PSPDFKit: Bootstrapping a SaaS $20K to $1M ARR in 8 Months – with Jonathan Rhyne [407]

PSPDFKit: Bootstrapping a SaaS: $20K to $1M ARR in 8 Months

Jonathan Rhyne is the co-founder and CEO of PSPDFKit, a software development kit that enables developers to integrate advanced PDF functionalities into their apps.

In 2014, Jonathan was working as an attorney, living with his in-laws, and about to start a family when he took a huge risk to join PSPDFKit as a co-founder.

The startup was making just $20K in monthly recurring revenue (MRR).

Jonathan and his co-founder faced the challenge of growing their business in a market where even Adobe hadn't yet solved the problem.

They immediately got to work. Jonathan overhauled their pricing, introduced a new subscription model, and focused on creating valuable content to attract developers.

The hard work paid off. In just 8 months, they grew from $20K to $1 million in annual recurring revenue (ARR) a huge win for any startup.

But their rapid growth also brought unexpected challenges.

They struggled to balance customer demands with their long-term vision, often resorting to quick fixes that risked creating technical debt and future problems

Despite their initial success, the next few years were challenging. Their attempts to launch new products didn't work out, leaving them unsure of their direction.

Growth slowed down. Market uncertainties and tight finances tested their resolve. But they persevered, steadily growing the business year after year.

Today, after overcoming numerous obstacles, their business generates multiple eight figures in revenue, with a team of 150 people across 27 countries.

In this episode, you'll learn:

  • How Jonathan made the leap from lawyer to startup founder, and why he took such a big risk.
  • What strategies Jonathan used to grow from $20K MRR to $1 million ARR in just 8 months.
  • How the founders balanced short-term customer demands with long-term product vision, and the costly mistakes they made along the way.
  • Why the transition from bootstrapped to investor-backed was eventually necessary but challenging, and how it fundamentally changed the business.
  • How PSPDFKit adapted their marketing and sales strategies over time to finally achieve sustainable growth in a competitive market.

I hope you enjoy it!

Transcript

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[00:00:00] Omer: Jonathan, welcome to the show.

[00:00:01] Jonathan: Hey, thanks for having me. Omer.

[00:00:03] Omer: Do you have a favorite quote, something that inspires or motivates you that you can share with us?

[00:00:07] Jonathan: Yeah, like, you know, I, I, I was in high school in my kind of late nineties, early two thousands, so the whole think different campaign with Apple was a huge one.

[00:00:17] So I am you know, self-proclaimed Steve Jobs fan. I'm an Apple fanboy, if you wanna call it. So you know that, that that campaign, if you, that, if you remember back to it, the end line, it is, you know, the people are crazy enough to think that they can change the one, the world are actually the ones that do.

[00:00:36] And to me that's a super, like a good reminder to be ambitious you know. Don't look for other people to do something. If you want something to change, the best way to do it, the best way to predict the future, best way to make the future is be the one going out there and trying to do it. And so I, I kind of try to live by that.

[00:00:53] I kind of try to, you know, you want to be ambitious and not unrealistic or arrogant, but at the same time, you don't wanna be under ambitious.

[00:01:01] Omer: Yeah, totally. So tell us about PSPDFKit. What does the product do? Who is it for, and what's the main problem you are helping them solve?

[00:01:11] Jonathan: Yeah. So I have to tell you kind of early days we were an iOS framework.

[00:01:15] Originally it was just done because the iPhone had came out, the iOS HDK came out and nobody could put a PDF viewer on it. So most people think like, well, doesn't Adobe do this? And now they didn't. And so there was this need for companies that were putting a magazine app for a reader on the first iPad or things like this.

[00:01:34] And we kind of saw the niche. We built it we built literally a magazine viewer with it and then kind of put it up on a store. And lo and behold, we found a need as the mobile kind of industry took off. Now if you fast forward to kind of today. We went from just being this like mobile SDK developer tool provider to much broader facet.

[00:01:54] We've bought a few companies so we have everything from, I know, developer tools for the web, every major Java framework or JavaScript framework out there to mobile, iOS, Android, you know, hybrid frameworks all the way to literally like server side libraries to do, I don't know, dot net batch processing of invoices, signing viewing.

[00:02:16] If you look at our, if you go to our website and look at our list, you'll know a lot of the customers on our list that most people are surprised. We're kind of the unknown ingredient by a lot of these apps because there isn't a huge, massive open source community that solves these problems that get you 80% of the way there.

[00:02:32] And then we kind of do the rest and, and as we've built that out. You know, we have a workflow automation tool as well as you know, kind of integrations for IT administrators and things like Salesforce and SharePoint.

[00:02:44] Omer: You know, like hearing you talk, you sound like, you know, you could just be another tech founder from the Valley.

[00:02:52] And I think many people would be surprised to know that your background before you, you, you, you know, jumped in on this business. You were an attorney.

[00:03:00] Jonathan: Yeah. And it, it's a really interesting story if you think about how I got into this business. 'cause so I started out in computer science at NC State.

[00:03:08] I was a gamer still gained to this day. Whether it's like term based strategy or first person shooters you know, I still play apex legends, things like this. And so I loved computers because I love gaming. I love competition there. And the first thing you run into is like, okay, well I need to build a website for my clan.

[00:03:23] I need to, you know, collect analytics and I need to have a database to Discip display. And so then I went to school and I quickly kind of realized like, Hey man, I don't wanna be sitting by behind a computer all day long. But I had two years of a CS degree. I pivoted to political science. I then, you know, was very much adamant, like, okay, I need to go to grad school.

[00:03:42] I'm trying to raise a family. Things like this. Law law really appealed to me. I went to law school. I love law school. And I came out in 2009. It was like the worst period of time ever to come out of or law school. Kind of like today is like, you know, you're seeing people get laid off in the tech space that was the legal field in 2009 or 2008, 2009.

[00:04:03] And so the iPhone SDK had just come out. My brother was at a government contracting agency and he was a huge Apple fanboy way before it was cool to be an Apple fanboy. Like he was a Mac developer, like we're talking about a dinosaur here. And so he was starting a mobile agency and going to these conferences and I kind of was like, Hey, you know, who's, who's at these conferences?

[00:04:25] And I was just trying, I was literally working at Sears, selling appliances, doing the exact same job I had in high school, living at my mother's house. I had two degrees and a license to practice law. So you can imagine the mind space I was in and still I was like, you know, I just, I gotta find, you know, gotta find a way to break through.

[00:04:41] I gotta make this a positive. So I started going to these conferences he went to because the attorneys that were showing up were all pet controls. They're patent attorneys trying to get people to file patents for software. And a lot of these indie developers were essentially, you know, I'm starting a business.

[00:04:57] I've never been a business owner. Now I got a contract in front of me, or I need to register a trademark, or I need to incorporate my business. And they, you know, I just kind of was like, well, hey, I know about software, I can negotiate that contract. So I started getting talks about it. I kind of became known as the iPhone attorney guy.

