How to get press for your product | Jason Feifer (editor in chief of Entrepreneur magazine) | Transcription

Transcription for the video titled "How to get press for your product | Jason Feifer (editor in chief of Entrepreneur magazine)".

1970-01-01T01:33:23.000Z

Note: This transcription is split and grouped by topics and subtopics. You can navigate through the Table of Contents on the left. It's interactive. All paragraphs are timed to the original video. Click on the time (e.g., 01:53) to jump to the specific portion of the video.


Guest Introduction

Jason’s background (00:00)

The editor, the writer, I'll just say it as plainly as possible, they don't care about you. They don't care about you. They care about their reader or their listener or their viewer. That's who they care about. That's who they're serving. And if you can be of use to them in sharing the kinds of information that they are looking to serve their audience, then you can get what you want. But you can't treat them like a service provider because they're not. And so you have to approach them with an understanding of what they're trying to do for their audience and how you can fit into that. Because if you you don't they are not interested in you today my guest is jason pfeiffer jason is editor-in-chief at entrepreneur magazine previously an editor at fast company and a number of other magazines he's also an author podcast host keynote speaker and startup advisor in our conversation we get incredibly tactical about how to get press for your product. Jason shares how to pitch a journalist, how to find the right journalist to pitch, what publications to consider, why freelance writers are more likely to write about your story, why the mission of the publication is so important in how you pitch them, plus what channels to use to reach out to journalists, how to think about your goals and what success looks like from getting press. So much more. I learned a ton from this conversation and if you're looking to get press for your stuff, you will find so much value here. With that, I bring you Jason Pfeiffer after a short word from our sponsors. This episode is brought to you by Sidebar. Are you looking to land your next big career move or start your own thing? One of the most effective ways to create a big leap in your career and something that worked really well for me a few years ago is to create a personal board of directors. A trusted peer group where you can discuss challenges you're having, get career advice, and just kind of gut check how you're thinking about your work, your career, and your life. This has been a big trajectory changer for me, but it's hard to build this trusted group. With Sidebar, senior leaders are matched with highly vetted, private, supportive peer groups to lean on for unbiased opinions, diverse perspectives, and raw feedback. Everyone has their own zone of genius, so together we're better prepared to navigate professional pitfalls, leading to more responsibility, faster promotions, and bigger impact. Guided by world-class programming and facilitation, Sidebar enables you to get focused, tactical feedback at every step of your journey. If you're a listener of this podcast, you're likely already driven and committed to growth. A Sidebar personal board of directors is the missing piece to catalyze that journey. Why spend a decade finding your people when you can meet them at Sidebar today? Jump the growing waitlist of thousands of leaders from top tech companies by visiting sidebar.com slash lenny to learn more. That's sidebar.com slash lenny. This episode is brought to you by Maui Nui Venison, a mission-based food company bringing the healthiest red meat on the planet directly to your door. I actually joined Maui Nui Venison earlier this year after hearing their ad on the Tim Ferriss podcast, and I'm excited to be spreading the message further. Not only does this company provide the most nutrient-dense and protein-dense red meat available, their operation produces the only stress-free, 100% wild-harvested red meat on the market that is the only one of its kind in the world, actively managing Maui's invasive axis deer populations, helping to restore balance to vulnerable ecosystems, food systems, and communities in Hawaii. Also, it is seriously delicious, not at all gamey, and easy to cook. My wife and I made stew and steaks and all kinds of grilled goodies with the meat. We also feel great about it as a protein from an ethical standpoint. I highly recommend trying their all-natural venison jerky sticks for an optimal protein snack, as well as a wide variety of fresh cuts, all available in their online butcher shop. There are limited memberships available, but you can sign up and get 20% off your first order at mauinuivenison.com slash lenny. That's mauinuivenison.com slash Lenny. That's mauinuivenison.com slash Lenny. Jason, thank you so much for being here and welcome to the podcast.


Press Coverage Strategies For Startups

Jason’s inbox volume (04:09)

Lenny, thanks for having me. It's absolutely my pleasure. We've actually collaborated on a couple things recently. And as we were chatting about some stuff, I was asking for advice on how to help a startup. I'm working with get press. And you shared a bunch of killer advice. And so I asked if you could just come on this podcast and share some more advice for how to help startups get press. And here we are. Yeah, I'm really happy that you asked me to do that. This is something people ask me about a lot. I've been in media for decades. I've worked at a lot of different magazines. Obviously I I run Entrepreneur Magazine now, but I was at Fast Company, I was at Men's Health. So I've seen a lot of different sides of media. And it is a very misunderstood tool, particularly for people in business. And so I love demystifying it. Amazing. I'm excited to learn all this too. And so thanks for doing this. Yeah. Amazing. I'm excited to learn all this too. And so thanks for doing this. First I'll have, I don't know, I mean, it could be anywhere from like 30 to 50 pitches in my inbox. It comes all day. Now, to be clear, most of that is garbage in the real garbagey sense, right? It's a lot of completely unrelevant press releases that were sent to me and a bazillion other people. But within there are definitely some people who have spent the time to reach out very sent to me and a bazillion other people. But within there are definitely some people who have spent the time to reach out very specifically to me. And everybody in media gets some kind of volume like that. To reach out to somebody in media is to be shouting over a lot of noise. Wow. I imagine we'll get to this later, but I'm curious just what percentage of those are PR people and press releasee versus like a founder or someone that is like, you know, doing it themselves. The percentage of direct messages from founders that I'm getting is low. I would say probably 20, 25%. And then the 75% is PR in some capacity, either targeted PR where somebody's intentionally reaching out to me or mass blast press releases. You know what's crazy is I've been getting a lot of these now. People think I'm some kind of journalist and they're just like, embargoed announcement, product launch. It doesn't take much because you just end up on some list. And what's really interesting, and we'll talk about PR later, I know, but one of the great insights that you can get into the challenges of that industry is how completely automated a lot of it is. Where a lot of people in PR are not thinking specifically about how to tell the right story to the right potential media outlet. And instead, what they're doing is they're just playing a numbers game and they're just blasting it out to everybody. And that means that you could end up... I write this newsletter, right? Entrepreneur Magazine is the thing that people obviously would pitch. But then I have this newsletter where I don't interview anybody. There's no opportunity to be featured in my newsletter. And I still get pitches to the newsletter because somebody saw it and dropped it in some spreadsheet and it just, now I get it. And I think that's a real disservice to entrepreneurs who are paying for people to do that. And I really hate that. Yeah. Okay. So we're going to get into the meat of just how to actually do this well.


The impact of press coverage on startups (07:41)

But a couple more questions just to set a little context. One is in terms of impact. What kind of impact have you seen from getting press for a startup in terms of growth for their product specifically? So it's a really wide range. I have had entrepreneurs tell me that a single story in Entrepreneur Magazine, like the print magazine, or just online, will drive more, you know, whatever, more app downloads, more sales that month than any of their paid marketing efforts. But then I have also heard entrepreneurs tell me that it didn't do anything for them, or that it did one very specific thing for them, which is to say maybe some potential partner read it and reached out and it started an interesting conversation. It's all over the gamut. And it's a really important thing for people to remember is that this is not something that I think that you should bank on as a strategy for growth. It's a great add-on, but if you think that press by itself is going to solve your problems, you're wrong. Because it might, but it's way too unpredictable.


Is there anything else along those lines of just when it's worth somebody investing time into getting press, either stage of startup, type of startup, any just general broad advice of like, you should not be spending time on trying to get press versus like, this is a really good opportunity for you you think about press the same way that you think about raising money which is to say you do it when you know what the money is for and you should do it when you know what the press is for a lot of people reach out to me at such an early stage that if we wrote about them it wouldn't get anything. They're not at a stage where they could use that press in any meaningful way. And so there's really no purpose in chasing it now. You should step back and think really as a starting point, like, what do I need press for? And if you have a good tactical answer to that, that could be because I need to drive awareness to a new product. That could be because I'm going out to raise money and I need articles to show that the marketplace takes me seriously. These are good reasons. But I get a lot of emails. It's funny because people, entrepreneurs in particular, they're often just so vulnerable and it's kind of a wonderful way sometimes. Sometimes people will just email me and they'll just say, you know, I've worked really hard and I just feel like I deserve this. I respect that and I relate to it in some ways with my own trying to get attention for my own work, but I deserve this, that's not a good tactical decision for your business. That doesn't do anything for you. And so I would put that to the side and only think of press as like, you don't go out and raise money if you don't know what the money is for. You shouldn't go out and try to get press if you don't know what the press is for.


When not to pursue press coverage (10:37)

I'm curious to hear other examples when it's a bad idea, because as an outside observer, I would always love to get more attention for my product and more people to be aware of it, more people to check it out. Is there an example or anything that comes to mind of like, there's no need for you to do that in this moment or for this product? Oftentimes, it's not even about the moment, but it's about the publication. So I'll give you an example. I spoke at an event once and afterwards this guy comes up to me and he has a small hot dog food truck business in Washington DC. So he's got a couple of trucks and he's doing good business selling hot dogs. And he wants coverage in Entrepreneur Magazine. He's like, oh, how can I get a feature? And the problem with that instinct that he has is that he's really directing his energy in the wrong place. Because if he is selling hot dogs in Washington, D.C., then I understand what press is for for him. Press is to drive hot dog sales. That's what he wants to do. Entrepreneur is not going to do that for him. Full stop. Why? Because entrepreneur reaches a national to international audience. So that means that 99.5% of the people who would read a story about this guy have no ability to go get his hot dogs, which means that that was wasted effort. So fine. Was it that hard to come up and talk to me at the conference? No, but like scale that out, right? Like how many emails is he sending that are like that? How much energy is he putting into chasing things that ultimately don't have good direct value to him? What he needs to do is think, okay, my goal, get more people to buy hot dogs. Where am I? I'm in Washington, DC. How can I reach people who are interested in food in my market? So stop chasing entrepreneur and start chasing the local eater or the food section of the Washingtonian or something like that. Right. That small shift can give you a lot more payoff for your effort. This is a good segue to just let's just dive into how to actually go about getting press.


