Hear Web Smith share the story of 2PM, a newsletter for CEO’s, investors, creatives, marketers, and entrepreneurs with all the most relevant information along with an Executive Membership option with in-depth commentary, analysis, and robust databases.

There are a lot of newsletters today and 2PM is one of the absolute best. Web shares insights into the unique challenges of “scaling insight” - something that can be tremendously difficult to do - along with his evolving routine of staying sane which includes sleeping “a whole lot more these days.”

He is well on his way to building 2PM into what his goal is: to be the “go to source for the entire industry” . Hear the origin story, what got Web to where he is, and where he’s going next.

Show Notes:

• 04:43 - The birth of 2PM
• 08:08 - The impact of 2PM mentions to websites
• 10:30 - 2PM = Two polymaths. Commerce, Media, Finance, Agency work
• 12:15 - You cannot survive without a base knowledge that continues to evolve
• 15:00 - An inspiration for 2PM: Stratechery
• 19:30 - On Rogue: perhaps the most impressive product company you don’t really understand
• 36:20 - Learning what you don’t want from how others treat you
• 24:30 - The eventual impact of Joe Kennedy on Web’s family
• 36:20 - Learning what you don’t want from how others treat you
• 40:45 - Goal: Be the Go To source for the entire industry
• 46:30 - Scooter Braun!
• 58:30 - Bulletproof coffee: beware

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Kevin Lavelle: This is Kevin Lavelle, Founder of Mizzen and Main, and you're listening to Founders 15. Today is a particularly unique episode because Web Smith and I worked together in the early days of building Mizzen and Main. Today Web is the founder of 2pm, a newsletter for CEOs, investors, creatives, marketers and entrepreneurs with all of the most relevant information they need, along with an executive membership option with in-depth commentary, analysis, and robust databases. There are a lot of newsletters today. There are only a few great ones, and 2pm is one of the absolute best.

Today, Web is going to share insights into the unique challenges of scaling, something that's tremendously difficult to do. Along with this evolving routine of staying sane, which includes sleeping. He is well on his way to building 2pm into what his goal is to be the go to source for the entire industry. As a personal subscriber, executive member, and avid reader of the newsletter, despite unsubscribing to almost everything else these days, I highly encourage you all to check out 2pm.

Web, thanks so much for joining Founders 15. We've known each other for a long time. This is, I think, the first time we've had a recorded conversation, so this should be fun. So tell me. And for the people not familiar yet with your story, tell me a little bit about 2pm your journey to get here and a little bit about yourself personally.

Web Smith: It's a really great question. So I think it was like maybe late 2015 when I began to start thinking about 2pm, I was handling commerce at a publisher at the time and I realized that I was so focused on my my work and trying to navigate the workplace that I wasn't really staying on top of the industry and how the industry was changing in real time. All right. I said to myself, Well, how can I? How can I find a way to accomplish that for myself? What can I do to motivate myself to stay abreast of everything that's happening, to stay educated and all these things? And 2pm. became that solution for me. So I said, OK, if I read these 10 things a day, then you know, I'll be better prepared to navigate the company moving forward. So it started as a project to enrich myself academically and industry wise. And it just became sort of a thing where 10 people wanted to get the same email. And so I sent it to 10 people. I believe you were probably in that first 15, 20 or 30, and it sort of snowballed from there.

Kevin Lavelle: And so you are based in Columbus, Ohio. You've got two beautiful daughters. Tell me a little bit about the day in the life of Web at home.

Web Smith: Things are good. You know, it's been an evolution. It's taken a long time to get to where we are today as a family. But I'm tremendously proud of who those two little girls have become. Alexis is in the fifth grade. So technically middle school at her school. And Adriana is in pre-K, so they go to school together. And Alexis is obviously a kid that I brag about quite a bit. Just very, very proud of who she's become and how she handles herself. You know, she moves between a few different worlds, and so she navigates those worlds pretty well. Great academic student, straight A's. Great great athlete. Great person, great human being. Adriana is sort of the sort of the yin to your to her yang. And you know, her life is probably going to be a little bit different. She's rambunctious. She's passionate, she gets, she gets angry if she loses a race, you know all these things. You know, there are a lot of similarities between them. But I think that Alexis and Adriana are going to provide us a contrast that should keep us entertained over the next 15, 20, 30 years.

Kevin Lavelle: And your daughters have a unique story behind their names, right?

Web Smith: Yes. So my younger brothers are twins. They both live in New York. They, you know, they're 30, 30 years old. They still share an apartment together because I guess that's what twins do on the East River and their names are Alex and Adrian. So when I was naming my daughters, you know, Lindsey and I were trying to figure out ways to name them, that would make sense for who they were. You know, both their culture, their heritage. You know what we thought they were going to become? All these things and Alexis and Adriana just made perfect sense. The name just fit them really well, and we just ran with it.

