Why Workshop deleted the per-user fee it had built on purpose
Price on the thing that grows when your customer gets more value. Then delete any charge that makes them pause before pulling in another department.


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Workshop's founding team spent nine months selling an intranet and earned about three customers. Prospects had named internal email as the real problem four months in, and Rick Knudtson dismissed it for another five. They rebuilt around email in 30 days and signed 10 customers. Workshop is now at eight-figure ARR.
Rick is blunt about what blocked him. He had just sold Flywheel, and the exit convinced him he knew what to build. By month nine, with roughly zero traction and more than half of a $3 million raise still in the bank, he was seriously considering handing the money back to investors.
Rick Knudtson is the co-founder and CEO of Workshop, an internal communications platform in Omaha, Nebraska, now at eight-figure ARR. Before this he co-founded Flywheel in 2012, a WordPress hosting platform for creative agencies, and sold it to WP Engine in 2019.
It did not start well. In late 2020 Rick and his co-founders went all in on internal communications, then picked the wrong product. Nobody loves their intranet, Rick reasoned, so a better-designed one should win. The founding team spent the first nine months of 2021 selling that intranet and earned about three customers. Nobody agreed on what an intranet was even for.
About four months in, they started hearing something else. Email is our number one channel and we have no visibility into it. Rick heard it and dismissed it for another five months. Email was not novel, and he had just come off an exit that told him he knew what to build. He calls it ego, plainly.
By month nine Workshop had roughly zero traction and more than half of a $3 million raise still in the bank, and Rick was pushing to return the money to investors. His co-founder and COO Derek Homann talked him and Ben Stevinson out of it at a bar in Omaha. Just listen to the damn customers. They rebuilt the platform around email in 30 days and signed 10 customers, against three in nine months.
In this interview, Rick explains why an exit made him a worse listener, why he thinks you should be marketing for a year before you sell anything, and how Workshop came to price by audience reached instead of per seat.
Workshop spent nine months selling an intranet and earned about three customers, while prospects repeatedly named internal email as their real problem. After co-founder and COO Derek Homann pushed the founding team to act on that feedback, Rick Knudtson and his co-founders rebuilt the product around email in 30 days, signed 10 customers, and Workshop has since reached eight-figure ARR in internal communications software.
Price on the thing that grows when your customer gets more value. Then delete any charge that makes them pause before pulling in another department.
You take the calls. You take the notes.
"Before you sell anything, you have to be marketing for a year.
Write the ebook. Put it behind a form.
How did Rick Knudtson recognise the product signal Workshop's customers kept handing him when his own ego was blocking it?
He did not, until co-founder and COO Derek Homann forced the issue at a bar in Omaha. Workshop rebuilt around email in 30 days and signed 10 customers, against 3 in nine months on the intranet.
Why did Workshop spend nine months building an intranet nobody wanted?
The founding team bet that nobody loves their intranet, so a better-designed one would win. But prospects had no shared definition of what an intranet solved, and Workshop earned only about three customers in nine months.
What made Rick Knudtson consider giving $3M back to Workshop's investors?
By month nine the company had roughly zero customers with more than half the raise still in the bank. He wanted to return it, preserve the investor relationships, and start something else.
How did Workshop get its first customers without a sales team?
It launched the Happy Monday Club newsletter on day one, co-marketed with other newsletters and communities, and ran Hudl as an unpaid design partner to learn the internal comms workflow in detail.
Why can't a large company just use MailChimp for internal communications?
Corporate security layers push external marketing tools into spam. Workshop had to build deliverability, image handling and governance so a message reaches 100,000 employees within minutes and survives IT review.
How does Workshop price its internal communications software?
Audience-based pricing. What a customer pays depends on how many employees they communicate to, plus which channels they buy. There is no per-seat charge, and extra-user fees were removed three years ago.
What is Workshop's positioning against intranets and employee apps?
Those are destinations employees rarely visit. Workshop is a distribution layer that pushes to email, SMS, Slack, Microsoft Teams and SharePoint and measures reach, so employees never see Workshop at all.
How big is Workshop today and how long did it take?
Five years in, Workshop has about 140 employees, just under 1,000 customers including Capgemini and its 400,000 global staff, and eight-figure ARR in internal communications software.
What content strategy worked for Rick Knudtson when he was not an internal comms expert?
He treated daily sales calls as research, then shipped what he heard: an internal comms calendar, a benchmarks report, roughly 50 ungated resources in twelve months, and monthly webinars that grew from 5 attendees to 500.
Rick Knudtson [00:00:00]:
It took us about nine months to maybe earn three customers on the intranet. It took us 30 days to get 10 customers on the email product. So we knew immediately that, like, okay, this resonates.
Rick Knudtson [00:00:10]:
By month nine, after we had about zero customers, we had raised, I think, $3 million out of the gates, my partners and I. I was a proponent of, like giving the money back to investors. I was like, ready to like, be like, hey, this is not working out.
Rick Knudtson [00:00:24]:
A co founder, Derek, our COO, who convinced myself and Ben to do the email thing. You know, I remember the moment that we did that, which was like, we were sitting at a bar in Omaha, we were deciding what we're gonna do with the company because it wasn't working out. And he was like, guys, just go.
Rick Knudtson [00:00:36]:
Just go try this one last thing. Just listen to the damn customers.
Omer Khan [00:00:39]:
Hey, welcome to The SaaS Podcast. I'm Omer Khan and this is a show where I sit down with real founders and dig into how they actually built their SaaS companies. I've had almost 500 of these conversations now, and I put out a new one every week to help you build and grow your startup.
Omer Khan [00:00:53]:
If that sounds useful, hit subscribe or check out saasclub.io to learn more. My guest today is Rick Knudtson, co founder and CEO of Workshop. He'd already built and sold one company, so he came into this with money and a network that most founders don't have.
Omer Khan [00:01:11]:
Still, it took him a year of building the wrong product and nearly handing the funding back to investors before Workshop became a business, which is now doing eight figures in ARR. In this interview, Rick breaks down the full year he spent marketing before he sold anything.
Omer Khan [00:01:29]:
The one thing customers kept telling him that he ignored for nine months. And the product rebuild that got him 10 customers in 30 days. After nine months of almost no customers. So I hope you enjoy it. Rick, welcome to the show.
Rick Knudtson [00:01:46]:
Awesome, thanks. Thanks for having me. Exciting.
Omer Khan [00:01:48]:
My pleasure. So tell us about Workshop. What does the product do and who's it for?
Rick Knudtson [00:01:54]:
Yeah, so we are a software company that helps pretty big companies communicate to their employees. So we have a kind of a multi channel internal communications platform designed to make comms at big companies collaborative and also provide visibility into who's reaching employees. Where are they at, how are they actually engaging with the content?
Rick Knudtson [00:02:14]:
And for pretty large companies, it can get pretty complicated. They have employees all over the globe and different geographies, different teams. They might have departments of 1000 employees. You can think of some pretty large organizations. So providing that visibility and that layer of Operating, sorry.
Rick Knudtson [00:02:31]:
The operating system for comms is really, really impactful for companies trying to align employees at scale and give us a.
