What's up, everybody?
This is Cortland from IndieHackers.com, and you're listening to the IndieHackers podcast.
On this show, I talk to the founders of profitable internet businesses, and I try to get a sense
of what it's like to be in their shoes.
How did they get to where they are today?
How did they make decisions, both of their companies and in their personal lives?
And what exactly makes their businesses tick?
And the goal here, as always, is so that the rest of us can learn from their examples and
go on to build our own profitable internet businesses.
Today, I'm talking to Aleem Mawani, the founder of a company called Streak.
Aleem and I both started companies around the same time, in 2011 for me and 2012 for
him.
We were both funded by Y Combinator, and both of us built Chrome extensions that modify
your Gmail inbox and attempt to make you more productive.
The difference between our two companies is that his still exists.
I gave up, quit, moved on to other things, whereas Aleem and his co-founder kept plugging
away.
Today, his company is very profitable, generates millions in revenue, employs a few dozen people,
and he's just happy running it.
So in this episode, we get to hear Aleem's story and how he got here.
It's cool talking to you because we've both done things in the email space.
I did Y Combinator back in 2011 with this app Task Force, and Paul Graham had this huge
kick about how everybody's going to work from their inbox.
Everybody already is working from their inbox, and if you could just build something interesting
on top of the inbox, that's your Trojan horse to get hundreds of millions of users.
And it didn't really work out that way for me.
You ended up pivoting away from Task Force and working on other things.
But I think you started Streak, when in 2012?
Early to 2012.
Yeah.
We were in YC 2011.
We should talk about it later, but we pivoted through YC in 2012 is when we actually got
serious about Streak.
It's been eight years now.
How well is Streak doing in terms of revenue, users, company size, wherever you measure
your success?
Yeah, revenue is obviously a big part of it.
I think the part that we're most proud of is profitable.
Being a profitable Silicon Valley startup, it shouldn't be abnormal, but it is.
And so we're happy that we are self-sustaining and basically control our destiny.
So yeah, profitable.
We have 30 folks on the team.
We were in two offices before, and now we're remote, like most people.
And yeah, revenue in the millions.
Super exciting and not particularly common for companies, I think, that were started
back then to try to be profitable.
So I remember doing YC and building an email product.
And the partners there saying, why are you charging money?
Because we were part of the Stripe beta in 2011, and it was like anathema back then to
try to charge money for what you were doing.
You needed to grow as big as you possibly could, get millions of users, and then figure
it out later like all the rest of the Silicon Valley startups are doing.
Right.
We tried that as well, actually.
It wasn't that we were profitable from day one.
We didn't charge from day one either.
But at some point, we were like, for us, we're a CRM product built into Gmail.
And so for us, we weren't too worried about people paying us because they're used to paying
for CRMs.
They're used to paying for expensive Salesforce or whatever.
And so we weren't too worried about like, hey, could we eventually charge for this product?
We knew we could.
And we just honestly, we were lazy at the beginning.
We just didn't want to do the billing system.
We didn't want to do promos and A-B testing pricing pages and stuff.
We just wanted to hone and perfect the product.
And there was really probably no pressure back then to start charging anyway.
So yeah, I mean, like we had raised money, we've done the YC things, we got some money
there.
We'd raised seed rounds, we had some money there.
We weren't really hiring that many people, we had three or four people on the team.
So there wasn't a lot of pressure for us to start charging right away.
So if you could go back to 2012 and tell the brand new founder, Aleem, hey, this is where
we are in 2020.
Here's what we're up to.
There's so much money we're making, here's how big the company is.
What do you think you would say?
It's interesting.
I would be happy that we didn't die.
I used to think of startups as very, very bimodal.
And that is kind of in the conventional wisdom that you either get massive, Google massive,
or you die.
Those are the two options.
And I think the thing that would have surprised me back then was that, hey, there is this
third option of being a large growing business that is profitable and making money, but not
necessarily Google size.
And that's a great place to be.
Yeah, I agree.
You get a lot of control over basically what you do with your life, what you build at your
company, you're generating revenue, you're profitable, you got 30 people.
That's enough people.
You can just do pretty much anything you want.
You can say, okay, we're going to build this cool feature and just go do it.
You can take probably weeks off and just be fine.
And it's not necessarily, I think, what investors, at least in high growth startups, have traditionally
said they want it.
They want you to go for the boom or the bust.
How do you deal with those expectations because you said you raised money, do your investors
care that you want to take this third option?
Right, right.
I mean, maybe it's more than three options because either you die or you get Google huge
in nine months.
And then the middle option, a lot of investors would claim that's kind of a lifestyle business.
But I don't look at Streak as a lifestyle business.
I look at it as like, hey, I'm still putting in a lot of work and a lot of effort.
But it's because I want to and I really enjoy what I'm doing.
So it's not a lifestyle business in the sense of like, hey, I work four hours a week and
that's it.
It's not that at all.
Maybe that's like a fourth option.
But there is this option of still working hard on a business that you really enjoy,
it becoming very large.
There are examples of companies like Basecamp is a good example.
I don't think they've published their revenue numbers.
But from what I know, they're an extremely profitable company in terms of revenue, very
large.
And you can be a large growing company without necessarily the whole VC route.
Yeah, I think that's great for us because like we just, yeah, like you said, we don't
have the pressure to do things we don't want.
We have the time to focus on making sure that the inside of the company is solid, but people
enjoy their work, that we communicate well, we enjoy the people we work with, we work
on things that we enjoy.
And we have more time to breathe and do those things as opposed to like, I think when you're
under this constant pressure on the VC track, like you kind of put those concerns aside
and you're like, Oh, I'll deal with those later.
And I think the term lifestyle business being this sort of derogatory phrase to describe
people who don't want to work is so silly, because number one, who doesn't want a good
lifestyle?
If you look at the founders of a huge company, like you know what they're doing, like spend
a lot of time making sure their life is great.
And number two, if there isn't just one lifestyle, like not everybody wants to just like work
four hours a week and then sit on a beach, like a lot of people really enjoy the companies
that they build, they really enjoy the unique lifestyle that your company can provide for
you.
I think it's a lot more control over it, quite frankly, if you run your own company than
if you work for somebody else.
So I've never really understood like why that's been such a derogatory term.
Yeah, I don't think it's I don't look at it as derogatory.
And you're right, like you have to spend time designing, designing your life, I think maybe
the difference is with the VC back companies, you can say, hey, this is going boom or bust
in 18 months.
And so for 18 months, I can do, I'll put up with anything, you know, I don't care about
my lifestyle being great or not, I'll put up with anything and just get it done.
And then after that, everything will be fine, right?
And so that's great if it works out like that, because, you know, there is a finite time
and there's nothing, it's kind of like these two camps where, you know, the lifestyle people
are saying, hey, this VC track people are doing the wrong thing, the VC track people
are looking at the lifestyle people and they're saying like, hey, you're doing the wrong thing.
I think like both are fine, as long as you know which one you're doing and why you're
doing it.
So if you're on that 18 month thing and you're like, hey, I want to know, I want to have
an answer in 18 months, whether this is huge or not, great, do the VC track thing and like
go for it.
If instead you want to design your life starting from now, you do it a little bit differently.
Actually, sort of an open question for me that I've been struggling with is actually
we started in that path.
We started in the whole like, hey, we want to do the 18 month thing or whatever.
And that's obviously changed sort of since then, but I think we got really lucky.
We got the opportunity to raise some money, so we didn't feel the pressure at the beginning.
We had a chance of going big in 18 months, not that we're not going to go big in a longer
time horizon, but we had a chance to go big and that didn't happen.
The alternative wasn't zero for us.
The alternative instead what happened was we failed according to the VC model, but the
alternative was we created this large profitable business instead, like that was the failure
mode was large profitable business and large profitable and growing software business.
And so I think that's an option for, I think it's with SaaS, it opens that option as there
basically needs to be a new model for, hey, yes, you can raise money and attempt to go
to the billion outcome in 18 months, but if it doesn't work out, here's this other option.
Right now, there isn't a clean way to make that transition.
We kind of got lucky making that transition, but there isn't a clean way with, for example,
with investors of how do you make that transition.
There's no convertible note that says, hey, if you end up becoming a large profitable
business instead, here's what happens to the note, right?
