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 talked to Jeff Roberts, the co founder of Outseta all in one membership software that makes it easier to build SaaS products, membership sites and online communities.
In 2016, Jeff and his two co founders set out to build Outsetter.
After experiencing firsthand the pains of cobbling together different tools to run their business, they decided to build an all in one solution to simplify things for developers.
But progress was slow.
It took them two years to build their mvp and then they quickly discovered that selling the product was going to be a lot tougher than they had expected.
Most developers they talked to just wanted to build their own tech stack.
The founders struggled for almost a year trying to get traction, but during that time they also kept listening to customer feedback and improving the product.
As the product became easier to use, they started to get the attention of no code founders who were building products on platforms like webflow.
That's when they realized their all in one software was more valuable to these less technical folks and that they'd been focusing on the wrong target customer.
So they doubled down on their new ideal customer profile and finally started getting traction.
An interesting side note, today their customer base is split roughly evenly between no code founders and developers.
Although they struggled to sell to developers in the early days, things changed as the product kept improving.
It's a great story of perseverance and the importance of continuously improving your product.
In this episode, you're going to learn how the founders pivoted from developers as their target market to no code founders who were building products on webflow.
We talk about the role of content marketing in driving growth and how the team takes an unconventional approach to the content they create.
We also talk about how the founders built successful partnerships with Stripe and webflow, which have both helped to drive new leads and customers.
And we talk about the benefits of the company's self managed business model and a unique compensation structure they have that's helping them to attract a lot of talent.
So I hope you enjoy it.
All right, Jeff, welcome to the show.
Geoff Roberts (02:30.800)
Thanks for having me.
Omer (02:31.560)
Omer, great to talk again.
We haven't spoken for a while, but I've known you for several years now, so I'm glad we're finally getting to sit down and have this conversation and talk about Outseta on the podcast.
So thanks for joining Me.
Geoff Roberts (02:45.230)
Yeah, likewise.
It's been several years and a lot has happened with SaaS Club.
A lot has happened with Outseta.
So, excited to catch up.
Omer (02:52.190)
Do you have a favorite quote, something that inspires or motivates you that you can share with us?
Geoff Roberts (02:55.630)
Yeah, I don't have a quote, but when you sent over this prompt prior to this, I was thinking about, like, what is important to me.
And at the end of the day, I think most people in tech are excited about building some sort of new and innovative technology, and that's what gets them out of bed every day.
That's actually not the case for me.
The case for me is very much looking inwards at the company that is Outseta.
We want to run a small, independent business, and my motivation is to build a workplace for a small number of people that really allows them to live the best life possible.
And it sounds kind of cheesy, but I started my career at a company that truly treated me extraordinarily well.
And looking at my own behaviors, every time they sort of prioritized me over what I could do for the business, I just became more fiercely loyal to that company and worked even harder for them.
And I want to have that same sort of influence on the people that work at Outseta.
Omer (03:52.430)
Love it.
So for people who aren't familiar with Outseta, can you just tell us what does the product do, who's it for, and what's the main problem you're helping to solve?
Geoff Roberts (04:00.890)
Yeah, it's an all in one tech stack for anybody building really any sort of subscription business.
So our customers are either building SaaS products or membership sites, or charging for access to an online community on a subscription basis.
Those sorts of businesses, and a lot of people will refer to Outseta as the Shopify of SaaS, meaning it's basically a platform that makes it very, very quick and easy to stand up.
A subscription business.
Omer (04:25.690)
Cool.
So before we get into how you came up with the idea for this business, so let's talk about what you were doing before you started outseta.
Sure.
Geoff Roberts (04:37.200)
So I actually went to school to be a writing major and thought I was gonna work for a newspaper or magazine, something like that.
I got out of school in 2008, right as the economy was plummeting and frankly, didn't know what to do.
So I went to grad school, got a business degree, and ended up making my way into the tech scene in Boston, literally.
Long story short, I never had any particular interest in working for a software company.
If I'm honest, it sounded pretty Boring to me at the time, but I got a job working for a tech company called Buildium in Boston, and unbeknownst to me, I just sort of walked into a great situation.
I was one of the first five or 10 employees at the company.
Pretty much everybody else was a developer at that point.
And they said, hey, Jeff, go sit in the corner and figure out how to market this thing.
Unbeknownst to me, they had sort of just found product market fit.
They were in an underserved market and I was given a ton of freedom to figure out how to grow a startup and how to grow a SaaS business.
Fell in love with startups in the process and have been building SaaS companies ever since.
Omer (05:41.260)
Now, you joined very early on and then you left, I think about five years.
How big was the business when you left?
Geoff Roberts (05:49.580)
When I left, the business was doing about $20 million in revenue.
We'd grown to about 15,000 customers.
So it was a pretty cool experience to go from really a startup to about $20 million in revenue over five years.
Omer (06:04.860)
And then several years later after that, you woke up one day and you heard that Buildium had been acquired.
Geoff Roberts (06:11.500)
I did.
Omer (06:12.220)
For how much?
Geoff Roberts (06:13.180)
$580 million.
Omer (06:15.580)
That's a nice chunk of change.
Geoff Roberts (06:16.940)
It sure is, yeah.
Omer (06:18.460)
And did you have equity in the business?
Geoff Roberts (06:20.530)
I did, I had equity, although I'm not as wealthy as you might expect.
It was my first job out of college and I like to think that I did a good job and helped the company grow, but I was also issued equity, as you would issue to somebody that's in their first job out of college.
Omer (06:37.730)
So let's talk about Outsetter.
Where did the idea come from?
