Market Trends, Pitching Journalists, and Editorial Strategy With Phil Rosen

Phil Rosen is an award-winning journalist, author, and the Co-founder and Editor of Opening Bell Daily, an independent news and research outlet. As the former Senior Reporter at Business Insider, he has a passion for finance, market trends, content creation, and community building. Phil is also the Founder of the Creative Journalists Club, where he hosts dinners and events for media professionals in New York City. Additionally, he is a prolific blogger who focuses on personal growth and career guidance.

Here’s a glimpse of what you’ll learn:

[1:18] Phil Rosen reveals why he quit working for a mainstream newsroom to pursue independent ventures
[3:28] Insights on remaining informed of trends in a rapidly shifting market
[5:03] How Phil maintains a balanced editorial perspective in his newsletter
[8:24] Phil’s philosophy on editorial strategy
[15:46] The secret to gaining recognition on editorial content
[20:33] How to learn from and grow your audience
[25:32] Why AI may narrow the scope of human creativity
[30:07] Strategies for pitching your journalistic content
[49:21] The importance of reading books in a modern society

In this episode…

What does it take to stand out in a society bombarded by content and fleeting attention? With the media landscape shifting, strategies that once helped professionals gain media acclaim are no longer viable. How can you maximize your influence in your sector?

Having left a corporate news outlet to launch an independent media venture, Phil Rosen is knowledgeable about the changing landscape of media and content creation. He notes that leveraging industry insights and market trends in your discipline enables you to adapt and capture emerging opportunities in your business. To maximize your presence and gain visibility, it's crucial to regularly create and share content, interact with your audience, implement their feedback, and establish connections with media professionals to make the most impact in today's attention economy.

In this week’s Up Arrow Podcast episode, William Harris chats with Phil Rosen, the Co-founder and Editor of Opening Bell Daily, about the art of corporate storytelling and influence. Phil shares editorial strategies, the importance of media relationships, and the essential elements of personal branding.

Resources mentioned in this episode

Quotable Moments

"Stocks always go up — on a long enough timespan, it's a reliable north star."
"If you don't believe things will get better, then you're not going to convince anyone else they will."
"Once you get one press article, that becomes your pitch for your next one."
"People want to follow people, not corporations."
"Reading books gives you a moat around yourself in this attention economy."

Action Steps

Cultivate relationships with journalists to increase your chances of getting press coverage for your business: Phil Rosen emphasized the importance of personal connections for attracting reporters' attention.
Produce a high volume of content to refine your brand message and engage your audience: Phil's success in journalism demonstrates the effectiveness of consistency.
Optimize your pitch emails with compelling subject lines and concise messaging to stand out to busy journalists: Phil discussed how to cut through the clutter in a reporter's inbox.
Leverage the power of reading to improve focus and broaden your knowledge base: Phil believes that reading is the antidote to the distractions of the modern attention economy.
Update and promote your personal brand by showcasing the behind-the-scenes process and the “why” behind your work, as Phil's approach to sharing his articles on social platforms suggests.

Sponsor for this episode

This episode is brought to you by Elumynt. Elumynt is a performance-driven e-commerce marketing agency focused on finding the best opportunities for you to grow and scale your business.

Our paid search, social, and programmatic services have proven to increase traffic and ROAS, allowing you to make more money efficiently.

To learn more, visit www.elumynt.com.

Episode Transcript

Intro 0:00

Welcome to the Up Arrow Podcast with William Harris, featuring top business leaders sharing strategies and resources to get to the next level. Now let's get started with the show. Hey everyone. I'm

William Harris 0:16

William Harris. I'm the founder and CEO of Elumynt and the host of the Up Arrow Podcast, where I feature the best binds in e-commerce to help you scale from 10 million to 100 million and beyond, as well as help you up arrow your business and your personal life. I'm excited about the guests that I have today. Phil Rosen. Phil is an award winning journalist and author and the co founder and editor of Opening Bell Daily. He quit his job as a senior reporter at Business Insider to launch the new venture. He's also the creative journalists club, hosting dinners and events in New York City for reporters, writers and editors, and he also runs a popular blog on personal growth and careers. Phil, welcome to the show.

Phil Rosen 0:51

Thank you so much, William. It's great to be here and excited to dive into whatever we dive into.

William Harris 0:58

Yeah, I always like talking about who introduced us in a lot of these episodes. And what's interesting is nobody introduced us. We introduced ourselves. Or rather, I reached LTU, because I'm a big fan of at the time, it was, I think, called, wasn't Opening Bell Daily? What was it 10 things before the Opening Bell? Right? Yes,

Phil Rosen 1:18

that was business Insider's old newsletter, which they shut down about a year ago.

William Harris 1:23

Yep. And I was very sad when they shut that down. I reached and that's basically, I think, when I reached out to you, I was like, Wait a minute. No, you can't shut this down. This is my favorite. This is one of the only daily newsletters that I actually open and read every single day. Please don't do this to me. And so I was very happy when you launched Opening Bell Daily to get me back into this, yeah.

Phil Rosen 1:42

I mean, I think that was a great experience for me writing, you know, mainstream newsrooms daily newsletter, and that gave me, sort of the tools and the know how and the confidence to launch an independent one. And, yeah, so far, you know, I think this week marks Week Six of the new newsletter, so we're really in the early stages. And yeah, read a response has been great so far. So that's been really exciting.

William Harris 2:10

I love it. So today we're going to be talking about market trends, pitching journalists, editorial strategy and personal branding. And my hope is that when you finish this episode, you have a better idea of how to use these strategies to grow your business before we get into that. Though, I do want to announce our sponsor. This episode is brought to you by Elumynt. Elumynt is an award winning advertising agency optimizing e-commerce campaigns around profit. In fact, we've helped 13 of our customers get acquired, with the largest one selling for nearly 800,000,001 that ipoed recently. You can learn more on our website@elumynt.com, which is spelled Elumynt.com, Okay, onto the good stuff here. Phil, I know that you don't consider yourself to be an expert on markets, and so you're very careful about that, and I appreciate that, because a lot of journalists may not do the same thing, but you've spoken to so many experts on markets over the years now, now at least, wanted to pick your brain about some of the things that you have learned. And let's start with maybe, are there certain charts or or places that youth would say, if somebody is running a business, e-commerce business, and they want to stay on top of what's going on in the markets, aside from subscribing to your newsletter, what are a couple of good charts or places that they could go to?

