Omer (00:09.760)
Welcome to another episode of the SaaS Podcast.
I'm your host Omer Khan and this is the show where I interview proven founders and industry experts who share their stories, strategies and insights to help you build, launch and grow your SaaS business.
In this episode, I talk to Josh Ma, the co founder and CEO of Airplane, a SaaS platform for engineers to build internal tools.
In 2020, Josh and his co founder Ravi began exploring new startup ideas and they were most excited about building internal tools for developers.
However, after seeing how crowded that market was, the two of them began exploring other startup ideas.
But they struggled to find another idea that resonated with them.
Eventually, they realized that building internal tools was an area that both of them were most passionate about and where they already had strong founders founder market fit.
So despite the idea not looking all that promising on paper and being a very competitive space, they decided that this was the idea that they were going to work on.
The founders seemingly did everything right when they started out, including interviewing over 40 developers to better understand their frustrations and pains before they started writing any code.
And armed with those insights, they shipped the MVP version of Airplane and around four months later.
But acquiring those initial customers wasn't easy.
Their first attempts at targeting other tech startups fell flat and their outbound sales efforts didn't get traction either.
Through lots of persistence, experimentation and customer conversations, they kept refining their messaging and positioning and they began targeting and testing other markets.
Today, airplane is a 7 figure ARR SaaS business with hundreds of paying custom and the company has raised over $40 million in funding.
In this episode, you'll learn why the founders committed to the internal tools market despite the crowded competition and how they found a way to differentiate themselves.
We'll talk about how they were able to interview over 40 developers and why they had those conversations before writing a single line of code.
How Airplanes shipped their MVP in four months and and why Josh believes that they could have and should have shipped the MVP even sooner.
We also talk about why Josh thinks the playbook for selling to other startups doesn't work anymore, and how they discovered other market opportunities and why word of mouth was critical to Airplane's early growth.
And we dig into what it takes to build a great product that customers actually want to share.
So I hope you enjoy it.
All right, Josh, welcome to the show.
Josh Ma (02:54.690)
Thank you for having me.
Omer (02:56.290)
Do you have a quote?
Something that inspires or motivates you that you can share with us?
Josh Ma (03:00.370)
Yeah, I don't have a quote, but maybe just in terms of what motivates me.
I think that fundamentally software is just incredible force multiplier that humans.
It's the most incredible force multiplier that humans have ever invented.
And it's been a century in, and we're still in our early innings.
And so it's very real.
And Airplane is essentially our team's way of advancing a small slice of that.
Omer (03:25.660)
So tell us about Airplane.
What does the product do, who's it for, and what's the main problem you're helping to solve?
Josh Ma (03:30.700)
Yeah, so we say Airplane is a developer platform for building internal UIs and for workflow automation.
The thinking behind it is that half of the software in the world is internal tooling that's used by businesses.
Right.
So for every line of code behind your favorite website or favorite app, there's another line of code powering some internal automation, some internal dashboard used by engineering support operations.
These tools are on one hand massively important to the success of the business, but on the other hand, chronically under invested in because let's be honest, nobody wants to work on these tools.
Our goal is to make it faster to build better software tooling for these businesses.
So in terms of what we actually do on Airplane, you're typically a developer and you're writing the, the core pieces of code specific to your business.
So a way to handle suspending a user or provisioning a team or refunding an order.
And the Airplane platform takes the core pieces that you write and handles all the rest.
So assembling a UI around it, secure sign on, auditing, notifications, permissions, all the boring bits that you don't want to do, that we'll offer for you.
And you know, there's a lot of ways you can approach the problems that Airplane solves.
But I think there are three things that make us unique.
One is our focus on developers.
We basically think at the end of the day a developer is helping you build these tools, even if ideally it's more independent.
And so we're leaning into that and saying, let's make those developers lives easier.
Second, a lot of our competitors are focused more on UI building.
We're focused more on a task based approach.
Figure out the core task or operation that you want to do and let us deal with the ui.
And then third, we tend to allow a lot more advanced capabilities around deployment and infrastructure.
So our customers use Airplane to manage a thousand databases across 16 VPCs.
Right.
We operate this very complicated distributed agent runtime that you just don't see in too many other products.
Omer (05:30.000)
Got it.
Great.
Yeah.
So I Think the experience with Airplane, the user experience, is different to what I expected.
You talked about some of your competitors and I've looked at those tools and it's very much, you go in there and it's focused on the UI and the drag and drop widgets and so on.
And so I tried out Airplane and built and deployed the stripe dashboard template.
And it was very different in the sense that it felt more like I was in an IDE and there's like my source code files and, and I'm deploying code and stuff like that.
And I was like, okay, well, this is a completely different way to tackle this problem.
And it'll be interesting to talk about why you took that approach.
But before we dig into that, just give us a sense of where you are in terms of the size of the business, in terms of revenue, number of customers, size of team.
Josh Ma (06:30.650)
We found an airplane about two and a half years ago, early 2021.
We phrased 40 million over two rounds of funding and we have hundreds of paying customers and it's a small team right now of just 20 folks.
So I'm really proud of where we come from.
But definitely, I would say we're in the early innings of what the startup
Omer (06:49.610)
could be and revenue.
Where are you, ballpark wise?
Josh Ma (06:52.810)
I would say in the millions.