[00:05:15] And I just started, you know, building a practice in that space. And yeah, lo and behold, as my legal career went off and I started to litigation practice I got to the point where I met Peter and I had an opportunity. Peter's my co-founder, Peter Steinberger. I had an opportunity where he was in a place where he became a client of mine.

[00:05:32] The company became a client of mine. And they basically were, he was like, Hey man, I don't want to deal with all this stuff. Can you just do it? It was kind of like, well, well I can't, I can show you the doors. I can't open 'em for you. I'm your attorney. I'm not, like, I can't make decisions for you. And so the early days that happened in 2008, 2009, the early kind of, you know, sales career, I had the early kind of gaming career had all kind of came together beautifully for this opportunity when we started this business.

[00:06:01] Omer: So I want to talk about how, how you, you, you kind of joined 'cause you didn't, you didn't join at Zero, you joined at 0.02. We'll talk about that. But before we get into that, give us a sense of the size of the business. Where are you today in terms of revenue, number of customers, size of team, so on?

[00:06:20] Jonathan: Yeah, I, I won't give exact numbers on revenue, but I mean, I would say we're about a series D.

[00:06:25] When I say that, I mean we're in the multiple eight figures of revenue. You know, we're still growing fairly rapidly. We've done some organic and, you know, inorganic growth, we bought a couple of companies. We're around 150 people. We're in about 27 different countries. Out of those we're fully remote.

[00:06:44] So we're kind of, we have this bit where we were headquartered in Europe, in Vienna, Austria, and kind of headquartered outta Raleigh, North Carolina because that's where Peter sat and that's where I sat. And our other business partner, Martin Sher, was over there as well.

[00:06:56] Omer: You, you guys have raised I think about a hundred million euros to date which is through private equity.

[00:07:05] But the really interesting thing about your business is, and I had no idea until you told me just, just a few minutes ago, was that you were bootstrapped until you guys were about 12 million in a RR.

[00:07:21] Jonathan: That's correct. Feel lucky. And so one of the things, I think it's very rare that you go down this path.

[00:07:28] I think it's very rare that you're in a market that you can survive going down this path. I mean but we grew a sustainable business. We were profitable, I mean, very early, other than paying ourselves. We paid ourselves through the profits, but I mean, we didn't take on debt debt in Europe, debt, especially in Germany and Germanic countries.

[00:07:48] It's kind of like a four letter word I like to say, you know, like they just don't do it. So we had to grow by getting the next customer and then thinking smartly about how are we gonna invest this money back in the company? How are we gonna grow? You know, and, and, and how do we get in a place where we don't have to, Hey man, we can't afford to pay you anymore.

[00:08:08] You're really great. You're really awesome. I just don't have the capital to do it. And we're lucky that we were able to do that and. Yeah. The market changed in Covid so we got interest along the way. We had probably, we talked to about four to five companies, some of them very large strategics that people know that wanted to buy us in the early days.

[00:08:29] But we kind of just wanted to continue doing what we're doing. And then we reached, you know, you reached that seven, eight year mark. And I think, you know, some people. You know, they've, they've run out of outta steam. They're ready for a break, get burnout, you know, and you're looking for a change.

[00:08:45] And Covid was super, super, like we already had a growing business and then Covid was an accelerator of like remote hybrid work, which is essentially what we were helping companies do. And so it was a good time. Multiples were great in 21 as well, and so it kind of made sense to look for a raise. My two business partners wanted to exit you know, see how we could do that.

[00:09:07] And it, it kind of played out. And, and that was, you know, two and a half years ago and we've had some rapid growth.

[00:09:15] Omer: So you, you, you talked about, you know Peter being a client of yours but at what point did you actually, you know, jump on board and actually become and be considered a another, you know, co-founder in this business?

[00:09:27] Jonathan: Yeah, so when I met Peter, it was just him running the business. He would pull in a part-time contractor if he needed like a design work or something like this. I think what the classic you know, you try to, if you have money and you can get thing, get people that are better than you, that doing the things you're not good at, you try to do it, you know, cheap, and if you can't, you do it yourself.

[00:09:48] And that was kind of where Peter was at. But Peter was very much a, you know, an engineer. He was the technical founder. He was, he enjoyed being in the code. He enjoyed, that's what he wanted to do all day. And he met me and I was kind of the business sales, everything else person. I was at a law firm.

[00:10:06] I was on a partnership track. I was living with my in-laws. We were buying our first house and my wife was pregnant with our first child.

[00:10:13] Omer: The perfect time to join a startup.

[00:10:15] Jonathan: It was, it was a little crazy. But yeah, so we met they became a client of mine and that kind of gave me a good insight as to like, what, what is going on here?

[00:10:25] What, what, what action here? Where do I think I could actually make an impact? Do I think I can scale this? Not just from, you know, we, we just, we just had a web store up and there wasn't a lot of segmentation and there was a lot of stuff for me that I kind of looked and said, I, I, I can, I can add a lot to this if I get involved here.

[00:10:47] And he kind of got to a point where he was like, Hey, I'm, I'm sick of dealing with the business side of it. I'm also ready to have a partner to kind of go on this journey with me and let's start, let's start actually, you know, investing this money. And I think we're large enough. And so, yeah, you know, it worked out.

[00:11:04] He was a client of mine for three months and then I decided, Hey, let me come on at night for three months now. I'll work, I'll work at the law firm during the day. I'll work at night helping out, let's, you know, you're 4,500 miles away from you. Let's get to know each other. Let's see what we can do together.

[00:11:20] And if it works out, we'll do it. And about three weeks into that. That three months I was, it was clear. We got along very well. We complimented each other, we trusted each other, and we saw, we literally saw some really great returns in that first year of me joining just in doing some structural changes to the business model.

[00:11:42] Omer: You basically leapt off the cliff, right? You, you are, you're in a really great job. You've got all of these things going on in your personal life. Sure you can see this business and you, you, you connect with a co-founder who, who you guys get, you know, the two of you get on with each other, but the business is not doing a lot of money.

[00:12:07] It's like 20K MRR and bootstrapped. It's not like, yeah, we've just raised this ton of money and don't worry about it. You're good for, we've got a two, three year runway or whatever. So it was a pretty big risk, wasn't it?

[00:12:20] Jonathan: Yeah, and I mean, to be fair to Peter, it was a pretty big risk, what he gave up for me to come on as well.

[00:12:27] Like he owned a hundred percent of the business, so he had to incentivize me as well. And kind of if this goes well, and I think if I hadn't joined at that time, I don't think the incentive I got and the outcome I got would've been there as well. So yeah, like but the other side of it was you had to look at what I was doing personally.

[00:12:45] My brother was. Could be anywhere. He had an internet connection in an airport because he was remote and he was going to New York and consulting. I mean, he did mobile apps for Obamacare for America, did mobile apps for Whole Foods. It's like really big stuff. And here I was, I had a license to practice in Virginia and I had a license to practice in North Carolina, and that seemed really small towny to me.