Phil Rosen 3:28

So I would say reading widely is the best thing I've done to really learn about markets and finance and the economy. Pretty much every morning I read the Wall Street Journal, Bloomberg and the Financial Times pretty much cover to cover, and that, you know, that's been like, years of that so that, you know, I am a journalist, so I wouldn't position myself as a financial expert, but, yeah, you pick up a lot of things by reading everything all the time and and, you know, for my job, I Write about it every day too. So that's the synthesizing of all that information I read all morning. So I would say diversifying your sources of information is just critical, as far as learning the markets and understanding it from you know, whether it's interest rates or the stock market, or even, you know, if recession indicators are flashing, these are all things that are probably good to be aware of if you're running a business, but also if you're an investor or an advisor of some sort, yeah.

William Harris 4:36

How do you stay bounced? So I know that you said that you're reading a lot of different sources, and every given day, I can see significant articles that are saying, This, is it ready for the apocalypse. And then there's, you know, the bulls that are on the complete opposite side saying, like, Nope, we're here Bull Run. Let's go. How do you find and weed through all of that to really have a. Would say a really good balanced perspective in your newsletter.

Phil Rosen 5:03

Yeah, I think a lot of the balance comes from talking with pessimists and optimists. So something I try to do every day, I make a lot of phone calls with sources, and those include, you know, economists or strategists at banks, investors, and usually I get a good sense of what I want to say in my newsletter because I talk to people that are very bullish on, you know, whatever the day's news may be. But then there's also the sort of perma bears who, no matter what the data or the stock market or whatever is doing, they will say, we are on the brink of a catastrophe. And, you know, I will say for myself, I am, yeah, I'm definitely an optimist. I believe things get better. And I think the Yeah, the sort of, the long zoom out, the long road of history, always tilts upward. And I think that's true in markets, you know, especially, I think stocks are the most obvious example. Stocks always go up. That's pretty much, you know, on a long enough time span, stocks will go up. And to me, that's, that is an easy enough north star to write from. And, you know, that's maybe simplifying it a little bit. But I think generally, if you Yeah, if, if you want to understand the market coming from a place where, okay, if I just stay put and be patient, things will improve. I think that's a very good thing to know as a starting point, but also something to aim for.

William Harris 6:39

Yeah, that's such a good, let's say analog or corollary to the DTC space here as well. And so this being one of the episodes where I'm using a lot more lateral thinking to kind of bring other thoughts into our world. One of the ideas there's, like you said, the perma bears. We have those in ad buying as well. There are perma bears who, every morning, you're convinced that Facebook ads is going to collapse on itself and will never work again, and and it's funny to kind of read and watch that, and then you've got, you know, the other ones who are perma bowls. And it's like, just set it and forget it, and don't ever think about it again. And wading through all of that nonsense sometimes on Twitter. X is, is always interesting. And so I think that you're right on the money there with that and being able to wade through that, yeah.

Phil Rosen 7:29

And I think also it's not in, it's not necessarily in your, your or your business's best interest to be a pessimist, because why are you what? What would you have to strive for? Then, if you're not optimistic things will get better, and whether that's advertising or sales or even, you know, just your business operations, if you don't believe things will get better, then you're certainly not going to convince anyone else things are going to get better.

William Harris 7:59

Yeah, no, that's wise words. So let's get into the more the meat here editorial strategy. You You've written over 2000 articles on business insiders, so you've done a lot of editorial strategy here. I hesitate to call it this, but I can't help myself, because it's morning and I'm a dad. What is your philosophie on Edith strategy.

Phil Rosen 8:24

For starters, I think volume wins over time. So if you you know I've talked to folks, they say, Yeah, I'm launching a newsletter. And then they tell me they're gonna publish once a month or twice a month, and then to me, that just says, okay, so you're not really launching a newsletter. You're going to write Occasionally, some like, you know, when you feel like it. And that is, that's the opposite of a strategy. I think, I think a strategy involves high volume and high reps, because if you don't go through that, you won't even know what your product could look like or what it could be at its best. You know at its fullest potential, because you get to your fullest potential through volume. And you know, I think that applies to podcasts or newsletters or running a news site, volume will win over time, because you will get to your end goal faster, as far as learning what your readers want, and learning what you want your brand to be and how you can deliver on your brand promise. So that's, you know, again, I I'm a pretty I think I'm a pretty simple person. As far as like, okay, the best approach is just going to be outwork. And, you know, outwork everyone else through volume and each individual article or piece. Of course, you want to make it as good as possible, but if you focus on, you know, the long game and try to show up every day, I think that's just. Such a winning strategy. And you know, this applies to way more outside editorial strategy, but especially with editorial strategy, it's pretty hard to be someone that never stops showing up. Sure,

William Harris 10:11

I think there was a study done about that. I don't remember where I read this. I want to say it was in the outliers book by Malcolm Gladwell, where he talks about that, right? Where there was, essentially they were given two tasks, or two teams were given a task of coming up with something really great. I don't remember what it was, so I apologize, pottery one, right? It might be, it might have been pottery, yes, so okay, maybe you tell it, if you remember it a little bit better than

Phil Rosen 10:37

I do, I think I've heard it. It might have been outliers, but I think I've just seen it elsewhere too. You had one team that they said, Okay, you have 30 days to make the one perfect pottery item. And then they were set off to do it. And then you had another team. They said, You will make as many pottery items as possible in 30 days. And on the last day, that's going to be the one you're judged on. And I think in the story, or the anecdote, the one team that did the volume, high volume, their last product was better than the team that just did one for 30 days trying to refine and perfect it. And, yeah, that totally captures what I think is the winning approach to, you know, building a website, building a news outlet, you know, building a newsletter, podcast, whatever it may be, it's that the reps will, the reps will smooth out your, you know, inadequacies over time. Yeah,

William Harris 11:35

and I, I agree with you. I'm doing the podcast once a week. And I'll admit, once a week podcast still feels like a lot of a podcast. If, if somebody is listening and they can't quite get to you know, your daily habit of launching a newsletter or something like that, is it worthwhile for them to at least start doing set a goal once a month, twice a month, wake that up to once a week? Is that? Is there benefit to that? Or is it like no you really need to just, if this is a thing, commit and go.

