Nathan Barry Archive

Andrew Gazdecki is the founder and CEO of MicroAcquire, the world’s most founder-friendly startup acquisition marketplace. MicroAcquire helps entrepreneurs buy and sell startups.After founding and later selling two successful startups, Andrew decided there needed to be a better way to connect buyers and sellers in the startup marketplace. He founded MicroAcquire to fill this void in the startup acquisition arena.In this episode, Andrew shares how he grew his Twitter audience from 30,000 to 70,000 followers in a few short months. He uses his connections with others, his partnerships, his brand, and savvy marketing techniques to boost engagement and attract followers. It’s a fun and entertaining episode, and I think you’re going to enjoy it.In this episode, you’ll learn:The one thing you should spend at least half of your startup’s budget onProven strategies and tactics to grow your Twitter accountHow to bootstrap your business and retain your autonomyLinks & ResourcesTechCrunchCameoEffieEmpire FlippersFlippaBizness AppsSam ParrStripeBaremetricsChartMogulBumbleBrandarrowBootstrappers.comY CombinatorSalesforceNick HuberDavid CancelJosh PigfordClearcoAngelListAvaloqNaval RavikantDharmesh ShahThe Ladders of Wealth Creation blog postAndrew Gazdecki’s LinksFollow Andrew on TwitterFollow MicroAcquire on TwitterEpisode Transcript00:00:00 Andrew:I’m a big fan of stair-stepping and entrepreneurship. One of my favorite tweets that I’ve ever written is, “Start with an agency, get to cashflow positive, and then bootstrap an asset—whether that’s a SaaS company or your e-commerce business—sell that asset, become financially secure, and then do whatever you want.”Along the way, you prepare yourself for the next stage of business. 00:00:35 Nathan:In this episode, I talked to Andrew Gazdecki, from MicroAcquire. Andrew started a couple other businesses and sold two of them. In that process, he decided there needed to be a better way to buy and sell businesses. So, that’s where MicroAcquire came from. Their marketplace originally focused specifically on SaaS businesses, but they broadened to all of software.The reason I want to talk to him—he doesn’t write a traditional newsletter or something like that—but he uses audience really well to grow MicroAcquire. He uses his personal brand connections with others, partnerships, a bunch of fun things.We get into how he grew his Twitter audience from 30,000 followers just a couple months ago, to over 70,000. His approach to Twitter, some of the arguments or beefs that he started with TechCrunch and others, and where he thinks those lines are.We also get into how he uses Cameo; he has these great ads announcing partnerships and others from Russ Hanneman on Silicon valley talking about this, and they’re really entertaining.So, there’s a lot of fun things in this episode, and I think you’re going to like it.I’ll get out of the way, and we’ll dive in.Andrew, welcome to the show.00:01:41 Andrew:Thanks for having me, Nathan. Always a pleasure to be chatting with you. 00:01:44 Nathan:There are a lot of companies in the brokerage/help-me-sell-my-business space. I think of Effie International, Empire Flippers, Flippa, all of these. So, one, you’re going into a really crowded market with MicroAcquire, and then, two, you’re coming at it like you’re a force of nature.Sam Parr and I we’re actually talking about this, of how some people start a project and it’s like, “Oh, I’m going to do this thing.” And then other people do effectively the same thing. I mean, it’s different in a lot of ways, right? But the same category, and come in and just completely dominate, and grow so fast, and it feels like a fundamentally different thing.What’s your take on that, of coming into a crowded space, and then the amount of momentum that you’ve come in with?00:02:34 Andrew:Yeah. I have a lot of respect for all those companies that you mentioned, and appreciate the compliment.The market that is specifically acquisitions hasn’t seen a lot of innovation in a decade. Two of the businesses you mentioned are service businesses, Flippa being a marketplace. I looked at that, and I just thought, there’s an angle here where sellers could benefit more than the buyers, and I felt buyers were benefiting. So, I took a left while everyone was going right.Then coming in from an entrepreneur’s view instead of a buyer’s view, or an investment bankers view, or an MNA advisor view, this was me saying, okay, I’m gone through two acquisitions, I think I have a few unique insights into what it would take to make me comfortable putting my business, generating millions of dollars, on a new marketplace. Then, what information and educational pieces would I need to feel comfortable to facilitate an acquisition.So, I just built what I felt acquisition should be. We still have a long way to go. We’ve done a really good job of connecting buyers and sellers, and all the acquisitions are facilitated off platform. We’ve been working on a lot of tooling to really add value to the acquisition, if that makes sense.So we’re looking to innovate on things like due diligence or even simple items like writing a letter of intent or streamlining escrow, because everyone complains about escrow.com. so yeah, I mean, sometimes it just happens in markets. Like a new entrant comes in with a different angle towards the problem And different viewpoint. and I think my unique, insight there was just, I had been on. The side of the table that maybe the other, companies had not. but it’s also, a giant market. So I, think, arising boat lifts all tides. So, you know, we’re here to my require. I just made my group or to help entrepreneurs get acquired and, and, succeed.And so, I think also as, you know, Mike require pick steam and helps everyone else in the market as well. So, but, yeah, I don’t have a good answer to that. I don’t know. I think if I, if I, this, this will sound cheesy, but you know, I, I I’d like to say I built my group hire would love, like I launch...

