Recall Sessions: The PR Playbook Most Founders Get Wrong — Paul Loeffler & Kelly Boynton

14 May 2026 · 52 min · 25 chapters

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In short

How founders should craft and distribute a differentiated launch story, what PR agencies actually provide, and how to evaluate earned media vs paid/owned channels.

Key claims

Customers are the best storytellers; founders often misalign expectations by thinking agencies “buy coverage” rather than delivering strategy, narrative shaping, media relations, and pattern recognition. Credibility, reputation, and differentiation are the most valuable currencies in a noisy market. PR works best as a long-game system that compounds, not a transactional “get leads from one announcement” tactic.

Notable examples

Atlassian’s contrarian product-led growth (smaller teams buy; documents open by default) and Gusto’s contrarian AI/jobs perspective (displacement leads to new businesses). Press releases are “alive” mainly as infrastructure for facts/SEO, but blog posts/opinion better support storytelling. Stealth is only advisable for the minority with real IP protection; otherwise, competitors define the category quickly.

Guests

Kelly Boynton (Head of Communications at Gusto; led comms/economic research; prior Facebook/Instagram/Intuit/TripActions/Nivan/DocuSign agency+in-house) and Paul Loeffler (former SVP Comms & Brand at Bill; led integrated comms at Gusto; joined Atlassian pre-IPO; scaled global product/financial comms, M&A, exec thought leadership, crisis; agency-side startup IPO/acquisition exits).

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

Misaligned Expectations in PR

0:45 to 3:22

Founders often misunderstand what they gain from hiring PR agencies.

“reputation, differentiation, those are extremely valuable currencies to be able to have.”

The Importance of Launching a Company

4:30 to 6:30

Founders learn how to effectively define and tell their company's story at launch.

“I think actually your customers will always be your greatest storytellers.”

Validating Your Story

6:30 to 9:14

Founders are advised on how to validate their company's narrative with customer feedback.

“And then let's look at it and be like, is this the story, like, from their point of view, which is sort of an exercise that they find annoying.”

Standing Out with a Contrarian Perspective

9:14 to 12:11

Discussion on how a unique perspective can help companies differentiate themselves.

“From a product standpoint, it was about enterprise collaboration.”

Effective PR Strategies for Founders

12:11 to 14:00

Exploring different PR strategies and how to engage audiences effectively.

“The reality is, if you're building kind of a cookie cutter approach, you're going to get cookie cutter results.”

Business Models and Effective Communication

14:00 to 14:59

Learn how to evaluate business models and the impact of communication channels.

“So it comes down a little bit to, again, thinking about what kind of business model do we have?”

Value Versus Valuation in Storytelling

15:00 to 16:39

Understand the importance of focusing on value instead of valuation in storytelling.

“I think a lot of it is around creating the conditions for success, which I think is what you were saying.”

Hiring an Agency: When and Why

16:40 to 18:19

Discuss the circumstances under which founders should consider hiring a PR agency.

“And now they've come to this decision of we like people to write about us.”

The Role of Founders in PR Success

18:20 to 20:00

Explore the critical role founders play in effective PR strategies.

“So a lot of agencies that I think are at the top tier, they will sit there and have a conversation.”

Preparing for Media Interactions

20:01 to 21:39

Learn the importance of preparation and research before engaging with media.

“If they can spend at least an hour a week doing story building or practicing of being able to tell the story, that's the bare minimum.”
Show all 25 chapters

Understanding PR as a Core Function

21:40 to 23:19

Understand why PR should be a core focus for founders rather than a side project.

“It's what else is happening in the world that is relevant to this conversation.”

Evaluating the Value of PR Agencies

23:20 to 24:59

Discuss how to assess the value and expectations when hiring a PR agency.

“I would say if you are ready, it feels very manageable.”

Long-term Investment in Credibility

25:00 to 26:39

Learn the importance of investing in credibility and reputation over time.

“So I think that's part of some of the challenges, a little bit of the misalignment or the expectations around what value, what does this relationship exist for in the first place?”

Finding the Right Agency Fit

26:40 to 28:00

Get insights on how to choose the right agency partner and assess fit.

“But what would be some tips for founders as they're evaluating potential individual or agency partners to assess whether there's something to work on together?”

The Importance of Challenging Conversations

28:00 to 29:15

Learn why asking tough questions is essential for productive partnerships.

“I think you want to have someone ask you lots of questions, right?”

Understanding Media Coverage Expectations

29:15 to 30:33

Discover the misconceptions founders have about media coverage and how to align expectations.

“And they have this false expectation that, hey, I saw another company get written up on ABC Place.”

Building Relationships with Journalists

30:33 to 33:02

Explore strategies for cultivating meaningful relationships with journalists.

“What can we do to earn more of what we want to as well?”

The Role of Press Releases in Modern Communication

33:02 to 36:18

Understand the current relevance of press releases and their role in storytelling.

“If you are demonstrating that you are trying to provide value, most journalists are going to be excited of, great, here's an expert that I can sit there and talk to and get perspective on so that I can become smarter.”

Stealth Mode vs. Visibility in Startups

36:18 to 37:25

Analyze the pros and cons of startups operating in stealth mode versus being visible.

“You're talking to a different audience usually with a blog post versus a press release.”

Evolving Dynamics of Communication Strategies

37:25 to 41:41

Learn about the shift in communication strategies over recent years and their implications.

“To quote Ferris Bueller, life moves pretty fast.”

Effective LinkedIn Engagement for Founders

41:41 to 42:00

Discover the best practices for founders to engage on LinkedIn without overdoing it.

“Everybody's tried to turn it into a thought leader.”

Creating Engaging LinkedIn Posts

42:00 to 44:27

Learn effective strategies for crafting compelling posts on LinkedIn.

“I would say it's a good thing if you have something interesting to say.”

The Role of Ghostwriting in Comms

44:27 to 46:57

Understand the pros and cons of ghostwriting for founders and execs.

“they are having a huge value of Reddit content.”

Founders' Advice on Effective Comms

46:57 to 50:19

Discover crucial communication strategies for founders to engage audiences.

