---
title: "How HubSpot Built a Media Empire"
episode: 93
podcast: "The LeanScale Podcast"
publisher: "LeanScale"
guest: "Jonathan Hunt"
guest_title: "Head of Owned Media"
date_published: 2026-07-15
date_modified: 2026-07-22
duration: 00:46:59
word_count: 8533
topics: ["demand-generation", "brand-positioning", "gtm-strategy", "mergers-acquisitions", "ai-in-gtm"]
canonical_url: https://leanscale-knowledge-hub.netlify.app/podcast/jonathan-hunt-hubspot-media-empire/
source: "LeanScale Podcast Knowledge Hub — https://leanscale-knowledge-hub.netlify.app"
license: "Free to quote and cite with attribution to The LeanScale Podcast."
---

# How HubSpot Built a Media Empire — Full Transcript

> Episode 93 of The LeanScale Podcast, with Jonathan Hunt.
> Published July 15, 2026 · 00:46:59 · 8,533 words.
> Machine-transcribed and **not diarized** — speaker attribution is inferred, so verify
> attribution against the audio before quoting a specific person.
> Structured breakdown: https://leanscale-knowledge-hub.netlify.app/podcast/jonathan-hunt-hubspot-media-empire/

## 00:00 — Cold open + intro

**[0:00]** (logo whooshing) - Joining me today is Jonathan Hunt, who leads owned media at HubSpot, where over the last three and a half years, he has quietly built one of the most ambitious in-house media operations in B2B software. 17 YouTube channels, six newsletters, and more than a thousand short form clips going out across Instagram, LinkedIn, and TikTok every single month. Long before ChatGPT cracked open the distribution conversation, Jonathan saw paid in search getting more expensive and less reliable, and HubSpot made a contrarian bet that the right answer was not to pour more money into rented channels, but to build an audience that compounds.

**[0:44]** To staff the operation, he did not poach from other software companies. He went straight to Business Insider, Morning Brew, and the rest of the editorial world and hired their journalists. The result is a machine that outperforms traditional marketing on cost per qualified lead, generates equivalent media value HubSpot would otherwise have to pay for on Meta and Google, and has reframed how the company thinks about top of funnel entirely. In this conversation, Jonathan walks us through the thesis, the architecture, the talent strategy, and the three bucket framework he uses to defend owned media internally, and why he thinks every B2B software leader

**[1:23]** needs to start building this muscle now. Jonathan, you started building this three and a half years ago well before ChatGPT was on anyone's radar or AI, LLMs in general. What did you see in the market that convinced you the paid plus search era was already ending? - Yeah, well, first of all, thanks for having me. What we saw was just complete disruption. The top of the funnel looked nothing like it did even five years ago. And a lot of that was precipitated by the advent of ChatGPT and so what you were seeing is discovery happening in more places than where you would traditionally find it. So those 10 blue links that you would get

**[2:01]** on a search results page while they were still important were being turned into AI overviews. People were going to ChatGPT, paid media costs were soaring, and people were just discovering brands and content in more places than ever before. And that trend had been happening for a while, but I think it really came into focus over the last, I would say, three, four, five years. And so, you know, content, especially at B2B companies, no longer could be a nice to have, it really became a must have. And I think as software companies, and just B2C companies in general, started getting better at measuring the effectiveness of content, that became very clear

## 02:06 — What HubSpot saw before ChatGPT

**[2:40]** that there was opportunity, not just at the very top of the funnel, but closer down to the bottom of the funnel for content to be able to drive real business impact for brands, both from a brand awareness perspective, but also from a customer acquisition perspective. - Yeah, and I'd say over here at Lean Scale, we have a similar thesis. We invest really heavily in content. We have the podcast, we have educational content. We're posting continuously on YouTube and LinkedIn. I had the luxury of being the founder CEO and just having the intuition and, you know, gut to make the investment. At a company like HubSpot, how are you setting up the infrastructure

**[3:19]** to make the economic case to the CFO, to the exact team? What are you doing to convince that this is the right investment? - Yeah, well, I think first of all is reframing content. And I think content, just historically, like let's be honest, has been a little bit more difficult to measure and attribute down funnel business impact to. Like with direct response, it's a dollar in, X dollar is out. Everything is pixeled all the way to last touch. And it's just a very clear, predictable way of doing marketing, but at the same time as costs go up and the question around does that actually drive brand value continues to be a question that's being asked.

