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Index/Finance/Raising the Brand
Raising the Brand artwork

Raising the Brand with Ben Winn, VP Community & Content at FirstMark

Raising the Brand · 2026-06-30 · 30 min

0:00--:--

Key moments - from our scoring

Substance score

64 / 100

Five dimensions, 20 points each

Insight Density13 / 20
Originality12 / 20
Guest Caliber15 / 20
Specificity & Evidence11 / 20
Conversational Craft13 / 20

Ben Winn has spent a decade building communities that outlast typical launch strategies, starting with CS&FOCUS, Canada's largest customer success community, then scaling community-led growth at Catalyst Software (tripling ARR three years running), and now leading community and content at FirstMark - the VC firm behind Pinterest, Shopify, Discord, Vercel, and Clickhouse. His core thesis is simple but counterintuitive: the most sustainable communities and brands succeed by centering others' success, not your own. At FirstMark, this manifests in Guilds, an invite-only community of C-suite executives from OpenAI, Anthropic, AWS, DoorDash, Instacart, and Figma. Because these leaders face constant noise and asks, Winn manually moderates every message, keeps members off Slack (using email instead), and obsesses over curation to maintain signal. On the content side, Winn argues that commodity knowledge - SEO-driven thought leadership, generic blogs - is obsolete in the age of LLMs. Only proprietary data (from surveying your community) and entertaining/spicy content deserve investment. He's also launching Terminally IRL, a newsletter pushing back against the "terminally online" ethos, arguing that alpha information requires in-person relationships, not Twitter scrolling. For B2B operators in alternative assets, PE, and credit, Winn's playbook centers on testing hypotheses with small, trusted groups before scaling - a discipline that translates even into heavily regulated environments.

Key takeaways

  • →Community isn't a platform - it's the entry point to relationships; revenue conversations come only after proving value and earning social capital through helping members succeed.
  • →Guilds succeeds because Winn manually moderates every message and removes all friction (no logins, curated rooms, frictionless experiences), making executives trust that only high-signal content reaches their inbox.
  • →Content strategy should focus on two buckets: proprietary data competitors and LLMs don't have (surveys, internal research) and entertaining/spicy original content; generic SEO-driven thought leadership is now commoditized and useless.
  • →Test community and brand hypotheses in small, ring-fenced groups (10-50 people) with trusted validators before public launch to prove viability and de-risk at scale.
  • →In-person relationships yield alpha that online channels cannot - dinners, events, and real-world curation matter more than being terminally online or posting on Twitter and LinkedIn.

Guests

Ben Winn

Topics in this episode

Community-led growthproprietary dataFirstMarkGuilds (executive community)CS&FOCUSCatalyst SoftwareLLM-proof contentTerminally IRLhigh-signal curationcustomer success communities

Questions this episode answers

How do you connect community building efforts to actual revenue growth?

Community is the entry point to relationships, not a direct sales funnel; you earn the right to discuss fit through trust and value. Winn tripled Catalyst's ARR three years running by uncovering insights through community relationships, then having organic conversations about whether a commercial relationship made sense - never leading with a pitch.

Why does Ben Winn manually moderate every message in Guilds if he has other things to do?

Because Guilds serves 550 of the world's best CFOs and other C-suite executives who are inundated with noise; one self-serving pitch or unvetted message will trigger unsubscribes and destroy trust. Manual moderation is the only way to guarantee every message adds value.

What content strategy works now that LLMs have commoditized most online knowledge?

Focus on proprietary data (survey findings, internal research, customer insights that LLMs don't have) and entertaining original content; generic SEO-driven thought leadership is obsolete because LLMs serve up the same thing instantly.

How should private equity or credit firms test community and brand ideas given compliance constraints?

Ring-fence small tests with 10-50 trusted validators (advisors, GPs, LPs) to prove the hypothesis works before scaling publicly; low-risk pilots on specific segments validate the idea and build buy-in without regulatory exposure.

Why launch Terminally IRL in an age of AI and digital everything?

Because online information is commoditized and accessible to everyone; alpha and real insight come from in-person relationships (dinners, curated events, real conversations) that emails, tweets, and LinkedIn cannot replicate.

