Jon Mest: How AI Is Changing Growth, Teams, and Startup Strategy | SaaS District #234

Hello, hello everyone. This is your host, Akhil Jabbar, and welcome back to another episode of SaaS District. In today's episode, we'll be talking about how AI is changing growth teams and startup strategy, and especially in the search world. Today we have our guest, John Mest, joining us. John is the CEO of ChatRank and just ReachOut, where he operates at the intersection of data growth and marketing. John also holds a background in applied mathematics from Johns Hopkins University and an MBA from Wharton School. So very impressive background. Currently at ChatRank, John is focused on helping businesses win in the era of AI-driven search, which is super interesting and exciting these days, where relevance, quality matter more, a lot more than ad spend. He also leads a company called JustReachOut, which is a PR platform that enables companies to secure media coverage through targeted outreach, analytics, and proven frameworks. So welcome, John. Super excited to have you on the show today.

Thanks so much for having me. Excited to be here.

So, John, I guess you've built many companies, successful entrepreneur across different industries, right? But specifically focused on data growth and marketing. Can you share just a little bit how did that journey— share a little bit about your journey and how did that shape how you think about building startups today, especially now in 2026 with the AI era?

Yeah, my journey is interesting and fun and exciting, and there's no direct path to entrepreneurship or starting a company. I'd say everybody has their own journey. Mine was, I really liked solving problems. That's why I studied applied mathematics, a lot of computer science work. I kind of came out as a developer and a more technical person, and I joined a startup early in my career that I was there for about 3 months building this product or helping them build this product. And they were like, You seem to be able to talk to people. Do you want to go out and sell this to like the two? I was like, wait, what? Like, I was 23 years old. I didn't know anything about sales. They're like, oh yeah, P&G like needs like this project. You want to just fly to Cincinnati and go like sit with them and just do it? I was like, okay. So like, that was my sales start was just like being like a kid and not really knowing what I was doing, but just building good products and building smart things and just, I don't know, being able to explain them to people. And I realized pretty quickly that it's not sales and running a business unit or kind of running these things is not necessarily just about Like, how smart can you be? It's really about like just listening to the customer, solving their problems, understanding what they really need, and finding a way to solve it in a way that like they want to pay for. And that's the end of the day is what we look to do. And while I'm sure we'll get much more into this and how that— what that means for today in 2026 and building products and companies and everything else. But for me, like my journey really started as just how could I be a really good technical salesperson? That's where I started. I got my chops as a sales engineer for many years, just working with really accomplished, great salespeople that taught me kind of the ropes there. But then really like actually being the boots on the ground, literally spent my entire 20s traveling on an airplane to different companies, but like working on that skill set. And then that really led me to, you know, figuring out what works, what doesn't, how to build and grow a business.

Love it. And now you've run, you know, running 2 successful companies, one being ChatRank and also JustReachOut. How would you say, you know, your approach has maybe changed over time in building these products? And how are you thinking about now differently than maybe when you first started?

When we first started, the company was newish, but we had customers. We had a good amount of revenue. We had the ability to kind of go into there with an idea or like, here's what has worked. Here's what's worked for the last few years. We have a good sense of what this means. When you're starting from scratch, building 0 to 1 is challenging. It is tough. We've done it now a few times, and I got to say, there are ups and there are downs. There are good days and there are bad days. But I think the most important thing to realize that I've learned over this time is you can't just build what you want to build. You have to build what you want to build with reference to the customer, what the customer needs. And if you just build what you want, unfortunately, it might not always work out because then you'll go to sell and they'll be like, I don't pay for this. This is not what I want. And so I've had the privilege of working with some amazing engineers as well on our team, especially Joe, my co-founder, who just really is like the engineer that wants to hear from the customer what they need and loves like building like for successful businesses like that. And so anyway, we've always kind of taken that approach of build what the customer needs, have them pay for it, and then obviously use that to then fund the next project, the next project. And so I'm sure we'll talk about bootstrapping and what that means and how you actually can do that when you're building zero to one. But it kind of forces a discipline in us that we really love, which is that, I mean, you only exist tomorrow if you sell a customer today. So if you build something they don't want, you're not going to exist tomorrow. So you have to build what they need. And if you can get them to pay for it, that really implies and kind of tells you all the signal you need to know that they're interested and they really want to kind of continue doing this.

