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Jon Mest (ChatRank): AI Visibility, “SEO Isn’t Dead”, and Bootstrapping a New Search Channel

Founder Views · 2026-03-03 · 1h 8m

0:00--:--

Key moments - from our scoring

Substance score

50 / 100

Five dimensions, 20 points each

Insight Density10 / 20
Originality9 / 20
Guest Caliber12 / 20
Specificity & Evidence11 / 20
Conversational Craft8 / 20

Jon Mest, founder of ChatRank and Just Reach Out, discusses bootstrapping two AI-powered SaaS businesses with overlapping customer bases and distinct value propositions. ChatRank helps brands gain visibility in AI search results (ChatGPT, Gemini) by optimizing their content - a strategy he argues is complementary to, not a replacement for, traditional SEO. Just Reach Out democratizes PR outreach for solopreneurs, small business owners, and enterprises alike, offering DIY alternatives to expensive agencies. Mest shares tactical founder-led sales approaches: identifying high-intent customer segments (e-commerce and medical verticals emerged as unexpected winners), building case studies from early wins, and using LinkedIn outreach rather than spray-and-pray email campaigns. He emphasizes the importance of taking every sales conversation - even seemingly unqualified leads - to uncover hidden ICP patterns and budget willingness. For bootstrapped founders, especially those selling mid-market software ($500+/month), his methodology of niche targeting via partnerships and opportunistic inbound, combined with relentless founder involvement, offers a replicable playbook for growing without venture capital.

Key takeaways

  • →Your ICP will likely shift significantly as market conditions change - ChatRank originally targeted B2B software teams but discovered e-commerce companies cutting ad spend through organic AI search traffic became their best customers.
  • →E-commerce and direct-to-consumer companies have fundamentally different marketing budget psychology than B2B SaaS, making them more willing to invest in new channels like AI search visibility.
  • →Founder-led sales through opportunistic inbound conversations and intentional outbound targeting to high-signal prospects is more effective than broad volume-based outreach when bootstrapped.
  • →Building case studies and success stories from early customers enables you to systematically target similar companies through partnerships and LinkedIn-based outreach.
  • →Eating your own dog food matters - ChatRank shows up well in ChatGPT and Gemini search results, which drives inbound qualified leads and validates product-market fit.

In this episode

  1. 1Jon's Background: Wall Street to Entrepreneurship
  2. 2Building Just Reach Out: From Managed Service to AI Software Platform
  3. 3ChatRank's Evolution: From B2B SaaS to Multi-Vertical AI Visibility
  4. 4Finding Product-Market Fit: Identifying Your True ICP
  5. 5Bootstrapped Sales Strategy: Founder-Led Outbound and Strategic Partnerships
  6. 6Qualifying Customers: Learning from Unexpected Opportunities
  7. 7The Reality of Founder-Led Sales and Customer Obsession

Mentioned

ChatRankJust Reach OutJon MestTech M&A1010 DATALinkedInChatGPTGeminiGoogle AdsDimitriJoeJohn

Guests

Jon Mest

Topics in this episode

founder-led salesGoogle AdsChatRankJust Reach OutAI search visibilityLinkedIn outreachAI searchBootstrap fundingJustReachOutE-commerce customer acquisitionLinkedIn outbound salesSEO versus AI search channelsBootstrapped SaaS business modelB2B software marketingGoogle Ads and SEO budget reallocationSEO versus AI searchPR and press outreachAI visibilityJon Mest

Questions this episode answers

What is ChatRank and how does it help with AI search visibility?

ChatRank optimizes brands' content to appear in AI search results on platforms like ChatGPT and Gemini, helping companies reach users who query AI tools instead of traditional search engines. It's positioned as a new marketing channel that works alongside SEO, not as a replacement for it.

Who are the best customers for ChatRank and what budget do they need?

E-commerce and medical companies are current growth leaders because they understand customer acquisition costs and marketing spend ROI. While ChatRank's base plan is $500/month, the ideal customer varies by vertical - a small e-commerce business with $30k+ monthly marketing spend may be more qualified than a larger SaaS company indifferent to marketing tactics.

How does Jon Mest approach sales and customer discovery as a bootstrapped founder?

He conducts founder-led sales using LinkedIn outreach with premium accounts to reach targeted prospects, builds case studies from early wins to validate messaging, and takes every inbound opportunity seriously - even seemingly unqualified leads often reveal hidden customer segments and willingness to pay.

What overlap exists between ChatRank and Just Reach Out?

Both companies share the same core team (three founders), customer base, and synergies - many customers use both tools. Just Reach Out handles PR/media outreach and brand building, while ChatRank handles AI search visibility, allowing cross-selling to trusted existing customers.

Is SEO dead with the rise of AI search, according to Jon Mest?

No; Mest positions ChatRank as a complementary channel that coexists with SEO. AI search represents a new, growing pool of potential customers, but traditional search optimization remains valuable and budgets are being reallocated rather than eliminated.

What our scoring noted

Our reviewer’s read on each dimension, with quotes from the episode.

Insight Density

10 / 20

The episode contains real, actionable nuggets - AI crawlers can't render JavaScript, AI overview citations frequently skip page-one results, and AI-sourced traffic converts at higher rates - but these insights are diluted by long stretches of mutual validation, rambling sales philosophy, and basic bootstrapping advice that any operator already knows. The insights-to-filler ratio is roughly 1:3.

OpenAI's AI crawler is like Google 1998. Like they're just so bad at reading a website they don't really know how to do it to the point where like these crawlers like still won't render JavaScript on your page.
it's anywhere from like 50 to some people say claim even 90% of the answers in the overviews do not come from page one links

Originality

9 / 20

The weekly AI-tool-rotation policy for the whole team is a genuinely fresh operational idea, and the 'uneducating customers' framing is useful. But the core AI-visibility argument - quality over quantity, be authoritative, answer engines differ from search engines - recycles what is already loud discourse on LinkedIn and is explicitly acknowledged as noisy. Most of the bootstrapping philosophy is textbook.

we as a company have a policy where we are all supposed to change our primary tool week to week
a lot of our first calls with customers, our potential customers, is mostly education. Like, if we get to a demo at the end, we're happy

Guest Caliber

12 / 20

John Mest is a genuine practitioner - actively leading sales calls, running two bootstrapped software companies in the exact space discussed, and speaking from direct customer data rather than theory. The limitation is scale: 25 - 30 people total across both companies constrains the depth and stakes of his war stories.

my days, I mean my wife wants to kill me for this but like my days are like I'm, I'm on calls with customers from 8:30 to 5
we kind of did a little interview with, with their team. We realized that but they realized by using Chatrank was they were getting so much more organic, high intent... they actually cut their ad spend down

Specificity & Evidence

11 / 20

There are several strong data points - a tire vendor spending $2M/month on Google Ads plus $30K on SEO, Profound raising at a $1B valuation 18 months post-founding, named customers like 'Megan,' and the med spa Saturday-hours discovery - but most case study outcomes are vague ('cut their ad spend significantly,' 'a ton of money on PartnerStack') without hard before/after metrics or timelines.

online tire vendor. Massive company. So they're spending. He said, I was spending, like, almost $2 million a month on Google Ads and spending 30 grand a month on SEO.
profound is one of our biggest competitors. They've raised at a billion dollar valuation. Last week they just raised their now unicorn 18 months after starting.

Conversational Craft

8 / 20

The host lands a few genuine follow-ups - pressing on which falsehoods are circulating, probing affiliate channel ROI, and asking about attribution methodology - but undermines momentum by repeatedly validating every answer with 'amazing,' 'that's so true,' and 'that makes a lot of sense,' and never once challenges a claim or asks for harder evidence on outcomes.

Can I, Can I stop you? There for a second. What are some of those falsehoods that you're seeing online now?
That, that's so true. I can totally relate to that.

Conversation analysis

Computed from the transcript - who did the talking, and the words that came up most.

Share of words spoken

  • Jon Mestguest86%
  • Kostahost14%

Most-used words

customers45google34sales32brand29answer26customer24team22reach21call21page21channel20first19trying19different19search19marketing18

Episode notes

AI search is changing how buyers discover products. But most founders are either ignoring it, or getting sold misinformation. In this episode, Jon Mest ( and breaks down what actually drives “AI visibility” and how he’s building two bootstrapped companies in a market that’s shifting weekly. We get into the real execution behind: Why “pump out 1,000 blog posts” is bad strategy in AI search What AI models struggle with (and the on-page fixes that matter right now) The off-page signals that influence AI recommendations (reviews, Reddit, YouTube, real human sentiment) How Jon sells a $500/mo product without spray-and-pray outbound Partnerships vs affiliates, what worked and what completely failed (PartnerStack experiment) Why podcasts are underrated for both backlinks and AI citations Jon’s “rotate AI tools weekly” habit to stay sharp across models Why bootstrapping beats VC for most SaaS right now (and when he’d reconsider) If you’re a SaaS founder trying to understand what’s real in AI search, this one will save you time and mistakes. ️ The Arena The Arena is a private Skool community for SaaS founders who are actively building and selling.

Full transcript

1h 8m

Transcribed and scored by The B2B Podcast Index.

Kosta: All right, we are live. John, welcome to FoundReviews. How's it going?

Jon Mest: I'm doing great. Costa, how are you today?

Kosta: Very well, very well. Um, really excited to have you on and have a discussion here. I know we just briefly met via email, but, um, if you don't mind. John, kick it off. Uh, for those who don't know who you are, just take, uh, a minute or two, introduce yourself, your background and what you're up to today.