What our scoring noted

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

Insight Density

13 / 20

The episode delivers consistent, actionable frameworks around community building and content strategy that practitioners could implement. Ben articulates the 'success of others' principle, the community-to-revenue funnel, and the distinction between proprietary data and entertainment content clearly. However, much of the advice gravitates toward generalities (e.g., 'build trust,' 'provide value') and the specifics about *how* to execute at scale are limited - the transcript often stops at high-level strategy rather than mechanics.

success through generating the success of others is sort of the core theme that translates across all of these things
community is sort of the entry point to the conversation...from there, it's now about finding the right time and the right way and the right method to bring revenue into the conversation

Originality

12 / 20

Ben's 'do something different, even if it's worse' framing is refreshing and contrarian. The insight about in-person experiences becoming *more* valuable (not less) as online content commoditizes is genuinely counterintuitive for 2024. However, the core thesis - that communities should focus on member success rather than transactional conversion - is well-established in community-building literature. The proprietary data / entertainment content split for content strategy is sensible but not novel.

do something different, even if it's worse
if you want the alpha, you have to be in person with someone

Guest Caliber

15 / 20

Ben is a legitimate practitioner with a decade in community building across three different operating models (customer success, SaaS, venture capital). He has shipped at meaningful scale - tripling ARR at Catalyst, running high-signal communities for C-suite execs at FirstMark. He's not a consultant or theorist; he has operational skin in the game. However, his domain is somewhat narrow (community/brand/content), and he has not been a founder, operator of a venture fund, or P&L owner in traditional business roles, which limits scope relative to the show's target audience of brand builders in PE/credit.

customer success...where community led growth helped triple ARR three years running
the people in that community are C suite at the biggest and most interesting companies in the world. Right. OpenAI Anthropic, AWS, DoorDash, Instacart, Figma

Specificity & Evidence

11 / 20

Ben names specific companies (OpenAI, Anthropic, Figma, DoorDash, Instacart, Shopify, Discord, Liquid Death) and references concrete tactics (email-based forums instead of Slack, manual message moderation of 550 CFOs, a three-per-week event quota). However, he rarely provides numbers, metrics, or timelines beyond the vague 'three years running' reference. Claims about community impact on ARR or brand lift are asserted but not quantified. The 'happy hour' critique is stated strongly but without data on effectiveness deltas.

I personally moderate every message in every group...in a group of 550 of the best CFOs in the world
I have a quota for myself of, you know, three things a week. That thing could be a dinner, that could be a happy hour, that could be a, uh, one on one with someone

Conversational Craft

13 / 20

Jonathan asks good setup questions and creates space for Ben to elaborate. He follows up on the Guilds community specifically and pivots cleanly between topics (community → content → personal brand). However, Jonathan rarely pushes back on claims, doesn't challenge Ben's strong opinions (e.g., the happy hour rant), and doesn't probe for contradictions or limitations. The conversation is warm and collaborative but lacks the tension or interrogation that would test Ben's ideas or surface disagreement.

Could you give us some other specifics of how you built something that people actively wanted to be engaged with?
I would love to talk about that for a little bit. Can you describe for us what content marketing is at firstmark?

Conversation analysis

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

Share of words spoken

  • Speaker A82%
  • Speaker B18%

Most-used words

community45brand29building19events19world18content15marketing14first13success11different11online11love11communities10best10terminally9successful9

Episode notes

Welcome to Private Equity Marketeer’s Raising the Brand , where we delve into the stories and strategies behind the leading brand builders & capital raisers in private markets. Today, we’re joined by Ben Winn. Ben is VP Communities & Content at FirstMark, where he works to create and scale impact for founders and the broader venture community through various communities, like Guilds by FirstMark (FirstMark's private network of 3,000+ C-Level executives representing over 80% of the global unicorn ecosystem), building bespoke networks, creating impactful content and events, and building and managing partnerships to further accelerate FirstMark and its portfolio companies. Previously, Ben was Head of Brand & Community Marketing at Catalyst Software (acquired by Totango), led Customer Success at SeamlessMD, and was Founder of CS in Focus, a global community for Customer Success professionals with over 3,000 members.

Full transcript

30 min

Transcribed and scored by The B2B Podcast Index.

Speaker A: Jonathan.