Phil Rosen 12:04

I think you can commit to go on like a sliding spectrum sort of so let's say you can only do maybe once a week, or once every other week. That's still better than nothing, I would say, but you shouldn't. I would say, ideally, you're aiming to ramp up over time. And maybe that's a better way of putting it like you can't go from zero to seven days a week usually. But if you go from you know, if you're aiming for once every two weeks, the aspiration should be to not stay at that level for too long, because I think it's really hard to build momentum unless you're doing a high volume of work. Because, you know, let's say what you could do in a year with low volume, you can do in three weeks at high volume, or something like that. And you're the distance between like a rookie to like a proficient level. You can just shrink that so dramatically if you lean into high volume. So I, you know, that's what I did with my own blog for a lot of years. It's what I'm doing with the newsletter now. Like I feel like, you know, six weeks into Opening Bell Daily, I really think every single edition has gotten better than the day before, and that's been, you know, 30 something editions already, and we just launched. It feels like yesterday. We just launched. And to me, that's, uh, that's my latest indicator of, okay, volume is such a winning strategy,

William Harris 13:37

yeah. So you mentioned momentum too. And I want to come back to that. But before I do, there was something else you were talking about here, which is just that idea of again, going back to volume and being able to do this multiple times. I think that's one of the allures on why I like the agency. And so this is a plug on agencies versus in house on a lot of things. This is not always true for everything. And just to clarify for anybody listening, I never worked at an agency. Prior to starting an agency, I was only in house and so but one of the benefits that I see is by the time you've run 10 tests in house, we've run 100 tests across 100 different clients, and in that amount of time, we've learned so much more about what's working on these ad platforms. And so I do think that to your point, there's a lot that can be learned in volume that just can't be learned when you're trying to be too perfectionist about something.

Phil Rosen 14:30

That's such a good point. It's also if you're doing 100 tests across 100 clients, those are, you know, in theory, 100 different voices. You're using 100 different models or formats and, yeah, that's even to me, that's almost more interesting than doing 100 reps of the same newsletter. Doing 100 reps for different people from one agency is pretty Yeah. I mean, the improvements must be radical over time.

William Harris 14:57

Yeah, yeah. So coming back. To momentum, though, that you said, I like that. You talked about this being editorial strategy, being a thing of momentum, where it gains and gathers like a snowball effect. And that's a lame thing to say, but it's just, I can't think of a better way to say it. It. One thing that I've noticed with some people, especially in e-commerce, and this could be in SAS as well, is the desire to capitalize on their blog, newsletter, whatever, too early. Would you share this sentiment that you see people sometimes trying to capitalize too early on some of these things, versus letting it gain the momentum and start getting the exposure and the Reach in the follows and the shares. Do you think that would be done at the same time?

Phil Rosen 15:46

I mean, I think, if you're running a business, I think content is like the flywheel for that business, you know, depending on the business, of course, but for many businesses, content is sort of like a top of funnel that you can bring business in from. But also, I don't think it's like, it's very hard to equate that to being a revenue driver. Let's say, yeah. I mean, if you, if you're putting a lot of time into content early, I don't think it can hurt, but I do think there's limited upside based on, you know, your your audience might not be there yet to appreciate that volume of content, but then, you know, sort of a catch 22 the volume is how you get new audience and get eyeballs. So, yeah, I don't know that's not a very coherent answer to your question, but maybe you could try saying it again, and I can try repeating an answer to

William Harris 16:48

I think it's perfect. I think what I've seen is sometimes people try to, let's say, capitalize a blog too early. And there was a trend where the idea was, let's say, gating some of the content too early versus just getting the content out there. And I felt like, when I would see companies do this, it would stunt their growth of the actual blog or whatever they're trying to grow at that time. Like if I started gating, you know, the podcast, versus getting it out there for free. It's like, Sure, then maybe you've capitalized on it, but you never gained the reach or exposure that you wanted to. And so I guess a better question would be, how do you continue to build that momentum? What are some of the tips and tricks that you've used to take from zero to 100 to 1000 to 10,000 and maybe it's even fast, but that concept,

Phil Rosen 17:39

okay, so I see what you're saying. I think there's definitely a danger of paywalling things too early, like as far as a podcast or a newsletter, because I think if you don't have the trust of an audience yet, why would they pay so you have to provide a pretty, I think, sizable amount of content that a reader will know they like, know they learn from, or know that they're entertained from before they're even willing to consider paying for anything. And then that doesn't even touch on, like, you know, what price point will people most be willing to pay at and all that? But I think there is a, yeah, yeah, there's a huge upside of publishing a lot of free content, because that's how you Yeah. I think that's how you win early trust. And then the early trust is the momentum, because if someone really likes a newsletter, for example, they will tell a friend, or they'll post it on Twitter or LinkedIn or something, and when everyone can click and not hit a paywall, I think that's just a huge you know, these days, it's kind of a sigh of relief. And you know, something that I think a lot of news outlets are running into now is the writers can't really share their own work without people asking them to, hey, can you screenshot your article for me? Because I can't get around the paywall. And I don't know if that's I think that's really hard to keep momentum when that is the case, because if all your writers can't even get their own work in front of friends and family. What does that mean for the bigger business, or, you know, the brand, if no one's reading their work, other than the super fans, because then it's, yeah, if only your super fans read the work, and then everyone else is kind of gated out of that, I would guess it's harder to grow from that. And, you know, there's, of course, there's different ways to slice it and nuance it, but that, that's what a that's what it seems like right now.