Sherrell Dorsey is the founder and CEO of The Plug, a publication and community for news, insights and analysis on trends in Black innovation. The Plug features stories that show the substantive ways Black people engage with the innovation economy, including analyses of modern technologies.On today’s show, Sherrell shares about building an audience and growing The Plug. We talk about sponsorships, The Plug’s revenue model, and her background in journalism and how she brings that into her current work. We also talk about choosing a niche, staying consistent, and much more.Sherrell has worked in marketing and consulting for companies such as Uber, Tresata, MarketSource, and Build The Good. Sherrell has also worked as a correspondent for Fast Company, Essence, Next City, and Black Enterprise. She earned her master’s degree in data journalism from Columbia University.In this episode, you’ll learn:How to grow your subscribers when first starting outDifferent strategies for monetizing your newsletterThe right way to include advertising in your newsletterTradeoffs between having a team and working as a solopreneurLinks & ResourcesClay HebertMonica MeltonFarnam StreetShane ParrishRyan HolidayDaily StoicJames clearUberGoogle FiberMicrosoftFast CompanyThe RootBlack EnterpriseGoDaddytheSkimmSignalBloomberg TerminalBusiness InsiderThe Moguldom NationSherrell Dorsey’s LinksFollow Sherrell on TwitterThe PlugThe Plug newsletterHBCU newsletterTPinsights.comEpisode Transcript00:00:00 Sherrell:I think that we’ve gotten into this very fast pace, and this idea of constant information and voices in your head. I don’t know that more information is making us a better society. I think that this idea of community and grappling with ideas, calling things out or bringing things to attention, but having something meaningful to say really outweighs just being visible all of the time. 00:00:31 Nathan:My guest today is Sherrell Dorsey. Sherrell is the founder of The Plug, which is a newsletter, and really a publication at this point, about the black tech ecosystems and all the interesting things that black and brown founders are doing in technology and business. She started in 2016, and she’s built it up to have a full-time team of five people now.I’m so impressed with what she’s built. We get into talking about sponsorships, the revenue model, how she built the audience, her background in journalism, and how she brings that into what she’s doing now. I actually grew up in tech and some of the ecosystems that she was a part of that inspired her.We talk about choosing a niche and staying focussed there. We talk about consistency. There’s really a lot of things in this episode. I love what she’s doing and how she’s built this niche business into something that now employs full-time journalists. At a time when a lot of other publications are dwindling, she’s growing.So, let’s dive into the episode.Sherrell, welcome to the show.00:01:35 Sherrell:Thank you so much for having me.00:01:37 Nathan:I actually want to start talking about experimentation. We’re going to jump around a little bit. You like to run a lot of experiments, and you’ve taken an approach on experimentation where you’re doing it at a stage in the business where you have a lot going on. A lot is working. This is a point where I see a lot of content creators freak out and stop experimenting because they’re like, “This is what my audience likes. I have to show up in exactly this way.”So, they don’t experiment. Even at this level of success, you’re like, “No, experimentation is a core part of what we’re doing.”Could you talk about that, and some of the experiments that you run, and then your mindset around it?00:02:12 Sherrell:We’re constantly challenging ourselves as a team, and trying not to get bored. Part of our experimentation may have more to do with the attention deficit issues that we have as a team, as a collective. Maybe not as much as our audience, but we also assume that they also have attention issues.Let’s be honest, there’s so much competing for our audience’s attention, right? I mean, outside of the inbox, theres social media, there’s the day-to-day of all the crazy, all the push notifications. So, for us, experimentation really is at the core of challenging ourselves to face something new and interesting, and really tapping into what.The sort of timeliness of news, and really finding a way to put it into our voice and share some of our opinions as well. Even with running The Plug’s weekly briefing experimentation is really even just how I got started. The Plug for me was an experiment. I was getting up at 5:00 AM, pulling together a newsletter, wanting to cover diverse voices in tech.Doing it just as this labor of love, and also nerdiness and curiosity, and it started to grow. Then I said, well, maybe I can do this every single day. Then I did it every day. Then at some point we realized, hmm, are people having inbox fatigue? What if we slow things down and really make people cherish every single sentence that we’re writing in our newsletters, and giving them a long and deep side of slow conversations on Monday mornings as they’re starting their day.We’ve seen those questions that we’re asking kind of manifest in this idea of experimenting with just our curiosity. We’ve seen that well, I mean, honestly, Nathan, we’re getting 45% to 48% open rates on every single newsletter, and it has been pretty consistent.When we were in the daily phase, we were starting to see those open rates go down. People just didn’t even have enough time to read. So, again, we start with the question, “Well, what if, or how do we personally sort of engage with our news and with our information, and how do we create a moment of almost intimacy with our audience and our subscribers?” Where instead of just having the breadth, we can actually have the depth.00:04:40 Nathan:Yeah. I want to talk about the consistency and the schedule later in the episode, but let’s go there right now because I think a lot of...

Matthew Kepnes runs the popular travel blog, Nomadic Matt, and also writes a successful newsletter. In fact, Matt’s newsletter is one of the biggest I’ve had on the show. His book, How to Travel the World on $50, is a New York Times Best Seller.After a 2005 trip to Thailand, Matt decided to leave his job, finish his MBA, and travel the world. Since then, he’s been to nearly 100 countries, and hasn’t looked back. Besides being a New York Times best-selling author, Matt’s writings have been featured in countless publications. He’s a regular speaker at travel trade shows, and is the founder of FLYTE, a non-profit organization that sends students overseas to bring their classroom experience to life.I talk with Matt about his unique approach to running his business. While others are building online courses, Matt has shifted to doing more in-person meetups and events. We talk about his newsletter, and we also talk about growing your Instagram follower count, scaling a business as a solopreneur, and much more.In this episode, you’ll learn:When & why you need to start outsourcing day-to-day tasksMatt’s email opt-in strategies and tips to get more subscribersThe most important metric about your email listHow to quickly get more followers on InstagramLinks & ResourcesBlue Ocean StrategyMatadorLonely PlanetBlue Ocean Strategy bookPat FlynnWomen In Travel SummitTraverseCheryl StrayedConvertKitTravelConFinConPodcast MovementWorld Domination SummitHootsuiteTim FerrissSeth GodinOptinMonsterSeth Godin: This is MarketingRick StevesNathan Barry Show on SpotifyNathan Barry Show on Apple PodcastsMatthew Kepnes’ LinksMatt’s websiteFollow Matt on TwitterMatt’s InstagramThe Nomadic NetworkNomadic Matt PlusEpisode Transcript[00:00:00] Matthew:When I started these courses back in 2013, there wasn’t a lot of folks. Now you have so many people with courses, so many Instagrammers and TikTokers selling their stuff. It’s sort of like, is this worth the time to really invest in it when my heart really isn’t in it? How can I maintain 400K in revenue a year? Is that the best use of our resources? The answer is, not really.