[00:13:07] It wasn't ambitious enough. My family likes to say, my brother likes to say, you're kind of like a cat with nine lives. Like if you get thrown off the porch, you somehow land on your feet. And so I do have a high risk tolerance. But I also really saw like an opportunity in the business. I saw a vision in it.

[00:13:26] I mean, listen, I still see the vision in it to be frank. And so why not back yourself and to me you know, if you're gonna start a, if you're gonna start a startup. You gotta have a little bit of that. 'cause if you don't go get a job somewhere, now there's ways to like mitigate that. Like I tell people all the time, you know, it's the same way Peter started when he did it.

[00:13:50] He was waiting for his visa to go work in Silicon Valley and he did a consulting job that he retained the IP to the, the framework that he built. And so like, if you can do this kind of part-time thing, it can kind of work, like work your nights and weekends to build your side project and try to do it.

[00:14:08] That's a great way to do it. But at some point you got a decision like you gotta go for broke and yeah. And you, you might fail and you gotta get back up and go for broke again. And I would say the earlier you do it, the better. I mean, if I have three kids now, there's no way I would've been able to do it with three kids.

[00:14:25] Like there's no way I would've been able to take that risk.

[00:14:27] Omer: So I think it was 20, around 2014, I. That you joined, is that right?

[00:14:32] Jonathan: That's correct.

[00:14:32] Omer: So 20K MRR. And then roughly how long did it take to get to the first million in ARR?

[00:14:39] Jonathan: This is a, this is a good and bad story. It probably took us from 250 k around eight months to get to a million.

[00:14:48] Omer: All right. Let's unpack that. Like what you, you obviously did something, or at least that change happened, or the trajectory change when you joined the business and teamed up with Peter. What did you do? Let, let's talk about this first, first couple of months. What did you start doing to, to drive growth and, and how did you figure out where to, where to focus?

[00:15:15] Jonathan: The first thing I did was we had a web store. We had a product led growth strategy, you know, where people came to it. And then we literally had this one. You know what the common contact us is now, and it was if your company's behind a paywall or you know, you have a login, you know, contact us and you need a different license.

[00:15:38] And we weren't on a subscription either. You gotta remember 2014 there was no such thing, like Adobe had just gone to subscriptions. And so I kind of looked and said, A, we're gonna go to subscriptions. And there are customers that, you know, canceled were done. BI looked and said, we're gonna take down this one stop pricing.

[00:15:58] Because, and this worked for our business because you gotta understand we had large companies like a Dropbox that was contacting us to do this for file previewing. And then we had, I don't know, the college student trying to get their mobile app or the indie developer trying to get their mobile app.

[00:16:16] Well, I couldn't charge that same price to both. I'm providing a different value to each. So I early on became the first salesperson. And you charge different prices. So instead of charging, I don't know, five Yeah, whatever, even if it's like a per user thing, 15 per user, you know, go bespoke. And I think a lot of these small SaaS startups, because they're technically, you know, they're technical founded, a lot of technical founders are allergic to that they don't like, you know, I want, I want.

[00:16:47] Transparent pricing upfront and, you know, you're, you're facetious or you, you know, you're doing something dirty if you don't have that.

[00:16:54] Omer: Yeah. So just to clarify, Jonathan, your target customer at the time in that first year, was that primarily iOS developers?

[00:17:03] Jonathan: Yes. And this was a space where both me and Peter kind of came from.

[00:17:07] Omer: Right. And so, so what was the model that developers were used to in terms of licensing these types of, you know, kits?

[00:17:18] Jonathan: So with each app store, there's something called a bundle id. It's a reverse URL, I'd like to call it like an address. So whatever your address is for your app. So at the time, like if you had one app on the main public store and then you had an app and enterprise store, those were two separate apps.

[00:17:34] Right. And unlike, you know, Android, they, there was no side carding, so like, it wasn't like you were able to load an instance of another app in another app. So we quickly went to, you know, per app, like it was a per app basis. But we were also pretty flexible on the business model. This was another thing I changed.

[00:17:54] So like some early customers that were just starting up, we would take a revenue share and essentially we wouldn't get paid that much, but then over periods of time it scaled like crazy and those became great deals for us. So we kind of sure rate not just like one metric, but like, I don't know, any metric you can think of that worked to close the deal.

[00:18:14] We're kind of, you know, we, we've been dealing with the cleanup of that basically since, but in the early days, you know that, that is very true. You kind of do the best deal that gets the customer up and running. That is kind of the win-win for your business and we win-win for your customer. And so that was kind of what we did.

[00:18:31] And yeah, and I space, the good thing about it in those early mobile days is you had indie developers and it was growing very rapidly growing. And you had some really large corporations that were just trying to figure out how to have a mobile presence. And so the horizontal of the framework, I mean, we're like, digital paper if you think about it is huge.

[00:18:52] And so we were in a lot of different industries pretty early on and a lot of different use cases. And, and some of those were large deals and some of those were, you know, tiny deals like, yeah.

[00:19:04] Omer: Yeah. Okay, great. So there's, there's, there's a broad demand. You switch to a subscription model for. Licensing your, your kit.

[00:19:16] Jonathan: Per year, actually even paid up front per year, not even monthly.

[00:19:20] Omer: So that's one thing. You, you, you're effectively, hopefully, you know, increasing revenue there, but what were you doing to acquire more customers?

[00:19:30] Jonathan: Yeah. And this is I like to talk about like, one of the things that I think early days when you're the first two or three people at a company, you have multiple jobs, you gotta do everything.

[00:19:41] There is no, and I mean, every founder knows this. They feel it. They like now some people choose not to do some stuff. One of the things that we had really well in our, you know, my three co-founders or the two other co-founders myself, is like, we would talk about what we were doing. We would like literally every single day.

[00:20:01] Right on Twitter. That was how we recruited. So it was like we needed people to know about us. If we wanted to get talent, we needed people to know about us so that they knew what our product was. We talked at conferences 'cause we were already connected to the conference scene, so we would talk about what we were doing before we give a conference talk.

[00:20:18] And then the thing I think that was really interesting was that the type of content that we were producing there's kind of two things I believe in, but one is like people want helpful content. Help them out with something. So I just told you a piece of content that sends, I don't know, 13,000 people a month to our website.

[00:20:37] What is a bundle id? It has nothing to do with PDFs or, you know, documents or anything like this. It literally just, if you're an I in Iowa space, people Google, I don't know what a bundle id. And they find a blog post Who wrote about it? We wrote about like 2015 or something like that. So we just started producing content.

[00:20:56] All of us. Peter, I mean, literally Peter wrote almost like a blog about a problem. He ran into, you know, swizzle doing like, you know, things that were really pertinent that were catnip for an iOS developer. And so what what was crazy is like, you know, three years later we went to dub dub by Apple's Developers conference, and you would be in a line waiting to go into the, you know, the keynote.