Kevin Lavelle: That's awesome. So 2pm at this point in time has grown quite a bit. Started off, as you said, just a couple of people receiving a few links from time to time. And now it's one of the industry standards of newsletters and it's funny. There's always those people who start the wave and it feels like you really spawned helped spawn at least the wave of people starting newsletters. So talk to me about some context for where 2pm sits today. The site, you know, you don't have to share specific subscriber numbers if you want to, but the reach of it and kind of some of the things that have demonstrated just how important it is.

Web Smith: OK. Well, those are great questions. What I will say is typically if we featured an article at the top of the newsletter, you know that the writer or the editor of that article will reach out when the article is featured.

Kevin Lavelle: Because you're driving so much traffic to that, right?

Web Smith: So I take a lot of pride in that because to answer a few of your questions, there are a lot of newsletters in the space, some of which I'm friendly with, some of which I feel are probably more adversarial than they need to be. But I pride the company on quality, on objectivity, on consistency, and I think the combination of those things sets us apart from a lot of them. So staying focused, staying in our lane, not, you know, veering away from what got us started and avoiding politics both literally and figuratively and and just trying to maintain momentum and organic growth.

Kevin Lavelle: And it is a newsletter, but it's also become a business. How how have you structured the business of 2pm?

Web Smith: Sure. And that's where, you know, you mentioned earlier about Meghan and I, you know, we are solidifying ways to scale what we're doing. And I'm deliberately moving slowly here because I don't want to make a mistake. I plan on doing this for a long time. It's the culmination of a lot of my passions. So right now, I would say that the revenue structure is a split between recurring revenue monthly and that that comes by way of monthly subscriptions and yearly subscriptions. And then the other chunk of revenue is one on one growth consulting throughout the ecosystem that we've built. So if I had to explain that ecosystem, 2pm, which is short for two polymaths, touches several parts of commerce, media financing agency work, and we consult strong leading entities in all of those areas.

Kevin Lavelle: You know, I always enjoy hearing the stories of names, and I always assumed that the 2pm name was because you send it out at 2:00 pm every day, and I had no idea. I know you generally have sent it out around 2:00 pm, but I had no idea that it stood for two polymaths

Web Smith: Yeah, yeah. It's you know, the operation is built to take the person like you who's multitalented. You have to be to survive as the chief executive of a derby at this time and providing them the tools, the insights, the data to operate and to be, I guess, authentic in order to take an authoritative in whatever they're saying and whatever they're communicating to their C-suites, their investors, their media partners, so on and so forth. Things change so quickly that if you miss out on six months of developments, you're behind. I talked to brands that don't understand how to drive affiliate traffic. I talk to brands that don't know how to advertise outside of Instagram and Facebook, and it's just I, you just can't, you can't you can't survive without a base knowledge that continues to evolve, and I am hoping that 2pm helps people.

Kevin Lavelle: Yeah, and I can speak from authority. Having read, I think every newsletter since the first one, I unsubscribe from almost everything that I possibly can because I get too many emails as it is. Even though we use Slack and don't have any internal emails, but 2pm is something I read every single day and I'm clicking on at least half the links. And then, you know, if I don't read it for two days because I'm traveling, it's not one of those where I just say, I'll just delete it. No worries. And the content that you provide in there is extraordinary and seeing you guys expand, not just, you know, highlighting great news and developments and commentary from around the web, but that it's now evolved into this executive membership, where you're providing deeper level insights and combing through all this data. As someone who is time starved and has to stay on top of everything, it's extraordinary and I think at least half of my company has signed up for the newsletter as well.

Web Smith: That's awesome. That's great. That's what I want.

Kevin Lavelle: And it's working well from everything that I can see. So you have hired your first team member to help you grow the impact of 2pm and you are seeing the changes, obviously with from one to two is a massive change. How do you define the culture of what you're doing at 2pm?

Web Smith: So that's a great question, and I, first and foremost, we are our great friends. You know, her husband's my best friend, my wife and her work together. So there's a lot of familiarity there. That being said, it takes a certain understanding of how people operate outside of the workspace to guide how people should operate within the workspace. So she knows, she knows my limitations pretty well, both in professional endurance, temperament, all these things and I. I pride myself on knowing her limitations pretty well. And so we've taken the approach where I'm using my strengths. She's using her strengths. We're working as a collective and moving forward. We're going to fill in those gaps accordingly with the right people. I don't foresee 2pm being a huge company ever. I know this is going to be jumping around, but one of my inspirations for 2pm is Ben Thompson and Integrity. And it's a pretty in-depth newsletter. It's not something that you casually read, right?

Kevin Lavelle: No, not at all. It's a very intense newsletter, right?

Web Smith: And so while that's not exactly how I would prefer to digest information, I understand why people are so attracted to it. And from what I know about Ben, we've chatted a few times and he's been a supporter of 2pm, which is a tremendous honor. His team is no more than four or five people. And so, you know, he's doing millions a year in revenue. And you can't really scale yourself or your insights, so it becomes a situation where I have to find a way to scale everything else but myself with people that are much better at me, better than me, at everything else and in Meghan's helping me do that.

Kevin Lavelle: That's really cool.

Web Smith: Yeah, that's the culture finding ways to try to address each other's weaknesses and amplify each other's strengths in a way that's respectful and lasting. And I think that both of us have a long term vision for what this can be.