Speaker B: I'm Jonathan Blank, former head of marketing at Citadel and Carlisle. This is Raising the Brand by Private Equity Marketeer. We explore the stories and strategies behind the leading brand builders and capital raisers in private markets. And today we're sitting down with Ben Nguyen, VP of Community and Content at FirstMark, the New York venture firm behind Pinterest, Shopify, Discord, Vercel and Clickhouse. Ben has spent a, uh, decade building communities. He founded CS&FOCUS, which is Canada's largest customer success. Community was the first marketing hire at Catalyst Software, where community led growth helped triple ARR three years running, and now runs community and content at FirstMark. A decade, for the record, is roughly nine years longer than the average community strategy survives after its launch deck, which makes Ben one of the few people who's actually earned the word. He's also just launched Terminally irl, a newsletter on the craft behind great real world experiences. Welcome, Ben.

Speaker A: Thanks for having me, Jonathan. Thrilled to be here.

Speaker B: I know our audience, uh, really wants to hear from you on a number of different areas. We'll start with what you've really distilled from running community in three pretty different worlds of customer success, SaaS and now venture capital. What are the themes that carries across all of them?

Speaker A: Uh, I think the biggest thing I'm lucky to have started my career in customer success because I think that's ultimately the key to not just community building, but pretty much anything you do in business and in life is like the things that work best are the things that lead to other people's success, not your own being the primary function. So I think success through generating the success of others is sort of the core theme that translates across all of these things. So CS and Focus was around, hey, like, customer success is a new function, not, you know, the playbooks haven't quite been written yet. It's, this is like early SaaS. So let's just bring the people together that are doing it and building it and help each other win. Let's share intel, let's share playbooks, let's share career opportunities and let's grow. And that's hadn't existed before. And so, um, you know, while the community was cool and the events were fun and whatever the real success of it came down to, you know, this attacked a gap in the market, addressed a challenge and created success for the members of that community. And then they're just going to organically keep coming back and referring people in and like, that's how these things get a life of their own. You translate that to Catalyst, you know, as a, AN uh, enterprise SaaS platform. But again, like companies only work if people are getting value from the product or the service. And so community led growth there was again around like, how do we build? How do we help our buyers, our customers, our prospects, or even just people that are in adjacent roles? How do we help them be more successful? Because if we can do that, then the company's going to grow, the brand's going to grow, the affinity is going to grow and then again straight through to venture capital. It's the same thing here. We want our LPs, uh, to be successful, we want our founders to be successful. And if those happen, then we are successful. And so it's about putting that goal front and center. How can I make others successful? Because if I do that, then I will be successful. And that's sort of the biggest theme that carries through across all of it.

Speaker B: That's really helpful. One of the things I'm taking away from that is your efforts seem to be very much person centered. Um, is that accurate? Person centered, human centered.

Speaker A: It's all about people. I think even, you know, people tend to, I think it's actually a common misconception that, you know, a community needs to be a group of X number of people that get together or in a slack group or whatever. If you have a brand, even if you're a consumer company, like you have a community, it's your user base, it's the people that are the end users of your product. So you still need to build that community and nurture that community. So it's about people. And you know, whether you're thinking about it from a one to one intimate perspective or a one to many, like you're building a global brand perspective, it does all come back to people. And people pretty much out of life just want, you know, to be happy and successful. And so if you can help them do one or both of those things with your efforts, then your job is pretty much done. It's all downstream from there. Great.

Speaker B: So we've talked a little bit about enabling the success of your buyers, of your users at Catalyst, where you were the first marketing hire, you helped triple ARR three years in a row for this audience of brand builders and capital raisers. What would you tell them about how they can draw a line from community efforts to revenue?