Jon Mest: Absolutely, yeah. So John Mest, originally from the Philadelphia area. Um, went to school down in Baltimore. Studied applied math, data science. Didn't know what I wanted to do with my life, but know I wanted to move to New York. So I ended up on Wall street for a couple years doing investment banking at Tech M and A. It was a fun ride, but not the long, uh, game for me. Exactly. But so learned a lot there and actually learned about the company. I ended up joining, um, in New York called 1010 DATA. And there I was actually there for about six years. Got started as a data scientist, rode through sales, engineering, customer success, product roles. I've kind of wore a lot of hats in my years there. Saw, um, them through acquisition, which is a lot of fun. Did a couple years in business school, and then ended up where I am today, which is where I founded a few companies. Now we currently are running Just Reach out and Chat Rank, which I'm sure we'll talk about today. But it's been a really fun ride to kind of both learn from really great people over my career and then be able to actually start something on my own. Uh, uh, post business school.

Kosta: Amazing. Okay, so currently you run two companies, Just Reach out and chatrank?

Jon Mest: Yep, my team and I do, yeah.

Kosta: Okay, um, which one did you start first? It was just Reach Out. Right.

Jon Mest: So just Reach Out. We partnered with the original founder of the business. It was interesting cause it was more of like a service business that they were kind of. It was a managed service. It was really not a software company. It was more like a managed service business. No big. Been around for about 10 years by the time we, we came and partnered with them. Um, and the original founder, Dimitri, is great. And so we, we were kind of working with him on, on advancing it to a more of an AI software self driven platform. And so we did that and then we ended up taking over the business that was more like a kind of. We absorbed and brought on the business that was kind of already existed and had a brand name, but we built the actual tech and software and the business around that, um, chat rank, we truly built ground up zero to one. That was the uh, the, the second business suite we brought on after that.

Kosta: Okay, and do the two companies, are there overlap or do they operate completely separate or legally?

Jon Mest: Technically like they're separate entities. But yeah, there's a ton of overlap and so many of our customers are customers of both for exactly that reason. I'm sure we'll talk more about that. But there is a ton of synergy between the two companies. And what I've learned over the years, and I've been, I mean you learned this in a textbook in business school, but also just seeing it live is once you acquire a customer and you treat them well and they like you and they like your software and they like what you're doing, you, it's that much easier to then convince them that your next project is going to be worthwhile to them. And so cross selling to existing customers is just so much easier. Not because like you forcing the user or anything like that, just because, you know, they do trust you in the brand and they really respect that. So that, that has definitely been helpful in our, in our journey.

Kosta: That, that's so true. I can totally relate to that. If you. Yeah, I mean as they say, right. People don't buy the product. In a lot of cases, they buy the people. Um, and who's behind that and building that trust?

Jon Mest: Uh, yeah, people always, yeah, people always say, well, obviously you have to treat your customers well and we're customer obsessed, all those things. But like if you aren't actually that, you'll learn really quickly when you try to sell them another product and they go, nah, nah, I'm good. Like you'll know right away if that's the case. We didn't experience that. But you can tell like when they don't have that same passion for you and what you're building or the opposite of that, which like, hey, when we're starting Chatrank, we're starting something new. I mean we had to line up the door for beta testers to try it out and like see what we were building.

Kosta: Yeah. Okay. How big are the companies in terms of team size? I don't know if you share revenue numbers, but just to give a sense of where you're ah, at.

Jon Mest: Yeah. So we don't usually share revenue numbers only because, um, we bootstrap both these businesses ground up and uh, it's called the vulture. Capitalists are circling and they're always looking for sound bites on these things.

Kosta: I've never heard that before. That's a good one.

Jon Mest: Sorry. So that we've, we've like, so we kind of don't share that. But as far as team size, I mean, there's myself and the core partners. There's three of us that are the core team that are kind of running things. I run most of our sales and operations. My co founder and cto Joe, he runs all of our technical work. So we all, we all have a technical background, but Joe call it, writes the code. I do most of the sales and go to market and marketing and operations. And then we have another partner, John, who does a lot of the, uh, product and you know, more like, you know, thought leadership type of stuff around these spaces in the AI world, that's the core team. And then we have a bunch of people on sales, operations and other areas in engineering. Um, underneath there the team's about, gosh, I should know this, like 25 or 30 people now in total between the two companies. But the three core of us are the three partners and founders.

Kosta: Same partners with both companies.

Jon Mest: Yep, exactly.

Kosta: Okay, with just Reach out, how long were they around before you took it over?

Jon Mest: Yeah, the business has been around since 2016, so they were around for 2015 actually, I think when they technically started. So It'd been about 10 years before we came in and took over the business, like I said. So it had a good brand, it had done really well over time. But I mean they just were. It's hard to scale something that is very human driven and kind of managed service driven. But really the idea of just Reach out is still very, very valuable. It's that the idea that if you're a business and you need PR and press for your business, you can either one, go out and hire a very expensive PR agency, two, you can go buy very expensive software that the agencies use. But you as a business don't really have, you know, 20, 30 grand a year to like spend on a software that you, you like, you don't know anything about. So what we do is offer the kind of the business owner, the nonprofit leader, the salesperson, the single entrepreneur, the person that wrote a book, an opportunity to like do their own PR and actually go out and grow their brand and grow their awareness. And we charge, you know, like a tiny fraction of what an agency or what these other tools would cost. And so that, that the idea of that has always been relevant to be able to do your own pr, because nobody can tell your story better than you can. But having an accessible software that does that, well, that was something that we really felt passionately about and it came from our own experience as well.

Kosta: Okay. No, that. That makes a lot of sense. And do both companies, are you targeting the same audience? Like small, medium, M sized businesses or.

Jon Mest: So it's funny, because of our price point, people assume that we are just kind of SMB, you know, smaller, smaller businesses. But actually we work with, you know, large, like very large, like public companies all the way down to like individual entrepreneurs or solopreneurs doing like something on their own. Like, it really does vary, I'd say, for just reach out. A lot of the people that do love working with us are people that are trying to build a brand. And so that might be like, hey, I just wrote a book. I want to go promote it on podcasts or to different blogs and substacks, things like that. See, that might be a single person, but they have an initiative. They just wrote a book and they want to promote it. That's a big deal. Like I said, we also work with large public companies. Um, we actually just talking to one this morning. Similar thing where they're a massive travel company. Like I said, a public company. They're using just reach out to, um. And so it really doesn't necessarily have to be a small company, although just based on our price point, it is very accessible to the smaller companies.

Kosta: Yeah. Okay. All right. And now and with. With. For Chatrank rather, um, who do you generally. Who's the ICP there? Like, who benefits the most from using ChatRank?

Jon Mest: This is a kind of a loaded question, so I'm smiling, but I will answer it as succinctly as possible because it's changed a lot. The space of ChatRank where it's really helping brands be more visible in AI search. That idea has just evolved so much, so quickly and changing all the time that our original kind of what we thought was our core ICP and is still a great customer for us today might not be our growth lever going forward. So we've kind of established and realized this over time. So originally it was a technical type product and team and they have marketing opportunities that they want to go after. And they know that their customers, because they're selling a technical product, they're the customers using AI. And so what two years ago we were doing this, that was our core user was like that called B2B software or B2B kind of company that knew that their customer was searching through AI for their answers. And that's where they're going after now. As AI has proliferated to way More people like my mom who uses AI. Everybody is using these AI, uh, chat tools especially now. It's really about who's trying to access as many people as possible, knowing that the pool of people that are seeing these AI answers is growing by the day. So now it's medical offices, e commerce, direct to consumer type companies, you know, consumer apps, people that are trying to acquire users and customers at scale. Those are some of our best customers now. So our ICP has changed, um, a little bit from there. And so we can still service the original kind of core customer we had, and we still do, and they love us. But going forward we really realize there's an undertapped part of the market around these, these businesses that know their customers are now using AI more than they ever have, but have no idea how to tap into that as a brand.

Kosta: Okay, so, so then like as a bootstrapped founder, uh, who's responsible for the sales and marketing, um, do you find it simpler to sell and market to like a niche, specific audience as opposed to like, you know, a broad audience? And like, how do you, how do you like decide or test which segments stick well with, with your products?

Jon Mest: This is the million dollar question. The billion dollar question, I guess around, like, how do I, I mean, because we're doing mostly Fonda led sales at this point. We do it, we do have kind of sales execution people for the most part. I'm leading sales efforts, um, for a lot of this. Um, and so for us, I'd call it, there's kind of two parts to this. When we're outreaching, we're trying to figure out who we're going to go after and like actually go like intentionally go after a certain group. Then yes, we obviously, we have our core areas we know do really well and we actually, we do two things. We find really great partners in those areas and we go after them tactically ourselves. So that would be, like I said, like medical and E commerce are two great ones for us right now that we are tactically going after via both partnerships with like, you know, other agencies or other people that are well established in the space, as well as, you know, our own like outreach team that is doing that. But then we're always opportunistic when, so when something comes in the door, oh, a friend of a friend or somebody saw us on chatgpts, they were searching for this and they're coming to us. Like we're very opportunistic with who we can serve because we know that the tool does work for everybody. But um, yes, it is a challenge when we're trying to figure out who we, how we should be spending our time on the outreach. Yeah, finding those really targeted areas is much easier because again you can build case studies around it, you can build a profile around it.

