Building and growing revenue-driving newsletters for our partners @ Tailwind. Sharing the lessons we learn along the way.

Joined April 2020
56 Photos and videos
Ryan Carr retweeted
I talked my colleagues at @EarnWithMode into starting a new AI newsletter, written by yours truly. I'd love for you to join, it's free! Still working on the format, but it's more geared towards the beginner/intermediate builders out there. If that's you, we'd love to have you.
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1 Apr 2025
This is my mom, Joanie Carr. She passed 11 days ago, at the young age of 60, after 8 months of battling cancer. She was the kindest, most selfless person I've ever known, and the world is better for having had her here for a brief time.
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Ryan Carr retweeted
After running my first newsletter then working with hundreds of others while at SparkLoop, I understood the value of newsletters. When I launched @optaio, I knew I wanted to create one. Most of our early customers have come from cold outreach and referrals, but I’ve been working to fire up our marketing engine. I recently revamped our welcome sequence and post signup flow before turning on paid Facebook ads at a pretty low clip. In the first two weeks, 4 demos booked, 10 people interested in demos (but no closed customers yet). Cold email has been my bread and butter for years, but generating inbound is starting to convert better and with less effort. If you’re in the newsletter world, it’s easy to feel like the space is saturated (it is, to some extent) and that newsletters aren’t effective. Couldn’t be more wrong when done correctly. I was worried I was a hammer looking for nails when we launched Opta’s, but early results indicate it could strengthen our pipeline pretty drastically.
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Ryan Carr retweeted
Today, I’m excited to announce: Newsletter Marketing Summit Our inaugural conference for founders, creators, and marketers building the future of media and education. We already have an amazing roster of speakers, including: ✅ Alex Lieberman, co-founder of Morning Brew and StoryArb ✅ Sam Parr, co-founder of Hampton and founder of The Hustle ✅ James Altucher, bestselling author, entrepreneur, and investor ✅ Jay Clouse, founder of Creator Science ✅ Chenell Basilio, founder of Growth In Reverse ✅ Tim Huelskamp, co-founder and CEO of 1440 Media ✅ Jenny Rothenberg, co-founder of Smooth Media ✅ Yossi J Levi, founder of Car Dealership Guy ✅ Ryan Heafy, co-founder and COO of 6 AM City ✅ Helen Guo, founder of SMB Deal Hunter ✅ Andy Mackensen and Joanna Ericta, founders of The Assist ✅ Brad Wolverton, director of content at HubSpot and The Hustle ✅ Ryan Hashemi, former CSO at Jubilee Media and founder of Snowball ✅ Neville Medhora, founder of CopywritingCourse .com & SwipeFile .com ✅ Brian Morrissey, founder of The Rebooting and former President at Digiday ✅ And more (see website below for all speakers)... Plus, there are more on the way! At this event, we’re bringing the world’s largest newsletter publishers AND newsletter advertisers in one place… …to network, do business, and learn together. This is your opportunity to: ☑️ Meet the biggest newsletter advertisers We designed this event not just for publishers but for marketers who want to sponsor and partner with brands and creators. ☑️ Connect with “who's who" in the industry Network with the newsletters, brands, and creators shaping the future of independent media. ☑️ Learn what’s working right now Discover cutting-edge growth and monetization tactics used by top founders and marketers that you can immediately apply to your business. We designed Newsletter Marketing Summit to be different from other events: ✅ Insightful and original content, not just panels From presentations, workshops, Q&As, and interactive content. The content experience is worth 10X the price of admission. ✅ Dedicated and structured networking The most important part of an event is the connections you make. This is the perfect environment to meet with peers and partners. Our networking time isn’t just the breaks between content. It’s so much more. ✅ Not just a “newsletter” event This event is about building and monetizing owned audiences – not just newsletters. We’ll cover: Digital product marketing, YouTube, podcast, and social growth, email marketing, deliverability, sponsorship sales, B2B media, local media, and so much more. Here are the details: - Feb 27th & 28th, 2025 - Life Austin Event Center, Austin, TX The event is limited to 300 people with 50 VIP tickets. VIP tickets include access to a VIP and speaker dinner, exclusive content, event recordings, and more perks. Tap below to learn more and secure your seat at the lowest price ever!👇
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20 Nov 2024
One thing X is great for: Book reccs. Some of the best books I've read in the last year were recommendations from people I've never met or talked to. Just popped up on my For You and changed the way I see the world forever.