[00:00:33] Nathan:In this episode, I talk to my long time friend, Matt Kepnes, from Nomadic Matt.Matt’s got a travel blog that’s wildly popular, and he gets into that—shares all the numbers. He’s probably one of the biggest newsletters that I’ve had on the show, so far.What I love about him, in particular, is how thoughtful he is about his business model.Most people are just adding more courses and figuring out how to grow revenue; honestly, what’s now fairly traditional ways, and it’s quite effective. Matt takes another approach. He gets into in-person events and meetups. We get to talk about why in a busy, crowded online world, he’s actually going offline.I think that Blue Ocean Strategy he references, the popular book by the same title, I think it’s interesting, and it’s something worth considering when some of the online strategies don’t work. We also get into a bunch of other things like growing his newsletter. Like I said, it’s quite large.Then, also growing an Instagram following. Instagram is not something that I’m going to actively pursue, but it’s interesting hearing his approach of what you do if you’re at 5,000 followers on Instagram, and want to grow to 50,000 or more.So, anyway, enjoy the episode.If you could do me a favor and go subscribe on Spotify or iTunes, or wherever you listen if you aren’t subscribed already, and then write a review.I check out all the reviews. Really appreciate it. It helps in the rankings, and I’m just looking to grow the show.So, anyway, thanks for tuning in today. Let’s go talk to Matt.Matt, welcome to the show.[00:02:06] Matthew:Thanks for having me, Nathan. I’ve been trying to get on this podcast for ages.[00:02:10] Nathan:Well, don’t say that, that’ll make people think they can get on just by asking. Really, you came to my house and stayed in my cottage on the farm, and then you’re like, “Yo, have me on the podcast!” And that’s when I was like, “Absolutely.” But if anyone just asked, that would not be a thing.[00:02:26] Matthew:No, I just mean I finally—I’m excited that I’m worthy enough in my blogging career to be on.[00:02:33] Nathan:Oh, yes.[00:02:35] Matthew:I’ve made it.[00:02:36] Nathan:Yeah. It’s only taken you, what, a decade and a half?[00:02:39] Matthew:13 and a half years. Slow and steady wins the race.[00:02:43] Nathan:That’s right.I actually want to start talking about that side of it, because I’ve been in the blogging world for 11 years now. But even I feel like things changed so much in the first couple of years, even before I entered into the world. So, I’m curious, going back to the early days, what were the prompts for you to come into the blogging world and say, “Hey, I’m going to start publishing online”?[00:03:10] Matthew:Yeah. You know, it was a very haphazard, there was no grand plan. Like I had Zanger when people had Zeno’s, which is, you know, a personal blog, way back, you know, 2003, whatever. And so what, I went on my trip around the world in 2006, I just kept updating this Zynga. You know, it was called, Matt goes the world and it was just like, here I am friends here I am.And then, you know, everyone was really excited in the beginning. And then after a while I got sick in my update because the know their back of their office job. So I kinda just forgot about it until I came home and January, 2008 and I need money. And so I started a temp job, and I had a lot of free time and I really just hate...

Andrew Warner has been part of the internet startup scene since 1997. Andrew and his brother built a $30 million per year online business, which they later sold. After taking an extended vacation and doing some traveling, Andrew started Mixergy. Mixergy helps ambitious upstarts learn from some of the most successful people in business.Andrew and I talk about his new book, Stop Asking Questions. It’s a great read on leading dynamic interviews, and learning anything from anyone. We also talk about longevity and burnout as an entrepreneur. Andrew gives me feedback about my interviewing style, the direction I should take the podcast, and much more.In this episode, you’ll learn:Why you need to understand and communicate your missionHow to get your guest excited about being interviewedWhat to do instead of asking questionsHow to hook your audience and keep them engagedLinks & ResourcesConvertKitGregg SpiridellisJibJabAli AbdaalThe Web App Challenge: From Zero to $5,000/month In 6 MonthsGrooveZendeskHelp ScoutJordan HarbingerNoah KaganBob HilerSeth GodinMorning BrewAlex LiebermanKeap (formerly Infusionsoft)NotionSahil BloomRyan HolidayBrent UnderwoodGhost Town LivingTrust Me, I'm Lying: Confessions of a Media ManipulatorDamn GravityPaul GrahamY CombinatorNathan Barry: AuthorityIra GlassNPRThis American LifeBarbara Walters Richard Nixon interviewOprah interview with Lance ArmstrongMatt MullenwegChris PearsonConspiracy: Peter Thiel, Hulk Hogan, Gawker, and the Anatomy of IntriguePeter ThielGawkerNick DentonThe Wall Street JournalRohit SharmaSanDiskJason CalacanisDickie BushSean McCabeDaily Content MachineJordan PetersonTribesWarren BuffetSam WaltonTed TurnerGothamChessLinkedIn Learning (formerly Lynda.com)Inc.com: Selling Your Company When You're Running on FumesChess.comMark CubanJames AltucherRod DruryAndrew Warner’s LinksAndrew WarnerStop Asking QuestionsMixergyEpisode Transcript[00:00:00] Andrew:The top 10 interviews of all time are news-based interviews. We, as podcasters, keep thinking, “How do I get enough in the can, so if I die tomorrow, there’s enough interviews to last for a month, so I can be consistent, and the audience loves me.”That’s great, but I think we should also be open to what’s going on in the world today. Let’s go talk to that person today. If there’s an artist who’s suddenly done something, we should go ask to do an interview with them.[00:00:32] Nathan:In this episode, I talk to my friend, Andrew Warner, who I’ve known for a long time. He actually played a really crucial role in the ConvertKit story in the early days, and provided some great encouragement along the way to help me continue the company, and get through some tough spots.We actually don’t get into that in this episode, but it takes an interesting turn because we just dive right in.Andrew’s got a book on interviewing. He runs Mixergy. He’s been, running Mixergy for a long time. We talk about longevity and burnout, and a bunch of other things. He dives in and challenges me, and gives me feedback on my interviewing style. Where I should take the Podcast, and a bunch of other stuff. It’s more of a casual conversation than the back-and-forth interview of how he grew his business. But I think you’ll like it. It’s a lot of what I’m going for on the show.So anyway, enjoy the episode.Andrew, welcome to the show.[00:01:25] Andrew:Thanks for having me on.[00:01:26] Nathan:There’s all kinds of things we can talk about today, but I want to start with the new book that you got coming out.This is actually slightly intimidating; I am interviewing someone who has a book coming out about how to be good at interviewing. Where do we even go from here? You were saying that you have thoughts?[00:01:47] Andrew:I have feedback for you. I have a thoughts on your program.[00:01:51] Nathan:I’m now even more nervous.[00:01:52] Andrew:I’ve been listening, and I’ve been following, and I’ve been looking for questioning styles. Is there feedback I could give him? I mean, I’ve wrote a whole book ...