Geoff Roberts (06:43.250)
So it actually came from our experience at Buildium.
So at Buildium, in the early days, I was very much like the business user within the company.
And then my now co founder at Outseta, his name is Dmitry, he also co founded Buildium and he was the CTO of that business.
And I found myself going to him as we were scaling, pulling on his shirt sleeves, so to speak, and saying, you know, we need to integrate Stripe for billing, we need Salesforce for a CRM, we need Zendesk for support, we need HubSpot for marketing automation.
And very, very quickly, our needs as a blossoming business in terms of the software tools we need were growing.
And Dimitri was looking at all these different tools and trying to figure out how to integrate them.
So we had a really tightly integrated tech stack.
And at one point he just kind of threw his hands up and he Said, you know what, I'm the CTO of this company, I'm supposed to be building our software, not spending 25% of my time building out this tech stack.
And being something of a stubborn guy and an engineer himself, he ended up building a very basic homegrown tech stack.
A really simple support ticketing system, a really simple subscription billing system, et cetera, et cetera that we used until the company was at 6 or $7 million in revenue.
And at that point there was more complexity in the business.
We did go out and buy all those best in class third party tools.
But as we reflected on our experience, we said, you, you know what, that really simple tech stack that we used in the early years worked great for us.
There's a lot of other founders in the exact same situation that are cobbling together all these tools.
It's taking their time away from product.
Why hasn't somebody built this Shopify for SaaS?
Why hasn't somebody just taken the core tools, kind of distilled them to their most important features and just delivered a platform to help you launch a SaaS business quickly?
So that's sort of scratching our own itch and very much where the idea for Outset it came from.
Omer (08:40.839)
Okay, so how did you guys get get started?
So this was how much after the, the Buildium acquisition was this that you guys decided to get together and start this business?
Geoff Roberts (08:53.719)
So we actually, the Buildium acquisition was in 2019.
We actually started working on Outset at the end of 2016.
So I had, I had left Buildium prior and then my co founder Dmitri at one point in the later years at Buildium, he sort of stepped back, he became a board member and was still involved in the business, but not in the same way on a day to day basis.
He started looking for something new to work on and he ultimately came to me and said, you know what, I think this idea for sort of a starter stack for a SaaS business is something that I've kind of built once before.
You've seen how effective it was.
Would you want to work with me on this?
So we started and worked on it for a couple of years in a part time capacity prior to the sale of buildium.
Omer (09:40.960)
Okay, so 2016, you guys get started and then at what point did you ship the first version of the product?
Geoff Roberts (09:47.600)
Yeah, I would say in general it took us about two years to deliver our mvp, which I know sounds kind of nuts, but we were working on this part time.
And the other thing that's unique about Outseta was to deliver on the value prop of the product.
We needed the complete feature set.
We needed billing, we needed email, we needed CRM, we needed help desk.
So it really wasn't building a single piece of software.
It was really more like building four or five pieces of software to be able to deliver the benefits that you get out of a single platform.
So about two years to an mvp.
Honestly, we struggled in year three, and then years four, five and six, the business really took off.
Omer (10:26.520)
What was the struggle in year three?
Geoff Roberts (10:28.770)
Yeah, the struggle in year three, I would say, was we were trying to change the predominant behavior of developers.
So developers are used to sort of assembling the perfect tech stack from all these different tools.
They have the technical skill set to do that work.
And we were going to them and saying, speed to market is important.
We can give you this all in one platform much, much more quickly, give you more time to focus on building product.
And even when they acknowledged that, that made sort of logical sense.
A lot of developers are just passionate about their craft and they would go back and assemble the perfect tech stack anyways.
And I think beyond that, developers are just a tough market.
They're familiar with software, they're demanding buyers, and I think so many founders, when they struggle, initially sort of wonder like, why isn't someone buying my product?
When the real question should be, why would they buy my product?
And the truth of the matter is the early versions of Outseta that I showed to developers, whether it was the email functionality or the CRM or the billing system, the response was often just kind of a shrug.
And there's 20 other email tools that do this, there's 20 other CRMs, and that was very true.
So it just took us a long time to build the feature set to the point where it was truly competitive with the point solutions that we compete against.
Omer (11:51.000)
So your ICP in those first few
Geoff Roberts (11:54.440)
years was a developer 100%, a developer that just founded a SaaS company, typically working either by themself as a solo founder or within the context of a very small team.
Omer (12:08.840)
And so what changed after year three?
Did you figure out the right feature set to get those people excited, or did you focus on a different.
Geoff Roberts (12:20.240)
So I think we've had the feature set correct since day one.
Not to sound cocky, but I'm not surprised by that.
I think it's pretty clear if you look at subscription businesses, across all types of subscription businesses, they use very similar tooling.
So we were able to narrow in on that pretty quickly.
I think two things ultimately really helped us start to grow.
One was and totally my fault.
We niched down on that ICP of the developer to a fault.
People had started to mumble in my ear about like no code builders and membership sites and these other use cases that outset it could be used for.
And I sort of ignored all of that as noise, but I was wrong.
So I'd say two things happened.
One is we kind of got discovered by the no code community, people building on webflow in particular.
And what we found was the all in one sort of fully integrated nature of outseta held that much more value for a less technical founder that doesn't have the skill set to assemble the perfect tech stack than the developer.
So as soon as we started paying attention to no code, that was really the thing that kickstarted our growth in a significant way, at least to start.
And then from there we've actually seen developers kind of come roaring back over the last couple of years.
And I think that's just a matter of our product maturing.