Kevin Lavelle: It's a unique challenge that you face when you say you can't scale your insights. Certainly, there are consulting firms that scale the ability to consult, but that's not one person's insights. You're just hiring other people to go solve problems in the way that they would solve problems, giving them some level of guidance. So it'll be really, really interesting to see this journey that you go on and you do have a good kind of corollary in what Ben has done on its trajectory. And as you said, it is, it is dense. This trajectory is one that I will plug into from time to time, but I do not stay deeply engaged in it because I just don't think I have the mental fortitude or horsepower to make that a daily read.

Web Smith: That makes two of us.

Kevin Lavelle: Yeah, yeah. Awesome. So you got 2pm off the ground and it is, as you said, an initiative at first just to kind of improve your knowledge and share some of that. And then it became your full time endeavor. And with something like a newsletter, you're not monetizing that right away. It takes a little while before you can get there. So how long did you go without paying yourself for 2pm or getting back to a point where you could say, OK, this is I'm at least making an effective salary for anywhere close to where I could be. Should I go get hired somewhere else?

Web Smith: Sure. Great questions. So I would say that I went, I don't know if the amount of days or weeks or months that I went, I went over 200 issues without paying myself. So that was a test of endurance. It was, “do I really want this enough?” I think that throughout moments of my career, I've shown a lack of endurance, and I wanted this to be something different. So I sort of put myself through the paces like, am I really willing to go through this for the next five 10 years and make this become? And if I am willing to do that, then that means I'm willing to put in the groundwork completely without ever taking a dime. And that's what I was allowed to do. That's what I accomplished between late 2015 and literally January of 2018.

Kevin Lavelle: That's absolutely amazing. So to get you've had several entrepreneurial journeys over your career. Who most inspired you along the way early on or kind of as a true north and certainly there are a lot of people you and I have talked about that we look up to and we admire for their entrepreneurial fortitude and what it takes to make anything happen, let alone doing it several times over who has most inspired you personally or from a kind of famous person level.

Web Smith: Well, I would say personally, I think, you know, the answer to that it's Bill Henniger. Just the way that they've moved through the muck over the years. Has been extraordinary. I don't think they get enough credit.

Kevin Lavelle: Yeah, and to that point, for those people who are listening here and don't know who Bill and Katie are, they're the founders of Rogue. And I mean, they've built something that is one of the most impressive companies to me in modern times in terms of everything from the ground up.

Web Smith: I would agree. I would say from a, I guess, a celebrity standpoint or a famous person. I look up to famous people, but I do look up to historical figures and I'm going to name a person or two. That will probably be a little bit edgy, and I'm not not going to cite their business acumen because I don't necessarily approve of their business acumen. I approve of how they shaped their families. So in that context, I would probably say Joseph Kennedy and Fred Trump.

Kevin Lavelle: Drumroll, please, that was not what I expected to hear, that is that is impressive. So because some people's jaws probably just dropped. Go ahead and explain.

Web Smith: You know. We give JFK his generation of family members a lot of credit. And if you go back and look through how they were enabled to leapfrog into the national spotlight as politicians and business people and socialites and all that, a lot of that was by the will of their their father and the resources that he provided them, the umbrella that he provided them, the safety net that he provided them. Without business, they don't become what they became so fast. They went from zero to 60 in a generation.

Kevin Lavelle: Yeah, absolutely. And in the highest level of it, in and in every level, politically and professionally, wealth, all of it.

Web Smith: Yes, and to a greater extent, you know, I can't say I agree with everything that the man did or everything that his family's doing. But Fred Trump completely just leaves Joseph Kennedy in the dust. You know, I can't believe I'm saying this, but I was born to two immigrant parents. Fred’s empire was sold for nearly a billion dollars after we were in high school. He did it very quietly, a lot of other people around him took the shine, whether it was his sons or whomever. But he did it and he did it quietly and his growth was substantive. He made a lot of bets. Some bets failed. Some bets did not fail. And he silently built an empire that everyone around him took advantage of. Not saying that. Well, they kind of did. But, you know...

Kevin Lavelle: They were able to lever up on.

Web Smith: Right. And I value that. But those situations are part of my motivation for what? Keeps me up and keeps me moving forward and keeps my head up when I fail or keeps my head steady when I succeed.

Kevin Lavelle: And the interesting corollary there is when you think about the immigrant parents who built an empire and son became president. Your dad was one of the first African-Americans in the Coast Guard academy. Correct?

Web Smith: Correct. And really changed the trajectory of that institution. I think that he would say he probably didn't do enough.

Kevin Lavelle: I think I think people like your dad will always say that, but he certainly did a lot.

Web Smith: I think that we've had this conversation or, you know, without Joe Kennedy, there'd be no JFK. Without JFK. There wouldn’t have been a speech in the U.S. Coast Guard Cutter Eagle, where he required the academy to find black men. Back then, it was only white men. Without that mandate, you know, they wouldn't have found my father in the ghettos of Houston. He did. He doesn't come from poverty. But you know, Texas back then, they didn't have the choice as to where they were going to live in Houston. And without that sequence of events. You know. College wouldn't have been a sure bet for me. Right. And so, yeah, I'm obviously a big fan of history and history's impact on history isn't always pretty. You know, you and I both believe in nuance quite a bit. And I think that, you know, I owe a lot to that JFK speech. And so that JFK speech happened because of his dad.