“For founders that are listening, if there's one thing you would tell them to start improving upon or starting doing in the realm of comms, what would be the one big piece of advice you'd give?”

Balancing Product and Storytelling

50:19 to 51:42

Explore the integral relationship between product quality and effective storytelling.

“Using the word revolutionary with nothing to back it up.”
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Transcript

Automatic transcript. May contain errors.

0:00In reality, a company will probably never be better at telling the story than the customer will be able to tell the story on your behalf. Does the customer sit there and get excited about what you're doing? Are they so excited that they're willing to sit there and tell others about it? If you can get your customers to talk about what you're doing, that's the biggest test that you'll ever want to be able to pass. So I would say this is actually about misaligned expectations, because what you're actually getting when you hire an agency is not coverage. You are getting strategy. You're getting some support on storytelling.

0:29you're getting the media relations, the pattern recognition. It's all of that. Founders, what they don't like, to your point, is it's this kind of unexpected outcomes. That's what they get upset about. They think that they just bought coverage, and that's not what they actually bought. The most valuable currencies right now in a very crowded, noisy world, credibility, reputation, differentiation, those are extremely valuable currencies to be able to have.

1:04Today, I'm joined by two comms leaders who have helped build the narratives at some of the fastest growing companies in tech. This topic comes up constantly with founders. How should I think about launch? How do I get TechCrunch to write about my company? Is hiring a PR agency worth it? You'll hear stories like, we spent$15 ,000 and got one article. So we're going to dig into what actually works. Kelly Boynton is the head of communications at Gusto, where she leads Gusto's communications and economic research team, overseeing corporate, executive, product, financial, and crisis communications, as well as proprietary economic insights on the small business economy.

1:38Before Gusto, Kelly spent 15 years across agency and in-house roles, building communication programs for companies like Facebook, Instagram, Intuit, TripActions, now Nivan, and DocuSign. Paul Loeffler has spent 20 years building and scaling communications for category-defining companies. He is the former SVP of communications and brand at Bill, and before that, he led integrated communications at Gusto. He joined Atlassian pre-IPO and helped scale it as a public company, running global communications, including product and financial comms, M &A, executive thought leadership, and crisis management.

2:10He's also worked on the agency side with leading startups that went on to have successful IPOs and acquisition exits. We're going to talk about what founders get wrong about PR, when it makes sense to hire an agency, and the growing trend of founders skipping traditional media and building distribution directly on LinkedIn. Let's get into it. So, Kelly and Paul, super grateful that you both are here. I've been wanting to do this for a long time. I don't feel there's a lot of great advice to founders about what comms is all about, how to do it right, and how to approach working with journalists.

2:42And I'm grateful that you guys are here to kind of share your perspective on what the the tricks of the trades are and the inside baseball. And so we're going to jump right into it. Is that cool? Absolutely. So let's start with some basic stuff. One of the most common questions that founders kind of come to me with is just like, hey, I want to go launch my company. So I work a lot of early stage companies. A lot of listeners here are building their companies for the first time. And what does launch mean to someone who's doing comms in a professional setting? It means introducing the company kind of to the world.

3:12It's usually the moment where you're really thinking about how are we defining our story and what do we want to become known for. And like the essence of comms is you want to become known for things that matter to the people that matter to you. So when you're launching the company, it's kind of that first introduction to the people that you care about. You're becoming known for things that they care about as well. I mean, let's start there. It's like, what is a great story? What are some sort of traps that founders kind of get into where they think they have a great story, but it sort of falls flat?

3:41I think the first trap that they fall into is the group that they're around says, oh, that's a great story. As opposed to starting with the group that really determines if you have a great story is not inside your company and it's not your VCs, it's your customer. Do they think that you have a good story? Do they think that you have an understanding of what they're going through or what they need and that you are delivering on those needs? And I think that's the classic trap of almost starting internally as opposed to starting more externally about whether or not you have a good story. And a lot of founders, how do they validate whether they have a story that's worthy of telling?

4:19How do they validate it? Yeah, just how do they validate it? Do they talk to their customers about it, or is that a safe place? Obviously, we are here as investors to kind of hear about it, but we're not the experts in all things storytelling. I think actually your customers will always be your greatest storytellers. And so I think that's one of the things that, you know, a lot of times you're like, oh, it should be like it's our story. We should be great at telling that story. In reality, a company will probably never be better at telling the story than the customer will be able to tell the story on your behalf.

4:52And so, like, that's usually the best test. Does the customer sit there and get excited about what you're doing? Are they so excited that they're willing to sit there and tell others about it? Like, you know, you think about as a test, if you can get your customers to talk about what you're doing, that's the biggest test that you'll ever want to be able to pass. It doesn't matter how much money that you'll put into your own channels. It will never be more efficient or more effective than if you get customers to want to be able to talk about what you're doing themselves. One of the things that I feel is getting harder and harder is standing out and being differentiated.

5:24I feel like every story is getting kind of sounds the same. You know, hey, there's another company. And then, oh, there's another company like five weeks later that launches again. You're like, hey, I can't tell the difference. So like founders struggle with this. How do you all think about that when you're, if you're talking to a founder or working with a CEO that's trying to tell their story, but it doesn't come off highly differentiated? I think you want to look for kind of what other people aren't talking about. I also think you want to ask yourself the question of like, what is happening right now in the world that made my company inevitable?

6:03I think that is a very personal story that you can uniquely own. Again, I guess getting back to some of the customers, I mean, having conversations with customers, those are great POVs that you can bring forth. Being able to spot edge cases early, things like that, bring additional color to any story you're telling. Is there an artifact that you all sort of advise founders to kind of write down? I mean, you know, at least something I always say, I'm not sure if this is good advice so you can shit on it, but, like, I say, hey, write the article you want someone to write about you. And then let's look at it and be like, is this the story, like, from their point of view, which is sort of an exercise that they find annoying.

6:48But I'm like, hey, if you write it in that perspective, maybe that will help me understand the story you want the world to tell. the world to tell. I think that's a good test of if you write down what you think your story is and what you want people to say about you, and then you go and look at it, and then you start to sit there and say, well, if I were calling bullshit on myself, where would I call bullshit? Like, where is this maybe a little bit too self-serving versus reality? I think another good artifact that you can create is, and going a little bit to like what we were talking about earlier, create kind of an issues map.