Kosta: Yeah. All right, so, so a lot of the listeners here are bootstrappers like myself and they, they, you know, I try to extract as much tactical um, insights as possible. So yeah. So how does your sales look like? Do you do outbound? Do you have a sales team? Is it uh, like you're doing this podcast? Obviously this is a form of marketing. Like what does it look like on a day to day, what channels rather are working the best?

Jon Mest: Yeah, I'll answer very tactfully. I actually do want to kind of share what we're doing because I think it is actually helpful for anybody really that's bootstrapping a business. And I think the first part of this is realizing when you are bootstrapping. Somebody taught me this when I was 23 years old when I first joined 1010 Data in New York and I was a brand new baby face kid joining the business world and I was joining a sales team for the first time. So I was a developer and they were like, hey, go out and sell some stuff because you're good at talking to people too in addition to your work. So they shipped me off to Cincinnati and I was working with PNG directly in their headquarters. Like it was just a crazy experience. I was three months into the job and they're like go do this project. Um, but anyway, what you realize really quickly is like you have to really confidently know what you're selling and to who you're selling it to and be really, really under, like understand that fully to get and like really be able to actually sell that directly to that person and feel confident in that. And so for us we really know, hey, these kinds of customers are really, really good and really effective. That is us talking to our existing customers and figuring that out. Like I said, we cast a wide net at the beginning. But then we realized over time, like for example, an E Commerce customer we had was really, really, really having a ton of success and we leaned into heavily why what was happening, what were they able to do? And so we kind of did a little interview with, with their team. We realized that but they realized by using Chatrank was they were getting so much more organic, high intent. So search traffic onto their website to actually, they actually cut their ad spend down. So we thought we were selling you like hey, This m. New channel. But we realized also is it's a new channel and we were able to get them to actually cut their ad spend significantly and still grow their sales through their organic channels instead of like their Amazon or other. Other places, um, in that, in that area. So of course we wrote a case study on this and started pitching that to like all of our. To that, that um, called that that group of users, that group of uh, of. Of kind of like potential customers or people similar to that. And so then we do have an outbound strategy around that. We have a. We have people that kind of go and look on LinkedIn who might be interesting or relevant to. To reach out. To go reach out to them with print, with DMs. Like, I mean nothing. Like, I love how LinkedIn doesn't really let you like kind of use bots to do this. You kind of have to like be thoughtful and tactful about how you do this. Get like a LinkedIn Premium accounts like a hundred bucks and just go like, find people that are relevant, like similar and then attack them as best you can. So we didn't go out and send like 5,000 emails to a email list I pulled from some tool. Like that's not really relevant. Um, we did do is actually be really thoughtful about who else might have the same problem, the same issue and then go after that specifically. So that's kind of like one area and like, I'm sorry, I'll pause there and then I'll. I can.

Kosta: Yeah, no, just, just to go in on that a bit more. So like chat rank just on your pricing page. You have a couple plans. The lowest plan is 500 per month. So uh, is this more uh. So this is obviously not like um, you know, like a general volume outbound play where you're cascanette. You're being a lot more uh, precise and methodological on like who you're targeting. Um, so. So is that accurate? First of all, like, it's not like a volume kind of game or like where do you intend to, how do you intend. Where do you intend to, uh, like be and grow as a company?

Jon Mest: Yes, you do. You do put thresholds on your kind of like, okay, they have to have a certain number of like a certain metric in order to be able to afford, call it $500 a month to invest in marketing in this channel. So yes, there is that level. But what I'd say is that actually it could be. It really differs depending on um, the size, like the type of company they are and what they do. So for example E commerce, they're very, very used to spending money to acquire customers. If you want to sell great T shirts online. Like you know if you sell your t shirt for 30 bucks, you know it's going to cost you maybe 10 to acquire that customer and you hope you can repeat sell to them because then you've already acquired them. But like at minimum you know it's going to cost you some amount of dollars to acquire that customer. That, that's pretty normal. When you go into like a B2B SaaS company like actually they might not have that calculation in their head. They're just like I need to acquire like eyeballs or they might not really be that tactical about spending and marketing. So actually selling 500 bucks a month to a small, it might be a sub million dollar a year. Like you know, pretty small E commerce company might be much, much more willing to spend the 500, the 500 bucks a month than like a $10 million software company that just like doesn't get maybe like they understand that you have to spend money on marketing. So like there's always like weird things like that where yes, it's going to, if it's going to end up being the same price point, go after the customer that's willing to spend the money. Like actually it's like uh, okay and understands that. So for us our thresholds for how big, sorry E commerce companies to be is much smaller than say how big like a software company might have to be to do that sale. And so you ask is it casting a wide net? Is it more targeted? It's both but I'd say that we can be very tactical vertical by vertical, knowing kind of what they're already spending. Oh they're spending 5k a month on SEO. It's just not working well. Great, let's go take some of that budget and like explain to them why reallocating that budget will be good for them through chat rank. That's a, that's a, that's a winning prospect.

Kosta: I mhm. Find when you're bootstrapping it's very, I'd say very beneficial to just speak to as many people as possible potential clients as possible even if they're not technically qualified. Uh because early on you're trying to figure that out and there's a lot of value and information you can gain from just speaking to everyone and doing demos with everyone. But you get to a point where after enough conversations, iterations in the product you kind of funnel down to like you know, who Your core audience is, and who benefits the most. And then you naturally should probably start to qualify. Um, who even comes through? Uh, do you do any. Does that resonate with you? First of all, how do you guys qualify, um, during the sales process?

Jon Mest: Yeah. So I'll give you two quick examples of that. So I got to give a shout out to Megan. She was one of our earliest customers in E commerce, and we thought she was way too small to be clear. Like, we. We thought this was a sales unqualified lead. It came in through a one of. Just through a website. Just like, she booked a demo. She comes on. And we thought her site was pretty small based on the metrics we were seeing. And it was. But she had, uh. She didn't blink an eye at spending money on marketing because she's like, I mean, AI ate my lunch. Like, all of my, like, ads aren't working. All of everything I'm doing is just, like, dying. I need a new channel. I need a new way. And so she made a. She was willing to make a bet on, like, our price point. Like, even though, I mean, her business was doing fine. It wasn't, like, zero, but it was like, it was below what we thought was our threshold for E commerce. And it made us rethink who we should be talking to in E commerce. And we realized it doesn't need to be a $10 million business. It can be much smaller than that and actually, like, get to, like, you know, really, uh, understand, like, what that she needs and what price she'd be willing to pay. And so we figured that out, and it was. It was a good match. And so we'd, like. We realized there, like, yes, that conversation, which we might not have ever gone after because it opportunistically came in our door. I took the call and, like, I just learned that ton from her, and I realized her struggle. I was like, wow, this is a massive opportunity in E commerce. That was. Kind of led the charge there. On the other side of that, we had a similar conversation. Person, um, found us from an inbound channel. So we think we do. We do. We eat our own dog food. Like, we do really well. If you go to, like, a chat, CBT or a Gemini and ask, who does this? Well, we do show up a lot. Um, so another company came in through an online tire vendor. Massive company. So they're spending. He said, I was spending, like, almost $2 million a month on Google Ads and spending 30 grand a month on SEO. And I was like, what are you spending $30,000 in SEO for. And he was like, I don't know. But compared to my overall budget, it's nothing. And so I just, I keep spending it. So that also made us realize like there's a certain type of e commerce player, um, and this wasn't like the largest type of e commerce like vendor, but just the ones that like they know how to get converting customers. And so that's another example of somewhere where you understand like they have these massive marketing budgets because the whole company is a commodity business. It's about marketing. Those people are much more likely to invest. And again we wouldn't have probably realized that. Maybe we'd have figured out over time, I guess like over the course of like reaching out to different companies. But really for us like having the conversation, learning from that customer on that, that that call was so important. And so to answer your question like more succinctly, um, uh, taking as many of your bootstrapping a company, taking as many at bats as you can, talking to customers is so valuable. My days, I mean my wife wants to kill me for this but like my days are like I'm, I'm on calls with customers from 8:30 to 5. I go home and spend some time with my kids, put them to bed and then I open up my laptop at 8 o' clock and start my work for the day. Like that's kind of like how my days are these days. But like that's the reality of like when you're bootstrapping and you're still doing founder led, um, sales. That's just the reality. You have to spend your days like talking to customers.

Kosta: Yeah, that sounds exactly like my days by the way. Um, um. So, so you're, you're still doing a lot of the demos and sales yourself?

Jon Mest: Um, um, yes. I mean I have, we have a team now that like helps with demos and alcohol, that kind of thing. But I at least join the calls at minimum to like actually like listen in, um, as many as I can. I mean I'll be, I can't join every one of them but like I do join as many as I possibly can because we are learning a lot from them. Um, and I'll also mention like it's not just customers, there's a lot of partnerships we're looking to build as you're bootstrapping, at least for us. Um, I kind of like learned this when I was like again in my early 10, 10 days when we were like again it was very much the ethos of like you exist tomorrow because you sold A customer today, it was very like, you work hard and drive because you want to continue on to tomorrow, and the company's doing fine. By the time I got there, it was like a $20 million business by the time I joined the company. But, like, you know, it was. That was still the ethos, like all that time later. And so for us, uh, we realized that partnerships are a great way to do that. You find the right partner, they'll go resell it for you. Instead of having to hire a salesperson, which you might not have enough money to go hire a big AE or like, hire a real salesperson. If you can train and onboard a good partner, not waste your time with a lot of partners, but, like, find good partners, they can be hugely beneficial for us. And so we've taken that approach here. And so I will definitely invest in relationships and partnerships with the right kinds of partners. Now, to be clear, some people like to just, like, kick the tires and like, you know, figure stuff out, but you can kind of suss it out pretty quickly as a, as a founder. And when you're bootstrapping, it's been a great channel for us, is finding a really good player in medical that like, recommend their clients. Same thing with E commerce. Same thing as other goals as well.