It took us a while to, you know, build each of the feature sets to the point where they were truly competitive with the other offerings on the market.
But as we got closer and closer to feature parity, developers started to take us more seriously.
And today our customer base is roughly split between no coders and developers.
Omer (13:59.530)
Wow.
If someone is listening to this and thinking, okay, the product sounds interesting, it's so it's I understand the use case, but if I'm going and using a horizontal product like this, I'm not getting best of breed, CRM, best of breed help desk, all of these other things.
What's your answer to that?
Why do you think that you've been able to overcome that type of objection and now it is resonating with people and especially developers who are making up a big chunk of your customer base.
Geoff Roberts (14:36.230)
Yeah, we hear this all the time.
There's sort of two themes that we hear.
It's outseta sounds too good to be true.
And if you do all those things, you can't do any of them well.
And I think there's two counterpoints that we make.
Not to make a counterpoint, I think they're very true.
But one is if you are assembling sort of best in class software and you look at the extent to which you use each of those pieces of software, particularly in the context of an early stage business, you're almost always, always fractionally using that tool.
I don't know anyone that's sort of like using every piece of software that they've bought to its full potential.
And a lot of the feature set that you're paying for typically is integrations with other tools or features to help you go up market that simply aren't that relevant to an early stage business.
So we kind of push back on that and we say we might not have feature parity, but we have the 80% of each feature that really matters that you need at an early stage.
And I think the other part of it is a reflection on our target market.
We aren't selling to big established companies that have really advanced needs.
We're selling to young companies.
And it goes back to can we deliver the 80% feature that they really need to send email communications or start doing subscription billing or track your prospects and customers in the CRM.
Smaller organizations have less complexity, have more basic needs.
So we don't need to build true feature parity with some of the tools that we compete against.
Omer (16:04.450)
Okay, cool.
So you spent about two years building the product.
We talked about year three being a bit of a struggle.
How long did it take to get the first 10 or 20 customers?
Geoff Roberts (16:19.970)
The first 10 or 20 customers didn't take too long.
We definitely got there, you know, after we released the MVP, about two years.
In between year two and three, we certainly got to 10 or 20 customers.
A lot of those, as you would expect.
I don't want to discount anybody getting to 10 or 20 customers because that's a huge leap in and of itself.
But a lot of them came, you know, referrals through our network and people that just knew what we were working on and were excited about it, that kind of thing.
But I think once you kind of get to those 10 or 20 customers that you have some pre existing relationships with, then it becomes really interesting.
It's can you go out and get those net new customers?
And that was certainly more challenging.
Omer (17:01.840)
So let's talk about that.
So I want to kind of figure out from a marketing and sales perspective what you did to grow the business.
Before we get into that, it'll be give us a sense of the size of the business where you are today in terms of revenue, customers and so on.
Geoff Roberts (17:15.920)
So today there's a few different measures we can give you.
We don't share our revenue publicly, but as a company we're five full time employees.
We probably sound smaller than we are because we are trying to stay intentionally small and independent.
But five full time employees, a few contractors.
We have about 6,000 companies using outs that are today.
But admittedly a lot of them are still on a free plan.
So that's not all of our paying subscribers, and we're not at $1 million in revenue yet, but we're fast approaching.
Omer (17:46.940)
Okay, so, yeah, let's talk about where that growth has come from.
What would you say has been one of the biggest marketing channels that you've been able to basically figure out and crank and start getting customers through?
Geoff Roberts (18:03.600)
Yeah, the big one is definitely content marketing.
For us, it goes back to.
I have a writing background, so the day that we started writing code, I started writing content for Outseta.
And as you hear about all things content marketing, it takes a while for that to start to compound in and of itself.
But having started early enough, that was really kicking in by the time we had an MVP out the door.
And a lot of it, to be honest, was really just writing about our own entrepreneurial journey.
But I find that even though we're not sort of targeting keywords that are relative to our business in a huge way, our audience is other founders, and they're sort of naturally curious to hear about other companies founding stories and entrepreneurial journeys.
So that's really the content that has resonated the most and driven us the most customers.
And then beyond that, a couple of partnerships where we have partnerships with both Stripe and Webflow.
Those are like our second and third biggest sources of leads at this point.
Omer (19:01.620)
Okay, great.
So from a content marketing perspective, it's not really an SEO play, I think.
Right.
And from having seen the content on your site, it's not the typical kind of stuff that we might see in terms of how to build a SaaS product or something like that you're actually telling.
They're kind of pretty deep, thoughtful content pieces.
You know, whenever I see somebody writing like that, I'm like, I wish I could write like that.
Right.
So obviously you've been doing it for years and you have the training there, but how do you figure out, like, one of the biggest kind of, I think, challenges with creating a piece of content is, is it worth the time and effort?
Is anyone going to care?
Is anyone going to find it?
And so when you approach what you're doing, how do you think about that and how much of it is focused on even though you're not thinking about SEO, but, you know, kind of keywords and discoverability versus just the merit of the content on its own and how useful or valuable it is?
And then also then what kind of effort do you put into sort of distribution of that content?
Geoff Roberts (20:17.530)
Yeah, I have an answer here that most people will hate and probably find to be not that helpful, but I'll give it to you as I see it.
I don't want to say that I never think about SEO.
I don't want to say that I never think about is this content going to be valuable to our audience.
I'm a marketer, so I certainly think about these things.
But I have pretty much, at least at outset, not written any content specifically because I saw an SEO opportunity or anything like that.
I almost exclusively write when I feel inspired and I have something to say.
And I don't publish on any sort of calendar.