Absolutely. I mean, it's just the constraint that's kind of put onto you. I mean, as you're, you know, as our visionaries and entrepreneurs, we just want to build. We have these ideas, we have these things that we want to build. Like, this is what we want, this is what you need. But it's like, no, you have to actually just listen. And that's where people will start paying you for it and you actually succeed when you can start to listen to them. Yeah, I love it. So obviously, you know, building in 2026 has changed a lot, right? Like the last few years, totally different. Today with AI, it just becomes so much more efficient, a lot quicker. All these tools that essentially build super quickly for you. How are you looking at how is AI changing what a startup team should look like for you guys and how you guys are looking at building?

I mean, first of all, I'd say for better or for worse, we don't have as many engineers as we probably would have otherwise if this was not, you know, 2026 with like the agentic coding systems that are available now. That is also to say that we feel very strongly that because both my co-founder and I have a strong technical background and know how this stuff works, we are much more efficient, much more able to utilize these agentic systems to code and to build things that are much more effective and efficient than, say, if we just had vibe coded the whole thing and not really known what was in it and how it was working. And so we always caution, and we actually have gotten pretty good at noticing when products You sniff around, you're like, hey, I don't even know if this person even knows how this thing works kind of idea. And so for us, we feel really strongly that if you're going to build a premium product and you're going to market it as a premium product and sell it at a high price point, which is what we do. I mean, frankly, ChatRank is a premium product in the self-serve market for where we are. We're not the most expensive product. Those things are enterprise tools that cost hundreds of thousands of dollars, but we're not $39 a month either. We are just clearly a premium product. You have to be able to explain why and do that. And so for us, it is the idea that we know and understand what we've built. We have good foundational frameworks for it. We know our data layer is better. We know our agentic recommendations engine is better. These things are just things that we can feel really confident about. And so we believe that truly. And for us, leaning into that has been really important to kind of make sure that we know that we have a premium product and here's why. Not to say that there isn't a world for a less sophisticated version of what we're doing or what any SaaS person could do. But I just think for us in general, we've always kind of taken the approach of if the moat or the barrier to entry is smaller or less or nonexistent even, like, how do you stand out? What's— it's building a premium product that works and you listen to the customer, make sure it does exactly what they need. And so we've seen some of our competitors kind of fall off a little bit when they are clearly building what they think they need to build or what they might have heard once. But it's so evident that they haven't really talked to enough customers to realize that this is not the right thing to build. And so we've seen some of our kind of even like very well-funded competitors start to struggle in some of these areas too.

Yeah. So it's interesting, right? You see, you know, people, competitors are well-funded, they raise capital, but sometimes that doesn't mean they're able to build a premium quality product as seamless as you guys have done. And you guys, like you said, have mentioned you've chosen to stay bootstrapped rather than raise any venture capital, built a great product. And, you know, it seems like you guys are growing well. What drove that decision? And why don't you take on capital to accelerate or fuel growth? And maybe how does that influence the way you build and grow today?

Yeah, I'd say that, first of all, we would be very open to growth capital at some point if that made sense for us. Right now it doesn't. So we're not looking for it. But I'm not against the idea of raising money. So if you see like, hey, you have an opportunity and you just need more cash capital to go make it happen, by all means. If you feel like every dollar in can make you $5 more, go do it. That is an obvious thing. But frankly, you should be in a position of power to go to people and say, I don't need your money. I'd like it to be able to do this thing. You get much better terms and you can have a much better success rate with that. So that's like the first thing. So I'm not anti-capital, but I'd say for us, bootstrapping has really been because we don't— first of all, when we started building ChatRank, the market was early. We were very, very early. We were one of the first people building in this space for AI search. And so if we had raised a bunch of money at the beginning and built these things, there wouldn't have been enough customers to talk to to figure out what we actually needed to build. We would have probably built the wrong thing, and the market just wasn't ready for the explosive growth that a VC would have expected us to have in those moments. And so we're actually seeing some of our competitors that did raise a bunch of money at that time, their products are not where they probably should be. And it's actually quite interesting because they do have, frankly, more engineers than us and more firepower to build, but they might have just built too early and they built the wrong thing because it was too early. So we've had almost the advantage of being able to listen more and more. And when you do bootstrap, like I said, we have a discipline of we have a roadmap, we find an interesting customer, and they say, I love this feature. We'll look at our roadmap, be like, okay, well, we're thinking about that in maybe a couple of months, but if you want that now, pay for it. If you're willing to pay for that feature to be added sooner, because it really means that it'll put you over the edge and want you to come bring it on, like, we'll do it. And so that discipline to kind of frankly turn deals away, but also take on newer opportunities because they're willing to kind of pay for that investment or pay for that development, that has allowed us to be really smart about what we're building. So we're not just going to build whatever somebody tells us, but at the same time, if it aligns to what we believe to be true about the future of this space, and we feel like bringing that forward in our roadmap makes sense, we'll do it. So for us, just thinking about these different things, the bootstrapping has given us the ability to do that because we don't have board members and investors breathing down our necks about where's the next big deal. We've been able to grow in a smarter way. Now, I don't know whether that's right or wrong. I don't really know. But it's somehow we've chosen to build in this space, especially given that we don't need a 35-person engineering team to do this. I mean, it's really— it's Joe, it's our Claude agents, it's a few junior people, and that's kind of how we do it.