Kevin Lavelle: So Alexis and Adrianna, when you listen to this, this means you have to be president. Just I don't know if only everyone was tracking where I was going with that, but that's where the bar has been set.

Web Smith: [laughter] So I, you know, all jokes aside, I expect a lot out of them. They have tremendous talents. They have the foundation. They have the resources. I'm not going to push them in that direction. But I think they come home every night and they know that the next morning they have a responsibility to build on where we've come from.

Kevin Lavelle: Wonderful. I love it. So changing gears. What do you do to stay sane amidst all of the difficulties and challenges and chaos and kids and family and business? What do you do to stay sane every day?

Web Smith: Oh, you know, I'm at peace, Kevin. I do yoga two or three times a week, hot yoga at six o'clock in the morning. I sleep a lot more than I did. So I sleep probably six to six and a half hours a night.

Kevin Lavelle: That's still not enough, but that's OK.

Web Smith: That's a huge improvement for me. Yeah, I obviously train at least five days a week, probably six. I, you know, I know that I'm answering a few of your questions in advance, but I only drink a glass of wine a night. I haven't had whiskey in over a year. Actually, the only time I had whiskey was the last time I saw you.

Kevin Lavelle: Wow. I mean, I don't even know who you are anymore.

Web Smith: Yeah. So I think the combination of those things puts me in a space where I'm capable of being. More productive. A better friend, a better husband, better father, better boss, better partner. And you know, that's an evolution. So that's how that's how I'm doing it so far. I think that, you know, obviously mental health is a huge component in the stories that founders don't tell. And even when I'm in my lowest moments, I'm in my lowest moments for a much, much shorter time than I was even two or three years ago, which is funny given how much pressure I'm under entrepreneurially right now.

Kevin Lavelle: Yeah, and it's funny that I think sometimes the perception is that you shouldn't have those lower moments, but you're always going to have them. It's about how you manage, how you manage yourself and what's around you in that moment and how long they last. And that recovery, it's not about making sure that you don't have them.

Web Smith: Sure. It's like you said, I see it as an opportunity to recover, so if I'm there for 15 minutes, how do I make it 13 minutes or if I'm there for half a day, how do I make it three hours, right? And how do I make sure that I don't self-destruct in that three hours? I think that's the cycle that you have to break. Not only as an entrepreneur, but as a person. And I think that over the last several years, that's something that I've been focusing on. You know, as far as the bets and the risky bets continue.

Kevin Lavelle: Yeah, absolutely. So if everything would be OK while you were gone? What would you do for a month away from it all? And I know being the type of business that you are, technically you can work from anywhere, although I think people misunderstand or abuse that notion that, oh, you can do anything anywhere. It's not always that simple, but you are. You've pre-written everything. Everything's preloaded to post you've, you've done all your analysis and your team is going to handle anything that breaks while you're gone. What do you do for a month?

Web Smith: Oh, well, I'm not as international as you are, so I'll keep my options domestic. I would probably go to, you know, Martha's Vineyard, Nantucket or Montauk, but that's my training.

Kevin Lavelle: What time of year would you go?

Web Smith: Oh, that's a great question. I mean, I don't think there's a better time than early summer. It's the most lively. It's great. It's a balance between. It's a great balance between the people that live there year round and the people that are there to party or to experience the sights and sounds. I love it. It's, you know, if we could go there every six months, I would. I just have to convince my wife that that's where she wants to go.

Kevin Lavelle: Where does she want to go?

Web Smith: She is a tropical beach person, so she likes to go south. If we, you know, even if it's stateside or, you know, Puerto Rico, that's where she wants to go. So, you know, Miami, Naples, that, you know, I'm not a huge fan of frying in the Sun. Obviously, I'm dark enough.

Kevin Lavelle: So when you're in Montauk, when you're in Martha's Vineyard, in that area, what what what's a day look like for you? I know you obviously have a love of the water and sailing. Do you want to be out on the water every single day or is it kind of a mix? What's the ideal day in this month away?

Web Smith: That's a great question. I don't think that I need to be on the water. I need to see the water that is very important to me when I travel for work. I'm always looking at water, you know, riding bikes across the island or across, you know, the state parks or running or working out experience, experiencing great restaurants, listening to live music. You know what summer, you know? Lindsay met Meghan, and I went to Martha's Vineyard, and the last day of our trip, we decided to carry over to Nantucket. And for the first time in my life, I rented scooters like Vespers, and we took a vestibule for like three hours around the island and explored every crevice of the island, and it was like the coolest three hours of the entire trip. So that stuff is the stuff that really resets me. It's stuff. It's, you know, little spurts of fun that we remember very clearly. We still talk about it as a group of friends to this day. That's the kind of stuff that keeps me going.