All the financing docs and stuff like that are built around, if you go huge, here's what
happens.
And if you die, here's what happens.
Nobody talks about what happens.
There is no in between.
Yeah, nobody talks about that.
I think that's an option.
I think a lot more founders would start companies if they knew that they could still go big.
And if not, they could still be a large profitable company.
You're right.
There's something appealing about that 18 month vision of like, okay, I'm just going
to work super hard.
I'm going to crush it.
I'm going to sacrifice like these two years of my life and then I'm going to be set for
the rest of my life.
And it works out for some people, you know, like we both met people who that like that
happened for sure.
But I tried that also in my 20s and you know, a lot of people say they don't have any regrets.
I regret trying it.
I 100% if I could go back in time and do it differently, I would have worked more reasonable
hours.
Well, I think there's this idea that you can will like a billion dollar company into existence
just by working super hard.
But often I think like if you hit on something or like the market's right and your product's
right, like it's kind of dragging that work out of you.
Like you're just running, trying to keep up, but we're trying to push something that's
not really blowing up that way.
Then it's like, you really should get the same amount of work done in half the time
and have probably this similar outcome.
So it's not worth it.
Like, what are you sacrificing your life for this thing that's not going to blow up.
So I think the dream makes a lot of sense.
But ultimately, it's important to know when to call it quits and know when like you're
not on that kind of unicorn, crazy, common growth path.
Yeah, it's probably useful to like timebox it where it's like, hey, this is something
I want to do in my life is try to go down this PC path and make the next Google or whatever.
And there's a huge amount of risk associated with it.
And so therefore, I'm willing to commit this number of years in my 20s is reasonable to
invest in that.
It's not reasonable to invest all of them.
It's not maybe reasonable and have no outcome.
But yeah, as long as you sort of timebox it.
And that's kind of what I mean with the investment thing too, right?
Like right now, if you try to raise money from an investor right now and said, hey,
my plan is to become a billion dollar company.
But in 18 months, if that doesn't work out, I'm just gonna become a large profitable business.
If you said that in any pitch meeting, you would not get funded.
But it is, I think, a really useful heuristic for founders is to like, hey, I'm gonna invest
this amount of effort, this amount of time in doing this high risk activity.
And when that high risk activity doesn't work, if it works, great, I'll keep going.
And if it doesn't work, then here's what I'm gonna do next.
That's a really useful heuristic for founders.
But right now, it's too taboo to say that, right?
You couldn't say that in an investor meeting.
So I want to go back in time to like the beginning of streak and find out what you were thinking
back then.
Because now you've got like all these very wise and takes where you've been through the
trenches and possibilities at the beginning.
If you're anything like I was, like you had no idea what you're doing.
And it was a huge black box mystery in terms of what could happen.
How did you first come to start working on streak?
How did you come up with the idea?
I was in grad school and knew I wanted to do a startup.
I'd been like sort of Google before then.
And I actually left Google because I was like, hey, like, I'm kind of jaded on software.
It's not not for me.
So I went to grad school to get into like more physical businesses.
Like I wanted to learn about transportation, I want to learn about manufacturing.
But while I grad school, like, you know, I was doing all that work, but in my spare time,
I was like programming for fun.
Like, that's just what I was doing for fun.
And, you know, eventually I kind of realized like, hey, if I'm doing this for fun, that's
probably what I enjoy and what I should be doing.
But maybe just the environment at Google was not sort of for me.
And so I knew I wanted to start a company.
And so started working on, you know, like a made up idea.
It's like, hey, I want to do a startup, like, what would be a great idea for a company?
And, you know, just sat in my room by myself thinking of startup ideas or whatever.
And like, I think you kind of can predict where this story is going.
You know, it was basically like, you know, some loyalty program with your credit card
or whatever, you know, something that people don't really care about.
And actually, I had a great line from Paul Buca and PG about that.
But yeah, so was doing that, ended up going to white Combinator for that idea, worked
on it for the entire batch.
And then basically, they like the idea.
Well, they they like I think they liked us because what I did was with that idea, I went
out to and our customers would have been like local businesses.
And so I went out to a bunch of local businesses and I was like, hey, if I built this, like,
would you use it?
Would you pay?
Would you pay for it?
And I'm happy we did that.
And they all said yes.
So that was interesting, but they all said yes.
And I said, Well, I don't know if I trust you sign this piece of paper that says, if
you built this, I would pay for it.
And by the way, you know, it's non binding at all.
So it's of course, everyone signed it.
And so like, that kind of made me feel like we were onto something and our business was
sort of two sided marketplace.
So like, you know, we had these local business on one side, we had consumers on the other.
And so I didn't even bother testing the consumer side, I just like went to the local businesses.
And so they like the YC liked us because we're, you know, we came into the interview and we're
like, hey, we got like 20 letters signed from we haven't built anything, but we have 20
letters signed.
You've been pounding the pavement, you've been doing sales, you're like the prototypical
like these founders are hungry, we'll invest in them no matter what they're working on.
Exactly, exactly.
You know, we do the office hours with PG and, and he would always push back on the idea
of being like, Hey, is this really useful?
Does anybody really want this?
And we're like, No, no, no, like, you know, we were trying to be the prototypical founder
of like, no, you got to really believe in your idea, you got to like, push back on anybody
thinks that it's gonna fail or anything.
And so like, we're like, No, no, it's gonna work.
And then, you know, two weeks before demo day, you know, we go to the PG and we're basically
like, Hey, like, you know, our metrics aren't good.
Like, how do we how do we do demo day and show this to investors when our metrics aren't
that great?
And he's basically like, forget demo day, I'm just trying to understand how long it's
going to take you guys to realize that this is a bad idea, and you should not be working
on this.
And so I'm so grateful he was so direct, because like, and he was right, like, there's no there's
no use in like, you know, putting lipstick on the pig for demo day, right?
And so we pivoted two weeks before demo day.
And then he had, he had basically great, you know, PJ had great advice for how to pick
sort of next next idea.
And the main thing was like, Hey, what would yourself what would you yourself have used
in these last two months that you've been working on your business, like, what would
you have used?
And initially, our ideas were all like related to the thing that we're pivoting away from.
And he's like, Hey, your old crappy idea is done.
Don't try to like salvage anything from that, right?
Like, don't try to repurpose something you built for this new thing.
No, just like get rid of it.
It's gone.
You're starting from scratch.
Let's zoom in on this, this, this like solving your own problems thing where you're trying
to get an idea because I love the approach that you took off and I tell people the best
way to come up with an idea is to start a company that does anything, literally anything.
And when you're working on that, you're going to realize there's all these tools that you
would pay for that you would use that you need that are missing and then go like start
one of those companies.
There was probably like 10 or 15 things we built internally that have now gone on to
become like hundred million dollar businesses or more.
And it's because like we needed them.
And so we kind of built them.
And it had we not been working on like headstreak not been going well, we would have definitely
picked on one of those ideas and made that our company, you know, so definitely agree
with that advice.
Like just work on something and you'll find the something to work on.
How did you choose street over these other ideas that had promised and that could have
been big companies?
Like why was that the one that stood out to you as promising?
Yeah, so for us, man, we're just so lucky, I think, but I know that's not useful advice
to say we were lucky.
But I think it is important to recognize some of these, some events that happened.
But so for us, like, you know, we were selling to these local businesses and we were pounding
the pavement, like we would literally walk down like streets in San Francisco and like
knock on every local businesses door and just be like, Hey, we want to sell you this thing.
Hey, we want to sell you this thing.
And like it was me, my co founder, and we come back to our office slash apartment at
the end of the day.
And it'd be like, okay, like, how did your deals go?
How did my deals go?
And eventually we're like, Hey, this is kind of like what a CRM is for, right?
Like we had vaguely heard these, you know, this term CRM.
And so we tried Salesforce and it was like, awful for like two people trying to like run
a small business, like Salesforce is not the product for you.
And so we were just shocked that that was kind of a state of the art.
And like everyone used it.
And so instead, we just did a shared Google spreadsheet.
And we really liked it because we got to define the schema, like you get to define what each
row means, you get to define what each column means, it's like you define the products that
you want to build.
But the only problem is we, you know, after we found the pavement, we would, you know,
email these small businesses, and we'd be doing all our sales over email, and then we're
like copying shit back and forth between email and spreadsheets, and it gets out of sync,
and then you don't trust the spreadsheet anymore.
