# My Biggest WINS & REGRETS Of 2023

Channel: Greg Isenberg
Video: https://www.youtube.com/watch?v=mWXOSNq6b8E
Duration: 36 min
Language: English
Words: 6412
Transcript page: https://viewrankai.com/tools/youtube-transcript/mWXOSNq6b8E

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[0:00] hello I'm going to do a 2023 year review not going to hold back want to tell you about my biggest wins my biggest losses my epiphanies my productivity unlocks my net worth update my personal investment breakdown my social media update and more I don't want to hold back at all and the idea is if I share some of these things with you hopefully it triggers an idea in your own business or your own life and that's all I got asked for so if that sounds cool uh I'll get started so big wins I got married so I'm 34 got married had a small wedding with our immediate

[0:45] families small ceremony we had dinner at this cute little French beastro in Montreal highly recommend a wedding like that not a big thing not hundreds of people uh and it was just nice to have both of our families just immediates and conversing eating breaking bread I love that we did like we went to the a court in in Miami Beach and just did it here and then we went back to Canada where we're both from my wife's from Toronto I'm from Montreal and we did a little ceremony SL dinner there so that was big that was really really big and still processing how fun that was and and what

[1:23] it means for the next chapter but that was obviously the biggest win another big win is we bought 50% of a business business which became boring marketing.com which is basically an AI enhanced SEO business so it's some tools that help companies get organic search and that was our first real acquisition the crazy thing is by next year or in 2024 I should say the business conservative conservatively will do $2 to3 million of free cash flow and uh it's quite a reminder of the fact that you only need a couple good ideas to have a wonderful career and life it's kind of like Warren Buffett and Charlie

[2:02] munger's Vibe where they they really just sit on their hands a lot of the year and just try to come up with a few good ideas because if you can do that uh everything else clicks so that was a big win uh the other big win was we produced nice cash flow for late checkout which is our holding company and we continue to grow several cash flowing businesses which is awesome so the hold Co made money all the individual businesses made money so if this isn't product Market fit I do not know what is so our core thesis of community- based products outperforming non- Community Based

[2:39] products seems to be working and that feels really good you know a lot of people ask me how do you know if you have product Market fit well you'll know it when you see it and I definitely feel it and see it another big win is I started writing my newsletter weekly so have a newsletter can subscribe at Greg Eisenberg dcom and I for the longest time had had this newsletter but I would only I would only write once in in a blue moon maybe once every two months three months whenever I felt like I had something to get off my chest that's when I would uh write and I got

[3:16] convinced that writing weekly uh was a good thing to do and I was kind of anti it for a while because I was like how am I going to come up with something that's unique every single week in a deep format and uh I started thinking about Seth Goden he's got this incredible incredible blog that he's been blogging daily for for like 15 years I think it's seth. blog and I realized if Seth can do it daily I can do it weekly and that's exactly what I did some of my posts were longer some of my posts were smaller um but I wrote weekly and it really really

[3:54] impacted all of our businesses because I was able to promote our businesses through the newsletter and it also just made me a lot more clear around my thoughts which was priceless so forget even the promotion of the businesses through my newsletter the clarity that I was able to get was worth it if I just got that Clarity it would be 100% worth it so I definitely recommend starting a newsletter another big win is someone offered us and not just someone someone I really really respect and a top tier investor offered us $30 million of private equity Capital to scale outlay checkout we didn't take it but it did

[4:34] feel quite good always feels good when you get validated yeah that that just that was dope there's no other way to describe it it felt really awesome and although Venture and private Equity isn't for us right now we're just happy to self fund it it was cool to to get the offer and to say no was really cool and the last biggest win is stay true to myself so I didn't get distracted from competition or other Founders trying to build the biggest business or the most amount of followers most amount of likes the highest amount of YouTube subscribers just did what I thought was right and uh maybe that's the biggest

[5:12] win of all no getting married is the biggest win but maybe it's the second biggest win so stay true to yourself so what were some bad big losses for 2023 for me well for one we listen to some bad advice for our Innovation agency which is called late checkout agency someone once told us early 2023 keep your team lean recession is coming your fortune 500 clients will cut Innovation budgets and it it made a lot of sense because we were seeing in the news that tech companies were doing layoffs everyone was saying there was going to be a recession logically that made a lot of sense of course we're not going to