Kosta: All right, so you mentioned partners. Partners a uh, few times. Is that your. Would you say your primary channel at this point is partnerships?

Jon Mest: Um, our primary channel is still direct. Like, that's still our main, our main channel. But I will say, like, if you go to a. For example, for us in marketing technology, so a good marketing agency might do, you know, website design content, they might just do a bunch of things and they might even do paid. Like, they'll be like a paid or performance drag marketer. So they'll do all your Google Ads and meta ads, things like that, but they won't touch organic. Like, they just don't do organic. And they usually would just outsource to an SEO agency or somebody else to do their organic side of things. Well, approaching those types of agencies and explaining, like, what you can do how, uh, you can be partnered with them being flexible. So we'll like white label for these agencies. Sometimes we'll just do whatever it takes to kind of like, you know, give them what they need. That is another channel for us because now they have, call it maybe 200 customers or 200 clients on their book at any one time. The next, like, monthly meeting, they're going to be so excited. They're always looking for something to sell their customers or kind of give upsell their customers. We're happy to put you in the next slide deck and say, well, you should like think about chat rank too, because here's what they're doing and we really recommend them because again, they either vetted us and somehow tried this on a couple customers for us, whatever that might be. And so for us, we really like lean into that as a, uh, channel as well. Because if you can train a partner, well, I mean, and we, I'll just be honest, we pay handsomely. Like, we, we pay aggressive commissions to our partners because, like, it's still good for us. They're basically doing the selling for us. They have this book of business. Get them excited by giving them like an aggressive commission. And it's been working out really well.

Kosta: Okay, so, so just to be clear, you say partners. These are like affiliate partners or more like white label partners that are reselling your product for a recurring rate or all the above.

Jon Mest: I mean, we do both. We're pretty flexible. And again, that's on purpose. Yeah, we don't know what we don't know. The safe space is still so young. We are happy to take the affiliate model. That's nice. That's the easiest model. Like you just get paid every month when they stay as a customer, which is, which is great. But a lot of these agencies really love the high touch and some of them will even just. We'll train them on our software. They'll become experts on chat rank. Then they'll go sell packages to their clients for whatever they want. They'll have the services team. Like, we don't really want to do services. Like that's not our goal here. But we will kind of white label behind the scenes, let them do that for us. And then we just kind of do a rev share with them that way.

Kosta: Yeah, makes sense. Um, on the affiliate side, do you find most affiliates are tire kickers? Do you see anything meaningful on the affiliate side?

Jon Mest: Um, I was recently burned by this, so I will just be blunt and honest here. I find, uh, the true affiliates that used to be how affiliate networks worked are just gone. It's so hard to find people that actually meaningfully want to learn about your product and resell it to their audiences. Like that is just so rare. They still exist. So I don't want to say they don't exist. I don't want to say that the affiliate channel is completely dead. But having just gone through like, I mean, I spent like a ton of money on partner stack last year just like trying to get them just trying to make that work as a channel. I hired like a full time partner, like um, like a uh, like a affiliates manager. Like the whole, I did, I did everything they told me to do. I invested. It was our big growth engine for like 2025 was this like we have affiliates for our software because like I kind of read enough about it, I had heard enough people tell me about it and I went to them and I did this like pretty, pretty intensive like you know, push last year and just got nowhere with it. And like through the process I actually learned why it's that like it's just a bunch of people like stealing codes and putting your codes out there on random websites. And like it's just, you're just, there's really not, there aren't a lot of people that are actually willing to learn about your product, understand it, write a nice blog post or record a video and then take like a uh, like a rev share. Like it just doesn't work anymore. They either want a massive amount of money up front and we're talking like you know, 5, 10K for a YouTube video, like just, just for one video for an influencer doesn't even have that many followers. Or it's like they just want to code so they can stick on one of these code sites and then like that's just like the Monday.com, the HubSpot type places where like yeah, they don't really care, they just want more customers. They're just like happy to use the networks. But that's really the extent of it. Like if you're a smaller business like ours, like it just doesn't really work very well. And so I had, I mean I, I gave them my two cents about all this and like I had a couple meetings with them at the end and they were perfectly nice. I'm m not saying partner Stack is like a bad company, but like that to me I learned was like it just, the model just doesn't work for me or for our business because the affiliates just, it wasn't a good model. Like if you don't have like, you know, tens of thousands or hundreds of thousands of dollars to invest into like prepaying these affiliates. So we were, we struggle with it a lot, I'll be honest.

Kosta: Yeah, yeah, uh, I agree. Like I haven't had, I haven't spoken to many people including myself. I haven't had much success at all with affiliates and in any meaningful way. Um, now what about, let's talk about SEO or you know, whatever the acronyms are now GEO and, uh, leo. I don't even know. I can't keep up anymore.

Jon Mest: You said ll, M, E, O. Whatever it is. We call it visibility. We just say, like, you want to be.

Kosta: Let's talk about visibility.

Jon Mest: Yeah.

Kosta: SEO has obviously changed, uh, dramatically, and it's. It's changing before our eyes. Right? Like, what does that even mean anymore? How prevalent is the education piece of it? Like, you do you find there's still a lot of required education involved to your clients on, like, how it's changing? Why? You know, maybe SEO isn't a good channel to invest in and you should look at, um, alternative ways to be visible through AI. How, uh, do you find that as a.

Jon Mest: So there's a few different methods we've tried and messaging we've tried here. I'll try to, like, explain as best I can for the audience that you have, which is, you know, other business owners who are, you know, like, starting something here. So one, There is so much noise out there on this topic, and so much of it is just incorrect. So I just can't. I can't tell you how many people are just screaming on LinkedIn, just false things. Like, it's just. It's just crazy. And so a lot of the education we're doing is uneducating. People on what is not true and that you explain to them what is true. That is number one. So a lot of our calls, a lot of our first calls with customers, our potential customers, is mostly education. Like, if we get to a demo at the end, we're happy. But, like, we. It's a lot of people just coming to us, like, what is this and why? I heard this? Or somebody told me this thing. Just give it to me straight. And so we actually just, like, educate our customers. So we've never gotten off a first call where the customer looked at us and said, like, that was a waste of my time. Like, at minimum, they're learning about the space. And we do that again. It builds trust in us and what we're doing. And a lot of times they'll say, I'm talking to five of the companies, like, thank God you're the first one I talked to, because now I know exactly what questions to ask them because they're going to try to sell me some, like, thing that I don't really know if it's true or not. And so we try to always be really thoughtful about that process of educating our customers because it really is such a new space now.

Kosta: Can I, Can I stop you? There for a second. What are some of those falsehoods that you're seeing online now?

Jon Mest: Um, one is the just stuff as much like as many blog posts and information out there as you can on your own pages. And then just like, you'll win or just like Keep pounding like LinkedIn posts and like all these things and you'll just like, you'll just get like better. And so that if that works, it would last like a week and then it would catch on to it and just like dump you for that. It's not going to really like work. The idea of brand visibility and brand building and AI is, is there's a component of it which is like, you know, writing thoughtful content around your brand so you can people know who you are, what you do, and that you're an authoritative like voice on the, on the, on um, the. On the space. Like that has always been important. That was always important to SEO and it's still important to this new world of AI visibility. You need to be like authoritative leader in the space. But it's not just that anymore. Now it's also like the AI has unlimited information about, you know, like big things. It has information, but it doesn't always have really easy access to is real humans talking about you. Like, real humans like actually having a conversation about this topic. And so places like social media, places like Reddit and YouTube and LinkedIn, those are valuable channels as well. But it needs to be like real people talking about you. Your reviews. Like, so if you're a software company, G2 or Trustpilot, if you're like a restaurant, it's Yelp or something like that, those reviews really matter. Um, we've had like medical customers who had great health grade scores, which is the reviews they thought about. But their practices like Yelp review was bad because somebody like said the bathroom was dirty or something. I don't know, Whatever it is, it's like stupid. But like that was dinging them in AI search. Like this is what they need to be thinking about is like understanding like what is out there about their brand and then fixing those things, whether on page or off page. That is the most important thing that you need to be doing and thinking about. We call it like our five pillars. We have like the different things we know to work. Our system will recommend and make take action on those things. But like the misinformation we hear most is like, I just need to like pump out a thousand blog posts a month. By the way. You can go on and find a lot of tools Right now that you can pay money to do this for you and they'll happily take your money and do it. It's just not going to work. It's just not real, um, long term stability. And what it actually takes to grow in this channel in organic search and getting AI to recommend your brand is to be really thoughtful and mindful about your brand just being the authoritative source on a topic and having real people agree with you.

Kosta: So at the end of the day, what I'm hearing is the core concept is the same provide valuable content. It's not a matter of course, quantity, it's just like the quality of the content. Um, that's fair.