[00:21:25] And I bet every other developer there knew who we were. They knew who our company was by the, by our T-shirt. And listen, our company's name is P-S-P-D-F Kit. Like, it's not this beautifully named a company, but so people knew it because they had read our blog and they had found something interesting, or they had followed Peter on Twitter or they had saw a conference I was at.

[00:21:47] And so I think that just giving back to the community, giving back to where your ICP is. And especially in developer marketing and genuinely doing that, like not, not fake doing it really, really buys you a lot of credibility. It buys you a lot of awareness. It buys you a lot of referrals. It also helps you with SEO because if people are reading it and searching for things, well now when you put out something pertinent to your space while all sudden in your domain authority and Google's, you know, huge because you have all these people visiting your, your website and spending you three minutes to five minutes to visit on your website reading an article.

[00:22:24] So kind of work both ways.

[00:22:25] Omer: Yeah, yeah. I totally, so, so going go, going from the 20, like 250K in ARR to basically for Xing that to getting to the first million. You said eight months. And then, so what I heard was you, you changed basically the business model and, and how you were pricing the product to, you started, or you all, all of you were writing content and, you know, publishing and, and trying to get index and, and generate more organic search traffic.

[00:22:58] And then thirdly, you guys were building basically in public, you're using Twitter and, and just trying to raise visibility of what you guys were doing as founders and, and how you were going about building this, this business. Were those the three main things that drove the growth and helped you get to the

[00:23:16] Jonathan: Yeah, and the one, the, the fourth one I would put in there, and you're gonna get some bias from me because I'm from the, the business side of the business, right?

[00:23:25] Don't get me wrong, I was heavily involved in the product direction. But I think the other thing we did was when we built something new. That we knew was a value to a customer, a current customer of ours, did we just include it or did we charge 'em for it? So you have to create this segmentation and it can't be, you know, I don't know, tiny little improvement.

[00:23:47] I'm gonna charge you for it or your customer will will hate you. But if you do something major to the business, like, I don't know, everybody's adding AI functionality right now, you're adding AI functionality to your product, challenge your customers for that extra, like segment it out premium price it.

[00:24:03] So that also led to this like, you know what now people call customer success and this whole sort of like internal growth, your customers like we created and our customers were happy to pay us more money because we were this small startup. They relied on us. We were providing more value to 'em and they just wanted us to see us survive because they were banking and building some functionality in their apps that they needed to exist for five or 10 years down the road.

[00:24:30] So it kind of, those, those things all kind of collectively led. And then of course, like, you know, this is the fifth thing, this is definitely later on, you know, this is when you start thinking about, okay, well, so we have this iOS product coming. What, what's next? And you need to have money. You need to have the business model down to be able to invest in the next thing that's gonna grow the business.

[00:24:54] And so I like to tell people, a lot of people don't think, and they don't think about innovation and business model like the last place people, everything's innovation and technology. And if you look at some of the largest businesses in the world, the iPod, what was the big thing with the iPod? 99 cent songs, innovation and the business model.

[00:25:13] I think that's true strategy and. What I've seen, even when I was an attorney, or even now, I've, I've seen a ton of phenomenal products solving really difficult problems that plateaued or didn't get to revenue growth. 'cause they just didn't have the business model. Right. Or they weren't marketing themselves, they weren't telling their story.

[00:25:33] I see those way more than I see shitty products, if that makes any sense.

[00:25:37] Omer: Did you do any outbound, any cold email in the early days to try and acquire customers?

[00:25:42] Jonathan: I would say we did it. We probably did it around 800 to 1 million. We started hey, why don't we try to do this? And we saw, you know, try to think, let's try to do this.

[00:25:53] I think for the SDK business, the the complexity of our cell, I mean, like I tell people all the time, it's kind of like a four-part sell. Like first you gotta convince the person they need to build off A PDF, right? 'cause there's other ways to build. Then you gotta convince some, like, you know, open source out there isn't gonna solve your problem.

[00:26:14] You're gonna run into issues. Well, they're gonna wanna figure that out. Then you're gonna convince them, Hey, there's other, you know, competitors in this market, but we're the best one for your need. And then the fourth one is, oh, hey, by the way, we're not charging small prices. It's a premium priced product.

[00:26:31] That's a really difficult sell to do outbound, especially when you're not, I mean, we're not looking at two year shit. We're trying to survive. We're trying to like look at two year, you know, sales cycles, which oftentimes outbound sales cycles, unless you have a product that you can immediately identify the need and you can come in, sell it quickly.

[00:26:51] It's not a complex thing. There isn't a lot of competition for it. That's where outbound works very well. And it just didn't work for us. It never, it never, we never saw the ROI. For it to be frank.

[00:27:04] Omer: Yeah, I mean, that makes a lot of sense. But I would say equally with content marketing, SEO, you have some challenges there as well.

[00:27:14] I mean, yes, you can, you can reach people who are, you know, talking about the funnel problem aware, they're solution aware, so they're more closer to being convinced to that buying decision. But you also have this problem that if you're publishing content, it may not drive any organic search traffic for six months, 12 months.

[00:27:41] Right. So how, how, how did that work out for you guys?

[00:27:44] Jonathan: I mean, the big thing that I think we, we, it was harder for us and when we released our Android framework a little bit later because we weren't knee deep in the Android market. And then when we released, we released our web framework in 2017, it was like, but what we did on the web framework each one of these times, it's like recreating a company almost. We were first on web assembly pretty early. Web assembly is basically like a, a technology to be able to run backend processes in the browser client side. And a lot of people weren't really sure whether it was actually ready for production when we started using it.

[00:28:18] And we knew early on we kind of made a bet we're gonna be there. Also, we created a, a website called is Web Assembly fast yet. And it was a benchmark where you could literally run your things through web assembly and it show you what it do on different browsers. We got on Hacker News, you know where our, where our audience is.

[00:28:39] We told 'em about this, we promoted it, and then all of a sudden people started going to it. And then lo and behold, one of the major, you know, browsers, I think it might have been Chrome, reached out to us and said, Hey, we want to use your browser Benchmark Chrome. Holy shit. Well, then all of a sudden Safari reached out to us, Hey, we want to bench, we wanna use your browser, benchmark safari off it.

[00:29:00] That alone, like those type of, and the the example I'm trying to give is, if you can think of something that is important to your customer base, where they're at, where are they hanging out, where are they at? I don't like, you know, in today's world, maybe it's Reddit or maybe it's Stack Overflow, maybe it's some forum.

[00:29:20] You gotta find where they're at. Or the, you gotta define who your ICP is. You gotta find out where they're at, become part of that community. You know, that, that's the, the thing that I think is really hard is when you have founders or people that are trying to solve a problem and they're not involved in that community at all, they don't know the community, they're just trying to sell to that community.

[00:29:43] You're gonna, yeah. You're gonna be you know, putting out content and it's not gonna. Not gonna mean anything. So I think the more you know that ICP, the more you understand what day value, the, the day-to-day problem they're going in. This is why so many problems so many businesses that are started on problems that people have, that they solve for themselves work out so well because you are that ICP.