William Harris 19:52

Yeah, there's two other things on editorial strategy that I really want to touch on. One would be learning from your. Audience and how you're going about that. And I'll start with that one, but the other one that I want to make sure I say so we don't forget, is how to continue to grow that audience in ways that you're using to do that. So let's start with first, how are you learning from your audience? You know, I think about this from the podcast perspective. I think it's a little bit maybe potentially easier in the newsletter space, because you actually have their email address, you can email them, but if I wanted to learn from my audience what they love and don't love, you know, just in general, what are tricks that you're using for learning from your audience?

Phil Rosen 20:33

Yeah. I mean, I think with a newsletter, the feedback can be pretty immediate, and, you know, similar with if you're writing articles on the internet or on a news outlet and you're seeing a comment section kind of blow up, then you must have hit a nerve with something, whatever you're writing that day. So that's sort of an immediate feedback and same with YouTube videos too. You can see comment sections and how people respond, but in a newsletter, specifically, you know, some days I'll get a million responses to the newsletter, like people hitting reply and putting a note in, saying, like, Hey, you were, you know, maybe you missed the mark that day. Or, like, I really liked how you said this or framed this, or this really helped clarify something. And then other days, yeah, radio silence, you send a newsletter out and no one says anything, and maybe it's like, it's more likely it wasn't good rather than it was perfect. I would like to think that when no one says anything, Wow, that must have been a perfect addition. That's probably not the case. So yeah, that kind of signal is helpful, I would say. And you know, sometimes it comes down to your subject line in a newsletter, like maybe fewer people open it, and that means fewer people responding or clicking, whatever that may be. Or some days, I can check Facebook or LinkedIn and see how many people shared the newsletter that day on their social channels. And if, yeah, if I nailed a newsletter one day, then more people will share it. And I can, that's how I know if the newsletter was, you know, if it resonated or not. And your second question, can you say that again? Yeah.

William Harris 22:15

And so the second one, then is, and I think you're almost hinting at this, sharing being a big part of this. But how do you consistently grow that audience? Because I imagine you're not just writing it and saying, Hey, I hope they all start listening and reading to what I'm saying. You're doing things intentionally. Yeah,

Phil Rosen 22:29

I So, something I've learned being in sort of mainstream news for a few years. If you do not promote your own work, then no one else will typically, like, that's, you know, sometimes a little bit, but really, you have to be the driving force of getting people to pay attention to your work, because everyone has such limited time and attention, and there are infinite news sources or social media apps that are pulling that attention. So if you don't try to raise your hand even a little bit, then no one's gonna find you. So you know, when I was at Business Insider, if I wrote 2000 articles, I probably made at least 1800 LinkedIn posts about those like I was sharing almost every single article I wrote over several years, and definitely, yeah, at some points, it probably felt like too self promotional to some people. But then also, it's like there were, I'm sure there were so many readers that only found my work, not through Google or Business Insider, but because I was sharing it on my own personal channels. And I think that's important, and a lot of that is that compounds over time, because, you know, if I share an article on Monday and then 150 people see it, maybe on Twitter, then I could share the same article Wednesday, and maybe 25 of the same people see it, but then a new 50 people see it. So you can really, you can reshare a lot of the same content over and over and with social media like it's so it's kind of this black box algorithm, but you're almost certain to run into new audience every single time you share something. So if you do that regularly with all your content, you know, for me, I'm publishing five newsletters a week right now, and if I post each one twice, then that's like 10 social posts a week. And I've already done the work in writing the newsletter, and I just have to write a little blurb or repurpose it for LinkedIn or x and that. So I would say it's like the consistency in sharing and raising your hand is important if you want to get eyeballs in the sort of this era.

William Harris 24:54

No, I think that's very important as well. And I do want to get into some of that personal branding. Stuff, then a little bit later as well, I think it would be impossible to have a conversation about editorial strategy without talking AI in some fashion. One of the things that I remember you wrote is that you're not a big fan of AI, that you called it the opposite of the printing press, but you didn't call it the but, like, it's, some people have said it's almost like the printing press, like the modern version you're like, is it's the opposite. What do you mean by AI being the opposite of the printing press?

Phil Rosen 25:32

I think the printing press democratized information, and more people were able to read, and if you created something, more people were able to see what you created. But now, if everyone relies on something like chatgbt, and then everyone relies on also like some type of large language model to analyze that work that is being distributed by AI in the first place it's everything becomes so derivative. So if the content that's being produced is AI generated, and then the analysis that's being consumed of that content is AI generated, the pool of information actually dwindles so dramatically, I think, like it would proliferate as far as total volume, but maybe books become paragraphs, and then that's what people read moving forward. So, yeah, I mean, it's not a great I don't know if that's the best, uh, analogy I used, as far as the opposite of the printing press, but it's so I don't have a problem with technology or like the the amazing AI tools that are coming out. But I do think there's a huge risk that everything becomes so unbelievably derivative, and we start consuming only derivative products and writing that doesn't seem good, because if you you know, if you read a book, you are probably immersing yourself for eight to 10 hours in the author's you know, in some cases, the author's life's work, and that takes you, let's say, eight hours to read took the author years to write, maybe. And if that dynamic changes to your reading, AI generated summaries of a book. Then, you know, and even maybe the book at some point will start being AI generated too. Uh, absolutely, you're not getting the depth of of knowledge. I don't think, um, but then at the same time, the people who choose to continue reading books and maybe not relying on AI generated reports about a book. I think that's a huge advantage moving forward. It's like, yeah, it takes a little more time, but the grasp of concepts and stories and the skill that comes with that, I think, is going to be more and more important, and it's going to be a bigger distinguisher moving forward, like, if, yeah, if you have the focus to read a book for 10 hours, that, as it is today, is like dwindling so fast, like books is, books are becoming, I think, sort of this, like antiquated medium, which makes me sad, because I've written two books, but, yeah,

William Harris 28:23

I hadn't thought about it like this, but I like where you're going with it, even though it is a bit dystopian, right? But it's almost kind of like, reminds me of Wally, the movie, a little bit, where everything is almost just thought for them, and they're like, oh, blue. Blue's the new red. You just click it, and they've all got this, you know, blue suit on now, because your point, yeah, I hadn't thought about how that would shape the future, but we need to be intentional now about making sure that we're still creating absolutely original thought.

