It is a multi-departmental project management system, which is
really cool, because it means everybody can do all their stuff and see
exactly the slices of things they need and some things that they’re
controlling, some things that they’re viewing and so forth. It’s integrated
through in-person stuff like meetings as well as electronic stuff I
imagine, because if this is just meetings them obviously you’re missing a
ton of other stuff that’s related to the project like email. So presumably,
it has to cross into all those things as well.

So I guess to me, again, my visceral reaction to all that is that’s a
rabbit that you’re just going to chase forever. So you add all this stuff
where files can be attached or referenced from Box and that can be tagged.
Again, everything you’re describing to me is about project management and
task management. Everything you described to me is in that. In fact, it’s
the whole point of the meeting in the way you just articulated it is in
order to turn into things that you can then pull up later or track whether
they happen later, and then also cross-cut so you can report, for example,
to another department how the things relevant to them, how that transpired.

Edwin:  Yes.

Jason:  So that’s still project management where meetings is just one
of the ways in which data comes into this thing. So that’s the sort of way
I interpret what you’re doing, because although it’s called MeetingKing,
you’ve not talked almost at all on this whole call about anything about
meetings. It’s all been about project management. And when you lost
customers due to not having project management, your response was to make
project management.

But to me, that’s a never-ending thing. You’ll make a certain set of
features, then a certain set of customers will be satisfied with that
amount of features. But there’s always more, because project management is
this ridiculously large thing to go down, especially if you’re just one or
a few people doing everything in the company. There’s just too much to do
when it comes to that kind of project management.

Edwin:  We’re on the same page. When I said that we’ve improved or that
I added functionality for the task management, I am talking about the
interface, the accessibility of functionality that we had because tasks and
meetings go together. If your meeting doesn’t result in tasks, you might as
well not have had a meeting.

Jason:  Well, that’s not true. I mean there’s all kinds of meetings
where there isn’t necessarily a takeaway for everyone.

Edwin:  Yes, I know there are informational meetings. But I think . . .

Jason:  Another one for example, sometimes on one-on-ones, there’s
specific tasks to go do but sometimes there’s a lot of status and a lot of
broad things a person’s working on which you wouldn’t necessarily
categorize as a task or a project.

Edwin:  Right, but you cannot make . . .

Jason:  There’s lots of things.

Edwin:  You cannot make a meeting tool that you use for all your
meetings if you don’t have task management. Suppose only half of your
meetings would have tasks in them, you cannot use two different tools.

Jason:  See, here’s where I’m disconnecting. I hate meetings and I
think we run meetings very poorly most of the time.

Edwin:  Yes.

Jason:  And I think that’s the fundamental observation you had making
this company.

Edwin:  Yes.

Jason:  I feel like there’s a lot to do in solving that. And if you’re
going to insist that I use a certain task manager in order to solve it, I
can’t solve it. In other words, if I’m thinking about this just from a WP
Engine perspective for a second as a potential customer, when you come up
to me and say, “Meetings are awful because half of them don’t even have an
agenda, and the ones that do, you don’t stick to it and they go long. And
the takeaways that people have to go do? Who knows if they went and did it?
No one checks them.”

When you have weekly meetings, which many of my meetings are weekly,
and if you’re talking about GMs, many of your meetings are periodic like
weekly, like daily standups or weekly one-on-ones or other kinds of sinks?
In those meetings, often you want to know, “Wait a minute, what happened in
the last meeting? Did we do the things we said we were going to do from the
last meeting?” There’s a lot of callbacks to the last meeting in those
kinds of periodic meetings.

Edwin:  So may I . . .

Jason:  When you start telling me about all those pain points, I think
yes, yes, yes, this is such a pain point. I want to solve this so badly.
You’re right. You’re right. Tell me more. I want to solve those things. And
again, I’m talking about pain benefits now like Patrick was saying. I don’t
care about what the software looks like yet.

Just yes, that’s a problem. If that software solved those things; if
it made my meetings run on time; if it made sure we got through the agenda;
if it helped make sure people would come prepared; if it let me tie one
meeting to the next and ask did we do it? Those sorts of things, if it did
that as benefits, forget about how, I don’t care how, I’m really

But as soon as you say, “Yeah, but the tasks that come from there,
you have to manage that in the tool.” So now I have to wonder whether a
task is in Asana or whether it’s in this tool in order to do project
management or task management. Suddenly I’m disconnected and I say look, I
can’t have two project management tools for everything. It’s got to work
together somehow.

So if you can solve the meeting part and have the meeting part be more or
less wholly solved, I am so in. But as soon as you say I’ve got to take
over more parts of project management or I can’t really give you the
benefit, I’m out. And I wonder . . . now I’m just one data point, of
course, but again, if you have a really tiny company they probably can do
all the task management inside you because they can probably use anything,
right? But as you want to go upstream with the larger companies with more
budgets, which I think is what you’re saying you want to do, focusing on
the thing that is unique about you which is the meeting component to me is
the interesting part, not the tasks.

Edwin:  So then it was not my intention to go all the way on the tasks
without spending a lot of time on meetings because I think that that is
where we really have something unique to offer. So just to close off the
task part at least for the time being, yes, I would like to create an API
integration, so if you use Asana, great, for your tasks.

Jason:  No, no, no, because there’s too many project management things
and you’re only one or a few people. You can’t integrate with everything.
It’s got to be something where . . .

Edwin:  There are tools like Zappier or If/Then or something like that.
So if I make an open API, you can make a bridge for the tool that you use.

Jason:  It’s too complicated. I’m looking at your own homepage of who
your customers are:  businesses, schools, nonprofits, towns, churches and
clubs. Nobody can do an API.

Edwin:  No, they can’t. They can’t. And maybe . . .

Jason:  We should stop going down this road, because I think the
point’s made and it’s fine. So the thing is, what’s on the homepage? To me,
solving the problem of meetings is really interesting. And the more you can
stick with that and not get off into all this other stuff, the better. And
so if I’m then just going down your homepage, and again, just reacting to
what’s on it with regard to the question, “What could the positioning be?”
Or “What could it tightly be?”

So I’m looking at it, and the first thing I think is the design is simple.
It’s very easy to read and it also feels very small, like a small business
and for a small business. And that’s probably good. I mean right now that’s
who you’re selling to, so it’s nice to have a good, friendly thing. And in
fact, saying, “Look, hey, we’re a small business but we’re doing something
really interesting” I think is a good message. So to the extent that you
want to keep at that particular demographic, I think that’s fine. It
doesn’t have to be a super high-gloss whatever, especially with the types
of people you listed who are buying it. I think this is accessible. But
looking at it, so MeetingKing . . .

Edwin:  Would I be able to attract other people if the design would be

Jason:  Some people think the design matters a lot more than that. I
think this looks like no designer made this, right?

Edwin:  Thank you. I did it myself.

Jason:  Right, which is again I think a simple, honest, accessible
thing as a result. That’s the result of that: it’s clean and easy to
access. And so I think you can’t charge a lot with this design, but you’re
not trying to charge a lot. You’re trying to get small businesses who don’t
have a lot to give you anyhow, so I think for now that’s fine and that you
don’t need to spend a lot of effort on that.

So if I’m looking, MeetingKing’s obviously a brilliant name. I love
it. It’s kind of already obvious what it does, which is great.

Edwin:  Well yes, you say that, although a lot of people think, “Oh,
yet another WebEx or GoToMeeting.” And even if they didn’t read this stuff,
they have it planted in their head that it is yet another WebEx.

