The Business of Newsletters with Kendall Baker, “The Sports Newsletter Guy”

there's a very intentional push around soccer right now in the lead up to the 2026 World Cup we're three years out MLS has long been seen behind NHL but I think Messi is such a game-changing signing MLS is legitimately in the conversation in a way they haven't been so the field is going to be 48 teams it's going to be the biggest world cup ever put me on record every viewership record will be broken it's going to be huge welcome to the peel Where We explore the world's greatest startup stories I'm your host Turner Novak founder of banana Capital Venture Capital firm with the highest email newsletter open rate today I talked to Kendall Baker currently Kendall leads Yahoo's Sports newsletter business in 2017 he launched the first daily Sports newsletter called Sports internet which he sold to axios in 2019. before Sports internet he convinced the founders of the hustle to focus their online tech blog on a daily newsletter which he wrote for a year and a half before the hustle he produced SportsCenter at ESPN he spent nearly a decade at the intersection of Daily News and Sports in this episode is packed with insights on both we talked about the history of the newsletter industry and why the best writers delete more than they write he gives us a crash course on the sports media and newsletter businesses and shares how he secretly got on SportsCenter in 2015. he tells us how he got his very first dollars of sponsorship revenue for sports internet and why he decided to spend zero dollars on growth we talked through the process of selling Sports internet taxios why the commissioner of the MBA reads Kendall's writing why he thinks Yahoo is the next rocket the surging momentum in U.S soccer and the most underrated athletes today and of all time thanks to Kendall for coming on the show and to all the anonymous Sports VIPs for their great questions now let's jump in after a short word from secure frame long time listeners no secure frame is the automated compliance platform built by Security Experts I'm an investor in Secure frame and I highly recommend it to every founder I meet I found a friend of mine JJ Tang at rudely used secureframe to get sock 2 compliant in two weeks today Worley helps massive organizations like Cisco Nvidia and shell manage engineering incidents across their entire organization but back when we really launched signing publicly traded companies is a seed stage startup would have been impossible without secure frame's automated compliance software designed by Security Experts thousands of other customers like ramp Angelus and Kodak trust secure frame to get stay and automate their compliance with security and privacy Frameworks like soft2 ISO 2701 IPA gdpr and more check the link in the show notes to get set up on a demo with its in-house team of compliance experts and forward thank you secure frame now let's talk to Kendall Baker Kendall how's it going thanks for joining me today it's good man thanks for having me I'm excited about this I've been a Observer slash reader of your content for a while can you kind of give us a history of just this whole newsletter industry and maybe specifically what's going on in sports also if that's relevant sure yeah so I think I can speak to the newsletter industry pretty well just because I've kind of been there for a few of the different stages that I've seen I guess I'd start with saying the first time I became kind of aware of newsletters as a business model and not just kind of like something that a media company has or something that somebody writes but as a foundational piece of a business if not the entire business was the skim I had a friend working there this was um see I graduated college 2013 probably around right when I graduated colleges when I first became aware of it and what was the skim the skim was one of the first newsletters that was really kind of a daily newsletter product taking the biggest headlines explaining to you you know why they matter very brief it was definitely targeted towards women more so but they were the first really big I would say success story in terms of a daily news-based newsletter that was really their entire business they ended up building some things around that but still to this day it's very much like their core business model and that was the first time I became aware of that 2013 and I was actually working at ESPN at the time and funny enough which you know I ended up launching a sports daily newsletter but at that time I had the thought of what if you did this but for sports so that was always kind of in the back of my mind and ended up acting on it later but that was kind of so so 2013 I'd say was when you see kind of the skim I think there were a few others that were starting to pop up like oh wow you can build an entire business around a newsletter you can have a pretty lean team but also probably bigger than people think if it's just this one product so that's 2013. two years later I ended up at a company called The Hustle which at the time was a Blog we had like four employees it was a tiny business and a little apartment essentially in San Francisco and our newsletter at the time was more what you would see back then which was hey here's the best articles we wrote this week it was more of a curated list of our stuff as opposed to like original reporting that you hadn't seen elsewhere and I actually pitched the founders of the business on hey what if we did like a daily newsletter where we just covered the day's headlines kind of like the Skin's doing and there was a few others at the time so we ended up launching that 2016 and that's where I'd say you you start to see more of the skim copycats or just more businesses realizing that hey we have you know we're creating a ton of content and then we're putting that stuff into a newsletter and sending it what if we just sent the newsletter and I think you saw a lot more businesses realize you could have a leaner team you know in many ways cut through the noise I think one reason why newsletters have been so effective is people realize oh everybody's kind of overwhelmed with information even your own content if they're a big fan of your content why don't you just give them the best stuff to begin with or you can build into our business around it so that's 2015 you start to see more copycats so what was the business model then at the time did you just get a bunch of eyeballs certain amount of opens for email and you can kind of monetize with advertising exactly and and at the time and I think to to a certain extent this is still the case if not even more so you can just get higher C CPM rates on newsletters so if your business was hey we have a Blog and we're selling banner ads if you essentially then say well we're actually going to Pivot to a newsletter create similar content obviously a little shorter tighter you're going about it in a different way where you're sending one thing versus publishing multiple articles throughout the day you can essentially run the same business with more eyeballs ideally and higher CPM rates it was a kind of an easy pivot for some folks that's fascinating why were the cpms higher it doesn't it doesn't make sense it's a great question and I think many people would have many different answers I think my assessment is there was already starting to be and it's definitely even more so now this sense around the industry that nobody was looking at banner ads I think there was even like studies that came out that was like our eyeballs are now trained to block them out nobody's looking at them and I think there was something still and again it still feels like this is the case that was like kind of new and exciting about newsletters more of a community people were reading it it was more of a habit and I think a lot of it also was with newsletters you could kind of create more of a voice for your brand and I think advertisers were really really interested in putting themselves in that newsletter that you're creating that really had a voice really had a connection with the reader and that reader was opening it almost at a habit if you're doing a good job you know every morning with their coffee as opposed to maybe coming to your site but there was something I think attractive to advertisers about being aligned with this product as opposed to maybe a website yeah there's probably an aspect of the reason Facebook and Instagram ads do so well is people habitually open the app many many times a day email is probably the same where if you send someone an email they might not open it but they'll see that you sent them an email and they'll they're always returning so you can almost guarantee that people will read it and see it I mean look what I've always said about daily newsletter specifically and this applies certainly to weekly and whatever Cadence you do but but daily a daily newsletter in my mind is the most habit-forming media product there is even more than a daily podcast because you know a newsletter or somebody can open on their own time they can use it in the way they want to read every word they want to read a top story they want to read something and they end up down a rabbit hole it's more kind of Choose Your Own Adventure and I think people are much more likely to kind of open that out of habit every morning I have so many readers who tell me I re you know I read your newsletter every day over coffee where I read your newsletter every day on the train to work or whatever it is they know when to expect it it shows up in an app that they check frequently it also shows up in an app alongside their co-workers their boss their mom it's just kind of comes to them in a place that feels very organic and very much kind of one-to-one so back to kind of the history of newsletters 2015 uh you see a lot of companies media companies starting to use newsletters as their core business or one of their Core Business revenue streams and then I'd say between 2015 and now there's been this shift so first there was a shift to Media companies are doing this you know small to medium size maybe some big big media companies what if I did this on my own what if I did this with two three people really small one to three person operations that realize okay we can kind of create an entire news based media company with just a handful of employees I mean that's how morning Brewster it that's how I started Sports internet which ended up getting acquired by axio so it was basically hey I can kind of do the entire day's news myself or two people or three people and newsletters were the perfect medium for that so I think I'd say between 2017 maybe 2019 2016 2019 you started to see more people whether they were ex reporters and media companies or didn't really have any experience journalistically quite frankly um realized that they could start up and up a daily newsletter and grow it pretty effectively and then I'd say the biggest change I've seen has been within the last four years which I've kind of observed from afar because I've been working at a media company and not really in the weeds but definitely interested and following very closely which is now you have tools like sub stack you have tools like beehive that have made it way easier to start newsletters first of all they've also created a network effect that you saw happen with podcasts where you have you know what are the top newsletters you can see that on sub stack in a way that you can before you can discover new ones in a way you can before so there's this ecosystem that's been created and these tools that have been created that make it extremely easy to start a new letter and not just start it but then find similar newsletters share audience with those people and so what is kind of gradually become apparent to people is that newsletters are a very effective medium and what's happened recently is it's just become incredibly easy to start one and I wouldn't say incredibly easy but much easier to grow it and find new readers and I think people are just very interested in newsletters in a way that they weren't before in terms of kind of from a discovery standpoint what makes a good daily newsletter or just newsletter in general there's a few things I'd probably say one and this applies more to some people than others I think it depends on your subject matter but I think pairing a daily newsletter with a very distinct voice is extremely effective like I said before you're sliding into people's inboxes if you will you're sl you're sliding into their DMS and often you know a lot of newsletters come from your name some people still have it come for their company but for mine at access for example came from Kendall Baker and so you know you have somebody getting essentially an email from you why not lean into personality now I covered sport words and that's easier I think if I were covering politics for example maybe you don't lean as much into that because you know if you're a political reporter you don't want to feel you don't want to be the story you want to be as unbiased as possible so I think you know that gives you an example of like where it works better than others but there's always a way to kind of sneak your voice into their make it personal and um as somebody who's been writing newsletters forever and anybody who has been doing it can relate to this people can reply right to you and so again leaning into voice leaning into like hey there's a human on the other end of this I can't tell you how many people over the years will reply to my newsletter and then I'll reply back to them and they'll be like oh my gosh like you replied I'm like yeah this is my email you know what I mean and uh it's actually funny like the the best ones are when somebody replies you know hating on you or telling you how dumb this thing was and then I'll reply like thanks for the feedback like really appreciate it or something longer than that and then they'll get back to me oh my gosh I'm so sorry I didn't mean you know it's like the funniest