[00:30:04] So the more you know that ICP then find out where they're at, then try to write compelling content. You know, one of the things, it's like, people always have a writer's block and say, I don't know what to write about. I think what people don't realize is, look at the way people consume content online.

[00:30:21] Half of the things they wanna know is, who is Jonathan Ryan? What does Jonathan Ryan do all day? What isn't? And Jonathan Rye's life look like. You know, everybody cares when they're interested in a company or interested in this. They care about what is, what do you, what do you like? Who are you? Like, what's it around it, what are you doing?

[00:30:38] Just write. Just write about your day. And yeah, it's a habit, it's a muscle. And I, you know. Examples I like to give is like you know, Bruce Springsteen, everybody knows Bruce Springsteen is like, you know, artist or whatever. What they don't realize is how much, how many songs he produced. You know, Picasso, I think it was like the, the whole joke of Picasso throwing away the napkin and the lady going, oh, don't throw that away.

[00:31:03] Give it to me. And you said, okay, that's, you know, 20 grand al can enact and be worth return grand. He goes, well, you know, you just did it in, you know, five minutes. He goes, I didn't do that in five minutes. I did it in five, you know, 50 years or whatever. That's the thing. You don't know what's gonna catch.

[00:31:17] So you gotta just kind of do these, do these, do these. Don't, don't make them huge bets. Do as many little small little bets. Many little small, little tests. Brute force the problem, brute hack, you know, brute hack it and you'll start to see stuff that works. But I think the first thing going back to you saying is like, you gotta know your ICP very well.

[00:31:35] Know what they value, know where they're at. Engage 'em. I don't wanna say it's as simple, but it is that simple.

[00:31:42] Omer: So that example you gave about, you know, how, how you spend your day, where were you publishing this? Was you, would you publish it as a blog post? Would you share it on, on Twitter or you tweet about it?

[00:31:52] Like what was the …

[00:31:53] Jonathan: combination of both you know, talk about it on Twitter, were you publish it, you know, one of the first thing I did was Peter was writing a lot on his own personal peter steinberger.com type website. Like everybody does. Most people separate their personal brand from their, you know, their startup brand.

[00:32:10] 'cause they, they wanna write about these things that matter to 'em here and they don't want to dute it over here. And I told him, no, stop it. Like you can be the personal brand. We are the personal brand. Talk about it on PSPDFKit. That's who we are. Maybe isn't about the product we're doing. Maybe everyone doesn't wanna read it, but there will be people that will go, I.

[00:32:29] I don't know, like, cool, he has a really good, you know, office desk and what, what monitors does he like or what tools does he use? And they care about that stuff even though they may not be buying the product that you're doing. But when somebody comes to him and says, Hey, you, I have this document problem, blah, blah, blah, they'll go, Hey man, I know this really cool guy.

[00:32:48] You had a really cool office set up. And by the way, I think he might sell A-P-D-F-S-D-K should just check it out. And that, that is the magic, that's the magic of what you need to get started. That's a little tiny spark you need.

[00:33:02] Omer: So, so in many ways, yeah, you were creating content for your, your target customer, your ICP, but you were also just sharing just life, like what you were up to, what you cared about, what you were interested in with the world and in, in many ways it just, even if they weren't your target customers, I.

[00:33:23] They were people who were able to build some kind of connection with you and remembered you had some PDF thing.

[00:33:33] Jonathan: I mean, the, the thing is, I don't know what, I don't know which article or which tweet or which conversation I had on the coffee break at a conference led to them telling someone else about it.

[00:33:47] So I just do all of them. And it became a habit. And LinkedIn. Now is this, I mean like, come on. Anybody that's on LinkedIn, this is all LinkedIn now, like, and it's very noisy. Twitter's, I mean disastrous now, but like, Twitter wasn't like this before you could find, I mean the reason we were on Twitter is 'cause the Iowa dev community was on Twitter then.

[00:34:07] And so like that was where my, that's where our audience group was. Right. And so yeah, I think that, you know, these people were all throughout the US and Europe and that was our water cooler. So they also wanted to know who you were, you know, at the water cooler.

[00:34:24] Omer: Cool. So let's, we, we, we, we've talked a little bit about growth and, and just generally in, in terms of like getting to that first million and some of the things you were doing around content marketing and SEO and so on.

[00:34:36] Let's talk about a little bit about the product side and in, in those early days, it was great. I mean, you, you were attracting these people. The business is starting to grow fairly quickly, but then you've also got this problem where you're getting all kinds of random requests for things that seem super important, that seem like features that are gonna move the needle with growing revenue even more and faster.

[00:35:05] And you guys were trying to respond to every, every request that was coming in. But as you learn the hard way. It wasn't always the best way to invest your time.

[00:35:14] Jonathan: The treadmill until you get the product market fit, or you can afford to say no to customers. This is one of the probably hardest things because you get into, normally when people get into a business and they do it, they have a vision, they have a, you know, it's a baby, we wanna do this.

[00:35:34] We start getting customers, and the customers start telling you what your baby needs to look like and what clothes you need to dress it in, and you know, it needs this or needs that. And. And they're, they're pushing what they need, right? Or they're pushing the extra thing. And software is, I think all software, you know, the beauty of SaaS is, can I take something that everybody wants their own Ferrari and I can I make it into a sedan for at least most of the people or a van or whatever it, it's and then people ultimately then want you to like, yeah, but I want the van that drives as fast as a Ferrari and, you know, they, they start then trying to push you back into customization.

[00:36:11] And this is a rat race, especially when you need revenue. Because some of those customers I can't say no to, and some of those customers, like, I don't know, they're threatening to churn. If I don't do it, don't go somewhere else. Yet I have, you know, a small engineering group that didn't join just to erratically do the next fire.

[00:36:32] And I mean, really it became siding like. What's the issue of today that the customers gonna scream the loudest that we need to do right now and get it fucking done? And I think it, it takes both guts. It takes that there's nuance that you need to kind of balance the two. You gotta get to a point where you can say, I'm gonna time about two, two weeks where I tell the customer, sorry, it's not gonna happen until later.

[00:36:58] So you can work on the things that you think your vision of the product and where it should go. The other thing is like the tech depth. This does, I mean, if, if you do it long enough, you'll, you'll freeze. Like, you'll literally not, you'll, you'll have something that's so fragile, you'll have to start from scratch again, and then you, it's the death nail to, to a SaaS business.

[00:37:19] 'cause if you start losing customers quickly, they don't come back. Right. You get a reputation of, I use that product, it's so fucking buggy. You know? So like, you gotta keep up quality, right? And so. But it was really hard.

[00:37:32] Omer: You said one thing to me that you said the impact was good short term for the business and bad, long term for the business.

[00:37:42] Can you give maybe an example or two about what you mean by that?