7:18If you think about, all right, the different stakeholders that you care about? What are their wants and needs? What are things that they wish could exist that doesn't currently exist? And then how are you kind of filling in that gap? Going back a little bit to one of the earlier questions that you asked too, when you're introducing a company or product, you're basically saying the world is missing something or something in the world is not the way that it should be. So I'm building something to solve for that need. So in some ways, the more that you can have a contrarian perspective from what is currently out there in the world, that is a good way to sit there and build relevance and to your question of how do you stand out.

7:55If you're saying what everybody else is saying, you're just saying it differently, that's not going to help you stand out. That's just helping. It's another version of you fitting in. But if you're introducing something new into the world, you have a very core conviction that something should be different than what currently exists. And so you have to kind of lean into that contrarian perspective because that's what actually gets people to pay attention. And if everybody's saying the same thing over and over again, then it almost becomes whoever spends the most ultimately is the one that's heard.

8:22If you want to be able to have your voice heard, you have to sit there and say something that's new and different. So I always encourage founders to sit there and lean into the contrarian perspective. Where should something be different? What's your contrarian perspective that you can add to the conversation? And that's a much more effective formula to being able to stand out. And is it always product-oriented contrarian? What are the different types of contrarian kind of points of view? It could be products. It could be about industry issues that are affecting. It could be about business models.

8:50A good example, when I think about time at Atlassian, especially in the enterprise software, it was very much a sales-driven motion. And Atlassian had a very contrarian perspective as a business of saying, we're not going to have a big, giant sales team. We're going to have product-led growth. We're not going to just do big deals. We're going to allow people to be able to purchase for smaller teams. And so that was a very fundamentally different perspective from a business. From a product standpoint, it was about enterprise collaboration. Every document for Atlassian, or every product and document, was opened by default.

9:26Most products at the time, you had to sit there and add people to be able to have access to it or to be able to have permission. So those were good examples of being able to, from a business model standpoint, from a product standpoint, of having a contrarian perspective that enabled them to be able to stand out. Yeah, I would also just add on like perspective on where the world is going. And kind of pulling again from something familiar to me at Gusto, there's a lot of noise right now externally around how AI is destroying jobs. And there's going to be this dystopian future, very Wally. And that's not the perspective of Gusto.

10:03It's that we, yes, there will be some job displacement, but those people are actually going to go and start tons of new businesses. And it's actually going to be a really prosperous time where people really feel that they have purpose. And they can use those tools to go pursue something that they really care about. So, again, I think it's the contrarian view of what the future looks like. So let's say someone feels really good. Someone gets to a point where they feel they have a contrarian kind of point of view. They drafted a story that they buy themselves. They want to tell the story out to the world.

10:37there's a lot of perspectives of like do I launch a press release do I you know pitch journalists do I just not do any of that and just write a blog post like how do you determine which strategy is right to tell that story to the world I mean is there any is especially in this day and age yes you know what what are you trying what are you hoping to accomplish by telling the story Well, I mean, you know, for most founders, they want to they want leads. They want people to see, you know what you I mean, they're ultimately looking for prospects and customers. I'm not sure if that's the right way to think about it.

11:15I mean, but that is what most folks are hoping is like, hey, we're going to have this moment and we're going to like, you know, obviously there's product content and so forth. They're like going to use this sort of opportunity to tell the story to the world, whatever version it is. and hopefully there's enough eyeballs that turn into some flywheel of inbound. I'm not saying that's right, but I'm just saying that's what there's a perspective around. There'll always be different dials that you turn depending upon the stage and where you're at and everything else. But the kind of constants will be what audience are you trying to reach and what are you trying to influence as a result of it?

11:52And depending upon what answers you fill in for those questions, then you start to think about, okay, how would I line things up from a tactical standpoint? I think going back to traps, it's easy to fall into the tactical execution of like, oh, I've seen other companies, they do a press release, they announce their funding like this, or they do this. The reality is, if you're building kind of a cookie cutter approach, you're going to get cookie cutter results. You want to sit there and think about what moment are we in as a business right now when we're sitting there and lining up a specific campaign or an announcement or anything else.

12:24Not only what am I trying to accomplish with that, how does that set the table for the future? If you are doing a funding announcement, do you have anything else coming down the road over the next two to three quarters? Or is that it? Then you have to think about that funding announcement very differently if that's the main thing you have. But if you have a ton of other announcements, you potentially think about packaging things together so you can sit there and create a bigger moment. So there's a lot of context that you need to think about, but the constant questions you're always going to look at is, who am I trying to reach and what am I trying to influence them?

12:55And then you start to fill in the tactics to support it as opposed to starting with the tactics. Is it wrong that founders look at, I'm going to call it PR. We'll talk about what the hell the fuck that means. PR is a dirty word. We'll talk about that in a second. But is it wrong for that? Because I say, hey, don't expect leads out of this. Maybe I'm wrongfully saying that, but because I'm just like, hey, I don't know how many people are going to say that. But if that's the bar, it feels like a really, I don't know, it feels wrong. I don't know. It's just like one event. It's like all of a sudden I'm going to get like 100 leads.

13:30Is that wrong that I'm giving that advice? For 90 % of the businesses, I think that advice is spot on. Like very rarely should you sit there and think of you're going to have a transactional result of leads just because you put out an announcement. But it also depends a little bit. But thinking about some of the stuff that we worked on with Gusto and BED back in the day, we weren't necessarily looking for signed deals, but we were looking to sit there and put an announcement and then drive inbound interest for more potential partnerships. So you were looking to sit there and help to build the pipeline and generate some interest.

14:04So it comes down a little bit to, again, thinking about what kind of business model do we have? What kind of announcement would we even be making in the first place? And how would you look at it? But the way I would think more about it is, are you creating inbound interest? Are you extending conversations in the space that you are? Those are better ways to think about the impact that comms can have, as opposed to just thinking about, I'm going all the way down to the bottom of the funnel. I think that's the other part, too. There are certain channels that are more effective for different parts of the funnel.