Jason’s three-step press strategy (12:38)

And I know you kind of have this three step structure for thinking about it. Maybe just start with what are the three steps and then we'll dive into each one. Yeah, sure. So I mean, look, it's pretty simple, right? Step one is prep. You want to be thinking about how to tell your story. You want to be thinking about the kinds of stuff I just talked about. What is press for for you? Everything that you need to do to orient yourself towards what is this opportunity and why am I chasing it and how to make the most of it. Step two is figuring out who to pitch. Not all press is created equal. There are not reasons to just go chasing everybody arbitrarily. The hot dog example is a good one. So finding the writers and editors who you're actually going to reach out to, who are going to be most receptive to you, and also making sure that because you did the prep, you can figure out how to tell your story in a way that they're going to be interested in. We'll talk about that. And then step three is the actual pitch. What does it mean to reach out to these people, to engage the writers and editors? How do you find them? What do you send them? What are you telling them? That's it. I mean, right? But what you need to understand is that you're entering a world that probably doesn't operate the way in which you think it does. And I see that all the time as the recipient of pitches. People don't understand who they're reaching out to and how I and my colleagues think. We should maybe even start with that because that's a really important thing to understand. Just like, again, to go to the back of the metaphor of the investors, you don't reach out to an investor if you don't understand what that investor does, what they're interested in, or what kinds of companies they invest in.


Unpacking the media’s mission (14:01)

You can't do that with media either. So I get pitches every single day along the lines of, how do I get coverage in Entrepreneur Magazine? How do I get a feature in Entrepreneur Magazine? To me, it always feels like they're ordering like a hamburger from me, right? Like how do I get a hamburger from Entrepreneur Hamburgers, right? They're treating me like a service provider, like that my job is to provide press. And I get it because of course, if you're an entrepreneur and you're looking for press, then the writers and editors out there seem to be in the business of writing about people. And therefore there's some service that they seem to provide, and you're trying to figure out how to get it. But that's not how the media thinks of themselves. how the media thinks of themselves. The editor, the writer, I'll just say it as plainly as possible, they don't care about you. They don't care about you. They care about their reader or their listener or their viewer. That's who they care about. That's who they're serving. And if you can be of use to them in sharing the kinds of information that they are looking to serve their audience, then you can get what you want. But you can't treat them like a service provider because they're not. And so you have to approach them with an understanding of what they're trying to do for their audience and how you can fit into that. Because if you don't, they are not interested in you.


Identifying a publication’s mission (15:48)

I love that. And more even specifically, what is it they're trying to do for their audience? I imagine it's just have something interesting that they want to read, something they can learn, something they're like, wow, I'm really excited to read this. Yeah, but it's going to be more specific based on the mission of each publication. For example, I've worked at two separate business titles. I was a senior editor at Fast Company for a number of years, and now I'm the editor-in-chief of Entrepreneur Magazine. The decision that is made about whether or not a story belongs in a publication, it was totally different based on these two publications. So I can't speak to Fast Company now because they've gone through a couple of leadership changes. I don't know what their mission is. But back when I worked there under Bob Safian, he was the editor-in-chief, that was really a magazine about where business is going. And the stories that were in the magazine were all supposed to be in some way representative of the evolution of business. And so when people would pitch, what we'd really be looking for are, are there insights in what this person is doing that other people could read and say, aha, that helps me understand where this industry is going or that industry, could read and say, aha, that helps me understand where this industry is going or that industry, or that helps me think about how I can shape my own company to match current trends, that kind of stuff. Entrepreneur, totally different mission. The way that I think of entrepreneur is that it's not even a magazine about business, it's a magazine about thinking. What I want to do is make sure that everybody who comes to the magazine walks away with great insights into how to think through the challenges in their business. And so what I'm looking for when somebody reaches out is, did they make some interesting counterintuitive decision that solved a problem in their business? And I'll emphasize in, because oftentimes when people hear me talk about solving problems in business, they think, aha, but I solve a problem in business, right? Like I saw that there weren't the best razors in the world and I made the best razors. That's not what I'm talking about. What I'm talking about is, this is a woman whose name is Joelle Mertzel. She has a company called Kitchen Concepts Unlimited, and she makes a butter dish. And it's a really smart butter dish because it is built on a hinge, right? So this is designed to solve a very specific problem, which Lenny, I don't know if you knew this, I did not, that you don't need to refrigerate butter. Did you know that? I knew that intellectually, but I still refrigerate it. Like I know people don't. Me too. Even though I've had multiple conversations with this woman about this. You don't need to refrigerate butter. And know people don't. Me too. Even though I've had multiple conversations with this woman about this. You don't need to refrigerate butter. And if you leave it out, it cuts easier. It's more spreadable. Big problem, the butter dish. So most butter dishes, you just lift up. And so if you have warm, room temperature butter that's soft and you lift the butter dish top up, you might bump into the butter and it's going to make a big mess. So Joelle makes a butter dish on a hinge, right? Opens and closes exactly the same way every single time. No mess. Brilliant. Solves a problem. She reaches out to me about this. This is not interesting to us, right? Maybe this is interesting for a cooking magazine, right? Maybe Bon Appetit is interested in this. Entrepreneur is not interested in this because that doesn't help other entrepreneurs to have thought through that problem. But then she tells me something else. What she tells me is that she is, at the very beginning of this, trying to figure out how to answer some basic questions about her audience, like what colors do they want in this butter dish and what price point are they willing to pay? And she wants to do some market research. She goes to a market research company. She says, how much would it cost to research consumers and answer these questions? They say $10,000. She doesn't have $10,000. And then one day she is sitting at the airport waiting to board a flight. And she looks around and she realizes that airports are full of people who have absolutely nothing better to do than answer questions about butter dishes, right? Like nothing better to do, just sitting there. And you could start at gate one. By the time you get to gate eight, everyone at gate one is new. You could do it all over again. And you could have a 6 p.m. flight and you could show up at 9 a.m. Nobody's going to stop you. You could do this all day in the airport. And this is how she starts to do her all over again. And you can have a 6 p.m. flight and you can show up at 9 a.m. Nobody's going to stop you. You can do this all day in the airport. And this is how she starts to do her own market research. She saves that $10,000 and she does it herself. I put that story in the magazine. It's tiny. It's this tiny random company and this random decision. But the reason I did it is because every time I repeat that story to entrepreneurs, they're all like, ah, right, totally. There's always other ways to do things. They love the ingenuity of it. That's what I'm looking for. That's entrepreneurs' stories. So it's not, to go back to the point that you were making, it's not just about, well, it's a magazine called Entrepreneur. They must write about entrepreneurs, right? Oh, I'm an entrepreneur. I belong in entrepreneur. People think that all the time. No, you have to step back and read what these publications are publishing and ask yourself, what are they doing? What is the purpose here? The editors and the writers are making decisions about what goes in this magazine, and they're making decisions about how the stories are constructed. Why are they doing that? Who are they trying to reach? When you start to see it through that lens, you start to see the pattern and you get an understanding, a real instruction manual for what it actually means to pitch these publications. That is such an interesting insight. I had no idea that that was something you should be thinking about. Is there an easy way to understand the mission of the publication? Is there like an about page they often add this to? Or is it like you said, you just read a bunch of stuff and try to suss it out? You know, nobody publishes an about page in that way, because that's the internal logic of the editorial team. But you can certainly make some starting assumptions based on who the publication is trying to reach. Everybody is trying to reach somebody. It gets more complicated the more general interest something becomes, right? Like what is the New York Times? What is the mission? That's a hard thing to answer. You sort of have to divide it up into sections, right? The mission of the National News Desk is different from the mission of the Business Desk. And even within there, the mission of the Sunday Business Section is different from the mission of the business desk. And even within there, the mission of the Sunday business section is different from the mission of the Monday to Saturday business section. So you have to start to really parse it out. And this is the reason why people hire PR is because if they're good at their jobs, they understand a lot of this already. But I really do think that if you spent time with the content, and your starting point is, I understand that this publication is trying to reach X. They're trying to reach these people. Then you can start to see the patterns of what it is that they're doing. How are they telling stories? What do these five stories all have in common? They have something in common. There's something that they're all doing. And you can certainly read the tea leaves and try to figure it out. Awesome. Okay. Feels like we've already gone into step one around prep. What else is involved in preparing to get press? If we're talking about prep, the very first thing that you need to do is what I had said earlier, which is just ask yourself, what do I need press for?


Step one: How to prepare for outreach (22:56)

And you need a good answer to that question. And once you have that, the next thing you should do is you should start to think about, well, what's interesting about my business? And oftentimes, it's not necessarily what you think. And you can be guided in a way by what's happening in step two, where you start to think about who you're trying to reach out to. Because, for example, the story that somebody might tell me, an entrepreneur, is going to be different than the story that somebody might tell Cosmo. There's a reason for a company to end up in both entrepreneur and Cosmo, right? Maybe the product is for young women and so Cosmo might be interested in some kind of product feature or including the product in a roundup of some kind of products. Whereas entrepreneur would do the entrepreneur focus story. What did this founder do? How did they... You can think about your story and break it up into a whole bunch of different little pieces and then figure out which piece goes to what media. But oftentimes, people make the mistake of trying to do that in reverse, which is to say that they kind of decide what narrative they would like to have out in the world, and then they just go around to different publications trying to sell them on that. I get that all the time. A lot of my pitches that I'll receive in my inbox are somebody who hasn't really thought at all about what entrepreneur publishes, but instead just has something that they would like to get out into the world. I mean, a good kind of dumb example is yesterday somebody sent me an email about a company that had just hired a new president. I don't care about that. That's not useful to my audience at all. I'm sure that there is a trade publication, right? Let's say that there was a company in the restaurant industry. I'm sure that a trade publication that follows the blow by blow by blow of a restaurant industry might be interested in your new president, but I'm not because you hiring that new president isn't useful to my audience. Stories in Entrepreneur are not really about the person that I'm writing about. They're really about the audience. They're really me serving the audience through the stories of the people I'm writing about that's not useful I wish that they had spent a moment and thought about that but they didn't so once you start to think about who it is that you're trying to reach you can step back and say well what part of my journey is going to be most relevant to them. And I would push you to be really, really creative about it. Because if you go back to the buttery example, the butter dish, that little funny story about the airport, I mean, who else is writing about that? It's not central to her story as a brand. It's not central to her sales pitch. It was just for us. We were probably the only publication in the world who cared about that, but I really cared about it. Amazing. Okay. So just kind of summarizing what you shared, think about the goal. What are you trying to get out of press?