[5:51] higher and higher higher we're just going to sort of do the same and the reality is these companies that we work with need new products to drive D Revenue in community which is what we do we help them build new products that are beautiful and that drive community and turn customers into raving fans they need that even more during a rough market so if things are tough they need these new products so we basically had full utilization of our team the entire year and we lost at least $3 million of Revenue if we just would have not listened to this advice we would had three plus more million dollars in the

[6:27] bank so that definitely sucked and I think we LED on that particular business with this particular thing we LED with fear instead of leading with courage and we knew our team was really really world class and and really we think the best at at this so we should have been on the offense um I wouldn't say we were on the defense we were just kind of just doing our things we had the same amount of clients we we did get gain a few new clients but we were very very uh part you know stayed the course another big loss is you know there's a saying in

[6:58] entrepreneurship Higher One to higher 10 and I wish I did more of that in 2023 those are The Hires that multiply the business when you look back on a year The Higher One to hire 10 people really really Chang the trajectory of where you're going and although we did hire a few we didn't hire enough and last big uh big loss of the year is I didn't do enough two to three day IRL masterminds a mastermind is basically when a group of people come together usually in a similar industry and you spend like a few days together sometimes it's in a different city than you live in and then ultimately those

[7:36] that group keeps you accountable and support each other and help each other out and I I used to do this all the time and by all the time I mean like at least once a quarter you know once a quarter I think is a really good um it's a really good Cadence I guess because of covid I just like got out of the loop of that got out of the habit of that don't do that these are key these are amazing these are these are this will give you inspiration so for 2024 I've got some plans to do a quarterly Mastermind so I can connect with uh people in the

[8:10] industry in these smaller groups because I do think these like big conferences are overrated but these small IRL masterminds underrated so let's talk about some aha moments I had during 20123 so one is that multipreneur is the future of Entrepreneurship so multi R preneurship some of you have heard me talk about this concept it's the idea that someone creates multiple products per year with the aim of creating a company that creates companies so basically what I did with late checkout and when I started lay checkout 3 and a half years ago I considered it a holding company and I considered myself to be an entrepreneur but now I consider myself

[8:52] to be a multipreneur which I think is like a new breed of founder that you're going to see a lot more of us over the next 5 years I think there's going to be a huge wave of successful multipreneur over the next 5 years just like over the last couple years you started to see the wave of solo preneurs all over so maybe you're one of those multi preneurs or maybe you're a solo prer that might involve evolve to a multier but that's just a big realization and different you know I guess now I have a different mindset and fra yeah frame of mind as a multipreneur second aha moment

[9:28] I have had was this idea around IRL is greater than URL meaning there's just so much Alpha in creating products that drive IRL community experiences I think there's so much postco that we can do you know we were glued to our screens how do you get off the screen I had a quote that went viral in 2023 which is the internet used to be a place to get away from real life now real life is a place to get away from the internet and I think that's uh I think it's pretty true I think there's a lot of demand pent up demand to create interesting experiences in person so that's another

[10:07] frame and AA moment that I had in 2023 which might be useful to you too the third is that premium domains work I used to be one of those people that someone would come to me and say oh I just bought this $100,000. comom premium.com for my startup and inside I'm like what that is such a waste of money why wouldn't you spend that on the product why wouldn't you spend that on Direct response that $100,000 could have been 50,000 customers until I saw how much of an increase in conversion rate you can get when it comes to a great.com especially in B2B so I've seen this a few times in

[10:48] 2023 and I'm starting to think that premium domains are undervalued some of them uh so definitely interested in buying premium domains and now I'm like kind of like I don't even want to buy a regular domain I'm like that's I'm out on regular domain so something to think about the other aha moment I have is marry the niche date the product so what that means is you can give up on a product but don't give up on the niche you believe in so it's common for your product to fail when you build something it's product for your product to fail or if you're a content creator it's common

[11:22] that you create content and it's not hitting but don't give up on the niche you believe in so try different things in your Niche don't be so quick to give up the fifth AA moment is I want to hire more Canadians $1 US dollar today is about a135 Canadian so basically hiring in the Great Wide North is 35% off we hired some exceptional Canadians in 2023 and I want to do more of it obviously continue to still hire in the US but only for select high impact roles because I'd love to save that 35% and put that into a premium domain or put that into marketing or put that into a