Speaker A: It's a really good question because this is always the tricky part, right? There's, there's a school of thought where it's kind of like, let's take it on Faith, trust me, like, we're going to do these things and they might pay off in the future, you know, And I don't think that's quite right, but I think the big mistake people do is they get overly transactional too early. And that's not how you build a community either. By throwing an event and then emailing everyone that came to try and get them to, you know, sign up for a demo or whatever it is you're building. Um, the reality lies somewhere in the middle. Community is sort of the entry point to the conversation. It's the. I like to think of it as someone entering your world, coming into your ecosystem, where there's a relationship either with you personally or someone on your team or with your brand. Um, community is the entry point to that. From there, it's now about, you know, finding the right time and the right way and the right method to bring revenue into the conversation. Um, you know, by someone being in your community, they're engaging with you at events, in person, online, whatever. But that gives you now the platform to uncover, like, are they the right fit for us? Are we the right fit for them? Is this a true, like, win, win, if we do business here, um, and why, or why not? And then as the relationship develops, you have these organic opportunities to feel out, like, hey, we're, you know, someone from your team, expressed interest in whatever. Can I be helpful? Is there someone you want to speak to? Or just candidly, hey, huh, you know, we're expanding into this area, or we've had a lot of customers in your segment find success with, like, this solution. We'd love your feedback on it. Like, if you don't care or you don't find it compelling, that's super helpful information to us. So I'd really appreciate, like, even if you have no intention to buy, can you give me your feedback? Because if you say, I don't want to buy it because you're missing these features or, um, because I think this other product's better, or my cousin is the founder of this company. That's all super helpful intel. And so everything starts with relationships. The relationships give you the insight, and then the insight gives you the direction on whether you should lean in, pull away, you know, what kind of sales relationship is this going to be? Um, and it's again, the same across most of these spaces in terms of, you know, community is the entry point. You start building value. Hopefully you provide some value upfront, and then the social capital you earn by providing value to people in your community earns you Then the right to at least have the conversation, uh, about why something may or may not be a fit, why a commercial relationship may or may not be the right, the right thing in the cards.

Speaker B: Great. We'd love to talk about one of the specific communities that you're building. Uh, so Guilds is an invite only community that you run and it spans most of the unicorn ecosystem. Could you give us some other specifics of how you built something that people actively wanted to be engaged with? And are there any lessons about how, uh, about any lessons of what could ruin communities?

Speaker A: 100%, uh, guilds are really interesting and it's, and it's the highest stakes community I've ever built. Reason being the people in that community are C suite at the biggest and most interesting companies in the world. Right. OpenAI Anthropic, AWS, DoorDash, Instacart, Figma, like, and you know, when you get to executives at that level, they are already inundated with everything like pitches and asks and actual work and board meetings and you know, paid communities that they're in and unpaid communities that they're in and events that they're speaking at and going to. And there's so much noise and there's so much, uh, going on in their world that um, they're just looking for any reason to disengage. And so you don't have a lot of leeway. If one bad email comes from you to their inbox, they're probably never gonna respond to you again. If you invite them to one bad event, they're probably never going to come back. Um, it's very much a high stakes relationship and that's great in some ways and very challenging, you know, in others. For the reasons I enumerated, the reasons I love that is because it forces us to be really on top of our game with everything we do. So that means, you know, going through, you know, really debating is this the right topic at the right time for the right audience? Who's going to be in this room or this dinner that we're doing? Is this the right group for the right conversation? Because the reason it's great is these, uh, executives deal with so much crap and get, they end up having to go to so many bad events and bad experiences that when you prove to them that no, we know what you want, we understand you, we can curate the room you want to be in, we can sit you next to the people you actually want to sit with and we are going to remove all the friction so you don't have to think about anything. You earn that reputation as a host, which keeps them engaged and coming back and then they actually lean in more and they reflect, refer people in their network. Because we've shown that we are high, signal that we are curated, we are thoughtful, we are doing all the work for you so that your experience is frictionless and all upside. And so it's high stakes, very challenging, but also very rewarding from that perspective.

Speaker B: Right, so the attention to all the details seems to be the importance of those details magnified, uh, by 10, 20, 30 in this world.

Speaker A: Yeah, absolutely. Uh, it's every little detail thought through and that's, that's the fun part, that's the challenge we run, we have forums for each of these groups that are all via email chains so that they don't have to log in anywhere. I hate slack groups for communities and I personally moderate every message in every group. I approve or deny it and I do that. It's not fun. I have other things to do but like by doing that, it's the only way I can make sure that in a group of 550 of the best CFOs in the world that no crap is hitting their inbox. No one that's sending a self serving message or pitching them on something or asking for a favor that only benefits them, um, like once that goes, they hit on subscribe and I'll never hear from them again. And so you know, it's, it's friction for me but it allows me to be confident that every message that's going out to this listserv is a high quality message that is not going to get to the unsubscribe button.

Speaker B: Yeah, I love that. And it struck me when we talked a, uh, week ago when you, you know, you were so passionate and still are so passionate about the fact that they don't even have to log in. I think that little detail um, really makes a difference and I'm glad you brought it up here. Uh, for, for everyone that's watching. I'd love to pivot a little bit from, from community building and SaaS and in venture capital to private equity, private credit, some, some of the bigger alternative asset managers in the world and how it differs. You know, your world at firstmark runs on somewhat of a different operating system than some of the folks watching. You can move fast, you can build in public and you can let community build, uh, be the engine. You know, a big P or credit shop can be somewhat of a different animal compliance on every word the brand machine is pointed at. Institutions and increasingly the wealth channel at scale. So could you help us translate? If you woke up tomorrow running marketing at one of those firms, like the firm I ran, marketing at Carlisle, what would you fight to keep from your playbook, and what might you have to give up?