Kevin Lavelle: So I visited Nantucket last September for the first time ever, and we landed and spent the next 24 hours trying to get back off the island because it was right when the hurricane, I think it was Maria, was coming to hit it. So I did not get to see much of the island, but of what I did get to see, I can understand the appeal of it. It's a pretty special place.

Web Smith: It is a wonderful place. I strongly recommend it. You know you're I know that you have a love for scooters. You know, get that vespa. Then, find the coast of the islands.

Kevin Lavelle: Excellent. So on a less fun topic, what do you feel like your biggest sacrifice has been in starting a business along the way?

Web Smith: Probably, probably my mental health, I mean, I don't know how much that comes up in conversation when you're talking to founders, but I had some tough times, man. You know, some really, really stringent moments where everything that I thought about myself was tested, everything that I wanted to do with my life. I, you know, there are times where I didn't think it was possible. And so I know that that's not necessarily an experience that people feel when they're working typical jobs and there's a foundation and salaries and for one case and the work is stressful, but there aren't moments where you're wondering how your kids are going to be fed. Well, I have a high stakes life, and I guess that's just the way it's going to be. And, you know, that presents both negatives and positives. And I have to learn how to deal with the negatives as well as I learned to deal with the positives.

Kevin Lavelle: You mentioned kind of sleeping more, making sure you're doing hot yoga, which is fascinating to hear when you think about the challenges in kind of helping manage the mental health and difficulties of being an entrepreneur. Was there a mentor of yours or somebody who helped? Kind of. Have you helped guide you along that path? Or were there just things in people that you kind of heard and talked to along the way that gave you tips and tricks to help reset?

Web Smith: I think, you know. When you're in a leadership position, it can sometimes be difficult to step outside of yourself and see how you're affecting other people. I think that experience. Interactions where I was told by. The context or by the interactions. Really shaped my like, really shaped my view on how much responsibility we have to be at our best as often as we can be, because without that perspective, you don't know how much of a detriment you can be on other people. That's something that I've learned in the last five or six years. That was a long overdue lesson being treated a certain way can really open your eyes to how you're treating other people, and it's your responsibility to take that education and adjust yourself as necessary.

Kevin Lavelle: Couldn't agree more. It's learning from what you don't want to experience that can be a very powerful educator along the way.

Web Smith: Indeed.

Kevin Lavelle: So let's talk about the growth of 2pm over time. Is there a moment that you whether something happened or you just stop to think about it for a second, you thought, Man, this is no longer me just gathering some links and helping people. I have a good open rate on the email, but you either got a big sponsor to come on board or a consulting client or kind of someone you really look up to gave you high praise and had one of their friends sign up. Was there a moment that something really started to change in the trajectory of 2pm?

Web Smith: Yes. So early on, a few things happen. Alibaba became involved, they became fans of a newsletter, and that helped accelerate things for time. I would say that my biggest inflection point personally, I don't think that people necessarily observe it from the outside. But internally it was very evident was acquisition interest. You know, a major newspaper began talks with me. I rebuffed those talks for a while. It's not something I'm willing to go down the path up again right now, at least, you know, a digital platform. Silicon Valley entrepreneur as they approached 2pm for acquisition and this all happened within late 2017 early 2018. And that's what I sort of confirm that there is a value for what I was doing or value up for what I was doing and that. At least some people saw it as a business that could scale to VC standards, and the question became like, Do I want it to scale that much? And I haven't answered that question yet.

Kevin Lavelle: It's a pretty significant moment when it's not some random person that says they want to invest, but a major entity or institution says we would like you to be a part of what we're doing here. That had to be. Well, you said it wasn't what you wanted. It still had to be surreal.

Web Smith: Yes, it was. It was very affirming. It opened my eyes. It didn't, you know, it emboldened me to continue the path to invest more money into it and both changing platforms, improving platforms, branding. You know, it's a continued evolution, but those are two of the things that pushed me in that direction. I've had, you know, the last moment was the last moment of the three I would. So I would sort of give a credit to, you know, an institutional investor reached out and offered to lead around. And again, like those are, those are great milestones. Going back to what I was saying about Bill like Bill Henniger and Katie Henniger, like, that's I'm going to try to do it that way and I'm going to see if that works. And if it doesn't, then I'll have another story to tell.

Kevin Lavelle: And what a story it will be. So knowing that this is something that you want to stay heads down in, you're not looking to get out of at any point in time soon. Where do you see this taking you in 10 years or what do you see this entity becoming over the next 10 years? And those can be two separate answers or the same?

Web Smith: Well, let's talk about the institution that 2pm could be. It could be the go to source for the entire industry. That's, you know, that's what I want it to be. So I don't know what that number looks like. I don't know if that's three hundred thousand senior managers and executives. Nationally, I don't know, but that's what I want it to be like. My singular focus is I don't know if that's going to be three years from now or five years from now or 15 years from now. But I do know that. The value that 2pm brings will be delivered in a way that's relevant to the Times as the company continues to grow. So whether that's an app or. Any fit, whatever the preferred means of communication is for that time. I'm confident that 2pm will evolve to meet those needs.