Jon Mest: So it is very similar in that way to SEO, because that's why again, the other thing that people always say is SEO is dead, which is just not true. Like the core idea of SEO like you just described is still very much alive and relevant. The difference now is that SEO was targeting for search engines. So you're trying to get Google to tell you when someone searches these keywords, like you want to get your pages or your website, like towards the top of that by kind of like basically stuffing or kind of making it seem like that page is the most relevant information that could possibly be had for that idea and then getting them to click on it and then learn more about it and read and find that out. Now if you are, um, ChatGPT or Gemini or Google's AI overviews, like you are now an answer engine, you're trying to recommend an answer. So when you're trying to recommend an answer, you take a different approach to what information you use and how you make that decision. Going to take a lot of information, synthesize it and then make a recommendation that you provide an answer. Now that answer, because you're an answer engine, like optimizing for that is very different than optimizing for the Google keyword. So that is the main difference between call it traditional SEO and this new visibility. And so the core idea of what you need to do to get there is similar. There's definitely some nuances and differences and we can go into them in more detail if you'd like. Um, it's much more specific. Every conversation in AI is a long tail keyword. Basically it's all a natural language conversation. So you have to like kind of know that and honor that. But at the same time that is the main difference and the main thing people miss. And so that's like the first thing we explain to our customers is like just you have to optimize your brand for that. And that's a different approach than just optimizing for SEO.

Kosta: M okay, that makes sense. And what about um, the actual on page stuff? Is there anything specific like syntax and table of contents, like any structural um, components that would be recommended.

Jon Mest: Yeah, I'll tell you that. So Google's in its own world because Google's just very good at this. Everybody but Google in this space, um, is just terrible at reading a website. So like I used to, I like to joke, it's like this is like OpenAI's AI crawler is like Google 1998. Like they're just so bad at reading a website they don't really know how to do it to the point where like these crawlers like still won't render JavaScript on your page. They just like don't really know how to like read a website and understand what it's saying. And so if you want to basically optimize your pages for AI search, you need to have these structured like schemas and things like that available on your page. So that's kind of the core technical SEO stuff that's always mattered still really matters to brands. Because for example, like I said, like if you are like trying to get your content relevant in AI search, it's really easy if OpenAI's crawler can just, or Perplexity's Crawler or Claude's crawler could get on your page and just really easily find the information it needs and get at least an overview, like an understanding of what this page will be. It's so much more likely to then use that page or use you and not just skip you. Um, so like page load times matter like where the syntax of your page matters, schema matters like all these like headers and things like that, so it can easily structure data, all really matter. Moving your call to action near the things that would lead them to call to action, like those snippet worthy content. That's really important too. Like these things all matter to the AI crawlers are trying to read your website because um, they're just again not very good at reading websites. So right now that is still a big, very big component of you know, visibility. And so we, our system does those site audits and recommends changes to make based on all that.

Kosta: So um, correct me if I'm wrong but like how, how can AI like visibility be optimized? Again, correct me if I'm wrong but if, if aren't LLMs in most cases kind of like black boxes, like they don't it's not transparent on how they rank and you know, what they actually do. As opposed to like Google, where it is open and you could kind of reverse engineer that.

Jon Mest: So, I mean, at the beginning of SEO, it was the same idea. So, like, nobody really knew how Google search engine worked. But over time, people kind of figured it out and reverse engineered it. And then this whole industry of SEO started. So right now, I mean, that is, I mean, that's the secret sauce of what we do. So, Joe, my cto, what we did from early days is try to figure out and try to reverse Engineer how these LLMs make decisions. And so what we're learning was very interesting. And there is like concepts of, you know, like there's entities and they want to understand like the scores between entities, how closely like map to you to other things. Like there's. They do have the idea of authority scores on your websites. They're all things that are actually like being used by LLMs to make decisions. Now what we do is because again, nobody gives you the answer. Um, just like nobody gave, like nobody gives the answer to Google search algorithm. Like, you still have to figure that out. Well, nobody gave us the answer. So we kind of, like I said, reverse engineered that. And by doing so, we realized there are certain things you can like kind of look at. And um, the main way to do that. I'll, uh, sorry.

Kosta: Stupid. Oh, good.

Jon Mest: The way, the main way to do that is to actually go in and like, see what is like the LLM saying that they did last week or like, uh, like week before. The week before and actually track and identify what they're recommending and how and why and that, and then taking that information and using that to kind of be able to go forward, plan, try it, and if it works, then keep leaning into that. So that's, I think, the very like, simplest version of that. But I mean, the main idea being that if you are a brand that you want to be ranking for, you know, best grade T shirts online, um, that are soft and whatever, like, we'll see. Okay, how do they recommend that today? We'll run those samples over and over and over again in the m different models who they're recommending and they'll actually tell you why. They'll give you the citations and the sources to what they're using. So maybe that's a bunch of list articles on GQ and Vogue's website. But, you know, like, if you're looking for, you know, why should I care about this material? That's more informational content from your blog or whatever that might be. We'll see on a prompt by prompt basis what you need to be doing and recommending brands to do based on what the LLMs are kind of already using to basically to recommend brands. And so we do take the existing data to then make a recommendation, inform recommendation of going forward.

Kosta: Got it. How long did that, uh, process and research take for your partner to kind of gather these insights and data and actually come up with something that's real and tangible?

Jon Mest: I mean, it's still ongoing, but yeah, I mean, that was the core of what we were doing at first. So that probably the first initial take was probably like a few months of just like, figuring that out and trying to understand how these models work. And then, yeah, we're constantly tuning it because these models are changing too. And, um, every time they make an update, we have to be on top of that so that we can learn that. And we see that by just like, looking at the data every single day. Um, so that's why our customers love us, is because they're running their businesses like they're selling T shirts online. They don't want to be thinking about, oh, OpenAI tuned their model to, like, really favor Reddit content more. Now it's like, okay, we're like, cool. Like, our, our recommendation system will pick up on that and recommend that to the brand. But they don't have to, like, they don't have to think about that. That's what we do. And we kind of monitor for them. But again, because it's because we're parsing and cite every one of these citations and figuring out, like, what it is that's actually driving this and why are they recommending brands? And with enough data, which we've gathered over the last couple years, you can kind of see this and then feel, I mean, pretty confident because, again, like, our customers take our advice, use our Playbooks, implement it, and it works. And so they keep doing it week after week. If it's working, then, like, yeah, that seems to be going the right direction.

Kosta: Yeah. So does chat ranks, like, just offer suggestions on, like, which, um, questions and phrases to optimize for. Are you also providing the content as well, or it's a full suite?

Jon Mest: Yes. So the first thing it does is it audits your brand. It says, okay, like, here are places you're missing, here's where, like, you're getting smoked by the competition. Um, but these are core areas we really think you should focus on. These are because we will do, like, a translation of Your brand, from like what you are as a brand to what you should care about in AI search, that translation layer is like non trivial. That takes a while and it's like actually is a very core part of what we do. And then once you have that, okay, great, like where are your best opportunities? So this, this one prompt over here is really high volume. People are definitely searching it a lot. It's a really big area that you could go after and none of your competitors are really like focusing on it, but you aren't either. Like go after this pretty hard with really specific content and really specific things on these like things. Or you know, go out and record a YouTube video about this topic and I bet you'll go win it. Like that is like we're trying to find these opportunities for our brands and then we'll also write the content, record the video, do all that kind of stuff for them. And so it really is a full suite solution. It is like a identify the problem, build a data layer that supports an answer, and then the recommendations engine recommends stuff. It'll actually create the content. I mean we're dubbing it one hour per week marketing because it really is like if you want to just go in for one hour a week and just give it the insights that you have as a business, we'll do the rest. And that's the part where we differ with some of our competitors right now who might be saying, oh, it's a fully agentic system. Just like press a button and it goes every day. Like we could turn that on too. Like we, we could just press a button and turn that on. We choose not to because it doesn't work right now. What you need is real human insight. And so we'll say, hey, here's a blog post we recommend you write. Here's the, here's the first draft of it. But we need this user testimonial, need this data point. We need like this information from you that only you know that'll help inform the AI that you are the leader in the space. You know this really well and here's why. And you fill in those details, we'll do the rest. Like the content being AI written doesn't really matter anymore. Like you, there is like some nuance to that. We want to make sure that you have the right style and tone and things that you care about. But the reality is like the AI, like they care about new novel information. If you can give that to them and you can kind of explain why you're different, that's what really matters. And so our m. Human in the loop is required. But, but we try to keep it as simple as possible. So it's really, we call it, like I said like one hour a week marketing. You follow our advice and you'll get, you'll get results.

Kosta: Yeah. Nice. So it's great. I love how you, you're eating your own dog food with uh, chat rank. What are the actual results? Like has AI, like organic AI results? Is it surpassing Google? Um, what trends are you seeing on your end?

Jon Mest: Yeah, so Google search still dominates general search, but what people don't realize, or people maybe do realize now is that about half of Google search results come back with an AI overview, which is Gemini powering that. Um, and so for example those AI overviews, um, depending on the source you use for this, it's anywhere from like 50 to some people say claim even 90% of the answers in the overviews do not come from page one links. Meaning it's not like just what's on page one that matters anymore. The AI overview, which is right at the top there, which is basically giving you the answer, is not necessarily going to be a page one link. It's actually more likely to not be. And so for you as a brand, just knowing what you do really well and like, even if you are like your website would be on page seven of Google, like if you have the best content information for a topic, you'll win in that, that prompt. And that again people don't realize they're prompting AI. They're just going to Google and searching, which still owns whatever, 97%, 96% of search, but they're getting those Google AI overviews. So Google's get be like basically feeding you or any real user all this AI information right now ChatGPT has a couple percent of the market now and like again like the other players like Claude and Perplexity have some. But the reality is that Google still dominates the market, but Google is subtly and not so subtly feeding you AI answers. And so it really matters to everybody.