Phil Rosen 28:55

Yeah. I mean, did you see there was a clip of one of the dating app executives yes a week ago, saying, like, the future of dating is going to be our AI, dating other AI, yes. And it's like, where is the intimacy there? Or where's the risk taking? Where's the the soft skills and, you know, sort of the excitement of like meeting someone for the first time, or cold approaching in a new place like all that. If that all goes away, I don't know if that's to our benefit, right?

William Harris 29:26

I did see that, and that is, it's just weird. I met my wife the old fashioned way. Actually, we met on a trip. Basically, we met on a missions trip in Kentucky. We were there helping with this camp. And I mean, that's, you know, just what a great way to be able to meet somebody in person. Yeah,

Phil Rosen 29:44

I'm replicating that. So, no, no,

William Harris 29:47

I want to transition into getting press. And so you've been on the other side of this. You, you've obviously covered a lot of people. You've quoted a lot of people. What are. Are tricks that people can use to get more press for themselves, for their business, etc.

Phil Rosen 30:07

So I would say meeting journalists is a great starting point. And I think that kind of goes with the idea build the network before you need it. So if you are someone that happens to be friends with a lot of journalists, that's pretty cool, because those are the people that will, yeah, that's the press essentially, like that you will be pitching, if you one day have something to pitch. So on a very basic level, like, going out of your way to like, meet and like, just get to know some journalists. Never hurts. As far as pitching. You know, when I was at business, insider, my inbox probably had 150 emails a day that were, yeah, pitch story pitches from PR people or individuals wanting to share their own story, or their own company, or people raising money, whatever it was, and it's very hard for one person to go through all of that, you know, read all of it for one but let alone cover it in articles so and also the so many of the emails that I didn't recognize the sender, I would immediately archive because I just don't have the bandwidth to cover it. But then when I do recognize the sender, like maybe it's a individual, like a founder or a PR person that I've met in person, I'm way more likely to give it a thoughtful read and response, and that doesn't always mean I'm writing about it just because I know them, but I'll at least read it and I'll know who exactly is sending it to me. So a lot of this is relationship based. But if you want to get into the like, the nuts and bolts of a like pitch email, I think there's a couple things there. So a subject line is huge. I open a lot of emails that say, like, your post on LinkedIn, or like, I saw your specific article about this, or I saw your tweet about this. Like that gets my attention, because then it's someone I know is not mass emailing, and that's a huge like, instant delete if I see a mass email, especially if it says, Dear reporter, slash editor, that's the worst. And you know, so I immediately delete those. Or, like, you'll it's amazing how many PR people send emails with the wrong name. So they'll say like, you know, Hi Jeff or something, and I'm, you know, I'm Phil, and I just don't, I don't even read past that if they get the name wrong, because then I know they haven't looked at my prior coverage, and they don't know what I write about. But also, if you see a subject line, if journalists see a subject line, at least for me, that says, like, shocking stat, or like, you won't believe. Like, you know, some said sensationalizing in the subject line pretty much instant delete, because it's usually not that shocking. If they have to say it's shocking, it's not going to be that shocking. And then in the body of the email, what I recommend is really short and to the point. So when I help people craft pitches like even, and this is the same, if I want to pitch as a freelance journalist to editors, my pitch is like two sentences, and I really try to nail like, Okay, what is the story? And why am I the person to tell it? And if you can get those two things into two sentences and then say, you know, and then sign off from there, that is really effective, because the person you're writing to, yeah, they probably have over 100 pitches that day. So I think reporters appreciate when you're very brief, because it shows you're not wasting their time. Like, if I get an email that's four paragraphs long and it's a pitch, there's almost no shot I'm reading the whole thing. So that's yeah, just don't have the bandwidth for you. So

William Harris 34:18

I got a treat for you. I'm gonna have you grade what you think about my pitch that I wrote to entrepreneur this Okay, the first time I really cracked into I used to write a lot more than I do now, and wanted to write for entrepreneur, and so I sent this pitch to the editor. Here my subject line, another boring pitch from a mediocre writer. I love that, dude. Okay, good. It's

Phil Rosen 34:43

contrarian. I mean, because no one would say that. So that's okay. I like that a lot, actually.

William Harris 34:48

Okay, um, what's funny about and that's kind of what I was trying to get into the mind of who's reading this. I kind of assumed that they were doing the same thing where they're like, man, they they probably get, you know, 150 these a day, and it's like. How do I skate through that a little bit, I will say this is what entrepreneurs said to me. The editor wrote back. He said, What are you thinking with that subject line? I'm not reading your pitch. Okay, at least he replied. So I was like, All right, I got a chance. I replied back. And I was like, Okay, here's why I said that. And he said, Okay, you've got another chance. Send it to this person. I'm actually not the one who's in charge of this piece of that anymore. So I got another chance. That's

Phil Rosen 35:25

amazing. That's incredible. Yeah, yeah, because I if you, if you don't try to sensationalize, but you're also contrarian. I think that's a pretty powerful combination, and I've never really thought about that till we're talking about it right now, but that's a great yeah, I love that. I might have to steal that for future pitching workshops

William Harris 35:48

and then. So let's just say that they do have something to share. I think one of the things that you called out, that I appreciated, aside from this, is it's not just about having something newsworthy. Why you I think that's maybe something that a lot of people, I would imagine, Miss from their pitches, or maybe they'd have too much from this if you had to wait the two pieces. Is it that people just send you pitches that have something that's just not worth pitching, but they have a good reason for why them, but just not pitching? Or are they pitching something good, but they didn't really qualify by them. Which one do you say is lacking more?