[11:59] product another aha moment is reach out to people sounds obvious but I started doing that more in 2023 just random reaching out and I ended up meeting some of my heroes you know I reached out to Rivers Cuomo frontman of Weezer some guy who you know when I was 15 years old obsessed with so so cool to to do that all from Twitter and hang out with him in 2023 I even met a business partner of mine in 2023 so this guy Jordan he designed one of my tweets you know I had a tweet and he designed it and I hit him up and U all of a sudden he became a

[12:34] business partner so if you aren't sending a few DMS a week you are missing out and then the last aha moment is buy more companies I remember Andrew Wilkinson co-founder of tiny which is uh similar to a lay checkout a bigger late checkout really in lots of ways worth hundreds of millions of dollars I think probably I think it's worth almost half a billion dollars I was on the phone with him in 2020 and he he asked me he says why are you so focus on building and incubating companies buying is way easier and my response to him at the time was it's way more fun to build and

[13:07] I believe that true today but still want to buy more in 2024 so I just see the opportunity and I think I can do both from our experience with boring we can do both so if you're selling your agency your Marketplace your email newsletter your vertical SAS your social network get in touch with me we're buying community based businesses I had a few product activity unlocks that I wanted to share some of them are very small but are meaningful one is I in 2020 three started to change my desktop wallpaper monthly I always pick minimalist stuff I don't want like something that's super super busy right now I have like a space

[13:46] background it's like a bunch of galaxies but it's it's black and it looks like a bunch of stars when I log into my computer it like fires me up and uh I also I used to be one of those people with like a few things on my desktop maybe more than a few things I I care to admit you know maybe not the cleanest desktop and in 2023 my desktop was super clean I wouldn't let a file Linger on it so the productivity unlock is yeah just change your your wallpapers make it a point to do it and keep and do do some cleaning second productivity unlock 2023

[14:19] salads for lunch call me basic but salad is healthy keeps it light that way I'm not working and it's like heavy in the afternoon or have any crashes so I I do recommend a salad for lunch I probably do it four times a week put some protein ideally in there as well put Chicken shrimp steak whatever floats your boat and uh less crashes and then just DND mode on desktop and mobile Nob brainer you can still set it so when certain people call they're it's very important husband wife kids parents whatever that it it comes through but you got to focus on on the task at hand

[15:00] and the last one relates a little bit to this which is I hide I I'm on a Mac I hide my top bar and like the top bar where you know it shows the Apple icon and stuff like that and it only shows up if I hover over it I just want to focus on the task at hand that's been a productivity unlock as well and I also hide the dock at the bottom so I have to have to hover over it to see it and I also use ARC browser which is like this new cool browser that when I am in it I don't see the sidebar I've hidden hidden

[15:36] the sidebar so it's a full screen browsing experience which is also been a productivity unlock so let's talk about um my update on my audiences how am I doing on my newsletter in January 2023 I had 36,000 subscribers today I have 72,000 subscribers so pretty good but I didn't spend spend any money on Advertising unlike my peers who have a lot of a lot of my friends spent hundreds of thousands of dollars on advertising and probably got their money back so the question to me was should I have written weekly and grown like paid for ads at the same time maybe but I wanted to prove to myself and prove to

[16:16] you person who you know I'm writing to that I can produce value so I didn't do both at the same time was that not thinking big enough maybe you let me know in the YouTube comments if you feel that way Twitter a year ago I had 280,000 followers today I have 361,000 followers which I think is pretty good uh the interesting thing is most of the followers of that 81,000 people who came and followed me in 2023 came from a a select like two three four five tweets a very small amount of tweets two weeks ago I had a tweet had 70 plus thousand likes and was seen by

[16:58] 20 million people just goes to show you that you got to continue to be consistent and you never know when you're going to pull the slot machine and the algorithm gods are going to let the floodgates open so that's Twitter for you and also some other platforms but definitely my experience with Twitter YouTube subscribers I start you know a year ago I had about 8,000 subscribers today I have 11,300 YouTube is hard but I'm not giving it up I think it's a worthwhile investment honestly Please Subscribe uh uh so I know that you're enjoying it that's the only way I can know um but I've given it a lot of work