How press can help you (26:11)

And goals could be awareness of what we've done, something new, investor interest. What are some other common examples of goals that you see for trying to get press? So yeah, awareness of something new, but it also doesn't have to be awareness of something new. It could just be continued growth, trying to reach into a new marketplace. That's fine. Anything that's tied to growth or reaching a new customer base would make sense. Cool. That makes sense. But it could also be that you're looking to position yourself in your own marketplace a little differently. So I see, for example, a lot of people, a lot of big companies keep knocking on my door because we don't just hear from startups. We hear from major companies as well who are pitching stories. And I know why they want to be an entrepreneur. They want to be an entrepreneur because they're trying to position their brand as also being relevant to small business owners. And so it's helpful to have that kind of context because coverage and entrepreneur can help them go out to the marketplace and say, look, we're also reaching XYZ people. So sometimes it's not even about a conversion, but rather it's about a positioning. And that's a good reason to also maybe put forward your executives. Sometimes it's just about establishing your CEO or your founder as an authority in a particular area because you want them to be more trustworthy. You want them to be invited to more conferences because all of that stuff draws more attention to the company. All sorts of reasons to do this stuff. And then, yeah, trying to get in front of investors, trying to get in front of partners. Look, there's a million reasons why being visible can be useful, but you need to make sure you understand what you're actually trying to do. Okay, awesome. That was really helpful. So think about what goal you have in mind for getting press. Pick a publication and understand their mission and what their goals are. And then think about some interesting stories that you could pitch them, not just like we have any president, but something that you think they'd be excited to share that connects with their mission. That's right.


When to work with a PR agency (28:25)

Kind of on this topic, I know we want to talk about who to contact and how to figure out who to actually talk to. A couple of questions that come to mind. This is all a lot of work. Founders are really busy. So the begs the question, PR agencies, do you have a perspective on would you recommend working with PR agencies? Is there a time when it makes sense to and doesn't make sense to you? Yeah. I mean, it's a ton of work, right? Like everything that I'm describing is a ton of work. And let me be clear. People succeed in getting press without doing any of the things that I'm describing because dumb luck happens in the world, right? You could very well just bang out an email to some random editor and they might like it. That is entirely possible, or you could disregard everything that I've just said. What I'm really helping you do is try to optimize your approach. But yeah, hiring PR can cut out a lot of this. Now you're not doing this research yourself. You're not thinking through these challenges yourself. You're working with people who understand exactly how to identify the most interesting parts of your story and then turn them into good pitches. So why wouldn't everyone do that? A couple of reasons. Number one, cost. PR can be expensive. So you just have to factor that in. Number two, PR is and can be, I'll say can be a very frustrating journey because a lot of PR people are very bad at their job. They're very bad. And this isn't just me bashing PR people. I have literally been hired to give keynotes at PR industry conferences. And I get on stage and I say, most PR people are bad at their jobs, everybody nods. And they all know it, right? Of course, none of them think that they're one of the bad ones, but they all know it. PR is full of people who are bad at their jobs. Why are they bad at their jobs? They're bad at their jobs because they're lazy, because they're primarily relying upon email blasts, just sending things out because they have a older idea of what it means to get the word out. For example, if you hire or talk to a PR agency and one of the things that they recommend doing that you should spend money on is a press release, like a traditional press release, run as fast as you can away from that. I don't know if you know this, do you know this? The press release, there are some purposeful reasons to put out a press release, but the press release is really no longer the primary unit of press attraction. Yeah, I get that sense. Yeah, but here's what's fascinating. So a PR agency, a PR agency I wouldn't recommend might do this. They'll tell you, we're going to put together a press release about this new thing. So you have to pay a little extra money for the production of this press release and then also the distribution of this press release because what we're going to do is we're going to put it out on the wire, right? Because there are a whole bunch of press release distribution wires. So they'll do that. You'll pay the money and it'll go out on the wire. And then they'll send you a report about all the places that this press release ended up on. It ended up on Yahoo Finance. it ended up on market watch right and it technically did like the the press releases there it was posted and zero people are going to see it in the whole world because yahoo finance has a section where they just publish every damn press release that gets published by all these different just publish every damn press release that gets published by all these different distributors. Nobody saw that. So don't confuse posting press releases, even on very big websites, with actual success. What you want in an actual PR person is someone who traffics in one thing, and that is relationships. The most important thing that a PR person can have is active relationships with people in media.


PR insights and red flags (32:16)

Why? They cannot guarantee. If a PR person is guaranteeing you press, that's another reason to run out the door as fast as possible because the PR people cannot control this. Writers and editors, they do what they want. It's a completely subjective industry. Very frustrating. I completely understand that. It's totally subjective. So the best that a PR person can do is shape your story, understand who to pitch, and then get that writer or editor to look at it, to pay attention to it. There are some PR people in this world who I think very highly of. I think they're incredibly smart, they're incredibly good at what they do, and they only pitch me when they have something that they think I will genuinely be interested in instead of a lot of PR people who just send me some random thing every week or every day. I don't pay attention to those people. But when, I don't know, just like shout out when John Beer from Jack Taylor PR sends me, like, you know, John, I met him in a PR capacity like a decade ago. We've since become friends. Like when he emails me, I pay attention. I don't write about it all the time. I'm not going to write about something just because I like John, but I will pay attention. And paying attention, honestly, is like half the battle because people in media are getting so much email. So you want someone who's going to understand you, understand your industry, understand and know the people who they should be reaching out to and who really respect you as an entrepreneur and are going to give you the hard feedback. Because there are a lot of people who will go and hire PR and they'll say, I want you to email this and this and this and this and this publication. And if the PR person just does that, all they're doing is like annoying their contacts. If they don't really feel like this was meaningful, you should like when a PR person pushes back on you and says, you know what? I don't think that your story is right for that publication. Here's why. That's someone you should hire. Is there any other PR people you want to call out as ones that you think are awesome? The challenge here is that I'm going to regret not including a whole bunch of people who don't pop to mind immediately, but- You can include them in the show notes, whoever else. Yeah, sure. Okay, so let's see. Off the top of my head, so John, Jack Taylor, he does a lot of wellness stuff. So PR agencies tend to specialize, and so you want to make sure that you're going with people who really understand you and the media ecosystem that you're reaching out to. So I think that John's really smart. Let's see, Hannah Lee at Hannah Lee Communications is great on hospitality stuff, so restaurants, hotels, booze. They're really smart. Jen Squilla, sorry, Jen, if I mispronounced your name, at Max Borges Agency, really good on sort of consumer-focused products. Greg Delman, he's based in San Francisco. He has a boutique shop called G3 Media, and he does a lot of tech startup stuff, just really knows that world. Greg, I'll find writers through Greg because he just knows everybody. I just texted him recently. I was like, I need somebody who can write about this very specific AI thing. He happened to be at TechCrunch Disrupt and he found some freelancer and connected us. That's great. So those are four. I will have more that I'll give you for the show notes. Amazing. Okay. This is really useful. If any come to mind as we're chatting, feel free to shout them out again. Similar question, when people are thinking about publications to go after, say you're a startup founder, is there a list you could just share of just like, here's probably the top five, 10 that you should be thinking about?


Selecting the right publication for startups (36:02)