interaction always because they expect like most things they don't expect a response they and maybe they don't even think it's anybody could ever see this they're kind of just getting it out whatever they need to get out and then I come back to them with like a nice little message and then they immediately retract it that actually helps though boost your deliverability in their inbox right like when people reply deliverability for sure like there but but also just the second somebody has a conversation with you they feel even closer to you and I don't have exact data to back this up but I promise you people who have interacted with me on my newsletter they've replied I've gotten back to them they become much more loyal subscribers because now they feel like a connection with me and there's actually you know I had I had one guy over the course of the last essentially five years reply to almost every single one of my newsletters and so I've never met him but we have this kind of like pen pal-like relationship there's another person who for a three-month span would grade every one of my newsletters on a scale of one to ten uh and it was just like kind of awesome and uh I you know I didn't want to read too much into it it's one person but when he gave me like a low score like I definitely was like okay like maybe something to consider but was it just a pure number or would you be like I give you a five because of this or a ten because sometimes there was like a reason but other times it was simply just like 8.2 .2 yeah uh it was pretty awesome but but so so that just kind of gives you a sense of like the relationship you can build with a reader with the newsletter and back to my point of voice like if you're gonna have if you're gonna build that relationship and lean into that relationship you should lean into who you are I think another thing that makes a daily newsletter effective and this is very on brand for my previous employer axios but it's true uh make it sure first of all over half of email subscribers this is data I've seen it could be different depending on who you are over half are reading on their phone um and so if you think about and this is true for article any anything any any reading being done on someone's phone if they can't see the bottom of the paragraph they're reading there's a much higher chance that they're going to jump ship because that's just how attention works now if somebody the second somebody gets bored if you're not immediately jumping them to the next thing jumping them to the next thing getting to the next thing the chances of them leaving is much higher and I think emails newsletters there's so many of them now a lot of people are inundated with them if you're not able to kind of deliver them your message effectively efficiently and kind of communicate to them like hey I value your time I know you're busy and that's why this is sure that's why this is the point I think it's really helpful I think people have a bad habit of writing too long you know kind of getting too obsessed with their own words and I've kind of grown to kind of be obsessed with deleting my own words and treating newsletters like every pixel matters if you will you know one of the great things about newsletters is they're extremely Bare Bones and they're extremely limiting you know some people will complain oh I wish I could embed video in my newsletter I wish I could do all these things and yeah that would be great but I think there's something to be said for the fact you can't do that so therefore you have to focus on the written content on the images on every small little detail and what happens is you end up treating it more like a piece of art than just like a blog post and I think that goes hand in hand with length if you're really intentional about every word you put in that newsletter every image everything is just really thought through you create something that's just a real joy to read and people can kind of look forward to reading it in a way that people these days don't look forward to reading much because everything is not everything but there's a lot of things are just really long you know it's a hard Truth for us to accept as writers but like there's a very good chance people are going to bail on you after the first paragraph yeah it's very counterintuitive but probably the top advice I get from or feedback I get from anyone how to be a good writer is Right less I mean it's true and I think you know like you take the New York Times for example love the New York Times but the New York Times almost trains writers in a way that they train riders to write for newspapers if you look at a typical New York Times Story the first paragraph is kind of like it's the person trying to win a Pulitzer Prize in my opinion that's how I describe to people it's like perfect words big words beautiful beautiful prose but like the the point of the story doesn't start till like the second paragraph in that's how newspaper writing was done you know you have to almost go to get on the front page you have to go long whereas I think that's actually counterintuitive now the best advice I give to people is like no actually instead of starting with that long winding nicely put together paragraph why don't you just start with what people click the headline for which is like what happened or what's important and I mean again very on brand with my foreign employer but actually part of the reason why I joined axios is I very much agree with this way of thinking which is people are busy the most important thing you can do to create brand loyalty with readers is just like value their time it's interesting when you talk about the New York Times Like there'll be times where I will read some you know New York Times CNN I don't know Legacy Publications I don't know how to refer to them and there's just some super juicy Stat or thing that's like buried two-thirds of the way through you can reverse engineer this so you know obviously in this example I'm about to give the New York Times to the hard work and so they deserve credit for it and of course you know nothing irks me more than when people potentially take something from somewhere else and make it very vague that they got it from that Source like be upfront with the fact that you know it's via New York like that's very easy to do and you'd be surprised how many players don't do it but like to use your example you know if I read an article like that New York Times it's a 1500 word piece and there was one stat in the middle that was like jaw dropping how I would reverse engineer that would be I'd share the stat and then tell people if you'd like to read the whole article go here right because some people want to read the whole article great but like if you surface the most interesting point most people aren't going to read the whole full article but at least they got that from it and then the people who do want to read the faux article make it very easy for them to do so it's kind of simple when you think about it but there are you know reasons why Publications don't do this and I understand those reasons but I just think if you're writing on the internet these days the single most important thing you can do is just learn to write shorter and learn to be more efficient with your words it is good feedback and after talking with us for a couple minutes it's made me reflect I can probably cut a little shorter I have a Weekly Newsletter that's probably how like about half the people listen to the podcast kind of from the newsletter it's not black and white and I also think that Weekly you know maybe we're looking for something different like I speak a lot to daily newsletter that's what I've been doing and that is really you really have to Value people's time because they're busy they're usually reading in the morning before they get to work they want efficiency they want like my readers for the most part want talking points so that when they try talk to their friends at work that day or whatever like they they're up to speed they're ready to talk about stuff weekly newsletters you know you can think about more like magazines maybe and therefore writing longer isn't necessarily a bad thing if you set the expectation of we all of our content is very long have you ever listened to the acquired podcast yes I have so they do like three four hour episodes you're not gonna finish those quick and you know you're going to learn the history starting from the 1800s of some massive company and it's going to be a thrill interesting along the way but it's not quick you'll learn a lot if they're all really they're all very well done and I know I mean they told me they cut so much like they'll go in and they'll record for a day multiple days and they'll cut it down to three or four hours so I think it's it's just like you want to keep your content high quality high quality and I think you made a really good point set the expectation you know as long as the application set great I'll give one more example like the acquired podcast or somebody's podcast you know you see like accounts like podcast notes pop up who've made a whole kind of account based out of I'll go listen to that three hour podcast because you're probably not going to or you don't at least not the full three hours and I'll give you the highlight and that's kind of back to my original point it's like if you're creating content that somebody then is going to go and then boil down to the talking points isn't that signaling to you that you could just do the talking points it's interesting though because it's a growth channel for that podcast where they don't do anything they just put it out and someone else does the work of Hey listen to this episode that's good so it's an interesting trade-off sometimes I read the uh business insiders format is like headline and then like they'll do like three to four bullets of basically the the highlights of the story you're about to read sometimes I'm like so why should you know I think I'm good now yeah well then they throw the paywall on YouTube yeah exactly yeah yeah I think one of my one of my best Tweets ever is if I ever get canceled I just hope it's on Business Insider because no one will read it I love that if I do ever get canceled that's that's my hope that no one sees it so another question I have just in the newsletter in general how do you think about analytics versus intuition because sub stack has okay analytics they probably expand on what was there and then when you look at a new product like beehive you can get very very analytical almost to the point where it's maybe not helpful there's just tons you can do with it you could probably smash your head against the wall for days just diving in all your analytics how do you think about the artistic creativity side and also just the pure numbers it's a great question I think your your point there I would echo which is with anything I think for the most part if you get too into the numbers you're gonna drive yourself crazy I think ultimately your content is going to speak to the fact that you're too into the numbers it's kind of more robotic going back to my point from before of Leaning into personality I think that goes hand in hand with the artistic versus analytical side of just kind of like trusting your gut seeking feedback from readers doing things that aren't necessarily like analytics based based or even scalable quite frankly trying to respond to as many people as possible I think all good in the same bucket of just like art versus analytics now obviously some analytics are very important depends on what your newsletter is and what your kpis are obviously at axios for example you know we have open rate which is extremely important you also have click-through rate which is extremely important how many people click a link right open rate is how people open the email click-through rate is percentage that actually interact exactly now what's interesting though is with the click through rate right click-through rate obviously shows very like high engagement right because that shows somebody didn't just open it they're clicking something like they're clearly engaged however my newsletter at axios one could argue if I do a really good job people shouldn't have to click on anything right because a lot of times if they're clicking on something I say hey here's the full you know go deeper if you'd like if I do my job they do click I don't know you could argue that like if my click-through rate zero it's perfect newsletter right so yeah and but there were plenty of times I was like Hey guys go read this article or hey go look at this highlight so that's one metric that just an example I would use of like hard to really read that right I don't really know what I'm optimizing for there there's plenty of newsletters where the whole goal is to get people to the bottom and click off and go to whatever and so if that's what your goal is then looking at that not just click-through rate but you can see how many people click that specific link then obviously you want that as high as possible so email is relatively minimal in terms of the analytics you can get you're not going to get a heat map in the way you can with the website you can't see where people are spending their time you can really just see how many people opened it who opened it what'd they click on and so leaning into that as much as you can without driving yourself crazy is obviously a smart thing to do for instance I I found it much more valuable over the years in terms of kind of feedback in terms of shaping the newsletter to just straight up ask my subscribers via poll or via asking them to just reply to me directly like hey like what do you want to see more of what do you want to see less of and I know that's not the most effective way maybe on paper to get data and get feedback but I just found that to be extremely helpful and also signals to your subscribers hey you're part of this too you know if you're just on the back back end looking at your dashboard reading the analytics all the