Inside HubSpot’s Media Machine with VP of Media & Content Jonathan Hunt

10 Aug 2026 · 27 min · 10 chapters

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In short

HubSpot Media’s “media machine” and how it turns creator/audience attention into HubSpot customers while preserving creators’ editorial trust. It covers building vs buying, creator program mechanics, valuation signals, and AI’s role in scaling content.

Guest background

Jonathan Hunt is HubSpot VP of Media & Content. Previously worked at Vice, Vox Media, National Geographic, and Complex, focusing on audience development and translating major media voices/IP for modern digital platforms.

Key claims

HubSpot reaches 50M people/month via 17 YouTube channels, 6 newsletters, websites, and podcasts, plus a creator network of ~150 creators. They invest to stay present across ~27 touchpoints and ~6–7 decision makers before software purchase. Acquisitions usually start from creator-program ROI testing; they avoid disrupting editorial voice. AI augments production (idea testing, scripting, atomizing long-form into clips) with humans in the loop.

Notable examples

Acquisitions include Hustle (newsletter-first), Mindstream (350K AI newsletter subscribers), Futurepedia (2.1M YouTube; Skill Leap, Beehive-based properties), Starter Story (solopreneurs/small business builders), and TBPN (discussed as a deal HubSpot likely wouldn’t do). Video is prioritized for higher engagement and repurposing into many assets.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

Tap a time to open that second in VO

The Evolution of HubSpot Media

1:08 to 3:17

Discover the transformation of HubSpot from a software to a media-centric business.

“Jonathan, how would you describe HubSpot Media?”

Jonathan's Background and Insights

3:17 to 5:51

Explore Jonathan's previous experiences and how they shaped his approach at HubSpot.

“And since then, we've continued to build new media brands and properties, but also buy a few others as well.”

Evaluating Acquisitions vs. Building Media Brands

5:51 to 8:10

Understand how HubSpot assesses opportunities to scale through acquisitions or building.

“So I know that you've made a couple of recent acquisitions.”

Post-Acquisition Strategy with Creators

8:10 to 10:24

Learn how HubSpot supports creators after acquisitions without disrupting their voice.

“And it's a great way for us to also test the waters for whether it might make sense to potentially acquire those creators.”

Valuations and Trends in the Creator Economy

10:24 to 14:00

Gain insights into current trends and valuations in the creator economy.

“And, you know, most recently we did it with small business builders like solopreneurs, pre-seed business builders through our acquisition of Starter Story.”

The Evolution of Media Strategies in the Creator Economy

14:00 to 17:06

Learn how HubSpot is adapting its media strategies in the creator economy.

HubSpot's Creator Program: Collaborations and Monetization

17:07 to 19:19

Discover how HubSpot collaborates with creators and monetizes content.

“I mean, it's a cool part of our strategy as well, diversifying the creators across different platforms.”

The Role of AI in Content Production and Strategy

19:20 to 22:45

Understand how AI enhances content production and creator partnerships.

Future Plans and Growth for HubSpot Media

22:46 to 25:11

Explore HubSpot Media's future initiatives and growth strategies.

“So we're 60 folks that spread across content, monetization, and audience development.”

Advice for Creators: The Importance of Diversification

25:12 to 26:25

Jonathan emphasizes the importance of diversifying content across platforms.

“speak today before we wrap up i just wondered if you had any words of advice for creators listening based on your experience working with them at HubSpot?”
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Transcript

Automatic transcript. May contain errors.

0:07Ian Shepherd:Jonathan Hunt is HubSpot's VP of Media and Content. He's helped build a media operation that reaches 50 million people a month across YouTube, newsletters, podcasts, and a network of creators. We work with 150 different creators across different verticals like marketing and sales and entrepreneurship and engineering and AI. And it's a great way for us to test the waters for whether it might make sense to potentially acquire those creators. In this episode, we talk about what makes a creative business worth buying and how the company turns an audience into customers without taking control of the editorial voice.

0:43We don't go in there and say, hey, now you're a corporate mouthpiece for HubSpot because why would you do that?

0:48Ian Shepherd:I also asked Jonathan some fun questions, such as whether HubSpot would have bought TBPN. We probably would not have done a deal like that. But I guess my kind of TLDR is like, I think it's really great for the creator economy and hopefully opens up new opportunities for other creators to get really good deals. And so the big question is, how does HubSpot value a creative business? Let's jump straight into it.