I don't have like a certain number of blog posts a month.
I want to publish when there is something that happens in the context of our business or when I see a trend in SaaS and I feel like I have to say something about it, I sit down and I write and I think about it in the sense of if it's stirring up something inside of me to the extent where I feel like I need to write about it, there's probably someone else out there that it's going to resonate with as well.
And that might be a really lousy strategy.
But I think the other aspect of this was I've always looked at content as more about brand building than anything else.
And one of the things I care a lot about as a marketer is sort of this idea of resonance overreach.
I don't chase social media, social media followers or anything like that.
I want to be the person who maybe I only write three articles every quarter, but I want to know that I have a small engaged audience that's going to read every single one of those articles.
I want to earn my time in your inbox, time in your mind, whatever it might be.
And I think while taking that approach might not drive us a ton of traffic or whatnot, I know that there are people out there that read everything that I publish and that's ultimately what has brought them back to outsado when they have an opportunity to use a product like ours.
Omer (22:19.900)
Yeah, I guess is the concept of like a thousand true fans versus, you know, hundred thousand people who kind of dabble in kind of what you do.
Geoff Roberts (22:27.980)
I want to make one counterpoint there too.
I don't just say that like from a place of I think I'm this great writer and just want to write nice stuff because it's flowery and that's what makes me feel good.
It also reflects the market that we're in.
So without said it specifically, like we sell CRM, we sell subscription billing, we sell email marketing.
These are insanely competitive Categories of software.
To the extent if we were to try to target those keywords, to be honest with you, we wouldn't make it anywhere.
So going back to Buildium, Buildium was actually the opposite.
Buildium was in this very underserved market.
There was a very clear keyword in that business.
It was property management software that was hyper relevant.
The search traffic for it was growing and I focused on that keyword very, very deliberately.
So it's not that I think that's a bad strategy, it's just that I needed to pick an approach to content that fit the business that we were building it out.
Omer (23:26.130)
Said I spoke to a founder earlier today actually and she mentioned something similar where when they started building out a content marketing strategy, she said, I kind of realized we were just publishing content for the sake of it.
And it was me too content.
And she said even I didn't care, wasn't interested in reading any of it.
Right.
And so that was the kind of the wake up call for her where she was like, no, I can't keep doing this.
And I think for me, as a, as a content creator as well, it's, that is the best kind of gauge for me is when I record an interview like this, this is like, is it something that I would be interested in listening to?
And if, if I'm like feeling like I'm just checking the boxes, I know I'm doing something wrong.
And it goes back to the same thing.
It's kind of like you can create a lot of content and possibly a lot of noise, but if there isn't that much value in it or resonance or I guess the signal to noise kind of ratio that they talk about, is it really worth it?
And if you care about the quality of what you're doing, the answer is a clear no.
Right.
Because you don't want to kind of wake up every day and feel like you're just creating stuff and it's kind of a bit crappy, but you're just checking the boxes and getting stuff out there.
So it totally makes sense.
Okay, great.
So content marketing, that's been one of the growth channels.
Not the typical way that a lot of SaaS companies approach that, but if it's working for you, that's great.
Tell me about the partnerships with Stripe and webflow.
What exactly does that comprise this working with those two companies?
Geoff Roberts (25:07.490)
Yeah, so they're both similar, but different.
And I think one of the interesting things about both those partnerships is how quickly they came to fruition.
Literally.
I sent an email to the Stripe team.
I sent an email to the webflow team.
I said, we're building a complimentary product.
Can we get listed as partners?
And within a couple days we were on both of their websites.
And over the last few years they've sent us innumerable leads, customers, etc.
I think there's a lesson in there somewhere.
Not that partnerships is necessarily the right strategy to pursue, but we talk so much about, especially in content marketing, consistency and doing the same sort of things over a long period of time.
But there are sometimes things that just pay outsized dividends if you're just out there sort of pushing on the right doors.
And that's certainly an example within the context of our business.
So with Stripe, outseta is basically a tech stack built on top of Stripe.
And in many ways we started building out setup when we did because what's now become known as Stripe billing didn't exist.
There wasn't a great way in 2016 for founders of SaaS companies to launch billing essentially, unless they were integrating directly with Stripe's APIs.
So we said, let's go out and build sort of a tech stack on top of Stripe.
That's what we did.
And basically, if you go to their website today and you're looking through recurring billing tools, you can find Outseta.
And it's interesting because now that Stripe billing does exist, Stripe billing and Outseta from a subscription billing perspective are very, very similar.
So our point of differentiation at this point has become that we are this all in one tech stack that gives you authentication and email and CRM, even though our billing systems are quite, quite similar.
Webflow was kind of a similar story up until very, very recently.
Like within the last six months, webflow did not offer any sort of subscription payment functionality within their product, and they also didn't have authentication tools of any sort.
So I literally just emailed their support team and said, hey, we offer subscription billing and authentication.
It can be integrated with webflow sites really, really quickly.
Can we get listed as a partner?
They literally came back like the next day and said, yes, our customers desperately need the tools that you're offering.
You're a partner of ours.
And similarly, since webflow has launched comparable functionality now, again, the point of differentiation is yes, you can use webflow's billing and authentication tools, but Outsata kind of gives you this all encompassing business in a way that none of these other products do.
So that's what those two channels look like.
Omer (27:48.660)
How has that changed with webflow?
Because they have their own kind of authentication paywall service.
Now, right?
Geoff Roberts (27:57.540)
They do.
I think at the end of the day, it comes down to Outsetta is different from what they offer.