And then each of us just relied on our inbox.
And so it was a complete mess.
So basically, the idea came from that.
But the part that we got lucky with was when we shared that idea with PG, it was, you know,
we basically said, Hey, we think there's something here for the sales use case, but like integrated
into email, we think there's something there.
And he's like, Oh, let me show you this other email that I sent all the other YC founders.
So he'd send an email to a bunch of YC founders saying, like, Hey, what do you need most as
a company?
Like, what would you use most as a company is like a product that you would use most.
And people started, you know, replying to him and describing all these products.
But 30% of them were like, I need help doing x inside my inbox.
And these are all founders.
So it was like, I need help doing hiring in my inbox, I need help doing sales in my inbox,
I need help doing fundraising, like, it was all these founder use cases, and they were
doing them all over email, and they just needed some product to help them with that.
And so that that kind of solidified the idea for us is that, hey, like, yes, we were thinking
of it as a sales CRM use case in email.
But really, this is like, every business process goes through email.
So like, let's build that thing.
It just feels like it was meant to be where you're already kind of solving this issue
with your inbox and all the sales stuff.
And then everyone's like, Hey, we really need help in our inbox.
It's like, well, this isn't a sign.
I don't know what it is.
It's right.
And again, super lucky.
All those people that responded, yes, like PG for that email to us.
And we just like you, those were our initial customers, like we just reached out to them
like, hey, this is we're building exactly this.
So like, you know, here it is.
And so that's how we got our initial few customers to it's one of the like most touted benefits
of going through Y Combinator is that you have this giant batch of companies who all
are trying to get ahead, they all need to pay for products.
And like, they're your first users, it can be your first customers.
And I think people who are building outside of that, like, if you're trying to bootstrap
a company today, it's super underrated to just make friends with other founders to go
to networking events.
I mean, now it's all online, but there's a ton of webinars and like, online meetups and
accountability groups and stuff like that, where you can just like be friends with people.
And those people are trying to start stuff and they have money, like they will pay you,
they can be your first customers.
And it's much easier to do that than it is for like, your first contact with customers
to be like, attempting to launch on product count.
No one's ever heard of it.
No one's going to support you up for you.
And no one cares.
No idea who you are.
Yeah, no one cares.
Yeah, I wonder if that's interesting, actually, I wonder if it's like, there's something to
being part of some community that helps breed startups, like either like a university community
where like, your first users are your classmates, or something like YC, where your first users
are your batch mates, or like, you happen to live in Silicon Valley, and like, all your
friends that you hang out with are also techies.
And so they become your first users.
Like I wonder if...
Is that part of like the PayPal mafia or something, like you're part of a startup, everyone there
starts companies?
Yeah, exactly.
Like, I wonder if that's like a hidden advantage for some of these communities, why these communities
produce so many startups is because it's not just YC, it's like, maybe it could be almost
any community that you can leverage to being your first set of users.
I think it's super useful.
I think it's, we're just social creatures, we look like we look for inspiration among
like our tribes and the people around us.
And if you're in a tribe of people who aren't really that motivated, and they're not starting
anything, and they're not really working hard or anything, you don't feel like you're going
to feel less motivated, you're going to feel kind of dumb about what you're doing.
Whereas if you're like going through Y Combinator, which is literally the polar opposite end
of the spectrum, it's like you're going to suddenly feel like a crazy amount of energy
to do a bunch of stuff you probably would never do.
I mean, you're literally a computer programmer walking around the streets of San Francisco
knocking on doors.
How many software developers like anywhere else on earth are really doing that?
And I also feel bad for restaurants and storefronts in SF, because God, how many, how many, how
many phone calls?
How many things have they been pitched?
Yeah.
I'm in Seattle.
I lived in SF for 10 years.
You walk into any restaurant in SF, and they've got like 15 different gadgets on their counter
for starting out to pitch them some random stuff.
Right, right, right.
Yeah, I think you're exactly right.
Being around people that are like, maybe just one step ahead of you, but still your peer
group is probably the best motivation because you kind of like look at your peers and you're
like, oh, man, I want to be like that, and they're doing really well, and I need to catch
up to them.
And, you know, at YC, there's definitely like, you know, they don't really tout this, but
there is definitely some social pressure, right?
Like every Tuesday, you get together with all the batch mates.
And what's everyone talking about?
They're talking about like the shit they got done in the last week, and you're like, okay,
I don't want to go to another dinner and not have anything to say, you know, I'm getting
shit done this week to make sure that I have something to say on Tuesday.
Yeah, there's definitely it's not like a it's not like the YC itself puts that pressure
on you, but like they set up the environment where exactly like you want to talk about
progress.
Yeah, that's exactly it.
Whatever environment you're in, like, that's what you're going to care about.
If you were, you know, part of like the rich housewives of LA, you're going to be looking
at like lots of plastic surgery and who can live the most fabulous life and like that's
going to seem the most meaningful.
And if you go into these YC dinners every Tuesday, and it's like whose company is growing
the fastest, like you don't want to be embarrassed and be at the bottom of the list.
So I think that trying to figure out this good social group for yourself is extremely
important.
But also, you know, I think I got lucky with that, like, yeah, I'm not trying to like name
drop or anything.
But like, when I say grad school earlier, I went to I went to Harvard Business School
as my grad school, because I wanted to try these different businesses.
And as an engineer, going into a business school, you're kind of like, you're kind of
suspicious, right?
Like suspicious of this set of people, they're all going to be like finance people or consulting
people.
And like, they're just there to party and they're not really learning anything or whatever.
And so I was like, highly suspicious going in.
But it was actually an amazing experience for me, like ignoring the academics and, you
know, we can talk about it more later, but but ignoring the academics, like the people
that were all there, what surprised me was like, they weren't necessarily like smart
in the classical sense, like, you know, engineers have this, like, you know, they love being
rational and logical, and they love, like, this idea of being smart.
And so, you know, the people at this business school would not have met their definition
of like, being smart.
But the thing I learned from them is that they're just incredibly hungry, and incredibly
driven.
And, you know, you look at these people, and they're not any smarter than, you know, anybody
else.
Yet, they're doing some incredibly ambitious things, and they work incredibly hard.
And I would say that's the thing I learned the most at sort of business school, like
I had a classmate who, in his second year in business school, raised $50 million for
a company he started, you know, at business school, and the company was doing like sort
of e commerce in Brazil.
Had he ever been to Brazil?
No.
Did he know the language?
No.
But what did he do?
He flew down there on weekends, he set up a warehouse, he like hired a bunch of people,
and he raised money, he bought a good domain name, and he parlayed that into more and more
success.
And he did that in like the last 12 months of his time at business school.
He ended up, you know, raising $50 million for this company that like, I don't think
your typical engineer would think of doing that, right, would think that it's possible
or think that they could do it, or just seeing that really like kind of transformed my thinking
of it.
So how did you approach starting this new company in the very beginning, having had
all this inspiration from these crazy hustlers at business school, and having gone through
this sort of like failed, knocking on restaurant doors and trying to sell them a product?
What was your first step?
Your new product, your new idea is streaked to build something in the inbox.
Right.
Well, we knew we had to talk to users, I think a failure mode that we had in the first company,
so the first company was like loyalty points, buy a credit card, and so like you spend on
your credit card and you get points automatically, you don't have to scan anything or any BS
like that.
And we thought like, oh, loyalty points are great, you get free shit, like who's not going
to want free stuff?
Like everybody wants free stuff, right?
Like everybody wants a free sandwich or free coffee or whatever.
And so all we have to do is like sell the businesses and then we're good.
And so we sold the businesses, but like it turns out like the consumers didn't actually
want it, right?
Like if you ask the consumer and you're like, hey, like, do you want a free coffee?
They're like, yeah, sure.
But like, do they want it enough to tell their friends about it?
Do they want it enough to like put up with the bugs in your app?
Do they want it enough to like even download your app and connect their bank account?
Like, no, they don't.
And so we didn't want to make that mistake again with the second product.
And so yeah, we got our initial users through YC and we were just basically like talk to
them.
You know, we built something, show it to them, talk to them, build something else, like just
take their feedback and just build it.
And that helped us a ton.
And to your point earlier about like, you know, pushing versus pulling, like once we
had the sort of product built out, we had a lot of pull.