time you're not really involving your readers in that whereas if you're asking them every month hey like what was your favorite story this month what did you like what didn't you like or things like that then they feel like they're part of it over time have found that to be much more valuable let's say for example you never covered soccer but you're and So based on the analytics no one's ever clicked a soccer link you don't know that anyone wants soccer but someone's like hey put some soccer in there and then it starts doing really well it shows up in the data you would never know and again this would a good example of why running shorts so great is that what I was told like if people that don't like soccer and I cover every sport so to an extent everybody's got their Sports they like sports they don't like most of my subscribers I'd argue like all sports because that's what I'm doing but the stories are so short that if you're scrolling in the third stories about soccer and you couldn't care less you take your thumb and you scroll one scroll yeah that's what I tell people all the time like oh why are you covering this I'm like just scroll past it because your newsletter always sort of reminds me of newsletter version of SportsCenter I love that that was my that was my initial like how I like marketed it because I mean Sports Center back in the day I mean I was born in 1991 so grew up in you know 90s early 2000s was where wake up at 5am in Canada um we had TSN was the name of it like it was the sports network and ESPN was in the US yeah and it was actually awesome because it was mostly hockey so that was the interesting of moving to the US was all of a sudden they started showing all these other sports and I was like I don't care about baseball I don't care about like all these other things just show me an hour of hockey highlights which was the interesting difference with Canada it was probably 50 minutes of hockey they'd show like five minutes from each game and at the very end they'd be like oh yeah the Super Bowl happened and like I don't know like LeBron dunks are like well you know they wouldn't care about it I grew up watching SportsCenter you know they would they would just replay Sports Center all day I would watch SportsCenter like three times a day but also you know at that time we weren't getting you weren't finding out who won the game right when it ended right you didn't you actually turned tuned in a sports Center that night or that morning and like you didn't know what happened yet and that was a magical time that that and waking up and reading the sports page like I have so much Nostalgia for that because I would wake up and be like I don't know like who won you know read like obsess over the stats whereas now we do that right away obviously we see the viral we see Messi's goal five seconds after it happens we don't have to wait but I I will say like what still is valuable to people is putting everything in one place when people read my newsletter if they've already heard about half the stuff that's fine they already saw a domestic goal for example but if I can add that one piece of context something that that they hadn't heard related to that then that's still beneficial for them they're still going to find something they didn't know but it is interesting you say that because yeah when I first started uh Sports internet which is what actually has Acquired and kind of this this journey I've been on part of the reason was you know I had um been a sports nerd my whole life I worked at a bleach report ESPN right out of school where I was working at the hustle was the first time that I either wasn't a you know a kid or in college or working in sports media and it was actually so it was the first time I was like whoa like it's kind of hard to follow Sports if you don't have the time to do it or you're not literally working in sports media and I remember I texted a bunch of my friends I'm like hey like do you guys ever watch SportsCenter anymore and for the most part and this is when we're like 24 20 23 24. the most part I was like nah I don't have time for that and I was like well what if I basically took what's in SportsCenter and put it in a newsletter and send it to you in the morning you could read it on the way to work and all my friends were like oh I'd check that out so that's quite literally how it started that was literally the founding moment do you remember what triggered that idea in your mind it was literally me being like for the first time literally the first time in my life I was like I kind of feel not in the know about sports because I'm writing the hustle newsletter covering Tech startups and so I'm spending so much of my time in that world and I love sports and for the first time literally in my life I was like out of the loop uh and so as many people say over you know I kind of created uh solve a problem that I was experiencing myself it turns out a lot of people felt the same interesting okay so maybe we rewind just slightly you were working at the leecher report and ESPN did you learn about the media business there or any interesting insights those couple years certainly I mean so the police report I was writing and I was also it was like my first job out of school I was writing I was also just doing kind of like whatever they needed I was like helping with like Graphics how did you get that job completion report because that seems like a college kids who love sports just like a dream first job actually the job I took right out of college at police report was almost unpaid it was very low but they had what was interesting about it was they had it was a job that came with a program to like learn how to become a sports writer so I wasn't just writing I was being taught wasn't Bleacher Report their model was sort of this like distributed network of sort of college students certainly at the early stages so I came there 2013 when I graduated from Penn it was a very interesting time where police report had just been acquired by Turner and so Louis River was in this this place where they were still kind of this glorified blog with a lot of unpaid contributors but they were also now hiring you know Howard Beck Kevin ding like these these known Sports writers and so they're kind of in the middle of like blog and like legit Sports media publication which they've become more and more of and obviously they're very linked with like Turner and MBA and things like that they were kind of like balancing the two things at the same time but on the on the point of my first trip out of college like one thing I I talked to kids in college all the time who want to work in sports and I've found this to be true when I talk to other people other of my colleagues and people in sports that have been doing this for a while I think working in sports whether it's Sports Media or anything in sports is one of those things that for whatever reason you almost at the time feel like you were not taking you're you're not taking like career seriously because of course like everybody wants to work in sports right like I went through this thing when I was like am I just doing this because this is like cool or am I just doing this because like it sounds fun like it almost feels like it couldn't be a serious career because you know everybody wants to work in sports you know and I had to kind of go through this whole thing where I really like convince yourself no like you like this much more than the average person you and and there's serious careers to be had in here so it is kind of this weird thing I'm sure there's other examples but sports for whatever reason it just feels not serious enough you know I mean yeah that's true and I think the episode would be published right before this one it was with Dan Porter at overtime and we we talk about a lot of people don't even realize there's a business behind Sports and if you take it another step up the business of sports has basically held the Cable Bundle together while it collapses alongside the internet like it's so important it's so powerful here's another thing I'll say to that and I know I know Dan agrees because I'm sure we both talk to a lot of people like a lot of kids in college will come to me be like I want to work in sports and my answer all the time is like well that's not a job because people think that Sports is a career but I think Sports is actually just an umbrella under which there are many careers so like you want to work in sports well my answer is so do you want to be a writer do you want to sell tickets do you want to work like like sports is not skill and I think Sports is so interesting and people are so into sport that they just say I want to work in sports but that's not actually helpful right because what do you want to do you could you know you want to be a sales you want to do marketing do you want to do Puck you know Sports is not a career and I think people get that confused a lot because again it's like what they're passionate about and then they're like that's what I want to do but you got to think narrow down like no what skills you want to develop what do you want to do and then try and apply that within the World of Sports so then after Bleacher Report was it were you thinking like I want to stick in sports like is that how the ESPN thing how did that all how did that job switch happen yeah no definitely want to stay in sports and um so I ended up on ESPN which is like a dream of mine forever and went to ESPN and there was a little bit of a change in terms of not I was now um working in production basically working in TV I was in a rotational program there which is really cool we got to do a bunch of different jobs I did everything from deciding the top 10 plays of the day to cutting highlights for games as they happen to literally running the teleprompter with my hand you keep up with their pacing and as you work with certain anchors more you start to learn it but it's it's a pretty like the the and there's this live also oh it's live yeah so I think we had probably a week worth of like training where somebody was doing a nice set next to them and watched and you know you have the you have your headset on you got the producer in your ear you're kind of following the show and obviously there are certain segments where you don't need the teleprompter but many of them do it's when they're you know they're looking directly at the camera and are doing some sort of thing they've written but the the first day that I had to do that by myself is the most nervous I've ever been in my entire life really okay I mean I was just so nervous that I was going to click the wrong screen or you know I I just like if you messed that up and Scott Van Pelt is like on live TV and all of a sudden like it goes dark or you're past where he's trying to read I mean you're gonna your mistake is going to be very visible and then they're going to be so I was just so nervous thankfully um I didn't have any big screw-ups but that was a really cool job you know I this show I worked a lot of SportsCenter it was this show that I grew up obsessing over and all of a sudden I'm now kind of part of it and seeing how it's made and probably shouldn't shouldn't admit this but whatever um so the ESPN Studio there's like glass behind where the anchor desk is and you can kind of see where I as the production assistant a few other people are sitting in the back one of the first shows that I was working on I texted my friends I was like watch sports center tonight and I'm gonna raise my hand in the back and so like you see if you watch SportsCenter and then you can see me like like I saw you um but you know so so that was I think the the coolest part about the ESPN experience for me was getting to see how the sausage was made essentially well the other the other big thing that happened to ESPN for me was the first time I worked somewhere surrounded by fellow kind of sports obsessed people but I was told by numerous people there that I was more obsessed with sports than any of the you know so it was dude you're like really from someone who loves it and I think you know hearing that confirmed me that I was making the right career decision and it also gave me the confidence to I don't know just it just felt like it was giving me the green light to like go as far as I wanted in this world because I was I was clearly very passionate about it and not just on on par with the other people ESPN but like they were like dude like you you're like crazy a little bit I've had some of those moments too or someone that you maybe really respect or look up to they're like you should actually really pursue this more yeah you're good at it it definitely is it's a I want to say it's an ego boost I don't know if that's the right word but it's it's a confidence boost it just kind of confirms to you that you're in the right field I think and again going back to my point about people who want to pursue Sports I think it's one of those things you assume well everybody loves sports everybody's obsessed with sports right or at least you know of people who are sports fans we all love sports but if somebody's like well yeah but like you are like even more into it it's just something that was really important for me to hear early on that stopped any questioning in my mind that I was that I wanted to work at Sports and then you laughed Sports yeah why did you do that my friend was working at the skim at this time and I got this idea of what if he did a sports newsletter in my mind this is in 2013. that sparked an interest in me and like how do you start a media company was this when you were still a Bleacher Report I'm trying to remember timelines this was at ESPN early ESPN so like 20 into 2013. I was at bleach report pretty pretty short time okay 2013 2014. so I just it just planted this idea in my head of like I would love to like start a newsletter or like just like a media company but I had no idea how to do any of that I also grew up in New Jersey went to school in Philly I was living in Connecticut so