Omer (06:54.050)
Okay, so I want to talk about where this idea came from.
Before we do that, give us a little bit about your background.
What were you doing before you started Airplane?
Josh Ma (07:07.520)
Yeah, so previously before Airplane, I was CTO at a startup called Benchling.
And so Benchling was a pretty different space.
Although I like to joke that all these enterprise SaaS companies end up feeling the same under the hood.
But it was a Life Sciences SaaS company, so we built, or they built systems of record workflow, automation, design tools for scientists at biotech and pharma companies.
So CTO there, my role probably changed every nine months or so.
And so a whole bunch of different things.
Product development, architecture, working with customers, IT, security, and perhaps most related to Airplane.
Right.
I also grew, started and grew and ran the platform and infrastructure teams.
So it was very noble how much of the team's energy and time went towards maintaining tooling or helping with customer issues.
So we'd have a big go live at a pharma company the next day, but the user import tool was broken and that was like a sev one as serious as if like the main site was down.
Right.
Because we had some customer success manager who's going to go on site the next day and work with A team of like 200 scientists, and they needed to be able to get unblocked.
So coming from that background, we really appreciated when tooling was good.
You also really felt it when tooling was missing.
And so that definitely led to part of our early explorations that eventually led to airplane.
Omer (08:42.770)
Yeah, so let's talk about that.
How did you come up with the idea?
Josh Ma (08:45.730)
Yeah, so I wish I could say that it was just like, came to me in a vision, but really my co founder and I took a lot more of a exploratory route.
So he came from a product analytics SaaS background, I came from life sciences.
We just knew we wanted to work together and we just talked to a lot of people.
We would go through like an idea every like month, month and a half.
And so we started with like, let's maybe build benchling for finance teams.
Maybe let's build a way to collect all that data in one place and help a CFO make sense of it.
And, you know, there's a lot of comparisons to like, financial planning tools.
Or in the end it turned out that like, and this would be a pattern for future conversations too.
We just didn't fall in love with that Persona.
Don't get me wrong, I love finance people, I love accounting people.
It just wasn't someone that we got energy from really, when, like the dozens of conversations we had.
We also did a pass through life sciences quality assurance documentation tracking, which is like, I don't know, I actually found a pretty fun area that was like upstream of where benchling was.
But again, the problems that we saw, the Personas that we worked with just didn't, you know, as you went from conversation 10, conversation 20, you got more and more tired of it.
And so Ravi and I always took that to be like a sign that's like, okay, maybe this is in the field for us.
Right through this time.
We kept hearing, you would see on TechCrunch, oh, this database company launched, and our friend that we knew had started this build CI CD company.
And so you start every time that happened, be like, oh, that's really exciting.
We would talk about it and at the end we were like, you know what?
I hate the stereotype of Silicon Valley engineer going to build a tech company for developers.
But we just love solving those problems.
So we decided the last segment there was like, okay, let's maybe spend time talking to luckily all the engineers, engineering managers that we knew.
And we did.
We did like 40, 46 different calls.
We would just ask, what are you building for yourself?
That's one great property of engineers, right?
They can build for themselves.
What tools does your team use on a day in, day out basis?
What tools do you miss from your previous job that maybe was larger and you had built more infrastructure there?
And so we were just looking for patterns of what problems were being solved and what problems they shouldn't have had to solve.
And so that's sort of where the early days of a script runner came out.
It wasn't the most common thing, but it was most interesting to us.
It was like, actually there's this idea of just like needing to run stuff that was originally on your laptop and you would inevitably forget to close your database connection and you shut your laptop lid and you wake up to a page because your database is now out of.
Anyways, I'm getting too specific.
But enough of the people we talk to had some incident where some engineer YOLO'd something from their laptop and took down the company.
And at some point you're like, okay, let's not do that again.
Josh, maybe you should run your things on this machine.
Here's a little service to do it.
And depending on the ambition and time of the engineering team, you end up with a few different kinds of products.
But they all solve this core problem of taking scripts, database migrations, maintenance tasks, and trying to have centralized audit place to run them.
So Rob and I started unraveling that thread and we were very honest to ourselves, like, this might be a toy.
Let's just see where it goes, right?
And you start building it and you get it out there, people start using it, and eventually you're thinking, okay, this is actually the beginnings of a broader platform script.
Running the scripts is really like your compute pillar.
And it's like there's probably like a UI piece to this, There's a storage piece.
And so what we're really building is just business software infrastructure.
And we just come into it from the switch.
So anyways, that was the process we went through.
And at the end of the day, what we really kept coming back to was the idea probably is going to change.
I think people like to have these romanticized tellings of how these starters came to be.
And I think a lot of times they ignore the pivots and the slight adjustments along the way.
For us, the reason why we did this is it felt like we could spend 10 years just solving problems.
For engineers, engineers are this like, they're a little, you know, they like to complain and they have strong opinions about things, but they're these, like, they have these Superpowers, right.
And you know, for what I think most more people should learn how to code and become partial engineers.
But they have this crazy superpower of being able to take the building blocks that Airplane provides and just create these systems that are greater than the sum of its parts.
Right.
This synergistic sort of thing.
And that's just such an amazing feeling.
And so, yeah, that's why I'm in this field.
Omer (13:44.000)
I know you came up with this concept of idea filters to help you pick the right idea, and I think you've described that process very well.