Users were telling other users about it a lot.
And so like for us, it was mostly about getting on the phone with them, the people that heard
about us and wanted us getting on the phone with them and like making sure that we were
the right fit, making sure like we knew what they were trying to use it for.
So yeah, you can definitely feel when you're on something versus when you're not onto something.
And who was we at this point?
I mean, you've got a co-founder?
Yeah, I was a co-founder of mine.
You know, we had kept in touch in college and I told him like, Hey, I'm thinking of
leaving business school and starting a company.
And he was actually working on his first company.
So he actually had some startup experience, which is great.
And that helped us a ton too.
And he was actually just exiting that company.
And so the timing was just like super fortuitous.
Like, I kind of hate saying that we were lucky because it's not useful advice for people.
But I think maybe the thing to take away there is just like kind of keep in touch with your
friends and, you know, talk about what you're working on and talk about your interests and
talk about your goals.
I think that's exactly it.
People talk about making your own luck.
How do you make it so like the universe just seems to open up its arms and just provide
you the exact person or help that you need at the right time.
And the secret is you just constantly do what you're saying, you broadcast what you're working
on, you broadcast your challenges, your goals, what you're trying to do.
And that's the only way people are going to know how to help you.
Yeah, and I think that goes back to our early discussion of like the 18 month company versus
the like decade company.
If you're building an 18 month company, you have to be like, you don't have time for any
of that or you don't have time to build relationships over a long term.
And so like, you're just hoping that you're hyped enough to like attract all the people
that can help you versus like, you know, for us, for example, our head of engineering,
I met in our YC batch.
And it took me five years to like, he was a friend for five years before he became our
head of engineering.
Right?
Like, so you could say like, Oh, it took me five years to recruit him.
And it's like, yeah, like if you're building one of these long term companies, and you
have to know that you want to build a long term company, but like the things that you
do now are going to be helpful by 10 years from now.
So when did you get to the point where you realized like this was actually going to work?
And it wasn't just, you know, this temporary excitement from having a first few customers
in the door, but it was a long term business idea that you wanted to stick with.
Right.
When people started telling other people about it is kind of when I figured like, Hey, we're
on to something like, you know, always in the back of your head when you're starting
a new company, you're kind of like, Oh, like if this doesn't work, like I wonder what else
I could pivot to and like, when people started telling other people about it, then that kind
of thought in the back of my head kind of went away.
I was like, Oh, no, no, this is a thing.
This is a real thing.
Like if people are willing to tell other people about it, that means they're finding value
in it.
But that's what I kind of knew is working.
And then just getting on the phone with them, we started doing pricing discussions, because
you know, as I talked about, we were free for a while.
Once we started doing pricing discussion, that was another sort of proof point for me.
Give me like a snapshot of what this actually looks like.
Because I think a lot of founders are, are good at like the code part, they're building
the product, they're like making something take shape.
You know, maybe they see people signing up or whatever.
But like, you keep talking about getting on the phone with people and like having conversations,
how are you actually convincing your customers to get on the phone with you?
And then who were these customers?
So initially, because people were telling other people, people would sign up on our
website, or they would discover us in the Chrome Web Store, because extension streak
is an extension built into Gmail.
And so the way you install that extension is you go to the Chrome Web Store, and it's
an app store.
And back then, there weren't a lot of apps in there.
And so a lot of people would discover us there.
And so that was a little bit of fortuitous timing as well.
And so they would discover us, and then they would write in into our email support, we
only had email support.
And they'd write in questions like, Hey, how do I do x like how do I take meeting notes
or I'm getting on a call with a customer and I'm using your product as a CRM?
How do I take call notes?
And we're like, Oh, we didn't know people did that.
Okay, let me email this person back and be like, Hey, we don't have that right now.
Or you could do this weird workaround, like you could, you know, take notes in a Google
Doc and then just like link it into the CRM.
But like, can I talk to you about that use case?
And basically, we hear that kind of use case enough, and we'd be like, Okay, time to build
it, right?
And so like, maybe the first time you email them back and learn a little bit more, and
you kind of like bank it.
And then you hear it a second time, a third time, and then that becomes like, Okay, this
is something that people really want.
We got to build this and like, to make sure we're building it right, let's like talk to
them first to make sure we're not building, you know, the wrong thing.
We weren't trained salespeople.
We did sales for three months.
So we kind of knew the basics, but we didn't know enough of the space to just like build
it off of our own knowledge.
And so we definitely had to talk to other people.
And so strange to enter an industry where you're not the expert, you didn't work at
Salesforce, you don't know what people who use CRMs really need.
And so you're kind of just winging it.
But on the flip side, you're solving your own problem.
So you kind of know what like you need.
And that'll get you a little bit of the way there.
Contrary to popular belief, it's not going to get you all the way there aren't 100 million
people who are exactly like you.
And it turns out if you want to grow, you've got to actually listen to this feedback and
figure out what other people want.
This word of mouth thing is also pretty interesting, where you have people telling people about
your product.
And I think the common wisdom is to get word of mouth growth, what you do is you have to
build something that's 10 times better than what everybody else has, it's got to be so
much better than people use it, they don't just, you know, continue using it happily,
but they continue using it and telling everybody else how great it is.
And that's where word of mouth growth comes from, based on someone who's actually been
in this position, and people were spreading your product through word of mouth.
How true is that?
And are there other factors that contribute to people sharing what you're doing?
I think it's definitely true for us, because I think there's a caveat to it.
Like we were 10x better in one area.
In a bunch of other areas, we were actually 10x worse.
Like we were really bad at most things, but in this one specific area, our Gmail integration,
how deeply we integrated with the UI of Gmail and the backend of Gmail, that experience
was kind of sublime.
It's kind of more common now, but back then, it was kind of a revelation to see that like,
oh, the place that I'm doing all my work, my email, is also the place where I'm tracking
all my work.
That part of it was definitely 10x better.
And so when people emailed us, they're like, hey, like, we love the product, we're totally
sold on a Gmail thing, but you can't even take note.
You can't make date column.
I can't record a dollar amount, and you have no support for currencies.
How am I supposed to use you as a CRM?
And we're like, a lot of those things we still haven't done to this day, because it's more
important to be the 10x better.
And the way I think about it is, that's the first phase of product development, is that
10x better phase.
Then the next phase is getting all the rest of the stuff to just meet a minimum bar.
So we spent a long time, like CRM is kind of a product where there's just so many things.
There's so many features that people expect.
And I think email clients are kind of like this as well.
Building email clients is so hard, because there's just so many features that people
just depend on, like, oh, I need to mute threads.
I need to have email signatures.
I need to have all these things, multiple inboxes, split panes.
And so to even build an email client with your one unique insight, you have to build
all these other features just to get people to use it.
So we spent a lot of time after building that 10x feature, just getting decent at all the
other stuff.
At what point did you decide that you don't want to try to be a billion dollar company
and that actually just charging people money for this 10x better product is a much better
path?
I would like to say that we were super thoughtful and smart about it.
It wasn't like a purposeful decision.
It was like, hey, we're growing at a fast clip.
And we're starting to charge money.
And we're profitable.
And so there's no huge need to raise money.
But maybe we should do it for defense.
But that's what most companies do when they're on this billion dollar track.
They raise money.
And so maybe we should do that.
And so we tested the waters a little bit.
And we could have raised money.
It would have been a slog.
It would have been not on the greatest terms.
And we looked at that, and we're like, oh, man, that's going to be six months of pain
to raise this money.
And for money that actually we can't even...
What would we even do with?
We would sit in our bank account because we're not money constrained right now.
There's nothing that we want to do where we're like, oh, we don't have enough money to do
that.
And we have no pressure.
We're not going to die because we're profitable.
So why are we going to go through this pain of raising all this money and get not great
terms?
What's the reason?
And so we basically just kept pushing it off.
We're like, hey, is now the right time?
Nope.
We're profitable.
We still have money.
And we can do whatever we want with the money we have.
Okay.
So maybe in six months, we'll try again.
And we kept pushing that decision forward and forward and forward.
And it basically never came to a point where we needed to raise.
And so I'd like to say it was some master plan, but it definitely wasn't.
Was there a moment where you just accepted, you know what, this is never going to happen?