Certainly there's overlap, but if you're a company that is the size of a webflow or the size of a stripe, whatever these differences between products are, are going to be meaningful to some group of buyers.
And I've talked with webflow's CEO about this.
His word for word response to me was there's plenty of webflow to go around and there's going to be some percentage of people that say I want to use webflow's native features and some percentage of people that say I'd really love to have this perfectly integrated tech stack right out of the box.
So I think there's a lot to be learned from.
Even if there is some overlap in functionality, some buyers are going to care about your points of differentiation.
Omer (28:50.230)
So what kind of products are people building on webflow with Outsetter?
Is it kind of like mostly kind of membership type stuff or is it kind of no code type tools that they're trying to build?
Geoff Roberts (29:04.630)
Yeah, I would say to date, and this is changing a little bit, which is exciting, but to date there's kind of two common themes.
One would be sort of what you see with our own business.
So we're a traditional SaaS company, we've got a product built with code, but our marketing site is built on webflow and users come to our website, they pick a plan, they sign up for their subscription, et cetera.
So there are a lot of SaaS companies that just use Webflow for their marketing site and that's one bucket.
The other is membership sites where the actual website is the product and typically that's some sort of written content or video tutorials where you're charging for access to that content.
That's really like what sparked our initial growth within the no code community.
But more and more we are seeing people push webflow and essentially use webflow as a front end, some sort of database on the back end.
And then outsetta is kind of a tool set that ties it all together and build not just a membership website, but actual like fully functioning web apps.
Certainly they're more basic in nature than what you can build with code, but I think that's something we're seeing across the board.
Now, whether it's Bubble or webflow or a lot of these other no code tools can actually be used to deliver functional product in a way that they couldn't be before.
Omer (30:25.550)
Yeah, I mean, I think the whole no code thing is so Impressive how that's kind of taken off and how people with no technical skills are building products.
There's still something about it personally for me that I struggle with.
It feels like you're kind of stitching together a whole bunch of things and every day you wake up and something could break because an API failed or here and there and I don't know just in terms of managing it, it just feels like a headache.
But I also remember like before Stripe Billing actually building a SaaS product and doing all the integration work and coding all of that stuff myself.
And I remember what a pain that was as well.
So I don't think there's any perfect solution here.
But it's interesting how you're able to now kind of serve both needs, right?
In terms of non technical no code creators and developers, you know, building their own products.
Geoff Roberts (31:27.180)
Yeah, that's been a really interesting part of our journey.
And one of the questions I'm constantly getting asked is like, when are you going to pick a target market and niche down on them?
Are you going to go all in on SaaS?
Are you going to go all in on no code?
And it's a totally fair question.
I mean I would be asking myself that question.
But I think what we've found over time is the needs of the businesses in terms of the tooling that we offer are essentially the same, are very, very similar.
And we went through this huge process in between kind of year three and year four where we took a product that was meant for developers and we sort of no codified it.
And that basically just means we made it so a non technical user could implement Outsetta on a website very easily.
But at the end of the day, making any technology easier to integrate, easier to implement, it helps the no coders, but it also helps the developers.
It just helps them get things done faster.
You can still integrate OUTSETA with code if you want to, but by no means do you need to.
And I think that's a benefit to everybody.
Omer (32:29.060)
Do you find that your go to market strategy is challenging because if somebody is discovering the product, they can figure out for themselves whether it makes sense for them or not.
But when you're having to go out and think about positioning and messaging and all of these things and you're speaking to two very different types of potential customers with two pretty different use cases, does that create more complexity than you feel you should have to deal with?
Geoff Roberts (33:05.060)
It does, without question.
I don't think of it as so much being challenging from a go to market perspective.
It certainly is.
There's communities of no code founders and communities of technical founders and there's very little overlap.
There's.
But I tend to think more and more people are looking at OUTSETA and seeing it as sort of a low code solution for whatever that's worth, and realizing there's some middle ground.
The more advanced technically no coders tend to be the more successful ones.
And we're seeing developers more and more care about speed to market and use no code tools more broadly.
So it hasn't actually been too challenging in that regard.
I think where it's really challenging is when it comes to customer support.
So we will have incoming questions from onboarding customers, some of which are completely non technical people who in some cases are like, what is a URL?
Literally?
And on the other side we've got software engineers that have been building software for 20 years asking technical questions that are way over my head.
And we need to very quickly sort of suss out who are we talking to, how technical are they, do they need code snippets in the response or do they need us to explain very fundamental concepts with regards to building software to them?
And that's always challenging and very much a work in progress.
Omer (34:34.900)
It reminds me of a hosting company I used to use many years ago, I think it was called Dreamhost.
And when you created a support ticket they used to have this dropdown which used to say something like, what's your level of knowledge about this?
And I think the simplest option was something like, look, I'm a newbie, I don't know anything.
And then number four or five on the scale was, no offense, I probably know more than you.
And so it was.
That was kind of like very useful because when you then it's really frustrating when you're kind of more of a technical user and you're contacting support and they're taking you through all the basic stuff.
Right?
So that was a good way, I guess, that they were filtering people out.
Geoff Roberts (35:17.090)
We haven't done anything like that, although we've talked about it.
And I think something like that could be certainly in our future.
But it's actually interesting.
Just like my own skill set, I am fairly non technical.
And I think one of the benefits of that is when it comes to no code implementations of Outseta, I'm like the perfect test dummy.
It's like, what can Jeff build as a non technical person?
And I think a lot of our no code customers sort of gravitate towards working with me because I'm the same level of technical idiot that they are and they recognize that.