Jason:  Okay, good. So this gets to the headline, which says more
productive meetings in three steps. Now the headline I don’t like, and the
reason is anything like productive or simple or saves time, all these
things, they’re very generic. They don’t paint a picture in my mind how my
life will be different.

I haven’t looked at the video yet, but I should be able to understand
from the headline and get some kind of emotional reaction to the headline.
And actually, I don’t want to take three steps. I would really rather not
take steps; that’s actually work. So that doesn’t sound good, right?

Edwin:  Okay.

Jason:  So to me, I like a really emotional thing. And also you can use
this emotional thing to show that you’re not WebEx or not Screen Share. So
for example, we talked just now about all of these different things at
meetings that are horrible, right?

Edwin:  Yep.

Jason:  Are you tired with meetings running late, but not getting
through the agenda? Or around you have a meeting, then everyone leaves and
comes back in a week and forgot everything that happened and nothing got
done? These are things that I think a lot of people would nod their head
and go, “Yeah, that’s stupid. That’s horrible. Yes, that’s me.”

Edwin:  Correct, correct.

Jason:  We’re not going to wordsmith it on a call like this, but I
wonder if something like that where you evoke this thing in someone that
goes yeah, that sucks, that would to me be a better grabber than something
very generic in promising there are steps coming my way that I have to do.
Let’s just evoke the pain, right? Then it’s like oh, yeah, that sucks.
Wait, this does something for that?

Then you have your thing, your MeetingKing, your assistant to help
your company or school or club have more productive meetings. Now you don’t
have a lot of space right here if we’re keeping your design, so I get it
that you probably want to show people who are in schools and clubs that are
not businesses, “Hey, this is for you too.” But you also just said on this
call that eh, business is where you make your money. So what I would
suggest is you could keep that list down below, but if you want business
then say business and don’t list the other ones.

Edwin:  Right. The challenge is it is such a horizontal product, how do
you . . .

Jason:  No, it’s very easy. You just don’t do that. You say it is this.
You decide this is my target customer, which you started doing on this
call, right? You said the best customer is . . . you can’t have one
employee because meetings are just too easy and you don’t really have them
formally. You can’t have 5,000 employees. You could, it’s just we’re not
targeting that.
The whole point of this is not to say you can’t have these other
customers, but rather honing in on which customer right now is perfect. So
of course if you have a big company, you can use it. Of course if you’re a
club, you can use it. But we’re just not going to name them as ideal.

So you say now, ideal is the whole company has between 20 and 500 employees
and the organizer generally works between 5 and 15 people within the
department and the same number of people outside the department because
when they’re in that state they really have a lot of stuff to meet about
and organize and repeat. Their life is just hell. That’s the perfect

You see what I mean? You do that and you build this really ridiculous
customer for whom they have every single pain you can imagine and they
really need the help. And then have that person in mind as you write
everything. So what would you write where that person would go, “Oh my God,
that’s me?”

So you wouldn’t say company, school or club to hit that person. And maybe
not even assistant. Maybe. That’s an interesting word, assistant. But with
that person in mind, it helps you actually track meeting-to-meeting or
follow-up from one meeting to the next or under managing tasks, it’s not
really managing tasks is it? It’s more like holding people to account
meeting-to-meeting or things that are related to each other and thread
together . . . I’m not sure. There’s these kinds of words like that.

Like for example, if I’m just looking at these bullets here, “Tasks from
previous meetings are automatically added to your new agenda.” I get that,
but what I’m really trying to do though is not auto-add tasks to agendas in
meetings. What I’m really trying to do is follow-up or double-check or how
did we do or really quickly, only five minutes, can we double-check and can
people come prepared so we can double-check whether we did what we said we
were going to do, but also we only take five or ten minutes to do it?

This is obviously too many words, but do you see what I mean? That’s the
thing that I want to hear in the text here is that you’re going to give me
that. And so saying literally “tasks from previous meetings are added to
this meeting,” that’s not really telling me that. That’s not telling me
that I’m going to get that. But listing these things? That sounds awesome.

Edwin:  Right, yeah, nothing will fall through the cracks. Nothing will
drop off the radar.

Patrick:  You can channel Cathy Sierra on this and say that the users,
you become a Meeting King. You know, you want your users to be badass, not
you be badass. All of these are about the product being badass. So if I
were a badass meeting person or if I were a Meeting King, my agendas are
stuck to. My minutes get written after my meetings. My tasks get done
afterwards. So consider maybe wording in terms of how the user’s meetings
are going to be after they start using Meeting King? My meetings, unlike
the other bozos in my company who aren’t using it yet, my meetings, stuff
gets followed up on.

Edwin:  Yeah, my meetings are productive, on-target and things get

Jason:  Well, look, nobody sits around and goes man, I wish my meetings
were too productive. It’s true, you do wish the meetings were more
productive, but that’s just not what someone says.

Edwin:  I do get a lot of searches for that, by the way.

Jason:  When someone’s looking around, when they’re talking internally
and saying, “Hey, how can we make our meeting more productive?” They may
say that, but really again, I think there’s more evocative things.

So for example, again, I think creating steps is bad. That’s again
getting into how it might work, but I don’t want steps, at least not on the
homepage. You can imagine a how it works thing and you say okay, here’s how
it works. Pre-meeting is good because your agenda is set first and people
are prompted to come to the meeting having done certain things.

During the meeting . . . so when you talk about how it works or a
tour and that kind of stuff, then it makes sense to do that. But right on
the homepage, there’s different ways of course of doing this here. Another
idea would be to say matching up . . . the sort of pain solution match-up
process can work. You can get creative and not make it really boring, but
you can say things like, “Tired of people coming to meetings unprepared?”
And that’s the title.

Then the paragraph under there is like three or four sentences tops
that just says, “With MeetingKing, your agenda is set before the meeting
starts and is sent to all the participants. Furthermore, each one knows
with what they’re supposed to come. So now, when someone comes unprepared,
they have no excuse.”

Here’s another one, like “Tired of meeting minutes disappearing into thin
air?” You know what I mean? Something like that. Or, “Tired of going into a
meeting and forgetting what we talked about last meeting?” There’s these
key pain points like that. You can literally have question-answer in a
sense. And again, not features. Or maybe a couple features here and there,
like “it even integrates with Outlook.”

Features like that are good to make people feel like it’s going to work
with stuff that they have, that’s good, like you have there with Google
Calendar and Outlook Calendar for the agenda. That’s the kind of thing to
throw in that is good because you’re reassuring them this is going to be
easy. It’s going to work with the stuff you’ve got. But that sort of thing
would describe to someone if they can’t answer yes to those questions,
they’re not a customer.

Edwin:  I like that a lot.

Jason:  And if they do answer yes to the questions, there you go. They
found you. And then I’m not confused at all with the task management stuff
because it’s very clear this is all about meetings and the accountability
of what’s going on in the meetings which is different from project
management when you use words like that. I think those are good words.
Maybe that’s not the perfect word, but to me, to an organizer saying let’s
get some accountability here? It sounds like yeah, yeah, yeah, lack of
accountability is definitely a pain point for most meetings I would say.

Edwin:  Yeah. No, I completely agree. Also, the reason why my focus has
been on the meetings even though I have the functionality for the tasks,
etc., I have quite a few users that use it actually exclusively as their
task manager and some of them don’t even use the meeting part; they only
use the task management part.

Jason:  So what?

Edwin:  No, that’s great. But the challenge with task managers is there
are a gazillion out there, so how are you going to communicate it? How are
you going to position yourself?