Love it. Yeah. I mean, for people who are maybe listening today and they're thinking to follow your footsteps, they want to bootstrap a product that Now with AI, they may be limited in budget and they want to get those few customers. We talk about how challenging 0 to 1 really is. And if you don't have those first customer base, but you want to go out and solve a problem that's meaningful, how would you suggest to them to maybe implement that in practice? And how can they replicate that process and find more success?

What I'm about to say is going to be very frustrating to a lot of founders, especially those that are more on the technical side, because they're going to hate what I say. But I promise you, It will help. I always say talk to 3 to 5 customers or potential customers every day. Like every single day as you're getting started, talk to like 5 people that might potentially be interested. It could be your cousin, it could be a friend of a friend, it could be like somebody you've met on the street, it could be like somebody you reached out to on LinkedIn, whatever it is, just talk to 5 potential customers you think might be interested in what you're building every single day. And you'd be surprised how often you'll like, what kind of signal you'll get from that. So, I mean, record the calls if you can on one of these note takers, do whatever you need to do to kind of figure that out. But you'll realize pretty quickly as you talk to so many people that might be interested in this, what they want. And they'll say, oh, I need this. And then you basically say, would you pay for that? Oh, no, no, I just think it'd be interesting. Okay, that's signal. Or like, I need this. Or if you had this, I'd pay you $1,000 a month tomorrow. Really? Yeah, 100%. I'd do that. Okay, there's your first customer. You have these conversations, you realize it. there's such a pain and a need. You might not realize what that is, and you might think you know, but by talking to the customers, you can either validate your opinions, or maybe it doesn't validate it, but it says something else, or you learn something else, or think you might be interested in, like, they could potentially build, like, tangentially. And so for us, early days, it was talking to as many potential people as possible. And I've found— I've seen so many successful, like, founders where they just took this advice and kind of did lean into this idea. And frankly, a lot of them have pivoted their businesses almost 180 from where they were before, but they realize it's because like, hey, like I wasn't interested in, they weren't interested in this. It was really like this. And well, you know what, there's a market there. Let me go grab it. And so that is what I always recommend at the beginning is like, go do some sales, go out there and start talking to people. And I promise you, even if you're a technical person that hates doing sales, sorry, sorry, that's the reality here. That's how you get the signal you need to build the right product.

And in your case, I imagine, you know, just as an example, you would be reaching out to other marketers, you know, via LinkedIn versus calling them or going to visit them? How are you meeting these people, going to events and trying to get these conversations?

Every different way. Like, we joke that we have like, I mean, one of our most popular channels in our Slack is our growth hack channel. So it's just like, what did you do today that did it? One of our people this morning went to a pizza buffet, like networking meetup, and it was like, who goes to a pizza buffet at 8 AM? But like, he did. He went there this morning. He's like, he sent a picture of the parking lot. He goes, there are cars here. I can't believe it. But he went to this in-person event. And just like found local businesses because actually we do work quite well with like plumbers, HVAC, pizzerias. Like actually you don't need to be a massive SaaS business to use our tool. Like actually it's really helpful for anybody looking to acquire customers or revenue. And so for us, we like, we're always trying to find unique ways to do this. So of course, traditional channels like outreach, LinkedIn, social selling, all that kind of stuff. We're doing a little bit of everything. We do ads, we do, I mean, just about everything we do a little bit of. We love channel partners. Anybody that already has existing customers are great. It's a, it's a channel that's challenging and needs nurturing and requires, you know, some time to get right. Um, you waste a lot of time with bad partners. You have incredible benefits from good partners, but we kind of try every different like thing. And so for us, as we've been bootstrapping, I'd say that channel partners are our best effort because they already have the sales teams, they have existing customers. And if they trust you and think you have a good product and they're willing to sell it for you and let them make their markup and let them sell it for you, that's a great way for us to grow as well.

Absolutely. Yeah, good in-market. So I want to talk a little bit more about ChatRank, the product you're building now. We're talking to the future, going to AI, where AI search is really reshaping discovery, right? Google Search, I imagine a lot of websites now are losing a lot of their search traffic because it's shifted to a lot of the AI discovery. How does that— maybe can you debunk any of some of the myths that are going around? And how does that change what it means for a brand to get found today for better visibility that people may be not aware of?