But give us an overview of what idea filters meant to you and how you were trying to.
What were the different lenses you were looking at these ideas to try and figure out the right one.
Josh Ma (14:10.710)
I think the simplest thing was this yes or no of do I see myself spending 10 years on it?
Because like, people like to think of it as like a four year thing.
Well, like maybe IPO and then I'll be done.
But like, for a founder, that doesn't.
That story keeps going, right.
It's a 10 year, 15 year kind of journey.
And so I found that was the one question that just filtered out most things for me.
Right?
And it's like, can I imagine myself?
You know, it's 2033, am I still.
And I'm still working on this, Am I still excited?
And so that often was crystalline or concrete enough for me to say, no, that's not it.
Secondary was, when we're talking to people, did we get energy from the conversation?
Because it's really tied to that same idea.
But just imagine a day of sales calls and you're just on the phone with CFOs all day, or you're on the phone with engineers all day.
At the end of it, are you like, wow, that was great.
I met so many cool people, or are you like, thank goodness the day's over, let me go get dinner?
And so it really just came down to that.
There's nothing more specific about like TAM or like, you know, what's your specific power or advantage.
It was just like, do we like working on this?
Because really, like within the between the lines, there's all these like, other details of like, how you execute, how you hire, and how the market even changes.
And so it's really hard to like look at those this early on.
So it just came down to this very core emotional feeling.
Omer (15:37.650)
I mean, CFOs can be cool as well.
Josh Ma (15:40.250)
Sorry.
They're cool.
They're really cool.
I just think the problems that one was really the problems that I didn't find cool.
Omer (15:47.250)
Yeah, I get you.
I think it's like there's a certain type of conversation you have with a different type of person, and it's either something that draws you in, because the more you hear about it, the more you want to know about it, the more your brain is spinning with ideas on how you could solve it versus talking to somebody where you get the problem you can solve.
It just isn't that.
That energy just isn't there to just naturally kind of keep this thing going day in, day out.
Josh Ma (16:18.660)
Yeah, I think the more like, the more.
What's it called, by the book word for this would be like founder market fit.
Right.
It's like I'm using this as a litmus test for it because really what's happening is I'm hearing about your problems, I know about my skills and my experience, and do I get excited about applying my background to these problems?
Right.
So a lot of the, like, the most on fire CFO problems were at the time that the people I talked to was like getting your team to like enter in their data correctly or like, it was a lot of human and people problems.
It wasn't like, oh, I have a big data problem around and I don't have the infrastructure for it.
Right.
So this is the nuance there is.
It's really just how the, the founder connects to those conversations.
Omer (17:01.120)
I want to talk a little bit about.
You said you went out and talked to engineering folks that you knew.
I talked to a lot of early stage founders who are reluctant to have those conversations because they feel like I haven't figured out what I'm solving or my solution or I don't have an MVP or something like that.
And really, at this point, it's really more about.
No one cares about your.
Your idea.
Josh Ma (17:31.850)
Right.
Omer (17:32.170)
They want to talk about their problems, and I think that's what you were doing.
But just help us understand, like, how are you framing these conversations that got, you know, 40, 50 people saying, yeah, I'll give you time to, to chat more about it.
Josh Ma (17:45.210)
I mean, people like to talk about their problems.
I think people like to like, be heard and if you're respectful about their time and you're actually listening, I think, like, I don't know, I'm also very privileged to have worked with a lot of engineers and gotten to know a lot of folks in the industry.
So there's definitely parts of both.
But yeah, it's like, it's like you're saying, right?
Like, it's the goal is not to talk about me or what I'm building.
Like we didn't sell anything in most of those calls.
Maybe towards the end we started pitching the idea.
It's really just about deeply understanding what are the on fire problems that the people you're working with are going through.
And so that's always, you know, we start the conversation like, what's bothering you right now?
Right, like what, what did you guys, what was in your last Sprint Retro and what, like what were the main issues?
Like why did you miss your last deliverable or what tool just saved you right this last like week?
So just talking about problems and either solved or unsolved, I think often led to like pretty interesting places.
And some of it was just to challenge the assumptions that we had because we all had engineering backgrounds too.
So yeah, there was nothing more special than that.
At some point you have a set of questions like, okay, this script running is interesting.
Let me maybe ask more about when the last time you did database migration was or what the last few incidents were.
So you start getting a sense for that.
You evolve your question set over time.
But yeah, it's nothing.
It's not rocket science.
You just add in the time.
Omer (19:08.410)
I know this space of building internal tools is becoming quite a crowded space and I'm not sure if it was that different back in 2021.
So how much of that was a factor for you?
Did it hold you back from committing to this idea?
And how did you get over that?
Josh Ma (19:33.280)
The short answer is no, because I actually like to tell our team candidates, just folks, this space is actually the oldest space, like the first databases invented or like when Oracle came out of the database in like 1978.
The first software built on it was like order management, hr, data management.
And the original enterprise software was internal tools.
And so in that lens we're coming in this lineage of some legacy, some not enterprise software building.
And then within that we were not trying to do internal tools at all.
We just wanted to let your scripts run, right.
And then this internal tools like buzzword came along and we figured that if the market was going there, let's at least match that and so people could identify more quickly what we were selling.
But it's interesting because I feel like we live in this bubble of tech and VC and if you talk to software shop in the Midwest, they have no idea.