Omer Khan [00:02:38]:
Sense of the size of the business. Where are you in terms of revenue, customers, size of team?
Rick Knudtson [00:02:43]:
Yeah, yeah, for sure. Yeah. So we're based here in Omaha, Nebraska. We have about 140 employees. Primarily most of them are here in Omaha, but also globally remote. We have a small team in Ireland as well and we have about just under a thousand customers today. Well beyond 10 million of ARR growing very quickly. Very exciting.
Rick Knudtson [00:03:06]:
But yeah, it's been a fun ride. We're just turned five years old, so it's been fun.
Omer Khan [00:03:11]:
Cool. Now before you founded Workshop, you co founded and eventually sold Flywheel in 2019. So just for context, for people who don't know, can you just explain what Flywheel did or does?
Rick Knudtson [00:03:27]:
Yeah, I get to describe myself as a serial entrepreneur now. Yeah, it's like, yeah. So yeah, a little over 10 years ago in 2012, I founded a company also based here in Omaha called Flywheel. We were in the WordPress hosting space.
Rick Knudtson [00:03:40]:
We were a website hosting platform and that was during kind of the rise of WordPress as a content management system. I imagine a lot of people listening might be using it as a CMS on their own website. About half of the Internet runs on it actually, so it's pretty massive.
Rick Knudtson [00:03:56]:
At the time though, only 10% of websites ran on it. So we kind of caught this wave of massive growth on that CMS and what we did actually was provided a platform specifically built for the creative agencies of the world working with clients, which is a little bit different than you managing your own e commerce store.
Rick Knudtson [00:04:14]:
So for us it was really about how do we help developers build websites, collaborate with their clients, maybe build their clients on our platform and really manage their website development business on our hosting tool. We did that from 2012, founded that company in 2019, we ended up selling it.
Rick Knudtson [00:04:32]:
We had about 30,000 global customers at the time, a little over 200 employees fully globally and it was an amazing ride. Another venture backed business and a lot of that experience actually led us to Workshop.
Rick Knudtson [00:04:45]:
But I'm happy to dive in anywhere because I could talk about Flywheel for two hours if we wanted to, but I don't think that's all that exciting.
Omer Khan [00:04:52]:
So where did the idea for Workshop come from?
Rick Knudtson [00:04:55]:
When I started Flywheel, I was 24 years old. I didn't know anything about building companies, I didn't know anything about scaling organizations. We were venture backed. We obviously were expected to grow fast. And we were lucky enough to do exactly that.
Rick Knudtson [00:05:07]:
And what we learned as a founding team, I had two partners, was that honestly, the only thing that is constant is change when you're growing fast. So trying to communicate all of this change was super important.
Rick Knudtson [00:05:19]:
And then we were also, for the most part, a remote first company because we had technical support teams all over the world. So from an early stage, we had to communicate to folks, you know, across the world in different time zones. So we really leaned into digital communication as kind of the cultural driver.
Rick Knudtson [00:05:36]:
Now, I will say that we. We didn't know internal communications was a thing. We were just kind of doing what the company kind of demanded of us, which is like, hey, we're launching new products, we have new sales teams over here. We have to communicate all this stuff.
Rick Knudtson [00:05:47]:
And I started wanting to understand how our employees were engaging with the content. Like, were they actually reading it? Like, was it landing? So I started borrowing time in my marketing team's platform, which was HubSpot at the time, to send emails that are a little bit more, I guess, visually interesting and maybe on brand, more engaging.
Rick Knudtson [00:06:08]:
And the problem with that is it kind of solves some of the problems of like, hey, let's build engaging comms and I can get some data, but it messes up all your marketing data. So my CMO kicked me out of that pretty quickly and was like, this is not going to work.
Rick Knudtson [00:06:19]:
So we ended up using a combination of Mailchimp, internally HubSpot for external comms. And then we also were a Slack culture. So we had kind of built this almost like duct tape solution together to understand, like, here's our comm stack and here's some data we can get around how our employees are engaging with the content.
Rick Knudtson [00:06:37]:
And then to be honest, when we sold the business, the acquiring company, the company called WP Engine, biggest WordPress hosting platform in the world today. The combined company was about 1200 employees. So I got to see communication at a very different scale.
Rick Knudtson [00:06:51]:
You know, you know, where strategy was far more intentional, the tool set was far more intentional. And then that was June of 2019, when we sold the business. We operated pretty independently for six months. And then it was about January, February, we started integrating the organizations. And then of course, March of 2020 changed everything.
Rick Knudtson [00:07:08]:
And then suddenly, like, we're going remote and communicating through this change of COVID and kind of remote posture and integrating organizations. So actually what happened at WP Engine is they went out and tried to find a. A platform for communication through that kind of that challenging time.
Rick Knudtson [00:07:25]:
I Got to sit kind of alongside that search effort because I was helping with a lot of the communication strategy on my side of the business during that integration.
Rick Knudtson [00:07:35]:
And it was the first time that I got to explore the industry that we're working in today at Workshop, which was like, oh, there's a lot of tools out there, but they seem to be pretty, I would say like focused on building a destination for employees.
Rick Knudtson [00:07:50]:
They were kind of built in the pre Slack pre Teams era where I kind of describe it as like when companies really operated in one channel to communicate to employees, which is like maybe email.
Rick Knudtson [00:08:03]:
And then over the last say decade or 15 years or so now it's probably very common in almost every company that you have certainly email, but you probably have an intranet of some sort. And we now have always on company chat in Teams and Slack, which a decade ago wasn't the case at every organization.
Rick Knudtson [00:08:19]:
So now there's this true multi channel thing. So during that search at the acquiring company, it became pretty obvious there was a cool opportunity in this space and I was already passionate about communication that it got my gear spinning on. Like maybe this is like something that we can build.
Rick Knudtson [00:08:36]:
So that's kind of like the first moment where I thought, okay, this could be a company, a product. And of course I was still working at the company. So it was months later that we started. Started the business though.
Omer Khan [00:08:46]:
Yeah. So walk me through the moment where you decided that you were going to do this thing and what kind of research or data or whatever it was did you need to have to feel confident that this was the thing you were going to spend the next five years on?
Rick Knudtson [00:09:08]:
Yeah. So it was mid-2020. I got reconnected with my two business partners that are now my co founders at Workshop. They were actually, they were just, they were actually in a similar situation. They had just sold a bootstrap software company of their own. They were exploring remote tools. I had a lot of respect for these guys.
Rick Knudtson [00:09:24]:
They're local to Omaha as well. I had known them in the community, honestly always had in the back of my mind the opportunity to work with them would be amazing. So we got reconnected and we started exploring some tools for remote work in mid-2020 because I guess jokingly I don't make a great employee.
Rick Knudtson [00:09:41]:
So I was already trying to figure out what I was going to do next.
Rick Knudtson [00:09:44]:
And so I was exploring lots of at the time and I still had this idea of communication tools in the back of my mind and I kind of presented that to the guys and it kind of fit the mold of like there's this trend in the world where remote first work is going to be the constant.