## 03:25 — Making the economic case (and the measurement problem)

**[3:59]** The opportunity for content being positioned as a growth lover has become, you know, a bigger one than I've ever seen in my own career. And so we don't look at it as something that's tracked through vanity metrics. We don't look at it as something that is a campaign. You look at it, that's something that can disproportionately drive long-term growth and business impact for HubSpot. And so what that means is really creating something that can be sustainable, drive lower cost per acquisition long-term as the result of that investment. And something that has, you know, from our own perspective, been able to drive a significant amount of new leads for HubSpot,

**[4:36]** but at the same time, expose HubSpot to audiences across the channels in the formats that they're oftentimes expecting brands like HubSpot to show in. So short form video podcast through, you know, our bench of 150 creators we partner with on a monthly basis through newsletters, through websites, through LLMs as well. And so that's how we look at it holistically and how we make it make sense. And the good thing is that, you know, as measurement has become a lot more sophisticated, we've gotten a lot better ourselves to it being able to understand the full funnel impact of our content investments from the very top of the funnel brand level all the way

**[5:14]** to the down funnel lead QL and net customer ad perspective as well. And so we continue to refine that motion and just get better at being able to just sort of articulate that to our finance teams that, you know, for a lot of cases, this is kind of new. And so being able to have a really solid measurement strategy is equally important. - Yeah, because I think you could put a lot of investment in this. And if you're not really understanding where that's coming back, it's gonna be difficult to stomach doubling down and continuing to pour investment in it. And for smaller companies too, it's not just the economic investment,

**[5:50]** but it's also the time investment focus. So I think it's just really important to have that infrastructure in place, like you mentioned. - Yeah, yeah, I completely agree. And I think, you know, oftentimes whenever I talk to other media operators and software companies, this is probably the single hardest thing that they're trying to crack. You know, a lot of traditional marketing is, you know, direct response, brand marketing, experiential, and they all have their different set of KPIs for measurement. And content for the longest time, especially for software companies, was SEO. And so when that stops working, you have to sort of pivot

**[6:27]** or hopefully have it already diversified into more formats and more channels. And in a lot of cases, there's a harder to measure from a down funnel perspective. And so a lot of sort of media operators and software companies, but also B2C companies are really trying to grapple right now with how do you measure it? How do you articulate that impact in a way that makes sense to, you know, your C-suite, but, you know, continually, you know, improve that model so that there's this great feedback loop in terms of things that are working and are not working at all stages of the funnel. - So one of the parts I am so excited to go into,

**[7:03]** how do you build this arm of the business? What does the structure look like? How do you get talent? When do you know that it's time to spin up a new newsletter or a new podcast or a new channel? Operationally, how do you structure this whole media company that's living with inside of HubSpot? - Yeah, I mean, everything we do at HubSpot starts with the customer. You know, what is a customer pain point or opportunity that we are trying to solve for? And we kind of back into it from there. And so if you look at our entire media ecosystem, everything is verticalized within a topic or a category that maps back to a product skew within HubSpot.

**[7:41]** And so we have a vertical of marketing media brands, which maps back nicely to marketing hub. We have sales vertical and entrepreneurship vertical and AI vertical. And so wherever the TAM is, we use that as an opportunity and a signal to say, okay, do we have enough coverage here? And if not, should we potentially build something? Should we potentially collaborate with other known quantities within those different verticals, whether it's a creator or a journalist, or should we potentially explore the acquisition route, which we've done a couple of times over the last couple of years? And that's really how we focus on, you know,

## 08:09 — Structuring media around product SKUs

**[8:17]** really deciding what media brands we need to launch, what channels we need to be on. The thing that we found as well is that in areas that are maybe a little nascent for us, let's take like AI, for example, where up until a couple of years ago, we didn't really have a media brand explicitly talking about what's happening in AI and how to think about that and implement that within your own professional life. There's a lot of creators, right? And so we were able to really work with a lot of great folks that were already speaking to those AI practitioners in ways that we just weren't able to at that time. And it was also a good opportunity for us to realize

**[8:56]** that the pace of change within AI media was so fast that to start to build something from scratch and have to wait 12 to 18 months for that to become a thing just didn't make sense at all. And so through our creator partnerships, we were actually able to partner with some of the, you know, biggest and best voices in AI enough to understand, well, the ROI is there consistently month over month over month. And rather than try to build it ourselves, we could actually acquire those voices, bring them in and really scale them up in ways that were hard for them to do independently, but also allowed us to accelerate our distribution

## 09:32 — Build vs. partner vs. acquire

**[9:32]** to those audiences that, you know, are hopefully then becoming customers of HubSpot. - And I'm curious in this strategy. So you're reverse engineering from your ICP, what media and content would be interesting to them. When you make an acquisition and you've done a few large public ones and really successful ones, does anything change about the content? Do you start putting in HubSpot material? Do you start guiding it a certain way to lead it to a certain funnel that you're hoping that audience is going towards? Or do you keep it more or less the same and leverage it as intelligence to get your products out to them? - I would say the instinct, I think,

**[10:12]** for a lot of acquiring companies is to do the former, is to start to introduce your products and your brand message and your talking points in ways that just in my own experience, having been through a bunch of different acquisitions throughout my career almost always fails. It's more preserving editorial independence, arming them with a rich body of insights and data in terms of the things that our ICP responds best to and things that they don't just to inform maybe what topics they want to more aggressively pursue and which ones maybe don't make sense for their channels. And then just giving them more back-of-the-office resources.