Speaker A: Yeah, this is. This is a tough one. I, uh, mean, the first thing I would do from the playbook is sort of figure out, like, what do I have to work with, right? Like, what's my leeway? Do I have a team? Do I have a budget? Is it just me? You know, what's the tar? What's sort of our goal with building this community? Is it like, all, you know, fund managers, or is it with, like, a certain subset of family offices in a certain area? So, you know, the broader lesson that I would impart is no matter what kind of community you're building or brand you're building, you have to think of it like an actual product, meaning there needs to be a gap in the market or an opportunity or addressing that others aren't. So that you can then come up with a hypothesis about what might resound and fill that gap or take advantage of that opportunity, then test that hypothesis with a small group, and then expand it out in concentric circles. That's sort of my playbook in a nutshell for running and building communities and brands over the years. I think, you know, there's also. I think it's Toby Luca, uh, at Shopify, which is another first mark company, who said, do something different, even if it's worse. And I love that because so many people will see something do well, and they're like, oh, we want to do our version of that, right? We said that this was years ago, but, like, the Ice Bucket Challenge for ALS was huge. And then every brand and every company in the world was like, well, we need to figure out our own version of the Ice Bucket Challenge. It's like, no, that's been done. Same with, like, tvpn, right? Took over tech by storm, and it's this great media company, and then everyone tried to, like, launch their own versions of a tvpn. It's like, it's been done, done. Do something different, even if it's worse. So, uh, you know, I think that's where I would start is figuring out, like, what is my goal here? What is my objective? What do I have to work with now? Knowing, you know, my target audience, let's say my icp, where are they spending their time? What are they doing? What are they thinking about? Most importantly, what's keeping them up at night, what's unsolved for them, right? That's where the really juicy stuff is and that's the stuff that will engage them. Once I've sort of determined, okay, there's this opportunity where right now they're all figuring out like there's a terrible example like how to get an allocation in anthropic, right pre ipo, like everyone's, you know, in those. So, okay, what can I figure out or what can I do in order to address that challenge to engage them? And I'd come up with like a whole bunch of list of ideas. Ideally I'd be working with several people on that and then I'd, you know, uh, fight to bring that to life probably through validating it through some trusted people who hold sway. So my version of that first mark is founders. If I have three founders external, the first mark say, this is a great idea idea, I would show up to this event or I want to listen to this conversation, I can bring that to our GPS and that's all the validation I need. Rather than me just saying, I think this is a good idea. So I, I would try to do that and then I'd go from there. I think the, you know, fortunately and unfortunately I've never worked in pe, so, you know, I don't know the, the things I don't know in terms of red tape and where I might get blocked on this journey, but at least conceptually that's where I'd start, is let's figure out a small controlled way to test a hypothesis in a ring fenced way so that uh, the risk is low. If we run an event idea with 10 people that represent the ICP, that's all off the record. It's low risk, there's no exposure. Um, but it gives me enough to then prove to do the 50 person event and then the 100 person and the thousand person. And so you, you ring fence and you grow in concentric circles as you sort of validate your hypothesis, get smarter about it, incorporate learnings so that by the time you're doing a public launch of a community or a brand, you validated it with most of the people that matter. The risk is now low. Everyone's bought in and feels good about it.

Speaker B: Yeah, that's great. I uh, remember when I was at Carlisle, we would often get from senior leadership, I would often get emails saying, oh, we see one of our competitors doing X and content marketing, brand marketing, we need to do something similar. You put it more eloquently than I did of uh, that this, this program needs to be managed like a product. And so what we did was we had a formal advisory board of, of LPs to run past these programs and get validated first. So. Yeah, totally.

Speaker A: And, and it's, it's the uh, do something different even if it's worse and then validate with a trusted group. So I think, yeah, having an advisory board, uh, whether it's an official advisory board or even. I've seen people form advisory boards purely for the, for the uh, purpose of this. Right. Like we want to build a community around X. Will you be on this thing? We're going to meet once a quarter and talk through A, B and C. Most people are pretty happy to do that kind of thing, especially when you have a brand like Carlyle Group to, to be. To be doing it Great.