Kosta: Yeah. Uh, so is ChatGPT still dominating like uh, outside of Google in terms of the other AIs?

Jon Mest: Yeah, they're definitely, they're leading by far as far as like people actually using the tool for just everyday users. They have a lot of free users, which is going to be hard for them as a company to eventually convert those to paid. Um, but yeah, they have a ton of traffic through.

Kosta: And do you see that personally, um, sustaining with ChatGPT?

Jon Mest: I do. Um, I think that there's they've at least gathered enough of their users to like people just use it. Like there's a lot of people just not going to change your behavior. And they do give you a pretty robust um, amount of information on a free plans which is great. I mean they're going to start introducing ads on those free plans. So that's like they have to get paid somehow and they're going to go that route, which is, I mean, fine by us. You, you can't buy the answer as a brand. You can only like put an ad next to the answer. Which makes me feel much better about like this all because they're not just letting you like, you know, buy an answer in ChatGPT. But um, yeah, so I mean I think that, that, that will hold for them now. I mean a million things can change between now and like whenever this podcast launches in a couple of days. It doesn't really like so much is changing but the reality is like these people, like people are using these tools more and more and as more, you know, not just tech savvy young people are using them, but actually like, you know, everybody's using these tools and it's going to lend more itself, more to just this is how brands get discovered. So that's like people are doing the research on these tools before they ever step walk in your door. And knowing that is really important.

Kosta: Yeah, it is. I find that like definitely ChatGPT, it's, you know, it has a network effect. They were the first. Everyone's on it and like, you know, with these AIs like once it starts to know you a bit better, like it's just, you know, it's hard to move. Um, I've personally noticed a lot of like Claude and even like Grok, even Gemini Grok like outperform chatgpt in certain respects. Like I found myself uh, using more than just chatgpt recently. Um, I don't know if you feel the same, like what's your kind of workflow? Like what are your go to tools?

Jon Mest: Yeah, so we as a company have a policy where we are all supposed to change our primary tool week to week. So right now, this week I'm on Claude. So I'm going to be using Claude this week. Next week I'll use Gemini the week. I value Chat. So we like, we'll use all the different tools because I do have favorites and I kind of think that some of them do better at certain things. We definitely are forcing our team to use all the different models on purpose because we Want you to understand the nuances and learn the differences between the different models. And so we do that as a practice. It's very intentional. And so that way we kind of force ourselves to use a tool even if we don't find it to be our favorite tool. Because that way we have to like, learn why it's different and what it's doing. So for example, like Google and Gemini are much better at doing like localized results probably because of like Google Maps and the local SEO. All the things that they people already optimized for in Google. They're just very good at like those kinds of things. I find Google to be really not great at like creating documents for me, Whereas I find ChatGPT to be excellently like building sales proposals like organizing call notes or things like synthesizing stuff like that. We, we do that and I find Claude to be generally the best writing tool. Um, but we have our nuances and so I definitely use them all. We use all these different tools all the time. Um, and we definitely, I find there are different ones that do certain types of tasks better. As a company. We actually use all of them on purpose because we need to know our customers to know why these are different and what you should be optimizing.

Kosta: That's really smart. I've actually never heard that before. Um, like using purposely like you know, every week a new, the new, A new tool.

Jon Mest: And they do change so often. Like you have to, you know, like move around. So you mentioned like how Gemini might out like function like ChatGPT. So yeah, actually like Gemini3, like uh, was much. Was a better performing model than OpenAI's model. And they. OpenAI released two more models but they still hadn't surpassed Gemini's last version. So like there are like changes in that way. But at the end, like I said, like, I find like Gemini to be terrible at like you know, writing sales proposals, But I find ChatGPT to be excellent at it. Like some, like, some tasks just like, I don't know, I can't get it to like even somebody that prompts AI every day, like knows pretty well how to like prompt things. They still can't get it to like do the things I want it to do. So I, it really just depends. But I'd say that I probably like lean more into Gemini as a, as a tool just because of the Google suite and how it integrates with everything. Um, but that's just probably personal preference. I don't find that to be, you know, in like a.

Kosta: The answer that's that's smart. Uh, I actually think I'm gonna steal your playbook and start doing that in my company too. Um, I, I'd imagine like you running two companies, um, you know, splitting your focus. Where are you at with a lot of these agents and like Claude Bot coming out? Like, you know, are you, are you utilizing any of these tools to optimize your day and be, just be more efficient?

Jon Mest: We try. So I, I, I'm like a weird person. Like I, I, I run and operate like two AI companies, but I still keep like all my like notes on pen and paper. Like, like all my, like I have a little notebook of like my m. Every day.

Kosta: I have like a cue card.

Jon Mest: Yeah, I'm literally just like a piece of scrap paper and pen. Like my to do list still remains on my piece of paper, which drives my team nuts because they're like, what do you, like, they just want like, they give me every different like efficient like tool to use and I'll be like, no, I like my of piece and paper because it keeps me like focused. Um, I know before I go to bed that night, before I close my laptop, these things have to be crossed out and that just makes me feel good. Um, we're using a lot of these tools for like, like personal, like type things. So what we use, I mean for scheduling, we use a tool for um, there's just no reason for you to ever email me and like I have to go back and forth you seven times. I'll schedule a meeting. So like, yeah, there's a Cal, we use Cal.com, but I also um, use a company called Skedge, um, free shout out, I guess. Like they're, they're, they're customer of ours, but they're, they're great. They just like, it's just an AI like assistant. You just install in Gmail and it just like schedule stuff for you. Like that stuff saves us a ton of time. Um, we use like a lot of tools like that make it simpler. I don't have like an agent, like a co pilot, like, sorry, like a cowork, like running on my computer right now. Mainly because I'm so busy I don't have time to like train it to like not f up. So like, I kind of just like, like right now I've not been doing it, but it is like something where it's, it's been on my side radar for a while to just like buy a Mac Mini and just like go do it. Like just go like build my own agent. But I've not, I've gone there yet, mostly for time reasons. Um, with two companies and two young kids, just, it's, it's tough.

Kosta: I'm on the same page, man. Um, I'm, I'm going to tell you something very, uh, transparently here. So you know, you're a guest on this podcast. Um, obviously I do my research and like, you know, check out what you're doing. Which, which I did, but on the side, like, I did that already. I'm like, you know what you're talking about, like Claude Cowork and all this stuff. And like, I've always like, you know, I wanted to try it and like, you know, get it going and just find some use cases. So what I, what I did was um, uh, I gave it a task, connected it to my browser and say, hey, I'm interviewing John, uh, mast. Here's his LinkedIn profile. Do your research. Search like other podcasts he's been on. Uh, give me some, you know, questions, some topics and like, put it all in a Google Doc. And it did it in like five minutes. And like I, I was actually shocked at like how good and like accurate it was comparing it to like my research that I did. So I found that as like, uh, all right, maybe there's something here in

Jon Mest: terms of a use case that's not bad at all. I kind of like, I mean, so I know this is like, to be true. Like I, I, we all should be doing more of this. And so it's funny. Like my, my Joe, my, my cto, he's all day, every day, like, like running like multiple agents in Claude code, like building stuff. He's like, we are like running a, uh, full engineering team with a very lean team frankly, because like, we just, it enabled us to do these things that we were, we are very AI savvy as a group. But it's funny, like, we are not as savvy at like the actual things that like call the, the average person is probably doing more of than I am today. So this is like, it's a, it's a wake up moment to like be like, okay, well maybe I should give up my pen and paper. But I will say one thing that we do as a business that's really valuable is we do record all of our sales calls with Gemini. So, um, we just do. We use Google Meets and Gemini records and transcribes the calls. Now. Um, it's all transparent. It says that you're being recorded when we do it. But um, anyway, so it's basically. We basically built our own Gong. Like, I mean, I basically went to go buy Gong and Gong was so expensive that I just. We just rebuilt it internally with, like, recording calls and then of Notebook LM through Gemini, just built like, we have frequently asked questions what we're looking at, like, what's. What's resonating well in demos, what's not. It's like, basically everything but, like, tracking my sales team and like, that does everything Gong does. And we just built it ourselves and that was. It took us, I don't know, not very long to do that. That is a really valuable tool that we use now every time we go to do, like, a new demo or

Kosta: like you say Dong.

Jon Mest: Gong.

Kosta: Gong.

Jon Mest: Yeah, sorry. G O, N G. They're like the sales. They've been around forever. Um, they're like the sales analytics company. They would, like, track your sales calls. Everything else. Yeah, they integrated AI now in the last few years to make it so it's very, um. Say, uh, like, more like doing what I just described originally was like, you know, keeping track of your sales team. Are they making. They'd be dialing enough times. Are they, like, closing deals? Like, all that kind of stuff.

Kosta: Yeah.

Jon Mest: But now you can actually. You can query against your sales transcripts and see, like, what's going on and what's happening, who's not. Oh, this person didn't, like, sell very well. Like, why, what's going on? Is the demo bad? Are people not reacting well? Like, all that kind of stuff.

Kosta: This is Gong IO?

Jon Mest: Um, yes.

Kosta: Is that the right one?

Jon Mest: So it's, um. Yeah. Gong IO.

Kosta: Gong IO. Cool. I know. I don't know. Yeah, I'm actually surprised I haven't heard about this.