Nick deWilde is a Product Marketing Principal at Guild Education. Guild is a fast-growing startup that partners with Fortune 500 employers. Guild unlocks opportunities for America’s workforce via education and upskilling.Nick also runs his newsletter, The Jungle Gym. The Jungle Gym helps readers build a more fulfilling career that integrates work and life. Before working at Guild, Nick earned his MBA from Stanford Business School, and was a Managing Partner at Tradecraft.Nick and I talk about his relationship with Twitter, and how social media can both serve you, and be a challenge. We talk about individual brands and growing a platform. Nick also shares his thoughts about marketing yourself as an individual, and we discuss how growing an audience plays into your career.In this episode, you’ll learn:Building an audience while working full-timeThree reasons people start newslettersWhat to do when your follower count hits a plateauLinks & ResourcesMorning BrewFastlyJoseph Henrich, The Secret of Our SuccessJulian ShapiroSahil BloomDickie BushMediumTiago ForteBuilding a Second BrainDavid PerellWrite of PassageTradecraftGuildHacker newsJohn Lee DumasPacky McCormickMario GabrieleSeth GodinRachel CarlsonOn DeckGongMatt RaglandCharli PrangleyThe Nathan Barry Show, featuring Kimberly BrooksHarry StebbingsThe Twenty Minute VCIsa AdneyLiz Fosslien, No Hard Feelings: The Secret Power of Embracing Emotions at WorkDiscordRedditPalletCraft + CommerceConvertKitEnoughRyan HolidayJames ClearMarie ForleoRamit SethiNick deWilde’s LinksFollow Nick on TwitterNick’s newsletter, The Jungle GymTo tweet, or not to tweetEpisode Transcript[00:00:00] Nick:I’ve tried to do things in my writing where my employer benefits from them. I talk about work a lot, and whenever I talk about hiring, I mention Gild is hiring. There are things I do to just try to make sure that it still feels worth the company’s while.[00:00:25] Nathan:In this episode, I talk to Nick deWilde, who writes a popular newsletter called The Jungle Gym. He’s got a background in product and growth, and all these things from the startup world. I just love the approach that he’s taken to writing these days.We talk about growing as newsletter. We talk about his interesting relationship with Twitter and social media. How it can really serve you and be this great thing, and then it can also be challenging. Maybe you’re spending too much time on it, or time on it in a way that’s not actually serving you or benefiting you.We talk about the rise of individual brands being used to grow a platform. It’s something I’ve been thinking a lot about, watching Morning Brew and Fastly, and some of these other companies do it. It’s just interesting whether you’re marketing as a company or an individual. It’s just a good conversation. We also talk about audience, and just how that plays into your career.He recently made the switch from a full-time role, to doing more audience-based business stuff. He was just in the middle of that journey. So, it’s a fun place and time to catch up in the conversation.Nick, welcome to the show.[00:01:33] Nick:Hey, thanks for having me, Nathan.[00:01:35] Nathan:I want to start on this article you have, that I like a lot, called, “To tweet, or not to tweet,” That got you ahead. I also happened to go to the Shakespeare festival recently, and watched them do “The Complete Works of Shakespeare, Abridged.”So, you know, I could probably pull off a good, to[00:01:50] Nick:Nice.[00:01:51] Nathan:Be or not to be speech right now. It’s in my head because I think about all the wonderful things that Twitter and an audience beyond that does for me. Then also the negative sides of it. So maybe we dive into that, but I’d also love to hear what sparked you diving in and building an audience.[00:02:11] Nick:Yeah, I’m so conflicted on Twitter, and audience building in general. Like anything, I imagine there’s a fair number of people who you talked to, who are in the writing community, who feel that way. On the one hand, Twitter does so many things for me. Especially over the past couple of years.As we’ve been in lockdown, lives have moved online. I have met and made friends with so many amazing people through Twitter that I wouldn’t have met otherwise. Same with the newsletter, but Twitter is a little bit easier to build those relationships.