[00:37:46] Jonathan: Let's say a customer comes, they need you to do some customization. It wasn't on your red map but they're willing to pay their, your largest deal today. Cool, we're gonna do it. Let's do it. Let's get it done. Two weeks go at it, you sprint and you do it.

[00:38:02] You get that money feels great, especially in the early days. I mean, one of the pieces of advice I'll tell people in the first million is remember how excited you got when you got what your largest deal was then. Because if you are successful, you miss how excited you got when those deals came in. And so the thing is, you're excited about it at that moment, you know?

[00:38:25] But then you set the expectation with the customer that, you know, if they say jump, you'll say how high? And they don't care how much money you spent. And then when you say, well, but if you want me to jump that high again, I need you to pay me more money. And they're gonna, but I paid you so much money.

[00:38:41] No, no, jump again, jump again. And then you have the next deal that now is two times that largest deal and they're saying, Hey, jump, I got this thing I need you to do, but you're still jumping for the, the one that was half the size of it, and you'll know how to juggle the two. So what's really hard is that's a tough conversation that should happen at the beginning, should happen midway through.

[00:39:04] Like anything. Sometimes setting expectations early is better than having to come back and set expectations later. The other thing is, a lot of times the way when you're a small, you know, you're small, you're, you're going out, you're thinking, man, it's so important to me. It must be so important to the customer.

[00:39:21] Have to do it. Well, maybe you don't have to do it. Maybe they don't need it. Maybe you just ask them like, when, when would you need this done? Why actually, can you get this done in a year? Oh, shit, I thought you wanted it in two weeks. Yeah. Cool. Well, let, let's put that on the roadmap. But if you never ask that question, you're sprinting to do it in two weeks.

[00:39:37] And then when you do it, they go, wow, you did that so fast. Let's see what else we can throw at you. And it's like, again, short term revenue gain, short term excitement. 'cause you close the deal. Long term you're losing control of, of that roadmap. You're losing control of product and you're setting yourself up for bad, bad, like, you know, could really piss off that customer.

[00:40:01] If you've set an example so far and now all of a sudden it's different. And then that large deal, churn. Churn because they view you as a consulting company, not as a SaaS business. That, that, that's the, especially with large, large customers and early days, you get a big customer coming. Sometimes it's worse.

[00:40:20] Then if they didn't come.

[00:40:22] Omer: Yeah. So I, I think that's, that's, that's great advice I think for many founders who are in that situation. In an ideal world, if you had product market fit and you, you were getting tr you know, great traction, you could say no to a bunch of things that just feel off strategy in those early days.

[00:40:36] It's really hard. And the, the key from what I heard from you was being able to set expectations with customers. So you're not always seen as, you know, the, the, the guys will jump whenever they, they, they command it. And in order to get there, you need to get better at asking questions and not making assumptions.

[00:40:59] And what, what you said about, you know, when they need it is one example of that. Others, I think could be what exactly is it that you think this is gonna solve and is there a different way that we could help you solve that now without going off and building a new feature?

[00:41:15] Jonathan: Yeah, exactly. And part of that, one of the reasons.

[00:41:19] I do think this idea of you need to have a relationship with your customers early on. This is a hard thing with product-led growth strategies, they're great, but then immediately you need to start talking to those people. 'cause otherwise they start talking at you through support and you don't have a relationship with them to have sort of a partnership discussion where they understand you're trying to build a product in the direct chain and you understand why they value your product and what they're using it for.

[00:41:47] That's super important.

[00:41:49] Omer: So, so the first million eight months, what was the next big milestone for you and how long did it take to get there?

[00:41:57] Jonathan: Yeah, 5 million probably was a big milestone. It probably took us three to four years. I'm trying to think. It would've been 2015 we got to a million and it would've probably been entering 2018, so maybe three to four years that it took us to get to five.

[00:42:15] And then, you know, from 2018 to 21 to get from five to 12. And yeah, it you know, a couple things changed. We, we tried a lot of new products. We, we started, if you, if you knew the graveyard, I mean, we're not Google, but it's almost as bad, or we didn't know what, what are we, we built a framework. Are we a frameworks company?

[00:42:40] Are we a PDF company? Are we just, let's build a product and if we can put it out there and people give us money for it, we'll be any one of these things and have a bunch of little small businesses. We didn't really have a strategy or a coherent strategy. There.

[00:42:54] Omer: So what kind, what kind of products were you building alongside what you already had?

[00:42:57] Jonathan: We had a, a, a perfect example. One of the first products we released was called Watchtower. It never a control tower, sorry. And it was literally a licensing tool because we built our own internal licensing tool to license our products. And so it kind of became like a lightweight CRM. We had a customer database in there.

[00:43:17] We invoiced our customers through it. We gave out licenses and we tracked those licenses in it. So we said, well, other, other companies that are building products need something like this, so let's put it out there. We put out a website. We had an ability for somebody to kind of like, you know, call us if they need it, and crickets.

[00:43:35] And it was like, okay. Yeah. And then the worst thing is you get one person that's interested and it's like, oh God, am I only gonna sell this to one person? We tried, I. We tried a end user product that we call dock flow or dock flow, that it was kind of this idea. We had a customer in Europe that they were doing, you know, they were sending these people out to factories to do maintenance of these robotic doors.

[00:44:00] And we thought, okay, this is kind of like people in the field and then you have a central base. So we created an app, we'll give the central base a viewpoint of everything, get all their documents in order, and create a client site app for a mobile device for the person in the field. And the, we worked with the customer, they loved it.

[00:44:18] We had two or three other people who got interested in different places, started to work on it, and then it was like, but we didn't have a self-service model for them to set up. So we had no, like, it literally was us starting a whole nother business while we were focusing on the, the thing that was actually making us money.

[00:44:34] Omer: So why we, why did you guys. Do that. Why you, you've got one business which group fairly quickly to the, to the first seven figures, and then it seems like you've got focus, clarity where you need to take this, and then suddenly you've got all of these other products, you know, this little cottage industry that you're building with these different things going on.

[00:44:58] And often when I see that with founders in the early stages, the question for me always is like, do you not believe that this first product can, can be something bigger? And are you trying to, you know, hedge your bets and, and, and try to do a bunch of different things? Like how did you guys end up in that situation?

[00:45:20] Jonathan: You know, and this goes back to the difference between a mom and pop viewpoint of a business versus like a, a growing like, you know, investor led company. I think a mom and pop like, I don't know, you've been to a nice restaurant. Maybe they have two restaurants and you're sitting there going, God, you guys should be all over America.

[00:45:39] This is phenomenal. And they're going like, you know, these two restaurants to get 'em up and running. They create a good lifestyle for us. We get, you know, we get to go do this, we get some money and why don't we try to not get over our skis? Right. So we kind of had that view. Like, and the other thing was like, if you think about it, if you go from like 2013 to, you know, essentially 2018, that's five years.