Yeah. So for those that might have heard, you know, about or knew about traditional SEO, so search engine optimization, the big thing now everybody's saying is, oh, SEO is dead. Like, SEO is so over. That's just not true. It's just changed and evolved. And here's what I mean by that. So in order to win in AI search, this is just in general, not just ChatRank specific, but in general, if you want to win in AI search, whether you're a B2B SaaS company, a medical practice, or a pizzeria, you need to stand out as Being differentiated and the best at what you do in order for them to recommend you. Now, that requires authority and signaling to the AI that you are the best at this. How do you do that? Well, I mean, there's lots of different ways. You can say you're the best at it via your website and your blog, whatever that might be. You need to be able to get the AI to retrieve that information. So you need a good, clean website with good hygiene and good technical SEO to make sure that the AI can— their crawlers can actually retrieve it. You need real humans talking about you. So socials, YouTube, Reddit, like LinkedIn, or it could be Instagram or TikTok for some of our e-commerce customers, whatever that might be. Those channels are great reviews. Like G2 and Trustpilot are super important for software. Yelp is a great channel, or like Healthgrades for medical. These are all things you should be thinking about looking at because AI is looking for signal from all over the place. And so if you're the best, I don't know, software company in the world, but you have no reviews saying you are, It's really hard for the AI to just believe you fully that you just are the best. Now, good user testimonials are amazing. Customer case studies are great. But again, sometimes those are you saying it. Having those third-party validations are always really helpful as well. And so in general, like whatever you can do to signal to the AI that you are the most trustworthy thing in this area is the most important thing you can do. And that is kind of core to traditional SEO as well, just how to do that and the strategies for making that happen and how to actually get that information out there. That might have changed a little bit, and that's what ChatRank helps our customers do as well.

Interesting. So I guess, you know, from when we're thinking about, you know, traditional search, when you're trying to rank on Google, you know, it's a lot of very similar— you're trying to show authority in the space. You're also creating content a lot on your website, your blog, and creating content that, you know, you can rank for on Google. So for founders maybe looking to get started today, it doesn't matter if you're a B2B SaaS founder or HVAC owner, they're trying to navigate this landscape. They're starting to get into SEO and start ranking, getting more visibility. What's some of the biggest shifts that they need to maybe think or need to make in order to compete and grow effectively and actually get some traffic and sales?

Yeah, I think fundamentally the reason that what I'll explain in a second is what a search engine is versus like an answer engine. So what Google traditional search is versus, you know, what Google Gemini or AI overviews are, even just like the new world. So the search engine is truly trying to figure out how do I feed these 10 blue links on the page 1 of Google, say, or like page 1 of search, that is going to be the most relevant to whatever keyword you type in there. So how do they determine relevance? It's this authority score they give it, um, which basically says, do other like authoritative sources say that you're good at this? So if the Wall Street Journal links to your, your software company, then yeah, that, that is the, the, uh, the Google trusts the Wall Street Journal to be an authoritative source. If they say you're good, then you're good. That's the backlink profile you can build. And you can produce content as well that signals to the, to Google and their crawlers that, hey, you know what you're talking about as well. This is kind of this, this mesh network of, you know, links and like being able to prove that you are really good at this, that Google really highly recommends and then gives you those as, as a kind of like, how do you rank in Google? Answer engines. Imagine if you have these Google searches, but then there's an AI bot that goes around and reads all those pages and figures out from those pages where is the answer. So it kind of does your work as the human. So when AI does that, it does your work for you and then comes back to you and says, okay, well, here's actually the answer to that question. So instead of searching CRM for real estate agent, that might be the thing you type in Google, and it might give you a bunch of paid links and things like that, or like people had to kind of figure out what that might look like. A, the AI's going to go, you're not going to say CRM for a real estate agent. You're going to say, I need a CRM that costs less than $50 a month and is really easy to use because I'm not very technical and I need it to like be like integrated with these tools and do this, this, and this. You're telling the AI all these things you like that are very specific to what you need. So the AI is going to take that information, crawl all the results for you and say, actually, I read all your results. Like the most important, the best one for you is actually on page 7 of Google. It's this one. And here it is. It's just going to recommend you that brand. So knowing that as a, as a business, especially for like, you know, B2B SaaS, um, or any SaaS business really, like you need to know who your customer is and what they're searching, what they care about, and then make sure that your content, your website, your reviews, your third-party mentions, your socials, all that stuff reinforces those things. So if you are really good at being the affordable option that integrates with this tool, have a giant freaking landing page that says like, you are the affordable option that integrates with this tool and you'll capture every one of those customers because AI will just recommend you for that because you're the only one that's saying that. And so for us, when we're working with our customers, a lot of times it's like, how do you be as specific as possible? How do you make sure that you can explain exactly what you are and who you are to your core ICP and make sure that like that person that really wants to be, you know, is your best type of customer, make sure you really optimize for them first, gather all of those people and then make sure you are that answer and obviously kind of build from there. But that is kind of like for us, we're working with new customers or new brands. That's always the number one thing they realize is like you don't have to like build this giant SEO backlink profile like it used to be. Frankly, just needs to like have really be really good at what you do and explain that really well again with third-party authority as well.