Kimberly Brooks is a contemporary American artist and author. Kimberly integrates landscape, figuration and abstraction to address subjects of history, memory and identity. Her work has been exhibited and featured internationality.Kimberly received her bachelor’s degree in literature from U.C. Berkeley, and was Valedictorian. She has taught art as a lecturer and adjunct faculty instructor, and was a featured speaker at TEDx Fullerton.In this episode, I talk with Kimberly about her work as an artist, author, and editor. We talk about how she uses ConvertKit to reach and grow her audience. We talk about what people can learn from fine art, and apply it to their newsletters. We also cover the path to becoming a successful creator, and much more.In this episode, you’ll learn:The secret to achieving your breakthrough momentA job most creators should charge for, but rarely doWhat you should be doing instead of bloggingShould you be posting on Instagram?Links & ResourcesHuffington PostConvertKitCraft and CommerceSteve JobsJohn BaldessariAdobe PhotoshopAdobeLeonard ShlainMilton GlaserMacworldWalt Disney’s ImagineeringWarner Music GroupSeth GodinLeonardo da VinciArianna HuffingtonHuffington Post: Fine ArtLaterAnderson Ranch Arts CenterOtis College of Art and DesignKimberly Brooks’s LinksFind Kimberly on InstagramKimberly’s websiteKimberly’s Ted TalkHuffington Post article, “The Gap Logo, New Coke and the Legendary Walter Landor”Kimberly’s book, The New Oil PaintingEpisode Transcript[00:00:00] Kimberly:The fundamental way to learn is, you imitate, assimilate, and then you can improvise with anything. You’re going to be thwarted in the beginning many times, and you can’t give up. You have to say, “Okay, well, I don’t care if it sucks. I don’t care if I’m going to fail. If I’m gonna fail, I’m gonna fail big. Let’s just go on.”[00:00:29] Nathan:In this episode I talk to Kimberly Brooks. She is a fine artist. So, painting, she has all of her art in galleries, that whole world, which is super fascinating to me. She also plays in the creative world. Newsletters, podcasts, and interviews.She built the whole art editorial section of the Huffington Post. She built that to millions of readers. She’s done all kinds of things in the design community from the early days. So, we riff on that; Mad Men-style ad agencies in the ‘80s and ‘90s. Some great stuff.Then she brings it all the way through to talking about what she does with ConvertKit. How she sets up her sequences, and everything else, and things that people can learn from fine art, and apply to their email newsletters and sequences.So, it’s a fun episode. We have to do a part two, because we filled up all the time we had, and I think I only got through half my questions.So, anyway, I’m going to get out of the way and dive in. So, here we go.Kimberly, welcome to the show.[00:01:37] Kimberly:Thank you for having me, Nathan.[00:01:39] Nathan:There’s so many things I to talk about, because you come to the creator world from a different perspective than I do, though we both share a love for Photoshop.[00:01:50] Kimberly:Oh, yeah.[00:01:51] Nathan:We’ll start with where we met. It was at Craft and Commerce, some number of years ago.I can’t even think. Three years ago? Four?[00:02:01] Kimberly:I think it was three years ago, and it was such a random whim. I don’t even know how I ended up finding it. I fell in rabbit hole. And then I came upon ConvertKit.I was actively looking for a better way to send art show announcements. Because I’m a painter, I’m an artist.I just felt after my previous experiences, I knew how important having a subscriber-based service was. I don’t want to get too nerdy, but I didn’t really like the competitor who shall remain unnamed. But, I found you guys, and I started getting the advertisement for the conference, and it was in Boise, Idaho.And so I thought, I’ll just go. It was like a Ted conference for really creative nerdy people like me, but it was exactly what I was wanting. It was about marketing, which is really such a weird word because it’s really about sharing, and I loved the title.I loved everything about it. I met some of the people that I’m really, really close with now. Then the next year it was canceled because of the pandemic, but it was amazing, and I met you, actually.[00:03:28] Nathan:And, and we had a really fun conversation. one thing that I want to talk about, for you is the intersection between fine art, right. And painting and that world. And then now you’re also in this world of being a writer and a creator in the sense, right. You you’ve been a writer and creative for a long time, but, but it’s, it’s like a different world of the selling things to your audience.And. Earning money directly in that way. And so I want, like, I want to hear that as you like weave in and out of these two worlds and then just your experience there.[00:04:02] Kimberly:Yeah, it’s interesting. I, when I was in elementary school, we had a really competitive game of tetherball constantly going on on the playground. And it was just sort of that pole with a ball attached to a rope we would, people would line up and we would get it, and it was, see how many times, and it was just sort of like, it was very intense and I always felt like being an artist.Being an art to me was it was the pole, you know? So like my pole is art is making art and everything about what I do. I write about it. I interview people about it. I interview other artists about their work. I make paintings 90% of the time in my studio. Like, it’s all about art, you know? So that’s like the beginning.So I do see myself sashaying between different worlds. And I think everybody kind of does that. And then as the bicycle of technology was being built to use kind of lik...

My guest on this episode is music industry veteran, Jay Gilbert. Jay wears a lot of hats. He’s a musician, photographer, marketer, speaker, and music executive. Jay has worked as a creative consultant to many record companies and artists. He hosts The Music Biz Weekly Podcast, is a Co-founder of Label Logic, and runs the weekly music newsletter Your Morning Coffee.Label Logic helps artists, managers, and labels grow their audience and optimize their presence across all platforms. Jay’s newsletter is curated to give a weekly snapshot of the new music business. It’s everything you need to know, delivered to your inbox every Friday morning.I talk with Jay about his shift to being a content creator. We talk about life as a musician, working in the music industry, and being a photographer. We also talk about his management company, and his advice for creators wanting to build their audience. Jay also shares some behind the scenes stories, and much more.In this episode, you’ll learn:Simple hacks to grow your newsletterDefining and reaching your target audienceLow-budget tricks to instantly add new subscribersJay’s #1 metric for becoming a successful creatorLinks & ResourcesConvertKitBen BarnesPeopleJeff MoscowTravis TrittAli AbdaalConvertKit’s Creator SessionsMusic Connect (MRC)ChartmetricViberateSoundchartsPollstarCherie HuAmber HorsburghGlenn PeoplesBobby OwsinskiBruce HoughtonHypebotSound & VisionMusic Technology PolicyNancy WilsonRobloxJay Gilbert’s LinksFollow Jay on TwitterYour Morning Coffee newsletterBen Barnes 11:11 on People.comJayGilbert.netLabel LogicThe Music Biz Weekly PodcastEpisode Transcript[00:00:00] Jay:The harder I work, the luckier I get. You make your own luck. You see these people, and you’re like, “Wow, that guy just blew up on TikTok or, Twitch, or on Spotify, or Apple Music!” Sometimes that happens. Not very often, and it usually it’s a lot of hard work.[00:00:26] Nathan:In this episode, I talk to Jay Gilbert. Jay’s a music industry veteran. He’s been at it for a very long time. What I love is that he’s also made this shift into being a content creator, as well as being a musician and a photographer. So many incredible things. He’s got this newsletter about the music industry called Your Morning Coffee, and he’s grown into over 15,000 subscribers.It’s the thing that everyone in the music industry is reading every Friday morning. We talk about how he grew that, his passion for the music industry, how the industry has shifted, what’s working, what’s not. He also runs a management company called Label Logic where they’re partnering with, artists and managers, and doing these album releases, and so much else.He’s got all these behind the scenes stories, and a lot of advice that is not only for the music industry, but also for any creator looking to build an audience, and endure long enough to get noticed, and to build a brand and everything else. It’s really good towards the end.I also sneak in some selfish questions about what would he do to grow ConvertKit; what’s his advice for ConvertKit entering the music industry.Jay, welcome to the show.