Like this term doesn't exist in their vocabulary, right?
Like they don't think about this way, they just think about the software that they've built and, and so A lot of times the world's big and these companies have never heard of us.
They haven't heard of our competitors.
And at the end day, we're just trying to convince them that Airplane buying airplane is better than building themselves.
So a lot of times it's a build versus Buy.
So, coming to the original question, right, like, that's competition.
It comes and goes so dynamically.
Right.
That it doesn't really, you know, if you talk to all the, like, productivity software companies, right, like the asanas, the Monday, or if you look at, like, product analytics, some of the most competitive spaces, I bet the early days.
And I know for some of those, the early days, like, they never saw each other, right?
And so it's because the world is so big that, like, it really depends on both how many competitors there are and how big the space is.
So I just think it's really dangerous to make decisions based off of competition.
Omer (21:34.150)
So you said that the biggest decision or obstacle you had to overcome was build versus buy selling to developers.
Kind of feels like the build choice is the natural way to go.
How much of a struggle was that for you?
Josh Ma (21:55.830)
It's mixed, I think.
So.
For example, there's some companies I've talked to where you're spending a million dollars a year in salary on internal tool development.
Great.
You're ahead of the curve and you have engineers who are invested.
Right.
I still think Airplane solves a certain set of problems better than if you were to do it yourself.
But from a pure ROI perspective, it's potentially not clear if you're already investing that much.
You might as well just put that onto the teamstoremap.
Luckily for us, I think, and I mean this in the most charitable way possible, people don't like to build what Airplane is building.
Right?
Like, we're doing all the boring bits.
We're doing SSO and audit trails and groups and notifications and like a slack integration.
And like, don't get me wrong, for Airplane, it's really fun because we get to think about this at scale, but for our customers, it's the last thing this product engineer wants to do, right?
And so there's that, like, arbitrage of interest that comes in.
So compared to, like, I think some of the other dev tools we're seeing, it's definitely harder because in those cases there's no, like, not necessarily always an established budget or, you know, there's no, like, RFP that goes out for this specific kind of product.
But it's an easier pitch when you say, okay, you could Build this yourself.
But do you really want to?
Omer (23:12.240)
Okay, so you eventually commit to this idea.
How long did it take you to build or ship the first sellable version of the product?
And how long did it take you to get the infamous first 10 customers?
Josh Ma (23:32.970)
So we started working on this December 28th of 2020.
So essentially right before the new year.
And we opened in public beta in April and so it took us four months to get there.
And then we started charging for the thing in July.
And through my learning all this, I really just think we could have shipped even faster and we would have learned even faster and we would have gotten to our first 10 customers even faster.
Because what we did was at first you had this like I came from benchling, very enterprise heavy, right?
Very pilot and state of state sow statement of work heavy, right?
Like a lot of the work he did was like one big customer and you really understood their needs and you deliver for them.
For airplane horizontal tool, dev tool, we tried doing that and there were a lot of misses on like, oh, big company X is interested, let's do a call.
And then sort of fizzling out.
And so really we should have, in hindsight, just launched the damn thing.
Because you just get customers coming out of the woodwork, right?
Like our early customers, like they weren't big contracts, maybe a few hundred dollars a month, but like they were in South America, they were in the Philippines, they were in the Midwest, somewhere in Silicon Valley.
And so you just getting yourself out there, especially for a horizontal product, which is a lot more valuable in terms of finding those customers, but also learning from those customers.
So I would have done it way faster, way earlier and way more iteratively.
Omer (25:02.600)
You said you started charging in July.
How long did it take you to get the first 10?
Did they just switch when you turned on billing?
Josh Ma (25:14.120)
It wasn't glamorous.
It was like in the first week, maybe one or two, the third week, a few self served on.
So maybe in the first three weeks is how we got our first 10.
But it's because it was a mixture of someone put down their credit card for $50 a month, right?
So it was definitely a trickle.
It's not like just open the floodgates.
Omer (25:35.110)
So once you ship this, you just said here's the beta version of the product or something and it's free for now.
We're going to start charging at some point so that expectation is set and then at least you had people using it for us.
Josh Ma (25:48.710)
Charging was really just like, I'm just curious to make sure that they're not just using this for free.
Compute.
Right.
And so we wanted to just.
Just.
No, do.
I think it was like a critical business decision.
I don't think so.
Right.
Because I think we were always selling B2B, so it was really just like a, let's just test this just to make sure, but also to actually look more reputable.
Right.
So you're connecting this to your production database.
You don't want something that's in beta, necessarily.
And so we were like, let's just make this look like a real product and let's just start charging.
Omer (26:22.820)
So.
Josh Ma (26:23.190)
So it was more of that thinking.
Omer (26:25.590)
Okay.
You said in hindsight you feel like you could have shipped the MVP sooner.
Josh Ma (26:31.350)
Yeah.
Omer (26:31.910)
Was that like just building it faster or are you saying we could have stripped it down and focused on one or two specific things better or we tried to do too much with the mvp?
How do you think you could have done that differently?
Josh Ma (26:46.470)
No, I mean, definitely not.
Like, I think every manager's like, dream that it's like, oh, we could just simply done it faster.
It's really more about scoping.
Right.
I think we went a little further on some bells and whistles and like, we.
We should have just still done it anyways.