Speaker B: Well, so we've talked about community. You have another whole other part of your title, uh, which is content. I would love to talk about that for a little bit. Can you describe for us what content marketing is at firstmark? I know, you know, for a lot of firms content can be everything from a newsletter they have to a blog to press releases. Um, how do you think about content marketing at firstmark?

Speaker A: Uh, well, similarly to communities, right, like uh, the things you listed, a newsletter, a blog, you know, website, a TikTok, whatever it is, you know, these are the equivalent of a list server, a Slack group or whatever in the community world where these are outlets or these are tools, these aren't the thing themselves. Right? So, so it's, you know, the, those things will change and over time as channels become better and worse, as algorithms change, as audiences change. So whatever your strategy for content and community needs to be something that transcends whatever the platform is that it's on. On the content side, what's gotten really interesting is that, you know, content running marketing for a decade now, so I've seen it change a lot. Right? And what matters today is very different than what mattered before because now most knowledge has been commoditized and you can find everything online and LLMs will serve up pretty much anything you want. So doing the kinds of you know, uh, going from uh, years ago doing uh, you know, thought leadership articles specifically for SEO and driving for backlinks and trying to get our ranking up and like all these things are, are now, you know, is no longer the motion. The only content I'm really interested in nowadays is there's two buckets. One is based on proprietary data because that's something that the LLMs don't have, your competitors don't have. So what proprietary data or proprietary opinions do you have access to that can come from surveying your community or your customers or internal thought leadership, whatever it is. You, uh, know, what do you, what information do you have that an LLM doesn't? Because you can turn that into a big strict. That's information that no one else is publishing. The, um, LLMs will actually reference it if you, you know, do the proper aeo and people will come to it. Like, it still works in terms of engaging your community, bringing people in. The second bucket is, I'll call it like funny slash spicy. It's entertaining content because LLMs are anything but entertaining. It's how you use them. Uh, that can be. But you know, again, going even back to my, My original thing before is like everything is downstream of people wanting to be successful and happy. And so if you can do one or both of those things with your communities and with your content, you're golden. So, you know, uh, yeah, Catalyst, we put out, we were, we were early to the meme game in, in B2B and so we were doing memes about, you know, being in tech every day for years. And that had a massive impact on our growth because it was just this repetitive drama every day of like, it was stupid stuff. Stuff that's like, funny. I could never do it at first, Mark, because we're, you know, this was at a SAS company, right. And so now, you know, we have to. The brand is different. So that wouldn't be on brand for us now. But you know, one of our partners, Matt Turk, great follow on Twitter, absolutely hilarious. And that works really well for him. And he'll do a mix of insightful posts and then comedy posts. Um, and both work and both engage the audience and both are original. So at a high level, that's the sort of the two buckets that I care most about. And then it's from there it's more an operational thing of how do I translate these into the proper mediums and formats for all the different platforms that I want to use for distribution?

Speaker B: Great. So you've also just launched Terminally irl, the strategies, craft and mechanics behind exceptional real world experiences. Why in the age of AI and digitizing everything, uh, did you, did you launch this and why now? And tell us a little more about this project.