Rick Knudtson [00:10:01]:
So whether companies come back to office probably doesn't change the fact that every organization is going to have way more flexibility. So this is more important than ever. You have to be a digital remote first company, even if you have an office today. So it felt like it was the right time to build it.
Rick Knudtson [00:10:15]:
So we decided to actually kind of go all in on it late 2020 and started exploring very specifically what we would end up building in the communication space. To be honest, we wrote the mission statement of a company first. And this is like just as a second time founder.
Rick Knudtson [00:10:30]:
One thing that I was really kind of worried about or focused on was you mentioned it. It's like, I'm going to spend the next five, ten years of my life on this thing. I don't think I knew that when I started Flywheel.
Rick Knudtson [00:10:41]:
You kind of like fell into it and then you wake up like seven years later and you're like, man, I didn't know I was going to commit a decade of my life to this company. And I knew that going in to this one.
Rick Knudtson [00:10:50]:
So I really wanted the mission to be the reason we do the work, which is to create more Happy Mondays for employees everywhere. We believe we can help companies do that with communication tools.
Rick Knudtson [00:10:59]:
So really it didn't say anything about like what are we going to build specifically, but that we really wanted to help companies drive culture and alignment and purpose in individuals work. And then we had this hypothesis, this thesis that maybe communication is the way to do that.
Rick Knudtson [00:11:15]:
So late 2020 we started exploring the market a little bit more deeply and understanding what was out in the space and how maybe we could differentiate. And to be honest, at the time we thought, man, no one really loves their intranet.
Rick Knudtson [00:11:32]:
If you talk to anyone that's used an intranet, which is just an internal website for only the company to see, no one's like, man, it's one of my favorite tools. I get to wake up every day and I go to the intranet, it's awesome.
Rick Knudtson [00:11:43]:
And that was actually a very similar experience that I had at Flywheel, which is like no one loved their website host.
Rick Knudtson [00:11:47]:
So I thought maybe with just a little bit of a design touch and a brand and experience or a product team that's focused on user experience, you could build something pretty special in just building a better intranet.
Rick Knudtson [00:11:58]:
So we started exploring that initially and through a lot of conversations with companies and prospects, what we learned was that the intranet is always inserted in the company for a very specific reason for that organization. It's almost like the last ditch effort to solve communication. It's like, I don't know where the directory of employees is.
Rick Knudtson [00:12:20]:
Well, let's build an intranet. I don't know where the files live. Let's build an intranet. So the intranet becomes this kind of mess of things and we couldn't find a through line on the real problem an intranet solves. But what we kept hearing was the number one channel that we have is email.
Rick Knudtson [00:12:38]:
And I have no visibility into how those things perform. But I wake up every day and I send a bunch of emails to our teams and my executives are asking what the data looks like and can we reach that geography. And that was kind of interesting.
Rick Knudtson [00:12:51]:
So we had no idea that email was the big problem until maybe four months into the company after talking with a ton of potential customers that clearly there's a big problem in 2022. At the time, that email's still a problem with big companies, which is kind of a crazy thing to think about.
Rick Knudtson [00:13:08]:
And that's when we decided to actually go after solving that specific problem, which was actually really late 21.
Omer Khan [00:13:15]:
You know, somebody who might listen to this might be thinking, if you hear something like that, like people telling you email is a problem and the kind of communications that you were talking about, it seems like, couldn't they solve that problem?
Omer Khan [00:13:34]:
Okay, maybe they can't use HubSpot, but couldn't they get a $25 a month Mailchimp account of their own and start sending out this communication with nice looking emails?
Rick Knudtson [00:13:46]:
Which is exactly what I did by the way, at my previous company. So go ahead. Yeah, yeah.
Omer Khan [00:13:52]:
So there was clearly a bigger pain behind that. It wasn't as easy to solve. So how did you figure out what that pain was?
Rick Knudtson [00:14:03]:
So to be totally honest, like the first year of the company, we really started the company in January of 21.
Omer Khan [00:14:09]:
And.
Rick Knudtson [00:14:11]:
Yeah, this is maybe a fun, fun stories about how we even got to our first customer and all this kind of stuff. But the that that year I was in your camp, I was like, email, this is not that hard. Like you guys can't actually have this problem.
Rick Knudtson [00:14:23]:
So we kind of ignored the noise of this email thing that kept coming up. And in fact, I would argue that we had a little bit of an ego coming off of a successful exit and you know, believing that like, let's build something interesting and novel in this space. Like, and clearly email is not sexy.
Rick Knudtson [00:14:38]:
You can't build that. So we really ignored it for the first six to nine months while we kept hearing that problem come up for all the reasons you just said, like, clearly the Mailchimp can just do that. It's cheap, it's easy to do. I used it in my previous company.
Rick Knudtson [00:14:52]:
But then the one thing that I hadn't experienced though is really working at a large company, like a real large company. Largest company I'd worked at before I was acquired at that previous one was my own, which was a 200 employee company.
Rick Knudtson [00:15:04]:
And of course, once you reach 1,000 employees or 10,000 employees, or Workshop's largest customer today is Capgemini of 400,000 global employees, it's a very different problem.
Rick Knudtson [00:15:16]:
And once we dug into it, one of the big challenges are one, if you use an off the shelf tool like Mailchimp, you're going to end up in spam boxes and it just doesn't reach employees because there's so many security layers inside of these organizations that you have to really work with their IT teams to make sure that you can get through to the employees.
Rick Knudtson [00:15:34]:
Right. Meanwhile, still doing everything on brand and having beautiful visuals, which means you got to have the ability to download images and it gets there in inboxes really quickly. Like all of these things are real challenges that external marketing tools aren't built for because there's this kind of really tight governance in these enterprises.
Rick Knudtson [00:15:54]:
So once we really understood that, yes, the visuals are interesting and we got to solve those problems, but really the real challenge is governance around how do we use this tool at a real large enterprise where we have expectations on security levels.
Rick Knudtson [00:16:09]:
Also, just sending to 100,000 employees and getting an important message into their inbox in minutes is really, really challenging as you go through their email servers. So there's some infrastructure stuff that we had to build, like all sorts of really technical things that off the shelf tools like Mailchimp just aren't built for.
Rick Knudtson [00:16:28]:
So that's what we had to discover with more conversations. We kept asking why? Why is this a problem? Why haven't you used Mailchimp? Why can't you use your marketing tool? You have Marketo or whatever the tool is, and once you peel it back, you realize there's some really complex technical problems that we could solve.
Omer Khan [00:16:46]:
If you're looking more upmarket. Some of these bigger customers, didn't they already have some kind of tool for all the other stuff like the intranet and for other types of communication? And wasn't email kind of a feature sitting in this product somewhere?
Rick Knudtson [00:17:04]:
Yeah, to an extent. I mean, I think that what we see in today's market is there are what I would describe as destinations for employees. These are like the intranets, the mobile apps that you log into. If you dig into the data of those, they're not used a lot. Engagement's really low.
Rick Knudtson [00:17:19]:
In fact, with companies that might have a mobile app with their brand and want maybe their frontline teams to log into it, they have a two part problem.