[00:01:39] Jay:Hey, thanks for having me, Nathan. Good morning.[00:01:41] Nathan:Good morning.We’ll dive into some of your background, what you’re working on now, but you actually had a pretty big project launch today.What did you launch today?[00:01:54] Jay:Well, when you launch a big project, sometimes it’s like a wedding. You have all this planning, planning, planning, and then boom, there it is. It was pretty exciting this morning. We’ve had to keep quiet about this project. It’s Ben Barnes, who is a pretty famous actor, but most people don’t know he’s a brilliant singer songwriter and pianist.We’ve recorded this really great record. We’ve got some amazing videos, given his relationships in that area. They’re quite special. We launched a window of exclusivity this morning with People Magazine.So, if you go to People.com, you’ll see. the video is debuting. It’s pretty special, and we’re really excited about it. It gets released tomorrow. The song’s called 11:11, by Ben Barnes. It’s pretty cool. I think you’ll dig it.[00:02:53] Nathan:Nice. Yeah. If anyone doesn’t recognize the name, Ben Barnes, he plays Prince Caspian. I’ve been a fan of the Narnia series and all that for a long time. I think my kids actually just rewatched Prince Caspian two weeks ago.[00:03:09] Jay:Have you seen shadow and bone yet?You got to check out shadow and bone. My, my wife and I binged watched it. And he’s, he’s brilliant in that, but it’s a really cool series.[00:03:21] Nathan:Nice. Okay. So maybe with that, of like a snapshot of, of what you just launched, Let’s talk about, a little bit about, logic[00:03:32] Jay:Sure.[00:03:33] Nathan:You know, what types of projects you do. And then we can go back to like the road to get.[00:03:38] Jay:Yeah, well, Label Logic was born out of my partner, Jeff Moscow, and I working in the major label ecosystem for years and years. And we finally got to a point where we were meeting one day for coffee and said, you know, we started our own.So we both worked at universal for a long time. He was there 20 years.I was there 18 years. I worked at Warner music, for five years managing Amazon’s business for we at ADA, globally, which was fantastic. but we decided to do our own things. It’s about seven years ago, give or take,[00:04:16] Nathan:Yeah.<...

Sean McCabe is the founder and CEO of seanwes media, and Daily Content Machine. Sean is a prolific and successful creator, author, and influencer. His course, Learn Lettering, made $80,000 in the first 24 hours. For nearly a decade his podcast, blog, and courses have helped creators grow their brands, content, and skill sets.Sean’s website is a treasure trove of courses and resources for anyone looking for business knowledge and creative support. Sean’s book, Overlap, shows creators how to turn their passion into a successful business while working a full-time job. His podcast includes almost 500 episodes on content creation and entrepreneurship. His latest venture, Daily Content Machine, turns creators’ best content into clippable moments they can share across their social media accounts.I talk with Sean about what it’s like being a successful creator. We talk about growing your audience and connecting with them. We cover how to learn new skills fast, and about developing a growth mindset. We also talk about managing stress as a founder, how to handle burnout, and much more.In this episode, you’ll learn:Why good writing is the foundation of great contentHow to connect better with your audienceLeveraging short-form content to grow your brandPricing at full value without feeling guiltyHow to avoid burnout, and what to do if you’re already thereLinks & ResourcesSean McCabe on The Nathan Barry Show episode 003Craft + Commerce conferenceConvertKitEnoughRyan HolidayJames ClearMarie ForleoRamit SethiSean McCabe’s LinksFollow Sean on TwitterCheck out Sean on InstagramSean’s websiteDaily Content MachineEpisode Transcript[00:00:00] Sean:If you are a founder, you should be in therapy. Full-stop. You need a therapist. I thought I didn’t. I had a great upbringing. I’m all good. Everything’s healthy. I don’t have any problems. The problem was I didn’t know the problems that I had. I didn’t realize what I was stuffing down. I didn’t realize what I was avoiding.There is so much to unpack that you don’t know you need to unpack.[00:00:30] Nathan:In this episode I talk to my friend, Sean McCabe. We’ve known each other for seven years now. It’s been a long time. We’ve been in a mastermind group together. He’s actually been on the show before. Sean is a wildly talented designer. He got his start hand-lettering.I think last time he was on the show, years ago, we were talking about that aspect of his business and how he built this substantial course business. Selling courses on hand-lettering, on marketing, on writing. He’s spoken at our conference Craft + Commerce, all kinds of things. Sean is one of the most prolific creators that I’ve ever known.It’s also super fun that he’s a friend and lives right here in town. We just have a great conversation. We talk about how you create content, which is one of those things that it’s not even how you create content, it’s why. Where that comes from. The internal drive in what you use. Where you choose to have as a source of fuel and energy to put into that creative output.How some sources are really good and productive, and others can be kind of like a house of cards, and it can be harmful. We also talk about scaling teams as a creator. How do you know when to build out a team around your business? He’s done that two different ways. So I get to ask him about some of the things he’s learned and applied differently.I’m going to stop there. There’s a lot of good stuff. So with that, let’s dive in.Sean. Welcome to the show.[00:01:59] Sean:Hey, Nathan, just saw you recently. We were playing volleyball, or something.[00:02:03] Nathan:Or something, like two days ago. You moved to my city. It’s kind of…[00:02:08] Sean:Yeah. It’s horrible. It’s a terrible place. Boise. Don’t move to Idaho.[00:02:15] Nathan:You mean Iowa? Boise, Iowa.[00:02:17] Sean:Iowa. Yeah. Don’t, yeah. Did I do okay?[00:02:21] Nathan:Yeah. That’s exactly what you’re supposed to say. If you Google something about Boise, Google has the accordion of extra questions, or things you might want to know. One of them is, “Does Boise smell?” and it’s just like auto complaints in there.And I was like, what is up with that? I clicked on it, and it’s this satirical article that has 12 reasons you shouldn’t move to Boise. One of them is the city dump is right in the middle of the city. Another one is like that the Ebola outbreak hasn’t been fully contained yet.So it’s not really safe. I think there was something about lava. Anyway, it’s just an article about all the reasons to not move to Boise. So I think you’re right in line.[00:03:08] Sean:Stay, away. That’s what they tell me to say.[00:03:11] Nathan:Yes, but if someone were to ignore that and move to Boise, they could come to our weekly volleyball game on Wednesday nights.[00:03:19] Sean:It’s casual. It’s open.[00:03:21] Nathan:Let’s try it. Yeah. It’s been so fun having you and Laci here. It’s also been fun because you started a new company. Your company is producing and editing and creating all the clips for this podcast. So, connections on so many levels.[00:03:37] Sean:Yeah. We produce this show, like the video show, the audio show, and then find clips and make those clips for social media. It’s been great. We love this show. Our team’s favorite content. So, I’m a little biased, but it’s fun to be on. Because my team’s going to work on this.[00:03:58] Nathan:Yeah, exactly. I made sure to spell your name correctly in the setup, and I know they’ll get it all.I wanted to ask what sparked—like maybe first give a summary of Daily Content Machine, since that’s what you’re spending nearly all of your time on. More than a normal amount of time on. So, what sparked it, and what is it?[00:04:19] Sean:Fun fact. This is not the first time I’ve been on the show. The last time was episode three, 2,624 days ago.[00:04:30] Nathan:Give or take[00:04:32] Sean:I was doing different stuff then. It’s been a crazy journey. Right now the newest iteration is an agency.We produce video clips. We turn long form video shows. If you have a video podcast or other kind of long form video content, we found that the hardest part is finding all the good moments in there, and turning those into short clips. ...