Like the obvious ones you talked about, Entrepreneur, Fast Company, TechCrunch obviously comes to mind. Is there others that are just like, here's a good list to start with? Honestly, it really so much depends upon what it is that you're looking to do. You could be a startup founder and entrepreneur and Inc. and Fast Company are, for maybe some good reason, not at the top of your list because you're a startup founder, but your goal right now is to reach consumers. And those publications don't reach consumers. And they don't reach people who are in a buying mindset. They reach people who are in a buying mindset. They reach people who are in a creating mindset. So I would expect that if you have a startup and that startup is not like B2B in some way, that it would be possibly very reasonable that business publications might not be your target right now. Maybe men's health is. Maybe, I don't know, anything could be. it right now. Maybe men's health is. Maybe, I don't know, anything could be. Oftentimes, people tend to think too close to them about where they belong. Here's a real kind of exchange that happens, which is if somebody will email me, I don't respond to every publicist. It's just literally not possible. I would not have enough time in the day. I do do my don't respond to every publicist. It's just literally not possible. I would not have enough time in the day. I do do my best to respond to every entrepreneur who reaches out because I feel like they deserve a response. And sometimes somebody will email me and they'll send me something and it's just not relevant. And I'll reply and I'll just say, hey, thanks, congratulations on what you've built, but this isn't a fit for entrepreneur. And maybe once a month, somebody responds really in a testy way, and they're like, but don't you write about entrepreneurs? I'm a great entrepreneur success story. And it's like, no, that's not what we do. Yes, entrepreneurs are featured in our stories, but no, we're not just like a directory of entrepreneurs, right? Here's a good way of thinking about it. If you have a startup and you're trying to figure out what publications to be in, go look at where your competitors have been featured. That's a great place to start. What audiences are they reaching and how are they doing it? That should give you some direction about where you might want to go next. Awesome. Awesome advice. On TechCrunch, do you have a perspective on is it worth investing in getting featured in TechCrunch? I'll tell you a personal press journey moment, and then I think that it will translate into the answer for TechCrunch. Amazing. Okay. Something we haven't talked about so far yet is, and this is sort of almost skipping all the steps that we've laid out to like what happens after you get the press, but like the point of the press is sometimes to reach the people who are reading it, right? Like you get covered in entrepreneur and entrepreneurs are going to read it and maybe something good will come of it. But sometimes the point of it is not to reach the people who are reading it at all. Possibly a very small number of people are going to read it, which by the way is a real, real possibility. Because although all of these publications that I have mentioned, Entrepreneur, Forbes, Fortune, Inc., Fast Company, whatever, whatever, these are reaching millions of people. Their websites get many, many, many millions of unique visitors each month. That does not mean that your story is going to be read by millions of people. In fact, the largest possibility here is that your story will reach like 5,000 to 10,000 people, a small number of people, because these publications are publishing tons of stuff. So you might get this story. It might look awesome. It might not reach that many people. That might also be okay, because maybe the reason in your logic for why to get that kind of coverage is not to have reached that publication's audience at all anyway. Maybe what it really is, is to tweet it and then put some money behind promoting that tweet. Because then you can target that you got coverage to the people who you want to notice you got coverage. And I see a lot of people do that. They'll take articles that we ran on Entrepreneur and they'll basically turn them into advertisements. That's really smart because what they got out of Entrepreneur was the social cache. It was the validation in the marketplace. Then they're going to do something with that themselves. That's really smart. You also see it, right? Sometimes the reason to get coverage is just so you can put it on your website as seen in. As seen in is probably more valuable than anyone actually reading that story to begin with. They probably won't read the story. You might not even have to link it on the website, but you could just get to say as seen in because, again, it gives you that validation. a small podcast company with my friend Nicole Lappin. Nicole Lappin is this best-selling money expert. And we have a company. She's the founder and I'm an advisor. And it's called Money News Network. We have a podcast on it called Help Wanted that we co-host together. And we got coverage in Variety. And that was the result of pounding on a lot of doors and finally getting someone at Variety to take interest. And they ran an article about us. Did we get anything from that story in Variety? The answer is no, like nothing. But you better believe that every email we send out to every potential advertiser, to every partner includes the link, right? Variety has covered us. And I guarantee that when someone receives that email, it makes them pay more attention. And I have used it many times too, when I reach out to people, it just gives you that validation. So sometimes what you're looking for is a prize to walk around with. And I would bet that the same is true for TechCrunch, which was your original question, like, why get the funding announcement in TechCrunch? Probably not because anyone's going to care because they read it on TechCrunch. But now you can use that to your own means. And sometimes that's more valuable than the press itself. That is an awesome insight. It also makes you realize you may not feel like it was a success after working, spending all this time getting a story and entrepreneurs like, oh, nothing happened. But the benefits may come later, like weeks, months, years later when you start to share that. Right. A lot of this is what you make of it. Amazing. Okay. That was extremely interesting. Okay. Let's talk about step two. So initially you prepped, we talked about how to think about who to go after and the mission and goals.


Effective Pitching And Engagement Techniques

Step two: Identifying the ideal pitch recipient (42:34)

Then you get to step two, which is figuring out who to reach out to at a publication. Okay. So a lot of people make the mistake of emailing me, right? If they want coverage in Entrepreneur, they email me. And I understand why they're emailing me. It's really for two reasons. One, I'm the most visible editorial person at Entrepreneur. And so it's easy to find me. It's easy to find my email address. And also they just assume, well, editor-in-chief making all the decisions. But no, right? I mean, think about it. If you have a problem with a purchase that you made on Amazon, you don't email Bezos. He's too busy. And I'm not comparing myself to Bezos, but I'm the busiest editorial guy at Entrepreneur, for whatever the hell that's worth. And I'm just not the guy to pitch because my job actually isn't really to select stories that go in the magazine. My job is to work with editors who develop their own ideas and then I get to say, oh, that's a good one, or like, oh, let's refine that. I'm not sourcing as much. And so you really should start by looking at who's writing about your subject area. And you can do that by going to the website and surfing around. You can do that by Googling around. But you'll find the answer. Every publication is structured differently. Some people have specific beats, right? Some publications will be like, this is the person on the transportation beat. And some publications don't. Entrepreneur doesn't really have a beat system necessarily. But if you look, you'll figure it out. Oh, that editor is clearly interested in food, or that writer is clearly interested in food. They seem to write all the food stories. Oh, that person is writing about... And a good way, again, to do it is to start with the publication and then look at how they're covering your competitors. So a good example is I was once consulting with a guy who has a kind of fun peanut butter company. It's like, imagine peanut butter meets Ben and Jerry's. So it's like peanut butter with lots of stuff and fun names. And so he's trying to figure out how to get press. And originally, his thinking, the reason why he reached out to me was because he's like, well, I'm an entrepreneur. I run a business. I should be an entrepreneur. I was like, no, no, no, you shouldn't because none of our readers are going to buy your peanut butter. So who is your target audience? Who's buying your stuff? And he says, millennial moms. I said, great. Okay. So Cosmo is a good place to reach them. So let's look at how Cosmo covers snacks. I don't know how they cover snacks. I don't read Cosmo, but let's find out. It's not hard. I went to cosmopolitan.com, searched for snacks. What I found immediately was a lot of stories that are all basically roundupy and anchored to some time-sensitive things. So it's 10 snacks for Valentine's Day. It's our 10 favorite new fall snacks, whatever. It's all stuff like that. So now we know they are not going to run a thousand word feature on your peanut butter company. Instead, the best that you could hope to do is get into one of these seasonal-ish roundups. So now next step, who's writing these things? Let's look. Let's open some of the articles. The byline is right there. You can click on the byline. You can see what this person does. And in many cases, this person will be, maybe they'll, maybe they're the food editor. Maybe they're the lifestyle editor, whatever. Like, like you'll see what they cover and you'll have a good understanding of now how to frame the thing that you're looking for. Now, let me introduce one other possible option. how to frame the thing that you're looking for. Now, let me introduce one other possible option. They don't work for the publication at all. They're a freelancer. Publications use a lot of freelancers. Freelancers are basically independent contractors. They're writers who are working sometimes. Sometimes they have kind of longer term deals with publications. Sometimes it's just one-off. My wife is a freelancer. My wife is a freelancer who writes a lot for the New York Times and Washington Post and Guardian. And the interesting thing about my wife versus me is that my wife, whose name is Jen Miller, just so I don't keep saying my wife, so Jen. So Jen, on a day-to-day basis as a freelancer, on a day-to-day basis as a freelancer is hungrier for stories than me because Jen has to hustle for her food, right? Jen has to find stories and pitch those stories to editors at publications. And that's when she gets paid. So she actually is more incentivized to be looking for stories than I am because I am a salaried employee of Entrepreneur Magazine and my email address is very easily found and people just send me stuff all the time. I should add here also, note that a good journalist, a good writer is not actually sitting around thinking that their job is to wait for people to pitch them so that they can just write about the best pitches.


Pitching best practices (47:27)

Their job, as they see it, is to go and find the most useful things for their audience. And they like to do a lot of that themselves. So they're not sitting around just waiting for your pitches. And in fact, your pitches have to overcome their instinct to go find things themselves. So Jen is constantly hustling. Jen is constantly talking to people. Jen is curious about the world and will spend a lot of time hunting things down. But if somebody reads a story that she wrote and says, ah, I think I have an idea of what this person is interested in, and then tracks her email address down and then emails her, Jen is getting a lot fewer pitches than me. The chances of her reading it are close to 100%. And the chances of her taking it seriously, if it's relevant to any of the publications that she writes for, is much higher than me. So sometimes going to the staff person is not actually your best move. Finding the freelancer who's doing the work is sometimes the better move. So many interesting tactical insights that you're sharing. I love it. With this freelancer tip, how do you know they're freelancers? They're like something in the byline? If you find them on the publication's website, so let's say that you go to Cosmo and you click on an author's bio, if they're staff, it'll say staff. If they're not staff, it'll probably say something else. It might say writer. It might say writer. It might say contributor. It might say, you know, Jen Miller is a writer in Brooklyn, New York. But also, you can just go one extra step and just Google their name because any smart freelancer has a portfolio website where they should be very easily found. So sometimes just take their name, plug it into Google. You'll very quickly figure out who they are. Okay, so let me summarize things that you've taught us so far. One is think about publications that go to people that will buy your thing. So in your example, Cosmo is a good example of someone who'd buy this peanut butter thing. Two is don't think of it as like a broad thing. Think about the writer at the thing. Two is don't think of it as like a broad thing. Think about the writer at the thing. So it's not like Cosmo would write about this. It's like who specifically at Cosmo would write about this. And the way you find that is go to their site, search for, you talked about search for your competitors, but I think it's even broader, just like things related to your area, right? It's like snacks. Yeah, that's a good point. Search for your category. Even like adjacent things probably are close enough. Right. Mm-hmm. And then this tip about freelancers is really great, that they're hungrier and that they're more likely to respond to your pitch versus someone that's working there and just like- And then also this point that they're like, their assumption is this is not a good pitch and they don't want your pitch, but freelancers have a higher chance of being interested in and will pay attention. Yeah. Freelancers got to eat. Amazing. Is there anything else along this step of finding somebody at a publication that you want to share? Well, the next step is going to be how to actually reach out to them and pitch. So at this stage, I think that we've fairly well covered it. I love your summary and just to double click on part of that. The reason why you're doing a lot of this is not just for the crazy busy work of it, but it's because you have to understand that the media, just go back to translating the media. The media, which is a phrase that is used in all sorts of different ways, is a pretty bad way of actually understanding the media because the media, quote unquote, makes it feel like it's a unified entity. Either, you know, in politics, the media will be criticized as a sort of like multiple publications colluding together in some way. But the way that we're talking about it is just like kind of as organizations that you're trying to reach out to. But really and truly, these are just publishing companies made up of individuals. And those individuals are all making fairly subjective decisions about what it is that they're going to write about. And there are layers of approval that they have to pass through. So nothing makes it into the print magazine, for example, without me saying yes, right? But I'm also trusting my editors to be passionate about the ideas that they're finding and convince me of yes. And so the thing that you are really looking to do is to find the way in to a publication because nothing gets covered until a single individual at a publication takes interest in you enough that they go to somebody else and say, I think that this would be a good story. And that other person says yes. So you have to find your way in because media is not a coordinated effort. It's a bunch of people showing up every day, trying to figure out how to make the best thing for their audience. Amazing. Okay. So that's a great segue to final piece, which is actually get someone excited and write about you.