Speaker A: Well, originally it started as just I wanted to document a bunch of my approaches to things like Playbooks and things like that. The way I, the way I do things have gotten pretty specific Pretty practiced. And so I just wanted to start documenting those myself and do more writing because I find it helps me think and sort of hone what I'm doing it, what I'm doing and why I'm doing it. Um, but really the terminally IRL thing came around because I was getting really frustrated because I was seeing all of these job descriptions being posted and you know, posts on Twitter and LinkedIn about being terminally online. We want people that are terminally online. You have to be terminally online. It's all about being terminally online. And I hate that because A, you know, I hate being online. I unplug whenever I can. But um, B, I just think it's the wrong strategy. The online is commoditized. You can, anyone can find the information that's on, that's on Twitter. Anyone can find the information that's on LinkedIn. If you want the alpha, you have to be in person with someone. Imagine like the intel you get when you have dinner with, with a customer or a prospect and what they tell you and what they don't tell you versus over email, let alone over Twitter or LinkedIn. Like the, the terminally online stuff helps to sort of know what's going on in the world. But you can get that in five minutes of, of quick scrolling or you can get an, you know, you can get coworker or whatever you're building on to send you that roundup every day of what's happening. I think people need to be way more in person. I think the world is going towards an in person future because even now people don't trust online content. So much of it is now AI. More of the Internet is now bots than humans. That happened about two weeks ago. So as online becomes more and more fake and more centered around algorithms that, you know, cause anxiety and give you disillusionment because you think people are so far ahead because they're posting on X about, you know, this college kid making 50 grand a month doing this one thing with AI. You know, like you see those kind of of posts all the time and no one feels good about it, but everyone feels good when you have a great in person experience. So from a forward looking point of view, I just think in person is going to get more and more important. I think that's where the edge is, that's where the insights are, that's where the relationships are, um, and that's where the world is going. So if that's true, then it's about how do we do in person right There's a lot of ways to do it wrong. Events, in my opinion, follow a power law as like Venture does. So in Venture, the power law means you'll back 20 companies, 18 will fail. And the two that do well will far make up for the ones that that uh, that didn't. And so the two that win will far make up for the ones that failed. And events are the same. You have to go to four shitty ones to go to the one that was worth it. But man, is that one worth it. And you're like, all right, this is why I go to these things. And so, so with terminally irl, what I'm trying to do is help people put on better events of all shapes and sizes. More and more people are entering the space. More and more companies are hiring heads of events, heads of strategy, heads of community. And so, you know, I want to have a place where I can just have some resources and be sharing that with people, sharing what I'm learning, what I'm building as I'm doing it all with the purpose of helping people create higher signal events that everyone enjoys going to. Like, it's again like going back to that win, win, win thing. I want to go to better events selfishly, like for, for, if not for myself, like, if not for anyone else selfishly, I want to be invited to amazing events all the time and I want to go to amazing events all the time. And so I want to keep getting better at my job. I want to help other people keep doing better and better events. Um, and I think that's where the world is going. So that was sort of the impetus behind it. And now it's something I update about once a week with a new playbook or a new template or something like that. That's all shaped around crafting in person experiences that get the job done.

Speaker B: When I was at Carlisle, events rolled up to me. I had the most amazing, uh, events professionals under me. I'm now starting to think does what were our events in the, in the power law to? I'll have to reflect on that a little bit more.

Speaker A: Well, it's funny you go to Forbet. Like I have a quota for myself, like, because I consider my job primarily first and foremost network like networks. And I have to know people. And so I have a quota for myself of, you know, three things a week. That thing could be a dinner, that could be a happy hour, that could be a, uh, one on one with someone. And if I don't have three, I find the third. And if I've Five. Then I at least try to cut one or two so that I don't end up divorced, uh, before long. So, you know, balancing home time and work time. But I do hold myself to that quota and it helps a lot of the time because I'll go to a mix of events and see what people are doing or not doing. I'll steal the things that are amazing and I'll pass those along and I'll note the things that are terrible. And I will, in an abstract way, without naming names, ask people to avoid doing that in the future.

Speaker B: I want to talk a little bit more about this, about, you know, about what you've done to be part of the, the marketing community. For each of the firms that you've been at, it is very clear that your personal brand has been an asset for that firm. How should aspiring brand builders that are watching, how should they think about investing in their personal brand, uh, versus their companies or alongside their companies best?

Speaker A: So I know I'm a broken record. Help other people win is. Is the best brand that you can possibly build and the best thing you can possibly do. I don't think it makes sense to try and start a whole other brand and do a whole intentional. I'm going to post on LinkedIn and I'm this and I'm going to do all the things that maybe Twitter or whatever might tell you to do. Brands are built the best brands that last are built slowly and thoughtfully over time. Um, the best way to build your personal brand is by being known as someone who is helpful and who gets things done. And so most of my brand, like that's at, uh, the foundation of it is I spend a lot of my time not on things that are, you know, necessarily directly valuable to myself or to First Mark. They're helpful to other people. But by doing that, I'm building up credibility and building the brand. I'm building social capital and I genuinely enjoy doing that. And so that's sort of at the core of my brand. And then, you know, the, the thing with that is that'll get you well known, well liked, you know, to a certain extent. But then the brand is the, is the flavor that's uniquely you that you put on top of that. So for me, uh, I have chronic middle child syndrome. Uh, so I need to be the center of attention. Uh, I host a lot of events, I emcee a lot of events. My goal is within the first minute every time I get on any stage anywhere, is to make the audience laugh. If I can do that within the first minute. I've now set the tone for the rest of the event and for the evening. And people are like, oh, I like that guy. He made me laugh. And so if I can do that every single time, uh, you know, I'm hosting an event or I'm on stage. Over time, you start building that into, into your own personal brand. You bring your own flavor to whatever it is you're doing. So foundation is just being known as someone that's helpful and that gets things done and done well. And then add your own personal flair on top, whatever it might be, whatever your quirk is, whatever your interest is, whatever your, you gravitate to personally, however that comes to life, is sort of that layer that adds on top that will supercharge the work that you did on that foundation.