1:15Ian Shepherd:Jonathan, how would you describe HubSpot Media? HubSpot Media is a media company within HubSpot, the software business. It's a strategy for us to be able to reach 50 million people every single month through a network of owned and operated channels. And so today, you know, we own 17 different YouTube channels that reach marketers, sellers, AI practitioners, business builders, but also six newsletters, a number of websites, and a number of podcasts as well. We also operate a creator network that's about 150 different creators that fit within content verticals that are really important to our business and allow us to just reach more audiences that maybe haven't heard of HubSpot but should and to really influence their sort of software decision making process.

2:03Ian Shepherd:Excellent. Well, I'm really excited to get into it. Now, what was, do you know that moment when there was that shift between just being sort of a technology or software business and investing in and growing media brands? What was that? Yeah, I think where we started to see the need to invest and own and operate in media was when we started to see the fact that the top of the funnel was just getting more fragmented and wider than ever before. Like your website was not the primary destination where people were discovering you was Reddit, it was G2, it was LinkedIn, it was YouTube, it was newsletters, it was your friends WhatsApp group, it was a bunch of different touch points.

2:38And today, you know, it's about 27 different touch points and about six or seven different decision makers before somebody even decides to buy a piece of software, which is completely different than what it looked like even five years ago. And so it was almost a forced need for us to think differently about how we stayed present in people's lives throughout the 95 % of the year that maybe they weren't in the market to buy software so that when they were in the market, they chose HubSpot. And so that was really the impetus. And it started really with a blog, as most businesses start, but then really accelerated into an owned and operated media network when we acquired the hustle about five years ago.

3:17And since then, we've continued to build new media brands and properties, but also buy a few others as well.

3:23Ian Shepherd:excellent well it'd be great to get into that strategy and before we do i'd love to learn a bit about your background uh i know you've worked at vice and vox what did you see in that time there and what brought you to hubspot yeah i think what brought me to hubspot from those experiences was just the role that voices like individual voices were playing in how people's decisions get influenced right and so whenever i was at vox media for example you know i was really leading our marketing operation and our audience development strategy and like how do we get in front of more people but also take voices like kara swisher and neilai patel ezra kline and get them in front of more of the audiences that should know who they are at national geographic it was somewhat similar in that you know it's a brand that had been around at that time for 130 years and was hundreds of amazing photographers and explorers that were going to parts of the world that probably you and I will never get a chance to go to.

4:24And we're bringing back these incredible stories that the world needed to know. And my job there was like, how do you take all that and then translate that for a modern audience that wasn't reading magazines, wasn't tuning into TV stations, but instead was going to YouTube, Instagram, you know, experiencing this through AR and VR experiences, listening to podcasts. And that's the strategy that I was running there. And the same thing with Complex, you know, which was really largely built around folks like sean evans for example who you know hosts hot ones you know joe lapuma who owns sneaker shopping like you know these voices that were really important within the cultures that they existed in and how do you get that ip and that expertise and that voice in front of millions and tens of millions of people and i think the opportunity to be able to translate those experiences both working more closely with creators and subject matter experts but to be able to do that and scale that to really drive real business impact was something that got me excited.

5:24And then the opportunity to do that in a non-traditional media environment. You know, my background was very much in B2C media, working at Vice and Vox Media National Geographic and Complex. And this is a software business at the end of the day. And what we do is we sell solutions and help people grow better. And so the economics of how we operate are very different and how we monetize that attention and that inventory we generate is very different as well. Cool.

5:51Ian Shepherd:Well, let's get into it then. So I know that you've made a couple of recent acquisitions. What's the sort of thought process that goes through the business when it comes to looking at scaling new opportunities and making investments? Yeah, well, oftentimes how we evaluate that is it's either a build or a buy. And nine times out of 10, we'll probably build. The economics are more favorable. You oftentimes are committing to the fact that it's going to take a little while. But if you do it right, you can see pretty, pretty large compounding growth. And we've done that a number of times for different media brands within our portfolio.