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18 Nov 2024
Want to re-engage your dormant email list with a newsletter? Start small and be ruthless about list hygiene. 1. Start with only recent openers/clickers 2. Add more subscribers in small weekly cohorts 3. Remove anyone who doesn't open 4-5 newsletters
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28 Oct 2024
Agency owners can create 4 weeks of newsletter content in ~15 min. Pick a few questions from last week's client calls, and record yourself answering them naturally – just like you're talking to a friend. Transcribe them, edit them, and schedule. High-value content - FAST.
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Ryan Carr retweeted
ANNOUNCEMENT: Today, we’re launching the GrowLetter Ad Network: A commission-only ad sales service for newsletter publishers AND done-for-you ad buying services for marketers. Over 90% of newsletters lose money because they have unsold ad inventory. Why? Selling ads is hard. Publishers need to: - Reach out to hundreds of prospects monthly. - Grow your list, create content, and do all the other stuff in your business. - Make ad creative, manage campaigns, send IOs, share reports, collect payments, and work to upsell advertisers on bigger packages. Even if you do all that well, 90% of publishers still have unsold ads! And the marketer's job buying newsletter ads isn’t easy either. Newsletter ad buying is broken for marketers. They need to: - Find and vet the best newsletters to buy in. - Negotiate, make creative, optimize landing pages, send payment, and track down ad reports across multiple publishers. - Do this across dozens of newsletters to scale. This can amount to the work of a full time job. Most marketers are just too busy to grow with newsletters effectively! The sad part is... The best marketers know newsletters are a massively underrated growth channel — if used correctly. What makes this even worse is the bad actors out there: - Newsletter publishers that lie about their numbers and grow their email lists with low-quality (or fake) subscribers using shady growth hacks. And, - Marketers who stiff publishers on payment and try to advertise sketchy offers. Of course, there are hundreds of high-quality newsletters and ethical marketers. But buying and selling ads in this environment is hard. We’re changing this. We created the GrowLetter Ad Network to connect vetted publishers and advertisers so both parties can win. Here’s how the GrowLetter Ad Network works (for publishers): - There’s no cost unless we bring you an advertiser you’re not currently working with - We handle billing, ad creative (with your input), tracking links, and reporting - We help advertisers optimize their landing pages and offer - No exclusivity — work with any seller or ad network - We only sell flat fee sponsorships — no CPC - We use your ad pricing and never mark up - Almost no time required from publishers For marketers, GrowLetter makes it easy to: - Buy targeted ads across dozens of high-quality and vetted email newsletters. - Scale your newsletter ads without the hassle of managing campaigns, negotiations, ad creative, reporting, and payments across multiple publishers. We vet every newsletter by analyzing their email data to determine audience quality, ICP match, engagement, and ad results so you can confidently buy ads that drive ROAS. At GrowLetter, we know how to find the best publishers in the world. I’ve worked with the largest and fastest-growing newsletter-first media companies and creators over the past 5 years. (Clients include: The Hustle, 1440, James Clear, Codie Sanchez, Sahil Bloom, Milk Road, Chartr, The Daily Upside, The Rundown, WorkWeek, and many more.) We have more newsletter data than almost anyone. This allows us to help Marketers: - Manage your ENTIRE newsletter advertising campaigns from A to Z – while increasing your ROAS and saving you time. - Buy across many niches, small newsletters with 10k-50k subscribers that most Marketers don’t have time to handle. - Buy exclusive inventory in hard-to-reach newsletters with big, engaged audiences. Sound interesting? Here’s how to get started: - Newsletter operators, apply for us to sell your ads using the link below. - Newsletter advertisers, use that same link to get in touch and talk with me about improving your ROAS and saving time. If you have questions about this, reply below! P.S. We’re specializing in B2B, business, and financial publishers and advertisers right now. If that’s you, get in touch. If not, we can still help! We’ll just have fewer ads for you now. Use the link to get started below.👇
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16 Oct 2024
Watching through Mad Men for the first time (incredible show, btw), and it's interesting how a lot of their work seems to be voice-first (dictate ideas, and someone types it up). About 80% of my workflow is voice-first, and it makes work feel SO much easier.