Rick Knudtson [00:17:27]:
They're like one, I got to get people to download an app on their phone and then I have to have them check it every day, which in reality is pretty tough. So the market said yes, there's these destinations.
Rick Knudtson [00:17:40]:
What we discovered is that what the market lacked was a way to take the existing channels that employees are already in and elevate them. Like let's actually make them work together better. Let's provide data and analytics into those channels. So for us it's email, it's text. So for frontline employees and then it's integrating with their existing channels.
Rick Knudtson [00:18:05]:
Slack Microsoft Teams pushing content to those platforms, but also their intranets. So the largest intranet in the enterprise is SharePoint. So we integrate with them and push content. So what we become is kind of a distribution tool. The employees don't even know that Workshop exists. The internal communication teams use it every day.
Rick Knudtson [00:18:25]:
The department heads, the leaders, the executives. But what we're trying to do is actually leverage the existing channels and reach those employees in those channels, but provide visibility for those that are actually doing the communications. Which is kind of the only platform in market that does that is Workshop.
Omer Khan [00:18:39]:
Got it. Great. Tell me about the first customer. Who was that? If you can tell us. And how did you, how did you land them?
Rick Knudtson [00:18:48]:
First customer? Yeah. So in the early days I'm a firm believer in like before you sell anything, you have to be marketing for a year. So we kind of on day one built a newsletter. So we called the Happy Monday Club. Today it has 50,000 subscribers today. At the time it had zero.
Rick Knudtson [00:19:08]:
So we were like starting from nothing. But the idea was actually just to build a weekly newsletter that provided kind of an optimistic view of HR, which if you follow a bunch of HR stuff, it tends to be pretty negative. We're like, actually you can be impactful in employees lives.
Rick Knudtson [00:19:24]:
So we kind of had this very optimistic point of view in the market. So we built this newsletter. That's where we sourced a lot of our early prospects. So how did the newsletter get shared?
Rick Knudtson [00:19:33]:
Well, lots of our own social networks at the time and all sorts of things and Then trying to do co branded opportunities with other resources in our market. So think of other newsletters or people running communities as an example.
Rick Knudtson [00:19:49]:
And that's where we found our first real non affiliated customers as I call them, the people you can't text these people, they're not friends of yours.
Rick Knudtson [00:19:57]:
But I will say our best partner was a local Nebraska company that it's a company called Hudl and they, they're a big sports tech company so they do like film analysis for every college team. It's a pretty cool technology company here in Nebraska and they're about 1500 employees.
Rick Knudtson [00:20:18]:
I think they have 4000 folks that are global doing other more analytical data work in India and the Philippines. So they have this kind of complicated organizational structure. They felt like a perfect fit for like a beta customer to really understand the problems they had.
Rick Knudtson [00:20:37]:
So they worked with us pretty closely in the first year as like almost a design partner didn't pay us any money. And we just kind of learned a lot about their process.
Rick Knudtson [00:20:46]:
And then if you really want to like think about the first real customers, like we, as we iterated on our product, as I mentioned, we were building an intranet for about six months. Like we thought that was going to be the thing. And we just kept getting feedback.
Rick Knudtson [00:20:58]:
They're like, yeah, but the email, I got to solve the email. So it was September of 21 where we decided to actually kind of rebuild the platform and solve this email thing because we weren't really finding a lot of traction with the intranet product.
Rick Knudtson [00:21:09]:
And I think that the reason for that is there's so much to build with intranets that you probably could get there, but it's going to take you a long time. You can't build an iterative intranet product. Right?
Rick Knudtson [00:21:19]:
But if I could build a solve for the email analytics and start there, then I can kind of build this iterative product for what we've built over the last five years. So we shifted towards this email product and it was pretty amazing.
Rick Knudtson [00:21:35]:
After talking to customers and prospects and trying to sell this thing every day for nine months, this intranet and then hearing this feedback about email, we finally just emailed. Everyone said, hey, we're going to do the email thing. Is anybody interested in that?
Rick Knudtson [00:21:47]:
And we had all these hands raised up and it took us about nine months to maybe earn three customers on the intranet. It took us 30 days to get 10 customers on the email product. So we knew immediately that like, okay, this resonates.
Rick Knudtson [00:22:00]:
We're going to go all in on this thing and that was Q4 of that first year we were in business. So it took us about 12 months to really land what people probably would call product market fit, where it was like, obviously we have something. Let's go all in on this thing.
Rick Knudtson [00:22:12]:
And that's what we've been doing since,.
Omer Khan [00:22:14]:
You know, that's not the first time I've heard a founder say something like that. Where you're talking to customers, you're trying to figure out what their pains are and you have this idea of this product that you're going to build and they keep telling you something else and.
Rick Knudtson [00:22:30]:
You're like, yeah, yeah, I'm way smarter than you. Yeah. You know what I mean? Yeah.
Omer Khan [00:22:35]:
And then in hindsight, when you look back after a while, you're like, but they were telling us that over and over and over again.
Rick Knudtson [00:22:40]:
Yeah, we actually, through that experience, one of our core values is listen to learn. And that was literally from that first 12 months where it's like, leave the egos at the door. Your customers are always right. They're just going to tell you what to build. And we still talk about that every day.
Rick Knudtson [00:22:54]:
Because I think that a lot of I'm guilty of this, especially coming off again a successful exit, you're like, well, this is going to be easy. It's a very humbling experience because it's just as hard the next time. And you assume a lot about what you did previously will work.
Rick Knudtson [00:23:08]:
And one of the things we had to learn was actually just shut up and listen. They're going to tell you what you need to know. So that's exactly what we did.
Omer Khan [00:23:16]:
Okay, great. So you've got the newsletter, you spent about a year marketing, so you've got an audience there that helps you get some initial customers. How did you go about what else did you try to reach customers? Was it mostly the newsletter or did you have to look elsewhere to get to say the first million in ARR.
Rick Knudtson [00:23:37]:
In the hosting industry? So this is just my background as almost like a marketer I guess in the hosting industry. It's almost a consumer industry. It's prosumer, I guess you might call it.
Rick Knudtson [00:23:46]:
So it's a lot of self service, it's a lot of inbound marketing, you know, so we took a lot of like what we learned at my previous company and I'm a, I'm a huge proponent of inbound marketing. It's like I just don't think you can scale a business as quickly as you'd want to.
Rick Knudtson [00:23:59]:
Just doing outbound, like it's like you Got. You have to have people show up at your door and ask to pay you. So we spent the first year of the business building what I would describe as a community, you know, so.
Rick Knudtson [00:24:10]:
And really laying the foundation for what we knew would probably, if we found success, become kind of the seeds of a CRM filled with leads that I could then maybe put a sales team on. So the first year was the newsletter. We did that. And we did that consistently every week. We still do it every week.
Rick Knudtson [00:24:27]:
We've done it for five years. Then we also, if you go to our website, you go to the resources tab. I think that the playbook's pretty obvious, but it used to be that 15, 10 years ago, you would do a bunch of free ebooks and you download ebooks and those become the leads.
Rick Knudtson [00:24:41]:
And we kind of adopted this idea of like, yes, we want to provide free resources, but let's not gate the content, let's just actually provide the solution. So if you look at the resources, we built this resource library to help communicators solve the problem they have today.