But the difference is in that time, while we're building the future things, you could have gotten people using it, gotten feedback on the earlier things.
And so it's more about scoping and when you allow access versus.
And so I think there's some things where we just sat on too long.
We were like, it'd be really great if you could do this too.
And it's like, well, does that prove your core hypothesis of this being a useful tool?
Maybe not.
And so it's very hard.
It's only easy to say in hindsight because at the time you're like, oh, I get it.
I'm supposed to be very minimal my scope, but I think this is going to be a key blocker for A, B and C. So I'm definitely saying this with hindsight bias, but I.
It's still true.
Right.
We should have shipped it earlier.
Omer (27:44.680)
Had you raised any money at that point, or we had.
Josh Ma (27:48.120)
We're a weird company.
I'll say.
Like, we've had the privilege of knowing the folks at Benchmark through our exploration.
Ravi and I were both entrepreneurs in Residents there.
And so we raised our first round right out of the gate.
Right.
And so it sets you off on a different path.
Right.
You know, you're raising it.
You feel like you can hire people faster.
Right.
So we hire our first two engineers in like the first month.
And so you end up like building a little team before you start building, building the whole product.
So yeah, we, we had raised pretty early on.
Omer (28:27.530)
Let's, let's talk about what else you've done to acquire customers.
When you and I were talking about this earlier, you said, you know, word of mouth was one of the most, kind of like it was kind of like the most important thing.
Let's talk a little bit about that.
Like why do you think what does that mean to you and how do you get word of mouth about, you know, your product?
Josh Ma (28:56.340)
Yeah, I think it's because it's like you often think about the go to market of your product and you start thinking like if only we just made this part good, we'll just be able to sell it.
And it's sort of that at the end of the day if you're on engineering or product design, you're just build a good product first.
Right.
Solve your customer's problems.
And they might not just come, but it is actually, I think step one.
And so it is a bit of a circular affair because as you get more customers you start understanding their problems better and leads to like the next customer.
And so there is like an iteration here, but having good core product means that someone who is at a startup that maybe adopts your thing, talk to their friend who works at a bank and says hey, you should check out airplane, they're really cool.
And so this word of mouth is, you know, I'm saying very obvious things but it's just easier to like say than to actually once you feel it and understand it more.
And it's also really hard to measure and understand.
Right.
Um, but at the core like just don't forget that you need to build a good product and solve customers problems.
Cause then the subsequent things you layer on get much easier.
The analogy is like if you have a funnel and you're trying to really like put as much water as you can the top of it, but just leaking at the bottom.
Right.
It's just, you're just wasting your effort.
So definitely get the core product right.
Build a great experience, deliver value, very basic things, but you really have to do that before you start figuring out how to sell it.
Omer (30:28.860)
So part of this comes from the 40 something interviews you did with developers.
Before you sort of figured out what you were going to go and build.
What did you do beyond that?
Were you doing anything to regularly collect feedback or as you iterate to make sure you're Building the right thing.
Were you having conversations or were you kind of more looking at how people were using the product or a combination of both?
Like, how did that clarity keep coming in terms of we're getting.
Every time, every week, we get super clear about.
More clear about the problem the customers have and that we're building a better product.
Josh Ma (31:09.750)
The first thing I'll say is, like, once you did that early research, you sort of had to throw it all out, meaning, like, now you have a real product, you have real customers.
Like, that got you to your initial hypothesis, but now you're really looking at the new data that's coming in and you should be thinking about that because, like, customer feedback is going to, like, trump what someone told you on a zoom call, like a year ago, right.
And so we quickly, like, discarded those and started looking at, like, the actual usage we were getting.
I will say, like, this is really hard.
I don't think we, like, did a fantastic job of this.
It's just always.
There's always a bit of a cloud of war, fog of war here, Right.
Like, a lot of times you did have to just rely on your gut instinct on like, reading between the lines of this feedback here and this lack of interest here and this, like, happy usage here.
As a founder, this is like where I think we need to go.
And a lot of times I think I wished I had, like, learned faster or you pushed even harder on it.
But, you know, to answer the question, it is just a lot of just talking to customers, right?
Either in sales calls, pitching them, or getting feedback.
Right.
Even today, like, I meet at least sometimes monthly, sometimes quarterly with like the top 25% of our customers at least.
Right.
And so it's just really important to talk a lot with your customers to really understand them and just understand the problems you're solving.
Omer (32:37.130)
So.
Josh Ma (32:37.530)
So there's no silver bullet for that.
But yeah, just keep iterating.
Omer (32:42.090)
So content marketing is another area that's helped you to acquire customers.
What exactly have you done there so far?
Josh Ma (32:50.250)
We thought about it in two various ways.
One, we called it thought leadership.
Internally, this is when a lot of the audience that we were selling to were like startups.
Right.
And so my co founder and I would write blog posts about our experiences.
And the second category is more around developer tools and certain problems that we saw engineers facing that were potentially adjacent to our space.
And at the end of the day, it's like, there's a lot you can read on the Internet about content marketing, so I'm not going to repeat that here.
But you figure out what problems your customers or your potential customers are facing and you try to get to them.
Right?
You try to give them that information.
It builds awareness, it lets people find you when their intent is more accurate.
Right.
As opposed to like trying to do a lot of manual reach outs.
This is especially true for, I think, you know, horizontal productivity or horizontal dev tools where timing is really important and so you can look at a company that looks exactly like what you would sell into.