But the flip side of that is then I'll be talking to a super experienced developer and they're asking really technical questions that I'm not prepared to answer.
And they're like, aren't you the co founder of this company and you don't know how to answer my question?
And I'm like, oh yeah, we've got another co founder who is an engineer who can help you with that.
So it is an interesting challenge for
Omer (36:10.580)
sure with that kind of ICP in mind, you know, kind of someone, whether they're technical or non technical, building a SaaS business, early stages, that's what you're going after.
You decided that one of the areas that you were going to focus on were accelerators and incubators.
That sounds on the face of it a pretty good place to find these people.
How did that work out for you?
Geoff Roberts (36:38.310)
Yeah, I would think so.
That was initially like a big part of my go to market strategy or hypotheses at least was if we can partner with some of these organizations, think Y Combinator, Techstars, etc.
They can get our product in the hands of a perfect audience at the right stage.
We did pursue a lot of that and nothing, nothing came of it.
Literally nothing.
And I think it comes down to most of these sorts of accelerators or incubators or whatnot have some sort of perks program.
And at this point they all kind of have the same perks.
It's like you can sign up here for 20% off HubSpot and some AWS credits and whatnot.
So I'm not saying those perks aren't appealing, but it's kind of like when everyone is offering them, it's just not that special.
Omer (37:26.520)
How long did it take you to figure that out?
And like how much time did you put into trying to work with these accelerators and incubators?
Geoff Roberts (37:33.190)
I would say probably like six months.
We established a couple of pretty big partnerships.
Techstars was one.
We put some work into establishing the partnership, but we were pretty bullish on it and really marketed it aggressively for a few months thereafter.
And after coming up empty for a while, I think we just said we need to find another way to acquire customers, unfortunately.
But nothing ventured, nothing gained.
Omer (37:56.640)
Totally.
Yeah.
I mean there's no silver bullet, right?
You gotta, it's like if you could grow by, you know, painting by numbers, everybody would be doing it.
So that's the fun part of it.
Tell me about the five FTEs.
What's the makeup in terms of developers,
Geoff Roberts (38:14.160)
et cetera, we are still a very engineering heavy company, largely just due to the size and scale of what we're building.
Right.
It is this huge, huge product.
It is pretty complex in terms of building what we've built.
And we've always known since the get go we needed a lot of engineering firepower to make this viable, particularly because we're bootstrapping.
So three of the five employees are developers.
They are all developers who have been building software for 20, 25 years.
They have all been CTOs at multiple companies.
It is a three person engineering team, but it is the mightiest engineering team certainly I have ever worked with.
And if you look at what they've pushed out just between the three of them, it's pretty remarkable.
We have one designer, his name is James.
He does everything from brand design to the actual UI of the software.
And then there's me, who's basically the utility infielder of sorts.
Certainly I come from a marketing background, but I handle most of the business side of the company.
I do everything from product management to sales to marketing to support to internal ops and all that kind of stuff.
Omer (39:28.080)
Your designer, when did you hire that person?
Geoff Roberts (39:31.440)
Yeah, we brought him on in year three.
So the first couple of years when we were building the mvp, we definitely took sort of some shortcuts around the ui.
We used kind of a templated UI because we just said there's so much functionality that we need to build.
Let's stick with kind of tried and true design patterns and just get the functionality out the door.
In year three, we brought James on.
He is a great example of sort of our organizational structure and organizational model.
We brought him initially onto the team working 20 hours a month, so a super part time capacity.
I think we were paying him for 10 hours of his time every month and then giving him 10 hours of equity in the business.
And he worked in that capacity for probably almost two years and then he kind of kicked up his involvement and now he's full time.
But over the couple years where he was working for us 20 hours a month, he built up a 3 or 4% ownership stake in the company, which is dramatically more equity than you'd typically see someone with that level of involvement get.
Now the company's doing better, he's come on full time and is making a salary and all of that.
But all of us sort of went from this very part time involvement with Outseta eventually into a full time role as our revenue permitted.
Omer (40:51.480)
Yeah, I mean, that's one of the things that I like about Outseta is I think you have invested in design.
The product looks great.
One of my kind of beefs and I always wonder whether I'm just kind of a picky user.
You know, I go through so many SaaS products.
Right.
It's just what I'm doing.
Right.
And one of the things that always drains the energy out of me is when you start on the marketing site and everything looks great and the screenshots look great and then you log into the product and you're like, oh, it's like it's.
I can't use it.
It's just, it's just not a nice experience.
And so I think you've done a good job there in terms of.
Or James has done a good job there in terms of having that consistency between the marketing site and the product and a decent user experience.
So I think there's some really good lessons there that anybody who's going and building a product, I think they should take a look at that because I think there's a bunch of stuff that they can learn from that.
Let's talk about the organization structure because you guys have a very interesting way of organizing yourselves and how you compensate people.
Tell us about that.
Geoff Roberts (42:02.140)
Yeah, so this is a big part of the reason our founding team came together.
We had a lot of philosophical alignment on if we were going to build something new, how we wanted to build it.
And there's sort of a few pillars of that that I'll speak to quickly.
The first one was we wanted to stay small and independent by design.
And while Buildium was this big success, we kind of looked at that business and we said we had a lot more fun when we were a company of 20 people, are a lot more fun at 20 people than we had at 200 people.
And I think just as you grow headcount that much, the organization slows down.
There becomes some inner politics, all those sorts of things.
So we said, let's stay small.
And aside from that, we see a lot of inefficiency in the headcount that gets added to these venture backed companies.
You see big sales organizations get built out, you see big customer service organizations get built out.