Rick Knudtson [00:24:54]:
Not write about it, but say, hey, I know you want an internal comms calendar. We built it. I know you want to understand how you benchmark against the industry. Here's the benchmarks report. It has all the information on how you benchmark.
Rick Knudtson [00:25:05]:
So we've built kind of a really robust inbound engine through just providing resources to the market based off of what we know long tail SEO looks like. So you do a bunch of research on what are people looking for. Let's solve the problem. Fill the gap. Fill the gap.
Rick Knudtson [00:25:22]:
And if you do that consistently for 12 months and you wake up at the end of the year and you have 50 resources all doing long tail SEO, you have a lot of inbound leads coming in. And that was the seed for, I think, scale and, and I'd encourage any founder to do that.
Rick Knudtson [00:25:38]:
It's like, you're not going to be mad that you started marketing 12 months ago. Trust me, like, you're going to be happy you did. And that's been kind of the, obviously what's propelled us forward.
Rick Knudtson [00:25:48]:
And I can speak to like, I will say that once we hit a million of ARR, it becomes more about like, okay, cool, how do you build a repeatable sales process? Like, how do you get out of founder sales? How do you train salespeople?
Rick Knudtson [00:26:01]:
Another thing we've done, and I'm, it's funny because it's 2026, so it's like, is it still work? And webinars, they work we do a webinar every month, sometimes two. When we started that, we did that in the first year as well as part of the resource strategy.
Rick Knudtson [00:26:17]:
And I think we had five people show up to the first one. Our Last one had 500 people show up to it. So it's something that we've just been committed to every single week.
Rick Knudtson [00:26:26]:
And the way you do that is you invite other people on that are wasteful, smarter than you, that are in the industry, that have an audience so you can co market and that's how you build an audience. And we've done that consistently.
Rick Knudtson [00:26:36]:
So any software business I'd highly encourage, you can't try it once and say, man, it didn't work. You literally have to do it for a year and you'll see a lot of progress. So we still do webinars. It's a big piece of it.
Omer Khan [00:26:47]:
So I've heard a lot of founders say, I want to create content, but I'm not an expert. And in your situation, you were creating a newsletter for comms people, HR people, but that wasn't your background. So how did you think about the.
Omer Khan [00:27:07]:
What was like the content strategy that helped you figure out something useful to put in that newsletter every Monday?
Rick Knudtson [00:27:17]:
Yeah, great question. It's like imposter syndrome, where you're like, am I able to be the expert in industry? And I will say that like our head of marketing, our CMO, Jamie Bell, who I was able to convince to come from Flywheel to here, she's super talented. Like, she's, she's number one.
Rick Knudtson [00:27:33]:
It's content like for her, you know, so, so this is kind of like right in her wheelhouse. And her and I would have conversations the early days exactly about this, which is like, can we really like be the one that just like writes and tells people we don't even work at a thousand employee company.
Rick Knudtson [00:27:45]:
We're going to convince 5,000. But what you do though is you talk to a lot of people. You know, like, I think we learned a lot.
Rick Knudtson [00:27:51]:
Like we, we operated in the first 12 months while we were selling kind of a beta product, which by the way was the intranet for a while and kind of became other things was we, we operated as if we were selling.
Rick Knudtson [00:28:03]:
So we'd get on calls every day, we'd try to convince people to take these calls, we'd do demos and obviously for us, you know, we weren't selling a lot reminder. So like it was, it was more of a learning experience, which is just like, let's listen to customers and you Learn a lot about what your customers need.
Rick Knudtson [00:28:19]:
You got to convert that into content strategy.
Rick Knudtson [00:28:22]:
So I think that no different than product where we're trying to understand what features will solve these problems, I think that all of that can be parlayed into a content strategy where maybe you weren't an expert before, but after you talk to 100 people, you become an expert because you have actually probably more perspective than they do in their single point of view because you've spoken to so many people in your industry.
Rick Knudtson [00:28:43]:
And I think any company can do that. So that's definitely how I feel comfortable with it.
Rick Knudtson [00:28:47]:
And you just take a lot of these little nuggets of information where if every conversation for us, you hear people say, hey, I try to plan out my content over some time frame and I'm still doing it in Excel and it's kind of a pain. And you hear that a lot.
Rick Knudtson [00:29:03]:
I'm like, well, let's just build a better calendar, let's do that. So we built the content calendar. So that's kind of where the content strategy came from in the early days.
Omer Khan [00:29:10]:
You see, I really like what you said earlier about having a mission before you were even had to figure out what the product was. And I should caveat that by saying when I was in the corporate world, when I was at Microsoft and people talk about mission statements, I'd been there long enough just to roll my eyes.
Rick Knudtson [00:29:29]:
It was like, oh, here we go again.
Omer Khan [00:29:31]:
But I'm guessing that as a second time founder, that was an intentional thing you did. And now I can see how that helps.
Omer Khan [00:29:42]:
Where even if you don't know exactly what the product is or is going to be or what you're going to sell, if you have that mission about who you're helping and what big problem you're trying to help with, that in many ways can be enough just to keep you driving ahead with the newsletter with webinars, whatever it is you want to do while you figure out what that product is.
Omer Khan [00:30:07]:
And so I'm curious if there was anything else like that as a second time founder you did differently that helped you in that maybe that first year or so.
Rick Knudtson [00:30:19]:
Yeah, the big one was the mission. I think that I imagine a lot of people listening that like you said, have worked at big companies. It's like the mission statements kind of like, yeah, here we go. And it's like the values on the wall, super cool. And I think that's pretty common.
Rick Knudtson [00:30:35]:
And I felt like actually my previous company, it felt a little bit more like that, which was like The. I think they're a little bit more symbolic, very aspirational, and very generic. But what I found at that company was that if you just waited a while, you understood what the company really cared about.
Rick Knudtson [00:30:57]:
And there were things that we had at Flywheel that kind of became unwritten values organically by the end of the company, where we talk more about this thing than we do our own values. One example of this was this idea of optimism as a trait we hire for.
Rick Knudtson [00:31:18]:
We didn't have a core value at Flywheel that was anything about optimism, but I would say we talked more about that in the hiring process than anything else. And I could go down a rabbit hole of why we care about optimism people.
Rick Knudtson [00:31:28]:
So one thing I did at Workshop was like, we didn't write any values for a while. We literally, for the first year, just said, hey, we have a mission statement. We kind of know that we're working towards this idea that we want to help companies create better cultures. We think it can be done via better communication.
Rick Knudtson [00:31:46]:
But to your point, what's cool about a broad enough mission is that it says nothing about what you're doing, actually. It doesn't say we're building software. It doesn't even say that we're going to sell software ever. But we have to be technical, so it's probably going to be software.
Rick Knudtson [00:32:00]:
But it also helps other teams provide value as well. Because to your point, the resources roll up right to the mission. We run a conference. It's actually about a month from now. We decided to run our own internal communications conference. It's here in Omaha, but we've got 200 people here this year, which is super exciting.