Well, if you ask me today, I think there's still a chance that we go raise money.
It wouldn't be the type of money that we would have raised one year in like a Series A round
or something like that.
If we were to go raise money now, it's more likely to be like a growth round or something
like that.
But I'm not philosophically opposed to any of these ideas.
This idea of never raising money or this idea of, oh, you must raise money.
I don't buy into the philosophies behind those.
I just am pragmatic about it.
If we could use money to help reach some more goals, then great, we'll do that.
And if we don't need it, then we won't do that.
It's like, yeah.
It's the reasonable mindset.
And people don't want to hear a reasonable mindset.
They want the extreme.
They want the...
Yeah, it doesn't make headlines.
Yeah, it doesn't make headlines.
But I think it's becoming more common.
There are more investors nowadays who are figuring out ways to profitably invest in
these slower growth, indie hacker companies.
And they're also, I think, compared to when you started Shriek and when I was in YC in
2011, there's also just much more understanding in the high growth investor community of building
a business that's profitable, where you actually charge money.
So I feel like both sides are converging on this reasonable center, which is like, yeah,
evaluate your options, try to build a business that has good business fundamentals, and go
from there.
It's not as religious as it used to be.
Yeah.
And at the end of the day, if you're not providing value to users, all of this is for moot anyways.
All of this is moot anyways.
And if you are providing value to users, all of this is also moot, because it'll be obvious
what to do.
It's the only reasonable advice is build something valuable, and it'll be easy to make decisions
after that.
And by the way, some of these companies that slower but growing profitable businesses become
juggernauts after many years.
They compound.
Atlassian, what?
They didn't raise a dollar for the first 10 years or something.
And then they raised Sequoia money and then IPO'd or whatever.
And so I don't think it's ever the case that doors are closed to you just because you've
taken an approach in the past.
Yeah.
I had Jason Cohen on the podcast, who's sort of like a bootstrapping hero.
And he bootstrapped three or four companies to over a million dollars in revenue.
And then his last one, it was doing the same thing, same trajectory.
And he's like, you know what, I'm just going to go for the gold.
He hired a CEO, he raised a ton of money, and now he's doing something like two or three
hundred million dollars in revenue.
It's crazy.
Amazing.
Amazing.
You can bootstrap and fundraise.
You can fundraise and then never raise again and just sort of live off your profits, start
different companies and do different paths.
What's striking to me about your particular story is that you almost followed what today
is like the bootstrapper playbook.
You pick an idea where there's a proven sort of track record of companies are making money
in this space.
And it's kind of boring.
It's kind of straightforward.
It's CRMs.
They already exist.
But you're not trying to enter some sort of winner-take-all social networking market
or something like that.
You're just trying to create a business.
And then in order to compete with everybody, instead of targeting their customers, you
niche down and you pick a really specific use case, which in your situation was the
email inbox.
Founders.
Exactly.
Email inbox founders.
And so ultimately, yeah, as you said, you're 10 times better in this very narrow scope.
And you're 10 times worse than every other scope.
But it doesn't matter to you because you're a fledgling company.
You don't care if you're only making a few dollars.
You're just getting started.
Right.
Do you remember your very first sale, the very first time anyone actually paid you for
Streak?
Yeah, it's kind of crazy.
We weren't charging for the longest time.
And we kind of decided, hey, we should probably start charging money just because at some
point, we need to have income.
And actually, it was more being afraid of our previous experience with a previous company
where actually, people didn't really want it.
And so we were worried that, hey, it's free now and people are using it because it's free.
But if it was paid, people would never use it.
And so we wanted to just double check that.
But again, we didn't want to build a billing system or pricing page or anything like that.
We were lazy.
We called one of our biggest customers, which was Uber at the time, had, I think, 50 users
using us or something.
And we were basically like, hey, it's kind of time to pay.
And we figured this would be the easiest sale because they had tons of money.
This would be the easiest and tons of usage of the product.
So we're like, hey, it's kind of time to pay.
I remember the guy on the phone was basically like, we're not paying you already.
We don't already pay for this product.
I'm like, no, it's free.
And he's like, I can't believe we're depending on your product, which is not paid.
We're not paying you any money.
I don't know what kind of support we're getting.
I don't know if you're going to be around in six months.
But we use your product for a critical part of our business.
I can't believe we're not paying you.
And so that was the easiest sale ever because they really wanted to pay.
And so he's like, how much is it?
And I just made up a number.
I said $10 a user a month.
And he's like, OK, done.
Hang up.
That was it.
And so that was the first sale.
And so the next call sort of did the same thing.
So what is the price?
And I said, oh, it's $20 a user a month.
And they're like, OK, done.
Hang up.
And I basically just kept doing these phone calls and kept raising the price by $10 until
somebody said, eh, that seems a little like, as soon as I got a little bit of pushback,
I was like, OK, that's the right price.
I did the same thing with Indie Hackers when I had sponsorships back when I first launched
the site.
I had a list of basically, OK, these are my dream sponsors.
These people have interacted with Indie Hackers before.
I'm going to go through one at a time and just email them and call them and just say
a price.
But I went backwards.
So my dream sponsor is actually Stripe.
And they're at the very bottom of my list.
I was like, OK, I want to talk to them last after I perfected everything.
But you went after the juggernaut immediately.
I just wanted somebody that was going to say yes.
We could see their usage internally.
And so we knew that they were depending on the product.
And so I just wanted to get to a yes.
And I think that a lot of startups is just building momentum.
And it felt good to have that for sale, that second sale, and kind of just built up some
momentum.
And then even later, if we got some pushback on the pricing, that didn't feel bad because
we sort of built up this momentum.
Yeah, you locked in those yeses.
I should have done it that way because I got a lot of no's at first.
It's pretty discouraging when it's like, no, no, no, we can't afford it.
Nope, sorry.
Yeah, it's all momentum-based.
So at this point, you're charging for your product.
You've got some money in the bank.
You've got Uber using you.
And you know you're actually building something that people care about, which I think is worth
actually diving into for a second, because you mentioned earlier with your sort of loyalty
program thing you're working on, people told you they would pay for it, but they didn't
care that much.
It wasn't like if your thing goes down, people are going to be in tears on the street because
their life is ruined.
No one really cares.
It's kind of like this unessential thing, whereas what you're doing with Streak was
very mission critical.
Uber is using it.
They're concerned that if your company goes out of business, they're going to be screwed
because so much of their data is in what you're doing.
And I think a lot of founders have trouble with this when they're first trying to figure
out what to work on.
Well, I don't have a big team.
I'm real small.
Like, can I build something important and mission critical?
Like, no, I don't trust myself to be able to do that.
You know, I'm too small.
I can't compete.
So I've got to go build something that solves like a really small, simple problem that's
really cheap.
And people will pay for it.
You know, I'm just not big enough to really try to go after an important problem.
From your perspective as somebody who's done both of these approaches, what would you say
to a founder who's convincing themselves of that right at the beginning?
Oh, man, based on our experience, again, this is only our experience, but like when we had
something free, it was harder to sell than when we had something that was paid for.
Actually, it was better than free.
We would give you free stuff.
We would give you coffees and sandwiches.
We would give you free stuff and we couldn't get people to pay attention.
And it's because like, that's not the thing that's on their mind every day.
They don't think like in the morning, they don't wake up and go, hmm, how am I going
to get my free coffee today?
Like I really got to think, be thoughtful about the tools I use to get my free coffee.
It's like, no, they don't give a shit.
But for us, when a sales manager wakes up, they are thinking about, hey, my sales team,
I need to know if they're doing well, we're paying them a lot of money.
I need to organize our deals.
I want to look at all of my team's deals and see what's going on with them.
It's a really important thing for them because they're thinking about it all the time.
When they're in the shower in the morning, what are they worried about?
What's the critical piece of their job at sales manager?
It's like, am I going to hit my quota this quarter?
And that's the thing they think about in the morning.
So giving them something that takes away that pain or takes away that worry is like so much
easier because it's on their mind.
It's at the forefront of their mind.
So I think maybe the generalizable advice is find the type of person who knows what
this persona has at the forefront of their mind, what's their biggest pain, and then
make something that makes them feel less stressed.
Do that and there'll be some pull.
Now, obviously, that's easier said than done.