Phil Rosen 36:27

That's good question. I think it really depends. But I will say, if I get a pitch that says, you know, like, let's say So this week, there's a lot of meme stock activity, and if someone pitches me about talking about GameStop, for example, shares of Gamestop going up and down, and they just say, like, this person can speak to like, why trading volumes are so crazy, why the stock is going wild, whatever. But then they don't tell me, like, I have to know why they're the person to say those things, because you and I could say those things too. We could talk about why the stock's going up and down and, you know, so could anyone at the local grocery store, like, it's all, like, anyone can say anything, but if there's no context behind like, Okay, what gives you the expertise. So for example, if, if I say, Okay, you should just put your money into the s, p5, 100 every year and let it compound for decades. That isn't that interesting, and that's not that relevant to anyone, because I'm me. But if Warren Buffett says it, and he does say it. Everyone's like, oh my goodness, that's the greatest strategy of all time. But it's because he is Warren Buffett, so it's like that holds huge weight in a pitch, as far as delivering who, delivering the context on why this person is right for a certain interview or a certain commentary. Because otherwise, anyone could, you know, it's like the words and the comments are important, yes, but I would say it's more important to know who they're coming from.

William Harris 38:13

So have the right subject line, get their attention, have the right pitch, have something in there from a context standpoint, but then ideally have a relationship. And I think that that makes so much sense, because I'd say that's true in my own inbox as well. What about things like hero, for them, against them, Help a Reporter Out, H, A, R, O, have you ever used them? You might have to explain a bit more. So. So there are services out there where some journalists will post that they're writing about something on what's called Help a Reporter Out H, A, R, O, and then, like, you can, like, submit something like, Hey, I've got something to share to that. Do you feel like that is actually beneficial, or is it just better to just get to know the reporter, and if get to know the reporter out.

Phil Rosen 39:03

Okay? So I do. I am familiar with this, but I've never used it, so I don't know what that means, but I, for one, I've never used it. I would say if, if a reporter is posting something, then they're definitely more inclined to respond because they're doing like a call out for for sources or experts. I'm very much a relationships guy, so I would always opt for that rather than a cold message or a cold email, even if it was an outreach. Yeah, I'm not sure if I have too much to say on that, just because I personally don't really use those platforms.

William Harris 39:47

Yeah, I don't know. So, so then my there's a another episode here. Katie Richardson was on here, and she got a lot of press, and one of the things that she said that was helpful for her. Was starting locally, and then that, you know, compounded itself into bigger and bigger opportunities. Would you say that that's a good strategy, or just go for the big ones?

Phil Rosen 40:10

I think that sounds like a great strategy. I always have the mindset. It's like, once you get one, that one, you know, if you get an article in Business Insider, that Business Insider article becomes your pitch for your next one. So your pitch gets easier and easier each time because you have sort of more like ammo in the tank. You can say, look, Business Insider already covered me, so now Hey Forbes, or hey, Fortune TechCrunch. Like, you know, the cell is way easier because you're sort of vetted by another newsroom and and also, there's a bit of FOMO. When a reporter sees that, if you know, they see someone's been interviewed by a top outlet, then they're like, Wow, we should also interview them, because then we can kind of share that clout, or, you know, share the story, whatever it is. And I think a lot of founders or business owners try to pitch too many places at once, so they'll try to go for the five or eight biggest news outlets, but my suggestion would be just to go for one, and then if you get one, that one becomes your pitch to everyone else. So I think it's easier to sort of, yeah, if you ramp up after the one. That makes a lot of sense. What about I

William Harris 41:39

want to jump over into the personal branding side of things then too. And you touched on this a little bit about how maybe it can feel self promotional to promote your own stuff, but you have to do it. And that's one of the best ways people find you. A phrase that you use, that I liked, is you have to write yourself into the job you actually want. What do you mean by that?

Phil Rosen 42:01

I think it's a lot easier to show people what you can do or that you deserve something if you've been doing it for a long time already. So you know, my first newspaper job, I had zero I had no journalism background. I had no formal internships or experience, but I started a blog online that very few people read, but I wrote, you know, 60 or 70 essays on it, and then someone did notice it, and that's how I got my first job in a newspaper. All those blog posts and articles were free, and, yeah, very few people read them. I didn't make any money, but because I've been doing the work for so many months already, and had so many reps under my belt when no one was watching, when someone did all of a sudden pay attention, I had a whole whole portfolio to share, share with them. And that was my first, yeah, sort of my first signal that, okay, if I just do the work, no matter who's looking I can, you know, maybe get any job I want, if I can just do it on my own and show the initiative and the passion and sort of The Yeah, like, the gumption to do this. So that's and I think over time, what that did for me. I think I almost have more of a reputation for writing a ton of volume like I think a lot of people know me through how much I talk about, doing the work and putting out a lot of volume of writing, versus almost any one topic I cover. So like, more than finance, or more than my books, more than my newsletter, I think people know me as just the person who writes a ton of stuff online. And, like, sure, yeah, for better or worse, like that is, I think, the case right now. But being known as someone who does the work is not, yeah. There are worse things to be known for. And if you're looking for a job, that's a great thing to be known for, because a manager or employer, they want people who have no problem putting their head down and working. And if you can do that before you get to that job, uh, chances of success just go up.

William Harris 44:21

So when it comes to personal branding, you're, if I'm hearing you correctly, it's less about even branding yourself as the expert of whatever the different things are that you're trying to do, but more about even just the journey along the way. Is that kind of what you're