And when we looked at that, we said, you know what, a lot of those customer service reps, and I'm just using that as an example, ultimately are really just escalating tickets to the engineers who can fix the problem.
And we said, why don't we just use a different model where everybody does support.
We hire really senior people and the people that are Responding to your support tickets are the ones that can actually fix the problem for you too.
So there's kind of this fundamental belief or objective within Outsetta to see how far we can push the company with about 20 people.
And that's an artificial cap, we could certainly grow over that.
But we want to sort of artificially constrain ourselves because we think it breeds a lot of good habits.
And if we're hiring really senior, excellent people, we think we can solve problems without just throwing bodies at them.
Essentially the second part of it is we are what's called self managed.
That basically just means there's no bosses.
So the overarching sentiment is we're trying to empower autonomous decision making and we're trying to just bring the best people into the company that we possibly can, sort of let them figure out where they can best contribute and just let them do their thing without the need for boss or oversight or anything like that.
So that also is easier to do in the context of a smaller team rather than a larger team.
But that was really important to us.
And then because of the product that we offer, we know that the people that work at outseta are going to be entrepreneurial type people in general, or most likely will be.
So we wanted to come up with a flexible compensation model that allows people to work on other projects.
So we've standardized the salary.
If you work on Outseta, regardless of your role, five days a week, you make $210,000 per year.
But you can choose how many days you want to work.
So if you want to work one day a week, it's $42,000 a year, two days a week, it's $84,000 a year, all the way up to that full time salary.
Alternatively, you can also choose to what extent you want to work for equity in the business, and you can devote a certain number of days per week to working for equity.
So right now, using myself as an example, I'm getting paid for three days a week.
That's a salary of $126,000 a year.
And then two days a week I'm working for equity and building up my equity stake in Outseta.
And it's kind of a pick your own adventure model, which we think is appealing to people and a nice recruiting tool.
But beyond that, there's no like, everyone's treated the same.
If, if you come on to Outset, you get equity on the exact same terms as my equity as a founder.
You get paid the exact same much the exact same amount that I get paid.
So it's very much like a membership based organization similar to a DAO that we've employed at this point.
Omer (45:46.760)
Cool, that's very interesting.
The compensation thing, if you can make that work, sounds really interesting and I think appealing to a lot of people, this thing about having no bosses and people just doing what they want to do, that kind of sounds like it could either create opportunities for people to do their best work.
Like for me I spend a bunch of time on marketing, but I love product ux, dabbling in code when I can.
And so when you're working for somebody and you're kind of just in this one, one kind of vertical, right.
You, you don't step outside of that because you're gonna, you know, you're gonna step on other people's feet and whatever.
Right.
So I think, I think this, this thing about saying let's take people's talents and figure out where they can help is great.
But it also sounds like a recipe for a lot of chaos.
Geoff Roberts (46:38.750)
It does.
So I think the thing that is a prerequisite to make this work, I'd say there's two things.
One is the size of the organization.
There's a lot of argument out there about whether self managed companies can scale to hundreds or thousands of employees.
There are examples of that happening.
Personally, although I'm a proponent of self management, I think this will break down if we get large enough in terms of headcount.
So I think this is something that works well within a smaller organization, certainly under 20 people.
I think it's going to be fine and I think it's a benefit.
Secondarily you have to give everybody all the information about the business.
This is really the thing that is a key.
So when you talk about radical transparency, you get that at outset of there's no information that I have that every other employee in the company doesn't have.
And that's a key because you can't just sort of let people loose if they don't know what the guardrails are, if they don't know what we're trying to achieve.
If it was a total free for all, someone could run off and make a budgetary decision when there isn't budget there.
So everyone needs to know like here's the bank account, here's what's in it, here's what we're trying to achieve.
And while we're trying to empower autonomy, you know, if someone's going to make a huge decision around building a feature or spending money or something like that, you know, they, we Talk within the context of the company about it and we, you know, it's discussed.
It's not just a total, total free for all.
And that's, that's the way it should be.
Ultimately.
Omer (48:12.460)
We should wrap up and get onto the lightning round.
Before we do that, I got one more question for you.
You talked about having, you know, this 6,000 odd customers or so, but you, you mentioned that a lot of them was free users.
You don't have a free plan currently.
You did have a freemium model, which.
How did that work out, by the way?
Geoff Roberts (48:34.310)
Yeah, it was kind of in many ways a disaster.
And I don't say that to be extreme.
I think this is a really important learning point and something I don't see people talking about enough, which is does the strategy fit the business essentially and how you want to build the business?
And I see this even more commonly with like the bootstrapping versus VC funding argument.
It's like people take sides and it's like this shouldn't be, you're on the bootstrapping side or you're on the venture capital side.
It should be what are your goals and do you need VC funding to fulfill them and to build what you need to build, or just bootstrapping make more sense.
But I think it's the same here with our freemium tier.
When we were initially designing our customer acquisition strategy, my overarching mindset was let's build the perfect experience that I would want to experience as a buyer of this product.
And part of that without question was you can get started with Outseta for free and you don't pay anything until you sort of launch your product and start to grow.
That was the initial thought.
It was well intentioned, it was customer friendly.
But as a small bootstrap team, what that meant practically was we got to a point where we were having thousands of free users sign up every single month and we were needing to provide onboarding help and support to thousands of non paying users.
And as a small team, it just got to the point where I was doing support full time.
Our other team members, our engineers, weren't building product, they were doing support full time.
And we just said, we need to correct this problem.
We can't support, in the context of five people, thousands of free users onboarding into the software every month.