Rick Knudtson [00:32:17]:
But that's a great example of another thing that rolls right up to the mission. It's like, how do we build a community for folks to get connected with each other? We break even on it. We don't make any money on the thing, but it's really core to our mission of helping these organizations.
Rick Knudtson [00:32:30]:
And then, oh, by the way, hopefully someday they build our software or buy our software. That's kind of the end goal. But one of the things that we pulled from the previous company was, let's just wait to write the values.
Rick Knudtson [00:32:41]:
And I will say that first 12 months was really challenging for the Workshop team, the early founding team. The core values were so much more meaningful when we wrote them 12 months in, because we knew why we had even survived that long. So being able to then say, here's why we were successful.
Rick Knudtson [00:32:57]:
Here's the things that made the hard times Possible to just get up and do the work again. And then what you realize is that there's gonna be a team in your company someday. That what you want to try to do is infuse a lot of that early energy and perspective into because they're leading some cool strategy.
Rick Knudtson [00:33:19]:
But what they need to be able to do is run autonomously. So they're going to ask questions about, how do I make this decision today? What would the founding team do? I don't know. So the values should serve as ways where they can get a little bit out of the maze of decision making.
Rick Knudtson [00:33:36]:
Because what do we do? We move fast. We listen to customers. The customer's always right. We hire super optimistic people, and then kind of go on the list of like, okay, this is how I would really approach this product problem. And then I could talk more about, like, you know, we.
Rick Knudtson [00:33:50]:
All the stuff we did operationally, that's a little bit different, you know, but I think culturally the values were. One thing is that we said, hey, let's. Let's give it 12 months. We're going to learn a lot. And they become way more powerful and I think more meaningful for the leadership team.
Omer Khan [00:34:01]:
Like the example you gave about listen to customers more when they tell you about email.
Rick Knudtson [00:34:06]:
100%. Yep. And the optimism thing, you know, we. One of our core values is look on the bright side.
Omer Khan [00:34:11]:
And.
Rick Knudtson [00:34:13]:
And that's from, like, years of. I've hired and interviewed a lot of people, and what I find is if you can. If you can put a bunch of optimistic people in. And the way I described it is like, we don't. Being optimistic doesn't mean you ignore problems. It means that you believe there's a solution to it. Right.
Rick Knudtson [00:34:31]:
And for me, that's like a very important trait of early employees.
Omer Khan [00:34:36]:
Right.
Rick Knudtson [00:34:36]:
Which is like, there's a big customer problem or something that we could solve for them. The last thing you want is someone in the room being like, man, that sounds like a lot of work. Oh, that means I got to do this, this and that. Like, man, that's a pain in the ass. You don't want that.
Rick Knudtson [00:34:48]:
What you want is actually, man, that would be awesome. If we could solve that problem, I think we could do it. That's what you want. So optimism is one example also where through many, many years of hiring and stuff, I've learned that if I could hire optimistic people, that's half the battle.
Rick Knudtson [00:35:03]:
So it became really core to our values.
Omer Khan [00:35:05]:
Yeah, that's awesome. Let's talk a little bit about pricing. I didn't see actual numbers on your website, but I think the model that you have is you're charging is it per organization as opposed to per seat or users or that type of thing?
Rick Knudtson [00:35:25]:
Yeah, so we kind of, yeah, there's no user based receipt based pricing. With Workshop we kind of charge by audience size. So like how many employees you're trying to communicate to.
Rick Knudtson [00:35:34]:
And then there's kind of also a layer of what channels did you purchase, you know, so if you're sending out email only, it's a price, but it's an additional cost if you want to do SMS or other channels. So those two things kind of drive pricing for the most part.
Omer Khan [00:35:47]:
Yeah. And was that something that you changed recently or has it been like that since launch?
Rick Knudtson [00:35:55]:
Yeah, so we never had it as a main driver. So it was always audience based. And then we had a high limit on number of users you could have on the platform. And then we, we for a while did charge for additional users past a certain.
Rick Knudtson [00:36:08]:
And the idea there was that let's use our customer success and account management team to convince them to add other departments into the organization into the platform and those would be expansion opportunities.
Rick Knudtson [00:36:20]:
What we found though is that, man, that friction, the value of Workshop and the reason you can maintain a high retention rate is like if I can get in, I could tell you that a customer of ours that would stick around probably looks like this. They have maybe they're a pretty large organization.
Rick Knudtson [00:36:36]:
They have probably five or six departments in the product using it every week. Right.
Rick Knudtson [00:36:44]:
And they also probably have a lot of automation inside of our tool running, you know, so those, those things like, and for that reason, once, once we really understood what retention looked like, we started adopting pricing that would allow us to get to higher, like get to that kind of time to value on the retention side quicker.
Rick Knudtson [00:37:01]:
So any friction that said they don't want to add users we wanted to remove, like I want to make it as easy as possible to convince them to get other departments into our platform. And then the second that you ask them to do that and they're like, well, I can't believe what it costs.
Rick Knudtson [00:37:14]:
And then we get, let's spend two weeks going to procurement. It's like a whole thing. So that's why we eliminated that eventually because what we really wanted was just as many users in the product as possible. And, and really we looked at revenue as expansion opportunities.
Rick Knudtson [00:37:26]:
More of like how do we get into other channels, how do we reach other audiences? And that's been kind of the story ever since about three Years ago, actually.
Omer Khan [00:37:33]:
I think some people listening to this might be one sort of thinking, well, you know, Rick's had this success with Flywheel and now with Workshop, and in many ways with Workshop. Yeah, I mean, he was kind of destined to do that because he had exit money.
Omer Khan [00:37:51]:
He had the network that he'd built, the credibility from that give us a taste of some of the things that those things still didn't buy you when you had to go and build a Workshop.
Rick Knudtson [00:38:04]:
Some of that is true. I think that it was never easier to raise money than our seed round in my life. And even since then, it's been hard. Every round's harder. But. So there was some truth to coming off a successful exit. I think that you could.
Rick Knudtson [00:38:21]:
And people might ask, why do you raise money when he had a successful exit? He probably capitalized the business yourself. And the one thing that I've always loved is I do like accountability from partners. One, I think that there's a lot of value in actually a team around you trying to push you forward.
Rick Knudtson [00:38:37]:
And I think investors can be very impactful in that way. So it's kind of a forcing function for velocity in a lot of ways. So I've always appreciated that.
Rick Knudtson [00:38:45]:
I will say, though, that the real story of that first 12 months of I'm just being super transparent and a little honest, is that by month nine, after we had about zero customers and we had raised, I think, $3 million out of the gates, my partners and I, I was a proponent of, like, giving the money back to investors.
Rick Knudtson [00:39:09]:
I was ready to be like, hey, this is not working out. And this is at the time when we were still hearing this email thing. Again, this is the ego at the door. But it's like, well, we got this novel idea. Let's build this interesting thing. And we just ignored it.
Rick Knudtson [00:39:21]:
And I was like, well, this isn't working out. It doesn't seem like there's something here. We still have more than half the money in the bank. Let's just give it back to investors. Let's live to fight another day. We'll build another company. We can build those relationships. And.