14:38Most comm channels are generally better for the top and the middle of the funnel. Getting down to leads at the bottom of the funnel and driving conversion, those aren't the best channels to be able to drive it. That being said, if you have a good playbook that's happening at the top of the funnel, all that money that you're spending at the bottom of the funnel will work more efficiently and more effectively for you. So they work together as a system. Yeah. I think a lot of it is around creating the conditions for success, which I think is what you were saying. The other thing you mentioned is, again, they're like, okay, I have this announcement, so I'm going to craft all of these things.

15:12I think that's also the wrong way to look at it and how you're going to build relationships with media and whatnot. I think, again, you start with the coverage is not the asset. It's actually the narrative. And you need to build that over time. And you have to show up again and again with data, with insights, with perspective. So when the time comes and you have that announcement, you're not doing all that work. The story will basically help tell itself because you've already done all of that kind of pre-work. One thing going back to of thinking about a framework, a lot of times it's easy to get trapped in thinking about valuation as your story.

15:50The value is the story that you want to have. And so I think a lot of, especially when it comes around funding moments or various proof points in a company's journey, they want to be like, ah, we have this new valuation. We just raised this money. In reality, the more that your story is grounded in your valuation, that's about you. You're doing storytelling, not for your own purposes. You are doing it on behalf of somebody else. So the biggest thing that I try to help coach founders on a lot is your story should be about value, not valuation. And especially in the early days when you are just getting started out and you're still trying to build your story, the more you draw it into, I think, as Kelly was talking about, like these different announcements, that helps you to fall into the valuation trap.

16:35And that's the worst place for your story to really be if it's long term. You really want to get more to your story being weighted on the value side, not the valuation side. Okay, so someone has a story. They're ready to tell us the world. And now they've come to this decision of we like people to write about us. And they want XYZ publication to tell the story. And I'm like, okay, where do they start? Do they, should they hire an agency? They're always like, and obviously these agencies can have varied pricing that people wonder, is this, what am I getting out of it? Like, what is the right approach?

17:20And maybe we can talk about what's the value an agency kind of provides that conversation. You guys have both worked in an agency. You've been part of the other side. You've been on both sides. What's your take? Okay. On the agency side, like what is the value an agency provides? An agency can provide strategy. It can provide narrative shaping, media relations, pattern recognition. The founder has a really important role to play in all of this, which is they are the ones who are bringing the actual insight. They bring the energy. They bring the conviction, the voice. So I think those work together.

17:57Again, this comes back to, like, do I hire an agency? And the question isn't do I. It's really, like, are they ready? And how do you know whether you're ready? Will the agency tell you? I think one of the most important rules that an agency partner or even an in-house partner plays is challenging. And basically saying, hey, all right, let's hear what you think the story is. And then giving you an honest perspective of being able to sit there and say, all right, if I look at the external world and I put that test to it, we're not ready from a story standpoint. So a lot of agencies that I think are at the top tier, they will sit there and have a conversation.

18:34And before they say yes, like, let's work together. They want to understand what do you have? What are you trying to accomplish? And they'll sit there and do the math of saying, like, yep, we can help you or nope, we can't help you. Will they say that, to be honest? A good agency partner will. When I was on the agency side, there would be a number of times of talking with founders and doing new business calls where I'm like, yeah, what you're trying to accomplish, you're not ready for that. If you're going to go and spend money, like, that's not actually going to help you to get to the results.

19:02And a good salesperson knows, like, you don't go and do a deal unless you know that person's going to keep wanting to come back to you. And so, you know, the best agencies will sit there and be honest with you about whether or not they can actually help you to accomplish what you're looking to do. You know, it's interesting, too. It's like one of the other things that you really need to have an understanding of is, are you ready to actually invest the time? An analogy I would think about is if you wanted to sit there and get in shape, you wouldn't hire a trainer unless you actually have time to go to the gym to work out with that trainer.

19:36If you know that your schedule does not allow you to have the time to do it. And what is expected of a founder CEO that demonstrates to the agency that they're willing to commit? Because they'll say, oh, yeah, no problem. I'll do all those things. Like, what does that really mean? What are those things? So I would say some of that depends on, okay, how much time do they actually have? If they can spend at least an hour a week doing story building or practicing of being able to tell the story, that's the bare minimum. If you think about the amount of time, let's say you plan to have three conversations a week with various journalists, podcasts, et cetera.

20:17You have to triple that amount of time to think about it from a prep standpoint and a research standpoint. And so if you take one hour of actual time and then multiply it by three, that helps you to start to have a better sense. So let's say you're having three conversations a week, plus you're also talking to your agency. That's 10 hours of your week. And so you start to sit there and do a test with your schedule based on, you know, imagine you are wildly successful with sitting there and building your comps program and getting your story out there. That takes time. It doesn't all of a sudden result in less time.

20:50This amount of time that it takes to actually build the story will get less. But the more effective that you get at telling your story and the more opportunities you have will ultimately take more time. So I think the thinking about a three to one ratio of every hour that you'd actually spend talking to somebody, assume that it's going to take three hours to do research and to prepare. What research are they trying to like? What does research even mean in that context? Is it just like researching on the person on the other side? Yeah, you need to understand what they're like. Like, when you're showing up to a conversation, you need to understand what a journalist covers, what they actually care about, what does their audience care about.

21:24And those are very kind of basic fundamental storytelling questions that need to be prepared as a part of the research. Didn't know that. I thought no one prepares as far as I'm concerned. Yeah. And just to build on that, it's not even just what this reporter cares about. It's what else is happening in the world that is relevant to this conversation. And also, you've got to prepare for the not-so-fun questions, right? It's not just, you're not going to just be there. It's not going to all go easy and as you wanted and expected. You have to prepare for the unexpected. And that takes time, too. Really quickly, and I think this is kind of the point that Paul was making, is that mistakes founders make would be they treat PR as a side project.