**[10:51]** So more production resources, more growth capital, distribution, it's a huge one. Given month, we reach over 50 million people across our 17 YouTube channels and six newsletters, et cetera, et cetera. As an independent creator, you don't really have access to that. And so we never try to meddle with the editorial because the concern there is that by meddling with the editorial, you then meddle with the audience. If you meddle with the audience, then you meddle with the trust. And the very worst thing you could do is buy something and then evaporate the trust overnight and have to write down that investment. - Yeah, I love it. I love it.

**[11:26]** And I think there is probably such a instinct to do the former, as you mentioned, to say, okay, great, let's start pumping in a bunch of ads for our product into the thing. And then it's like, well, there's a reason they had an audience in the first place and they weren't going to their channel to CXYZ. But I love that, you're able to take something that they've done a good job and then just back them with resources and help them accelerate. It's gotta be really exciting for an independent creator too when they have access to resources that otherwise they wouldn't have been able to. - Yeah, I mean, it's resources,

## 11:27 — Why you never touch the editorial after an acquisition

**[12:02]** but it's also, you know, technical opportunities to be able to automate a lot of the things that historically for creators is a very manual process. And so like a really good example is, you know, whenever we acquired Starter Story, we actually worked with that team to develop an automated content clipping platform that is trained up on, you know, what makes a great viral clip and that consistently improves and improves with every single viral clip rep that we do, but then takes long form videos, identifies time codes that potentially could be the most viral clips and then pumps that over to a natural language editing software we use,

**[12:42]** and then allows the channel manager or, you know, in this case, the independent media brand to be able to, you know, really automate a clipping strategy that historically required hours, lots of freelancers, and whenever you're a small team, you just don't have a whole lot of that. And so I think they also find it's like the infrastructure is really great here and just, you know, has made a lot of our acquisitions really successful. - I think that leads to a good point. So being HubSpot, you have the resources, you have the audience already, you have well-defined ICPs. Let's talk maybe about a company that's earlier stage,

**[13:18]** maybe think they're in that series A, series B, they're scaling, they're growing. What does media look like for a company that's up and running? And how would you recommend a team like that get started? - Yeah, I think the principles still hold true, right? You're still trying to build a durable, always-on media engine that does just a really great job of providing unique value to the audience that you're going after. And you can do that through a bunch of different formats. But if I were advising a series A or a small company that's building up a media strategy, it would definitely be starting with video-first creators and video-first content strategies.

**[14:01]** And the reason I would go there is first creators, especially in the B2B space, while there's a lot of heat behind them now, they're still relatively affordable in terms of partnering with and having deep relationships with, oftentimes because they haven't necessarily reached the same amount of scale that a traditional B2C lifestyle publisher has, and the CPMs are a little bit more manageable. But it also gives you an understanding of what exactly does your ICP actually care about from a unique content perspective to inform your own content strategy, but then it determine, hey, is this a creator that I want to continue to go deeper with?

## 14:30 — Where a Series A/B company should start

**[14:36]** Or should I expand my scope of creators that I work with? And I think for a relatively affordable budget, you can start working with a lot of really awesome B2B creators within your content vertical to get a couple of reps in, understand what works, what doesn't, who works, who doesn't, and to start to form a potential way of either going deeper with them or even collaborating with them on original content. But then focusing first on video, and video being a format that might be a little bit more expensive to produce, might take longer to produce historically, but as a format is the currency of every single platform out there.

**[15:13]** Like if you think of X trying to become a video social app, you think of IG, already mostly a video app, you think of TikTok, natively a video app, you think of LinkedIn, desperately trying to become a video app. YouTube, obviously, it can be adapted for virtually every single platform that your ICP is on. At the same time, that video is a transcript. That transcript can be turned into an audio podcast, can be turned into a newsletter, can be turned into a net new SEO or AEO blog post. So you can really drive a lot of value out of that one video asset investment. And so that's how we think about it and why we're so video first, because of the versatility

**[15:57]** of being a video first media company. - Yeah, and I think a lot of people don't realize that. We do the same thing. So we have the podcasts. - Yeah, the flywheel. - It's an amazing flywheel where those, and it's not, I don't want anyone to listen to this and take it as like, oh, you're just like AI churning out slop content. Like, no, you're having conversations with people in a really organic format and you're getting your ideas out. And then those ideas end up on paper in the transcript. And then you can restructure those ideas, but it's still original content. It's just restructured into a format that you can post in different places. - Yes, yeah.