Rick Knudtson [00:39:35]:
And it was my co founder, Derek, our COO, who convinced myself and Ben to do the email thing. I remember the moment that we did that, which was like, we were sitting at a bar in Omaha. We were deciding what we're going to do with the company because it wasn't working out.
Rick Knudtson [00:39:47]:
And he was like, guys, just go try this one last thing. Just listen to the damn customers. So we spent the. My background's in software engineering too, and product design. So me and my CTO were primarily building the product back then, so we spent the 30 days doing that.
Rick Knudtson [00:40:04]:
So everything, every resource that I had, every relationship, all the capital couldn't solve product market fit. I can tell you that right now. And ultimately, I think just talking to more and more and more and more customers is the only way to get there.
Rick Knudtson [00:40:21]:
And then the other things that I think were kind of interesting coming from something like Flywheel to Workshop, was that probably what I took from that experience most that I think is really hard to get without seeing it, is what does a scaled operation look like? What departments exist?
Rick Knudtson [00:40:42]:
What do those roles look like in a software business? How do you build a sales process? What data should you even track? What does training look like? These are all things that you learn on the job. And the first time you.
Rick Knudtson [00:40:55]:
You can take a lot of the tenants from a successful venture, but it doesn't mean that you're selling to the same market, the same customer. The deal size is different. The sales cycle's 12 months as opposed to 12 days. So it's a very different thing.
Rick Knudtson [00:41:10]:
And there's a lot of learning, but I think you can learn a lot from the general tenets of what does an operation look like. And I think that benefited the leadership team quite a bit, to be honest, getting from point A to point B faster. But, man, we still had a ton of things to learn.
Rick Knudtson [00:41:26]:
It's like I described that first year as very humbling.
Omer Khan [00:41:31]:
Well, I appreciate your transparency. And I think if there's anyone out there listening and they're nine months in with zero customers, there's still hope.
Rick Knudtson [00:41:40]:
Yeah, trust me, there's still hope. And to be honest, I think when people ask what is a lot of it? I think if you read Internet's like, well, it's product market fit. Like, how do you even define it?
Rick Knudtson [00:41:50]:
And I think the best way I've ever seen people write about it is like you kind of know it when you see it, you know? And I think that that's exactly how it's felt every time I've been building companies.
Rick Knudtson [00:41:59]:
And you kind of see this moment where suddenly like, nothing worked and then now it's just working, you know, and you have to be like eyes wide open on when that moment happens and realize why it's working and double down on it. You know what I mean?
Rick Knudtson [00:42:12]:
I think that that is something that my core leadership team, I think is quite good at is like, being comfortable with, like, hey, this is working. Like, let's just go after that. Like, go chase it. And I will say we were blinded for a while by our own ambitions on like, what crazy cool idea we could build.
Rick Knudtson [00:42:28]:
And the second you stopped doing that and then the moment that it happened, I was like, okay, this is it. Let's build it.
Omer Khan [00:42:34]:
All right, we should wrap up. So let's get on to the lightning round and I've got five quick fire questions for you.
Rick Knudtson [00:42:40]:
Let's do it.
Omer Khan [00:42:41]:
What's one of the best pieces of business advice you received?
Rick Knudtson [00:42:45]:
Oh, this one. Because this could also be a full hour podcast. I think I'm really like, I took leadership training years and years ago at my previous company, encouraged by our investors and that sort of thing.
Rick Knudtson [00:42:57]:
And one thing that the only thing I really remember from that is them teaching this idea of like protecting your A players. So this idea of like, you know, great people get have the right to work with great people and it's your job to make sure that's true. And I hold that pretty close.
Rick Knudtson [00:43:12]:
So like, once you find amazing people, you got to protect that team. And the whole idea of like hiring slow and firing fast, I strongly believe in. And it is your job to make sure those people stick around. And they're only going to stick around if they can work with great people. So that's probably it.
Omer Khan [00:43:26]:
What book would you recommend to our audience and why?
Rick Knudtson [00:43:29]:
How many times have people recommended Shoe Dog? A lot.
Omer Khan [00:43:33]:
A few. A few.
Rick Knudtson [00:43:34]:
Okay, interesting. I was like, I'm going to do like the easiest one. That's my favorite book. So I'm actually. I love business memoirs. You know, I think they're a fun way because it's like, not just like business advice. They actually just tell their story. And I think Shoe Dog's the best example of that, which is Phil Knight.
Rick Knudtson [00:43:51]:
I also just read Bob Iger's, CEO of Disney, which is a ride of a lifetime, which is a slightly different take, more corporate, but it's like a cool story of his journey and I'd recommend that book as well.
Omer Khan [00:44:03]:
Awesome. What's the best money you've ever spent on your business?
Rick Knudtson [00:44:07]:
We do quarterly company off sites, which are expensive.
Omer Khan [00:44:12]:
Yeah. Because Your company's not 10 people these days, right?
Rick Knudtson [00:44:15]:
No, no. Yeah. It's easier in the early days. Right. In the early days you just go to a bar and you have some drinks. But yeah. So every quarter we get the company out of the office for two years days.
Rick Knudtson [00:44:27]:
We fly all our remote folks in and we spend time doing quarterly planning, basically getting realigned and in a fast Growing company. It's super important but it's incredibly expensive on paper. But it's the best money that you'll spend is getting that time out of the office. Kind of the slowdown to speed up thing.
Rick Knudtson [00:44:44]:
And I'm a huge fan of that.
Omer Khan [00:44:46]:
What's your favorite personal productivity habit?
Rick Knudtson [00:44:50]:
Man, I wish I had some. The thing I've been doing recently is I'm. I'm pretty bad at Slack. It's like so noisy and we're a Slack culture and I kind of like my email is the only thing that's sacred. So if you send me an email I might take a while to respond.
Rick Knudtson [00:45:06]:
I probably took a while to respond to you Omer, but I will respond. I manage it like a to do list.
Rick Knudtson [00:45:11]:
So recently because of Slack and the noise is I built an agent on Claude that goes through all my saved items in Slack that I might have flagged along the day and then converts those to emails, sends them to myself as to dos with a link to that Slack message because I'm way better at managing my email.
Rick Knudtson [00:45:30]:
So that's a little thing that's like changed how I use Slack in the best way and I'm far more responsive now.
Omer Khan [00:45:36]:
That's pretty cool. I did something similar. I spent a lot of time in email and using a combination of like I think Google's got this AI workspace Studio which is integrated in with your Google workspace, right? So that can handle a lot of the email.
Omer Khan [00:45:52]:
And I wrote a bunch of different prompts to categorize emails and basically move them into folders so they didn't kind of disrupt me during the day in my inbox which was great until I found myself just sitting there staring at an inbox with two emails in there and going now what? Now what? Right?
Rick Knudtson [00:46:15]:
I've been meaning to play with Studio for that reason because I think that there's some cool ways to do exactly that which get the mess out and then kind of come back to it when it matters.
Omer Khan [00:46:22]:
And finally, what's one of your most important passions outside of your work?