I see. So I think it's changed a little bit. You could be, you could be a little bit more broader, right, with search keywords and maybe some long-term keywords. But now it's like you're not only optimizing for those keywords, you know, you're optimizing for, you know, a lot more detail in terms of what they're— the problem you're looking to solve.

And so Seems like that's the data. And I think to just be clear, it depends on who you ask this question. They've done a few different studies on this, but I think it's somewhere between 70% to 90% of those AI overview answers in Google are not from page 1 links, meaning they're not even in the top 10. It's because frankly, the top 10, if you say, I want the best coffee shop in New York City that has the best oat milk latte, the number 1 Google result is probably going to be Yelp or something. It's going to be something where it's not going to be that thing. It's not going to give you an answer. answer. It's going to be like, here's some things to search through and pour through and figure out. You don't want to do that anymore. Like, you're too lazy. Like, Gemini is going to tell you like, oh, the answer is this because they won this award for this and they are the best at this and they refined their craft and they have the best oat milk latte in the world. Like, they're going to, it's going to tell you. And that coffee shop might be on page like 4 of Google. Like, it might just be there, but you wouldn't have ever found it because, you know, you weren't really like, you weren't going to make it to page 4. You kind of like, it's like pouring through these other links. And so for us, like, we realized if you know that and realize that, If you know that you are the world's best oat milk latte, just lean into that heavily. Make sure that's all over your branding and all of your user testimonials and your reviews and like make sure that very clear to the crawlers coming around that that is your thing and then you'll win that area.

Love it. That's a really good approach to thinking how to position yourself. And maybe last question here, John, before we go into the personal rapid-fire questions, how are you thinking of maybe building your team, implementing AI, and maybe as part of the, you know, your marketing process or just As part of your growth process in your startup and maybe something that our listeners can also start thinking of implementing themselves?

I'd say that we dogfood everything we use. So we actually use all of our own tools. It's something that we actually built ChatRank for ourselves. We didn't even talk about that story, but JustReachOut, our other business, was doing very well, mostly on a content marketing channel, like an inbound channel. So very much we did very well with SEO. We did very well with just getting people to come in. We did pay for ads as well. And so all of a sudden, it was August of 2024. I'll never forget this. All of a sudden, our inbound channel kind of just came to a halt as Google stuck a giant AI overview on top of our core search page. And so that was like the aha moment for us to realize, like, well, we're not going to survive if like our number one blue link we worked so hard for was just buried below this massive, like, answer they were giving that we weren't in. So we're like, how do we get into that? Like, how do we get into that? Because that seems free. And also, if we can get in there, that seems to jump all the rest of this. And so we built ChatRank for ourselves to go do basically what we needed, which is to get into the AI overview. So everything we've always built and done, we've built for ourselves and we've used ourselves. So we use JustReachOut to get ourselves press and PR. We use ChatRank to kind of help us rank better in the AI tools. And so for us, we are always looking for ways and creative things to do to kind of integrate AI into our processes. Now, of course, from an engineering perspective and a coding perspective, yes, we do use Different AI, like, coding agent decoding tools to help us, like, do build, like, some of our things. Like I said, core and foundational to us, it's like actually understanding and being good with design and user experience and making sure that you actually have a good thing for the user to use. It doesn't matter how good your product is anymore. Like, anybody can kind of write code like that. That's not the hard part anymore. The hard part is giving a good user experience that tells them, like, gives them what they need and actually gets some results. Like, for us, like I said, because we use it ourselves every day, if we don't, if we're not getting results from it, it's not going to go into the product. So we all have customers asking for this feature or that feature. We're like, no, we don't— that doesn't matter. Sorry. Like, I know it might matter to you, but I promise you it doesn't matter to get you another sale or another user or another patient. So like, we're not going to build it. And so just having the clarity and understanding of how to do that, like use the AI to your advantage is always helpful for us. And we've kind of been able to build that way.