**[16:38]** There's always a human at the very start of something. And that's oftentimes where the originality, the tastes, the perspective, the lived experience comes from. You can't imitate that, but the middle part, right? The kind of like the pre-production, the scripting, the outlining, the clipping, the localization in some cases, like the things that historically had taken just so long in so many layers of handoff can be vastly improved through AI or automated in some cases. And then at the very end, at least as the case with HubSpot Media, nothing ever goes published until there's like a human that actually says, this is good.

**[17:19]** And if they can't say, this is good, go back and they make it good. - Yep, no, I think that human in the loop on the front end, original ideas, and then before it gets in public, super important. 'Cause if you pump out bad content, it could have the complete opposite effect. It's not just the volume, like, okay, great. I'm putting out a bunch of videos. If you're putting out bad videos, it's gonna hurt your brand and do more harm than good. - It's gonna hurt your brand. It's gonna hurt you algorithmically too. Like if your strategy you're building up on, as on YouTube or on Instagram, every rep that you publish is just as important

## 17:32 — The video-first flywheel: human, AI, human

**[17:55]** as the last one and a bad published video has negative consequences for subsequent videos you publish. And so it's really prudent for you to make sure that every single thing that you put out into the world is great from a brand perspective, but also just great so that you can continue to grow on the channels that you're investing in. - That's really, maybe if you don't mind, we can dive into that. I think for most B2B companies, they're primarily finding their ICP on LinkedIn. I know everybody else is on Instagram, TikTok, YouTube as well. So I know it's like, hey, just because you're targeting a CRO on LinkedIn doesn't mean that he's not also logging

**[18:35]** into these other platforms to consume content. But talking about the algorithm, I know they change all the time, but maybe specifically a little bit on LinkedIn, any learnings that you've had, having so many different channels and people that are posting through the LinkedIn platform, any learnings, any surprises or gotchas that people starting out first time might not recognize? - Yeah, I mean, I guess maybe this is kind of a quasi-controversial take, but I would say, while it's very clear that LinkedIn is investing heavily and it's a video product, it's still not yet a video platform. And what I mean when I say that is that there was this moment in time

**[19:20]** whenever LinkedIn was rolling out video natively to the feed and to the app, where it was very clear that video published to the platform was getting artificially boosted to the platform as a way of just encouraging more usage and more original content being published to the platform in a video format. And the thing that we've seen and that, I want to talk to other publishers, both in the B2C and B2B spaces, that they've been seeing a kind of precipitous drop in terms of just like overall distribution video. And I don't necessarily know if that's because of the quality of the video, it's maybe just because video as a format

**[19:51]** is continuing to kind of become saturated on the platform. But that's all to say that if you are starting out with a video first strategy, like I still am very convicted in that it starts with YouTube and then expands out to platforms like LinkedIn, where clips would probably make a lot of sense there. And that's probably where we've seen the most success is a really sophisticated clipping strategy, getting trained on past historical data in terms of what worked, what didn't to inform the next clip that gets published to the platform. And so I think that's where I would probably start is like making sure that your video strategy,

**[20:27]** no matter what you're publishing, is optimized first and foremost to platforms that have the right kind of scale, but then being very intentional and data informed about the type of content that is derived from that YouTube content and then published to LinkedIn. - I like that, so start with YouTube, see what's working on YouTube, take the highest hitting clips, shorts, or things that are working there and then use that to distribute. Well, is YouTube a friendlier ground to test in than maybe LinkedIn would be? Or are there some algorithms that are a little bit more forgiving than others? - I think with YouTube, you have the scale

## 20:38 — The LinkedIn reality check

**[21:11]** in terms of just like video consumption because it's a video platform first and foremost. And so you're gonna get a lot of rich insights early on in terms of things that audiences like and don't like. With LinkedIn, especially if you are smaller on the platform, you might not get as much signal as you would on a platform like YouTube. And so that's why I think I keep coming back to like the opportunity of using YouTube as a testing ground, learning a lot there, perfecting a strategy, and then thinking of other platforms like LinkedIn as not derivative of that YouTube content, but a great opportunity for finding more distribution

**[21:45]** for that content on new platforms. - Makes a ton of sense. Talent. - Yes. - A lot of these companies are not used to recruiting, looking for, or even know what to be looking for in talent for building out media at their company. And I'm sure there's a few different things you need. There's probably the architect of the media strategy, and then maybe that's a more traditional marketing-ish type of person, but then you have to have the talent. And how are people building these and getting the right team put together to actually make an impact with a media arm? - Yeah, well, first of all, I mean, you shouldn't overlook your internal talent.