Jason:  You don’t. See, you’re doing a kind of classic thing. I used to
do this a lot as well. You’ve put all this time and effort into tasks, and
so you want to talk about it. In other words, it’s like you want to talk
about equal weight about things depending on how much work it was to do it
or how unique it is. But neither of those things is necessarily right.

Again, I hate to beat on Asana as an example. I just happen to know a
lot about them and they’re being very, very successful. So just to beat the
dead horse, one interesting thing is what they want to do is replace email.
But they’re not going to say on the homepage replace email with this
because everyone would run away and say what? I’m not going to replace
email. It’s ridiculous, right?

Edwin:  Yeah.

Jason:  So the whole entire goal of the company is not on the homepage.
Imagine that. And you can’t believe the amount of thought and features and
things they put into trying to make that true, trying to make that a
reality, but they don’t talk about that ever because it’s not what anyone
wants to hear. It should happen. That will make them successful if it
happens, because internally they talk about it all the time, but that’s
different than what you say on the marketing page. The marketing page has
to be based on what that person is seeing, what they’re willing to accept
at this moment, what’s going to resonate with them and what’s going to make
them want to try it.

Now once they get in and see stuff and experience it and start exploring
and see that that’s totally different? But we’re talking about homepage.
We’re talking about positioning and we’re talking about marketing. That’s a
whole different thing. So even if 90% of your effort were in task
management, I would still say . . . and people discovered that that’s
actually huge and started running their business that way or whatever?

But your hook is meetings. That’s what’s interesting and unique about it,
until such time perhaps that that other task stuff is so insanely amazing
that in fact it can stand on its own. And then, hey, you change. That’s
cool. But right now, I’m sure there are really awesome things with the task
management but I’m equally sure you can’t make a homepage that’s so
compelling on the task management front that it’s going to defeat all these
really big names that have amazing stuff. Not yet; not from a marketing
perspective yet.

So again, none of this is me trying to say what you should do for product
development, in fact, or what you should write in code in fact. I’m not
saying that at all. I’m strictly saying on the marketing side, it’s this
meeting pain solution to me that’s unique, interesting, emotional, it’s a
pain, and so I think that’s where your focus has to be on the homepage.

Edwin:  Okay. I think that’s a very clear conclusion that you draw and
I can find myself in that. That is a challenge that I have been wrestling
with. Okay, what am I going to communicate? How can I communicate it very
quickly and easily and stand out? And standing out to a company that got
$10 million dollars in funding even before they started Asana is going to
be very hard if you bootstrap it with your savings.

Jason:  Exactly. That’s exactly my point is you’re up against either
startups with funding or just entrenched names that have just been around a
long time and have a ton of customers and brand value. If you’re going
against that, you’d better have something really interesting and different
and something-or-other, and you do. It’s the meetings. So it’s like stick
on that meeting. Follow your nose when it comes to the customers, but stick
to the meetings on the marketing side. That is what you have that they
don’t have.

Edwin:  Yeah, if I get people saying, “Hey, I’d rather cancel my
meeting than go to one without MeetingKing,” yeah, that speaks for it.

Jason:  Yeah. I want to go to this homepage and think me, as the
founder of WP Engine, I want to go in here and think, ‘Oh my God, we need
this,’ and then sign up. And right now, I’m looking at write an agenda. I
already write agendas. Minutes? I just take the minutes either in Evernote
or write in Asana and manage tasks that I put in Asana. Like right now it
doesn’t seem like we need it, but I bet you we do need it. I bet you we do.

Edwin:  I agree, but how can I convince you?

Jason:  But that’s what I mean. How can you convince . . . so I
describe some ways you can at least hook me so that I don’t get bogged down
into those things and think I’ll use Asana for that. You don’t want me
bogged down on that. You want me going “oh my God, I’ve got to try this
thing,” so that I can see in fact I do need it and I have a better mindset,
a mental model for this is what I’m supposed to be getting out of it. I’m
supposed to be not only making an agenda, but something that makes people
prepare and come to the meeting prepared. And if they’re not, I can see
that and give them that feedback right away and the tool helps me do that
perhaps so that we get better at meetings.

Help me get better at meetings. Help make all of us better at meetings. And
one final thing I’ll say on this, and maybe we can change topics, but one
final thing I’ll say is you made a very important point which is the
organizer pays, not everyone else. It’s the organizer who is getting the
most benefit, and the other people hopefully get benefit and eventually
maybe they sign in at some point and it’s better if they use it, blah,
blah, blah. But the key thing to getting a new user is to get an organizer
by himself to use it, to see that it’s great, then bring everyone in. It
seems like the key moment.

Edwin:  Right.

Jason:  And so you can use that on the homepage too. So here it says
it’s sort of helping your whole company have more productive meetings, but
maybe you should talk to that organizer personally instead. Your meetings
are a mess. People come to your meetings without preparing, and you don’t
know how to give them the right feedback to fix that. Let me help. Your
meetings run late. Why? Let us help. You know what I mean? Talk to that
organizer and get that guy to sign up. You know, again, you’re right, the
whole company benefits and so on. But maybe if you can hook that organizer,
that’s another thing I would add to the sort of pros and your mindset as
you do this homepage.

Edwin:  Okay, that’s very useful feedback. So I think I have something
else, something to do in the next couple of days here.

Jason:  Yeah. I think another thing you wanted to talk about was the
whole keep bootstrapping or raise money question.

Edwin:  Right. So I really believe that I’m onto something here. I get
a decent amount of traffic. My marketing site is hosted at WP Engines so …

Jason:  No wonder you get so much traffic.

Patrick:  And it’s fast.

Edwin:  Yes, it is. No, I’m a very happy customer actually. Because I’m
so successful, I have to pay these overage fees so I’m happy with that. But
anyway, so I get a decent amount of traffic. I get quite a good conversion
rate from people visiting the site to creating a trial.

Jason:  Wait, let’s just go to the top. Why would you want to raise
money? Most companies should not raise money. Most companies do not raise
money. You’re a bootstrapper with lots of experience. You clearly can
produce a product and so on. Why do you want to raise money? Why is this
even on the table?

Edwin:  Because I have so many ideas. And I really believe I can do, on
the sales part, so much more if I have additional people. And the thing is
I’ve been doing this alone. I think it was either in one of your blog posts
or one of your other interviews, but being alone, it’s getting hard at

Jason:  Okay, hold up. These are really important things. So first of
all, if you had more people, there’s more things you can do.

Edwin:  Yes.

Jason:  That’s true in engineering; it’s true in sales; it’s true in
marketing. I’m sure it’s true across the board. That is always true for all
startups until they get old, right? That is always true. So that by itself
is not a reason to raise money. If you raise money, you’ll have more
people, but the stakes are also higher, the requirements are higher, and
you still don’t have enough people.

So I get that, but raising money actually does not address that. And
then you said you don’t want to be alone. Well yeah, you could potentially
find a cofounder. With higher pricing and other things in that nature,
maybe annual pricing and so on, you could probably get enough money
together to start having an employee if a cofounder doesn’t sound good.

Raising money completely changes what the company is and what the outcomes
can be and what your job is. Lots of things change. So hiring more people
and being around more people and getting more things done is not actually
one of the reasons.

Let me ask you this: what is it that you want as the endgame of this
company? Do you want to make a billion dollar company? Do you want to make
a company in which you personally take home millions of dollars, but it
doesn’t really matter what other form that might take as long as that’s
happening? Do you want to keep it a tight group of people where you know
everyone’s name forever and it’s just a high-performing, awesome group of
people? Or do you want to have a thousand employees someday? What is your
goal with the whole company?