Love it.

Yeah.

I mean, you're essentially solving your own problem, you know, using that for your own growth and you're like, hey, try to use this. You're like, hey, we probably already tried this before. We know it's not going to work. We're not going to waste time on this. So that's good. That's your wisdom and your knowledge and your experience that you're able to To say that as marketers yourselves.

And we know that, for example, with content writing, AI in content writing is interesting because a lot of people say, oh, if you have AI write your content, it's going to get flagged and you're not going to rank well and it's going to kill you. And the answer is, I mean, maybe a year ago that might have been true, but it's actually not anymore. Right now, what AI in the newest Google release they gave in March, they're really penalizing AI-written content only using AI for the content, meaning you didn't add anything unique or valuable. It's just repurposing what AI already knew. That's the AI slop they're calling it. So basically, if you are just going to ChatGPT and saying, write me a blog post explaining why I'm the best CRM for HVAC companies, it's just going to write you a blog based on information it already knew because you didn't give it anything from anything really relevant. It's going to write you a blog of things it already knew about, and you post that. It's not going to be helpful. AI is going to see that page and be like, I wrote this. I knew all this already. There's nothing interesting there. But if you have the AI help craft messaging, this is what ChatRank does extremely well. We actually help our customers do exactly this, is Hey, what are your unique insights on this topic? So we already have, we know how to write this, this blog post, this piece of content really well for you to optimize for exactly what you care about, what you need in AI search. What we need from you is a data point explaining like how you'd get return on this, you know, a user testimonial, a quote from your CEO, another data point around this topic here. Give us those 5 things. Let our AI then help craft really good messaging and writing using your brand voices and your brand kits and everything else that matter to you. So we'll help you craft like, you know, AI, call it AI helpful, helped written content, but you are providing these unique insights that AI would have never known otherwise. When AI goes and crawls that information, they see, oh, whoa, I didn't know this. I didn't know that. That's something interesting. Now you're seen as an authoritative source in that area. That is what's really standing out now. That's what really matters. And so for our customers and for really anybody we talk to, that is the biggest myth right now. It's not just human written versus AI written. Is it relevant or interesting or novel or unique? That is what really matters. And it reinforces what you say. That is the most important thing you can do right now As you're thinking about using AI to help with your marketing, your content, or your website, whatever that might be.

Love it. So you're building in that uniqueness and interest part, but you can only get that as part of your— inside your business that you only know. And you have to be able to pull that out from your day-to-day business, get that data, present it to AI. It's like, hey, this is more information that you probably don't know, and that's where you can really shine and stand out. Love it.

Exactly.

Yeah. John, this has been great. I'd love to shift gears and move towards the rapid-fire questions. You ready for that?

Let's do it. I don't know if I'm ready, but let's do it. Let's do it.

John, what's one activity you enjoy outside of work that gets you into a flow state?

Ooh, into a flow state. I love cooking. I'm a big— I don't follow recipes ever. I just like to, you know, I go with what I have. My favorite is like the pantry meals. Basically, you open the fridge, you open the pantry, and just go, what do we have today? Like, I haven't gone to the grocery store in a few days. What do we got? And then like just build something from there. So, uh, my wife and kids, they like— I, I do enjoy kind of coming home after work and getting to, uh, you know, sometimes I have a thought about what I'm gonna like do. Like when I go to the grocery store on like Sunday, I get, I get the right things. But once I start cooking, it's like, oh, a little this, a little that, I'm gonna add this. And it's just, it's kind of fun to just come home hungry and just figure out what, what the, what the meal is that day and just kind of like flow through it. And that's like my, uh, I don't know, I feel like I get to do that more often than, uh, than not. It's really fun.

Love it. Yeah, I mean, you have the creativity to explore and put things together that, you know, you just having to think or plan for it. Yeah, love it. John, what's one piece of advice you wish you had known? If you can go back, you would tell your younger self, let's say your 25 or 20-year-old self?