Jon Mest: All right. They've been around for, um. Yeah, 2015, it looks like. Yeah, they've been around for a while now.

Kosta: Yeah. So you use this to. It, um, transcribes the sales calls and provides, like, insight.

Jon Mest: Yeah, you can not just get insight, you can actually learn. Like, I think it'll do facial recognition now. So if it's a video call to, like, look and see. See, like, were they paying attention? Are they interested?

Kosta: Like, all that.

Jon Mest: We don't do that. We just take the transcribes transcript scripts now. But basically we just do. Essentially what that does is we take all of our sales calls, feed them into a notebook. Lm, um, notebook. And. And then just use it. We can say. You can just ask questions of the data, figure out what's going on. If I have to do follow up Emails or like, kind of if you have to get tasks, like, okay, who do I need to follow up with? This week it's been, who, who's it? Like, who have I talked to in the last month that has not responded to my email recently? Like, what should I do? It can do those things and flow into workflows, like through hubsp.

Kosta: Okay.

Jon Mest: It's like actually like a. You can build these, you know, these. Call it like, little hacky ways to kind of. Without having to spend a lot of money on the sales tool. You can kind of remake them, um, easily with, like, the existing tools we have. And so we've leaned into that a little bit more. Again, bootstrapping. We just don't have, like, you know, 10 grand to spend on a software to do that. So we just won't do it like ourselves. And so that's like, another way we've done that.

Kosta: Yeah, makes sense. Can you not do that through, like, just, uh, Gemini, how it takes the notes and put that into Notebook LLM?

Jon Mest: Yep, you can. So that's what. That's essentially what we do. So we just. We take our call notes that save into a Google Drive, and then we just feed that drive into like, a Notebook LLM and then query against it. It's like a. I'm just trying to

Kosta: think like, like, where does gong come in into that stack? Like, what. What do they do that?

Jon Mest: So I haven't used the tool in a long time. At my last company, we had it. So I don't know. But they, they, they're like. Right now, I was listening to a podcast from, um, the Chief Revenue Officer, Vercel, um, and she was basically talking about how they're using. I mean, I think she, they must be a partner of the gung, I guess, because she talked about a lot. But they were like, um, talking about how it is like, feeding their content engineers and feeding their, their teams. Like, they now know what to do based on the feedback they're getting from their sales calls. It's kind of like automated too. They can kind of just query against that data and know what's working, what's not, how to, like, build better things for their teams based on what they're seeing in the call transcripts. And again, they have, like, way more sales reps doing way more calls. It's probably, like, more efficient to do it that way. When your team's that big for us and our team, we just kind of just, um, share a Google Drive.

Kosta: Yeah. Yeah, makes sense. Now, what about, like, you do these Podcasts, right? Like, what made you decide to get into, you know, podcasts as a channel? And how's it. How's it doing?

Jon Mest: Um, one great. Um, so it does really well for us, and I'll explain why. So from Just Reach out, we learned really quickly that these are great ways to, like, even just build. The traditional backlink for your, like, website is like, you go do a podcast and then somebody, they'll record the show with you, they'll post it, then they'll post your company in the show notes, and all of a sudden you're getting, you know, eight backlinks from iTunes and Spotify and YouTube everywhere else. That was, like, the original pitch for why we added podcast to just Reach out, like, years ago, um, as a channel to reach out to, because it is, like a new way to get your information out there. What we realized also is that I am not going out and trying to, like, pitch to massive podcasts. Um, or we don't really tell our clients do that either. Unless you have a massive brand reason being like, the podcasts are a weird thing where, like, people just listen to what they like and what they listen to. And so if you are really into, you know, founders and, like, how founders are doing things well and, like, how they're, like, they're treating their businesses, and you just really are intentional about that. You're going to listen to founder views and you're going to, like, really care about this podcast, and you're going to, like, you're not going to spend like an hour or two a week listening to shows if you're like, if you don't really care about it. And so we always tell people, if the podcast has 30 listeners on average per episode, those 30 people are your exact core ICP, who you want to, like, get your message to go do that show. There's no reason to, like, make them have 10,000 listeners. Like, sure, more visibility is better, but actually, if there's no engagement from those 10,000 listeners, it's just like, shoot the shit, have some fun, like, puff stuff. Like, who cares? That's not really relevant. And so we learned that pretty quickly. And so for us, we're really intentional about kind of the shows. We reach out to what we're going after because we want them to be those areas. So, for example, I did a show. It's, uh, called Med Spa Marketing. It's like, it's all about marketing. It's a marketing agency for med spas all, um, around the country. Like, we saw that Med spas were A great chat rank customer. And so I reached out to them. They're a great team. They're based in Nashville and they, I had a great time doing the show and very, very simple, easy like ways for med spot owners to use AI search to their advantage. Like very like not salesy at all about chat writing, just kind of talking about stuff. And we've had the inbounds from that because MedSpa is like, oh, I need to do this. Like, it's great. And so we, we really lean into that channel a lot. So that's like the actual practical reason why we do it. But the side of that also is that in addition to now getting that traditional um, SEO backlink that you would get from the shows, you're also YouTube now transcribes all videos automatically. And so YouTube is a huge citation into why AI gives you answers for you. And so I always like to explain this to people because we've had a bunch of customers be really successful with it. But you like first of all, Google and Gemini, those answers almost exclude always have a YouTube video attached to it. The answer again, they own YouTube, so that makes sense. But they're always going to add a video in there. So if you are recording a video or you're doing a podcast and you are very intentional about like your talking points to that podcast or what you're saying or why you're saying it, that'll get pulled out of the transcript and used and fed into those answers. So we've had customers that like have done this and had like done podcast episodes or so 20 minute conversation and then don't get that podcast. We'll see in the chat room that podcast interview will get cited as the reason why their brand is winning in that topic area that, that prompt. And so that is very like easy to do. And it's like uh, I shouldn't say it's easy to do. It's very like doable. And so we've done that with like B2B SAS companies, we've done it with medical professionals. They'll go on podcasts and just like talk about procedures and then when those procedures come up, they'll be listen like listed as that answer. And so Google really is good at understanding like who is actually giving you the best answers in their interviews, not just who has the best video.

Kosta: Smart. Yeah, that's um, that makes a lot of sense.

Jon Mest: The example I give people is like a very real example is like I have, I have a couple young kids, like installing car seats in my car is the bane of my existence. It just immediately, immediately I go to YouTube, like, how do I do this? And if I search like a, a car seat in the YouTube video, I almost never get the, the manufacturer's instructional video. I'll get some like mom in California explaining how to do it. Always a better video than M. Like they actually, than the manufacturer's video. And I'm like, thank you Google. Like you knew this was a better video. I watch it within 30 seconds, I'm good. It's just like those are like, they know that they get that. So it doesn't matter if that mom has like a thousand followers and the manufacturer has like a million followers. They're just going to give you the mom video because it actually is a better video.

Kosta: To answer your question, I'm laughing because I have three kids, uh, myself and ah, the amount of times I've done

Jon Mest: that, I have many degrees and I still can't install cars really hard. It doesn't do anything.

Kosta: And you obviously use just reach out to connect with podcast hosts, right? That's a big use case.

Jon Mest: Exactly. So we eat our dog food there, we do it ourselves and so we go. So I mean that's how, I mean that's how I found you guys. But then once we do it again, we don't let you spam and just reach out. You can't just send a million emails or like automate emails. It requires you to go in and manually figure out is this a good podcast for me? You can create some messaging. Like, you can think about it. You like, you review it, you edit it. You like, you build stuff like you're telling it about you. It helps AI help you. But you can't just like click a button, have AI spam people. We actually don't allow it. Um, we don't allow you to do it. So we actually lose customers because they're coming to us looking for spam and we just don't, we just turn them away. Um, yes, we do reach out to, we use just reach out to reach out to podcasters and media as well.

Kosta: Do you find it difficult to attribute, uh, sales to your podcast?

Jon Mest: So we ask um, all of our customers in our intake forms as well as when we get on the calls with them, how they found us and when they sign up as well. So we ask like so many different times. And so yes, it's self reported data so it's like not always perfect. Um, but we do try to do that as best we can from a, like, at least at that level. So I always recommend anybody like if you're going to add this as a channel, like for example podcast or like, you know, AI search, just have. How did you hear about us? Just add like AI tool or chatgpt or something your list there to make sure you get that level of information. In addition to that also just like you can also do a lot of tracking. So we do track a lot of this stuff through those. You can do UTM linking and tracking through that. And so for chat rank, at least we can tell you, hey, you posted this blog post. Now we can we, we link to your GA4 data or your like search console data will tell you they found this page through this channel, signed up and then like paid you. Like you can see all that through your to show you that you're actually growing your sales. And that's like for E commerce it's easier like a Shopify store. It's super easy to just like show that flow all the way through. When it's like a B2B or SaaS company, it's like a little harder. You have to like, you know, connect to a CRM or like at least like talk to them or figure that out with them. But ultimately it's like, it's pretty easy. And we, we know every single one of our customers we've ever had on ChatRank. Like going D back to day one, until now, we've never had a customer for those not be true traffic coming from these AI channels like ChatGPT, Gemini or others convert at higher rates than average traffic.

Kosta: For sure.

Jon Mest: It's just like, it's because like they're intentional. They're doing the research in AI. If they land in your site, it's very intentional. They're like, okay, I did my homework. Maybe I narrowed it down to three like vendors I'm looking at or maybe I just narrowed it down to one I'm going to buy. Like, but they're coming to your site ready to buy. Having done the research, that user is so much more valuable than just called your average traffic. And so that is where like we really lean into like just knowing that who that user is and catering to that person is really important.