Phil Rosen 44:38

saying? Not necessarily. I mean, I think it's the journey is great if you can document it and sort of show your work as you go, but you could brand yourself however you want. And I think you can that opportunity. You can just keep reinventing yourself, sort of, and I think if you have the work to back it up. Uh, you like it almost always, uh goes in your favor because the work is what will smooth over, sort of all the the doubts and the haters and people who say, like, Oh, you're being too self promotional, whatever it's like, yeah. Like, maybe you're being self promotional, but you have your 10,000 hours under your belt that you can show anyone you have your stack of evidence that you're not just being like you're not just shilling something a company or a product. You have so much evidence that you are the person that does the work. And that is super powerful, I think, and but something that to pivot for a sec on the personal brand stuff for journalists specifically, and I think there's, there's a tie here to business owners that you'll have to make for me. But when I write an article, let's say I'm writing an article about GameStop, I know there's going to be 200 other articles that day about GameStop, and most reporters, they will post the article and then a blurb about GameStop. But what I would do instead, and this is what I typically do, I'll post my article, but then I'll instead of writing about the article, I'll write about who I called, what my writing process was, why I picked the angle, I did, my thought process behind what's going on. So essentially, the story behind the story, and that, I think, is a super powerful lesson for personal branding, because if you're sharing an article or sharing content, most people already know what the thing is, but if you share the behind the scenes and your own personal process, I think that captures what I believe to be personal brand. It's like, Who are you and why are you the person to do this? And that's way more interesting to a lot of people than the actual like Gamestop article. So I just wanted to, like, sort of tie that into what I do myself. We

William Harris 46:59

love behind the scenes as a just human race, right? We love being able to take a peek behind the curtain and see what's going on. And I could see that being very valuable on LinkedIn posts and Twitter posts and whatever, to be able to say, here's the why, here's the who, here's the what. That's good. I want to get into why you quit your dream job. You had a job. National newsroom decided to go independent. It was your dream job. Why? Like, what was the thought behind that?

Phil Rosen 47:33

It was time to try something new and independent. And I also, I think I'm making a bet that media will continue to fracture more and more. So I've seen so many journalists that were excellent in their mainstream newsrooms that went independent over the last year or two, and they have had a lot of success, and they've had a lot of readers come to their sort of niche product or audience, and you can see this with the ballooning of the Creator economy. People want to follow people, not corporations. And I think social media has made that more possible than ever, and also more viable to make those audiences or products into real businesses too. So my sense is that media is sort of at this turning point, and it has been the last couple years where being at, you know, the New York Times or The Business Insider is now no longer the only way to get the word out about things you can build your own audience and sort of gatekeeping that distribution is no longer the case for these legacy outlets. So me going independent with a new, you know, sort of a new media brand is part of that bet I'm making, that media will continue to fracture legacy. Newsrooms will struggle to retain the eyeballs they've had for decades, and people will continue following people instead of companies.

William Harris 49:21

Yeah, I totally agree with you. We are a relational being as human beings, so we want that relationship with another human being. There's even a lot of research out there about mirroring, right, and how we mirror other beings, other animals, other animals mirror us. So it's harder for us to mirror corporations and to feel the same kind of connection totally.

Phil Rosen 49:50

It's also different. If you know the New York's time, the New York Times told me to do this, feels sort of condescending. But if it's. This person said to do this, that's a little more relatable.

William Harris 50:05

I like that. I love getting into the personal side of who my guests are as well. And so I want to have a little section about who is. Phil Rosen, one of the things we talk about is how to up arrow other areas of your life. And one of the things that you talked about to me, that you said that I really appreciated, was reading books is the antidote to everything wrong with modern society. What do you mean by that?

Phil Rosen 50:33

I think a lot of that just comes down to attention span. I yeah, I think if, if you can't focus, you don't have control over your own mind, and if you don't have control over your own mind, you're limited in what you can think about and what you can create. But reading is the ultimate focus tool. You learn and you study and you immerse yourself in someone else's life's work, and that is so sort of alien today, because most people are scrolling on on Instagram or Tiktok or Twitter, whatever it is, and you know, I'm guilty of it as well. I should read more, but if you spend more time reading books, you are sort of you're like building a moat around yourself in this, this attention economy, where our attention is so pulled and divided, but books demand your full attention. You can't be scrolling while you're reading, like you know, if you're watching a movie or a show, you can kind of still be scrolling, but a book, you really can't be doing that. And I think if more people read and more, including myself, we would be better at doing a lot of other things in our life. Yeah,

William Harris 51:49

there's a interesting comic by I think his name is Nathan Pyle, and he almost draws like these aliens that speak in this language that's kind of like English, but it's really like how we would speak if it was like a foreign idea or concept to us, and one of the ones that he has there shows somebody watching a movie, or it's a couple watching a movie, and one person is scrolling and then asking a question about the movie, and the other ones, the other beings, like, I mean, you would know if you are watching along with me. It's like, Yeah, but you're my best friends. You'll tell me anyways. But to your point, we can watch a movie and scroll and kind of be distracted, and that's very hard to do with a book. I know that you said that you're a big reader. You read, you know, the Wall Street Journal and a bunch of other things every morning, but that's for work. Are you reading? Then, for personal pleasure, for personal benefit, like and how much is how much are you reading?

Phil Rosen 52:41

Yeah, I I'm reading. I read a lot of books. For sure, books are my favorite pastime, you know, and and again, all this is not to say I never use social media and I'm never scrolling, because I do I, you know, and I'm trying to do less, but I definitely it's hard. So I do read books, though, and I read a lot of fiction. I love short stories, and I love classic fiction, the stuff that we all spark noted in English class in high school and but I also read quite a bit of business books, like I recently finished this book called the smartest guys in the room, which is from maybe 20 years ago, but it's about the fall of Enron, and it's just a great, compelling sort of, you know, corporate catastrophe story. And so I read a lot of, like, business narrative books, and a lot of classic Fiction in, you know, a few years ago, I went through a gazillion personal growth and self help books. I kind of went through a phase. So I read very widely. I would say, like, I try to sprinkle in history books as well, but I think it's the, I think a lot of what I can do as a writer and reporter comes from all these years of just reading books like I very much point to that as the bedrock to everything I do. So the reason I can write the way I write or perform as a journalist and reporter is because I've been obsessively greeting for so many years, and that's given me sort of this, yeah, maybe a Web of Knowledge I wouldn't have otherwise gotten from. Yeah, I don't even there's nothing that comes close, I think, as far as taking in information other than reading. So that's been a huge, huge way I've, you know, sort of bolstered myself, I think,

William Harris 54:44

yeah. I mean, that kind of reminds you of something else that you've told me before, which was that some of these things are less about the routine, more about the discipline and the habit, that the 10,000 hour rule is not a myth.