starting a media starting a business was in my head and also like I gotta get out of this I want I want to live somewhere else my brother-in-law was also from San Francisco he's like you'd love San Francisco so everything was like startups West Coast it was like I should go to San Francisco and I should work at a startup and I should like learn media I obviously thought about sports media I would ideally would have loved to stay in sports media to do this but I ended up finding the hustle which was not Sports at all but it was very much startup like I said I think three four employees maybe and I really liked their voice and kind of what they were doing and so I took that job primarily to learn the media business still with the idea of like I want to start a sports Media Company sometime so you know I got out of sports media but I stayed in media and I think you could learn the media business regardless of the content so question what's the difference between sports media and let's say like Finance politics technology media like are there differences are they all pretty much the same the core model of any media company is relatively the same I think I'd say if you're comparing it to finance for example I think Sports is still much more in the entertainment side of things versus Finance where a lot of the readers are professionals a lot of the readers are looking for I don't know well I'm going to disagree I feel like a lot of the finance at least the mass Market finances I think somebody who covers Finance has a much better chance of getting people to pay for their content let's say they do like a newsletter and they charge 10 bucks a month if they're our value prop to that reader is you're going to pay me money but you're going to make more money because you're going to take what I tell you and yeah that's fair so I'm covering Sports unless I'm covering sports betting and my value profit is I'm going to give you picks and you're going to go like I'm not promising you some return on your investment essentially I think ultimately a lot of sports news at the end of the day is just headlines and entertainment there's nothing wrong with that but I just think that Sports traditionally and I think this is why actually the sports newsletter space part of the reason why I launched my newsletter was like nobody's doing this I think part of the reason why you haven't seen the same innovation in sports and newsletters happen in sports that you have in finance or politics is that people just assume that sports fans are not in their inbox whereas you know Finance or business news people are like oh they're going to read at work because it's helping them get better at their job whereas Sports still exists in this entertainment space for the most part and sports is probably one of the broadest forms of entertainment you know TV's kind of the bundles kind of eroding but if you just look at what are the most watched TV events or any entertainment events it's mostly the NFL and then there's like a little bit of NBA and maybe like one tennis in like the World Cup and that's basically like the top I'm sure I'm sure a lot of people have seen these these stats and I might be getting this slightly wrong but I think last year of the 100 most watched TV broadcast 87 were Sports and I also think what's interesting about sports is it's the most naturally verticalized media sphere if you will so Sports you have sports at large but then you have NFL or like football college football like you have all these leagues all these sports that have specific fans like some people just like the NFL some people just like college football some people only like soccer and so there's media spheres for all of these Sports if somebody was starting a sports media company and let's say you wanted to lean into newsletters it's already verticalized for you you launch a newsletter with everything and then you have an NFL newsletter MBA newsletter visually baseball so there's very natural sub verticals within Sports which is also how you make more money as a newsletter right you bundle and you can sell ads or subscription and have writers that cover different ones that are kind of like all sharing costs and generating Revenue over different and you maybe have a subscriber that instead of just subscribing to one they subscribe to the main but also Golf and football you want to get a whole two to three I think is this The Sweet Spot I don't remember the exact number at axios but there was some number it was like once people start subscribing to too many of our newsletters they actually become less engaged yeah well I think it makes sense right if you're getting like too much you kind of tune it out I think there's a sweet spot the other thing I'd say about sports media That's Unique is that so there's two types not two types of sports fans but two ways two major ways in which people follow Sports in my mind one is nationally so that's what are the stories of the day in the same way is true for politics or anything else you know the big news that everyone's talking about around the water cooler kind of thing and that's largely what I cover but there's this whole other side of sports which is fan specific team fandoms right so the way somebody follows sports news nationally is much more as like a reality they're following this reality show they're following you know they say again the same way you follow politics just like what's the news of the day whereas if you're like I'm a huge Die Hard Orioles fan the way I follow the Orioles completely different the way I follow Orioles is almost more like a cult yeah you know so there's two very distinct ways to get to sports fans one is nationally and you know what a lot of people places do they look at some place like the athletic which does plenty of national but their big value prop is you are obsessed with the Yankees and we're we're in the clubhouse we got reporters on the ground we got B reporters on the ground we're gonna give you a thousand words on your like seventh reliever because we know his whole life story and so you know your average sports fan I'd say is interested in nationally you know the headlines they talk with their friends aware of what's going on but then they have these teams that they're die-hard fans of that they follow in a completely different way that people would think would be is like crazy sometimes you know like I said you're like a cult member so would there be a third or maybe this is a part of the cult just like Regional sports like I'm in Detroit or I mean I'm in Ann Arbor which is close to Detroit so I like the Red Wings hockey I like the Lions football Pistons basketball is that kind of a third or is that just the cult probably would tie that into the ladder and maybe less of a cult but you're right like there's a regional sense I guess a better way to describe it would be there's two ways people follow Sports One is it as a news consumer and one is as a fan right okay so you know you're interested in what LeBron James is doing but that doesn't mean you're a Lakers fan whereas you are super interested in what happened to the Red Wings game last night because you're from there but if you lived in let's say Florida you could care less probably yeah and it's interesting too with the internet you start to realize wow the Lions suck I've been cheer for other football teams yeah it's been rough for the Lions but they're all they're on the come up for sure man my stock and Alliance really okay I because the way I kind of think about it I play a lot of fantasy football so I think about like what are the most undervalued teams I think I was thinking this going into the playoffs this might have changed because they sorted it while was the Jaguars I was like oh they're going to be really good next year I think like Trevor Lawrence could be a top five QB which is kind of insane to say but that's how you win in fantasy football you take him at the very end that's how you win at Fantasy Football and now increasing that's how you win betting I mean that's what's really interesting about the rise of betting and fantasy football which has been happened for a while is that people can now treat sports or transactionally and more it ties into this especially among Young's fans of like you know you're already doing all this research the analytics are much more approachable now in ways they didn't used to be and you have a lot of fans now like I know more that about you and I'm gonna actually like act on that or even buying baseball cards is back you know like yeah you think Trevor Lord for example like you said fantasy football if you think Trevor Lawrence is going to be a top five quarterback by his card right yeah I also am regretting saying that because he's probably gonna have a terrible year and if people had to go home but but I will warn you the NFL is there's so much parity in the NFL especially compared to some other leads where let's say the NBA NBA you can kind of see a good team building slowly NFL from one year to the next the Lions last year were a good example like the Lions were irrelevant and then last year out of kind of nowhere they're very good um that happens a lot in the NSL uh much more than than other sports yeah I haven't actually looked but I just I'm thinking anecdotally the Lions lost a lot of really close games what I'm remembering like I went to the game where they played the Seahawks and it was the game it was like 50 to 47 or something just every Drive was like a 60-yard run or touchdown or whatever it was fun to watch it's also infuriating because it was like it's just have getting scored on their offense was very good I think they had one of the most efficient offenses last year Dan Campbell's the man Izzy okay I don't you you obviously fall much closer than I do Dan Campbell is like you know people use the word football guy to describe people when they're just like every stereotype you can attach to football like they're super intense and they're like push-ups you know like that that is that's like damn well to a t he's like defense football guy of all time well I think what the lions always had was just discipline work ethic type problems where I don't know how that like if it's missing curfew if it's just like not trying in practice or something but an ultra problem you know I think a lot of teams even even though the Lions for example their roster now compared to five years ago or ten years ago obviously like completely different players everything's completely different they're still cultures that develop around franchises you look at the uh Miami Heats a good example in the NBA you know their roster right now they're not a single player other than Udonis Haslam who was also on the on the team when LeBron and the big three were there so it's not a case of the people there but the culture of the Miami Heat can stay consistent and that's because they have certain things they just drill into you they are known to practice harder than other teams like there's cultures that get built within franchises even though the players themselves come in and out interesting and I mean I know we have a lot of kind of founders of companies listen to this it's probably like it's a tone from the top kind of a thing okay so we really got sidetracked there so you have this idea or daily Sports newsletter move to San Francisco got the job at the hustle you kind of talk with this you pitch the idea of doing it how did that go how did you convince that because it wasn't the model it was kind of a crazy idea honestly yeah um I think so so what we did basically was launched it as a side project so we kept doing what we were doing and then we kind of launched this newsletter on the side and got you know thousand people to sign up I think we published it for like a month and the feedback we got over that month was so profoundly positive that really convinced everybody to Pivot to that as our business model like I said the hustle which now a lot more people know five people working there we were in this room in an apartment so so pivoting the business while certainly risky in some respects it wasn't like this huge undertaking it was like all right instead of writing blogs we're just gonna like put our stuff in this newsletter and set it and then we'll kind of monetize it and do all that stuff okay so then how do you write a daily newsletter because I write a newsletter slowly throughout the week which sounds like a lot of work it's a lot of work and obviously most daily newsletters are news news Centric right so you're kind of at the mercy of the news cycle and sports is impossible because my colleagues who read about the markets for example well the market closes they can have a normal life whereas I as much as I'd love for the newsletter to be done at 7 pm it's Sports hasn't even started yet yeah I say this writing a daily newsletter and anybody who's done so can attest to this is very much of a lifestyle you know people ask me all the time how many hours does it take you to write this I have no clue because I don't have a normal work routine it's very much like yes I have certain stories that are evergreen enough that I can write days in advance and get those done and kind of have them ready to go but so much what I'm doing is responding react reacting to the news that it's really if something happens at 10 pm I kind of have to be on now the nice part about that is that I'm not expected to break that story right away so if something happens at 10 pm I don't have to like get a story up immediately I can get it done for tomorrow morning but I guess I'd say about the rough daily workflow of a daily newsletter is having a really good system to follow the news so like I use I've built this and I've shared this many times on Twitter and things X yes is my RSS feed so RSS obviously very old technology but I've built this RSS feed that is invaluable to what I do it has every source that I would ever read it has Twitter has now pulled the API so I can't do that anymore but I had like all my favorite