Kosta: That's a good point. And I honestly don't even think it's um, always just because they've done the research. I just think if you think about it, it's very psychological. I find people trust these AIs way more. Like if you're just like doing something in AI, it gives a recommendation. For whatever reason, people just trust that information and just go with it. I'll give you the med, which I find very interesting.

Jon Mest: I'll give you the med spa example. Again, the reason why this has been so powerful is because for a lot of people that are going to a med spot, it's a lot of times their first time. This is why they're doing their research or they're thinking about it. They know when they walk in the door of a med spot, they're going to be sold to like, they're, they're going, oh, you need this. I know nothing. This, Botox, this thing. Like, they're going to like, try to sell you on different things you need. Uh, but reality is you don't. Like, maybe you do want to be sold too, but you probably want to do a little homework before you go in there. So you can go to an impartial third party AI tool and just like, have a conversation, like, what should I ask for? What should I look out for? What are like my opportunities here? Like, and just having that conversation ahead of time. And then when you go, okay, well, I want a med spa that like, has good customer satisfaction, will not try to oversell me, and has this. And like, they try to answer those questions. If you're med spa, if you have good reviews, if you have like, good human sentiment, talking about those qualities of your business, you're going to show up first, that user is going to click on your page, go, walk in your door and actually, like, be ready to go. It's a great use case and example of like, they want to do their homework up front and so they don't, like, so they can have an impartial third party tell them all this stuff, but they still want to go do it, they want to go buy. And so you as a brand need to make sure that your brand is aligned to what they care about. So like, yeah, like in medical, it's like, okay. Like, we realized for one of our customers, it was like they really, people were asking a lot about Saturday hours. They just have to like, write on their, make it more clear on their page that they have Saturday hours. Great. All of a sudden they're getting more people showing up at the door. It's like, it's like something's as simple as that. Just figuring that out is really important for a brand to understand.

Kosta: Yeah. Yeah, for sure. Um, last question I have for you is, uh, why you're currently in San Francisco, right?

Jon Mest: Uh, actually, no. So I'm, um, in St. Pete, Florida. So I personally am in St. Pete Florida. The company's also in New York, so I'm back and forth in New York a lot. Um, that's where we were. Uh, um, my partners still are, but.

Kosta: Yeah, I don't know where I saw that. It feels like your LinkedIn or maybe I misread or my mistake, you coordinated up.

Jon Mest: I don't know. All right, Never lived in sf. All the tech I've done, I've never actually, I've spent.

Kosta: All right then, my mistake. But what I was going to ask regardless is why did you decide to go the bootstrap route as opposed to, you know, get around or get funding and investment?

Jon Mest: Yeah. Um, so I'll give you the short, punchy answer. And obviously, like, maybe if I have, if I have, uh, a soapbox for a second, I'll give you the longer answer. But like, the reality is I work for both bootstrap companies and venture back companies and I find the bootstrap mentality much more my style. It is like I said, like, you have to sell a customer today to exist tomorrow. That grind, that like, that mentality of just like, you can't just coast. You have to be always thoughtful, intentional about your time, your customers, you have to keep them successful. Because if you sell a customer and they churn like you're starting from ground zero again, you got to build that one up again to grow again. So not. You can't just grow like, you have to rehire that new customer and then grow like that just, it's like so much harder. And so if you don't have that fallback option of like venture capital, you're burning every month, it makes that intensity and that, that like, pressure, I guess, a little bit higher. For me personally, I. That's why I thrive better in that environment than I do on others. My. That's like the, the real answer, the longer answer is also that the VC model is kind of broken right now. Um, it has never been cheaper to build software at least. So again, if you're building drones or like hardware, like, sure, like, I, I get it, you need to go raise venture. That's like, I can't. You need money and capital to go do that. And so I have a lot of people here in my incubator working that like, are out raising capital because they're, they're literally building, they're trying to like, blast rockets off from the, like the Gulf of Mexico. Like, they're just like, they're trying to like, you know, actually like, do crazy things that like, require a lot of capital. Great. But at the same time, like we always tell people like uh, people that come to me for advice, they say like what should I do? Like should I go raise venture? And I'm like well what do you need the money for? Like, do you have any customers yet? Have you tried this out? Have you like talked to customers? Go see if you can sell a customer, get somebody to put a credit card down and get a stripe account, just like pay for it. Like uh, pay for your stuff. Okay, great, you got a customer. Can you get 10? If you can get 10, I bet you don't need to raise capital because it has never been cheaper to like write soft build software. Like go do the things you need, build a website, like go build marketing materials, like actually go get like a, like a calendar account. It's really not that expensive. There's some cost involved. Yeah, it's not like free. But it's never been cheaper to start a company. And so for me, unless you're building like some foundational model company or you're building some hardware thing, I just don't find it that the model really works to go raise a lot of money. And listen, I might sound like an idiot here because a lot of our competitors to Chat Rank have raised massive amounts of money. Um, like massive mass amounts of money or like profound is one of our biggest competitors. They've raised at a billion dollar valuation. Last week they just raised their now unicorn 18 months after starting. I don't know what they're using that money for. Like we are like I talk to my CTO all the time, like hey, if I give you a million bucks, what would you do with it? He goes, I don't know, like you make me be pretty cheap on DevOps tools. That's about it. Like everything else. Like I would just, I don't know, we don't need much more money. Like we're, we're profitable growing at our current state. Like why would we go raise a bunch of money? So I don't. Especially when the industry is so young and nobody really knows where this is going to go. And so anyway, that's my long winded way of saying like I think right now ventures and you can see how the way they're, they're investing, it's hard. It's really, really a weird model right now. And so unless you're going to build a multi billion dollar M company, the venture model might just not work for you. Like they're just not, it's not going to be like super effective and like it Might be harder to find other capital.

Kosta: So.

Jon Mest: I love the bootstrap method. My, my business partners and I, we've all bootstrapped our own businesses before and we much prefer it. So that's, that's the path we've taken.

Kosta: Yeah, I'm on the same page. I, I agree. Um, on the flip side, though, like, you know, I think there's time and place for, you know, it's not like I'm like, totally against getting capital or funding. There's definitely a time and place for it. One of the advantages I can see compared to, like, if you're comparing a funded company to a bootstrap company, you just have more capital to deploy and test things quicker. Right. As opposed to, uh, if you're bootstrapped, you have to be very thoughtful and mindful on like, every test, every dollar that goes out and just things are slower.

Jon Mest: Yeah. Uh, our road map, our roadmap is basically paid for by new customers. If somebody wants a new feature, we go, great. If it's on our roadmap, we're in, like, we'll go do it. That's like our, our philosophy on that. Yeah, I agree. It. It is. That is true. If we get to a point where, like, I think the market's a little more mature and there's a chance where, like, growth equity would help us, like, you know, grab more of that market. I'm always open. Like, I'm, I'm not like, anti. I just think that right now when you're, especially when you're getting started and especially like in 2026 when it's like, never been cheaper to like, go build software. I just find whenever somebody comes to me and asks me, I just tell them, like, go try it. Like, go see if you can sell 10 customers first before you go for a venture.

Kosta: That's the thing too. Nowadays, like, we're living in a time where just things are moving so fast. I mean, a lot of people get stuck with like, analysis paralysis and, you know, overthink things. Now's not the time to overthink. Like, you could wake up tomorrow and that thing you are thinking about is totally obsolete.

Jon Mest: Yeah.

Kosta: You just gotta get up off your, you know what and just do the thing.

Jon Mest: Yeah.

Kosta: You can't right now.

Jon Mest: Totally.

Kosta: Yeah. Um, Anything else, John? Anything we didn't cover that you want to mention? Touch on?

Jon Mest: No. This is a great conversation. I really enjoyed it. Um, I think just in general, like, what. We kind of just summarize what we talked about, but this space of AI visibility is changing so rapidly. And what we like to do as a brand is we just like to be at least a thoughtful educator to somebody that might have questions. So if anybody's listening to this and they're thinking, like, I just don't know the space well enough to, like, make a decision about a tool, call us. Like, I might say, hey, depending on what you need, like, you probably just need the $29 version of this. Like, go talk to these guys. I think they're pretty good. Like, I don't mind recommending a competitor of another brand if I really think that's what's, like, helpful for you. I'd rather you learn that and know that. That way, when your business is, you know, big enough to need us like you, you come. You trust us, you come call us. Like, I really, like, will happy to happily do that. So my only my push is if anybody's thinking about this space in general, how do I, like, get my brand, like, ready for AI visibility? How do I think about this in general? How do I fight through the noise of what people are shouting on LinkedIn? Like, just anything like that? Please reach out to us. Um, you can either go to our website, ChatRank AI, or I'm just Jon Jon, ChatRank AI, shoot me a note. I'm happy to talk through that stuff. Like I said, no company is too small. We want as many opportunities to have conversations with customers as possible. So whether you think you're a customer now or later, don't hesitate. Please reach out.

Kosta: Amazing. I will put that all in the notes as well. And this was great. I really appreciate it. John. Um, thank you so much for taking the time. This was very insightful for myself and I'm sure anyone else, uh, who's listening, so I appreciate it.

Jon Mest: Thanks, Costa. I really enjoyed it.

Kosta: Soon.

Jon Mest: Sounds good.

Kosta: All right.

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