Kevin Lavelle: Healthy, a healthy perspective, and you know, it's as you said, it's not just the reality of what you're trying to build it to be right when you look at what Nike is to the industry, to the sportswear industry. They hold a very small percentage of the total sportswear athletic market, but they are the most dominant force in sports and culture today.

Web Smith: Correct. And so again, that's a great point, I'm never going to see it as a volume play. Never going to mass market it or try to drive numbers for the sake of driving numbers. I haven't paid for a single ad. It's all been consistent organic growth and retention. And I know that there will probably be a time where those two elements are strained. And I'll reassess what it means whenever that time comes.

Kevin Lavelle: So if you could go back and tell yourself something, one thing in 2015, when you're starting this initiative and obviously you've done a lot right along the way in terms of how you view it, the long term waiting to monetize in an effective way that is still brand, right? What would you tell yourself back in 2015?

Web Smith: I would say that one thing that's helped the company quite a bit is the writing in the original thought, and I don't think that I paid as much attention to it back then. So I would remind myself that, you know, writing is a superpower, and it's something that can really change how people view the company, how people are drawn to it. It's a great marketing tool. It's a great value add. And I would have started to prioritize that sooner had I known what I know now.

Kevin Lavelle: And maybe that would have been exactly what you needed. But it seems like waiting until the time that you did has worked pretty well. So that's all right. So it could be an extension of that last thought or something totally different. What has been your single biggest regret?

Web Smith: There was a short time when I almost quit it. If I'm remembering correctly, there was probably a time where I didn't send the letter for two weeks or two or three weeks, and in my mind, I was done.

Kevin Lavelle: Did you talk to anybody about it?

Web Smith: I did. It was a combination of just not having the time, being discouraged, not seeing growth where I wanted to see it. And I left, you know, for short term, I left it behind. And I think that that was a mistake. I think that part of the value of staying in this process, day in and day out is doing the work regardless of whether or not you want to do the work. And there's tremendous reward in doing the work when you don't want to do it. And so that's what I wish I would have told myself at that moment. I'm playing a really long game, and I think this is just the beginning. Who knows if someone better than me is going to move the ball forward when I'm no longer capable? Who knows? But I think that there's a need for what I'm doing, and increasingly I'm that thought as being affirmed by the industry.

Kevin Lavelle: Kind of digesting that the reality of, again, the impact that you've had on. I mean, look, how many newsletters have started in the last year. It's been amazing. Does that surprise you?

Web Smith: Oh, it doesn't surprise me, I think that, you know, people are going to run into the same laws that I did. I'm going to respect the people that push through them. I'm going to encourage them. I'm really excited that people see value in newsletters as a medium. I don't think it's as easy as people think it is. It's definitely not easy to be consistent over a long period of time. So I look forward to seeing if people have the ability to do that. And I obviously deeply respect the people that do because I'm friends with them

Kevin Lavelle: Who has been the subscriber, and maybe you don't want to share this, but who subscribed without you reaching out to them or someone, you know, reaching out to them and you're like, Damn, that's awesome.

Web Smith: Scooter? Scooter Braun.

Kevin Lavelle: That is awesome.

Web Smith: Yeah. Yeah, that's you know, I checked the list from time to time. And I'm always surprised when, like a big shot joins the list.

Kevin Lavelle: I remember early on in Mizzen, managing MailChimp and seeing who would unsubscribe, and it would be one of my friends like, I mean, was it that bad being a subscriber to Mizzen and Maine's newsletter? Has anyone, and you certainly don't have to name drop here, but have you had anyone unsubscribe or do you even look at specific unsubscribe as where you were? You would think to yourself, man. That kind of hurts.

Web Smith: Ever unsubscribe hurts. I think I've actually talked about it publicly before. I obsess over retention. I always question things like, what am I doing wrong? Like, why would you possibly unsubscribe? Like that letter to me? 10 hours? Yeah. Yeah. Yeah. There are people that I've known that have unsubscribed. Listen, I'm aware that people only have the ability to manage so much stimulus, so much information, so I don't take it personally, but it hurts, unsubscribes hurt. But when people don't open it, it can sting a little bit. But you've got to be. You have to be focused on what the end goal is, and you can't be that sensitive about it. Yeah, yeah. I'm a national person, so that's an adjustment that I've had to make.

Kevin Lavelle: One thing I've learned recently as to and you can see my click, see, you know, I'm still reading yours. This is not my subtle way of telling you this, but one way I have learned how I can not hurt people's feelings on unsubscribe is a Gmail filter, where I just auto archive, where I just auto archive their their thing that I might get a lot and that has that has given me some sanity.

Web Smith: Well, you know, one thing I can say about one thing I can say about auto archiving is that it opens the door to, you know, maybe you find interest in it again six months from now or, you know. Right? And so, yeah, I mean, it's better than nothing out there. But I certainly understand we have a finite, a finite time. We're very busy where we're family guys, we're fathers. All these things. Yeah, you can't get bent out of shape. About how, you know, by how people spend their time. But in the meantime, I'm going to continue trying to make their time better spent.