22:04It is part of their job. So if you are able to give it the time, that's critically important to being successful. I would also say, again, this is kind of playing off of what Paul said. It's like, okay, when the momentum starts going, mistakes are when a founder all of a sudden disappears. You actually need them to show up and be responsive in a timely manner. I would say PR generally, it favors speed and consistency. The thing I hear about when we introduce an agency to a founder is like, holy shit, I don't know that it's going to cost this much. how do you if you were if a founder was here and you were advising them on how to think about the value of of that investment and by the way there's always there's solo agent there's solo you know freelancers that do an amazing job there's also firms there's stuff you know big ones small ones they're always and and they think of this as i just need to get an article out there they think of the outcome and so and they have unfortunately it's just war stories of founder working with some agency, I only got one article, and I'm not really happy about what I've said there.

23:06How do you sort of eliminate, what is the real way to think about how to evaluate whether a partner like an agency is actually delivering on the value that's expected? I would say the problem is not necessarily about the expense. I would say if you are ready, it feels very manageable. If you're not ready, it's very expensive. It's a waste of money. And I don't think, again, back to the founder question, which is, I would say it's not, again, that they're expensive. It's that the founders think that what they are getting is automatic coverage when they hire an agency. So I would say this is actually about misaligned expectations, right?

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23:49Because what you're actually getting when you hire an agency is not coverage. You are getting strategy. You're getting some support on storytelling. You're getting the media relations, the pattern recognition. It's all of that. And I think founders, what they don't like, to your point, is it's this kind of unexpected outcomes. That's what they get upset about. They think that they just bought coverage, and that's not what they actually bought. The other thing I think about it, too, is if you think about the most valuable currencies right now in a very crowded, noisy world, credibility, reputation, differentiation, those are extremely valuable currencies to be able to have.

24:33And so the way we think about the role of a comms program and an agency partner or an in-house partner, those are the people that are charged with making sure that the company has a strong reputation, is credible. So all the things that you want to be out there talking about in the world, people believe what you're saying. If you have low credibility, if you don't really have a lot of differentiation, it's hard for you to be able to stand out and ultimately for people to sit there and be interested and engage what you're being able to say. So I think that's part of some of the challenges, a little bit of the misalignment or the expectations around what value, what does this relationship exist for in the first place?

25:15And what's the value that I'm looking for? it. If you're playing the long game, you're thinking about your credibility, you're thinking about your reputation, you're thinking about how you create differentiation. And so, you know, when you add up the cost of that, that is something you would sit there and invest in very deeply because you were going to always need that. If you're thinking about it from a lead standpoint, you might not necessarily see the same kind of result of the return during those spikes. The other point too, I think that Kelly made it that was really good. If you invest in a program, it becomes more efficient.

25:46It's almost like gas mileage. When you have your foot on the gas driving down the road, you get very good mileage out of the gas that you put into. But if you pump the brakes or if you're going around the city and you kind of start and stop, you're paying way more than you would have to. So the more that you continue to invest, it will compound in terms of the value, especially when you think about it from a reputation and a credibility standpoint. How, you know, we have founders that are always introducing other founders to other agencies or individuals that are freelancers, how do you evaluate whether, I mean, if you're talking to a founder and saying, hey, how do you find the right fit for you?

26:21How do you know? Because everyone's saying, I got relationships with A, B, and C. Like, oh, hey, I feel like I can tell your story. I mean, at least having done this before, like in prior companies I founded, it felt like everybody was saying the same thing. How do you know this is the right fit for me? And obviously, you're going to get advice from others, and everybody's saying good things about agencies. But what would be some tips for founders as they're evaluating potential individual or agency partners to assess whether there's something to work on together? Other than chemistry. Two areas that I look at, like, will they debate or can they debate with you where you're finding it?

26:59You're looking for that. Yeah, you want to have a debate. If you're not having, the best storytelling ends up usually as a result of some form of debate. And if there's no debate or there's no challenging going back and forth, that's usually kind of a sign that that's probably not the partner for you. Because rarely does good storytelling just all of a sudden words fall on a page and you're like, that's great. Usually to find something that's interesting, there has to be some drama. There has to be some edge to it and there has to be some contrarian perspective. And that happens through debate and challenging.

27:31And so when you're looking for a partner, you should want that. even if it's not something you enjoy, you should expect that. So should a founder in that context, Paul, be like, hey, what do you think is wrong with our story? Or should they be poking holes in it? And if I were on the agency side, I would be like, hey, I have advice, but I'm not ready to share with you because we're not working together. Is that a thing? I imagine that could be a thing. Where an agency doesn't want to kind of show their cards. Yeah, they don't want to show their cards because I'm already creating value for you.

28:01I think you want to have someone ask you lots of questions, right? You want them to be, besides the kind of poking holes, and I think that gets to debating, right? That's what leads to debating. It's the asking questions, showing that you care, that you're excited, that you're passionate and curious. Got it, got it. So let's say you hire a... Beware of somebody who says, wow, you're amazing and doesn't follow up with anything else. We're so excited to work with you. You're the hottest company in the space. A lot of compliments and platitudes, that's usually when I start to go running. Because it's one of those where that's fine.

28:39I already know what we're good at. Where I'm looking for is how are you going to make us better? How are you going to make us sharper? What do you have an understanding of that I don't that I need? And so when you think about a good partner, you don't want a partner that knows exactly what you know or thinks exactly the way. The value of a partnership is you are bringing somebody that adds something to the table. So that perspective is super important. and somebody that's overly complimentary, that's probably not who you want to be working with. There's this, let's assume that a founder kind of understands the value of the agency and now they're ready to engage and formally start working together.

29:17And they have this false expectation that, hey, I saw another company get written up on ABC Place. Why can't I get written up there too? This is like, I hear this all the time. And I'm like, one, I don't know what to say in that situation, But like, what would you say to that founder who is like looking at the world and saying, hey, I'm special too? Yeah, I would say reporters don't write about companies. They write about trends. They write about what's happening in the world. And if you're proof of that, you might get picked up and or someone else might get picked up instead. So I would say, again, it's not about you.