[00:46:02] And it's like, you know, you get like, well, let's try something else. Let's do something again. Let's, and the thing we did, I think we weren't sure of the size of the tam at the moment, you know what people don't remember is digital transformation. It's been a thing that's been going on forever. It just like is the thing that was always on everybody's five-year roadmap.

[00:46:24] It was just always on the five-year roadmap. It wasn't until Covid that it was like, oh shit, that we needed to have that yesterday. And so it was kind of steady growth, but not rocketship growth. And so here we are arrogant founders. We, we grew business. Let's go for something that grows even faster. And you know, as Rocketship growth, and it was, yeah, it was distracting, but it was fun.

[00:46:49] Like we got excited by it. It was shots in the arms of motivation. It was cool to see the products we put out. We learned we learned from it for sure. But we were also still growing the other business kind of sustainably as well. But like, I think one of the big things people don't realize, what's the difference between a mom and pop business and an investor led business is like an investor led business.

[00:47:12] You're not taking capital out of the company at the end of the year. Now they're always focused. If anything, you're building cash in the, the company or you're looking, how can we spend that money? You know, the classic VC question is, if I give you $10 million or $1 million, how can you 10 x your business?

[00:47:32] I mean, that, that's a really big question for people that are just bootstrapped a company. Whereas when you bootstrap a business and you're getting your, seeing your income go up, man, you wanna see that income go up and you're getting comfortable. Your lifestyle is growing a little bit, and so you're more conservative with that investment.

[00:47:50] And so I think that was one of the reasons we did it. Some of it also was, I mean I can tell you in 2015 I wanted to go to the web, but my, you know, web assembly wasn't around. My technical founders were kind of like, yeah, this, we're not gonna, that, that's gonna, we're, that's gonna take us five years and we need this many people to do it.

[00:48:10] And so we just never considered it. It wasn't until later that they, I just said, cool, can you just spend a month and research this and see what's possible? And all of a sudden, lo and behold, Hey, I think we can, we found a breakthrough. 'cause we have phenomenal engineers that figured it out. So some of that was just tiny.

[00:48:26] Omer: So the, you, you bootstrapped through to 12 million in ar. Once you got the focus back and continued growing this business and then you raised the, the private equity money at that time, your two co-founders decided that, you know, they were gonna cash out. And so you are the one guy left now and it's not a bootstrap business anymore.

[00:49:01] It's become that investor driven business. And you don't have your co-founders, how, how did life change for you?

[00:49:08] Jonathan: You know, one thing I'll say, and this is not me, like insight Partners outta New York City as my investor. I was lucky that I literally talked to just about every VCP, like in the similar sizes they are.

[00:49:26] And I got to choose who I ultimately went with. And they're a phenomenal investor. They're, they're very founder friendly, they're very growth oriented, even with, you know, even in today's market and what's happened in Tech and SaaS. But it was a big change. Some of it was, I mean, like, you have to think, for the majority of my time at this company, I viewed it as not my company, it was, it's our company.

[00:49:53] I use that word. It's me and my three business partners. I still call 'em my business partners even though they're not. And that changed. So now it's like, oh man, this is Jonathan's company. Well that's different. I had it was a really big education in that first year. You gotta be able to, you know, a good I would say investor led leader of a company, whether they're the founder or the CEO, you gotta talk two different languages 'cause you're the operator.

[00:50:19] You know what needs to get done to, to actually execute the plan. And investors are not operators or investors. They're looking at numbers, metrics and they expect you to tell them what the number and metrics would be and then go, go figure out how to do it. And it's easy, I think, in their operator's seat to go, oh, there's Dan Investors.

[00:50:41] They don't know shit about running a business. And I, I know people that do that and you'll quickly find out you'll be out of a job. 'cause they'll find somebody there. It understands both. And so you kind of get, you kind of get both, like they have pattern recognition. I mean, they have 700 companies in their portfolio, so they're seeing a wide, larger range.

[00:51:02] They have operating leaders in groups. The other thing was, I had a boss like that. That's weird. You know, one of the things people love about becoming a, a bootstrap founder is I don't have a boss, right? I'm my own boss. And now I had a board. And then really what I found out with is, yeah, I have a boss, but they're looking to me still to tell them what to do.

[00:51:23] They're backing me. So it's not really a similar like, Hey, what do you think I should do? Type relationship? It's a, I think we should do this. What do you all think? And then they look at you and they're like, all right, well, we're okay with you doing that. We're gonna look and wanting to make sure you achieve X, Y, and Z.

[00:51:41] And so it creates, I think, a really healthy bit of accountability. Because it removes this, like it removes this, I'm gonna go do this other product that's not in focus with what I'm doing. No, no. Focus on Dan Core business is making money. And I think sometimes founders become bad business people because either they think they're invincible and everything they can do, they can be do successfully or they get distracted or they don't like the word accountability or ownership.

[00:52:12] They kind of like, well, whether I have a good year or bad year, I own this thing and I'm cool and I'm there. And that's just not the real world when it comes to, you know, what an investor is, investors trying, they're giving you money to grow it, to return money to their shareholders or their LPs. But it was different.

[00:52:29] It was absolutely different. I had a little bit of anxiety around it to be frank. And it was good change for me. It wasn't bad change. Yeah, it was, the other thing was like, we grew so fast, we went from 50 people in 20, 21 to a hundred people basically by midway through 2022, or sorry, mid, sorry, beginning of 20, 23.

[00:52:51] So over a year we doubled in size of people. And the thing I loved about the smaller business was like, man, like I'm not the CEO, I'm Jonathan. I'm just, I'm sitting here right next to you hacking away, trying to get this thing done. We're, we're a family. We're trying to, we're trying to survive. We're in it together.

[00:53:09] And then when you scale, it kind of becomes like, I mean, I'm running a business. These are my employees. And not even so much that I view 'em that way, but when I walk in a room, it's so shit. Everybody gets quiet. The big boss just walked in and yet I don't feel like the big boss and I don't want to be the big boss.

[00:53:25] So yeah, there's definitely things that change.

[00:53:28] Omer: Yeah, I mean it's a fascinating journey and, and kind of going back to the. You know, jumping off the cliff and joining this little startup, doing 20 KMRR to, you know, where it is today. It's, it's amazing. I'd love to keep the conversation going, but we should wrap up and get onto the lightning round.

[00:53:48] So I've got seven quick fire questions for you. You ready? Yes, go ahead. What's one of the best pieces of business advice you've received?

[00:53:56] Jonathan: The best way to answer this is to say you know the bad one I have is make your customer, if a customer value something, they'll tell you by paying you for it.

[00:54:05] So make, make people pay you for things they value.

[00:54:09] Omer: I love that. What book would you recommend to our audience and

[00:54:12] Jonathan: why?

[00:54:13] I mean, I have three. I'm a huge reader. So I could probably give you a list where we're blue in the face. I really like the “Hard things about hard things”. It's been Horowitz from Ress and Dress in Horowitz.