## 22:25 — YouTube as the testing ground

**[22:34]** We have such great internal talent at HubSpot that have become regular fixtures of our content strategy, both video, audio, and text, across HubSpot media. And so for anyone that's starting out, I would definitely focus in on there to see, does a talent already exist? Do they have a unique point of view? Are they great on camera? If not, do they make more sense for newsletter or for podcasts or other formats that aren't so visible? But starting there, but then I think you're right. We've made a number of hires, like amazing hires from non-software and B2B companies, largely the Axioses and the BIs and the Informations

**[23:15]** and the Morning Brews and the Onions of the world, just like places that are known for great business content, but also not boring business content, or in some cases as the Onion, no business content at all, just like really sharp, funny, irreverent editorial. And so finding folks that come from non-traditional backgrounds in the software and B2B sense, bringing them over and then giving them the infrastructure, the production capabilities, and then just a better incentive structure, 'cause in traditional media, you're really trying to get impressions. Like you're trying to just generate content that gets as many clicks as possible,

## 23:28 — Hiring journalists, not marketers

**[23:54]** as many unique opens as possible, as many video views as possible, and sometimes those are the wrong incentives. Sometimes those are the incentives that cause you to create things that maybe don't really provide a lot of original value or get people to do something like become a lead or become a customer of HubSpot. And so the incentives we give them are like creating things that are quality over quantity, that are high intent over no intent, and ensuring that everything we put out into the world while it is meant to be entertaining and voicey and fun and shareable also provides a lot of value that gets people to want to, in some cases,

**[24:32]** press pause or click a link and then go and take a deeper action with HubSpot. And so that's kind of how we think about talent strategy, but also like ensuring that they have the right incentives when they come to a non-traditional media model so that they're set up for success. - Oftentimes, especially in B2B software, the founder at early stage will take the lead on doing content. When do you think that makes sense? And when do you think it makes sense to hand it down to other people or start scaling beyond the founder being the only person who's the face of the brand? - Yeah, I mean, founders have big jobs and I understand the desire sometimes

**[25:11]** for early stage founders to want to be the face. And I think that could still be part of the strategy, especially if you think about it from a thought leadership perspective where maybe she or he are more focused on LinkedIn, on X, things that don't necessarily take a whole lot of their own bandwidth to produce content for. But the thing that you're gonna find is that, a great founder isn't an expert in everything. You need to find people that are experts and the topics that your ICP really cares most about. And sometimes that is going beyond the founder and going to folks internally that maybe are those subject matter experts, that are the RevOps experts,

**[25:46]** that are the social media marketing experts, that are the AdOps experts, that are the content marketing experts and giving them a shot at it. Training them up as onscreen talent or editorial talent or, as we were just talking about a second ago, maybe finding those folks externally, because in a lot of those cases, those folks also have their own embedded audience. These are reporters and journalists that come from really great business and marketing backgrounds, but have huge LinkedIn and X followings themselves and can bring that as added distribution to your organization. So there's pros and cons to both, but I would say there's probably never a world

**[26:21]** where the founder or the CEO doesn't play a role in the content strategy. It just depends on at what level do they need to play and how much do they actually need to be really involving themselves or investing in the day-to-day content operations. - Yeah, it makes sense. And I know some have some predispositions to doing content versus others and they can maybe lean in there. And you've got to play to the founder's strengths too, but I know I'm spending a lot of time on the talent side of this, but I'm just, I think this is a part that's gonna be a real big mental block for some companies to overcome. Like who do we hire? What are their titles?

## 26:32 — Should the founder be the face — and where media should report

**[27:00]** What are their roles? - Yeah. - If you're kind of building out like your first, okay, it's not the founder anymore. We're getting people dedicated to this. Do you roll it up under marketing? Do you have someone who's dedicated to a particular channel or a particular form of content? How do you kind of structure those smaller earlier teams to be set up for success and make sure you have the right leverage out of the people on the team? - I'll be honest. Today, our media strategy is under marketing and it makes sense there because we have a fantastic CMO and he believes in the power of media and there's a lot of great autonomy,

**[27:40]** but also close collaboration with other parts of the marketing department. And there's not a perception that content has to be product marketing. Content is just really great editorial content that engages people in a way that is native to the platform that they're on and convinces them to take a deeper action with HubSpot. For an early stage organization, I would almost argue that shouldn't be in marketing. And the reason being is like the worst thing that can happen is you spend a lot of capital, hire a lot of great editorial talent and that it just gets perceived as marketing, like traditional marketing, it becomes like a vehicle