Twitter accounts I have subreddits newsletters like every source of information that I could possibly need I have in one feed and that allows me to constantly stay on top of what's going on it's honestly like if I miss a story it's on me it's not because I happen to not see it it's there I just have to scroll through it's almost like think about it as an email inbox if every sport story of the day comes into your email it makes it very easy for you to make sure you don't miss anything so I rely on that very heavily you know refreshing that throughout the day what's the product name uh reader r-e-e-d-e-r it's you know there's just some others that do fairly fairly similar things but this is synced across all my devices you know you can read all the Articles within there it actually allows you to link your pocket as well or any other like tool you use to save stuff so I can't tell you how like intuitive and easy this system that I've created for me is where I'm reading stories throughout the day and anything that's interesting I immediately pocket it and then when I go into right right later it's all saved right there it really I tell people like I can read the internet in a way that I control the spigot and I'm never overwhelmed so a lot of a lot of my routine is just kind of staying up to date and constantly seeing stories and pulling those off to the side and kind of saving them or immediately writing about them feeling out the news of the day and and deciding how to take all of that and organize eyes it and give it to my readers in a way that's very easy for them to digest interesting okay so what was the point then when you decided I've learned enough about newsletters I'm gonna do my own thing uh so it was a little over a year after the at the hustle and it was when I had that realization you know I still had that idea Sports in the back of my head want to do a sports newsletter that never left but when I actually found myself personally realizing I could use that product because I all of a sudden wasn't following news the way I could I was like I I gotta do this and the process of writing a new sports newsletter is going to get me back into sports which I miss everything was like pointing me in this direction it was almost incumbent upon me to do it yeah so how did you how did you start it like how do you start a newsletter we all see people starting them now if we are on Twitter or LinkedIn what was the process of starting one back in 2016 17 when you did it so the process was certainly not what it is now because the tools that just now just weren't there so I used MailChimp the one thing I did which I would still recommend anybody launching a newsletter do is I was very open to trying different formats Michael was okay so I want to cut I wanted to write a daily Sports newsletter and I have this idea of like SportsCenter in an email in my head but what does that mean what does that look like how many items is it and I didn't want to just assume that I knew best so I think in the first month and a half of reading Sports internet I probably sent 12 to 15 different formats really like I just kind of experimented there's many different ways to cover the news of the day format wise and so I kind of threw everything out there got feedback from people also just personal feedback of like how was that was that easier was that harder to do that was definitely a big part of launching it was quite literally just trying a bunch of stuff publicly and then adjusting it and tweaking it and finally kind of arriving at a format that I felt people liked and I also felt was repeatable enough for me that I could see myself doing that over and over and over and over with finding this balance of like a rubric to some extent but also enough Freedom still to I'm not not feel like I'm just like plugging in information into this rubric but I think that's a big part of Designing a daily newsletter for people is finding the balance of you know giving yourself this framework that you when you're reading the news are like oh that would be perfect for this section but also not pitching hauling yourself where if something happens you're like well I don't have a section you know you have to have enough freedom to not be a slave to your own format yeah because I'm trying to remember I I think what you really end up hitting on was like the one two three you had like 10 sections basically or was it maybe different numbers I was inspired by axios who later acquired the newsletter okay yeah and uh part of my thinking there again inspired by them and so I assume they had the same thinking was there's something really nice for a reader especially when they're on the phone and they can't see much above or below what they're reading if it's numbered they have a sense of like where they are in it so there's something there's something kind of like comforting about like oh I'm on five there's five left to go six you know you kind of it gives a sense of place and these are the kind of like detailed things that I obsessed over for so long ultimately with with axios we literally said at the top of every newsletter this newsletter is five minutes this is how many words it is is how long it's gonna take I think it's just a small thing but a big thing for a reader to kind of feel like they know what's coming so then how did you get people to start you know reading you kind of talked about it it's easier now than it was back then how do you get because I try to think of how I found it I think it was an ad in another newsletter did you ever do anything with Market snacks from Robin Hood I did yes I did I think that's probably where I found it hopefully that was early it was early so the main way to grow back then I mean outside of paid acquisition was simply doing cross promotions with other newsletters and as crazy as it sounds now this was what five years ago there weren't that many oh really okay worth that many so it was like oh Market snacks I got introduced to those guys you know they had a bigger following than me because I was just starting out so we worked out like I'll shout you out you know for a week you give me a shout out tomorrow did the same thing with morning Brew I'll give you guys a shout out for like a month that you give me one shot you know we kind of figuring out like how is this Fair a fair trade-off that was really effective and so a big learning that I had early on and this is kind of connected to that was like I did a few cross promotions with sports related Instagram Pages or the content of it was sports but it wasn't a newsletter and then I did cross promotions with morning brew and Mark's next which was the content was not sports but it was a newsletter and the latter was so much more effective and my conclusion was that newsletter reader was a demographic I tell people all the time it's somebody who reads the news somebody who reads newsletters already if you think about it it's like they already get the newspaper right they already have they already the newspaper already comes to their driveway every morning by saying hey would you like to read my newsletter or essentially all you're asking them to do is would you like to add another section to that newspaper you already get in the morning would you like to add a sports page you already get the newspapers you like to have a sports page oh that's sure I'll try that out whereas if you find a sports fan on an Instagram page and you say hey I have a sports newsletter even if they love sports you're still asking them to subscribe to the newspaper which is a much bigger leap they're like well I don't get the newspaper and I don't know if I I have the time to re so that was a really big learning early on regardless of what the content is if somebody reads a newsletter there's a decent chance that they'll try yours out yeah I think there's demographics too like even Instagram versus Twitter Twitter is very Tech space so you know those people probably are more reading versus the Instagram audience they might not even have Twitter or the email app on their phone it's very true and I think maybe becoming less true because newsletters are much more ubiquitous but especially back then if somebody doesn't read newsletters already like trying to convince them to sign up for them they're like I don't even use my email man or whatever you know whatever it's like it's just you have a foreign idea like well you're gonna you're gonna read an email from you like yeah it's an interesting thing we're coming up to now with I've heard some murmurs or seen stats about gen Z and email like they don't check them like you gotta hit them on Snapchat or something or like Tick Tock it's so interesting to me with email is that I think we can all agree that it's a very effective medium for newsletters been a parent for a while and continues to become more and more apparent every time somebody says email is dead it's like well it's actually better than however I think we can also all agree that there are limitations to it and young people is a perfect example I you know most high schoolers do not use their email let alone have one um even in college you get an email which is which is great but do you really check it I mean I didn't use my email much in college so there is a certain downside to getting young people to read newsletters is tough however the thing that I always tell people is like I believe in email as a medium and newsletter as a medium but if Apple made it possible to send Rich text messages so like if I could essentially send my newsletter to you via text and let's say you get a message from me and you hold your thumb down and it opens the whole newsletter basically if there was a way for me to get give you the same experience you get from me via email but in a text message I would do that email is the perfect way to do this right now and that's why email is never going to die but if you could keep the same benefits of email in a place that you know more people use younger people use like it's very interesting like this push and pull of email if something comes to replace it I'll jump there immediately you know what I mean yeah yeah I would I don't know I would bet you I don't know what the time is but I know if I want to say five or ten years but I do think that's gonna happen if you kind of look at what Apple's been doing they've been starting to build out this advertising Network when you think about they've made it harder for Facebook to track ads like they're planting all the seeds and again we're going to get in this a little bit later with their content business you monetize content with advertising I think iMessage is one of those sleeping kind of content products or like iMessage could have been what Snapchat is or there's a lot that they can do with it it'll be interesting to see I would bet within the next five or ten years you'll be able to do something I've seen a couple newsletters experiment with text I experimented with text as well I think there's a certain balance of email especially on a daily email if I get a daily text I think I would like within a month be like all right subject you know it's definitely like a balance the strike there where email is like you can still get to people where they can kind of tune it out a little bit more but the bottom line is and I this is what this is how I think about newsletters is newsletters just like texts just like DMS on Instagram Twitter you know whatever it's all messaging and that's really what's effective what's effective is messaging what's effective is you're coming to them they don't have to find you they don't have to seek you out you're coming to them at a consistent time and you're coming to them in an app that they check all the time so if I send you my newsletter it pops up on the top of your phone the same way if I texted you the only difference is when you click it you're opening a different app and it's probably too that you get a rich you know HTML format in email versus text is just you know text exactly but then also a cross-platform where you could be on your phone or on your computer versus Instagram no one checks out on their computer you know you see um even substack did this which uh I thought was a mistake but there's also benefits to it so I get it but like for the last six years there have been so many attempts by people to say oh like people are really into newsletters but it's not the ideal experience to read those newsletters in the same inbox that you have all this other email and stuff and promotions maybe we just create a separate app just for newsletters and I and I get it I totally understand but like what you're missing there is the biggest benefit of newsletters is that it is it is in your inbox because that's one of four apps that everybody checks all the time the the chances of you getting me to start habitually opening a new app I mean I can't tell you the last time I adopted a new app maybe threads was right which I'm slowly you know how hard it is to get somebody to add a new app to their routine everybody checks email if you look at everybody's screen time like emails probably at the top of every working professionals list of apps they open most are you actually using threads too by the way not really I'm starting to a little bit interesting okay my assumption was I mean I use it the content sucks it's just Instagram but text but Facebook will get us to use it slowly what's funny for me is and I think this is probably true for a lot of journalists or people who write and and have an audience for a living for so long like Twitter for me was like that's where I am that person and then Instagram is like my Instagram followers are like my friends from high school which is a completely different audience and so the only way for Threads to make sense for me is if I get enough of that audience that I have over here to move over that's easier said than done so what was the business model then when you started Sports internet and kind of as you scale it up was it sponsors because I don't even remember