[17:35] I started doing these five to 10 minute videos um I did about five or six of those where I break down people like Ryan holiday and Jack Butcher and Colin and Samir and I talk about multi preneurship so I'll do these shorter videos not just long form and not just shorts and I thought actually that that would get me like go viral kind of like how that one tweet I had got 70,000 likes but it hasn't happened yet but I'm still a Believer so I'm going to continue to invest in it but yeah let me know if uh let me know if you don't like it I

[18:10] I'm I you know I think that some of the videos are valuable so I'm going to continue doing it the podcast my podcast it's called where it happens you're listening to it probably uh this is this is the podcast um no growth 2020 2 I had 360,000 downloads in 2023 I had 360,000 downloads so there's been no growth but the podcast has been a lesson it reminds me of the quote over the years I've learned that the first idea you have is irrelevant it's just a catalyst for you to get started then you figure out what's wrong with it and you go through phases of denial Panic regret then you finally

[18:52] have a better idea and the second idea is always the important one so what do I mean by that I mean I started the podcast at the end of 2021 I had a co-host that didn't last and I shifted it from there I shifted it again and only towards the end of 2023 did I really really feel as if I started to get a grapple of what what I want my podcast to be and I want it to be an ideas podcast I want I want people to bring I you know bring ideas I want to hash out ideas I want them to be ideas that are powered by Community powered by

[19:26] internet audiences powered by the internet I don't want to do another interview style podcast I think there's enough of those so although the podcast wasn't successful in the sense that it didn't get millions of downloads anecdotally I feel like over the last six months a lot of you have reached out to me and have said hey I really enjoy the podcast and I like where it's going so I'm going to continue creating it for you and uh yeah just a reminder that all these things are Evolutions all right and last social platform Linkin a year ago I had 10,000 followers now I have 82,000 followers I'd been sleeping

[20:04] on LinkedIn and I had already been writing tweets for years so yeah what I basically do is I take my tweets and I put it on LinkedIn simple as that and I comment you know with my community there um and that's it so nice to have that audience okay products I loved using in 2023 and I'm not involved with any of these products I just I liked using them um so the ones that came to mind is clack KL a c k for those of you who love the sound of mechanical keyboards clock clock clock clock clock I'm one of those people I feel it feel

[20:44] like it's pretty satisfying when I do that and uh the problem with doing it though is it's loud and it gets annoying for people in the room and if you're on a call it gets annoying if you're typing other people are like what is that so clock isett pretty cool cuz it's just an app that you download in the Apple Store on your Mac and you could set it up and you can make it different you know different volumes do you want it loud do you want it balance you can change the what the Clack sounds like do you want it to be clack clack clack do you want

[21:16] it to be click click click it helps you do that it's $5 and it makes me feel like I'm being more productive because I'm I'm clacking away I don't know can't I can't explain it but clock helps Apple Studio display so I'm looking at you now if you're watching this on YouTube on a Apple Studio display it's $15.99 which is absolutely crazy for a screen you know screens cost a few hundred dollars but I enjoy writing on it so much more I enjoying being in my being just on the computer so much more so it pays dividends and you stare at this thing eight hours a day at least so

[22:01] you want something that's beautiful 5K and I I don't know man it's beautiful what can I say I love looking at it too it's like a piece of art so highly recommend the third product I enjoyed dabbling into in 2023 was fire is fire belly tea so I'm a coffee guy but if you're watching this on YouTube this is some tea and uh in the afternoon this is the afternoon while I'm recording this I I become a tea person so coffee in the morning tea in the afternoon better for sleep I just love enjoying I enjoy just sipping working sipping working sipping working and you can't do that unless

[22:39] it's decaf I guess coffee all day or else you you know just unsustainable to have 10 cups of coffee a day so Tea's been really great and Firebelly which is loose tea my my friend Harley finlin president of Shopify got me onto it because he's a co-founder of that company and I steep My Own tea it's a it's a ritual I love doing and I think we got tea most people got tea wrong at least in North America like we think of tea as tea bags but once you have real loose leaf tea that's delicious it really does um change the game and it's a beautiful

[23:16] experience feels really good it's doing something to me too I don't know I I I I think clear I can't recommend it and not Firebelly tea we're going to I'll put the links to all these products in the description so you can you can try some of it if you're interested um the fourth thing is Beam Beam dream so like many Founders I have trouble sleeping so instead of grabbing a prescription pill in 2023 I started using dream powder when I can't fall asleep and I sleep like a baby it's this cocoa that you have you mix it up it's like a mix of like melatonin some