[00:54:24] I think it just really solved some of the like people issues as you scale up some of the really hard things that you don't anticipate when you're first starting out. I also read this book Scaling Up, how a few companies make it and Why the rest don't. It's a good collection of a lot of books that I think are good.

[00:54:41] When you start thinking about what are core values, why do I need to do this? What's we had, things like this. I think Zero to one is a classic. It's really fascinating book. It also hits at really what it's like to really live that journey in some of those lessons that everyone goes through.

[00:54:56] So, sorry, classic books, but,

[00:54:58] Omer: What's one attribute or characteristic in your mind of a successful founder?

[00:55:01] Jonathan: I go with this, like the original quote I told you with Steve Jobs, but you, you gotta believe you're gonna be successful. And what I mean by that is like, 'cause if you don't think you're gonna be successful, you're not gonna be willing to do what you need to do.

[00:55:13] In the moments where you're not sure whether you're gonna be successful, that will ultimately make you successful. So if you don't have self-belief, you might as well stop. 'cause you're not, you're not gonna make it. You're not gonna have the energy, you're not gonna get through the lows. So to me it's like really core that you gotta have self-belief.

[00:55:29] You gotta, you gotta something in you, you just gotta believe I'm just gonna make this work. So that, that to me, what they're call it grit and I'm sure there's a million ways they call it, but that's a belief would be the way how to put it.

[00:55:40] Omer: What's your favorite personal productivity tool or habit?

[00:55:43] Jonathan: Yeah.

[00:55:43] You know, I'm ADD-ADHD diagnosed ADHD. So when I was, when I was trying to do focus work, it, it hurts me. But when I'm trying to do context switching in a lot of different jobs, it's actually kind of a so I'm not one of these people that I have this system. But one of the things I've really done since law school is like, when you're enthusiastic and you're motivated and you're in the slow and you're having a really good time working on something, do whatever you can to, to stay, make stretch that time.

[00:56:13] Don't get up. And then the other one, and probably the key one that I think a lot of people don't think is like, people have bad days. If you have a day and you're not, you're not productive, get the hell up. Go do something else. Go walk, go do something you enjoy. I don't know, read a book, watch a television show.

[00:56:29] The last thing you need to do is sit at the the damn computer and try to bang something out while you hate it and you're not doing good work because by you getting up and going to do something else, she'll find you break it up and you might then return to it, be motivated and get in the flow state. So I really focus on those energy levels and I don't try to make it fit into like a perfect circle, if that makes any sense.

[00:56:50] Omer: Yeah. Yeah. I, I think I'm you, I'm, I'm like you. I, I haven't been diagnosed, but I'm pretty sure I have ADHD and struggle a lot with, with focus. And I think the, one of the things that I've learned is that when you're having those tough moments. The harder you try, the worse it gets, right? And to be able to walk away and just do something else, and so you can reenergize yourself, you're gonna come back and you might even have the solution to whatever it was you were struggling with.

[00:57:18] So that's, I think that's great. What's new or crazy business idea you'd love to pursue if you had the time?

[00:57:24] Jonathan: I joke there's a really bad joke I have with my family. The, there's a thing called a grill mirror. And I always thought like if I you know, if you want the perfect grill marks on the bottom side of your, you know, steak or burger, you can imagine this little dentist thing that goes in and it shows that, okay, they're even, so then I flip it and even, and I say that's my million dollar idea.

[00:57:44] Mothers will buy 'em for their son-in-laws with their favorite sports team on 'em or whatever. Oh, that's a jokey one. Obviously I have three children, young children really care about climate change. It's kind of the one of the good side effects of our businesses. We really do, we plant trees for, you know, we planted 10 trees per customer last year.

[00:58:04] I've always thought of like a mint.com for climate change. The idea that if you could then build this tracking system, and I know there's things that tribe, but like the thing that mint.com does is or did was it listed everything and then you could apply the score and then you could show like, Hey, I, this is my personal impact on climate change.

[00:58:23] And then if you got the government involved, which I think they will get involved, at some point you can get like, Hey, propose to the government get tax subsidies for people that do this. If you have a good climate record, you get a tap. So if you have a bad climate record, you gotta pay more extra money or something like this.

[00:58:37] I don't know, crazy idea. I don't know if it ever commercially would work. Other than that, like I love I love stock trading and Forex trading. So your part of me thought about just starting hedge fund, to be frank.

[00:58:51] Omer: What's an interesting little fun fact about you that most people don't know?

[00:58:53] Jonathan: I guess you, you pulled up the one that I would kind of say like, I was in a, you know, I was an attorney and most people don't think of you know, a startup founder, let alone a business as an attorney.

[00:59:04] Omer: And finally, what's one of your most important passions outside of your work?

[00:59:07] Jonathan: Yeah, lemme, so I've talked about, I have a wife and, you know, three young children. My daughter's, you know, attorney 10. My son's seven, my youngest is almost four. So obviously dad time takes up a lot of stuff when I'm not here.

[00:59:20] I love soccer. I play soccer. I watch EPL. I'm a huge Arsenal fan, so go gunners. And then I like golf. I mean, I know these things sound typical, but golf is a perfect sport that is so frustrating to play and you're competing against yourselves, but it's a mental grind. And I think one of the people, like personalities like us that get into entrepreneurship, we like, we like challenges.

[00:59:43] We want to continue to push ourselves, continue to improve, so golf, to be scratches that itch and a non. A work related setting. But yeah, I would also tell you just last thing with this I'm not a big believer maybe in this whole like work life balance type thing. And part of the reason I say that is I like to tell people you know, I went to law school 'cause I wanted to be a good father.

[01:00:06] I picked myself up away from the computer because I wanna be a good father and I wanna have my kids, I go play soccer and do golf 'cause I have to manage my anxiety levels or I want to be healthy. Or otherwise I would sit at the computer all day long and it wouldn't be forced. You know, I, I love my job.

[01:00:24] I have literally, I'm living the dream. It's one of the, the best job I've ever had. I've had a lot of jobs, so.

[01:00:30] Omer: That's a long way away from the days when you were working in Sears.

[01:00:34] Jonathan: Folk cars. I've worked in politics, I've done all the jobs everyone hates

[01:00:39] Omer: Also j Jonathan, thank you so much for joining me and sharing your journey of building this business.

[01:00:44] If people want to check out the pro, the, the, the, the SDK, they can go to PSPDFKit.com and if folks wanna get in touch with you, what's the best way for them to do that?

[01:00:55] Jonathan: Yeah, hit me up on Twitter. It's jdrhyne is the handle. That's probably the easiest way or, you know, message me on LinkedIn.

[01:01:04] But you know, I still check Twitter. I'm on threads as well. Same, same handle on threads. So yeah. And Omer, thank you so much for the opportunity. It was an honor to speak with you.

[01:01:13] Omer: It was my pleasure. Thank you so much. And I wish you and the team the best of success.

[01:01:17] Jonathan: Awesome. Thank you.

[01:01:18] Omer: Cheers.

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