**[28:17]** for your product marketing messaging, your sales and alien messaging, your thought leadership messaging, and 9 times out of 10, it's just not interesting content. It's not things that people actually wanna watch or listen to or share. And so I would argue that like for early stage organizations, like have that content team report to the CEO. Like there's no one better or the founder, right? Like there's no one better in the organization that knows what the brand needs to be across all touch points than the founder of the company. And so I would argue that early stage, keep it close to the founder as you scale,

**[28:49]** probably untenable for that team to continue to report into the founder of the CEO, in which case, by then you probably have a good enough strategy and point of view on what content should mean for your organization where it doesn't matter where it lives, engineering, marketing, they're still gonna do what they do best. - Yeah, I like that. And I do like, I mentioned earlier in the conversation too, I have an intuition of the value of what the content is doing for lean scale. And I know even if I can't track every single lead and have a perfect like do X amount of videos, get X amount of sales, I know that it's helping every single part

**[29:27]** of the sales process and it's helping us grow our business. And it's also actually in a lot of ways forcing us to have an opinion on things and forcing us to really reflect and think about what's happening in the market, what's happening for our customers. And because we're on the hook to put out content that's interesting, we kind of have to stay tip the spear, which becomes a flywheel for our service and products that we build. So I think there's a lot of, it's not as cookie cutter to get the ROI, but if you're in it, you can see it across your whole company. - Yeah, I mean, it takes a significant amount of trust. I'll say that out loud.

**[30:07]** As sophisticated as I think we've become with measurement, it's still not perfect. And it's still a far ways away from being perfect, though I strive for perfect with our measurement strategy, but there is this leap of faith. And I think like what I always say is like, put yourself in the shoes of your own purchase behaviors. I mean, you're not gonna buy something you never heard about or have no familiarity with or don't believe in. And so if that's to be true, and we all universally believe that, then why would you do the same for a CRM or a piece of software that's probably more expensive, takes a lot more decision makers to decide on,

**[30:41]** isn't something you're in the market to buy, like on a given day, usually it's about 5% of the year that you're probably deciding on potentially changing your CRM or buying your first CRM for the very first time. And so there's a lot of just like the intangibles of it all that does require, I think a lot of trust across the board. - What is the biggest mistake a founder or early stage company could make when venturing into building an in-house media team? - Yeah, that's a great question. I think the first thing is not truly believing in what media can and should be. And what I mean by that is I think oftentimes it's a checkbox or it's a thing you need

**[31:29]** or you think you need to do. And you're kind of thinking about it as like another part of your overall marketing strategy, but you're not willing to make the commitment nor the investment. And the investment doesn't have to be like a significant capital investment, but it's not cheap. Like you need to find really great talent. You need to find great producer editors that are full stack video creatives. They can pitch, they can outline, they can script, they can produce, they can even in some cases edit and publish, like they can own the end to end life cycle of their craft. You need folks that are really great at like newsletter editorial, for example,

**[32:08]** like sure that can be automated, but the best ones aren't. And the best ones are largely human driven, but are supported by AI to be able to increase frequency and A/B testing and things like that. And so just being able to like hire for taste is a really important aspect as well. And so I do think it's like just being committed to it and really believing in the power of content, sort of how you were describing it a second ago and how you've been chatting about it throughout this entire conversation. I think also sometimes there's this kind of instinct to outsource it, potentially to an agency, like a big agency that purports to be really good

**[32:50]** at content or social, what they're doing it for like 30 other brands and what they're giving you is just like probably AI generated and they got their B team on it and it's not gray and you pay a lot of money for it and they're sending you these reports of how many impressions they got, but 99% of it is bought. It's just like you can fall into that trap pretty easily without really knowing about it. So I do believe like if you're a small business and you really wanna do it and you really believe in it, it's like you probably got a small squad of folks that you're hiring for them and like you really have to be able to let it cook for a bit

## 33:09 — The biggest mistake founders make

**[33:22]** and not expect overnight results 'cause in some cases it can be a slow burn and it doesn't have to be 18 months, 24 months, but at least giving it a year to be able to like really mature and find its focus and its footing. - Yeah, and I would say that's,

**[33:43]** I'd say it took us about two years before I started to feel like, oh, we're now, this is now compounding, this is now something that is really, really moving the business forward and I think in the early stages, it wasn't as risky to put out B level content, C level content even. So I think that was okay with where we were at. - Yeah. - And I think the biggest mistake I could have probably made is to just stop and not stick with it and keep going because then you know you're not gonna get, it's like going to the gym for three months and being like, oh, well, it's not really working. It's like, no, you gotta hang in there for a couple years,