6:24But there's some instances where the opportunity is so great that to spend 12, 24 months building something just does not make sense. And so the topic of AI, for example, was something where, you know, as an AI first software business, where AI sits horizontally across everything that we do to spend 12-24 months trying to build you know a definitive ai media brand um you know by that time you know you're like left in the dust like everyone else has sort of beat you to the punch and you're no longer a thought leader you're sort of trying to catch up and so for us they're like the opportunity to acquire ai media brands and you know overnight become the largest AI media brand's full stop was something that was really interesting to us and has allowed us to not only drive greater AI thought leadership for HubSpot, but also expose more audiences that should know about our AI offerings at scale.

7:23And so that was the impetus for us to buy Mindstream, which was an acquisition that we made about a year and a half ago. So Mindstream is a newsletter. Today, it's about 350 ,000 subscribers, but really focused on how to make sense of all the AI news that is happening on an hourly basis and to provide really thoughtful perspective around what it means for business builders we acquired futurepedia skill leap and how affinity so a trio within a larger media property called futurepedia that you know is 2.1 million youtube subscribers that are more focused on implementation so you know you hear about cloud design um you hear about the latest update um you know chat gpt's model how do you actually master that like within the day that it's launched so it's really like how do you take information and then apply that to improving your career or becoming better at the tools that you know are launching or changing every single day um and so that for those three to four acquisitions has allowed us to become the largest ai media brand um you know within the industry and has also just allowed us to do something that you know we could have probably tried to do ourselves but would have taken way too long makes sense makes sense and as someone

8:36Ian Shepherd:who invests into creators and sort of analyzes creative businesses myself i'm really fascinated from your perspective how do you assess opportunities to invest into so what's nice about how we operate is that acquisitions that we do oftentimes originate from our creator program So we work with 150 different creators across different verticals like marketing and sales and entrepreneurship and engineering and AI. And it's a great way for us to also test the waters for whether it might make sense to potentially acquire those creators. And so oftentimes we're working with them on a one-off or we'll work with them for three months, six months, 12 months.

9:17And if we can continue to see consistent ROI month over month in terms of qualified demand that they're able to generate, and then the down funnel ability for that demand to turn into high ASPs or really good MRR, then it's a signal to us that, hey, maybe there's an opportunity to go deeper. And deeper might mean working with them across more channels. And in some cases, it might mean seeing if they're interested in being acquired by HubSpot. But that's not the only kind of criterion that we use. We also try to see like, you know, are these people that like working with us and do we like working with them?

9:54Are they at a threshold of scale, right? Like, can they allow us to reach people, like net new people month over month in a way that historically you would have to buy against through paid media means to be able to do? And then, you know, do they reach an audience in a segment that is really important to our business that maybe we are not able to really reach organically ourselves that they've already established the trust and credibility within? And so that was really the impetus for us to do with AI. And, you know, most recently we did it with small business builders like solopreneurs, pre-seed business builders through our acquisition of Starter Story.

10:33Ian Shepherd:Really fascinating. I mean, obviously quite different to how we look at it. I'm curious how you work with the creators after you make an investment. What does that look like? Yeah. So the thing we don't do is we don't try to radically disrupt the editorial strategy. And my feeling is that what never works is whenever someone acquires a creator and then they're like, okay, well, this is what you know how to talk about. It's like you instantly destroy the trust and credibility that's been built up over years overnight by doing that. What we do do is we focus on the backend stuff, like the economics and the monetization model.

11:13Like how can you really turn all this great trust and attention that this creator has really worked hard to develop and translate that into interest for HubSpot? And so what historically might be a pre-roll or a mid-roll or a live read from the creator becomes a lead magnet where, you know, you might be watching an episode of My First Million, for example. and Sam and Sean are talking to Scott Galloway. Well, you know, within the first 20 % of that video, you'll probably get hit with a piece of content like a lead magnet that is really complimentary to what Scott Galloway, Sam and Sean are talking about, but provides unique value that causes you to want to press pause and click on that link and go give us six fields of contact information to be able to be considered a new lead and then nurtured hopefully into a customer of HubSpots.