Kevin Lavelle: So when you think about day in, day out that this is, you know, this is the life that we live day in, day out. What brings you the most joy every day?

Web Smith: Well, I'll tell you this if I send 2pm out at. 2:00 pm Eastern on Monday. It sets my week up pretty well. So a lot of things have to happen. I have to be at home, which I travel every week. I have to be at home, I have to have my writing done essentially late the night before, and I have to essentially be done curating by 10:00 or 11 o'clock in the morning. And then it comes and it comes down to like a lot of development and design and all that stuff. Because the newsletters are HTML based. If I can do that, like I'm tremendously proud. Like I I like to text my wife and say, Oh my gosh, I got it out on time, she's like, I know I read it. You know, that's that's that's a good that's a good feeling for me.

Kevin Lavelle: So when we think about the joy in that. How about the opposite? Well, I guess maybe the opposite, the other side of the coin, what is one of your most embarrassing professional moments? And this could be with 2pm a mistake that you made or from from any of your previous jobs?

Web Smith: I'll keep it light. I mean, I think that if I make it, if I make a grammatical error and intro paragraph or title, I know that seems really small. But that's devastating to me because the list itself has so many people that I would consider to be infinitely smarter than me, but it's already intimidating to hit send. So when I mess up, it's like, gosh, like, how do I not? How did I not see that? Or how did Meghan not pick that up? Or, you know, it can be very awkward and very painful, and it may not be the answer that you're looking for. But one thing, one thing that I've sort of used to keep me going is I've had some tremendous conversations because of 2pm and we've talked about some of them offline. Like a lot of these folks probably wouldn't give me the time of day had they not been introduced to 2pm. And so, you know, there's a tremendous responsibility there, and I try to make sure that I'm perfect every time. And that could be a lot of work.

Kevin Lavelle: It's also remarkable how much easier it is to proof other people's work than to proof your own. I can look at an email that we've prepped and I can spot two mistakes immediately. But if I write something, you know, I've put it in there, that's a very unique aspect of writing that is, I think, misunderstood as to how difficult that can be.

Web Smith: Well, I applaud anyone that can do it well. Yeah.

Kevin Lavelle: So wide ranging question here. Do you expect to be doing 2pm or some offshoot of it for your whole life? Or do you think this will evolve into something else?

Web Smith: You know, ideally, I want to. I want to be able to embolden brands and the people that run them 2pm gives me the ability to do some of that now. I'm sure there will be elements of 2pm that grow to focus on that more and more. I can see that as a long term focus, whether that be in financing or in creative marketing, building the systems to embolden those types of companies to survive and thrive in the new economy. That's something that's something that's really important to me and I. I do plan on being in this business for a while and I never want to retire, but hopefully I'm doing this stuff on my own terms.

Kevin Lavelle: So I think it flows well into the final question, which is how do you want to be remembered?

Web Smith: You know, that's a tough question, I think I've succeeded publicly, I've I've failed very publicly. The one thing that's the most important to me is that at the very least, you have to be able to objectively say that I didn't. They didn't throw in the towel like I didn't stop trying or I didn't stop to make it stop. I didn't stop making the attempt, right. I think that's extremely important because there are numerous stories of folks that don't figure it out for a long time. But when they do figure it out, it has a tremendous impact not only on themselves and their families, but beyond their families. And that's what I sort of hope for. And that's what, you know, if I had it my way. That's what I hope people would say about me that they didn't quit.

Kevin Lavelle: Heads down, don't quit. So how can people sign up for 2pm?

Web Smith: You can sign up for 2pm at 2pm.com. The front page has a sign up embedded just plug in your name, your first name and your email address and we'll take care of you.

Kevin Lavelle: And of all the things that are most unique about you, it's probably your Twitter handle. And what is your Twitter handle?

Web Smith: [00:55:23] You can find my tweets on both economics and industry and socio-politics at @Web W.E.B. I'll never stop talking your ear off, so be careful.

Kevin Lavelle: It's a good follow, go give it a follow. So with those logistics and serious questions aside, it is time for the ever entertaining, rapid fire questions. How many hours of sleep a night do you get? You answered this already, but how many hours of sleep an ideal night?

Web Smith: Five to six and a half?

Kevin Lavelle: Amazing. And such a wide swing. That's a huge percentage swing given the amount of sleep you get. What would you use the gene editing technology for on yourself?

Web Smith: Oh gosh, I wish that I could dunk easier. I feel bad being the only athletic looking black guy that has a hard time dunking.

Kevin Lavelle: What is your favorite fiction and nonfiction book?

Web Smith: Wow, I. My favorite nonfiction book right now is probably The Restless Wave by John McCain. My favorite fiction right now is Fahrenheit 451.

Kevin Lavelle: Wake up and wind down drinks of choice.

Web Smith: I drink bulletproof coffee in the morning. I try to stay in ketosis until two o'clock in the afternoon, and I drink a glass of wine with Lindsey at night.

Kevin Lavelle: I remember the first time you had me drink bulletproof coffee I almost threw up. It is a serious thing the first time you have bulletproof coffee.