sponsors it was just me and uh selling sponsors was hard and um I had so much I was just like stretched so thin that ideally I would have had different daily sponsors or at least weekly but I ended up signing like longer term deals for less money but just to like make it easier for me just do like a month of advertising so I first actually have the check right here uh amazing can we see it I kept it yeah well it's in the uh it's under the table so it'd be hard to see oh but okay it was uh my first deal was with uh FanDuel oh interesting that's a good one it was a result of a bunch of people from FanDuel reading it um and then I kind of solicited ads and they got back to me and made a lot of sense so that's awesome with my first Advertiser and it was like a month-long deal and I think it was wasn't much again I was just very early I probably had like 5 000 subscribers I think probably if I had to guess I mean actually let's see what exactly it was yeah okay it was two thousand dollars actually so that this I think was for two weeks yeah two thousand dollars for two weeks okay so ten emails for 2000 bucks so they 200 bucks an email on 5000 subs and for me at that point FanDuel was a big enough name that for me almost that that advertising deal was more like legitimizing what I was doing I think there was something to be said for having sponsored by FanDuel very early on solo person doing a newsletter that kind of gave it a sense of like legitimacy and I think that you know that's true for a lot of early advertisers like there's benefits Beyond just the revenue obviously the revenue is most important but there's certain companies that are known enough that immediately make their ears perk up like oh this person's legit you know I mean they're social proof I mean people you see that all over the place like hey you should read my newsletter because LeBron James subscribed to my newsletter fanduel's a sponsor we've broken this story about a trade all those things people like holy like we got this is a this is real this is a legit newsletter so then how did you kind of evolve that over time like were you ever in a spot where you're like I'm okay over is it the whole time you're just like I need to figure out how to make money I got to get this new issue out were you getting any sleep what did your days look like then when you were writing this thing not getting much sleep he was you know continue to be ad backed I developed a secondary ad where I created this game called The Gauntlet where it was essentially like a pickup so I'd have a question at the bottom of the newsletter starting on Monday like will Bryce Harper hit a home run tonight yes or no and I would see who clicked yes and who clicked no and then depending on what happened if you got it right you'd move on you've got it wrong you'd be eliminated how did you do that I think I remember that the reason why I didn't keep doing it was because it literally made my life so hard because I had to go see who clicked yes go see who click no and then I would create the newsletter the next day but I create two versions one to send to the cohort that said yes and one is going to go over it says no and I had to keep doing this every day until I got to Friday it was the cool it was awesome I I thought it was so cool but I was like I can't keep doing this but I but I did have that sponsored and the sponsorship was like depending on how you did the higher the like discount you got it was with a company called wallaco it makes like athletic clothing it's like if you got all the way to the end of The Gauntlet you got 25 off if you got like one right you got 10 off so I tried to gamify like the ads it was I thought it was an awesome thing I would love to bring it back if I could figure out how to automate it or just have somebody like doing it that's not me but that was kind of how I was monetizing it I didn't think I was going to make it profitable just by myself my goal when I set out and launched it was definitely to hit a certain Milestone which my mind was 25 000 subscribers and then I was gonna go raise money and hire people and build out a whole business so like that was that was my goal hit 25 000 subscribers and obviously before that could happen ended up selling it to axios which we can what is that like getting acquired well it was interesting because it's like getting acquired as one person with one newsletter so like very different than acquiring a business with a lot more assets or a lot more employees it was really more of an aqua hire the one thing that I think really worked in my favor I made a very intentional decision early on because I figured this could maybe happen was I never spent a single Dollar on paid acquisition and and so what I think that allowed me to do is tell more of a story when I was getting acquired like as opposed like if I had spent money acquiring emails and I had a maybe bigger list as a result of that but my open rate was probably was going to be then lower because I was getting subscribers and in less organic way I think the negotiation with axios would have been more of a math equation it would have been more like hey you have 17 000 subscribers each subscriber we value at this amount of money and therefore this is how much we're going to buy for whereas I was able to say to them let's forget the number of subscribers my open rate is 63 which it was and so the story I was able to tell which I think a lot of business and a lot of when it comes to Acquisitions is what's the narrative what story are you telling my story was you're not buying 17 000 subscribe emails you're buying a community of people who are obsessed with this product who would I don't send it out for a week which happened one time because I was on vacation and I didn't communicate well enough people freaked out okay and two-thirds of them open every single Edition dad allowed me I think to tell a completely different story and I think it helped in the negotiation get a higher multiple for it quite frankly did they acquire the email list yep so they acquired the email list so it was an aqua hire so they basically acquired my email list you know that was a separate transaction and then they hired me to come over and continue doing it the reason why I ended up going there well many reasons one being I just thought it was a great fit like I said they had inspired my format they really were newsletter first in a way that few media companies were and still are I felt they really understood newsletters they spoke newsletter if you will and also I was so broke and so burned out and I think one realization I had and this happened like less than the year after I started it but one relation realization I had had over that time was entrepreneurial as I am and as much as I want to like build a business and run a business I was having so much more fun writing the content and what axios or any company at that time was basically offering me was let's let you do that and we'll do all this other stuff yeah because they probably helped you sell ads right I'm assuming you didn't have to think about that anymore exactly like just the fact that I'd never had to think about like like think about that again at least in that role and I just felt like I was I was doing so much and then like trying to pour myself into this content but just the idea that like what what could I do if that was my sole Focus I feel like this is really working I feel like people are really liking this but I also feel like I'm just scratching the surface on what I'm putting into it because I just only have so much time it just felt like the right move okay so two questions what is a good open rate and click-through rate just for other people interested in newsletters and then how do you sell sponsorships for a newsletter so good open rate I guess is Up For Debate I mean the industry average I believe is like 17 so is this like news newsletters or is this just like even that's why it's kind of misleading because I think so many like kind of Thai email marketing and news literature into the same bucket email marketing is like a lot of there's a Spam and crap whereas a lot of newsletters are like editorial media products totally different thing all under the same umbrella that's probably a misleading number I mean I would say the average of newsletters is probably like 30 maybe that might even be high there's a lot of bad newsletters out there just like there's a lot of bad podcasts and everything okay um I think so I would say if you're over 40 you're doing a good job that's it's good news for me I'm I'm higher than that yeah not that much time I'm not 63 but I think I I think yeah 63 was unheard of yeah that's actually insane based on I think the highest I've ever seen is 77 but it was like a 3 000 person list or something yeah super Niche and curated mine was the exact numbers 63.2 percent open rate and I had almost 18 000 subscribers to be clear to maintain that like I could have had a lot more subscribers but I like cleaned the list quite frequently so like oh did you every three weeks yeah every few weeks I'd see if this person hadn't open sometimes I'd email them be like hey you want this and you know maybe it was going to their spam or something I didn't realize it you know it was very manual and kind of took a lot of time and maybe wasn't worth it but I think ultimately it was to like really focus on the open rate because going back to what I said like telling that story if I had 25 000 subscribers and a 55 50 open rate versus 1863 I think that tells a very different thing and it's ultimately what is 8 000 emails gonna be that much more valuable that you're not able to tell that story or not so I'd say anything over 40 I think is very good and and so for somebody who's not familiar with newsletters or like how the business Works open rate is important because why uh you're essentially telling advertisers this is how many people you can expect to see this and it also just is a great you know measure of just general like engagement if you have a million subscribers 20 open rate it's like all right you have a lot a lot of people like are signing up for this thing but not that many people really can only 200 000 are actually opening it right whereas if you have 400 000 subscribers and fifty percent operate it's the same number of people seeing it and it's like oh way more engagement so yeah to your question of like how do you sell ads what info to advertise one I mean I think there's two you know there's more than this but generally speaking there's two types of ads being sold in newsletters these days one would be a brand awareness campaign so that's simply hey we want to be attached to your content we think you're doing a great job you know your audience would like what we're doing and really what they're paying for is just a spot in the newsletter often they'll have some sort of Click through like they want people to go to their site or to buy something but the deal itself is not structured around clicks at all it's just we're paying you this money for this done deal and then you obviously have to report back to them and this is somebody you've opened it whatever but then there's also deals that are structured around clicks like Performance Based or something performance ads exactly we call them performance ads where that's usually you know DTC companies or companies with products and they want to sell a specific thing and you're getting paid out usually it's a lot of times you'll structure it with like a flat fee up front but then you know that fees relatively lower and then you're getting paid based on either just a straight number of clicks or a number of people who actually purchase just like any any sort of kind of affiliate deal it's pretty straightforward you know if you send 100 people to buy shoes and 80 of them buy the shoe like they're going to give you a cut of each of those sales essentially when you start to kind of think through some of these numbers a fairly large newsletter list can be a pretty lucrative business where you write one email 300 000 people open and read it you drove let's say 500 people to buy a product and you're getting paid you know 10 bucks per purchase that you drove per click you wrote one email and you could make ten thousand dollars that's a pretty the math on that like it's it's they're good businesses they can be they're really good businesses you can keep it really lean and I think that's why you're seeing a lot of people start newsletters as one person or two person or three-person companies is because you run the numbers if you do a good job it's a profitable business pretty quickly and even if you compare it to podcasts which I would put in a similar bucket of just lean business cash flow positive businesses to start a newsletter is way cheaper than a podcast you don't have to buy any equipment I mean a good podcast microphone is a pretty good chunk of change there's a lot of things you can do to improve sound you know most people nowadays are going to film the podcast there's a lot more to it whereas to start a newsletter you need you know a beehive or a sub stack or some way to send those newsletters you need a computer yeah you could type from your phone and sub stack is free when you start you don't have to pay so I mean when I was doing sports internet which is what I sold to axios like I think my monthly costs uh strictly related to the business which you know ended up entailing some other things because I did have a website and I did have some other things but it was like probably like 200 bucks which as we talked about you made that from sending one email was about 200 bucks yeah so they can have pretty good margins I think they get a little bit of a bad rep sometimes when people especially Venture investors will say media companies are bad Venture Investments it's because it's your point you can't just blow it up super quick with the typical Venture Playbook but when you're like Bloomberg is one of the it's a private company but it's a massive business it's