12:03and so we try to really focus on how can we improve the business engine but then how can we also give them things that that you know would be things that would have been hard for them to do on their own as a oftentimes solo business so marketing support both organic and paid you know we have that massive network you know media channels i talked about earlier on how can we apply that and give them distribution that you know instantly gets them in front of 50 million people overnight in which case they would have probably had to organically engineer themselves or buy themselves how do we give them paid media distribution especially in areas where they have newsletters um and then how can we also build up their own personal brand so you know we have you know yearly event that we do in boston called unbound um it's 13 000 people and you know we just released uh you know the lineup but it's going to include um tom brady the tbpn guys like really like the who's who of kind of like modern culture how do we get them on stage there as well speaking and really like evangelizing their own subject matter expertise and so there's a lot of perks to being part of our creator network but also acquired by hubspot that doesn't really impact the editorial strategy there are instances where an ai youtuber that we acquire might be talking about a topic that we have a product for that will say hey look like maybe there's a different way of thinking about the live read or the lead magnet in there.

13:29But we don't go in there and say, hey, now you're a corporate mouthpiece for HubSpot, because why would you do that?

13:35Ian Shepherd:Yeah, makes absolute sense. No, it's really fascinating. And obviously, there was the recent acquisition of TPPN. I'm curious from your perspective, how you're sort of seeing valuations of creative businesses and how you think about that. It's a really interesting time to be a creator. It's an really interesting time for multiples and values of organizations i mean i think what tbpn did was fantastic and it's great for the creator economy and john and geordie are great talent and the production value of tbpn was awesome and they get great guests um is it is it to the value of what they got acquired for maybe to open ai we probably would not have done a deal like that just given the scale and how we value attention and influence but i guess my kind of tldr is like i think it's really great for the creator economy and hopefully opens up new opportunities for other creators to get really good deals yeah i agree i agree and what about different mediums whether it's newsletters or podcasts or youtube is there something you think is particularly hot right now or working well for you yeah i mean you know we we are very bullish on video we made a pretty hard pivot into video you know a number of years ago largely because as a format it's pretty universal you know every single social platform today is a video platform and algorithmically they're prioritizing it and they can also charge higher cpms therefore they prioritize it a long form video can be atomized into a bunch of different clips that can give you a halo effect across a bunch of different platforms so you're not having to recreate over and over and over again it's one asset gets turned into hundreds of assets it can also be repackaged into text into audio and so therefore it makes sense to be able to distribute through newsletters and through audio only channels as well and so it's just such a versatile format and what we're also seeing is that from a engagement perspective we do generate at a higher conversion rate through video on youtube and other video platforms than we do in traditional formats and so that's why we're so heavy on youtube video particularly as a format oftentimes whenever we are partnering with a creator or considering acquisition it's usually through the lens of do they have a really large established video presence that operates at a high enough production value and has a large enough audience that would make sense for us it goes beyond that like what what what what what what we try to avoid is creators that only have one channel it's just like a lot of risk right uh we try to focus on creators that have hedged and have presences across newsletter, ideally a couple of social platforms as well.

16:15And in some cases have websites that they operate that generate a large amount of traffic as well. And so as we look through the sort of evolution of our acquisition strategy from the hustle to Mindstream to StarterStory to Featurepedia, what you see is with the hustle, very newsletter first, plus a website, Mindstream, newsletter first, but it was built on Beehive. Therefore, there was a website as well, but the website was more secondary. But then as we evolved through StarterStory, It's large YouTube, large social presence, plus a website, plus a newsletter, and the same thing with Futurpedia as well.

16:47And so we really try to be very intentional around, like, are they as diverse as possible so that they've hedged in a world where if tomorrow, you know, your inbox gets summarized through AI, therefore you have no reason to open an email, which is starting to happen. If that goes away tomorrow, are we just like, do we write it down? No, in a lot of cases now we have YouTube and social platforms as well where we can pick up some of the slack.

17:11Ian Shepherd:That makes absolute sense. I mean, it's a cool part of our strategy as well, diversifying the creators across different platforms. And particularly thinking about email as well and whether that gets summarized by AI moving forward is scary, just the impact it might have. Absolutely. And you touched on the creator program. I didn't realize it was so big. Can you tell us more about that? Yeah, so the creator program we've had now for about five years. And it started as an audio first approach where we're working with a lot of the larger niche marketing podcasters and business podcasters and then evolved it to become more of a multi platform approach.