29:54It's not about your company. It's about what is happening in the world. and if you are proof of that or part of that conversation or can contribute to that conversation. Yeah, there's a common misconception, too, of like, oh, because another company got written about, I should be too. The understanding of that earned is different than paid. And so I think a lot of times, like, whenever I've had a founder come and say, like, oh, XYZ competitor was in that story. Like, we are way bigger. We have more money. Like, we have more revenue. We have more customers, all these different things. You want to go and dissect the story of, okay, what did that company do to potentially earn what they got?

30:37What can we do to earn more of what we want to as well? But not losing sight of like, it's always an earned game. Like there are times where relationships will sit there and open doors, but the stories that end up happening as a result of it, there's still a component that's earned of it. You know, there are new media or like there are VC podcasts still like they want to be telling the best stories, you have to earn it. Even if you do have an in, that doesn't give her a T that you're going to get something. And so making sure to never lose sight of the fact of earned means you actually have to do the work.

31:09Yeah, I mean, this kind of happens a lot where a founder kind of comes to me and say, oh, hey, I met with XYZ. They work with agency. They met with a potential journalist. They tell their story and they say, they didn't write about us. And I'm like, okay, what do you tell those founders that are like, hey, I'm sorry they just didn't find your story compelling or something like that. Because it happens a lot. I mean, the way to building relationships with reporters, engage with their content. Like, follow up on that relationship. That's supposed to be the start of a relationship. It's definitely not the end.

31:43So comment on their posts when you have an opportunity or see a way to provide an interesting perspective. Do that as well. And then, I mean, the kind of rule of thumb is don't, you know, ask for something before you kind of give something. And so I think I would treat this again. It's a relationship. It's not. But in practice, what does that mean? Is it like, hey, when I see when I read something that a journalist kind of wrote about anything that they're writing, do you just email them and say, hey, I mean, you can't be lame and be like, hey, I like what you wrote, you know, period, send. I mean, what is the right approach?

32:21is too much, too much, like what is the right balance here? Is there any rules of thumb or just like don't be a creep? Which is probably a good rule of thumb. I would say most of the rules that you probably learned in kindergarten are very appropriate. And when you think about engaging, don't be a creep, don't be whiny, and crying about like you didn't get something that somebody else got. If you follow kind of like basic rules, you should be fine. But reaching out, saying, hey, I've been paying attention to what you've been reporting on. I think these are really important issues that you are talking about.

32:58I would love to grab time and talk to you more about them. If you are demonstrating that you are trying to provide value, most journalists are going to be excited of, great, here's an expert that I can sit there and talk to and get perspective on so that I can become smarter. Or I can be more informed or understand something that I didn't already know about. So if you lead with you are trying to actually help and be in service of storytelling that is not just about you, that will open up a lot of doors. I think another important point that Kelly was raising, too, you can't treat relationships with journalists transactionally.

33:35It should not be, I'm only going to talk to them if I'm going to get a story out of this. Worst thing you can ever be doing is trying to go tell an important story to the first time for somebody that you've never spent any time with. Like you want to be going to people that you're like, okay, we have an interest. We understand their perspective. I have a sense of how they're going to be telling this story. You don't want to just be going to them of saying like, here's my story. They may be really excited and then not understand your story and tell it in a way that you don't believe is true. So one of the things that's most important is to not treat relationships transactionally.

34:09And also to really think about like, okay, this is the right person to tell my story. I'm going to spend some time with them before it's time for them to be telling my story. What's your take on this press release as a concept? Is it dead? It's alive and well. The wire, is that even? I mean, it was not. I would say. They still charge money. It's still a business body. I don't know,$2 ,000,$3 ,000 per wire or something per publication? It's based on word count. Okay, word count. Again, I think press releases are back, but not as a strategy. Press releases are back because of LLMs and GEO, which has made them relevant again, but not, again, as a strategy, more as part of, like, an infrastructure.

34:53Tell me more about that, because this is—I'm curious about what you mean by that. Is it because of LLMs? Is it just like, hey, should you have a press release every three months? Is that a good idea? If you have a story to tell, then—because if I don't get pulled by a publication, then this is the default. And I'm like, all right, I mean, it's not as good because no one wrote about you because you wrote about yourself, right? Press releases, like BusinessWire, like they help with authority, but that's it. It's an additional thing to do, but it is not the way, like you don't start with, okay, we have to go write a press release.

35:29You still think about like what's the story. Press release is not usually the best kind of model for being able to do effective storytelling because it's about news and facts. It doesn't usually bring an opinion as much. And so you want to do it so you can sit there and get the facts part. But if you're thinking about, like, all right, I really want to sit there and talk about my story, a good story from a company and a founder should have a perspective on issues. So a lot of times what you'll see companies do is they will issue a press release for the exposure for GEO. But they also will end up doing a blog post as well because they want to do the same thing.

36:06I mean, it's the same content or are they just... Blog posts, generally, you don't focus on. You have news elements, but you also have more opinion. That's built into it as well, whereas traditionally a press release is just facts. Yeah. You're talking to a different audience usually with a blog post versus a press release. Yep. Press release, you're rarely talking directly to your customer. If you're trying to do good storytelling and you're sending your customer press releases, you're probably selling yourself short. Right, right. So I think what Kelly's hitting on, you're thinking about what are the tactics match to the audience and the channel that you're ultimately trying to reach.

36:40What is your take on companies that are staying in stealth? Like, do you think stealth is, you know, this is a... I haven't figured this one out because, you know, I'm going to stay in stealth. And then there's this other point of view, which is always posting on LinkedIn every single day. Like, I've seen both, and I'm like, I don't know whether one strategy is the better. What...is there a better approach to this? I think for the probably 5 % of companies and stuff that actually have IP to protect, smart move. For the 95 % others, I think they just haven't figured out how to tell their story.

37:17But is it okay? I mean, most folks aren't like crystallized their perfect story. So they're just like, it's like how perfect does the story have to be when you're out there in the world? To quote Ferris Bueller, life moves pretty fast. Especially right now. And I think it's one of those where do you want to make sure that you have a good story to tell? Yes. Do you need to have a perfect story to tell? No. And so I would think about why are you in stealth? Is it because you don't feel like the product's ready and that you're going to be putting something out there where a competitor is going to gain an advantage?