basically a media company that's vertically integrated selling people twenty thousand Eight dollar a year subscriptions for like a special keyboard like some data I mean like you look at some of the most successful newsletter companies did not have to raise much money because you just quite frankly don't need it I think when the investment comes in venture or otherwise is usually when the newsletter has had some level of success created some level of community and there's obvious Pathways to find more revenue streams for that Community whether it's events or whatever else the investment is based on the community you've built through the newsletter and now like what else can we do and so one of the companies I invested in personally was is essentially like a newsletter holding company called work week I don't know if you've seen them but they've started launching some software products so all their newsletters are B2B and I think the first one that they've kind of announced publicly it's a franchise newsletter I'm not going to get the number but it's tens of thousands of basically franchise owners people who own Burger Kings and McDonald's and there's thousands of these different restaurants and Retail and Landscaping businesses that you can you know essentially borrow the brand name and open your own local version of it it and so now what they're doing is they're launching software related to people who run franchises so obviously they're monetizing with advertising and usually what they'll what they'll do if you subscribe and read the newsletter the ads in the newsletter are hey open like a Krispy Kreme franchise or open like a dog grooming franchise so very relevant and targeted ads but then they're also like hey pay 100 bucks a year a month whenever the price is for the software to help you run your franchise better I don't know what direction they'll go but when you think about when you think about some of that math I was like okay they might acquire a newsletter reader for two three four dollars they'll profitably serve them the advertising business but then suddenly there's a software business that maybe makes thousands of dollars a year per customer and they acquire them for two dollars in the newsletter and I think that you're exactly right and I think the that model really the tip of the iceberg of that because it is true that especially right now the ad Mark it's pretty soft and any Media company that's strictly ad backed it has no other sources of revenue is not a good idea but I think think with work week and what they're doing specifically to what you talked about speaks to what I said before which is you can just build a really strong connection with people with a newsletter more so than even like a blog like you think about um if their franchise guy was just writing all of the same content he's writing in that newsletter but on a Blog plenty of people will still seek that blog out and end up reading the stuff but like there's something about the fact that they're getting that consistently and they're just like there's a relationship that's developed there that's just kind of hard to explain but then when you when it comes to time you want to sell them more things like it's just that you're able to create a community so much quicker and in such a more profound way through this newsletter and it kind of seems simple but it's true and the newsletter is also a blog like you can go read the newsletter online too so what it's funny you say that like one thing um I tell people all the time like you remember you know like before people started doing newsletters this this as much they are now you'd have a WordPress you'd do a Blog and then on WordPress there was always the option to like send this blog as a newsletter as an email as well and I feel like we just basically flipped that and it makes so much sense because in this era where everybody's overwhelmed with stuff and you're typically opening your phone going to social media Network and just you start scrolling aimlessly and there's no intention behind what you're doing why would you put your content somewhere where people have to seek it out and then maybe they get it via email why not just send it via email and then they can also seek it out in hindsight it's like so obvious that people would choose to write a newsletter that's also a Blog now then have a Blog that is also a newsletter yeah when I kind of think about what are what are the apps or the properties the digital properties that people go and seek out it's usually some kind of aggregation product whether it's Twitter Reddit Facebook Instagram even like Netflix is again aggregation maybe games if you love Candy Crush maybe that's an example but yeah it's very rare I just think about myself and I think this is true of a lot of people like I rarely go to websites I really like intentionally decide to go find something I mean the only time I'm doing that is like a Google Search right we've almost trained ourselves in this social media era to like open our feed and then we kind of know we'll find something eventually and maybe you end up going down a rabbit hole but there's very little intention anymore and so I think the way to kind of break through that is to come to them as opposed to rely on them to find you yeah but then you probably also want to make sure that you're not solely reliant on just email as a Channel or just Instagram just Facebook media companies have run into that problem so you almost want like a multi-pronged and again it's like multi not just multi-business model where you've got sponsorships events subscription recruiting software but also like hey we've got email SMS text we have a bunch of people on Instagram to pull them in a bunch on Tick Tock Twitter so if like one thing goes down you still have multiple Hooks and things to bring people in the only thing I'll say to that which is kind of counter that point but not really but like it's just if I say anybody starting a newsletter is I do feel like it's kind of the default mode to just let's say you launch a newsletter like of course we need to we need a Twitter page and a Facebook and Instagram we need all these things and I found that especially when you're early on and you probably don't have the huge audience I think you're actually better off not like let's say you you have a Twitter and you have five followers I think it's actually better for you to not have a Twitter why why publicly make it clear that no one really yeah and also I think you need more of a strategy first I think a lot of people just launch all these social platforms and don't really have a plan yeah I think it and you it ends up doing you a disservice I think you know if you launch a newsletter maybe maybe you also have an Instagram page but be very intentional about like well what is that you maybe there's one section every day that you also have Instagram and sometimes I think people just their default mode is just like we need to have all these things but there's no plan it's just like we have them and we'll figure it out maybe this is a good way to segue you recently left axios now you're going to Yahoo Yahoo is a really interesting business because I forget the stat I think it's like the third most visited web property or something I think it's like six or something but whatever it is it's a lot of people billions a billion users a month what was your thought process on going from axios to kind of this sexy newsletter First Media company I think they just got acquired right maxus did tonight you're going to date Yahoo Fallen Angel you know maybe you're in the middle of a turnaround I'm not sure but I'll let you dive into it but what was the thought process because that seems like a crazy move on the surface so the thought process was a few things one is I agree with you I think Yahoo is in a really interesting spot and I think ultimately it's a rocket ship I'm really a big believer in the leadership there now so that's obviously a big part of it they just hired a Ryan spoon as the president of Yahoo sports he's really well respected around the sports media industry worked at ESPN so a big fan of his a big fan of the CEO of Yahoo Jim lanzon um so that's you know first and foremost I think anytime you're looking to go to a new company if you really believe in the leaders and the people who are going to be calling the shots what's more important than that I also think that you know you think about about okay I'm in the business of newsletters and email Yahoo literally has email there's clear energies there it's the second biggest still behind Gmail I mean there's some stats by Yahoo that people don't realize but the second most visited property on the internet behind ESPN like we said six website um second biggest email uh service behind Gmail Yahoo finance I think is number one in finance like that it's a huge audience so a lot of thinking what is that some of the thing and the other thinking was audience right my goal with this newsletter is to build the biggest Sports newsletter if not just newsletter period in the world and we're not there yet axios I think uh we're in the hundreds of thousands of readers I want to I want to get the millions and a place that already has millions of readers feels like a great place to do that the other thing for me just personally was as much as I enjoyed being the sports team at axios me and my uh colleague Jeff Tracy who wrote this newsletter like we were the sports department at axios and that was really cool in some respects like we were you know was not competing for Stories We Were where the sports desk but what excites me about Yahoo is like now I'm going to be surrounded by tens and almost 100 Other Sports reporters and kind of able to work with them able to share a lot of their content in my newsletter and so I just think as somebody who's obsessed with sports and just love sports the way I do to be surrounded by colleagues who share that same passion as me is I think hopefully going to ignite a lot more passion in me um as I continue doing this and so I think it just makes a lot of sense for me as I continue this journey kind of you know I think in some respects was kind of hitting the ceiling at axios in terms of okay covering Sports at a place where Sports is not the focus and axios I think we have one of the biggest Sports newsletters out there but no matter how big that newsletter got access was never going to be thought of or known for sports for me it's like I want to go to a place where the sky is the absolute limit and I think yeah presents that opportunity yeah so I kind of think about too where does Yahoo rank in terms of fantasy platforms are they pretty high on that too yep okay it's an interesting time for you to be joining because fantasy season is going to ramp up how do you think about them like launching like does Yahoo have a sports newsletter yeah Yahoo has a sports newsletter we're gonna see how how we uh leverage that and moving forward but I mean the bottom line is uh Yahoo is a really big believer what I've been doing which is another reason why I feel confident going there like you know if I was going to a place where I really had to sell what I've been doing and point out you know why we should keep doing this like I'm going to a place where like no we love what you're doing let's do it and let's make it even bigger and better so that's really really excites me and you know you mentioned fantasy I think betting kind of works into that too it's all kind of this part of the same like fandom but interacting and not just make predictions but actually act on those predictions and I think Yahoo fantasy and betting are all intertwined there yeah who has Yahoo sports book and fantasy so I think incorporating that all into my sports coverage which is kind of this daily touch point for sports fans you know for so long I've basically been telling you the news and now I think I'm gonna have a really cool opportunity to also intertwine betting intertwin fantasy and all these other things and ways I haven't and just make that kind of daily experience for a sports fan much more engaging interesting so are you starting a new newsletter product at Yahoo or you like what's gonna happen yeah new news is a product but I would kind of frame it as a continuation of this journey I've been on so I started a newsletter in my room in San Francisco just on my own and then went to axios and built that up into a very large audience kind of figured out you know what works what doesn't and now this I I'm kind of thinking about this as the next step in that and going after a much larger audience and axio sports is essentially what can two people put together and not to say that you need that many more people to do it well but like I'm excited to see what can two people but with the support of an entire Newsroom put together and uh there were so many times over the last five years when I was just like if we had one more person two more people think about what we could do because I just simply couldn't do it all you know I there were so many stories that like oh I would love to spend the next five hours reporting this out but guess what I have to like write five other things and when that story falls through the cracks whereas now we have a lot more resources a lot more support that I can do that story and that will play itself out over and over and over and I think the end result will just be a better product interesting so and I think you did have a really good product what do you think you're able or why do you think you were able to cut through the noise and get Commissioners and sports VIPs to pay attention to you and this is a there's actually a question from I would label them as like a VIP in the Sports World they wanted to remain anonymous but what do you think you did right so I'd say there's a few things but I'd say one that I definitely point to is from day one my hypothesis was I think you can combine sports news with sports business news which is news about the industry of sports and for