I think what I would have told myself is to just really lean into relationships and building the network early. I've done a pretty decent job of it now over the course of my career to kind of like meet new people. Obviously, going to business school really helped with this part of my career. But I can't tell you how many, like how well social selling does for us. So it's, hey, I noticed that you were like, you know, this person, you know, this person, I'd love to get introduced to them. Do you think they're open to like a coffee chat or like a conversation just to kind of get going or just get started? No hard sell. No, like just, just how you learn from them. And this is kind of like I mentioned before about kind of talking to 5 customers a day, just building that, that muscle and that network of just having people you can reach out to. And if it's not them, it's one of their partners. I mean, just recently I reached out to a friend of mine who actually runs a small VC out in Cincinnati. He's like, oh, I need to introduce you to one of my portcos. And then he did. And then he introduced me to one of his friends. And all of a sudden, like, now we have 2 new customers out of it. Like, that is a way to kind of build and grow. For now is where, like, you know, again, growth hack, like whatever you can do. Obviously there are more professional processes we run as well. But this is something where I think early in my career I was really focused on how do I build cool stuff? How do I go out and sell it? How do I have some fun? It was like all about that. And then as I got a little older in my career, I realized, you know, relationships really do matter and like building those and kind of like for working those and maintaining them over time really matters. And so for me, that's kind of the thing I wish 20-year-old me had known.

Absolutely. Fantastic, fantastic advice. John, what are some of the biggest challenges you're currently facing in order to continue to grow ChatRank or just ReachOut? Meaning what keeps you up at night these days and gets you excited?

Yeah, I mean, I mentioned this earlier about how we decided to bootstrap ChatRank. I mean, just about every one of our competitors has raised an absurd amount of money, like a lot of money. On the lower end, it's like $3 to $5 million. The higher end is like $200 million. For like something that we've bootstrapped. And like, I know our product is as good or better than a lot of these other products, but they have a lot of salespeople and a lot of like horsepower, like, you know, firepower to go out and go try to grab this market. So I feel like we're on a really good path and we're growing month over month and we're doing really well and everything's like, we're tracking great. I'm not worried about our success at all. At the same time, like, it's a very, very crowded market. We have new competitors popping up Daily. I mean, it's like, I mean, I can't tell you, unfortunately, we looked up, there's like 5 ChatRanks and RankChats like now that are just, I mean, basically ripped our entire website and our entire product. They're kind of terrible. So like, we're like, it's, that's not a good thing. But like, there's so many people just popping up into our space. It just is, no, it's challenging to kind of stand out in that noise. How do you, how do you stand out? How do you find your niche? Even if you know you have a better product and your customers love you and you have such low churn and you're like, you're converting your funnel really well, like all those things are doing great. But at the end of the day, if there's like 100 other companies or hundreds of other companies saying similar things, it confuses the market and they're just like, either they go with somebody else or they just throw their hands up and go, I don't know, I'm not doing anything. And so it's been challenging to kind of fight through that. We're finding ways and kind of just maneuvering ourselves as best we can. But that's something that's just been challenging being in a space where when we first started, we were one of like 3 companies doing this and now there's literally hundreds.

Yeah, there's so much noise now to sift through as the user, right? And decide. So it's like whatever comes, whatever's in the moment and solved my problem. If it says the same thing, you might, you know, just might believe it, but you don't know.

And we can, we can tell immediately who byproducted this the weekend. It has no substance at all. And like, who, like, who didn't? And it's like, I mean, I'm not gonna say that we're the only one that do this well. There are other— we have competitors that are good. It's not like they're— we're the only company doing this, but there are probably, I don't know, 7 companies doing this well and probably 200 that are just noise.

Yeah, that's where you stand out. John, who or what are some of the best 3 resources? These can be books, mentors, Or people you follow in the space who you'd say have been most instrumental to your success over these last few years?

I've had a few great professors in my day that really were excellent for just helping me understand and see the light beyond where I was. I had a really good advisor and professor in undergrad, Dr. Naiman, who was just very good about just helping me kind of understand and see what was out there. And it was very from an academic perspective, but really opened my mind to Applied mathematics was all about just, I don't know, it was problem solving. At the end of the day, it was very much like, how do you solve a problem? And that was what it taught me. And so that has always kind of applied and stayed through my whole career. Just how do you approach a situation, not get overwhelmed or scared or nervous, just say, okay, here's the problem at hand. How do I solve this and how do I think through this from first principles, whatever that might be? That's always been really helpful for me. I had some great business school professors as well who are just like brilliant minds in the space. I had an M&A professor, her name was Emily Feldman. She was just so good at just explaining how companies worked and operated and did things. And it was very much a case method type of class, but it was very good about just like, why did Mark Zuckerberg and Facebook buy WhatsApp? You could read that case, you could read the data for days. There was nothing explaining why they bought WhatsApp for the price they did. And so, I mean, just hearing that kind of perspective and learning from that, just understanding, it was actually I had the quote unquote right answer according to our professor, who actually, by the way, was Mark's— she lived down the hall from Mark freshman year at Harvard. So she knew him back in the day. And I was like, I think it's just hubris. I think just Mark just wanted to buy them because they had so many users and he just wanted the users. And she was like, ding, I think that's right. She's like, I think that's actually the answer. So anyway, there's no real answer, but just the idea of just kind of thinking through How do people, these really successful businesses buy, sell? The failure stories too are just super interesting. It's just like, I loved her perspective on how these things can be done in a more business way, just how to think about, like, you know, it was in the lens of M&A, but it really applies to anything in business. And so that was always really good. And I've had some great mentors in my career as well that just have kind of led and grown me. And I mean, I'll shout him out, my co-founder Joe Delgado, who's our CTO and my co-founder here. He's just been excellent to just help me understand and be really thoughtful. He's like one of the best— I mean, he's the best engineer I've ever worked with by far, as far as just like technical chops. But then in addition to that, it's more just how do you think through these problems? How do you really lean into the customer needs and everything else? And so I don't know, these are always kind of just like interesting things to think about. And so Joe's been an excellent thought partner for us over the last few years through building these out.