[23:51] CBD some RI lanine I think is another one thing in there and I know what you're thinking you're likew I tried all these things and it doesn't I still can't sleep I don't know it's the combination of all of them make this thing like work like a charm like I'm out I sleep like a baby so highly recommend beam probably one of the biggest Lifesavers that I had in in 2023 because if you're tired all the time it's just good luck being productive and possible and honestly good luck like enjoying your life like it's tough uh if you're tired you feel like this weird you're in this weird State it's cloudy

[24:32] it doesn't feel good you're more agitated so not fun and last product I love using the yumo hiyoshi porcelain mugs I went to Japan a few months ago and I found these we watching this on YouTube these little cups mugs by an incredible designer and Porcelain and I love the sound of it and I love the color way is yeah I think a lot of people including myself were using just like regular mugs and upping my mug game din wear game was helpful 2023 and don't just get the big box Walmart stuff it's worth it if you're especially if you're working from home make your make your space feel spiritual

[25:16] make it feel amazing make it feel like you're excited so these little things and and even if you don't work from home like these mugs are are amazing and a a lot of my friends talk about the Ember mug which is that that mug that is like a smart mug that keeps your coffee or or beverage warm at a particular temperature and I thought about getting that and then I went the complete other direction yo mugs are like the complete opposite and uh it's okay if your coffee gets cold it's okay if you want to heat it up it's okay if you want to brew something a new one you know like you

[25:51] don't need to be productive eight hours a day in front of the computer not moving you know I think having having these little breaks are really helpful especially for creatives so those are the products top products I loved using next thing I want to talk about is my net worth it's gone up 20% year-over-year and I wanted to do a breakdown of my invest Investments as of December 20123 this is not Financial advice do your own research just telling you what I have done so I'll break it out in order of biggest to smallest Holdings spy which is the ticker for um S&P 500 so basically the S&P 500

[26:32] is 20% of my investments private equity which is VC Angel Investments it's about 177% of my net worth spy which is the value investment part of the Spy S&P is about 8% Berkshire halfway A and B is 8% Microsoft 7% Amazon 6% wld which is cloud companies it's the top 100 Cloud companies by besser it's 5% that's a newer trade my thesis there was that all these Cloud companies and SAS companies are going to add Ai and they're just going to be much more valuable so that's my thesis there cash 5% fixed income 5% Apple 4% Google 3% I had a bigger stake in Google and

[27:25] trimmed it a little bit Roy Roy Ro bank and I trimmed it because of and put it into Microsoft basically Royal Bank of Canada 2% good dividend stock TD Toronto Dominion another large Canadian Bank big dividends 2% other stocks 3% real estate 3% Bitcoin and ethereum 2% and uh before you crypto people come after me and and say why why don't you have more in Bitcoin and ethereum well number one I think one to 2% is is a good amount for people to start with and uh number two I have backed some web 3 fund managers crypto fund managers some of my private Equity Investments are in crypto web 3 type

[28:11] thing so there's a few probably a few extra percent there in terms of my net worth update I don't count late checkout Equity I don't count my 401k I don't count my car my Volvo it's on in that calculation so that's my net worth update and then the lake checkout Holdings update what's going on with our businesses we talked a little bit about them but I'll go I'll go a bit deeper so we've got a few businesses we're running one is the late checkout Innovation agency so I think of think of this as like the Moder day Ido or the McKenzie for product design but we've got this

[28:46] Special Sauce which is communitybased design which is like we get into a community we understand them we design for them I think this is going to be a big year for that business for a few reasons companies have like laid off the tech companies have laid off a lot of people but they still need products and uh so we're getting a lot of inbound there and uh yeah I just think uh there's an opportunity here so uh we've got some incredible case studies of adding Bill literally billions of dollars of market caps to companies through products we've created so that's the thing when you're building like a

[29:20] Innovation type agency like the case studies are really important and that stuff takes time so I expect that business to do several million dollars of free cash flow 2024 boring marketing.com I can't believe the growth of this business started like s months ago it's 28 employees and and honestly the growth of the boring marketing movement so like this whole idea of you know you've heard of boring businesses you might have not heard of boring marketing we helped invent that movement that concept our Twitter is 30 thou almost 30,000 people this year I think it's 29,000 people people definitely resonate with the concept the business is flying and then