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16 Oct 2024
If it’s YOUR offer in YOUR newsletter, don’t structure the CTA like you would a sponsor spot. Tie your CTA organically into your content. Have it read naturally with the rest of your newsletter. I guarantee you’ll see better performance.
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15 Oct 2024
Writing a newsletter for your agency? Use your case studies as a starting point. Don’t copy/paste your “Our Work” page. Use them as inspiration to tell stories that communicate specific, tactical lessons. Storytelling is the foundation of pretty much all engaging content.
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14 Oct 2024
If you write a weekly newsletter (and are smart about systems), you already have content for most other channels. Take the long(ish)-form text of the newsletter and: - Format it for LinkedIn - Chop it up for X - Record yourself reading it for short-form video
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Ryan Carr retweeted
We are doing a live podcast meet-up and AMA on Thursday, Sept 26th, at 4:30 pm EST. If you want to join @ryan_boat and me, here's what you need to do: 1) Subscribe to "Matt McGarry" on YouTube 2) Leave a 5-star review for the Newsletter Operator podcast on Apple, Spotify, or another player 3) Email screenshots as proof to matt@newsletteroperator(dot)com Then we'll send you an invite! If you have already done this, you'll get an invite soon.
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13 Aug 2024
ANNOUNCEMENT🚨 Off Menu acquired This Week In Design! We’re getting into the newsletter biz baby Why? Back in 2007 I got my start as a designer in the Flash heyday. I followed every blog and read every magazine I could. It was a content-rich environment for a new kid. Over the years, that all disappeared. A certain internet-holdco bought up all the best sites and sucked out the soul. What was once a beautiful, indie community, became a corporate cog. Fuck that. It’s time things got weird again. I mean, have you seen the shit AI is doing? We need to talk about it. So, that’s where This Week in Design comes in. We’re going to bring the design/creative world the latest news - unfiltered. No spin. Then I’ll talk to a lot of my fancy influencer-type design friends and record raw, unedited conversations that are useful for up and comers. No more boring podcast Q&A. 🥱 We’ll feature great work. Shoutout up and coming designers. Share great resources. All that jazz. I’m also going to talk a few big companies into giving you all discounts and free stuff when I can. Go and subscribe. First new drop comes out this Friday and then every Friday. twid.fyi
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13 Aug 2024
Oh, and we'll build it for you 🤠 tailwindstudio.co (or DM me)

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1 Aug 2024
If you're smart about how you write and optimize your newsletter, you can end up ranking on PAGE ONE of the search results for valuable keywords. I wrote all about our framework for newsletter SEO in a quick little primer I sent out to my email list this morning 👇
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Ryan Carr retweeted
Entrepreneurs: Stop treating your emails as an afterthought. The inbox is the best place on the Internet for reputation, relationships, and revenue. If you send your audience nothing but air, don't be surprised when you get back the same.
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Ryan Carr retweeted
Big mistake: I waited until I had 17,000 followers to start my newsletter. Little did I know, that my newsletter would be main source of income. Here's the deal: Your newsletter is your piggy bank. Why aren't you saving?
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18 Jul 2024
The best advice that I can give to agencies and coaches looking to drive more leads from their newsletters: Be brief, be tactical, and be specific. Give away the "secret sauce" to what you do. It builds trust, shows you know what you're talking about, and books calls.
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