But I don't know, maybe they haven't started hiring out their support team or they have and they already like figure out some hack to do things or you know, they're, there's some churn in the leadership and they're not really thinking about building this, buying this platform right now.
So it's very hard to get timing right.
And so instead you really just want to get yourself out there and let people click when they fit you.
Omer (34:11.280)
So in terms of ideas of what to write about, if you're talking to customers about their problems, you probably have a long list of ideas that you can potentially be writing about.
Were you doing anything else in terms of SEO or were you just like, we're just going to publish high quality content and hope it starts ranking because we're talking about specific enough problems or something, or long tail keywords?
Josh Ma (34:37.930)
There is a level of technical SEO skill that you have to build up as you do this.
So no, it's not as simple as just write good content.
They'll come.
We use AHREFS a lot.
It's a good tool for, for understanding keywords and how you're performing.
You have to do a bit of research on which keywords are highly contested and you want to make sure you SEO, optimize your content.
I can't say I'm an expert on it.
I definitely learned a lot about it in the last few years.
But yeah, you have to put in the time and get that right.
Omer (35:12.980)
If I understood this correctly, you were, I guess focusing a lot on like top of funnel type problems and you said problems that were adjacent to what you're solving.
In terms of it wasn't, you know, every piece of content wasn't.
This is a problem that you're trying to solve.
This is how Airplane solves it for you.
But it was more about, maybe you do have content like that too.
But a lot of the other content was like, okay, you got this problem in terms of building an internal tool.
Here's some of our thoughts on how you could be solving this problem.
Doesn't necessarily translate to using airplane this afternoon, but hopefully you've now got some awareness of who we are and what the product does.
Josh Ma (35:59.790)
Yeah, it's just both is how we approached it.
Right.
Ideally they would all be high intent, directly related kind of problems.
And I think we, we can and shouldn't invest more there.
But at some point you're like, also, let's also add in things that are lower intent, but that'll build some more visibility and awareness and maybe it's easier to get traffic on those.
Right.
So I think you have to experiment.
It depends on your business and depends on who you're selling to.
Omer (36:24.380)
Right.
Josh Ma (36:24.700)
You know, if you're like an ATS or like doing hiring, it's a lot easier to just target direct like hiring problems.
So yeah, you have to experiment, figure out what's right for you.
Omer (36:34.620)
Nearly every founder I talk to, when I say, well what did you try in terms of growth that didn't work.
They always say ads.
Right.
I don't know, I can understand why, but that was one of the channels that has worked for you.
So where were you spending your ad dollars?
Josh Ma (36:54.810)
I will say it has worked in a binary degree.
It is not working in a. I think it could be better in a sense.
Right.
Like the beauty of Google's business is you can spend as much as you want on them and they'll figure out how to like show your ads.
Right.
And then you, you'll measure the clicks, you'll try to attribute it and you'll try to figure out, you know, was this worth it for us, I think it got more complicated because all we had to do is we'll close.
Like our ACV is like 20k.
Right.
And so if we could spend 20k a month, if every month that got us one deal out of ads, it was like break even.
And so you could spend 50k and get 3 deals out of it and still be unsure if it was like worth it.
Right.
And so for us it's a very like very broad, fuzzy zone.
I will say it did get our first like five largest customers in the door.
And so it is, but it is also not, you know, you can't mistake that for product market fit is what I'll caution.
Right.
Like it's just not a very.
You can't double that to 100k and just get double the number of deals.
So it's very valuable way of getting those customers and learning from them.
But I'm not happy with that as like, you know, our go to market
Omer (38:05.060)
per se and just because you could spend 20k to acquire a customer doesn't necessarily mean you should be spending 20k to acquire them.
Josh Ma (38:15.220)
You could spend half of that, get a high ranking blog post that just pays off almost indefinitely.
Right.
So there's definitely higher ROI ways to do it, but there's some low hanging fruit there.
Omer (38:26.560)
At the same time, you mentioned something about outreach and one of the areas that didn't work in terms of growth was sending cold emails.
What did you try there?
And sort of looking back at what you've done so far, why do you think that hasn't worked for you?
Josh Ma (38:46.120)
I wish I knew why it didn't work because then we would probably get it to work.
I think the short of it's like my understanding is this is something you have to really experiment with and at some point it'll click.
For some industries it doesn't work, for some it does.
Right.
And it's tempting because like you talk to a few peers where they're like, yeah, the first like 10 million I got was all like 90% outbound.
And you're like, oh man, like, maybe that should work for us.
But you know, someone once told me, like, Josh, you're going to say, let's do outbound.
You're going to try for a month and it's not going to work.
And you're going to decide like, oh, outbound, isn't it?
But really it's like the thing you tried the Persona, you're trying the message, you're trying the way you're like, I don't know, the way you're phrasing in your emails just wasn't it.
But it's like very hard to tell what parts of that didn't work.
Right.
And so I know that it's not working, I know that it might work.
And I think it's going to take a bunch of experimentation to see how we can get there.
So it's very frustrating.
It's a bit of a black box.
Right.
But so I think of it as something we're going to just keep experimenting on.
Omer (39:49.220)
Yeah, it's such a, you know, I tend to roll my eyes when I, you know, you see stuff online or on YouTube where somebody says, you know, how we built this business and you know, sent out cold emails and whatever.