[29:59] we often joke internally that boring will turn into its own hold holding company and it'll be bigger than lay checkout and we recently expanded the business from just SEO to paid ads and some new Services coming soon so that's really going to make this business fly I'd expect this business to be 60 plus 70 plus employees by the end of 2024 third business you probably need a robot.com we started it this year it's a community for people interested in Ai and automation we added a newsletter there's 60,000 people signed up uh we're still trying to figure out like the business angle of it like we've sold some things

[30:40] we've sold something called robot pass which is basically a way to get you pay like 100 bucks or something and you get discounts on all the AI tools we've done stuff like that we did a Asing course like an email based course that you can pay for paid Community type stuff so I think we're still trying to figure out how do we monetize it but being in the center of AI and really you know learning and about it and and that's another cool thing about building a community is it allows you to be a center of gravity for some really cool people so that's been really awesome

[31:17] meet dispatch.com so is at a sixf figure a month business and it's been an interesting experiment clients love us to be their design partner we've done some really cool work but there's actually a bigger opportunity in 2024 we're going to evolve it I'm not ready to talk I don't think I'm ready to talk about exactly what that is but TBD stay tuned Community Empire so Community Empire is a membership we launched it a few months ago uh it's for people who are interested in building businesses powered by community so it's basically people like me who are into the same sort of stuff I'm into and it's

[31:56] definitely working we priced it so low to basically make it a no-brainer so it's on this platform called school it's $99 a month and if you want to start your and we basically say everyone should start a school for a lot of reasons and but the biggest reason is just it's an incredible lead a community is an incredible lead magnet call a community magnet so if you have an internet audience and you want to get their emails you don't want to be reliant on Twitter or Instagram you funnel them into a community you get their emails you nurture them and you sell them a product that could be a paid

[32:35] product like you can charge for access to a paid Community but it can also just be like a a SAS product a consumer software business a physical location cpg coaching agency so yeah launched a couple months ago we're already doing $20,000 a month of Revenue people love that they get the you know they're paying $99 a month and they get the free school which cost $99 a month usually but free with our group My Hope Is that I acquire someone's business in here like they they go through our playbooks because basically Community Empire is like all my playbooks like distilled plus like peer-to-peer mentorship plus a bunch you know these

[33:16] things called Sprints anyways the point is you can check it out if you're interested but the point is like the real value here is not to make $20,000 a month although that's like pretty awesome cuz if you think but it's a quarter of a million dollars if you value that at 10x AR that's like $2.5 million Enterprise Value created overnight like some of these paid communities like a lot of people should start paid communities so yeah anyways that Community Empire I'm excited to see where it goes I'm not sure where it's going to go uh that's the thing with Community Based you know paid communities you kind of have to see what

[33:52] people want and where you know like for example I would have never thought that we would do a monthly email with here's like two or three niches and and that we we're seeing and here's the trends and like here's some business ideas like I never expected it to be a monthly business idea like almost research trendy type email um but people people wanted it people wanted people yeah people wanted it so we'll see where it goes and uh yeah we've also got a bunch of experiments that are cooking in the holding company and I'll talk more about that uh in the new year I think with the holding

[34:29] company I just really want to embody the build skyscrapers not strip malls mentality meaning like we've got a bunch of businesses that are really working let's go build experiments for these businesses uh instead of incubating 10 new businesses so we will be incubating a few new businesses we'll be buying a few new businesses but we're really focusing on adding fuel to the fire to a bunch of these which just are really working and uh it just goes to show you like I started you know three and a half years ago I I had basically no no followings on the Internet or very small followings and uh I was a guy who

[35:10] created Venture back startups now I'm a bootstrap got a bunch of businesses running having way more fun loving writing loving podcasting uh feeling really energized and thank you know it's corny to say but thank you thank you for listening thank you for watching thank you for replying thank you for liking thank you for subscribing and uh I hope I added value to your life in 2023 and I will continue to do that in 2024 so let me know in the comments if I did if you have any thoughts about this share this video share this podcast with your friends your family anyone who you think could be useful too and uh hope

[35:54] you have a great great start to your 2024 let's go get it

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