Again, regardless of how you get there. What do you want? What would be the
best end-state for you? Do you want to sell it someday?

Edwin:  Yes, but that’s not short-term. In seven years my daughter will
go to college and travel is my biggest hobby so it would be great if I can
cash out successfully in seven years. But before that, I would like to
build a profitable business, a business that can exist on its own.

Jason:  Okay. Why?

Edwin:  Well, because I think that’s the very essence of a successful
business, that you can make profit with it.

Jason:  So would you say literally building a profitable, growing
business is fulfilling because it’s sort of doing something good in the
world, what a business should be, and all that sort of stuff for you?

Edwin:  Well, I think it is the ultimate measure of you’re offering
value to people that they are willing to pay for it. Yes, I think I would
get a lot of satisfaction out of that, and I am already getting that.

Jason:  That’s true. Okay, and when you say you’d like to exit someday
in the next seven years, let’s say between now and seven years from now,
what kind of money are we talking about that you want to have from that
exit? If it’s half a million dollars, that’s not enough.

Edwin:  No, that doesn’t help.

Jason:  I’m guessing if it’s $500 million, it’s enough. So what’s the
minimum you want to get out of it to where you’re like bang, I got enough
money on it that I never have to worry about money again or whatever it is
that your goal is.

Edwin:  Right. I’m 47 now. I’ve had the fast cars. Money is . . .

Jason:  So how much? Five million? Ten million? Just give me a number.
What kind of exit do you need to be successful?

Edwin:  Okay, I always look more at value than at what can I get for
it? Is it good?

Jason:  I know, how much money? Is it ten million? A hundred million?
What is it? One million?

Edwin:  No, one million doesn’t get you very far. Ten million, I think
I can be very, very happy for the rest of my life.

Jason:  Okay. How about five?

Edwin:  I have to think about it. Look, this is kind of a funny
discussion because it might be that . . .

Jason:  It’s not funny. It’s exactly what we have to decide in order to
know whether these tactics are the right thing.

Edwin:  Jason, listen, if the company is generating a lot of profit and
there is a huge cash flow, then five million might be way too little.

Jason:  That’s not what I’m asking you. I’m asking you how much money
do you have to have in the bank account to walk away from it to where
you’re saying great? Of course if the company is making five million a year
in profit, you wouldn’t sell for that. No kidding. That’s not what I’m
asking. I’m trying to figure out what end stakes are good for you, and it
sounds like an exit between five and ten million would be a good minimum
where you’d say “yeah, if there’s something in that general zone, all else
being equal, I’d be happy. That’s it. I don’t have to make a 100 million to
be happy. I’d be happy with ten; I’d probably be happy with five.”

Edwin:  I don’t need a 200-foot yacht with a helicopter, no.

Jason:  Okay, so all the things you’ve said so far are telling me do
not raise money. So you said I value making a profitable company. That’s
important to me that it be profitable. That’s the point. That’s the measure
of success is that it’s a self-sustaining, profitable, growing company.

When you raise money, that isn’t the goal. That is explicitly not the
goal, and that won’t be the goal for those seven years that you’re talking
about wanting to run this for roughly. I know that’s rough, but still. It
won’t be the goal, and it won’t be the kind of company that you’re
building. So it’s interesting that the fact that that’s kind of against
your nature, which I totally understand by the way and agree with that
nature, but that isn’t what the goal will be. So that will be dissonance
for you.

The second thing is exit. There is no venture capitalist who wants an exit
in which you would only make five or ten million. And the trouble with that
is you would be happy with that exit, again, assuming it’s a fair exit of
course. But assuming it’s a fair exit, a venture capitalist, and I’m
explicitly not saying angel because we could talk about angel and they’re
sort of special so that might work out.

But a venture capital, if we’re talking about institutional money, venture
capital is not interested in any kind of outcome where that’s all the money
you make because it means they wouldn’t have made much money and they’re
not interested in that. They’re not signed up for that. And to be fair,
when you take their money, you’re not signed up for that either or you
shouldn’t be.

Edwin:  No, I do think, and I realize that very much, that if I were to
take venture capital, the whole game changes. You know that I ran WinZip
before. I first did it for the founder. After that, I did it for a private
equity firm then we became a part of a larger corporation. The game changes
very much. So if I were to raise capital, I understand that I have to run
the business differently.

Jason:  Yeah, but the point is this. You’re 47. You’re not going to get
a lot more cracks at building a big business that can exit for five or ten
million dollars, right?

Edwin:  Well, I hope I still have some years left, but no.

Jason:  I know, but you don’t have five more cracks because building a
business that is that valuable just takes time. That’s all.

Edwin:  Yeah.

Jason:  So anybody in their whole life doesn’t have ten cracks at it,
right? You only have so many cracks at it. So the idea of being able to
make money from now until some kind of exit if any, and the options with
it, what it can look at and what size, if you’re bootstrapped or angeled
and we’ll get to that, they’re vast. There are many ways for that to
succeed and there are many ways for you to make money along the way and so

With VC, that’s simply not true. If the company absolutely skyrockets
and does incredibly well, then typically you can take some money off the
table in subsequent rounds and stuff like that which may add up to what
you’re talking about, that kind of money. That’s okay. But now we’re into
such a slim chance. The most likely outcome is that you wouldn’t make money
at all.

On the other hand, it doesn’t take you much money to be literally never
wanting for money again. And so, again, to me, and again I don’t know you
personally so this is all just very superficial. But the things that you
want? “I only need a little bit of money to never have to work again. I
want a company that’s profitable.” And you strike me as someone who wants
control over the company and wouldn’t particularly like to become a GM
again. You’d rather stay a CEO this time is my impression. These things are
not commensurate with raising money, at least institutionally. So it feels
to me like that’s not there.

Now one other thing there is that also you don’t have the data right now
for that. What I mean by that is startups nowadays that raise money have
absolutely ludicrous metrics. It’s hard to imagine how they even got it. In
the consumer space, the saying is a million active users is table stakes.
You’re not even going to talk about raising money if you don’t have a
million users.

Now this is not a consumer company, but even in this, you have several
hundred users. They pay something like . . . I’m just looking at the
pricing page. The middle one says $40 a month, so let’s just say on average
they pay $40 a month. I don’t know what they pay. These are all numbers
that are really small that are not going to interest institutional VC. This
is not an interesting growth rate. It’s not an interesting amount of money
or an interesting number of companies.

Of course you’re going to change the homepage, but if I’m going off of
that, just for what the company is today, and I see schools, nonprofits,
etc., I’m instantly out because those companies are horrible for venture
capital. For venture capital, right? You just don’t have enough traction on
the business side to demonstrate that that’s there.

So in other words, the bottom line is you’re not prepared right now in
terms of the market, the product, the metrics anyway for VC, and it doesn’t
sound like you’d be happy with VC. So my initial thing on the VC angle is
not a fit for what you want and for what it is. Does that make sense? What
do you think about that?

Edwin:  It makes sense, and it’s also why I’ve been doing it this time
with being my own angel and self-funding it. And of course I’m very
fortunate that I can afford that. Sorry?

Jason:  That’s called bootstrapping, right.

Edwin:  So I’ve been very fortunate that I’m in that position. The only
reason why I bring this up is that gee, I really think that I’m onto
something. I think I might be able to speed things up, especially now that
everybody always talks about the book The Lean Startup. I really like the
book Nail It then Scale It. Why not get a partner?

Jason:  You’re not ready to scale yet. You’re not nearly in scale phase
yet. Well, I guess you don’t want to tell me how many people sign up a
month or do you?