And the reality is just like any other growth channel, it's not straightforward.
There's so many different, as you said, like, so many factors involved in getting that working that it does take a lot of experimentation.
And I think it's also very easy to get disheartened.
When you're sending out these emails, you're excited about your product and the only replies you're getting are don't email me again or how did you get my email address?
Right?
Josh Ma (40:35.110)
That's at least better than apathy, right?
Omer (40:37.270)
Yeah, true.
Well, let's talk about the.
In terms of who you were selling to initially and where you ended up getting better results.
So initially you started out like, it's like, hey, we're going to go and sell this to other tech companies and startups.
Josh Ma (40:55.400)
Right?
Every startup, right.
Especially because we came from other startups.
You're like, well, I would love for my peers to use us.
There's the sense of validation, sense of great logos.
Right.
And it's a very, you know, 2018-2021 kind of mentality.
Right.
Because then this startup raises the next round of financing.
10x is their team size.
Your ACV just went up by 10x.
And so it's a bit of a circular kind of motion there.
And in 2022, that's just 2023, that just isn't happening.
Right.
Like I just last year I spent 6 months negotiation negotiating a 30k contract and that just never happened back in the day.
Right.
And so a lot of founders are finding, you know, we're in a very different era than we were in the last decade.
And so what we found was working and very much stumbled into this is like the world's massive.
Right?
And there, there's these like non tech companies or there's even tech companies that are based out of the Midwest, based out of, you know, Canada, there's like small shops internationally, there's the whole rest of the world really.
And their businesses are not as affected as, you know, the Silicon Valley tech companies.
And so we've, it essentially looks like going up market, going to a bit of a older segment of the market, but turns out they have internal tooling problems.
Right.
And so I will say we're still learning really how to sell to that, but we found good success there.
I'm not saying we won't ever sell to startups, right?
Definitely.
Well, we still have a startup plan, have a free tier, but it's just a timing perspective.
The tech startup market is not the best to be selling to.
Omer (42:38.210)
So that strikes me as a bit of a problem.
What you just said makes sense, but you've got a horizontal product which as we chatted about is difficult to figure out the messaging for anyway.
Now hasn't it become exponentially harder because you're Going after all kinds of companies in all kinds of verticals with a horizontal product.
Josh Ma (43:08.619)
It is a very fair point.
I should have been clear.
We're going after specific verticals in these other parts of the world, right?
Specifically for airplane.
I think if you look at financial services and healthcare, health tech, fintech, those have been especially good for us.
And so the motion goes less from selling a platform to selling a solution, right?
You're selling an answer to a series of problems that the engineering team has, that the support teams have, that the operations team has, and you have to understand how that fits in those verticals.
So it is, it's not.
We do one vertical.
Maybe we're.
We focus on three at a time.
But no, you're absolutely right.
It can't just be like anyone that's not in Silicon Valley.
It's like specific targeted verticals outside of there.
Omer (43:54.950)
How did you figure out which verticals to pick?
I mean, that.
I think I've seen so many founders struggle with that because you got to first of all figure out what's the vertical, what's the messaging for this vertical, how do we reach those people?
Is our go to market working, or is this just the wrong vertical and we should move on and focus our energy elsewhere?
So how did you pick?
And again, were there any lessons you learned from that in terms of maybe how not to pick a vertical market?
Josh Ma (44:31.770)
The answer is you had to spend time and think and iterate, right?
So it's a sheer combination of sheer luck and having hypotheses at the same time and then just learning, right?
So we did have a hypothesis, like, I think especially if you looked at the early conversations, like fintech, right?
Had a lot of regulation, humans in the loop, healthcare, like anywhere that things can go wrong, but also their sensitive processing.
So these are probably good guesses, right?
But then also, like, I don't know, one of our largest customers came in from a Google Ad and we were even targeting them, that kind of industry.
And so sheer luck, which is like partly why you just got to get yourself out there.
So it's really finding those initial conversations and then pulling on the thread, right?
Really asking why this company, why this space, what's special about that?
And then refining your messaging, testing it, seeing if it works, trying again.
So it really is just a lot of iteration.
Omer (45:22.850)
Okay, so if Outbound wasn't working, how were you reaching these people?
So let's say you decide, you go through.
And you said, okay, fintech sounds like a great vertical for us to at least try and validate or invalidate our hypotheses that there's an opportunity there.
But then how are you reaching these people?
Josh Ma (45:40.560)
You really try like a bunch of channels, right?
So we would go through investors, go through network, we would do messaging on LinkedIn, we would, you know, our head of sales had previous connections that he brought in.
And so network definitely try that.
A lot of it was just, you know, SEO SEM, people coming inbound.
And so you would once in a while, once a week, get something from like company that you've never had connections to.
Other times it's word of mouth, right?
People moving companies or talking to their friends.
So it's really, you do everything and anything and you just gotta like, you gotta just spend the time.
Sorry, all my answers come back to that.
But it's just so.
Because like you even ask customers where they heard of you, right?
And they'll say, oh, I don't know, maybe Hacker News.
And I'm like, we haven't been on Hacker News for a few months now.
And it's like, definitely that's not the answer, but they just don't remember.
And so although I will say product launches are also a good way to do it, right?
Make a big splash about what you're doing, get on Product hunt, get on Hacker News, get on Twitter.