**[34:25]** you know, and then you'll really start to see results, but it's tough. You have to really, like I said, have the stomach for it and keep going through those times where you don't get a lot of likes on your post, you don't get a lot of views on that video. It seems like you have a million other things to do and like, is this really, should I sit here and make a video that's gonna get a couple of likes when I have like 10 million other things to do? No, you have to be really disciplined to keep moving it forward. - Yeah, I think that's very well said, like being very disciplined, not giving up, putting in the reps, but then I also think,

**[34:57]** you know, being willing to say to yourself, this is not good. Like the thing that I'm creating isn't providing a whole lot. - I was pretty good at that part. (laughing) It's like, this is garbage. I don't even know if I want my mom to watch this thing. This is bad. - I mean, a lot of people aren't and it takes a lot of vulnerability to be able to admit that, but the worst thing you could do is just keep going at it and like doing all the right things, but it not being something that actually provides in the middle of the value or is different than everything else out there. And so I think it's like definitely both sides of the coin to be able to find success.

**[35:33]** - Throughout your journey of building out this team and this department, were there any pleasant surprises, pleasant things that you weren't expecting that happened by focusing on building media within HubSpot? - Yeah, so I think some of the ones have been really focusing on using our creator program as an incubator for potentially new content co-productions or acquisitions. Like what I found in a lot of these partnerships is that there's always something that you don't really know is there until you start working with them on a deeper level. Like a good example is, whenever we acquired Start Our Story,

**[36:16]** we acquired them because they reached a great kind of like pre-seed or series A founder. They spoke with a lot of authenticity. They had great editorial talent, great distribution. And we're trusted by their community. What on the thing we didn't realize is like how good they are at production, just like end-to-end content production. It's like a well-oiled machine to, in a way that like small businesses have to be because they don't have the luxury of having a lot of people, a lot of freelancers, a lot of time. And there's just so much that, I think our own video strategy has learned from and evolved as a result of that acquisition

**[36:57]** that people would have probably paid hundreds of thousands of dollars to be able to get insights into that just came as the result of going deeper with a partner that we had really enjoyed working with over the last couple of years. So there's things like that where like, I feel like the unknowns are oftentimes like the most exciting parts of this job. Like another has been, how we have been able to really expand some of our biggest YouTube channels in ways that, it's easy to kind of get into this business as usual motion for content strategies. Like I found a format, it works, I'm just kind of keep doing it and that works, right?

**[37:38]** But then you start to see diminishing return or you run the risk of being over leveraged in a single format. And so I do think like some of the most fun I think we've had as team is just like being comfortable as saying like, you know what, like let's pause for a second. Let's like experiment with a bunch of different formats, try different things, we don't think it's gonna work or maybe it will work, we're not really sure, but just like getting it out there and being vulnerable and using that as an opportunity to diversify how you create content and provide value for audiences is just something that, you know,

## 38:01 — Surprises, experiments, and where owned media goes next

**[38:11]** you don't really always have the luxury of doing just because like you just can't feel like you're on this hamster wheel of creating content. But that is also just something that like, you know, I think we've gotten really good at and have been like pleasantly surprised on the results from and like not everything's a win. I would say like, you know, five times out of 10, they don't and it kind of duds, but the other 50% are the things that continue to help you evolve your strategy that you can then take, pick up and place on other channels and continue to expand them that way. So this is just like a couple that, you know,

**[38:43]** I think like I've been personally excited about. - Yeah, it does feel like it's a never ending game where if you look even every couple months, it feels like there's new things that are working, new things that are being rewarded and like you have to keep up with it. You can't just sit back and wait to see what happens. I'm curious, I would love your insight. Where do you think this is going in the next six, 12, 24 months? I mean, there's so many things that are different. There's AI capabilities that are coming into the game. There's more competition coming in where people are realizing, hey, this is a big opportunity. So let's start investing.

**[39:21]** So there's more companies that are trying to get the attention of the audiences. What big things do you think are gonna happen next? - Well, I think you're gonna continue to see a trend of software companies building out larger content in media arms and you're starting to see it. You see like kind of these like head scratcher acquisitions like TVPN, but you also see like really smart companies that are building up really great media strategies within their organizations that help them reach audiences in ways that aren't as fleeting as like paid media is. And so I do think you're gonna start seeing like more acquisitions within the software space

**[39:59]** of other media companies or a great editorial talent from non-traditional media models like B2C. I think for HubSpot Media at least, like we really are focused on continuing to grow our existing portfolio, but grow them not just in the traditional sense of more video output, but more brand extensions. Like how can I take something like My First Million, which has a really rabid fan base of folks that turn up every single week to hear from Sam and Sean and their guests. How can we expand that to potentially more live events, more digital community products, more webinars, more meetups, just things that like, allow audiences to form stronger,

**[40:39]** more visceral connections with our hosts, but create this sense of community, which again is, it kind of goes back to this kind of like harder to quantify measure part of it. But like as brand builders, like we know it's really important and just adds to the overall value of being a subscriber of My First Million. You can see the same thing being done for marketing against the gray starter story. Like for starter story, we just did an event coming to your tech week. We're gonna do more of those, right? It's like building out horizontally for all of our media brands, especially the ones that are very talent first.