So we actually overcorrected sort of intentionally to save our butts, to be honest.
We went directly to paid.
There was no trial, there was no freemium nothing.
You had to literally sign up and pay for the product in order to even experience it.
We did that for a couple months.
That kind of settled things down, as you would expect.
We did see churn go up.
There was certainly some percentage of people that would sign up for the paid product, realize it didn't do the things it needed it to do, they needed it to do, and then they would churn.
So we sort of found a nice middle ground where we now offer a seven day free trial with a credit card upfront that then auto converts into a paid subscription.
And really interestingly, we get a lot of pushback on that.
People say, you know, I want to take all the time that I need to integrate Outseta.
You should go back to having a pricing model like you had before.
And we explained to them we actually have a blog post about this, I send to them that sort of details the whole journey.
And I say, you know, as a small bootstrap team, that just wasn't sustainable for us.
The seven day trial is really meant for you to evaluate the software, not meant for you to implement it in full.
And when you explain it like a human being and you're explaining it to another founder who has the same sorts of challenges and concerns and all of that, they almost unequivocally get it and say, that makes total sense.
Like, we'll use our seven day trial to check out the product and if we like it, we'll.
We'll buy it and that's that.
Omer (51:39.600)
All right, let's get onto the lightning round.
I've got seven quick fire questions for you.
Just try to answer them as quickly as you can.
All right, ready?
Geoff Roberts (51:48.160)
Yep.
Omer (51:48.800)
What's one piece of business advice that you've received?
Geoff Roberts (51:51.760)
One piece of business advice.
My first marketing mentor, her name's Nancy Freitas.
She was the CMO at Constant Contact.
I was struggling with not being more technical early in my career.
I asked her if I should learn to code.
She said, absolutely not.
Her point was marketing is a big enough thing.
You've got a lot to learn on the marketing side of things without worrying about learning to write code.
And I think in retrospect, she was absolutely right.
Omer (52:17.830)
What book would you recommend to our audience and why?
Geoff Roberts (52:21.910)
Reinventing Organizations by Frederic Laloux.
That is just a book that completely changed my mind in terms of what's possible when it comes to how you build companies.
I think there's so little innovation around how we actually build companies that that book just changed my mindset altogether.
And then the second one is Life Profitability by Adi Pinar.
That book just basically asks you to look at your business and sort of do accounting not just in terms of the finances of your business, but accounting in terms of how happy your entrepreneurial experience is making you.
Omer (52:58.130)
What's one attribute or characteristic in your mind of a successful founder?
Geoff Roberts (53:02.420)
I think managing your mental health and your psychology and just staying in the game long term is probably the most important thing.
Omer (53:09.940)
What's your favorite personal productivity tool or habit?
Geoff Roberts (53:12.820)
I have a horrible answer for you here.
This is another area where I'm sort of extremely in one direction.
I basically don't have any productivity tools or habits.
I use this kind of organic mindset of the most important things are going to continue to bubble up.
And if you don't have something continually bubbling up in your mind, it's probably not that important.
So I just kind of wake up and tackle whatever I deem to be the most important thing.
Wow.
Omer (53:42.640)
That would drive me nuts.
Just all these open loops in my head.
Wow, we should talk about that one day because I don't know how you make that work.
What's a new or crazy business idea you'd love to pursue if you had the extra time?
Geoff Roberts (53:56.640)
I've talked about this one before, but I live near the beach in San Diego, and if you walk out to the beach in the summer, people step on stingrays, and it is incredibly painful.
And there's no such thing as stingray boots.
These would be like boots that you can wear on your feet, you can surf with them, but they are impenetrable to a stingray.
And it's a ridiculous idea, but I see a market for it.
Omer (54:19.760)
There you go.
What's an interesting or fun fact about you that most people don't know?
Geoff Roberts (54:24.240)
I have authored a children's book.
It is the bestselling children's book ever written about Tom Brady.
It's called the Tale of Tom.
You can go to www.thetailoftom.com if you want to check it out.
Omer (54:36.540)
Tom Brady, the NFL.
Geoff Roberts (54:38.780)
That's right.
Yep.
Yep.
Tom Brady.
Omer (54:41.420)
Is this like an official children's bio or something?
Geoff Roberts (54:44.460)
Pretty much.
It's actually.
I wrote a book about a celebrity, so I actually had to form, like, an LLC and make sure my legal obligations were covered in case he decides he has a problem with the book and all that kind of stuff, which is ridiculous, but it's a children's book about Tom Brady.
Omer (54:59.750)
Wow.
And finally, what's one of your most important passions outside of your work?
Geoff Roberts (55:03.670)
Traveling, eating and playing golf.
Those are probably the three big ones.
Omer (55:08.550)
Love it.
All right, cool.
Well, thank you so much for joining me and sitting down and having this conversation sharing the story of Outseta.
Also, thanks for sharing some of these obstacles and lessons that you've challenges you've faced along the way and the lessons you've learned from those experiences.
If people want to find out more about Outsetter they can go to outset.com that's o u t s e t a dot com and if folks want to get in touch with you, what's the best way for them to do that?
Geoff Roberts (55:36.800)
You can find me either on Twitter or LinkedIn.
I am a Geoff so it's G E O F F T Roberts on Twitter or you can just email me.
It's jefftsata.com awesome.
Omer (55:48.400)
Thanks man.
It's been a pleasure and wish you and the team the best of success.
And you definitely have to let me know when you cross into the seven figure range.
Geoff Roberts (55:57.050)
Will do.
Thanks so much for having me.
Omer (55:58.850)
Cheers.