But again, just doing a lot of everything because it's all over the board.
Omer (46:43.630)
Yeah, I think the attribution problem is really hard if you're doing a lot of things at the same time.
Because even if you're able to put some kind of, you know, tracking link or whatever to figure out the source, maybe it wasn't that.
Maybe that was the third touch point that persuaded somebody to come and sign up.
And maybe there was two or three other things that you'd done before that got their attention in the first place and got them interested in the product, even though they didn't take action at the time.
And so who gets the credit for it, right?
I don't know.
Josh Ma (47:23.020)
I think it's always going to be hard, right?
Because I've talked to marketing leaders and go to market leaders at like various sizes.
I don't think it's ever solved.
I don't know, maybe some people like have it like down to fine.
But like you can experiment, right?
And you can, I think you can often tell like if you start a new campaign and starting to like get more people in or you do an in person event and like those like, like.
So I think on the margins you can sort of feel it, but it's noisy for sure.
Omer (47:49.000)
One other thing we talked about sort of the build versus buy sort of obstacle you have to overcome.
Just going back to what I said earlier in terms of how when I went into Airplane, how the experience was so different to what I've seen with some of these other products.
Was that a very intentional thing that you did?
Terms of we're going to make this feel like an IDE where you have control over your source code and it's not like UI heavy, a no code product where you can add a little bit of code in the back.
It just seems like quite a contrast.
I'm just curious why you designed it that way.
And especially talking about building a great product and understanding customer problems.
I assume there's a reason behind that.
Josh Ma (48:41.260)
Absolutely.
I mean that part has been very intentional.
Right.
Part of Airplane is like recognizing that a lot of internal tools are in the critical path and engineers want to manage those tools like they would production systems.
Right.
They want to build them faster.
For sure.
There's a different kind of SLA in some regard, but like a lot of we want to meet developers where they are in terms of their workflow.
And so while it's different from our competitors, it's actually very similar to the rest of our developers lives.
Omer (49:10.820)
Right.
Josh Ma (49:11.140)
And so they can use GitHub, they can use code review, like some of them add unit testing.
Right.
And so that's totally intentional because that's the ICP of who we serve.
And so those are the lives that.
Those are the Personas whose lives we want to make better.
Omer (49:26.420)
Okay, let's wrap up and get onto the Lightning round.
So I've got seven quick fire questions for you.
Just try to answer them as quickly as you can.
You ready?
Josh Ma (49:32.860)
Yes, sir.
Omer (49:33.620)
What's one of the best pieces of business advice you've received?
Josh Ma (49:36.830)
The Internet is huge.
I've said it a few times, but it really is.
You think it's big, but then 10 exit, 100 exit and so the world's a really big place.
Omer (49:46.270)
What book would you recommend to our audience and why?
Josh Ma (49:48.830)
I really loved this is really nerdy about tech history, but it's called Software.
So Software without the E. It's a book about Larry Ellison in the early days of Oracle.
It's really fun because it's written by this journalist, but he let Larry Ellison write in the footnotes and so there's a bit of a dialogue and back and forth and so it's a great book.
Omer (50:10.450)
I haven't heard of that.
Let's check it out.
What's one attribute or characteristic in your mind of a successful founder.
Josh Ma (50:16.450)
I think the good founders take their team with them on the journey, so you have to have your own direction of where you want to go and stuff.
You have to bring the team with you.
Omer (50:25.490)
What's your favorite personal productivity tool or habit?
Josh Ma (50:28.820)
Yeah, I've been trying to just do at least one thing each day.
It's a very classic thing that I've been told in the past as well.
But what's your most important thing?
Write it down and get it done.
Omer (50:40.660)
What's a new or crazy business idea you'd love to pursue if you had the extra time?
Josh Ma (50:44.180)
I don't know if I'd pursue this, but I find the small software utilities you find on the Internet just really fascinating.
You try to do an HTML PDF converter and you see that someone's SEO optimized that to the top and they're probably making some decent ad volume revenue from it.
Right.
I'm sure it's really competitive, but it's just such an interesting corner of the Internet that you stumble into.
Omer (51:05.890)
I love playing with tools like that.
What's an interesting or fun fact about you that most people don't know?
Josh Ma (51:11.570)
I'm colorblind and it's not that rare, but often doesn't come up conversation until we're arguing over a mock and you realize, hey, this guy can't see the colors properly.
Omer (51:21.170)
Wow.
And finally, what's one of your most important passions outside of your work?
Josh Ma (51:25.270)
Yeah, it's corny, but it's true.
I have a nine month old baby boy and so it's been fantastic just going between like startup land and then, you know, hanging out with them.
And so it really just grounds you.
It's great.
Omer (51:38.710)
Definitely.
Yeah.
That's awesome.
Great.
Well, Josh, thank you so much for joining me.
It's been a pleasure kind of talking through the story and extracting some of the lessons that you've learned along the way.
If people want to check out Airplane, they can go to airplane.dev and if folks want to get in touch with you, what's the best way for them to do that?
Josh Ma (51:57.820)
I'm just joshirplane.dev.
so shoot me a note.
Love to chat.
Omer (52:02.700)
Thanks for joining me and I wish you and the team the best of success.
Josh Ma (52:05.820)
Thank you, Omer.
Omer (52:06.860)
Cheers.