Edwin:  I prefer not to, or at least not while we’re recording if you
don’t mind.

Jason:  Unless you’ve got all these hundreds of customers in one month,
you’re totally not ready to do anything with the word scale in it. That’s
not happening right now. You don’t have a product market fit; you’re not
able to describe who the customer really is; you’re not getting 10 or 20
people a day paying you. You’re just not having to deal . . . you’re not
having issues of scale to deal with and to go apply money to. That’s just
not what’s happening right now.

You’re still trying to find this is exactly what we are. This is why people
buy. This is who we’re selling to. We’re starting to see if we spend a
dollar, we make four like automatically. You’re still seeking all of these
engines of the business, which is fine. It’s just what phase you’re in. And
therefore, not ready to do anything with the word scale in it. And again,
that doesn’t have the metrics that a VC wants. And anyway, again, you don’t
need to.

Now angels are a different story because there are all kinds of angels and
typically angels don’t care about the nature of the exits, meaning because
an angel doesn’t have a fund with all the fund dynamics, they’re not
subject to that same portfolio theory. Now some people say that’s why
angels lose a bunch of money, but that’s their problem. The fact is that’s
how they act. The fact is typically angels are happy to just get their
money back. If that’s the exit, they’re fine, because oh good, I get to
play with the money again. That’s the attitude, right?

Edwin:  Yeah.

Jason:  Typically, angels are very, very happy if you have an exit that
makes you independently wealthy and gets them even just a small return.
Typically they’re thrilled because that’s kind of why they’re doing it.
Look, there are a few professional angels and again you won’t be able to
get any of those because you don’t have metrics to back it up.

So for example, some of the companies that I’ve been angel investing
in, they literally have hundreds of thousands of active users just going
into angel rounds because they’ve already bootstrapped stuff. They’ve got
some small seed stuff. And the number of companies available to have those
kinds of metrics are actually surprisingly large. And so professional
angels that have access to real deal flow? They don’t have to make bets on
companies that don’t have a lot of traction yet.

Now every company starts with not having much traction before it gets it,
right? That’s what they all look like so it’s like what the hell? But they
have the luxury, the ones that are sought after, the professional ones that
are sought after. They have the luxury of saying “right, but I see a lot of
deals and everyone wants me to be in their deal. And so I have the luxury
of sitting back and saying hey, I don’t have to take that bet because the
next company that comes along will be further along and I’ll take that
bet.” So people who are great and have good deal flow have the ability to
not have to take as much risk. And that’s unfortunate for folks who are
still trying to prove it out and still trying to build it up.

And so that leaves you with angels who are more like friends and family or
just not those professional ones, again, the ones I’m talking about where
look, this is fun money. They want to be a part of something. Maybe they’re
on Angel List, maybe not. Maybe it’s some local angel forum kind of thing,
there’s a lot of those.

Edwin:  Yep.

Jason:  Often they’re successful businesspeople and they’ve got a bunch
of money so they just set aside a couple million for this because it’s fun.
And again, they don’t have much expectation of return. Everyone wants to
make a return, of course. But at the end of the day, they just want you to
be successful and happy and maybe make a little return. It’s fine. Now they
typically won’t be terribly strategic to you in terms of helping with
recruiting or strategy or anything like that. Sometimes they are.

Edwin:  Or press coverage?

Jason:  Or press coverage, right. Probably not. But it’s just money. So
it just solves the thing you were saying where it’s like “look, just give
me some money and there’s four things I know I can go do that will help
because X, Y and Z will bring me . . . I know if I just do some more
marketing, this will happen; I know if I get press, that will happen. I
have evidence that if I make these features, I can go get these customers,”
or whatever. A list of stuff. So if it’s just getting money, as they say
dumb money, then angels could be a way to do that.

And that’s fine, but again, there’s also all these downsides. There’s all
this paperwork. You have to report to them. Some of them want to bother you
all the time. It’s hard to tell them to go away because you have their
money. So even then, it’s always better if you don’t, right?

Edwin:  No, like I said, that’s why I have been doing it so far on my
own dime. There’s a third alternative, and that’s a cofounder.

Jason:  Oh, yeah.

Edwin:  You briefly mentioned that already. I’ve had some exploratory
talks with people, but there’s a huge challenge of course and I think I’m
probably not the only one who struggles with that. “Gee, I’ve invested all
this time. I’ve invested all this money.”

Jason:  So?

Edwin:  You get a cofounder onboard. How do you split equity? How do
you split revenue? How do you do that?

Jason:  You work it out. No, it’s not 50/50. You just work it out
unless they’re coming with a whole lot of stuff behind them that really is
going to be worth a lot. But look, you just set up something where if it
doesn’t work out in the first year, they don’t get anything. So you know
you have a rip cord if you need one. You make sure all the prenup stuff is
good. Make sure you have a lawyer for that and so on. Make sure you can
undo it if you have to.

Edwin:  Yep.

Jason:  And yeah, look, of course it’s a risk. What if the person is
bad? What if they screw things up? In some ways, the worst thing they can
do is be mediocre because then you can’t point to something they screwed up
and say this is why you have to leave, but on the other hand, they’re not
killing it and they’re not really doing it. In fact, that’s kind of the
worst outcome.

Edwin:  Maybe it is, yes.

Jason:  But look, just because you’re cofounder doesn’t mean it’s 50/50
and you may or may not call it cofounder. You may call it employee number
one with a really low salary and really generous stock options and as the
company grows, you’ll fix their salary. Maybe that’s one way to go, right?
It doesn’t have to be that.

Reid Hoffman has some interesting stuff about cofounders. He says there’s a
lot of kinds of cofounders. There can be a cofounder that shows up four
years later, because cofounder in his kind of thought process, and I like
the way he thinks about it, it’s someone who acts like a cofounder. It’s
someone who works the 16 hours a day, 7 days a week like you do for real
and absolutely is poured in all the way and is making that kind of impact
that you can feel and see. It’s undeniable and it’s forever and their
identity is locked up in it.

These are the kinds of things that you can call them honorary cofounder or
something, but these are the qualities that are important. And of course,
it’s not 50/50 stock or any of that kind of stuff. Of course there’s a
prenup and of course you control the company and you decide and you should
be able to decide that person can’t be here anymore. Of course, that’s not
the attitude you have going into it, but legally that needs to be the case,
right? So you have that.

So yeah, of course it doesn’t mean 50/50. So I think that’s a great idea. I
think it’s interesting to think about what would that person be, exactly?
What is the hole you need? Is it more the marketing/sales side? Is it more
the engineering side for you to do those things? And maybe an interesting
way to attack that is to ask what would the perfect person there look like?

So for example, if you say look, marketing, sales, marketing, sales, the
product basically works. We just need more people to find out about it. If
more people find out about it and understand it, they buy it. That’s what’s
happening. I just need that to happen. Can you find someone where they have
a rolodex of some people they can call to get going on some of the bigger
things? Can you find a person who has some really good marketing experience
in an adjacent market? It’s not meetings, but maybe it is to-dos.

Could you pull . . . Asana’s too new, but is there a marketing guru at what
are some of those to-do software . . . like Remember the Milk. Is there a
marketing person at Remember the Milk you can hire and say look, what you
did is great. Everyone knows who you are. But instead of flogging this
thing that’s never going to add a feature ever again, how about become a
cofounder this time and really make a difference? You know what I mean?
That kind of an offer.

So again, what would that person look like? What will they have done? What
might their title be today that you could search LinkedIn on or you could
pummel your network around? And it all depends on what you need them for.
For all I know, it should be an ace developer so you can do those things. I
don’t know. It’s useful to think about what would that person bring to the
table other than working really hard that would give you an edge or maybe a

Edwin:  Just boost it?