Dave Pell has been writing online for almost as long as the internet has existed. His popular newsletter, NextDraft, has over 140,000 subscribers. NextDraft covers the day’s ten most fascinating news stories, delivered with a fast and pithy wit.Dave has been a syndicated writer on NPR, Gizmodo, Forbes, and Huffington Post. He earned his bachelor’s degree in English from U.C. Berkeley, and his master’s in education from Harvard.Besides being a prolific writer, Dave is also the Managing Partner at Arba, LLC. For more than a decade, Arba has been angel investing in companies like Open Table, GrubHub, Marin Software, Hotel Tonight, Joyus, and Liftopia.In this episode, you’ll learn:How Dave merged his two writing passions into a successful productThe key to building a strong relationship with your audienceHow Dave dramatically increased signups to NextDraftLinks & ResourcesFlickerUnsplashFareed ZakariaJim RomeThe SkimmMorning BrewThe HustleSpark LoopSam SprattDave Pell’s LinksDave Pell on TwitterNextDraft newsletterDave’s new book: Please Scream Inside Your HeartNextDraft appPleaseScream.comEpisode Transcript[00:00:00] Dave:If you have something to say in one way or another, the internet is a great place for people to figure out a way to receive it. So, that’s pretty powerful and still excites me. I still press publish with the same enthusiasm now than I did when the internet first launched.[00:00:23] Nathan:In this episode I talk to Dave Pell, who has been writing for basically as long as the internet has been around. He’s been an investor since the early days. He’s been writing since the.com bust, and even before then. He writes his popular newsletter with 140,000 subscribers called Next Draft.We have this really fun conversation about writing. His writing process. How he grew the newsletter. Bunch of other things that he cares about. Even a few things that I was interested in, like he doesn’t have his face in photos on the internet very much. He has his avatar instead. So, just getting into why that is.He also has a book coming out soon. It’s called Scream Inside Your Heart, which is a fun reference to some memes from 2020. So, enjoy the episode. There’s a lot in there.Dave. Welcome to the show.[00:01:12] Dave:Thanks a lot for having me on.[00:01:14] Nathan:Okay. So you’ve been doing this for a long time. You’ve been writing on the internet since the .com era. So, I’m curious maybe just to kick things off, what have you seen—I realize this is a giant question.What have you seen change? What are some of those trends that you’ve seen, that you either really miss from the early days, or some of those things that you’ve held onto from the early days of the internet, that you’re really still enjoying?[00:01:46] Dave:Yeah, that is a pretty huge question, but I’ll give it a shot. The thing I miss from the early days of the internet is that our democracy was not being destroyed by the internet in the early days of the internet. So, everything we thought we were building, basically it turned out to be the opposite of what actually happened.The part about the internet that I still feel is there, although a little bit less so because of the big companies have sort of taken over all the platforms and stuff, is just the idea that someone can have a passion or a creative output that they want to share with the world, and they can mold internet tools to fit their skills, and then use the internet to broadcast that out, and still become sort of pretty popular withour the “OK” of some gatekeeper at a publication, or at a television studio, or whatever.The indie spirit of the internet still lives on. It ebbs and flows, and has a lot of different iterations. But that was the thing that excited me the most when I first played with the internet. And that’s the thing that continues to excite me the most now.[00:02:57] Nathan:I always think of the newsletter, and your newsletter in particular, is that indie spirit. Is that what you see most commonly in newsletters? Or are you seeing it in other places as well?[00:03:10] Dave:I see it in podcasts. I see it in newsletters. I see it in people sharing their art, sharing their photography on Flicker, and up through the more modern tools. I go to a site called Unsplash all the time to look at images, and it’s just basically regular people sharing their images.Some of them are professional photographers, some aren’t, and they’re getting their work out there, and then some of them probably get jobs out of it and stuff like that. So, just the idea that you can have some kind of creative output and have a place to share it. And try to get an audience for that is really inspiring.It’s a lot harder than it used to be because there’s a few billion more people trying to get attention also, and because there are more gatekeepers now. So, you have to, hope that your app meets Apple’s guidelines, or that different products you might want to share on the internet have to meet certain classifications now, whereas they might not have in the very early days of the internet. But in general, if you have something to say in one way or another, the internet is a great place for people to figure out a way to receive it.So, that’s pretty powerful, and, still excites me. I still press published with the same enthusiasm now that I did when the internet first launched.[00:04:32] Nathan:Yeah. So let’s talk about the main project that you have right now, which is Next Draft. Give listeners the 30-second pitch on Next Draft, of what it is.[00:04:46] Dave:Sure. Basically I call myself the managing editor of the internet. What I basically do is a personality-driven news newsletter where I cover the day’s most fascinating news. I cover 10 stories. A lot of times in each section there’s more than one link. I give my take on the day’s news, each individual story, and then I link off to the source for the full story.When I first launched it, I called it Dinner Party Prep. I provided enough information for you to sort of get the gist of the story. And if there’s topics you want to dig deeper, you just click and, you know, go get the story yourself. So that’s sort of the overview of it.[00:05:27] Nathan:Nice. And you said that you’re obsessed with the news maybe in a somewhat, even unhealthy way. why, where did that come from?[00:05:36] Dave:Y...