**[41:14]** And then I think going deeper on creators more generally, we already have a great bench of 150 creators, like in my vision, that should be 300, 450. Like there's a lot of great creators across a lot of verticals that are really important to us. And so while we focus historically on larger niches, like marketing and AI and sales, getting down to like micro niches, like GTM engineers or RevOps leaders, or creator to talk about content creation, things that we know are really important to our business portfolio products are gonna be areas that we're gonna continue to expand out horizontally. And while that might not be like the biggest

**[41:52]** in terms of subscribership, they probably have, in a lot of cases, the most influence for the audience that is that we really wanna go after within those different content verticals. - I think that's a really interesting aspect that not a lot of people are talking about when they're talking about building media. I think there's a huge desperation for in real life events. And I personally haven't thought about bringing those two things together, but you're right. Like that's how you get a closer connection to who the creator is. That's how you can add more meaning and expand your fan base or audience too. I think that's a huge unlock

**[42:32]** that people can take advantage of. If they've built up the big enough audience to where those things make sense, I think that's a massive accelerant. - Yeah, no, I couldn't agree more. And I think we've seen some really great signals from that strategy. And it doesn't have to be showing up at the can and spending millions of dollars kind of thing. I mean, it can really just be like meetups at South by Southwest or Unbound, which is our event we do in Boston every September. Just things that give people the opportunity to go deeper with the brands and the talent in ways that sometimes you don't get enough satisfaction from that kind of digital experience.

## 43:10 — Inbound is dead: enter loop marketing

**[43:10]** - I'd be remiss if I didn't say that everything that we're doing is just like one part of a larger shift in how marketers are doing marketing today. And I know this is like a little out of chronology for the conversation, but we talked a lot about how just the top of the funnel has been completely disrupted. And whenever we first started talking about how to do marketing effectively and how to build marketing teams 15, 20 years ago, especially for B2B, we coined a term called inbound marketing. And that kind of became the playbook that everyone used. And I think we're officially saying that inbound marketing no longer works the same way.

**[43:47]** And that's being replaced with something called loop marketing, which as its name implies, is a way to really think differently about how to drive compounding growth in your marketing efforts in partnership with AI that is constantly learning, but constantly compounding across pay media, creators, content, et cetera. You know, we're publishing a book, September 22nd through Simon & Schuster. So that's on pre-order right now as well at loopmarketingbook.com. So for folks that are interested, like all the things that we talked about, there's a lot in there from that, but then it goes a lot deeper across the entire spectrum of marketing.

**[44:24]** - Yeah, and I think there's so many things that are changing on the inbound side, on the outbound too. I know that wasn't necessarily a topic that we recovered on this, but I think creating meaningful content and warming up your audience really helps accelerate outbound activities too, which there's so much noise on the outbound side as well. It's like, if you're not standing out with really good content and they haven't heard from you before, they're not gonna be interested to pick up your call to talk about a particular product. And I think the hyper personalized LinkedIn outbound is just, it's not working

**[45:02]** unless you have something of substance behind it as well. So I think, and that's where these investments just like surprise you in so many ways. They'll surprise you on the product, they'll surprise you on the service, they'll surprise you on the efficiencies you start to gain on inbound and outbound, and then just the brand reputation you have. And I also, another thing, we didn't talk about this too much, but I think being in a company that is serious about media is really good for retention too, because you're working at a place that has a presence, you're working at a place that is known, it's cool. It's cool to work at a place

**[45:39]** that is putting out content people like to watch. - Yeah, it's nice to have your spoiler britches to be able to pull from really smart people and 20 years now of amazing data sets and insights to be able to create the foundation of what today is HubSpot Media. So you're right, I mean, it has a lot of benefit to not having to start from scratch from like a brand reputation perspective. - 100%. Well, Jonathan, I appreciate everything you shared. You are paving the way for what media looks like in the world of tech. And so many people are trying to just emulate a small piece of what you're doing. So I'm really impressed with what you are doing.

**[46:26]** I agree with the bets and the strategy. We're seeing it ourselves and the scale that we're at at Lean Scale right now. And I really appreciate the practical playbooks and roadmaps and just opening up so people can really get a lot of this conversation. So thank you for being on the podcast. I can't wait to see what you and HubSpot do next. And I know there's gonna be a never ending involvement of what you're doing. So just appreciate being here and appreciate what you're doing. - Thank you so much. (swooshing)