The hard part is knowing the persona and knowing what makes them stressed, knowing their problems,
knowing their motivations and their incentives and that kind of stuff.
And so again, I guess that goes back to talking to people.
That's so unintuitive, especially if it's your first time starting a business.
People don't buy things because they're cheap.
They buy things because they're valuable.
And I could probably sell you a $10,000 car way easier than I could sell you my $10 pair
of socks.
And the people who are aware of this don't spend a lot of time thinking about like, okay,
what are my customers find valuable?
What's the most important thing on their list?
They instead get stuck trying to lower their prices and maybe that'll get people to buy
or trying to add a bunch of random features and maybe that'll get people to buy and it
doesn't work.
So it's always that temptation to just start building something.
And as an engineer, I totally feel that even today.
At Streak, we're working on a new product that's going to be integrated into Streak.
My first temptation was like, oh, let me just mock this out and let's get the team to build
it and we're good.
And that was my first instinct.
And even then, I think I'm probably the most qualified person to take that approach because
I've been talking to these users for eight years.
Even still, I'm doubting myself.
And so I had to hold back and like, let me do 10 user interviews before I actually spec
something out or mock something up.
Just let me just make sure.
And honestly, I don't think it's that bad to build a few features to test the waters
a little bit, but definitely time boxing.
The worst thing to do is to go for six months just building stuff that nobody's using.
I would say a couple of weeks, build something enough to get a conversation going with something.
There's actually a great conversation starter to be able to send a little feature or a little
toy or whatever you built to a prospective customer and be like, hey, I built this small
thing.
I know it's not everything that you would want, but what's your feedback?
What do you think about it?
I think that's an easier way to talk to people because most people don't answer your cold
emails.
It's also, I think, becoming more common for people to build these really small MVP-ish
things.
In part because, number one, there are more people who are developers who can just do
it, but also because it's been this rise of no code and low code tools where you can whip
out a landing page or a mock-up or a concept of a feature using Zapier or something and
almost no time.
I meet indie hackers all the time who are like, yeah, I built this thing and I'm like,
oh, this is incredibly impressive.
How does it work?
And they're like, oh, it's just all these things I sitched together in the backend.
It's going to fall up.
It's held together by duct tape.
It's going to fall apart at the lightest breeze, but I built it in a day and you can go and
show that to people.
I know there's a lot of hype around the no code thing and I think there is something
to it exactly the reason you're describing, which is it's a great sales tool.
It makes you seem bigger than you are.
To your point earlier, how is somebody going to take me seriously?
I'm just one developer, but if you use Webflow and a good template off Webflow and hacked
some stuff together using Zapier, there's almost no difference between what a customer
would see, between you, a single developer in your basement and a team of 20.
It looks roughly the same on first blush and so you can fake it till you make it.
There used to be stories of startups who would hire a bunch of people off Craigslist to just
come into the office and sit in desks and pretend they were employees when a big sales
meeting happened on site, just to make them look bigger, but I guess no code is maybe
the new way of making yourself look bigger than you actually are.
I think it's great from that perspective, but don't buy into the hype that this is going
to be the way we build apps in the future.
Maybe some internal tooling is useful, but even then, one of the companies I'd love to
plug is Retool and they're a low-code platform for internal tools.
That I think is the right model.
The customer is internal people who have a lower, I wouldn't say quality bar, but design
or aesthetic bar.
You still code a little bit.
There is still JavaScript in there and it's actually meant for engineers to build, but
it just amplifies their efforts.
That's the way I see this low-code versus no-code thing.
I'm not a huge believer that the no-code thing will replace how we build apps.
Well, you heard it here first, folks, I'm Lee Moani, no-code hater, he's a doubter.
Honestly, I tried a side project using nothing but no-code and there was a surprising amount
of code in no-code.
Even if it doesn't look like coding, you're using their drag-and-drop builders and building
if statements and stuff like that.
It's coding.
Of course.
You want to put your own logic in there.
You want to react differently to different situations and have loops and repeat things.
Eventually, you're just a coder using kind of shitty coding things.
Maybe what will happen is it will get people more comfortable with coding.
Once they realize that what you're doing is actually kind of coding and then we actually
take a tutorial for learning how to code, some of these concepts now seem familiar because
you've done them in no-code, you'll be more willing to take the leap and go further.
I think the tool that's already done that is like spreadsheets.
Excel and Google Sheets has already made programmers out of millions of people that don't even
know they're programmers.
The problem is they can't make the jump from sheets to coding because spreadsheets are
like a functional language.
Most beginner coding tutorials or whatever are all imperative.
It seems like there's all these environments that you have to set up and stuff like that,
whereas a spreadsheet, you just open it and start coding.
That's why I'm a huge, huge believer of things like Darklang or Repolent, those kind of platforms.
If you can take a spreadsheet coder and make them a regular coder, that's the big opportunity.
I've taught a few people to code, just friends and family, and the biggest hurdle is always
the environment.
It's always like it takes them hours just to get to the point where they can write any
code somewhere where it's actually going to run or they're writing in a random box on
this website that doesn't correspond to where they write it in real life.
Just getting their computer and their environment set up to be able to actually compile or interpret
code is just a huge hurdle and people give up because it doesn't seem worth it.
Yeah, if you think about it, spreadsheets, it's like the ultimate programming environment.
No setup, you see all the intermediate values at all times.
Your program is always running.
It's easy to debug because you can see the state throughout the whole thing.
And you type the code into the place where the interface is.
It's not like type it into a text file and then see the webpage somewhere else.
It's all in one environment.
Yeah, it's like the ultimate programming.
I'm not surprised that it has millions of programmers.
All right.
If you're listening and looking for a business idea, I think teaching people to code is always
lucrative.
People pay thousands of dollars to learn how to do it.
The number of ways to teach people to code is pretty much infinite because people have
different learning styles.
And so if you want to take Aleem's spreadsheet idea and run with it, then you should go for
it.
Give them a cut.
With your particular product streak, I think I'd be remiss if I didn't remark on the technical
challenges that you faced because I also build products in the inbox and it's not easy.
You have a lot of platform specifically because you're building the CRM that is directly integrated
into Gmail.
And Gmail did not have an API for modifying their user interface.
They weren't like, oh yeah, we support this, this is fine.
They're randomly, and I know this from my experience, they're randomly just changing
their interface all the time without any sort of warning.
They'll deploy tests on some users where some people will have their inbox tab moved to
the left or some people get the new features and some people don't.
And you as a developer trying to build on top of all this can be kind of blind.
You have no idea why your app is breaking for some people and not for other people.
And at least if you're anything like me, I always have this fear in the back of my mind
that if I keep building on top of Gmail, one day they're going to flip some switch and
I'm screwed.
My whole company is done.
Did you not worry about that?
Yeah.
I mean, it was the 10x feature that made users want us, but it was also the biggest risk
in our company.
We got that same sort of pushback from investors.
We got it from potential employees.
We got it from just like customers, like even customers, because our customers were actually
technically savvy.
They were always worried that Streak wouldn't exist in six months or whatever.
So actually, that's one area where we did actually, and the no-code thing would not
have helped us here at all, we did have to invest a lot of technical effort to prove
that model out and prove that we could be resilient to Gmail changes.
So not only did we want to show that, hey, we can build a complete app inside of Gmail,
we also wanted to show that regardless of how Gmail changes their implementation, we're
still okay.
And so we built a bunch of systems that made that possible.
So we had systems that monitored Gmail's DOM to make sure that everything was where we
expected it.
And if something wasn't where we expected, then it would alert us, and we would go look
into it like, hey, is Gmail rolling something out?
Because Gmail rolls things out slowly, and so maybe 1% of our users would see the slightly
weirder DOM, and we want to make sure that we're still compatible with that.
And so we had all these tools and systems and automated testing in place to make sure
that that was super solid.
And all that technology that knew how to deal with Gmail, we actually opened it up.
We opened it up for other developers to, if now you want to build an app on Gmail and
you don't want to go through the same worries that we had to and go through the same Herculean
effort that we had to in dealing with Gmail, we have an SDK that lets you program against
high-level APIs, and then we handle all that stuff dealing with Gmail.
We react when Gmail changes and all that kind of stuff.
And so, but yeah, back in the day, it was a big risk.
One thing that helped the risk as well was that I worked at Google.
And so I kind of knew the people that were on the Gmail team.