Step three: Creating excitement around writing about you (52:26)

So how do we do that? How do we do that? This is where really the rubber hits the road. Okay. So things not to do. Don't call them if you track down their phone number, which is a real thing that happens. People call my personal cell phone number. It doesn't happen often, but it happens. And I don't even know where they get it from, but I don't like it. And media people are torn on whether or not DMs by social are an okay way to reach out. I find them kind of annoying because number one, the format doesn't lend itself very well. If you write anything long in a DM, it just looks like this endless thing that I got. But also, I don't know, my Instagram DMs, I just kind of don't think of as the place to be pitched. But other people don't care. So I don't know, you can roll the dice on that. Email is just the most traditional way. If you know somebody's going to be speaking at a conference, that's great. Come up. You can talk to them. But the question, of course, is what are you sending them? And here's what you're sending them. You're really sending them the product of the work that you have done in the previous two steps. Because you have now spent some time thinking about your story and who you're pitching and the publication and how they're telling stories to their audience. And then the individual person who you're reaching out to, who you now have some sense of how they write about this. And you're taking all of that and you're trying to distill it down into a presentation that they're going to find appealing. Which again, to go back to the thing about how press is not that dissimilar to going out and raising money, that's kind of what you're doing when you go and meet an investor too, right? If you have meetings with 10 investors, the way in which you talk about yourself and the company should not be exactly the same with those 10 investors because they're all going to have somewhat different approaches and different theses. You're not trying to scam anybody, but you're just trying to be as customized as possible by building in your knowledge of what it is that they do and what their firm does. The same is true for media. All of this is really going to take the form, in its most traditional sense, of a short email, a short email pitch. What does that look like? I mean, look, there is literally no magic answer to that. But I wish that there was, but there is not. There's no format. People always ask me, like, what should the subject line of the email be? It's a good question. There's not one answer to that. The closest that I can give you to an answer is that picture me at my computer. I have a lot going on and I'm glancing at my email and 40 new emails are sitting there. And my instinct is to delete all of them as fast as possible. But I'm going to glance at each one. I'm not going to open each one, but I'm going to glance at it, which means that I get, you know, I see the subject line and I see like the preview text or just the first thing that somebody had written. What you want to do is write something that makes it pretty clear to me that this is targeted to me. That's step number one, because most of those emails that I got in my inbox are not targeted to me. They're mass blasts and I'm delete, delete, delete, delete, delete. So which is the one that actually is reaching me? And sometimes you can do that by referencing something that I wrote in the past. I see people do that a lot. Don't fake it. People fake it all the time. People email me and they tell me they're fans of my work. They've never read my work. It's very obvious, right? Like, don't fake it. People fake it all the time. People email me and they tell me they're fans of my work. They've never read my work. It's very obvious. Don't do that. But if you've read something or if you're familiar with something, if you're familiar with the publication in some way, any signals of that are good. Because again, what you're trying to do is just separate yourself from noise to this is customized to you. Because if you think about it, this is really like an efficiency question. What I'm trying to do is I'm trying to spend my time on the things that have the highest percentage chance of being relevant to me. And I'm filtering out the things that seem not relevant to me, who are wasting my time. So if I see something where somebody's writing me and they have a sense of the publication and they have a sense of me, there's a higher percentage chance that the next things that they're going to tell me are going to be relevant to me, maybe even turn into a story, which is great. I like when that happens because it saves me time, frankly, right? Then I, there's one less story I have to find myself. So I'm happy for it, but it's got to be right. So you want to structure. And then the email that you're writing is don't go on forever, like three paragraphs max. And you are telling the version, you're not like writing an article, right? But you're telling me the thing that you are pretty sure I'm going to be interested in. It's the difference between going back to the butter dish example, woman sending me a three paragraph email about the butter dish itself and opening up, telling me a little bit about the butter dish, and then immediately moving into this very clever story about the product market testing survey. That's the difference. She told me the story that was going to be relevant to my audience. She got there quickly. And it felt like to me, this is a interesting human being with an interesting entrepreneurial story to tell. And that's why I'm going to engage. And now, so that story actually came through a cold email. That was a cold email. Yep. Just showed up one day. Amazing. This episode is brought to you by EPPO. EPPO is a next-generation A-B testing platform built by Airbnb alums from modern growth teams. Companies like DraftKings, Zapier, ClickUp, Twitch, and Cameo rely on EPPO to power their experiments. Wherever you work, running experiments is increasingly essential. But there are no commercial tools that integrate with a modern grow team stack. This leads to waste of time building internal tools or trying to run your own experiments through a clunky marketing tool. When I was at Airbnb, one of the things that I loved most about working there was our experimentation platform, where I was able to slice and dice data by device types, country, user stage. Epo does all that and more, delivering results quickly, avoiding annoying prolonged analytic cycles, and helping you easily get to the root cause of any issue you discover. EPO lets you go beyond basic click-through metrics and instead use your North Star metrics like activation, retention, subscription, and payments. EPO supports tests on the front end, on the back end, email marketing, even machine learning claims. Check out EPPO at geteppo.com. That's geteppo.com and 10x your experiment velocity. Is there any other examples that come to mind of someone doing this well for people to have more kind of examples of like, here's... Oh, sure.


Success story: Meg O’Hara’s pitch (59:10)

So, well, here, let's see. This is, we'll have to do this in real time here. But I keep in my inbox a folder called bad PR pitches and a folder called good PR pitches. We can go through both. Let's do it. All right. So this is, I just pulled this up. So this is, and I haven't read this in a long time. I'm kind of like trying to read ahead as I'm talking just to see if this is appropriate to read, but I think so. I don't know. Whatever. We're just going to read it and see what happens. All right. So the subject of this was idea for entrepreneur and problem solvers, how the border closures grew my business. So this was sent to me in September of 2020. And this is a good or a bad? This is good. This is good. This turned into an episode of a podcast that I do for entrepreneur, and I might have also then converted it into an article. I can't remember. Awesome. And so here's what she did. So her name, I'll shout her out. So this is Meg O'Hara, and Meg O'Hara is a painter, a Canadian landscape painter. She's got a small business. And she writes, hi, Jason. I have an idea for a story I think would be valuable and relevant to you, Entrepreneur Magazine and the Problem Solvers Podcast. That's the show I do for Entrepreneur. And then she says, here's what's going on with my business. All entrepreneurs had to be flexible during COVID. This is a story about how one artist in Canada benefited from the border closure. This just sort of intrigues me. Oh, how? Okay. When COVID hit in March, all ski resorts across North America shut down early. Skiers are a high-earning demographic. In Canada, they fall in the top 5% of income. Okay. Well, anyway, she goes on. What she tells me, because I remember this now, what she tells me is that her business used to be being hired by ski resorts to come and paint landscapes for their facilities. being hired by ski resorts to come and paint landscapes for their facilities. And when the border shut down and people weren't going to these resorts anymore, she had to come up with a completely different way of doing her business. And so she started to think, well, I can't work for these resorts anymore. They're not hiring me. But all these skiers who used to work at the resorts who have seen my work or who to ski at the resorts, who were maybe familiar with my work, they're not skiing either. They probably are sitting around wishing that they were skiing. They'd love something to see of their favorite ski location. And they also have money sitting around because they're not spending it on the ski resorts. So then she lists off the problems and the solutions in bullet points, which I love because she has listened to the show, the Problem in bullet points, which I love because she has listened to the show, the Problem Solvers show, which is structured in exactly that way. Tell me the problem. Tell me the solution that you came to. So she lists it off. Here are the problems. You know, the skiers can't come. People are spending more time at home. The solution. I create artwork for their homes that depicts their favorite views from skiing. So she goes on and on and on. I read this and I just think, you know, there is something here about what this person did to reinvent their business at a time in which one marketplace shut down, but it created a new one that I think people would like to hear. Because at that time, everyone was thinking about how to reinvent themselves and their business. And, you know, even though I reach people who have very complex and large businesses, sometimes it's really a beautiful thing to hear a single individual who does the simplest thing in the world, which is put paint to canvas, talk about how she did it for herself. Because you can extract these wonderful little lessons about how to reinvent yourself that I think are going to be relevant to a very broad audience. So Meg sent me that email. I replied and I said, I like it. And we did it. So that's a good example of someone who spent time understanding my work down to the structure of how I'm communicating and then sent me a pitch that very quickly and clearly seemed customized to me and told me her story in a way that I could imagine telling my audience. At that point, it's a pretty easy yes. That is an amazing example. I just took some notes on things that she did right based on things you've shared in the past. So even just from like the subject line or the first sentence, it was clear that she knew you. She knew you had this podcast, she knew the magazine and she even expressed this like specifically you're going to be interested in this. She mentioned how this she has like a story. She starts like immediately with a story. There's not like the value prop of the company. Here's what we do and here's why we're awesome. And then the lessons like the mission of entrepreneur you talked about is like insights and lessons that people achieve. And she just went straight to, here's what we've learned. So I could see why that resonated. Yeah, it was great. And the next thing that made it a real success, by the way, for her was that once I got her on the phone, she was, and I find this, this is a make or break thing for me because I can talk to somebody and then kill the story or not run the podcast, right? She was willing to be open about challenges. I mean, she had reached out because of challenges, but not everyone is. I will get a pitch from someone who is presenting like, oh, you know, we had this challenge in the business. But then when I talk to them, they act as if there was no problem or the problem was really small and their ingenuity immediately made this a very successful business. And that's not interesting to me because success stories are not interesting. They're not interesting to anybody. It's not useful for you to just hear that someone else succeeded. What's useful is for you to hear how someone else faced challenges that you faced and got through them so that you can see, aha, that's an interesting strategy to use for me. I hate success stories. I love problem-solving stories. And that's why when I talk to an entrepreneur, I expect them to be really open about that stuff. And if they're not, I basically lose interest. The hero's journey. I'd love to hear another example, but before that, hearing this, obviously it takes a bunch of time to do this for a founder.