Jessica DeFino is a freelance beauty journalist living in Los Angeles, California. For the past seven years Jessica has been writing, researching, editing, and publishing about the beauty and wellness industry. Her work has appeared in Vogue, The Cut, Fashionista.com, Cosmopolitan, Marie Claire, Business Insider, SELF, HelloGiggles, Harper's Bazaar, and more.Before starting her career as a freelance journalist, Jessica worked as a beauty writer for The Zoe Report. She was Director of Communications at Fame and Partners, and worked as a ghostwriter for Khloé Kardashian and Kendall Jenner.Jessica earned her bachelor’s degree in Music/Business Songwriting from the Berklee College of Music. Jessica’s music degree brings a unique perspective to her writing. It infuses each piece with lyrical qualities of storytelling, flow, and connection to her audience.Jessica also publishes a bi-monthly beauty newsletter called The Unpublishable, where she shares “What the beauty industry won’t tell you — from a reporter on a mission to reform it.”In this episode, you’ll learn about:Making lasting connections with your audienceWhy understanding music and rhythm makes your writing betterCapturing and keeping your readers’ attention right from the outsetThe dangers of cross-posting your content across social mediaLinks & ResourcesVogue MagazineAllureHarper's BazaarUrsula K. Le GuinRhymeZoneAli AbdaalJessica DeFino’s LinksFollow Jessica on TwitterThe UnpublishableJessica’s InstagramEpisode Transcript[00:00:00] Jessica:I started writing as a songwriter. The musicality of something is very important to me. So I’ll read my own stuff out loud sometimes. I feel when people can read something and there’s a clear flow and rhythm to it, and the words melt into each other sound nice next to each other, it locks them into the content early on. You want to keep reading because if you stop reading it’s like you’re breaking this rhythm that you’ve started.[00:00:34] Nathan:In this episode I talk to Jessica DeFino. She’s a journalist covering the beauty industry, but she tends to take an approach that’s not as popular with sponsors and publishers, because she’s anti a lot of their products and a lot of the nonsense that is put into the products and the marketing behind it.She’s taking a critical angle and she’s well loved by her readers because of it, but maybe not so loved by the big brands. We talk about how that came about. We talk about her writing style, her approach of using her background in song writing and going to school for songwriting to have a better, more interesting writing style.She gives some tips along that angle, talking about how she launched a newsletter last year and growing that to 9,000 subscribers. How that is a backbone for the rest of her work she does in journalism.It’s a great conversation. So, let’s dive in.Jessica, welcome to the show.[00:01:28] Jessica:Thank you so much for having me.[00:01:29] Nathan:We’ll jump around a whole bunch, but I want to start on the launching of your newsletter. What was the moment when you started to think, okay, I want to actually run a newsletter and start to control my own audience?[00:01:44] Jessica:I had been toying with the idea for a while, and then I think it was, April, 2020, right after the pandemic, where I had gotten into a situation where—I’m a freelance reporter—I had four freelance stories out when March happened, and Coronavirus lockdowns happened and everything was up in the air.The company severed ties with all of their freelancers and basically gave these four unpublished stories back to me, and gave me a kill fee. So it was like I had reported out these whole stories. I had spent months on them, and now I had nowhere to put them, and I gave it about a month of pitching it out to other alums.There weren’t any takers because media was in such a precarious position at the time. Finally I was like, maybe this is the opportunity I’ve been waiting for to launch a newsletter. and I decided to call it The Unpublishable because I couldn’t get anyone to publish this. And yeah, it’s been going, almost like every other week.[00:02:50] Nathan:Nice. Yeah. It’s interesting how these unfortunate moments result in something that’s like, okay, this is actually either a good thing now, or hopefully going to be a good thing soon, but it starts with difficult times.[00:03:05] Jessica:Yeah, exactly. I wanted these pieces to be big. They were stories that I thought were important to tell, and I really wanted them to be in a major outlet. Sometimes with media, you can’t sit on things for very long. It was like, I maybe have two more weeks before they stopped becoming relevant.[00:03:23] Nathan:Yeah. So for context, for anyone listening, what were some of those stories as an example?[00:03:27] Jessica:The first story I published with a piece called “Where are All the Brown Hands?” It was a look into the overwhelming whiteness of the top nailcare companies in beauty. If you would look at their Instagrams or if you would look at their websites, everything was modeled on white hands.As a beauty reporter, when I have to source images for the stories, I don’t want to just be showing white hands. If I’m writing about nail trends or whatever, and it would take me hours every week to comb through places and try to find the trend I was speaking to on a person of color. At one point, I was like, why is this happening and how come it’s so hard?This should not be hard. So, I wanted to do an investigation into it, and just like that the whole process had already taken six months. I was like, you don’t know what’s going to happen in this story. It might be scooped. It might be written by somebody else. It might be irrelevant in another month or so.So, I really wanted to get that out there, and that started it.[00:04:31] Nathan:When you publish a story like that, and you’re used to publishing for a major beauty publication, but you’re publishing it for yourself. What did that look like? What was the process of saying, I have this story that I’ve worked on for a long time, and I have a brand new newsletter and all at once.How did you bring that to life and pull the audience together?[00:04:52] Jessica:Well, luckily at that point I had a mask, a little bit of a social media following just from my work on work, like major publications. Like I had been writing for Vogue and allure. Harper’s bizarre. And I had been pretty diligent about building up a social media audience. So I had a pretty sizable, amount of readers just from Instagram.And a couple of years prior, I had like tried starting ...