And so...
I knew it.
I always wanted to ask you, how many people did you know at Gmail?
Because it's inordinately stressful.
Yeah, I knew a few engineers on the team.
I knew a few product managers on the team.
And of course, they couldn't officially endorse it.
They were like, hey, here's our two-year roadmap, and we don't think we're going to change these
parts of it or whatever.
And so that gave me a little bit of comfort.
But the thing that gave me the most comfort was when they actually said, here's my two-year
roadmap.
The time it would take them to deliver that two-year roadmap was actually like five years.
And so like Gmail, it's a great platform to build on because it has a billion and a half
users.
But it's such a slow-moving platform that I'm not worried that Gmail is going to keep
changing stuff that would affect us.
We're way faster than they are.
When they change something, we react in a few hours.
And for them to change something takes them years.
And so it's not a huge, huge deal.
A lot of people today starting startups are dealing with this issue of platform risk.
Maybe not code-based platform risk, but more like distribution-based.
If I start my blog on Medium or Substack, am I going to be locked into that?
If I start on YouTube, am I at basically the whims of YouTube?
How do you think about de-risking that?
Or did you just 100% go, we're all in on Gmail.
If we're dead, we're dead, but we don't care about the risk.
So what's interesting is that yes, our product lived in Gmail, but our distribution didn't
come from Gmail.
Our distribution came from the Chrome Web Store.
And so that was the only place you could find us before was in the Chrome Web Store.
And it was great because not a lot of competition, like I said, and we're getting tons of installs
from there.
But that distribution channel was like an arbitrage, like a lot of traffic for not a
lot of people knowing about it.
But these arbitrages, they disappear.
And so over time, we went from having 90% of our traffic come from the Chrome Web Store
to 10% of our traffic coming from the Chrome Web Store.
And so I think for other founders, take advantage of these weird distribution opportunities,
but make sure that your product is agnostic of where the distribution comes from.
You could switch to another distribution channel.
But it's still useful to build on Medium or Substack or whatever when there are these
weird arbitrages.
But eventually, you got to build your own.
Now, 90% of our traffic comes direct.
We don't do marketing, outbound marketing or anything.
It comes direct because we've built a user base that knows about us, that likes us and
tells their friends about us.
And so now we have it in our control.
But there was a time when if the Chrome Web Store turned us off, we would have been dead.
When you're looking at those numbers falling, what are you thinking?
How do you model that process in your head of like, oh, shit, this distribution channel
might not work forever.
And you're not quite sure which ones to explore.
The writing was on the wall.
The Chrome Web Store first launched.
Anytime you were in the Chrome browser and you press the new tab page, there was a giant
link for the Chrome Web Store.
And you had 300 million people using Chrome.
So obviously, there's going to be a ton of traffic to that thing.
And you go to the Chrome Web Store and there's like 20 apps and they're all shit.
And so we're like, okay, this is not going to last.
People are going to see this, that this is not going to last.
And so we can use it to build up our user base.
But really, if we need to find other distribution channels.
And for us, the distribution channel was just word of mouth because we saw that even though
our Chrome Web Store traffic was going down, our overall traffic was going up.
And we started asking, where is this traffic coming from?
And it was all people recommending other people and they were like, okay, we're not working
anymore.
Crazy.
It's such a good, good channel to have word of mouth because it's the one thing that'll
last even if everything else goes away.
Even if you never find a replacement for the Chrome Web Store.
Even if you never hit on influencer marketing or become an expert at SEO.
If your users keep telling other users and they're churning less often than they're recommending
other people.
And that's just an engine for like indefinite permanent growth.
And you don't really have to invest a lot of money in marketing and growth and getting
bigger.
That's great.
100%.
So where's Streak at today?
I mean, obviously, you're up to 30 people, you're generating millions in revenue.
What's at the top of your mind?
And what are some like recent things you've been working on?
It's kind of crazy.
We've been working on stuff that's like been a problem that our users have told us were
problems for like years.
And we kind of never had a good solution in mind up until very recently.
And we launched that two months ago, basically, we call it Streak 3.
It's like a third major version of the Streak product.
It's stuff we've wanted to do for like literally six years and haven't either had the technology
or haven't really understood the product well enough, or understand our users well enough.
And we finally got around to doing it.
So we're still working on things that are pretty fundamental.
It's not just...
And that's what I mean about these sort of longer term companies.
It's important that we're still solving hard problems because our team, that's what we
enjoy doing.
And so there's still plenty of those problems left in terms of goals.
We want to expand our product suite.
We want to offer new products.
It is kind of cool to be working on new products while having existing products.
Because an existing product, making sure that 10x part is still really solid, you're making
sure all the other features that you have to be table stakes that you're getting all
those done.
So we get to do a little bit of that kind of product development.
We also get to do early stage product development where it's, hey, we know nothing.
We know nothing about the problem.
We want to talk to a bunch of users.
We're going to build something really small first.
We're going to see how that works.
We're going to think about how we're going to do distribution.
Even though it's like a single company, I feel like larger companies, we're starting
to offer multiple products.
And that lets you have a way of keeping things fresh and not pouring.
You've been around for close to 10 years now.
And I think rebuilding your product from the ground up is exactly what they warn you against
doing as a developer.
It's like one of the 10 developer commandments.
So how do you get away with that?
And what's your rationale?
Our users, they just tell us, hey, this thing sucks about your product.
It could be way better if it worked this way.
And the way they wanted it to work was fundamentally different in a certain area.
So we have to rebuild a huge part of our product.
And also part of it is also packaging and marketing because on the engineering side,
it's really, really good practice to launch features as they come.
Small tweak here.
Launch it.
Small tweak here.
Launch it.
And as fine grained as you can, just continuously be launching.
It's really good for your existing users because they see the steady improvement.
And it's really good for engineering because it's easier to do that kind of deployment.
But it's not great for marketing because if there's a customer that hasn't seen you around
or checked you out maybe a few years ago, there's no reason for them to look at you
again unless there's some big new thing and you can't make a mountain out of them.
It's hard to make a mountain out of Mulhill when you just dripped out one small little
feature and you're like, hey, come check us out.
We just did this one small little thing.
And it's like, that's not really a marketing event.
Press doesn't want to pick up on you.
It's not worthy of a product launch.
It's hard to really talk about it as some new thing that you should check out again.
But if you take all those features that you've built up and launched individually, even though
they're already launched, we launched a lot of Street 3 before Street 3 launched.
And you take all those features, you bundle them all together and you say, okay, this
is Street 3.
Now I'm going to tell the world about Street 3.
It's this bundle of things and I'm going to market it, I'm going to tell people why it's
new, why it's different, why it's a different product than what they may have tried in the
past.
Emailing a bunch of our old users and saying, hey, we have a package of things now that
is fundamentally better.
So yeah, that was another reason we wanted to make a big launch.
Yeah, it's the best of both worlds.
Sort of drip out features, but then package them together in a huge launch so people don't
realize that you just drift them out the whole time.
And some companies do the exact opposite.
Google drives me crazy where they'll just abandon a product.
For all intents and purposes, you see nothing happening.
I use Google Play Music for whatever reason instead of Spotify.
And it's like they just didn't improve or update this product for seemingly years.
And it turns out that behind the scenes, they're building this entirely new thing called YouTube
music.
But as a user, I'm just pissed because I'm like, well, what's happening here?
You don't care about it.
You've abandoned it completely.
Why am I going to keep placing faith in you when you're not even working on your own thing?
God knows how many engineers.
You can't spare a few to fix these obvious bugs.
You're like, oh, no, no, no.
We've got this big packaged thing coming.
Don't worry.
Google Play Music.
But it's like, by that time, I've already left.
So if you can sort of drip them out and then make this announcement that no one has to
know is really just a bunch of stuff you released a year ago, I feel like that's the win-win.
I think it's a good tactic for startups.
Because I think users want to know that this product that they're using from this tiny
company is going to be around.
And so when they get a steady set of emails, existing users, we try to email our existing
users at least once every two weeks with something new that happened.
Like, hey, we just launched this thing.
Hey, we just fixed these bugs.
Hey, we just did this.
Again, it makes you seem bigger than you are because it gives users confidence that you're
going to be around and that you're investing in this thing.
And they made a good decision like, hey, maybe the product you're using right now doesn't
do all the things that you want it to do.