Playing the long game of engagement (01:05:14)

I guess two questions, just like how many places should somebody probably try to reach out to, to give them a chance of being successful? And then do you have any thoughts on how much time they should put into something like this? I know it's a very broad question, but any thoughts there? Yeah, it's a really broad question. So again, this is in some way why, in a large way, why a lot of people hire PR, because PR can just move this along. They can reach a lot of people hire PR, because PR can just move this along. They can reach a lot of people very fast, whereas you as an individual cannot. One way to think about it is you're going to be on the hunt. You're going to try to make this work, and you're going to take a couple bets and hope that some of them pay off. Another way of thinking about it is, you know, this is a passive activity and I'll spend some time when I'm reading media, thinking about this, kind of developing an idea. Another thing that you can do, follow media, follow a bunch of writers and editors on social media. Meg, I can't remember the order of operations here because I know that Meg follows me on Instagram now because she's DM'd me many times and I respond to everybody. I can't remember if she followed me before, but she might have. And maybe she even DM'd me a few times. Usually it's like somebody's responding to an Instagram story or something. And I've seen a lot of people use this strategy with me and I think that it's a really smart one, which is basically before you ever pitch, just get me to recognize your name. Just engage in social media in a very casual way such that when you email me, I think, do I know who that person is? I think I know who that person is. It just Meg O'Hara, I think I know who that person is. It just makes it more likely that I'll open the email. And I see a lot of people do that. They'll spend a long time engaging with me on social media before ever pitching me. I know what they're doing. I understand that it's probably calculated. I still like it. It's smart because it means that by the time that they've reached out, I think, you have a pretty good sense of my work, which means that what you're bringing to me is probably in pretty good faith. And for that, I like it. It's a good filter. So if you've been listening to this whole thing and you're thinking, yeah, this is a tremendous amount of work. I have a new product launch, or I have a bunch of budget that I can spend on this. This individual kind of approach, it may not be for you. You might want to just spend a bunch of time instead interviewing different PR firms and find the one that seems most aligned with and understands your story and your vision and knows people in your space shortcuts a lot of this but even then even then i think that having heard this is really useful because at some point if the pr person is successful you are going to get on the phone with the writer or editor and it's very useful to understand how they think that they're not there to serve you right that that this this isn't a service that they're providing you so you better understand what they think, that they're not there to serve you, right? That this isn't a service that they're providing you. So you better understand what they're entering into this with and what they have in mind. When they're asking you questions, they're asking questions thinking, this is what my audience is going to be curious about. This is how I'm going to drive this person in this interview towards the kinds of insights that my audience are going to find gratifying. So the more that you understand who you're dealing with, the better. And also just having done it yourself, you'll better understand what to ask our folks, how they're going to work, find opportunities to improve the way they're operating. On the question of quantity, say you're doing this, say you're spending the time, I'm going to really invest in understanding Jason and whoever else.


The quantity of outreach (01:08:57)

Is there like rule that I need to recommend, like try to do this for three publications to get one? Or is it five? I don't know. Is there anything there that you could recommend? So it's really dependent upon how easy you are to write about. I mean, I just sort of like, right? If you are a, How easy you are to write about. I mean, I just sort of like, right? Like if you are a, if you are a, like some kind of B2B service, especially in some kind of very niche or wonky space, it's going to be really hard for you to get, like so hard that it might actually not even be worth trying. Because there are other things that you can do, right? Things that we haven't even talked about yet. Like you could say, you know what, screw it. I'm not going to try to get coverage for my company. Why don't I just try to position myself as an expert, right? Totally different kind of approach, right? Where instead what you're maybe trying to do is just hook onto the news, try to get a quote or a perspective to a reporter who might be writing about something. You know, I get these all the time you know some something breaks some some some news breaks and People start reaching out to me and they'll say, you know, this just happened in the news and my client or sometimes just the individual You know, I have this insight into this and here's what I would say if you want to interview me It's not gonna be a feature about you. You're going to be the subject. There's no photo of you. You might get a quote. You might get a quote in a story, which again is all you need to be able to say as featured in on your website. So that's the reason why people do that. So sometimes it's about that. You could just be a writer. You might try to just pitch authoritative articles by you to different publications, get yourself out in that way. Sometimes again, you're not going to be able to be easily written about. And sometimes you are. Sometimes you made some insane technology that everyone's going to be talking about and it's going to be super easy for you to get press. At one point your hit rate is going to be much higher. That's why going into this with really realistic expectations And if you're going to work with PR, having PR who can set and hold you to those realistic expectations can just save you a lot of heartache. Along the same lines, there's always this idea of exclusivity and people want to write first about a thing.


Managing Press Expectations And Opportunities

How to structure multiple pitches (01:11:11)

Say you haven't, you talked about like an awesome technology. Do you have advice on, do you just pitch the same thing to all of them and they hope they all write about it? Do you pitch them different stories? Do you offer one an exclusive? Any advice there? Everyone has a different approach to this. The number one rule here is just don't do it in a way that the people in media feel like you're playing them because they won't have tolerance for it. I would rather walk away from something like this and do some funny dance with somebody. So my favorite version of this goes like this. Actually, there's a founder who recently, I met him years ago. So when he reached out, I recognized the name immediately. And he reached out and he's like, hey, we did this really interesting thing and we haven't told anybody about it yet. And I'd love to see if it's a fit for entrepreneurs. So I hop on the phone with him and he tells me. And I'm not going to tell you what it is yet because we haven't run the story. But after 15, 20 minutes, I say, yeah, you know what? This is a really interesting story. And frankly, I know other media outlets are going to be interested in this too, particularly because there's a finance element to it. So I think the Wall Street Journal and Bloomberg and those kinds of places are going to be interested in this. He wants to go to Entrepreneur for whatever reasons he wants. I mean, I think probably two, because number one, he wants to position himself towards that audience. And then number two, there's a trust factor. He knows me in a way that he doesn't know the editors over there. And so he feels like I'll probably treat the story more carefully. So we worked out a deal, which he proposed. And the deal is that we'll get the exclusive. And there's going to be like a three hour window after our story runs. And then they're going to start responding to everyone else. And then they're going to start responding to everyone else. Then they're going to start talking to other people, or maybe they'll even line it up and reach out to some other media. That's fine with me. I understand. We're going to create a little embargo window, and we'll go first, and then they're going to talk to everybody else. Sometimes you can offer an exclusive to someone in that you're going to talk to everybody else. Sometimes you can offer an exclusive to someone in that you're going to release the news to everybody, but only one media outlet is going to get the interview, which works really well if you have a big personality. So for example, recently, a company that Mark Cuban has invested in offered us that. They're like, we have this news, we're going to reach out, we're going to send the news everywhere, but we're going to give you the exclusive interview with Mark Cuban. He's going to do one interview and he'll do it with you. You can parse it out in any way. You just want everyone to feel like you're being upfront with them. And that they're getting something special as much as possible. That makes sense. You touched on this relationship piece and that's something I wanted to ask.


How to engage with the press (01:14:01)

It feels like in tech, a lot of reporters end up writing a negative story because a lot of times that's what people want to read. Why is this destroying the world? Like I actually had a fast company do a thing on me and I talked to the reporter and I had no idea, was he going to just completely tear me apart or is he going to be really friendly and positive over what I'm doing? And I have no idea. And it just comes out. It's not like I look at it before it comes out. So do you have any just advice to give you a set, help you know if this is going to turn into something positive or negative? I know you have no idea. What happened, by the way? Was it positive or negative? Super positive. I was very happy with it. Yeah. Okay, good. Good. I'm glad to hear that. Yeah. So part of it is the publication itself, right? Entrepreneur and I would say fast company are just sort of not in the business of running negative stories. And the reason is because it doesn't serve our audience. My audience is coming to me to learn things for their business. Tearing somebody apart just doesn't help them in any way. Part of it is just like what ecosystem are you dealing with? You can also look at the past work of the writer. And if you work with a PR person, it's funny because occasionally somebody has like accidentally forwarded this to me and I'll see like the dossier that a PR agency will put together on me. But like a PR agency, if they set you up with an interview with someone, they'll usually do some digging and they'll find, you know, what does this person usually write about? What kind of stories they do? What are they generally interested in? So you can have a sense, right? Like, what kind of thing are they doing? And, you know, past that, I think there's also a question of like, well, what are you doing in the world, right? I mean, if there is something somewhat controversial about you, and especially if you're engaging with an outlet that is interested in that kind of stuff, there's a halfway decent chance they're at least going to explore it with you and ask you about it. And if you're like weird and cagey with them, they're going to think that there's more to it, and they're going to start start digging more. But the ultimate answer here is that every part of this, and this has come through I'm sure in our whole conversation, every part of this process is really out of your control. Does somebody pay attention to you? What do they write about you? When do they write about you? All of it is outside of your control, which again is the reason why it's not smart to think about press as a primary strategy for driving growth. It's a good add-on, but these people are going to do what they're going to do. The best you can do is read the tea leaves. Will Barron Yeah. It was a very weird... I don't get press often. It's not something I pursue, but it was just like, this is wild.


Anticipating the story’s direction (01:16:37)

I'm just going to talk to this guy and then something will come out. I have no idea what it might be. Like you might have things wrong. Cause I didn't get a chance to review and might skew things, but it's like a strange experience to go through, but it all worked out great. Yeah, it is. It's very strange. It is. It's strange. And I, and I find, I find that people often don't in, in, in business, people understand the structure of what's happening. They understand that we're a business magazine, we're going to write a story about a business, it's going to take a certain form. But I've done a lot of different writing and I have had the experience many times over my career where I'll spend a lot of time with people and they will have really no understanding of what it is that I'm doing at all. They can't conceptualize it. And then the story will come out and then they'll always reach out to me and they'll be like, oh, now I finally understand what you were even trying to do. It's fascinating. It is a vulnerable experience and you have to know that. And the more you try to control it, the more the reporter is going to be annoyed at you. And the more, in fact, the reporter might try to take a shot at you in the story as a result, because they found you too controlling, because they felt like you had something to hide. I understand this is not a comfortable thing. You have to go into this being vulnerable, and you have to know that there's a chance that it could blow up in your face. That's the price that you're paying for reaching their audience. Great advice. How about we do just one more example of an awesome email pitch that you got, and then we get to our very exciting lightning round. I'll tell you about a pitch.