Love it. Appreciate it. I'm sure he appreciates the shout out as well. So, John, what does success mean to you today, whether that's Personal, business, financial life? There's no right answer.

First of all, I love that we have the flexibility to build what we want to build when we want to build it. So we don't have investors breathing down our neck. We have the ability to kind of build what we like to. I like leaving work at 5 o'clock, going home and having dinner with my kids and putting them to bed. And then I unfortunately open up my laptop again at 8 o'clock and work till 2 in the morning. So that's just like, that's the founder life. You're not like, it's not like your day ends at 5. I go home at 5, have a breather, and like, not much of a breather. My kids are crazy, but like, you know, have a breather. And then after that, you know, you get to actually like, you know, I get my work done from 8 to midnight. That's how I like to joke with my wife. But like, that's the, I think that just for me, just having the flexibility and the ability to kind of just like, you know, like run these businesses the way we want to and really having the ability to kind of like live our lives in a fun way. I started my career as an investment banker on Wall Street. It was like, it was 80-hour crushing weeks, 7 days a week, just nonstop. glued to your BlackBerry at the time, like lifestyle. And I still have friends doing that. And like, listen, I know, no shame or anything like that. And I'm not going to say that like the entrepreneur life is glorious all the time. There are some good days, there are bad days, and the bad days are tough and the good days get you through the bad days, I guess. So I'm not going to say that there's like, it's all like glory and rainbows here, but it is just like kind of fun to just be in a position in life where we are building something fun and interesting. It's going really well and we're going to have hopefully a great exit one day if this all goes well and that it's going to be You know, all worth it. So I don't know, for me, it's not really money or fame or anything like that. Those are things that never really mattered to me. It's really just more about just kind of living the life I want to live and that Joe and I have the same ability here. I'm thinking through that and it's just, you know, that's just like where we are today and things might change in 10 years from now. But for now, this is kind of where we want to be.

Love it. Love it, John. It's been a fantastic episode. I enjoyed everything you shared and I'm sure our audience did as well. Where can founders get in touch with you, learn more about you and your company, chatrank.ai or justreachout.io?

Yeah. So, I mean, you gave the website there, it's chattrank.ai and justreachout.io. Check us out there. Tons of resources and learning about that, especially in ChatRank. You'd be surprised. AI search visibility, it's not just for, you know, SaaS. Like, if you're listening to this episode and you're like, oh, like, I mean, I might be able to use this, but also like my mother is an esthetician or like my cousin like is a small business owner, like those things, like let them know we're at a price point where we are, we will get a return on our investment. Like when you're using, we're working with us. we're going to help you win in this space. And so for us, like really anybody or anything you might be interested in, like learning more about it, let us know, kind of come to ChatRank. We have different landing pages for different industries and verticals we work in. You'd be surprised. It's all over the place. It's from some of our customer stories and wins. So I'd say definitely check that out. And yeah, if you have any questions, please, my email is jon@chatrank.ai. Email me directly and I'd love to hear from you.

Love it. Thank you so much, Jon. We'll add those links to the show notes and your email as well. Thanks for your time today. I appreciate you jumping on.

Thanks, Akeel.

Thank you all for watching this episode and joining SaaS District today. Don't forget to like, subscribe, and hit the bell for future episodes where we interview top leaders in the SaaS industry. If you're a SaaS company looking to grow and unlock the true value of your business, get in touch with us at Horizon Capital and myself or one of our consultants will provide a free assessment help you get there and hit your goals. If you have any feedback or suggestions for this podcast, please comment down below and help us improve our content for you all. Thanks again, and see you on the next one.