37:53Or if you're not doing it because you're not ready, you damn well better get ready faster. because if you wait six months, the industry may be already defined by competitors. I feel like bigger companies are hiring comms people earlier just to kind of... Because effectively, I feel like there's competition everywhere on Day Zero. It's like, you know, whether you start right now and you feel like you have some proprietary thing, like in one month, you're like, oh, wait, there's two other companies basically doing the same thing. Yeah. One thing that's shifted a lot in the comms world, especially over the past few years, you're seeing more of the fractional.

38:27It used to be you either hired folks internally or you had an agency partner. There's kind of this hybrid model where you can hire a fractional kind of comms partner that there's a lot of advantages to. You can have somebody that's focused on your business, but at the same time, you're not making a huge investment up front, but they can still give you a lot of the guidance and perspective that you're looking for. It's also kind of a try before you buy for both sides. Like, a comp partner can sit there and say, like, hmm, business has potential, but until it proves, I'm not sure I'm ready to sit there and go into it long term.

38:59Same thing from a company perspective. So, I think one of those, like, there's, to your point around, like, businesses where they're hiring earlier, there's a way to sit there and, like, think about, okay, do I hire in-house, do I hire a fractional or a comp partner, or do I hire an agency? The model probably depends on, like, how mature is your space? Like if you have a nascent space that nobody's really invested in, and then all of a sudden you go try to hire a big in-house team, that's a very expensive kind of investment that's probably the business is not ready to be able to capitalize on.

39:31And so I think that's one of the other kind of important tests. How mature is your space or how nascent is it? Because that'll also help you to think about like how much storytelling can even be done in the first place. What do you think is, I mean, you brought this up, like in the last five years, what has changed most? about just whether it's storytelling, whether it's what's happening on the journalist side, whether it's about breaking through the noise. Like, what has changed about the work of getting your story out there that's different now than it was five, ten years ago? I would say five, ten years ago, it was very much a gatekeeping game.

40:10Like, you needed a journalist to write about you, so you mattered. That's not the case anymore. What has really changed is that founders now have the ability to access audiences through things like LinkedIn and podcasts and newsletters. And it's the one thing that I think people do get wrong, and there's a lot of conversation today about this, is just the role of media. And I think people are saying, oh, media don't matter. They don't matter as much. And that's just not true. Media is actually an incredible credibility accelerant. It's just not the only channel anymore. So I think less that storytelling itself has changed and much more of the distribution of it all.

40:55Owned channels are, I think, a much more powerful lever and have become much more powerful. And so even exec channels on social should be thought more of as owned channels because you own what's going to be happening through those channels, just like you do on your website or your email. I think one of the other things to keep in mind, too, is to not space chase. When all of a sudden a space or a channel becomes popular, everybody rushes into it, and then it becomes saturated super fast. LinkedIn, three to five... Yeah, it seems like everybody is doing daily LinkedIn posts. Yeah. Would you advise founders on that?

41:29It feels like that's what everyone's doing right now. Is that a good strategy? Is that what I mean? That's a good example of space chasing. Like, all of a sudden, LinkedIn's algorithm started more heavily promoting thought leadership. Everybody's tried to turn it into a thought leader. And now, instead of doing it on a very thoughtful kind of way every couple of weeks or once a week, now everybody's trying to do it on a daily basis. So you don't advise it. I would say... So looking for an answer here, guys. Yeah. Okay. So... I was getting there, but she's going to go now. What's the answer? I would say it's a good thing if you have something interesting to say.

42:03And if you don't, it's pretty strange. What if you have something interesting every single day? You think you have something. You must be the most interesting person in the world. That was a TF right there. I think a safe space to play in if you're just getting started on LinkedIn and you're pretty time-strapped because you're building your business would be one to two thoughtful posts a week. It would be having a really clear point of view that you continue to articulate in all of your posts. and then commenting on various industry trends as they kind of surface. Are there any strategies you're finding, and I'm not asking you to spill all the cool tricks you guys have, that are really effective nowadays that's sort of breaking through all the noise?

42:48I've always said something that I know I appreciated really from the time at Gusto is just data as a competitive advantage. And not like all founders have this, but some do. and, you know, or find ways to create your own proprietary data, you know, stuff, whatever. It's like ping people, get surveys to respond to things, and then turn it into that to an insight. I always say that, but it's a lot of work. I mean, but I'm not sure if there's any sort of tricks of the trade here. Yeah, there's kind of a couple. I think one is if you think about the formula of, like, what is genuine thought leadership, you need to have an issue, you need to have an opinion, and then you need to support it with facts and data.

43:29And so if you can think about structuring a post with that formula, generally those are the types of posts that perform the best. When you just have a lot of opinion, that usually starts to fall a little bit flat over time. And so I would encourage you to combine, take an issue that starts with the audience, then you sit there and have an opinion about what's going on with that issue, and then you have facts to actually support it. That's more full storytelling. and generally, you'll start to see conversation extension and conversation engagement. If nobody's ever engaging in your conversation, the value of that conversation is minimal.

44:05So there's certain channels or mediums that you're finding more effective now than a few years ago, even just last year or two years? It just really depends on the audience you're trying to reach, right? The channels are different audiences, or LinkedIn is still a go-to for those serving businesses. Reddit is like, especially when you're going back to the topic of press releases, for LLMs, they are having a huge value of Reddit content. And so engaging on a topic and an issue in Reddit that is not just about self-serving purposes, you can get great overall showing up in search and LLMs. It's grown significantly based off of that value.

44:55Another trick, too, is thinking about combining organic and paid. A lot of times there's kind of like a separation of a divide between church and state. What I found the most effective is if you are able to test an organic post and see if you're getting good engagement from it initially. If you put paid on top of that, like you will see. This is like the promoted kind of LinkedIn. Or it's like, hey, here's this sub stack that seems to be kind of taking off. Like, let's just drive more awareness to it. Well, and founder or exec channels actually perform much better than brand channels. And so you can actually set up and link an exec channel to be able to do paid boosting as well for organic posts.