17:49And so oftentimes we're working with them not too dissimilar to how we monetize our own properties where we're collaborating with creators on original content that becomes live reads, which are lead magnets that are hard coded within the content they're publishing. and then we work with them oftentimes on bulk buys so rather than doing one-offs which we do sometimes if we're really starting to just like test the waters with a certain creator we try to do something which takes some of the pressure off then because as a solopreneur like the thing that you probably don't want to be doing is like doing a lot of bd all the time like you really just want to create the thing and so can we de-risk that for them where we're buying up you know two videos of the four videos they publish on a given month for three months which then allows them to create better products on screen but then also can we do it in a way that consistently shows roi and so where we're working with them to give them insights and feedback on things that are working not working so that they can fine-tune how they work with us and then oftentimes that then evolves into working with them across more channels for longer periods of time one of the big reasons why creators really love working with hubspot creators and why i got hubspot media network is that it's not a transactional relationship.

19:02I kind of alluded to it before. Oftentimes, we're also finding ways to work with them as on-camera talent for our own content that we're producing, which has its own different set of economics. We're bringing them out to our events, whether it's Unbound, but then we do hundreds of events in different regions at different scales that we try to bring them out to really as subject matter experts. And we also find opportunities for them to get distributed across our network when and where it makes sense and so you don't really get that with traditional creator networks or agencies or whenever you're working with like a big fortune 100 brand where it's just like you are one row in a media plan we don't think about it that way we really think about as a relationship first and foremost which i think

19:43Ian Shepherd:creators really respect and appreciate i mean it's uh it's an amazing strategy particularly for a software business to have built this really really impressive i'm curious what about ai how do you use ai as a business when it comes to content production well we're really intentional around it not being a replacement for creativity it's an augmenter of creativity and so usually there is usually human taste and a human in the loop from the conception of an idea to the publish and i think where ai really plays a huge role is everything in between it's kind of like the the production and post-production aspect of content creation and so on the video front for example it's helping us gut test topical ideas title ideas it's helping with scripting with outlining it's helping with research and then what we've actually built out is a way where now ai is helping us automate the atomization of long-form video into a bunch of clips made specifically for the nuances of different platforms and so a video a long form video gets processed using clod and the transcripts are generated and then we've trained it up in a way where it can predictively but it's getting better right predictively identify like what are the different time codes within a transcript that it believes based on historical data has the highest propensity to go viral on a certain platform it then feeds that to a video editor and we use um you know premiere but we also use um like natural language editors like descript for example where it's easy for um a prosumer or like a novice video editor or like a channel manager to go in there and just like make text updates and like see it reflected on the screens descript descript then generates the clips and then exports it packages it up for you as well and then all really channel manager has to do is like just you know give it like a human layer of editing right like is the hook good is the copy for the caption and you know like this from like the title good like should these certain parts be clipped out and then they can press publish and so something that used to be such a manual process is now fairly automated but it's still at the end of the day really requires human taste uh and intuition to make sure that like it's not just good it's great and so um we use it there as well um you know in a world where a lot of our text-based content especially on the blog is shifting from co to aeo it allows us to automate um a lot of just like the research and some of the sort of like the like the harder writing that goes into blog post creation the creator front for example you've built up a pretty great agent that that allows us to use historical data on what creator partnerships have worked best to predictively recommend what other creators should we be working with across youtube newsletters etc that maybe we aren't thinking about really to help us continue to expand our bench and reach potentially new audiences that haven't heard of HubSpot.

22:43Ian Shepherd:That's great. Really impressive. And how big is the team there working at HubSpot Media? So we're 60 folks that spread across content, monetization, and audience development. Content is probably the bulk of our folks. And those are oftentimes, you know, video producers, your editors, human writers, people that are working on graphics, podcasts, etc. We have a monetization team that's significantly smaller, but it's really focused on creating all the lead magnets and the conversion rate optimization and the ad trafficking that goes into all the inventory that is being generated in a given month.

23:21And then the audience development team, which is effectively a marketing team within media, that's really focused on organic partnerships, paid media acquisition for newsletter growth. How can we improve the operations of the entire media function as a whole? how can we better use ai to improve content output and quality i'm in general just like systems and then the creator program sits within there as well so you know relative to other media teams probably on the smaller side but for something that's relatively novel within a software business like it's like a pretty good sized team uh and we work with a ton of contractors as well i would say using ai has definitely allowed us to be able to just like maintain general capital costs and headcount costs while being able to scale as well.