Jason:  Yeah.

Edwin:  Yeah, okay. Well, the people that I’m talking to would actually
fit the skills that would be very welcome to increase visibility and just
give it a boost. It was a couple of years ago that I needed a technical
cofounder because I’m not a programmer myself, but I have now a very good
technical team that I’m really happy with so I’m all set with that.

Jason:  Nice.

Edwin:  So yeah, it’s good stuff to think about.

Jason:  Okay. And then the final thing is just getting the revenue up.

Edwin:  Yes.

Jason:  A lot of things are solved with revenue. Is there a repeatable
advertising channel that’s going to get you people? Can you try an annual
plan and see if people will do it? And if they don’t want to do it right
off the bat because maybe they can’t commit that much right off the bat, is
it something you can go back after a month or two and offer people? That’s
the kind of thing that generates a huge amount of cash flow immediately
which is exactly what you need to plow back in to do these kinds of things.

And some of that may be exactly to hire this other person to do
whatever, like acquisition, and fuel the growth that way. Or it could just
be as simple as look, there are some paid ads that actually work and maybe
you know some of those. And it’s just look, if you could just apply two
grand a month instead of $500 a month, that would already make a difference
and a few people switching to annual would just hand you the money.
Sometimes, there are simple things like that.

When the company is small like this, small changes in cash flow like that
can actually make a big difference in your ability to apply that to growth.
And you’re not going to 10x your growth in one month, obviously, so if you
can just get a boost and make next month twice as big in growth as it
would’ve been, and then do that again and do that again, that’s actually
pretty meaningful pretty quickly and you only have to move money around a
little bit in order to try to make those effects.

Edwin:  Yeah, yeah. Okay.

Jason:  The final thing is I just think the prices feel really small,
really low. I don’t know if that’s due to people having credit cards under
limits they have to reach at bigger businesses, and the fact that it does
say clubs, schools, etc. that have no money at all. But that is something I
would definitely consider changing. It will change the demographic of who
tries it and who can buy it, but your RPU is so low that there’s very
little you’re going to be able to do to acquire customers profitably.

Edwin:  Correct. I am actually planning on experimenting with pricing.
I mean both you and Patrick, Patrick McKenzie, there’s a lot of interesting
information and discussions out there on the value and the pricing of
software-as-a-service. So it’s definitely worth it to do experimenting with

Jason:  Charge more. That’s it.

Edwin:  That’s what it comes down to.

Jason:  No, seriously, forget all those metrics and ratios and crap.
You just have to charge more. Your RPU is too low.

Edwin:  What do you think about my business model where the organizer
needs to have a paid account and participants, they can provide comments
and they can contribute to the agenda. They can update tasks. They can do
so with a free account. Do you think that’s a good business model? Or do
you say . . .

Jason:  Yeah, I like it because only one person has to be convinced to
get going. I don’t like companies where you have to get a whole bunch of
seats just to start. That’s a barrier. You just want one person to have to
be able to make the choice and to cause it to happen. Now of course you
want people to login so that you can know about them and do stuff like
emailing them and say “hey, you’re a participant in that meeting. Did you
know you can use this to run your own meetings?” Right? And try to get them
to in fact become an organizer under that same company. So I love the idea
of just get in with minimum barrier, but then try to use that to grow the

But all that means is you just need to charge more per organizer. Again,
like this Pro Individual? $10 a month? I see there’s the checkmarks and all
that kind of stuff around what you can do, but the point is I don’t care
what you can do. It’s just so little money that you just never, never can
make money at $10 a month and you certainly can’t afford to pay for user
acquisition at $10 a month. And so to me, everything here needs to get a
lot more. And you’ll have to do better at explaining the . . .

Edwin:  The ROI?

Jason:  No, not the ROI, the value. ROI . . .

Edwin:  Well, isn’t that the same?

Jason:  No, it’s not, because ROI is when you say things like “if you
save ten minutes per meeting times this many meetings, you’ll save this
much money and time and the tool costs this, therefore it’s profitable.”
That’s an ROI argument, and nobody thinks that way. Nobody. Nobody actually
does this calculation, believes it, and no one’s budget works that way. No
one gets to pay for meeting stuff out of their budget because they saved
time and it comes out of some time budget. That isn’t how company budgets
work. That isn’t how people think.

Edwin:  Yeah, one of the challenges is that meeting cost is not a
separate line item on the P&L statement so nobody attacks it.

Jason:  That’s correct, but your tool is a line item somewhere on a
credit card bill. But in no place do you see on the P&L you saving money
somehow. We know, you and I know, of course it delivers all this extra
value above those dollars. We know that. But the P&L doesn’t know that,
right? That’s not going to show up. And that’s why the ROI argument is not

So rather, the person simply needs to believe it. In other words, you have
these testimonials on the front page that are really great. “I swear by it.
I’d rather cancel a meeting than go to it.” Okay, so a person that says I
refuse to do a meeting without it, a person who says that, it’s worth $10 a
month? That’s it? The feeling that they get by saying that, whatever that
feeling is, whatever that reason is, they think that not because of an ROI
or calculation, but because of something else like the alleviation of the
pain of meeting management of not tracking what people do or agenda writing
or whatever the thing was. It’s worth more than $10 a month to that person.
I know it just from what they said. So is it worth $100? I don’t know. But
not $10.

So definitely, you have a lot of tiers. You only have a couple hundred or a
number of hundreds of customers, so I can’t imagine you would necessarily
need all five tiers. On the large end, you might say call us, so you can
actually talk to someone and negotiate something much bigger; Twenty-five
organizers is actually kind of a lot.

Edwin:  Yeah. I actually have a few of those. One is a very large
school system.

Jason:  That’s my point, so how come it’s only $124 a month, right?
That’s a lot of organizers for a little over $100. That doesn’t make sense
to me. That should be much higher or probably have been negotiated
separately so you could kind of ask how much have you got?

So anyway, that’s just a long way of saying raise prices. The value
has to be higher than this. If people are really getting value out of it,
then they’re getting more value than this anyway. That’s the truth. And if
their budget doesn’t allow them to pay more than $10 a month, you can’t
have them as customers anyway. You can’t afford it.

Edwin:  Okay.

Jason:  You can’t afford it. If you can have 1,000 people immediately
today say, “I’ll give you $10 a month,” you still couldn’t afford that. It
sounds like oh, that’d be great until you do tech support for 1,000 people.
Then how did you acquire them? With what spend did you acquire them and
when do you get that back? It actually doesn’t work. And you’re
bootstrapping which means you have to have profit to pay yourself, and then
you have to have profit to use the business, to put back in the business.
You have to have extra money to do these things. And at $10 a month, you
will not have extra money to do things.

So to me, you just have to raise these prices then the people have to
believe it’s worth that. And things like the homepage change we made is
part of what will do that. It’s that feeling of yeah, this is what I’m
getting and this is why when the bookkeeper, the inside accountant, comes
over and says “hey, what’s this $79 a month charge again?” They’re like “oh
man, I use that like ten times a week for all my meetings. We have to have
that.” And they go “oh, okay, whatever.” Right? That’s what you need. That
little moment is what you need. And since they’re spending the company’s
money, the only question is budget and their willingness to tell an
internal accountant about it. And in that case, anything under $100 is
probably something they can do if they’re getting value out of it.

And again, maybe $79 is too much for the low plan. I get that. But if the
low plan was more like the $40 that your small is and maybe the next one is
$99 and that pro large is more like $500? Let’s get this stuff up there so
you can get some extra cash.