Sometimes you’re not the story, but you can be part of it” (01:18:26)

I don't know that I have it in my inbox still. Do I? No, it's not there, sadly. I'll just tell you about it. But it leads to something that is another way of thinking about getting press, which I think is really important for people to remember, really. So far, Lenny, we've spent the majority of our time talking about press in the form of some kind of feature on you, writing about press in the form of some kind of feature on you, writing about you or including you in some kind of prominent way in a story that's basically highlighting the thing that you wanted to get out there, your product or something about your business, something, right? And then we talked a little bit about another way of doing it, which is sort of putting you out as an expert in authority there's another way of thinking about this which is that you can either create or present context in which you just happen to be a part so here's the here's the story pitch that I got that leads into this okay so this is years and years and years ago I just started a at FastCut or at Entrepreneur. And I hear from a guy named Fred Ruckel. And Fred Ruckel has got a cat toy and it's called the Ripple Rug. And it's basically like, imagine a rug and then another rug kind of on top of it, but ill suited so that the rug is lumpy. There's a lot of lumps and there are holes. And this is for a cat, right? To kind of crawl in and out of these spaces and bat and do whatever cats do. I don't know. I don't own a cat. And so he wanted to tell me about the sales of this Ripple rug and about how the sales are skyrocketing and all the things that he thought made it special. It's made out of recycled bottles and all the things that he thought made it special. It's made out of recycled bottles and whatever the stuff, right? Made in the USA. All cool stuff, but not relevant to me because we're not Cat Toy Monthly and we're not reaching a whole bunch of cat owners, not that I know of. And so I replied and I said what I usually say, congratulations on what you've built, but it's just not a fit for coverage. Now, Fred stumbled his way into this, but he did really a very smart thing because what he responded with was he said, totally understand if you're ever interested in learning about a gigantic scam that's happening on Amazon and eBay that we've been caught up in, let me know. So, you know, it was like, oh, well, yeah, I guess I am interested in hearing about that. So I said, tell me more. And he sent me this long email Fred loves long emails and I got him on the phone and had him explain and finally I understood it so this is and maybe people are familiar with this but this is a this is was sort of known as like Amazon to eBay arbitrage so basically the idea here is that Fred is selling his ripple rug rug on Amazon, or at least he was then, I don't know if he still is, but he's selling his Ripple rug on Amazon. But there are a lot of people who are copying the listing for his Ripple rug and making their own postings for it on eBay. And they sell it for a slightly higher price. So let's say that, and again, I'm making these up, but like, let's say that Fred is selling his Ripple rug for $30 on Amazon. So somebody will sell it for a slightly higher price. So let's say that, and again, I'm making these up, but let's say that Fred is selling his Ripple rug for $30 on Amazon, so somebody will sell it for $40 on eBay. And then somebody buys it on eBay. They find it, they buy it on eBay. They pay $40. So that person gets $40, takes 30 of it, goes to Amazon, buys the Ripple rug, and then just has it shipped to the buyer. And so it's arbitrage. And you might think, well, why would Fred care about this? He still gets the sale. The reason he cares about this is because the Ripple rug shows up at the customer's house, and it shows up in an Amazon box, even though they bought it on eBay. And they think, why did that happen? Amazon box, even though they bought it on eBay. And they think, why did that happen? And then the next thing they do is they go to Amazon and they discover that it's cheaper on Amazon. And now they feel ripped off. And who do they feel like they got ripped off by? Fred. Because they don't know about the Arbor Charger. They don't know that they exist. And so this person who has at this point opened the cat toy and probably had their cat roll around in it now shoves the whole thing back in a box and returns it and Fred gets dinged. And that's why he doesn't like this. And he has tried and tried and tried to get Amazon and eBay to stop this. But he said like they just nobody seems to care. And all these small businesses are losing tons of money on returns because of this. And I had never heard of this. And I thought it was fascinating. It's like a problem small business owners are dealing with. And so I was like, Fred, do you know other people who are dealing with this? And he's like, yeah, because I talk to them online all the time. And so he sends me off. And so I reported this whole thing out. I wrote this like 3,000, 4,000 word story on this thing. And Fred was the main character because he was the way to understand this problem. And I did all the reporting and I contacted the platforms and I contacted the people who make the arbitrage software. I did a whole report. But Fred got his press because sometimes, and here's the lesson, sometimes you are not the story, but you can be part of the story. but you can be part of the story. And sometimes that means, Fred stumbled into it, but I get plenty of people who reach out and maybe they have a real estate startup and there's something really interesting happening in the real estate space. And they reach out and they tell me about this really interesting thing that's happening in the real estate space and the role that they happen to play in it. And now I think, oh, well, that's interesting. Maybe there's a story about that. My wife, the freelancer, Jen Miller, she's done this many times where like she once did this story about there was a bunch of startups that were all related to helping people like prepare for death in some way or another. She's not going to write about one of them. But when somebody reached out and said, hey, here's a trend happening and we're one of them. Well, great. That's an interesting story. She wrote that and the company that reached out to her got prominent billing because they were the ones who reached out. Barbara Corcoran, you know Barbara Corcoran from Shark Tank?


How Barbara Corcoran became relevant (01:24:12)

I think so. I think so. Yeah. She's been a regular on Shark Tank since the very beginning. Mm-hmm. And she made her fortune by building a real estate company called Corcoran, Realtors, buy and sell property. And the way in which she built this company is fascinating. So Barbara, before she was Barbara Corcoran of Corcoran Realty, Barbara Corcoran was random New York City realtor, Barbara from New Jersey, and she was trying to figure out a way to distinguish herself from the Nass's. She came up with an idea which was to take her own sales data, right? The only window she has into the Manhattan real estate market at that time is what she is buying and selling, or what her clients are buying and selling, what she is facilitating. She has that data. It's going up or down relative to last year. She puts all this data together in what she calls the Corcoran Report. And she starts sending the Corcoran Report out to the New York Times and the New York Post and whatever. And because nobody else at the time was putting together a report on the health of the Manhattan real estate market, everyone started reporting on the Corcoran report as if it was an authoritative thing. And it's produced by Barbara Corcoran, which immediately put her in the position of being an authority in this space. And that was so smart, and I see it happen all the time. My inbox will also be filled with, for example, a company that a company that specializes in remote work consulting. Especially remote work consulting, you can hire them, it's a B2B service. It's hard to get press for that. Here's what they do. They pay a surveying firm to find all sorts of things. The top states for remote work, the top companies for remote work, the top whatever for remote work. And they produce all these surveys, and they send the surveys out. And the surveys get covered, because now they're creating a piece of news. They're creating some context in which they just happen to live in. Hard to write about them, this random company, but you write about the survey? That's interesting stuff. Oh, turns out that Utah is the top. I don't know if that's true. Is the top state for it? That's something that people will write about. You're giving people things to write about. And then once they do that, you are a part of the story. I get those pitches all the time. I occasionally bite on them and Fred from Ripple Rug got himself a big feature as a result. That's an amazing other strategy. And I imagine if I was a founder, I'd be like, hmm, what trends can I think about that I can tap into? Yeah. And sometimes you have it in your own data, right? I mean, if I was a founder, I'd be like, hmm, what trends can I think about that I can tap into? Yeah. And sometimes you have it in your own data. If you have a lot of data, you might... Zapier. Zapier is a great example. I get a pitch from Zapier every single year about the fastest growing business apps of the year based on Zapier data, because they see. They see what people are using and they just compile that together into a top 10 list and people run it. It's very smart. Amazing.


Jason’s parting advice: “Be human” (01:27:10)

So we've gone through all three steps. Is there anything else that you wanted to touch on that we haven't touched on? Anything else that you think would be really valuable for founders or product leaders trying to get press that we haven't already shared? This has come up in different ways, but I'll just put a point on it as a maybe final way of thinking about this. Be human. Be human, right? Press releases don't work because they are not human. And I don't like interviewing people who are on talking points because that's not human. You're ultimately engaging in a human business. A subjective decision is being made about how to serve an audience of humans. There's no right or wrong. There's no way to know. Media is a sort of barely data-driven industry because every story is kind of different. It's like, it's hard. It's hard to optimize the product because the product changes every minute. And so you're dealing with humans. And the more that you can be human in every step of this process, when you pitch, write a human email. Don't write a thing that looks like it came off of, you know, some marketing copy. Write a human email to another human. And then when that person engages with you, be very human with them. I mean, like Lenny, the reason why that Fast Company reporter liked you, I am very sure, was because when they got on the phone with you, you were just like a normal nice guy. Like if you presented yourself differently because you just wanted to frame yourself in some way or you felt protective or something or whatever it was, the reporter would have thought this guy is a dick and he would have written a totally different story. Be as human as you can and you will be dealing with a human who will receive that. Amazing advice.