Rick Knudtson [00:46:25]:
I was just talking to my co founder CTO who's a new dad and he was just talking about how he has no hobbies anymore. So I have no. I work and I have a nine year old daughter. So any time outside of work that I have, I'm usually spending time with her.
Rick Knudtson [00:46:42]:
Tonight she has volleyball practice and I'll be there. That's my life. So it's like work and as much family time as possible. I used to have way more hobbies. I used to be, like, a big video game player and all sorts of cool stuff, you know, but, like.
Rick Knudtson [00:46:55]:
So I wish I had a good answer, but it's probably just like, any minute I go with my daughter. That's the passion outside of work.
Omer Khan [00:47:04]:
That's an important thing to do. And I kind of went through that. And now my kids have got to the age where they don't really want to spend time with me.
Rick Knudtson [00:47:13]:
I'm dreading that.
Omer Khan [00:47:14]:
Yeah. So I'm back in that place now where it's like, I need to get some hobbies, man.
Rick Knudtson [00:47:19]:
Well, I'll follow up with you in a few years to tell me what I need to get back into. Yeah, yeah.
Omer Khan [00:47:23]:
There you go. Awesome. Well, thank you so much for joining me. It's been a pleasure. If people want to check out Workshop, they can go to useworkshop.com and if folks want to get in touch with you, what's the best way for them to do that?
Rick Knudtson [00:47:37]:
Probably just shoot me an email. Rick at useworkshop.com. Happy to chat and also love talking with other founders. So if there's something there, happy to discuss. Anything.
Omer Khan [00:47:45]:
Thanks, man. I wish you and the team the best of success. Cheers.

Girish Redekar, Sprinto
Girish Redekar is the co-founder and CEO of Sprinto, an autonomous compliance platform that helps companies prove they're handling data securely. Before Sprinto, Girish and his co-founder spent two to three years trying to build their first startup. They had no programming background, so they taught themselves to code at 28 because they couldn't afford to hire developers. The first few ideas went nowhere. A job search engine. A resume matching tool. None of them got traction. Then they built RecruiterBox, a simple CRM for hiring. It launched before Stripe even existed, so their payment system was absurd. Customers had to click a PayPal link, swipe their card, and get credits that depleted daily. When the credits ran out, they'd go back to PayPal and swipe again. It was terrible. But customers kept doing it anyway. That was the clearest signal of finding product-market fit Girish had ever seen - not from analytics or feedback forms, but from watching people jump through hoops to keep paying. They bootstrapped RecruiterBox to over 2,500 customers and single-digit millions in ARR. Then they sold it. Not because it was failing, but because it got too comfortable. They felt like they were the bottleneck, and the business would grow faster in someone else's hands. The second time around, Girish took a completely different approach to finding product-market fit. He'd experienced the pain of SOC 2 compliance firsthand at RecruiterBox, spending months and tens of thousands of dollars on consultants. So when he started Sprinto, he made a rule - no code until the idea was validated. He used The Mom Test framework, ran 15-20 customer interviews, and then paid auditors to audit his non-existent company. Ten times. Each audit, he built a little more product behind the scenes. By the tenth, he knew exactly what to build and had confirmed the consulting service could actually become software. For go-to-market, Girish tried 20 different channels. Seventeen failed. The three that worked were founder communities (Slack groups, WhatsApp groups), VC portfolio programs with startup discounts, and Google (paid + SEO). His framework - harvest existing demand rather than create new demand - helped him focus on places where people were already looking for solutions. Now AI is changing the game from three directions at once. It's changing Sprinto's product, it's changing how customers operate internally, and it's creating new security threats from the outside. The problems that didn't exist two years ago are now driving a whole new wave of demand. Today, Sprinto generates eight-figure ARR with over 3,000 customers across 75 countries. The team has grown to 350 people and they've raised $32 million.

Sarah Ahmad, Stable
Sarah Ahmad and her co-founder Colin met freshman year of college and moved to San Francisco to work as engineers. They quit their jobs to build Mistro, a platform providing benefits for remote teams internationally. They got into Y Combinator's Winter 2020 batch, raised a pre-seed round, and had paying customers. Then COVID hit. You'd think a remote work tool would thrive when the entire world went remote. Instead, it was silent. They couldn't even give the product away for free. COVID had pressure-tested their product-market fit and exposed the truth - nobody needed what they were building. Sarah went back to basics. She ran discovery conversations with hundreds of operations managers and founders. One problem kept surfacing: companies without physical offices didn't know what to do about their business address and physical mail. The incumbents in the space had been around since the 2000s with clunky software. Nobody was raving about them. Instead of making the same mistake again - building a full product before validating demand - Sarah took a completely different approach to SaaS product validation. She posted a simple landing page in the YC community. The response was immediate. Dozens of founders emailed saying they needed it tomorrow. The first version of Stable was embarrassingly manual. A mail partner in San Francisco, Google Drive for document storage, Zoom for onboarding, and a Stripe link for payment. Sarah was manually emailing customers when mail arrived. They ran it this way for the first 100 customers before writing any code. Today, Stable is the leading AI-powered virtual mailbox for businesses with over 10,000 customers, 8-figure ARR, and a team of 50-60 people. They operate in 20+ locations across the US with processing centers in the Bay Area, New York, and Dallas. Their customers range from solopreneurs to enterprises like DoorDash, Realty Income, and GitLab. In this conversation, Sarah shares how the SEO playbook that built the business stopped working when AI overviews took over Google search results, why physical operations are her moat against AI disruption, and the moment she had to shift from product building to company building.

Joel Griffith, Browserless
Joel Griffith is a jazz trumpet player who taught himself to code. Before building his bootstrapped SaaS, he went through five or six failed B2C business ideas. Then he had a realization - the problems he understood best were the ones he dealt with every day as an engineer. The idea came from a side project. He was building a wishlist app and needed to pull product data from retail websites. That meant running a browser in the background to load pages and extract content. It was a nightmare. The browser would crash, run out of memory, and nothing worked reliably. He went to GitHub and sorted issues by most commented. They were all engineers struggling with the same thing. So he pivoted. Instead of building the wishlist app, he'd build the infrastructure to make browsers work reliably for developers. His first customer paid $200 a month. Total infrastructure cost was $50. He was profitable from day one. But growth was painfully slow. He ended his first year at about $1,000 in MRR. It took three years of working nights and weekends, writing blog posts, answering questions on forums, and building in public before he hit $500K in ARR. Even then, he waited an extra six months because COVID hit and he wanted a safety net before going full-time. He ran the business solo, getting to $60K in MRR as a one-person operation. But he eventually hit a wall - he didn't know how to hire, sell, or build a team. So he partnered with a small firm called Polychrome to handle the operational side of the business. Then AI changed everything. Joel had spent years building infrastructure for web scraping and testing. Now AI agents needed browsers to navigate websites, fill out forms, and interact with systems that don't have APIs. A whole new category of demand showed up almost overnight. Today, Browserless is approaching $4 million in ARR with a team of under 10 people. Joel has never raised a dollar. His bootstrapped SaaS survived Google Cloud and a $60M-funded competitor entering his space - his growth didn't even flinch because eight years of content and community had built something no amount of funding could replicate overnight.