Web Smith: Yeah, it's different. Yeah, so it's bulletproof coffee with 15 grams of protein, which makes me sound psycho. But it's great. It does. It does its job. And, you know, I don't look like Charles Barkley right now, so that's progress.

Kevin Lavelle: I hope he's listening. I doubt it. What would your last meal be? And since it's your last meal, you don't have to eat healthy.

Web Smith: What about chicken and waffles?

Kevin Lavelle: There you go. What's your biggest pet peeve?

Web Smith: Wow, that's a tough question. You know, I'll keep it light. I hate when people can't parallel park.

Kevin Lavelle: Excellent.

Web Smith: I live in the city and if you live in the city and it takes you thirty five seconds to Parallel Park, move out of the city.

Kevin Lavelle: Get out of here. Get out of here. Or just rent one of those bird scooters, right? Favorite podcast?

Web Smith: You know, I listen to the daily. A lot of Joe Rogan. I listen to Joe Rogan a lot. I think those are probably, you know, those are probably my to go tos

Kevin Lavelle: Off all of the “I can't believe someone is wearing Mizzen and Main people” that I've ever seen wear Mizzen and Main, Joe Rogan has to be the coolest. The first time we saw him wearing it was on his latest Netflix special. He wore us on his interview with Elon Musk. He wore the pink Spinnaker super stretchy dress shirt and that interview got so much play. I got probably 15 people that texted me, I was like, Is that a Mizzen and Main shirt? Because Joe Rogan is wearing a pink dress shirt, which is pretty extraordinary.

Web Smith: It's one of the older ones too, wasn't it?

Kevin Lavelle: Yeah, it's like three years old.

Web Smith: Yeah. You know, Joe Rogan is so cool that he wore a dress shirt in a way that made it almost not look like a dress shirt.

Kevin Lavelle: Yeah, he never buttons the sleeves and collars at least two or three buttons deep. And I was talking to someone who knew him not too long ago, and they said they'd never seen him wear a dress shirt until he started wearing Mizzen and Main, which is pretty awesome

Web Smith: It's amazing. And that was an amazing interview. Yeah. I strongly recommend anyone that's listening to this. Listen to that interview because it was very eye-opening.

Kevin Lavelle: And terrifying.

Web Smith: And terrifying.

Kevin Lavelle: What percent of your monthly budget is Amazon?

Web Smith: I am becoming an Amazon junkie. I Prime now, everything. So if I had to say seven to 10 percent.

Kevin Lavell: What TV show could you watch over and over again?

Web Smith: Big Little Lies.

Kevin Lavelle: What is your favorite article of clothing? And I'm going to take away your option to say boat shoes.

Web Smith: Oh man, my 2pm Patagonia vest. I'm wearing it right now. It's not even cold in here.

Kevin Lavelle: You just move effortlessly between Silicon Valley and Wall Street.

Web Smith: Yes, I do. Perfect. No matter where I go, I'm on brand.

Kevin Lavelle: Do you love or hate cardio?

Web Smith: I hate cardio, but right before I was on the Mike with you, I did 30 minutes on the assault bike.

Kevin Lavelle: Excellent. Would you rather fight off 100 duck sized horses or one horse sized duck?

Web Smith: I'm terrified of rodents and bugs, so anything that gives me that sensation will put me at a disadvantage. I'm going to go with the horse sized duck.

Kevin Lavelle: What is your favorite destination to travel to?

Web Smith: So I'm going to go, I'm going to the other coast. I work in L.A. a lot. When I'm in L.A., I stay in Laguna Beach. They're all beautiful. Yeah. So there's a hotel there called the ranch. And it's amazing. Nice. That's where I go. And it's gorgeous.

Kevin Lavelle: And to close out, what is the best gift that you've ever received?

Web Smith: My wife got me a trip that we haven't gone on yet, and it's somewhere I've always wanted to go and I haven't even gone yet. But I think that's the coolest gift that I've gotten. We're going. We're going to France over Christmas.

Kevin Lavelle: Awesome, are you all four of you going or the kids staying with grandparents?

Web Smith: It's going to be Lindsay, Alexis and me. Alexis has been studying French for five years now. And so we thought that we, you know, we had to be fair to her and take her. So the youngest is going to stay at grandma and grandpa house, and we're going to lean on our daughter to translate everything for us.

Kevin Lavelle: That's going to be a really, really cool trip for her. What an experience. How long are you guys going for?

Web Smith: About four or five days? If I'm not mistaken.

Kevin Lavelle: Very cool. It'll be a beautiful two at that time of year. Excellent. Well, super super wide ranging and fun conversation. Thanks for taking the time to. I know you're not a huge podcast guest kind of guy. Think you've only done a handful or so? I appreciate you breaking that down for us and really excited to see the continued growth of 2pm and for everybody listening. If you are listening, then you're at least somewhat interested in this world. And so therefore I cannot recommend highly enough becoming a subscriber and executive member of 2pm. Check it out at 2pml.com

Web Smith: Thank you, sir.