Oh, but I know that street team, they just crank on features.
So maybe it's coming soon.
I'll stick around.
It helps retention.
It helps so many things if you just advertise to your existing users that drip.
But new users, you do the package.
There's a lot of, I think, very common startup advice that I want to get your opinion on
having actually lived through it.
Some of it's older.
Some of it's newer.
One of the older, I think, takes is that market trumps everything.
I think it was Marc Andreessen who first started saying this maybe 10 years ago, like, hey,
I'll take the market over the team any day.
And if you have a great team, you give them a crappy market, they're going to be dead
in a few years.
If you take a mediocre team, you put them in a great growing market, they're going to
crush it.
I think the market basically sets the cap.
It sets the upper limit on how big the company can be.
And so you can have a great founder and a great team working on a market that is capped
at $10 million.
And they'll execute the hell out of that and get to maybe 90% of the market.
And then you have the same team, same great team on a market that is maybe a $100 million
market.
They'll get to $90 million.
And they'll always get there.
They'll always get where they're going to go in terms of percentage of the market.
And so I think for founders deciding on what market to go after, it's like, it doesn't
have to be the billion dollar market.
We've shown that you can be very profitable and grow very well in a $10 million market.
And you just have to set your expectations that I'm going to execute well, I'm going
to make a $5 million a year business.
That's what I want.
I'm happy with that.
Or no, no, no, I want the $100 million business.
And I want there to be more competition.
And I'm happy to go against that competition or whatever, and execute there.
I think both can be successful.
It's kind of a non-answer.
But both can be successful, depending on what you want.
But you don't have to go after the big market.
You just have to do well in whatever you're going after.
And nowadays, because everything's global, every market is big enough to have a great
life.
If you're successful in software now, it almost doesn't matter the size of the market because
every market is big enough for you to have a great life.
How important do you think it is to be early to the market and be one of the first players
doing the particular thing that you're doing?
I don't think it's that important.
If another CRM came along that was in Gmail, I think they would do great.
Because the markets are just so big now.
The market for all these...
There can be multiple players.
And you can just carve your niche infinitely narrow to do so well in that niche.
Yeah.
Gmail is like, what?
20%, 30% of the email market?
Yeah.
A billion and a half.
Hundreds of millions of users.
A billion and a half users.
Nuts.
And the streak certainly doesn't have a billion and a half users.
A billion and a half users.
A lot of space there.
Correct, nor would we want it.
What do you think about this new mantra of building an audience before you start a business?
Back in the day, everyone just leapt in and created stuff.
Nowadays, a lot of people, even developers, are saying, I'm not going to code anything.
I'm going to write or I'm going to teach or I'm going to build up a Twitter following
or build up an email list.
Then once I have an audience of people, I'm going to then figure out what I'm going to
launch.
I think it's great that there's another new distribution channel that exists that didn't
exist before.
It's always been hard to get attention.
That's never going to change.
It's never going to change that you need to occupy some percentage of a person's attention
for them to care about you.
How you get that attention is there are crowded areas and so it's harder to get people's attention
and there are less crowded areas.
This is a new area.
It will get crowded.
This community building approach will get crowded.
It's a nice arbitrage right now, but it will get crowded because eventually, how many
communities can you really be a part of?
How many podcasts can you really listen to?
There's a few podcasts that I listen to where I really respect the person that's doing it
and I want to listen to all their stuff, but how many could I possibly listen to?
Maybe five of them, maybe 10, but it's going to get crowded eventually where now you're
just going to fight for attention in community building.
Just like you were fighting for attention in distributing your product, it's going to
end up being the same thing.
I think while there's an opportunity right now that there's an arbitrage opportunity,
definitely take it, but know that it may disappear.
I actually like the way that things are headed where things are getting crowded because it's
unfortunate if you're trying to build a billion-dollar unicorn.
If it's going to turn out where there's a million little distributed communities or
distributed newsletters and there isn't one winner who takes the entire market, that really
puts a cap on your ambitions if you want to capture the whole market.
But there are actually a ton of markets like this that have worked for ages, in fact pretty
much the entirety of mankind since before the internet, where there wasn't just one
player who just dominated the space.
If you wanted to start a school, you're never like, my school has to teach every student
on Earth.
Otherwise, my school's a failure.
No, it's cool if your school has like a few thousand students and there's like a million
other schools.
I think the same is true if you're starting one of these more audience-focused aggregators,
like a newsletter or podcast or community.
Maybe you only have 1,000 people or 100 people and that's good enough for you to make a living
on.
If you can do that, that's great.
If it gets super crowded and you don't get to a million people, that's fine.
You can take whatever you have and parlay that into some winner-take-all market, or
you can just be happy running your business the way it is.
I think that's true, but I wonder how hard is it to build one of these communities?
We're basically saying build a community, like a niche community of people that really
enjoy your writing and then figure out what product they want and then build that thing.
That makes sense, but isn't that just shifting the problem from build something users want
to write something users want and then build something users want?
It seems just as hard.
Exactly what it's doing.
It's equally as hard in terms of the challenge that's posed to you.
I think the actual execution of it is slightly easier just because your feedback loops for
writing and talking are just insanely tight.
You can write a blog post in a day.
In fact, Alex Wilhelm works at TechCrunch and when I interviewed him, he'd written seven
articles in the past 24 hours.
That guy just has an insane feedback loop where he's like, oh, this is really catching
on.
Oh, I wrote about no code.
Everyone really loves this.
Whereas if you're coding something, you could talk to users, et cetera, et cetera, and it
takes a while.
I think you're completely right.
You've just shifted the burden and you still have to go through the exact same process.
But it's a little bit of a faster process to go through, luckily.
Okay, so maybe that's a faster way to find your users than building a product as a way
to find your users.
I think so.
But anyway, obviously, the route that you took has worked out spectacularly well for
you.
I've been putting out some polls on Twitter and I think it's the route that most software
engineers want to take.
They want to build a SaaS company.
Yeah, I don't know if what we did would have worked today.
And conversely, what works today wasn't available back then.
What would you say is the biggest lesson that you've learned from what you've done that
an early stage or aspiring founder could really take away?
It kind of goes back to what we talked about at the beginning, but I think it's important
to understand that if you're trying to build a big company, it's going to take a long time.
No matter what route you take, if you do the VC-back route or you do the growing profitably
route and become huge that way, both routes take a long time.
It's kind of like advice that's been hammered home, but you kind of have to figure out are
you going to enjoy doing this thing for many years?
That sounds like an impossibly high bar, but it's not as bad as people think because you
have to remember that as your role as a founder, you get to change what you work on.
Like at the beginning, I built our backend, I built our iOS app, then I started doing
a lot of design.
Now, I do more management and more product development, and so you get to change what
you work on.
But the great thing is you get to decide what you're working on.
And so it's a little bit easier than, oh, you're building a tool for lawn care professionals.
You don't have to love and want to live and breathe lawn care professionals for the next
decade.
That's not the idea.
It's that you have to enjoy the day-to-day work that you could be doing.
And maybe at the beginning, that's engineering.
Later it might be sales.
Later it might be design or whatever.
And you just have to remember in the back of your mind that you have to keep yourself
going.
It's a marathon.
You have to keep yourself going for a long time.
And so use all the tricks you can to make stuff interesting for you.
It's the best part about being a founder.
You have the freedom to keep things interesting and to change that whenever you want to.
That's great.
Aleem, thanks a ton for coming on the Andy Akers podcast and sharing your story and your
knowledge.
Thank you for having me.
Anytime.
Can you let listeners know where they can go to find out more about what you're up to
with Streak?
Yeah.
Just streak.com.
S-T-R-E-A-K. And for the founders listening, we built it for ourselves, for the founder
use case.
And so founders have to do a lot of stuff like sales, hiring, fundraising.
It's the perfect tool to do all that stuff in your email.
Super underrated to get a ton of leverage from a tool that could just make you move
so much faster, especially if you're like an early stage founder and you're trying not
to waste a bunch of time.
Right.
Or sign up for a bunch of things.
Yeah, exactly.
All right, Aleem.
Thanks again.
All right.
Thank you so much.
Listeners, if you enjoyed this episode and you want an easy way to support the podcast,
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Thank you so much for listening.
And as always, I will see you next time.