45:36Do you think ghostwriting is like a good strategy for, I mean, clearly it's happening. It happens a lot in venture. It's like, I'm like, oh, hey, that's an amazing post. It's like, that's some ghostwriting. And I was like, oh, damn, I thought you wrote it. It's an interesting question to be asking comms people about ghostwriting. No, I mean, no, but what I mean by that is like, there's, you know, how do you get the authentic voice of the person, you know? I mean, I don't know if there's some founders like, don't touch it. I'm going to do it on myself. And you're like, okay, you kind of suck, but sure.

46:05I mean, on the ghostwriting question, I think it's fine. But to your point, like you think it's the founder who has written that. It's because they've been able to pass the test of like, would this person say this at dinner? You know, if you're a ghostwriter is providing you with TED Talks, I would say that's a no go. Storytelling is a team sport. Like you don't want any one team member just doing like doing all the lifting. If the comms person is sitting there and puppet mastering the exec, that's not good. And oftentimes I would encourage execs to sit there and say, like, your comms person is going to sit there and help keep you honest.

46:44So the more that you think about storytelling from a team sport, ghostwriting happens all the time. Rarely is it just ghostwriting purely 100 % of somebody writing on behalf of others. Like the best storytelling usually happens with a team together. For founders that are listening, if there's one thing you would tell them to start improving upon or starting doing in the realm of comms, what would be the one big piece of advice you'd give? And we'll start with you, Paul. Think external first. I think it's too easy to start by thinking about what you already know or understand inside your own walls or the group that you go with.

47:20Think more about the external audiences that you want to be able to engage with in the future and what they care about. Start external and then work internal. Kelly? Yeah. I would say don't lead with the announcement. Lead with the story. I would also say stop talking about yourself, your company, and start talking about what else is happening in the world. And then you can get to how that relates to what you're doing. Awesome. Okay. PR agency, worth it or waste some money for early stage founders? If you're ready, absolutely worth it. If you're not ready, you're just spending money that's not going to help you.

47:55And, Kelly, you can't say I agree. Okay. Let's see. It can be a value add. It also can be an expensive distraction. One journalist every founder should have a relationship with. Do you guys have favorites? I would say go with the one who is deeply covering your space and not go for the big tech ones. Yeah. Don't just go by the size of the audience of the publication. Go by the journalist that actually cares and spends the most time in your space. Okay. All right. I mean, most people go for audience. Press release, dead or alive? I guess we answered this one. Well, the biggest audience is not necessarily the most relevant audience.

48:33I know. I know. I know. Okay. Press release, dead or alive? Like I said, alive and well. All right. Well, I'm under the right circumstances. Founder posts on LinkedIn every day. Cringe or genius? Cringe. I would say it can be good if you have something good to say, but most of the time it's cringe. It's cringe. Okay. All right. So founders, you hear that? Don't do it. TechCrunch cover story still matters or overrated? TechCrunch is still super relevant to the tech audience. If you have a customer that you're trying to influence that are technology startups, definitely spend time there. If you are serving like...

49:09The trades? Yeah. If you are serving like small businesses, TechCrunch plays a role, but it's probably not the most important... It's not the publication that all your customers are ultimately reading. So it depends on what you're trying to accomplish, but there's absolutely relevance. Yeah. And I would say this goes back to the distribution conversation. Getting a really great tech crunch story, it matters. It signals credibility, but it's just not the only channel. It's not the only thing that's going to define you. Got it. Founder-led brand or company-led brand? That's a trick question. You go.

49:46You can have a good brand, especially on the B2B and the enterprise space. They are intertwined. It's almost a false binary. You can't sit there and say that you're going to have a strong company brand and no founder brand. And you can't just have a founder brand and no company brand. You need both. I agree. Oh, damn it. That is not what I want you to say, but fine. I'll give you that one. What would be the contrarian perspective? Or what would be the wrong answer? I'm just kidding. I actually agree. Biggest red flag when a founder pitches their story? Using the word revolutionary with nothing to back it up.

50:26Pretty sure Sam Altman used revolutionary. I'm pretty sure Steve Jobs did, too, for what it's worth. All sizzle and no substance. But did those guys have something to back it up? I don't know, actually. I mean, this is the most revolutionary phone. I don't know. I think he probably said that. What do you mean by substance? So if you're sitting there and making promises, but not necessarily showing the proof of how you're going to deliver on those promises, That's usually a bid right flag. We have the best this. We have the most amazing this. Nobody else is doing this. The most important part comes next.

51:02And if there's nothing that comes next, then... False fact. Yeah. The best comms is really just a good product. Agree or disagree? I would say that good product creates good stories. Good comms helps those stories get told. I would also say that there are probably plenty of startups in the startup graveyard that had great product that nobody ever heard of. Do you have a name? I'm not going to call anyone out. I'm going to be to pile on. She might want a job there in the future because I haven't done a product. All right. We're not talking shit about anybody. Everyone's great. What do you think?

51:38I think that you need both. Like, you can't, if you're winning today, especially with how competitive the market is, a great product is not enough and a great story is not enough. You need both. Hey, I really appreciate you both taking the time. I know I got a lot out of this. I know everyone else, too. I appreciate you all sharing your guidance and advice. And I'm pretty sure you're going to hit up by random people. So thanks for all of the guidance and advice. Thanks for having us. Thanks for having us, John.

52:16that.

From the publisher

Somrat Niyogi sits down with two of the most experienced comms operators in tech: Kelly Boynton, Head of Communications at Gusto, and Paul Loeffler, former SVP of Communications and Brand at BILL.

Kelly spent 15 years across agency and in-house roles before Gusto, including at Facebook, Instagram, Intuit, Navan, and DocuSign. Before BILL, Paul led integrated communications at Gusto and was at Atlassian pre-IPO, helping scale it as a public company.

They cover what founders get wrong about launches and PR, when an agency is worth it (and when it is not), why your story should be about value rather than valuation, why reporters write about trends rather than companies, why 95% of stealth companies should not be in stealth, and the comms playbook for breaking through the noise.

Thanks for listening. If you like what you hear, please review us on your favorite podcast platform.

Check us out on the web at www.villageglobal.com or get in touch with us on X @villageglobal.

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