Phil Rosen 54:58

Yeah. Yeah. There's no if you do something long enough, you are bound to get good at it. And I think a lot of people give up before they see that come to fruition. You know, whether it's writing or podcasting or starting a YouTube channel, even sticking with the job as reporter, like these things, as long as you continue to show up for long enough like there's no way you can't make a success out of it, is what I think. And that really is like, Yeah, I think that, you know, the 10,000 hour rule, it's kind of a cliche at this point, but I think there's so much wisdom behind it, like the the message of it, I think, is, is important. And I try to, you know, if, if there are days where I feel like I aren't good enough at this one thing, or I don't know what to write about, or whatever it may be, then I always take a step back and I'm like, okay, in a year from now, if I just keep going, then I'll have I'll remember this day and like, it'll be kind of just like a blip, and it'll get smoothed over by all the Volume I've done since that day, and that's how, yeah, that's the only way to get better at things. I think with

William Harris 56:26

you 100% love the 10,000 hour rule. It's brutal, but true, and I can see that even in my own life, and it's it's only now that I really buy into it as I wish I would have bought into it maybe more when I was younger. But you know, the older I get, the more that I realize just how true it is. And something I try to instill in my kids as well as they're young and they're working on something, it's like, whatever you want to do, like you could be great at it, but, like, there's nobody that will be incredibly great at any one of those things, for the most part, without putting that in, it's like, whoever you want to model, right? And so it's maybe my oldest, you know, wants to be a singer or something. It's like Taylor Swift has put in at least 10,000 hours. Yeah, Taylor Swift, and that's true for every other person that you look

Phil Rosen 57:08

up to. Yeah, absolutely, there's no one. There's no one who reaches the top of their craft without doing that. You know, no one's taking shortcuts. That's, I think shortcuts are also such a myth, because, you know, Taylor Swift, or like LeBron, is not, you know, they're not taking shortcuts, or, like, faking their way to the top of the mountain. They are that good because they've worked that hard. And I think we can all do that at some scale in our own lives. Totally. Last

William Harris 57:43

thing I wanted to chat with you about is the creative journalist. But we talked about this a little bit. What is it in what inspired you to put this together? Yeah,

Phil Rosen 57:55

I created journalist club in February of this year. It's only a couple months ago, I noticed that media, including my own company at the time, was going through a ton of layoffs. I saw a lot of friends that were really talented lose their jobs, and layoffs can be arbitrary and brutal and have nothing to do with how good you are at your craft. And at some point I realized, wow, it'd be really great for everyone reporters, if we knew more people at other companies. And so I started hosting these dinners. And then they were, they are 10 journalists each, everyone from a different news outlet, and they're not work events, so no one's showing up online or, you know, we, a lot of journalists, know each other through press events or conferences, and we kind of see each other, or we recognize each other's bylines, but we don't really spend non work time together, and That's where you build those relationships and friendships, and I think in a lot of ways, you need that support system in as tough an industry as media. So yeah, so I created journalist club, and I've now hosted, in a little over two months, I've hosted 130 reporters and journalists editors at various events in New York City, and I have a bunch more events planned. And I think a lot of everyone I've spoke to who's attended an event has found it really rewarding to meet people doing the same job as them who work at different companies. And, you know, I knew something about my own experience at Business Insider. I knew everyone in my own company, but I didn't know, really, anybody who worked at, you know, the Wall Street Journal, the New York Times, Bloomberg, wherever it was. But now, through these events, I know a lot of reporters at every. Outlet that has a New York City presence, and that's been really special and inspiring for me, because I get to chat and meet and hang out with all these people who are great at what they do, and who are also just looking for meeting with, you know, meetings with people doing the same job as them. And that's been, yeah, it's some of the most important work I'm doing right now is producing these events.

William Harris 1:00:28

It reminds me of, let's just say, if I was gonna bring that back to e-commerce a little bit, one of the things that I tell new founders is do the things that don't scale. And this is a great example of that where this doesn't scale, like there's a limit to how much of this that you can do. But if you're launching a brand, let's say that you're launching a kids mitten brand, there's if somebody discovers your brand, they see an ad on social media, they buy it, they'll like it, they might love it, but it's completely different than the kind of love and rep that they want to give you if they met you and hung out with you. And you know, you've 10 people at a time here, there are these different events, and they're meeting you and hanging out and passing out the glove. They become fanatical fans about what you're doing and telling everybody else that they know. And so, you know, launching a brand, launching a newsletter, launching out anything that you're doing, one of the best ways to really jumpstart that growth and get that feedback in very real time is exactly doing what you're doing, put together some time to get in real life with people that you are, you admire, that you enjoy, that you want to be a part of.

Phil Rosen 1:01:37

Totally it's yeah, this. This is not scalable, and it's also some of the most energizing and fun stuff that I get to experience. So yeah, there's a yeah, there's a lot to take from that. I think,

William Harris 1:01:56

yeah, that's good. Well, Phil, I have really enjoyed learning from you today and getting to know you a little bit more. If people wanted to follow you, to subscribe, obviously as well. What's the best way for them to stay in touch?

Phil Rosen 1:02:10

Yeah, I my newsletter is called Opening Bell Daily, and it's free. You can Google it and yeah, hopefully subscribe comes out five days a week, and then on you know, if you look up Phil Rosen, you can find my Twitter and my Instagram, my LinkedIn. You know, I'm everywhere on socials, very easy to find. You can also find my books on Amazon. I have two books you type in Phil Rosen, they'll also come up there. So yeah, everything is just my name. You just look up my name, and then all this stuff will come up and take you to different corners of the internet. So

William Harris 1:02:50

that's brilliant. Thank you again for joining, sharing your wisdom, sharing your time with us today. Phil,

Phil Rosen 1:02:55

thank you, William. It's great, great to talk with you.

William Harris 1:02:58

Thank you everyone for listening. Have a great rest of

Outro 1:03:02

thanks for listening to the Up Arrow Podcast with William Harris. We'll see you again next time, and be sure to click Subscribe to get future episodes.

‍