24:06For sure.

24:06Ian Shepherd:And what does the future look like for HubSpot Media in one or three years? Can you give us like a sense of anything coming down the pipe? We have a number of new video franchises launching that are allowing us to really reach different segments of audiences that maybe historically underinvested in from an unoperated perspective, but are really important to our business so you know how can we reach more corporate level decision makers for example huge tam opportunity something that we already do a pretty good job at doing i mean like reaching but could be doing a lot better we're going to continue to invest in content that reaches marketers and ai practitioners and business builders we're also just going to continue to improve how we automate output like like how can we turn a single investment into multiple different outputs that allow us to just again stay top of mind across as many platforms as possible as consistently as possible throughout the entire year so that you know once it comes time to make a decision on your next crm or point solution we're part of that day one list and we can hopefully convert folks into customers it's wonderful well jonathan it's been really great to speak today before we wrap up i just wondered if you had any words of advice for creators listening based on your experience working with them at HubSpot?

25:23I think the biggest one is diversification is incredibly important. Like I know, especially as someone that probably is just working for themselves and is a one person shop, it's hard to try to boil the ocean. And that's not what I'm trying to say. It's more that if you can find a way to turn a single channel into multiple channel plays, that's probably going to really help you long term. like we've seen so many, at least in our experience working with creators, examples of creators that have just gone all in audio-only podcasts. And as a result, I've had a hard time navigating a shift where Spotify, YouTube, etc.

26:02are obviously investing even more in podcasts, but video-first podcasts, and have not been able to make that jump. So the more that you can diversify and really try to multiply your output and your editorial into as many platforms and places as possible, I think the easier it will be to just be sustainable, but also future-proof your business in a world where algorithms change overnight and you need to play on the defense.

26:25Ian Shepherd:Very wise words there. Well, thank you, Jonathan. It's been really great to speak today. Congrats on all the success for HubSpot and look forward to following the journey. Yeah, thanks, Ian.

From the publisher

HubSpot has built a media company inside its software business — powered by creators, YouTube, newsletters and AI, and reaching 50 million people every month.

In this episode of The Business of Creators, Ian Shepherd speaks with Jonathan Hunt from HubSpot Media about the strategy behind that growth, how HubSpot evaluates creator businesses for acquisition, and why video, diversification and AI are becoming increasingly important for creators.

Topics Discussed:
- How HubSpot built a media network spanning 17 YouTube channels, newsletters, podcasts and websites
- The strategy behind acquisitions including The Hustle, Starter Story, Mindstream and Futurepedia
- What HubSpot looks for when evaluating creators and media businesses
- Why HubSpot is investing heavily in video and YouTube
- How AI is being used to scale content production and distribution

Key Takeaways:
- How HubSpot decides whether to build a media brand from scratch or acquire an established creator business
- What makes a creator business attractive to a potential acquirer, from audience scale and ROI to diversification and trust
- Why relying on a single platform can create significant risk for creators — and how to build a more resilient business
- How one long-form video can be turned into content across YouTube, social, newsletters, audio and other platforms
- How HubSpot uses AI to research ideas, test titles, repurpose content and identify potential creator partnerships while keeping human creativity and taste at the centre

Listen to learn actionable strategies to grow your creator business — and don't forget to subscribe to the channel for more insights on the business of creators!

Timestamps 

  • 0:00 — Introduction: HubSpot Media and Jonathan Hunt
  • 1:07 — What HubSpot Media is and how it reaches audiences
  • 2:15 — Why HubSpot began investing in owned media brands
  • 3:24 — Jonathan’s background at Vox, National Geographic, and Complex
  • 6:12 — The build-versus-buy approach to media acquisitions
  • 7:28 — HubSpot’s AI media acquisitions and strategy
  • 8:35 — How HubSpot evaluates creator businesses
  • 10:52 — Working with creators after an acquisition without changing their voice
  • 13:48 — Creator-business valuations and the TBPN acquisition
  • 14:59 — Why video is HubSpot’s priority format
  • 17:25 — How HubSpot’s creator program works
  • 20:13 — How the team uses AI in content production
  • 22:43 — The size and structure of HubSpot Media
  • 24:06 — What’s next for HubSpot Media
  • 25:13 — Advice for creators: diversify across platforms

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