And then finally on that, consider after you do that and after you sort of
settle on what your new prices are that are working, consider going back to
your existing customer base and asking them to pay more. That’s a whole
other discussion really, but . . .

Edwin:  Yeah, I was going to say, I don’t like that. People who have
supported me from the beginning, I think . . .

Jason:  That depends. It depends on who you ask. And maybe some people
you don’t ask because it’s not appropriate or you don’t want to, but there
are people where if you described it like a human being, they would be
happy to pay more. There are people where you’d say look, obviously, this
is a small business I’m trying to run here and I’m trying to make this
product better for you and have good support.

Edwin:  Yeah, and continue to invest in development.

Jason:  Well, yeah, but that’s for you. You can say “Look, what I
realized is at the prices I have now, I can’t afford to do it. They’re too
low. And you at the big company paying $40 a month for 5 organizers? You
probably know that $40 a month is not really enough to sustain me as a
business. This is one of the things that I’ve figured out.

So I’ve got new pricing, and this I do believe will be enough. I’m
going to hire another engineer. I’m going to hire a tech support person to
make sure that if you have any questions, you get them answered. I’ve got a
list of stuff that you, the customers, have asked for that I’m going to
do.” In other words, you can really make the case and I think a lot more
people than you’d think, if you make a personal plea that it’s not about
the company but you and building your company, they’d actually react quite
well to that.

And even if a few people cancel, if a lot of people do it you make a lot
more money anyway. And again, you want customers who are in this with you
who do understand that. These are good customers. These are happy customers
and happy for you. This is a good relationship. And someone who says “No,
it has to be $10 a month. I’m out of here.”

Again, that’s not really a great customer relationship anyway. It’s not
clear they were getting a lot of value anyway. They certainly don’t
appreciate what it’s like for you as a small business owner anyway, so they
may be let down by other things like you not having 24/7 support the one
time that they needed it. They’ll probably be disappointed then too, right?

Edwin:  Right.

Jason:  It’s not necessarily a bad thing. And again, you’ll hold out
people you know. There are people you know you’re not going to ask them or
something. Fine, right? But a lot of those hundreds of people might be more
willing than you think, and that kind of a cash boost immediately is pretty
darn significant right there. Again, it’s such a big change to the company
for you to do it because it all goes to the bottom line, obviously. You
really should consider doing it.

And one last thing on that, one last little trick, you can make this
impassioned plea and then say this. “Now I appreciate that you’ve been with
me since the beginning, and I wouldn’t want someone raising prices on me
even if it was kind of needed for the company. So here’d what I’d like to
do. I’d like to offer you right now you can stay at your current rate
forever, and I’m not going to bother you about it and it’s perfectly fine,
or you can join me at the new prices and join me in making this company
successful. Either way is perfectly fine.” Leave it at that and see what
people do.

And that way if people really, really . . . if they write back and say
“Look, dude, I love you but I really don’t have the money,” you can say
“okay, that’s cool, I understand that.” And everything’s still fine, right?
But the customer also knows that they’re sort of paying under, and that
might be good for support later on.

So that’s okay, but then the people are like “Yeah, dude, I’m with you.
Let’s do it.” Those people are now opting in. So again, that’s just a very
long way of saying I think there’s ways of doing that that are very
friendly, very human, perfectly fine and perfectly ethical and can change
your cash flow by thousands of dollars a month.

Edwin:  Okay, definitely something worth trying. Like I said, I am
planning on experimenting with my pricing and that could be then the second

Jason:  Yeah, experiment first then when you lock it in you go back to
your audience. The only other thing is if you’re experimenting on the web,
you may need to tell your customer base or at least be aware because if
some of them go back to the site and see different pricing, they may be
surprised and then worried, “Wait, does this affect me,” and so on. So
maybe say nothing. Maybe tell them something. But just be aware of that
potential problem.

Edwin:  Well, a possible solution would be that I announce it a month
before that now the price is $9.95 and next month it will be $19.95 or so.

Jason:  No, that’s not enough.

Edwin:  That’s not enough?

Jason:  No. Charge more. Not $19.95. More.

Edwin:  I don’t know. It’s interesting because I had a discussion about
pricing with a very successful friend of mine in the software business and
he said “Oh, you’re way too expensive.”

Jason:  That’s fine. Not everyone can be Neko Mech [SP].

Edwin:  I’m not mentioning names.

Jason:  This is not that kind of product that you literally sell a
million of.

Edwin:  Right, it is not and I do think in a lot of cases it does offer
a lot of value, both monetary by saving time, but also the fact that you
just get things done and that is even much more important. You start with
the completed tasks from the previous meeting, so you start off on a good
note. “Hey, look what we accomplished.” Yeah, I think that is important.
You have a positive setting when you start.

Jason:  Sure, yeah. That is the right argument, not the ROI argument.
So look, if you want to lower prices, do it, but I think if you dropped all
your prices by half you would not multiply your actual paid users by say 4x
that would overall make you 2x more money. I don’t think that would happen.
But I do know you’d have two more tech support and you would not extract
much money out of big customers.

Whereas if you go the other direction, you’re likely to have much
more profit per customer and still have pretty much the same number of
customers. That’s generally what people find, by the way, when they raise
prices dramatically is the sign-up rate doesn’t change at all which is the
most common result. And I say most common because I’ve talked to a lot of
startups about this. I can start listing them. I probably shouldn’t just
for their own sake, but time after time.

And by raising prices by things like 10x, and that doesn’t mean you should
necessarily raise it by 10x. I’m just saying typically you raise prices.
When they’re this low, I would say the $9.95 is really too low. Maybe $39
is a better place to start. Maybe $29 if you really don’t have the stomach
for it. And then get up to $99 quick or $129. Get up above there really
fast and then have that high upper tier. Typically, you see no change in
signup rate.

Edwin:  Now one more crazy idea that I have. I think GitHub had it,
maybe they still have it. So I’ve had these long conversations with the
insurance company, and in the end they decided it was too immature or I’m
too small of a company so they didn’t want to move forward.

Jason:  Right, okay.

Edwin:  So big companies are interested in it. What if I offer an
inside firewall solution that they can install on a local server?

Jason:  No, don’t do that. I don’t think you have evidence they want
it. You don’t have 20 companies who are using it and saying, “This is
great, but I really need it inside the firewall,” and giving you thousands
and thousands of dollars a month. You don’t have that proof. Just because
people contact you doesn’t mean that that’s interesting.

Edwin:  No, but if you just put it up on the pricing page? “Hey, we
have this inside firewall solution. It’s $25,000 per year plus X per user.”

Jason:  If I were you, I wouldn’t want to sell those. Have you done
that before where you’ve supported hosted things behind the firewall?

Edwin:  No, but I’ve had lengthy discussions with the main developer
about that.

Jason:  Right, but it’s hell to do that. It’s ridiculous. If I were
you, at that price, I wouldn’t do it.

Patrick:  You get into this whole version thing that’s . . .

Edwin:  No, I’m aware of the challenges, but if the money is good
enough . . .

Jason:  That money is not good enough. That’s pretty shitty money for

Edwin:  All right.

Jason:  You said 25 a year, not a month, right?

Edwin:  Yeah, $25,000 a year plus let’s say $50 or $100 per user. $50
per user or so.