so long and still to this day those are very separate right it's like sports news is for the billions of fans around the world and sports business news is mostly for people who work in sports a lot of that is like you know stuff about TV ratings and stuff we've talked about a little bit like sports holding the Cable packages together like the business of sports and I always thought if you make that Sports business stuff interesting enough for your average sports fan they're actually it's actually really intriguing for them so I just from day one I've combined them like I have some people who would consider my newsletter or Sports business newsletter I don't think that is the case they have other other people who consider my support my newsletter or Sports newsletter so I've been able to combine the two and I think the result is that your typical sports fan who reads my newsletter and I also have Adam Silver a commissioner MBA reads it and I think for Adam he gets sports news as he's a sports fan but he also gets news about the industry that he's in and it's all in the same place and it's all kind of you know when you combine them in the same place I think you end up seeing you're able to connect more dots and you're saying if you're hearing you're getting news about what that's relevant to sports fans and news that's relevant to sports Executives you kind of see the synergies between the two and I don't think there's any reason why those have to be separate yeah and to your point about you know Adam Silver over reading obviously he's probably maybe he's getting some NBA news but he's probably following like oh interesting stuff in golf or into another sport that I probably should follow but I'm not as in the weeds the benefit of having a newsletter where my value proposition to readers is like everything that is important in sports is going to be in here if you're the commissioner of the NBA and you feel like why are we in here today or like why I feel like we haven't seen as much coverage about us lately like if he trusts my judgment and I'm deeming there not to be that many important MBA stories this week for instance maybe that's important to note and maybe there's some reflection that can happen there so I think anybody who works in the business of sports if they're seeing things mention a lot in my newsletter or they're seeing things not mentioned it's a good reflection of what's really kind of hitting out there right now what do you think is the most underrated or under reported story going on in sports right now so so to be clear this is definitely being reported so many people might not agree this is underreported I just think it's underreported because much as it has been reported I don't think you can report on it enough and that is just the momentum that is happening right now in the U.S around the sport of soccer and I think you're seeing that in many uh respects obviously the women are the World Cup right now Messi coming over the MLS is huge and it's all there's a very intentional push around soccer right now in the lead up to the 2026 World Cup this the 2026 World Cup is going to be we're going to break every viewership record I'm calling that right now you're just seeing that event where three years out is mobilizing people at every level of soccer from Youth Soccer to high school soccer to college soccer and then you have things like messy coming to MLS there's just so much momentum um I think you know for so long we've called the Big Four Sports NFL NBA NHL MLB of soccer has always kind of been the fifth one there now I think if you not considering leagues but Sports you know basketball football hockey soccer soccer is actually above hockey um and has been for a while in terms of like particip rate in terms of participation interest I mean I did you know many more Americans play youth soccer than hockey MLS has long been seen behind NHL which is true because the best hockey players in the world play in the NHL best hockey players in the world do not play at MLS and uh that's a result of soccer being you know the most popular sport in the world and you know it's just a different situation but I think Messi is such a big figure is such a game-changing signing for MLS that you're now like I think the question of what are the big four leagues should it be big five like that that's a huge question in sports and I think MLS moving forward like has a legitimate is it legitimately in the conversation in a way they haven't been so I just think overall just pay attention to soccer and there's a very intentional effort at all levels of the sport right now to make 2026 as big of a success as it could possibly be it's going to be the biggest world cup ever you cannot report enough on soccer over the next few years it's interesting that we went from I don't know we did the last World Cup in literally like the desert a hundred 150 degree heat it made no sense now we're doing it like the US it's just a probably a better environment to actually host the tournament period there's probably going to be a lot of money that's made I'm talking about the business side of support there's gonna be a lot of money that people dish out and spend the field is going to be 48 teams that's so many teams is that more than normal oh yeah these are 32. oh wow so this is yeah it's like significantly bigger I can't wait and put me on record every viewership record will be broken and this isn't in an era where viewership for things even Sports is going way down the importance of live sporting events of that magnitude are just becoming more and more important I mean there's only so many events every year like the Super Bowl that everybody stops everything to watch the World Cup like you look at the Women's World Cup right now in New Zealand and Australia like the the women played at 3am last night like that's tough whereas when it's in the US and the games are in prime time I mean it's gonna be huge yeah and then I think too the the argument I saw when Messi came over people were like oh he's he's retiring he's securing the bag it's like he just won the World Cup like he was like the MVP Messi is still the best player on the field yeah I think that was evident by him in and this is why sports are the best because they're just unscripted and it's like things happen that are just absolutely incredible and I would put Essie's first MLS game so hyped could not be any more hyped literally and he comes on and in his first game in traditional fashion he's always been known for his free kicks he comes on and scores the game winner I mean you can't you cannot script that I mean if somebody would have scripted that people would be like no that's too unrealistic who is the most underrated athlete in sports right now any level any sport any country who's most underrated I would say within hockey circles this is not true because within hockey circles people are aware of this but I think within Sports World more broadly they're not and so that's this is kind of a weird answer but I think this is my answer and it would be Connor McDavid is the most underrated player and the reason why the reason why is I think we're seeing maybe the greatest hockey player of all time this is a hot take because he's still very young and Wayne Gretzky is somebody who lived uh but I literally think like that's what we might be watching and I don't think even some casual sports fans know who he is yeah so for people who don't know can you give us the quick I I do know as a Canadian I know who he is but I remember Dave it is the best player in the NHL right now plays for the Edmonton Oilers who Gretzky also played for Wayne Gretzky is probably objectively the best hockey player at least by most objective measure it was the best like this past season Conor McDavid was doing things and my newsletter is always full of like stats and I can't tell you how many stats last year was like Conor McDavid first player to do XYZ since Wayne Gretzky he's in a universe of his own and Wayne Gretzky is often the only player that's ever done the things that he's doing so he's the best player absolutely no argument um in the NHL right now but I think you know for American sports fans the fact that he plays in Edmonton the fact that hockey is a very Regional Sport and like it's not National in the same way the NBA is the NBA regardless of who you root for or where you are like you're gonna hear about what LeBron James did last night okay just that's how the media Cycle Works that's how NBA fandom works but I just think there's a lot of people out there who just don't fully understand that maybe the best hockey player to ever live is currently playing why is he so good like is he fast can he hit can he score pass is it just everything he's all around just he's just really good at I mean I think if you could point to one thing that's just visibly like jumps off the screen the most is his speed and that's you know in hockey like it's different from like soccer or basketball or it's like Sprint speed and like skating speed is just like a skill and when somebody is just faster than everybody else on skates it's crazy to watch and I think there's just highlight after highlight of Conor McDavid getting the puck he's got three defenders in front of him and then like two seconds later he just just like weaved through the the puck is not an inch away from his stick and it's just mind-blowing to watch so I'd say his speed is the one thing that stands out the most but he's really all around just fantastic at everything who do you think is the most underrated athlete of all time oof that's a great question I might go with another like weird answer of like somebody who def people definitely know is great no that's totally okay Tim Duncan Tim Duncan interesting yeah I think Tim Duncan is one of those guys that when people make lists of like top 20 players of all time is rarely on that list because people don't like close their eyes and picture sure Tim Duncan highlight reels in the way they picture like Kobe Bryant highlight reels uh Will Chamberlain because Tim Duncan's kind of boring athletes that just like win and like get it done and they're not like sexy oftentimes get underrated when they're playing but most important mostly and even more so after they're done playing because they kind of get lost and the only time they really show up is in like record books and not and I think a lot of times when we think about all-time grades the highlight reels that are like playing in our heads that we can like remember it's not the stats and I just think Tim Duncan is like the stats would support him being in the top 20 of all time if not higher and I just don't think he appears on enough of those lists and I think that makes him extremely underrated he just is one of the best winners in NBA history and I would put him up there for sure and so Tim Duncan was I think either Center power forward he was like the tall guy he played for a team the San Antonio Spurs did they win a couple championships oh yeah yep you won multiple championships with multiple different um supporting casts around him at one point he played with David Rob Robinson who was a fellow seven footer so his early career they had like the Twin Towers going um and then the more modern Tim Duncan was in the 2000s people might remember the Rivalry between the Spurs and the Heat they kept meeting in the NBA finals and it was you know Tim Duncan Manu Ginobili he was from Argentina Tony Parker who's from France and then Kawhi Leonard early career before he went to the Raptors and subsequently the Clippers that Spurs team was just 10 Deep and just ball movement it was just the ultimate team I kind of remember but that's a good point of them being just him being underrated last question do you have a like a CEO or a Founder that you really look up to or really respect certainly a long list there I don't know him and I don't know enough about him like in terms of his leadership style and things like that to really speak to that part of it but for me as somebody who is a sports writer but also is always considered myself entrepreneurial want to start a business someday and I kind of did with sports internet although it was just a one person newsletter so I don't really consider it that I would say Bill Simmons his career trajectory really speaks to me in terms of kind of balancing like being a voice and a writer and somebody who like speaks about sports but also like thinks about sports media from a business perspective and what he was able to do going from being a writer at ESPN to starting Grant land which is one of my favorite websites to then starting the ringer ended up pivoting really hard into podcasts selling that company to Spotify that's just somebody who like speaks to my interest of sports writing Sports media but also the business of sports media yeah he's he's done a really good job I'm not a super super close follower but I've heard of them so that probably means a lot yeah I think that does me a lot yeah awesome well kind of listening great thank you for coming on this is really interesting for people anyone interested in media newsletters Sports hopefully we we talk through a lot of interesting stuff so thanks man this is awesome I really appreciate you having me on in the awesome conversation thank you for tuning in to the peel a lot of takeaways from Kendall and I personally learned a lot someone who writes a Weekly Newsletter myself if you want to support the show the best ways as always hard to leave a review wherever you're listening like comment subscribe on YouTube and share this with one friend who might like if you don't want to miss an episode subscribe to the newsletter in the show notes and you'll get new ones in your inbox the moment they drop thanks again for tuning in see you next time foreign

Channel: The Peel with Turner Novak

Views: 7,523

Keywords: sports, newsletter, startup, Axios, the peel, banana capital, turner novak, kendall baker

Id: 4es4p7sFMf0

Length: 92min 58sec (5578 seconds)

Published: Thu Aug 10 2023