Quick Question Round

Lightning round (01:28:59)

With that, we've reached our very exciting lightning round. Yeah. Are you ready? Let's do it. Let's do it. What are two or three books that you've recommended most to other people? Andrew Chen's The Cold Start Problem has come up over and over again for me because they're just really great lessons about network effects. And I've been having a lot of conversations about anxiety and perfectionism with entrepreneurs lately, and a book by a psychotherapist named Katherine Morgan Schaffler called The Perfectionist's Guide to Losing Control, I think are just a really great read. Super cool. What is a favorite recent movie or TV show that you've really enjoyed? Movie? I don't get to see a lot of movies these days because I have two little kids, but I took my eight-year-old to see the new Teenage Mutant Ninja Turtles, which was great and a really nice way of like, I loved them as a kid and so it was cool to see the modern version. And then my wife and I just finished Better Call Saul years late, but it was just perfect. I haven't watched that series yet. I loved Breaking Bad, but- Oh, it's worth it. You got it. Okay. Damn. Another series I got to get started on. I know. It's too much. Too much television. So I usually ask this next question to like product leaders and growth people, but I'm curious what the answer for you would be is do you have a favorite interview question you like to ask people you're interviewing? Usually it's about people you're hiring. Job candidate. Yeah, that's the ideal, but take it either way. I'll take it a little bit different because we've been talking about press. This is a really great strategy for interviewing people. And I'm going to tell it to you because I think that it's also good in any other context. And it might be a thing that somebody will do to you in an interview. My favorite strategy for interviewing people is to throw a theory at them. And I don't mean like a theory of the world, right? I mean that maybe 10 minutes in after they have told me a couple different things and answered some different questions, I'll make a connection in my head. And I'll say, you know, I want to run a theory by you. Do you think that the reason why you're really interested in this or you made that decision is actually because of this other thing that you told me a little bit about? Like, you know, you're listening. It's really active listening. You're combining things together into some theory. You're listening. It's really active listening. You're combining things together into some theory. And the reason why the theory works so well is because it forces people to think in real time in front of you. And I like that because I often interview people who have been interviewed a million times before, right? Like, you know, I interview Jimmy Fallon and The Rock or whatever. Like, they've been interviewed a million times before. So how do you get them to think in front of you? And the answer is to ask them the thing that they haven't been asked. And what I love about the theory is that it shows them that you're really listening and you're trying to understand them. And, you know, it's so interesting that you did that. And I wonder if it's because of X, Y, Z thing. That gets them to react in a really earnest, honest way. And I would say for what it's worth, that as a job candidate tactic, it's not that bad either. My favorite job interview that I ever did as a candidate that I didn't even get the job was years and years ago, I interviewed for a job at New York Magazine. And I interviewed with Adam Moss, who is not there anymore, but he was the legendary editor-in-chief. He made me, on the spot, drill down specifically into an idea. He was like, what's your favorite section in Strategist, which is one of the sections of the magazine? I was like, I really like the real estate section. He's like, all right, what would be a good neighborhood that we should feature in the real estate section? I was like, oh, I don't know. And I named a neighborhood. He's like, what would be like three good elements of that? He just kind of kept pushing me, drill down, drill down, drill down. And there was no right or wrong answer. He just wanted to see how I thought. And I found that to be incredibly powerful. And I do a version of that when I interview people. Awesome. I love that. What is a favorite product you've recently discovered that you really like? I use BigVu. I don't even know how to pronounce it. BigVu, B-I-G-V-U, all the time. It's a teleprompter app. I spent like $150 buying an actual teleprompter because I make a lot of video. And that teleprompter is, it's actually, for people who are just listening to this, I'm pointing at another desk across my room where it's sitting there and I've never used it. And the reason is because then I discovered BigVu, which is just a app that runs a teleprompter very close to the camera, either in horizontal or vertical mode. And I've tested it out a million different ways, and it really works. You're reading it, and it really looks like you're looking directly at the camera. I love it. It has saved me so much time. That is cool. So you basically put your phone on your screen next to the camera or wherever your camera is. No, no, no. Well, this would be for if you're recording on the phone. Got it. So you're staring at the phone and it's telling you what to say. I get it. Yeah, yeah, yeah. So you write a script, right? And then you just import the script and then you choose the speed. You can futz with it, you know, how many words per minute. And then it'll run the text very close to where the camera lens is. Amazing. All right, I'm going to check that out. What is a favorite life motto that you like to repeat to yourself, share with friends, something that comes up a lot? Something that I've been repeating a lot to people is something that I heard. So I recommended Catherine's book, The Perfectionist's Guide to Losing Control. I met Catherine because we've since become friends, but I interviewed her for the podcast when her book came out. And we were talking about feeling overworked and being stretched too thin. And she gave me this question, which I think about almost daily, and I repeat to people all the time. And that is, what's the point of building something if you can't maintain it? And I love that question because I, like probably everyone listening to this, pushes themselves really hard. And at some point, you have to step back and think, am I building something where at some point there is sustainability for me here, or is this unsustainable? And what's the point of building something if you can't maintain it? It's like a great reminder for why you're building something and how you have to build it. I have a very similar quote that my sister's partner once said that has stuck with me forever, which is life is maintenance. Basically, everything that you buy or bring into your life, you have to maintain. Like we got a new air conditioner, now we have a guy that comes every year to check it. Got a generator, someone's got to check that thing all the time. We got a toy and I got to think about where does it go? And right, do we throw it away? Do we keep it? Like everything that you bring into your life you have to maintain basically for the rest? Yeah, that's really true. Yeah. So it's really, I think, specifically for work. It's like, you start a new project, you're gonna have to like, you're gonna have to maintain it, maintain it like this podcast, right? It's like, do you want to start a podcast and do it forever? Like that's Yeah, that's a part of it. Part of starting something is you have to maintain it. Maintain it. Like this podcast, right? It's like, do you want to start a podcast and do it forever? Like that's a part of it. Part of starting something is you have to maintain it. Yeah. You know, I know we're in the lightning round and we've defied the logic of lightning rounds, but I'll just add one other thing to that, which is that I had this interview. I interviewed Michelle Pfeiffer for the cover of the magazine. And one of the things that I thought was most fascinating was she started this fragrance company and it's called Henry Rose. And she said the major difference between making movies and building a company that she found was that when you make a movie, all the work happens in the beginning. You make the movie and then the movie is out and then you are done. You don't have to work on the movie ever again. And she was not really mentally prepared for a company being the exact opposite, that the launch of the company is actually the start of the work. And there's an endlessness to it. And she said that it took her like a solid year to adapt to that reality. And then it became fun. But I think it's a thing people forget. I love that story. It's cool that you got to interview Michelle Pfeiffer. Yeah, she's great. Final question. I was reading your profile online and you said that the only reason you were able to achieve what you've achieved in life and got to where you are today is something that you called the opportunity set B. Oh, yeah. Can you just explain what that is and why that is so important to you? Oh, yeah, sure. So in front of you right now, like you, Lenny, you, everyone listening, watching, there are two sets of opportunities. Opportunity set A and opportunity set B. Opportunity set A is everything that's asked of you. So if you have a job, it's what your boss expects of you. If you have your own company, it's what everybody expects of you. And doing good at those things is really important. That's a measurement of success. That's opportunity set A, everything that's asked of you. And then there's opportunity set B. And opportunity set B is what's available to you, even though nobody's asking you to do it. available to you, even though nobody's asking you to do it. And that could be, again, if you have a job, that could be taking on new responsibilities or joining a new team or something. But personally, it could be pursuing a hobby. It could be starting a podcast because you like listening to podcasts, anything. What I have found throughout my own career is that opportunity set B is always more important, infinitely more important. Because the thing is that if you only focus on opportunity set A, then you are only qualified to do the things that you're already doing. But opportunity set B is where growth happens and where you push yourself in different directions. And I found a long time ago that it was just really helpful to think about these two things. Oftentimes, maybe we don't do opportunity set B because we don't know how it's going to pay off or we don't know where we're going to find the time. But I have always found, always, that engaging in these things of what is available to me, what's available to me right now around me that and there's nobody's asking me to do leads to the next growth either because it because it turns into an actual opportunity or because it informs some future opportunity I got to entrepreneur magazine zero zero people when I became editor-in-chief, zero people said, you should hit the speaking circuit. You should get really good at being interviewed on podcasts. You should write a book. Nobody said any of that. My job was to make a good magazine and direct the editorial of the brand. But all those things were available to me. And once I recognized that, I realized that I can pursue them and in doing so also think differently about who I am. Am I a magazine editor? Not really anymore. That's one of the things that I do now. I think of myself as an entrepreneur, as a person who is now in the business of helping others. I'm an entrepreneur who helps entrepreneurs. That's what I think of myself as. And I only got there because I was thinking, I am here and therefore I can get there. Nobody's ever going to ask me to do it. I have to do it myself. It's the thing that I always think about. And it's the thing that keeps me up at night. What am I doing now that is leading me to something else? I'm the only one who can figure it out. Beautiful. It reminds me of a recent podcast guest's advice, which is the best way to track your progress in your career and in life too, is just measuring how many oh shit moments you have. Because those are the moments where you're growing, you're doing something. I think it, maybe it's an example of an opportunity he said B where it wasn't the default path. It's like, oh, I think I should do this even though it's really hard. Yeah. What a beautiful way to end it. Jason, not only do I want to start working on press, it feels like very achievable to get press now. Like that was really energizing. Like, holy shit, I could do this. I could just find some people, pitch them, and here's how I do it. So not only that, I'm going to look for some opportunities to be routes for myself too. Thank you so much for being here. Two final questions. Where can folks find you online if they want to reach out, maybe pitch you on their story? And how can listeners be useful to you? Oh, so Lenny, thanks for all the work you do, which I just really love, and for creating the space for me to share all this insight. How can you find me? Well, I'll offer two things. So an opportunity set B is like a good launching point for both of them. So I wrote a book, it's called Build for Tomorrow. It is meant for anybody who's going through any kind of change in their lives or their work. And there's an audiobook version that I read myself, but also hardcover and ebook. Just find it wherever you get books. And again, it's Build for Tomorrow. Opportunity Set B, that whole thing is actually a chapter in the book. So I go into a lot more detail there. And then if you want to get in touch and also get those kinds of things, I have a newsletter which is called One Thing Better each week, one way to improve your work and build a career or company that you love. Again, the kind of opportunities that be, that's the kind of thing that I put out. It's very much about the personal and emotional side of work. And so you can find that by going to the web address, onethingbetter.email. Just plug that in, onethingbetter.email. Just plug that in, onethingbetter.email. And I said that's a good way to reach out to me because if you get the newsletter and you reply to it, it goes to my inbox. I guarantee I will write back to you. Insight track. Jason, thank you again so much for being here. Oh, thanks, Lenny. This was so fun. Bye, everyone. Thank you so much for listening. If you found thanks, Lenny. This was so fun. Bye, everyone. Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review, as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode.


Great! You’ve successfully signed up.

Welcome back! You've successfully signed in.

You've successfully subscribed to Wisdom In a Nutshell.

Success! Check your email for magic link to sign-in.

Success! Your billing info has been updated.

Your billing was not updated.