Speaker B: Your flair is something I aspire to. My, my hobby is improv comedy.

Speaker A: To the Comedy Store and uh, uh, we'll head to a comedy shop.

Speaker B: I'm going to take you up on that. So why don't we conclude, uh, uh, with a lightning round if you're up for it. Just a couple of final questions.

Speaker A: Great.

Speaker B: What is a community that you think is best in the world you cannot answer with your own, with the communities that you've built?

Speaker A: Uh, no. I'm deeply critical of myself first and foremost and everything I've done. So, you know, I'm going to, I'm going to do a cheesy cop out here. And I will say the New York tech community. I have now spent time in sf in Toronto, in New York. There's something special about the New York tech community in that I think we've got the power of the Bay Area with the familial vibe of Toronto, where I'm from. And so New York is this sort of like magical tech hub where even though people are competitive, they're very helpful. Like, it's a small community. We're all so squished together. And so, you know, there's competition here, but it's like fun competition. Everyone still helps each other. Everyone loves to find areas to collaborate and find those win, win, wins. There's so much energy behind it. It's also cross functional. So instead of sf, where everyone is in tech, here you've got consumer, you've got enterprise, you've got banking, you've got a million different industries, you have hospitality. It's all the best in the world of all of these industries kind of coming together. So you have a lot more diversity. But I think just the ethos of like New York, where it's helping each other. We're all in this together. Yes, it smells horrible, but we love it. Like, that whole vibe I think generates, I think, the best community, uh, to be a part of.

Speaker B: Awesome. Uh, question two. So we've, we've had a lot of new acronyms the last couple of years, whether that's LLMs, now MCP, all of this. What's one word or phrase in community or content marketing that you think we just need to retire?

Speaker A: Happy hour. I hate happy hours. I have an article about it. Please stop doing them. They are 99.9% of the time the wrong thing to be doing for your goals. And I will die on that hill. I know people will say strong opinions, loosely held. That is a strongly held, strong opinion. And I will happily come back on the show and debate someone if they disagree. But that is, I would strike happy hour from existence for community. I love attending them myself. Uh, just happy hours in general. I can always go for a cheap martini, but. But not. Not as a community building function.

Speaker B: Awesome. Well, we're definitely putting that article in the show notes. I can't wait to read it all. Ah, right, final question. Uh, what's your favorite brand outside of finance and why?

Speaker A: I love Liquid Death. I think they are. Ah, they're marketing water. It's water in a can. Like, I'm just still sort of gobsmacked that they've built this massively successful company based on water. And it's just this insight of like. Well, I think it started as like, the, um, musicians on stage didn't want to be seen drinking water bottles, but they didn't want to drink alcohol. So they were like, well, what if we design a can that looks like, you know, alcohol but is actually water? And then they just turn that into this massive company and they do cool marketing stunts and they've expanded into all these other skus and the products are genuinely good. I just love that as a brand. And if you can say I market like I sell water. And in 2026, when it's probably the most, literally the most commoditized product in the entire world, I just have so much admiration for, for what they've built. So that's my pick.

Speaker B: Uh, we're on the same page. I had a cola flavored sparkling water, Liquid Death today. And I. So good.

Speaker A: They're Dr. Death. The purple one, the Dr. Death. I drink probably two of those a day. They're my absolute favorite.

Speaker B: Uh, as soon as we get done with this, I'm going to go order that.

Speaker A: Perfect. You'll enjoy. You're welcome.

Speaker B: Uh, Ben, well, thank you for this entire session. This has been. I know I've learned a lot as a brand builder in investment management, and I know everyone watching has learned a lot. Thank you so much.

Speaker A: Thank you so much for having me. It's been fun.

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