Jason:  Again, it wouldn’t be worth the time to me to accept that
incredible additional complexity of now you don’t have just your one
[server] that you control and maintain and have data from that you can do
whatever you want to at any time. Now all of a sudden you have a
proliferation of other things that are behind firewalls that you don’t
control if and when they upgrade. You don’t really know what’s going on
there. You have to manage these images and deal with whatever that is.
There’s going to be authentication systems because you’re going to have to
integrate with LDAP or Active Directory because that’s another thing these
companies want. It’s just this whole ream of stuff that just starts coming
in. I don’t know why you’d want to do that rather than focus on the company
that’s working.

Edwin:  Okay.

Patrick:  It also changes the tone of where you have it now, you have
users who are excited to use the product and you can grow out a tribe
inside an organization. If you’re selling all at once, it’s going to be
used by fiat. Then people say, “Well, we have this system. You’re required
to use it.” It changes the whole tone of the way you communicate your
entire product to users I think.

Edwin:  Okay. Yeah, I mean the bottom-up approach of course is really
nice if you get a couple strong evangelists.

Patrick:  It’s certainly different. I tend to prefer the more evangelist
approach as well. But at a minimum, they’re very, very different.

Edwin:  Yeah.

Jason:  Look, the bottom line is the last thing you need is to add
complexity to anything you’re doing because there’s only you and a small
team of developers and hopefully one or two other people soon, but that’s
all. Anything that adds complexity and complication or multiple things or
anything and cost? Man, I would just run away from that. Run away.

Edwin:  That has always also been one of the things at WinZip. We kept
it simple, the business model. But fortunately there we were in a position
that we could occasionally say, “Nope, sorry, we don’t do that.”

Jason:  Look, every hour that the team spends trying to do this thing
that’s going to be a constant nightmare to do, every hour you spend in
there could’ve been spent on something that makes it more valuable in the
first place. It could’ve been spent on a feature that makes somebody want
to buy it. Every second you spend dealing with selling that, you could’ve
been getting PR that gets a hundred signups that are cheap to support and
deal with. Every time someone deals with a tech support call from an old
version of something or other and you don’t remember whether some option
was there or not? It’s an unbelievable burden to have when you could be
spending that on things you know are much more likely to be valuable to

Edwin:  Okay, makes sense. Makes sense, those arguments. Yeah.

Patrick:  Gentlemen, this was fun.

Edwin:  I really appreciate your time and sharing your insights. I
thought it was a very good conversation, and I enjoyed it.

Jason:  Thanks, I had fun too. I want to see the new homepage because
we still need help with our meetings I think.

Edwin:  Yeah. Well, there’s nothing to stop you from starting to use it

Jason:  Yeah, right.

Patrick:  You’ve got to thrill him first.

Edwin:  Okay. Well, thanks again, and I look forward to having a link
on my website to your blog.

Jason:  Okay.

Patrick:  Thanks, guys.

Edwin:  Thank you. Bye-bye.

Jason:  Bye.

13 responses to “Smart Bear Live 8: Edwin from”

  1. I learned a lot from this interview and I appreciate the time, effort, and thoughts that went into it, all around. I don’t have the numbers, but it seems that Jason’s word count is perhaps 10-20 times that of Edwin’s and I would have loved to hear more about his thought process, especially since aspects of it are under review in the discussion.

  2. @edwinsiebesma, drop us a line when you make the changes that were discussed in this interview, I’m interested to see your new homepage and to hear about how it goes when you raise your prices. Good luck!

  3. I was really affected by this podcast, now I want to go back and listen to the others. Was it fate? Because it hit at the exact moment for me. It was almost as if you were saying everything I needed to hear, but the constructive criticism was pointed at someone else, so I didn’t need to be defensive and I could actually absorb it.

    Earlier last last my wife brought up the opinion that I wasn’t charging enough money, and I reacted with anger saying “you don’t understand…” and stormed out the door to go do some side consulting work. while doing boring server maintenance work I saw your email about this podcast and started listening. It was true, what my wife said was true! Jason & Patrick put it into a bit more precise words but the concept remains the same.

    I could hear myself in many of Edwin’s responses too. I mostly heard FEAR. But I have it too, and probably so do many other founders too.

    Like I said, I am going to listen to the backcasts soon, and I think what I will be searching for is some way to understand the motivation of a founder. This seems to me to be the “unspoken” missing link, like not many talk about it (it’s assumed to be a natural part of a founder), but you need to understand what it is, how it affects you, and how it shapes your view of your business idea.

    I’m talking about the question “what do you want to get out of this business, in terms of a dollar amount / cash out”, etc… So I don’t know if you have a specific episode about that, but I’ll be searching and reading some older blog posts too, in an attempt to learn more about it.

    I figure that if I can correlate how much I want to make, then I won’t be so “scared” to try raising prices and being able to have a “relaxed natural conversation” about the need for the startup to survive so we can deliver the service that you want… and I may be able to finally stop the imaginary scene where I announce I am raising prices and the customer turns into a dragon and kills me with fire breath.

    • Thanks for the honesty and vulnerability. I promise that means a lot to many other people who feel the same way but don’t want to admit it on the Internet.

      The thing about figuring out what’s important to you, and what your goals are, is that it’s difficult, and individual. “To know thyself is the hardest thing,” said the ancient Greeks.

      This might help figure out what’s important to you in terms of messaging:

      This might help in seeing my thought process about selling Smart Bear: Or even that after all that, maybe it’s still not fulfilling:

      But ultimately it’s hard to do in a one-way blog post when it’s so very specific to *you*. If you’re willing to do a podcast like this one, maybe that would be a cathartic, useful way to get some ideas? (I never feel like I can tell you want to do, but certainly I can help you ask the right questions of yourself, and think of options that you might not have otherwise considered.)

      Finally, on price, it’s interesting because changing price also changes the type of customer and thus type of business. Really everything hinges on it. Here’s some thoughts on that with links to more detailed case studies where other entrepreneurs chose one path or another:

      That might be something I can write more about in the one-to-many blogging format.

      Thanks again for the note!

      • wow, thanks so much for the feedback & links. i will read & comment more Thursday night, (dead tired now). but your message is affecting me as this could be the reason i’m not getting anywhere, cuz i don’t know exactly where i’m supposed to be going.

      • Aha, I see what you did there… each article you link to has links to more articles, and soon I have 20 tabs opened! and after reading each one, I have a storm of synapses firing and I must type up notes, capture these thoughts & feelings flying through my brain. So this is gonna take a while to get back to.

        The initial thought I’m having is that I have previously associated inputs with inappropriate conclusions, ie. it’s all in the attitude. Especially when most of those inputs have come from the hype-induced media we read, the insane Instagram and SnapChat buyouts. Why wouldn’t we feel like losers if we read that and naturally compare our performance to those anomalies, concluding that “I must not be smart enough”.

        So these articles are really refreshing, as they appear to be coming from a trustworthy source whom seems like the concepts make sense (you can tell I’m still not trusting anyone just yet). It is so much more worthy to read a warning that you will have sleepless nights worrying about the jerks you’ll need to collect from to make payroll, so much better than “everything is rainbows and unicorns with this app I made in my local coffee shop in 1 weekend!”

        I guess it’s my hacker nature that makes me want to deconstruct the interpretations / attitudes behind what I’m thinking and feeling, with the (misplaced?) belief that I can hack my way to success if I can figure out how to have more good days and less “black pit of death nothing is working” days. And yet I already feel like I know there will be no easier way, I’ll just need to be agile enough to respond to whatever comes up. But I’m thinking it will be a bit easier to succeed if I have a good set of tools in the mental toolbox.

    • Thanks so much! The biggest limiting factor is the production — coordinating guests, recording, prepping the post, etc.. So hopefully I can find more help there.

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