Top 50 newsletter lessons of 2025

TheSkimm sold this year. They inspired dozens of newsletters to start (MBrew, Hustle, etc.). Those newsletters made more money because they seed-strapped instead of raising huge VC rounds. Lesson in there. 

AI inbox summaries are coming for curation newsletters. You must write original content people cannot google (Status, A Media Operator, etc.) or be seen as a taste-maker (Shaan Puri, Morning Brew, etc.). Going multi-channel (podcast, organic social, etc.) helps deepen your relationship with the reader so you can achieve ‘taste-maker’ status.

80% of the newsletters that hit $1M+ per year help people with their niche hobbies, jobs/career, investments, or personal transformations.

Everyone thinks I’m anti-B2C newsletters. Not true! My advice just to not start a consumer newsletter unless you have a big (25,000-50,000+) social following or have the patience pursue a single niche for 2-3+ years.

Most ad-monetized newsletters make 20-40 cents per reader per month. That’s $2.40-$4.80 per year per reader.

The gold-standard newsletter engagement metrics are 40%+ open rates, 3-5%+ click-through-rates, and 0.5%+ ad CTRs.

Local newsletters are fantastic white belt $50k-150k/year businesses. If I had time I would start a local newsletter for founders in NYC.

If you’re a B2B founder, it is critical to understand the easiest way to make a million dollars with a newsletter is to nurture people for your B2B SaaS or service offer. Or start an agency/consultancy/coaching biz and newsletter at the same time. 

Don’t start a daily newsletter alone. That’s like opening a one-man diner. 99% your time is going to be spent making omelets, 1% of your time is going to be focused on getting customers in the door. 

Triple your welcome email CTR by telling new readers their subscription isn’t confirmed until they click a button. Tom Alder does this, 40% CTR. 

Do Tom’s method, do NOT actually do real double opt in. Oh my god. Please. 

Want to generate endless content ideas? Record your calls weekly. Upload to ChatGPT. Ask for every challenge / question that came up. Go to dinner alone on Sunday night, review, and write down 10 ideas.

You have a $70,000/yr junior copywriter in your pocket for $20/month. Upload your best writing (or your favorite writing) to Claude. Download the app. Voice note what you want to write about. Ask it to ask you clarifying questions. Answer them. Now have it outline a newsletter. Give it edits. Now have it draft. Now edit the draft by hand. All done.

I asked Tim Huelskamp (Co-founder and CEO, 1440) to share all of his year-by-year numbers and tactics with me. This is the best video you will watch all year if you’re trying to build a newsletter like a business on day 1.

Only use broad targeting on your Meta ads. We have gone head-to-head with multiple agencies this year using interest-based targeting. We have won 6 out of 7 of those accounts.

Lead magnets are the #1 way to grow your newsletter using organic social. The 2nd best strategy is not even close.

Sponsor walls / co-branded lead magnets. For 18 months I’ve been telling you The Assist is KILLING it with their post-sign up sponsor wall, breaking even on readers in 7 days. Only Techpresso and The Deep View have made their own during that time period. Why???

Webinars are still the best way to sell $1.5-$10k products. If your product is $2,000 or less, send people to a sales page. $2k-$5k is no-mans land. Above $5k, send people to a sales call.

Paid challenge ($20-$97) funnels are hot right now. Premium Ghostwriting Academy did one in November, Write Your Way to Wealth, 3.5x ROAS on $100k of ad spend.

The best performing sponsor formats are lead magnets and webinars. High LTV SaaS, financial offers, and B2B services are the best performing sponsors. 

If you do a lead magnet or webinar, host the sign up page for your sponsor. Keeping it on your URL and co-branding it with your brand SIGNIFICANTLY improves opt-in rate 

The easiest way to 2x your sponsorship revenue is to sell deep dives for 3-6x your primary. The Rundown ($10M+) and The Deep View (500k+ readers) both had big revenue gains this year from sponsored deep dives. 

Easiest way to add revenue to a $1-5M broad newsletter is to spin up ‘child’ newsletters in sub-niches or topics - Morning Brew, 1440, TLDR, The Rundown, Secret CFO are all doing this very successfully.

Get 3 subscribers for the price of 1 by recommending your child newsletters in your sign-up flow (go through The Deep View’s funnel here). Industry Dive, 1440, Insight Links, The Rundown also all do this well.

The Flyover used capital / email lists from a political sponsor business to bootstrap a 1440 competitor to $400k/month and then raised millions of dollars from its readers. People can be critical of the $35M valuation, but this was objectively one of the most clever moves of the year.

Sell to rich people. SMB Deal Hunter joined the October cohort of my newsletter accelerator. They help ex-consultants / tech people buy businesses and are the best business I met this year. 

Know your numbers. Call book rate, close rate, ARPU, LTV, subscription CVR, etc. How do you run a business and not know your numbers?

Financial offers make the best newsletters / crush email marketing. Everyone should study Marketbeat’s ($45M+) emails. Go watch a VSL from Brownstone Research and write it by hand. Masterclasses in direct response copywriting. 

If your LTV:CAC is great, raise debt. One of the smartest things 1440 did (and they’ve done a LOT of smart things) is use a debt vehicle to fund paid marketing.

Many people have told me behind closed doors they can’t believe 1440’s open rate / click through rate numbers. 1440 is cohorting and measuring LTV, cleaning their list like crazy, buying from high-quality newsletter sources, optimizing Meta spend toward the ads that drive the highest open rate and CTR. The other people? They just want a <$2 CPL. Lesson in there.

Newsletter ad buys produce the most incredible readers. I’ve buried this far in the list. If you’ve read this far, I like you, and so I want to let you in on this little secret.

Niche B2B and high ticket offers MUST survey readers and only pass back Meta conversion events for qualified readers. 

Ugly ads perform. Even if you hate them, 1440, our clients, Morning Brew, and all of the top spenders are winning with formats like low-fi UGC and text-over-video.

Jesse Pujji’s mutual intro playbook is the highest leverage way to close your first $500k in sales.

Your baseline weekly sponsor outreach KPIs should be 50 companies, 4 stakeholders each, 10 responses, 3 meetings, 1-2 new logos closed.

Alex Hormozi made $100M in 48H with a webinar this year. It is a masterclass in sales, objection handling, stacking bonuses, etc. I did a 5-minute breakdown of all 1,700 slides here.

If you are scaling with paid ads and are a serious newsletter, you’ll measure ad-level open rate / CTR and use it to evaluate creative.

If you sell products, send 2x as many sales emails as you think you need to. A reader is worth $0 to you until they purchase something.

Open & close cart sales (limited time, limited seats) always outperform and sending 2-3 last-call emails will add 20-30% to your sales in the final 12 hours

Web-first publishers are really struggling to build newsletters. Conflicting sales team incentives, content optimized to only send traffic to the site, no support on growth or clear owners. It’s rough.

Paid ads for subscription newsletters is hard. B2B paid subscription I am bullish on - the average order value ($200-400) supports paid. It’s very hard to make paid work with <$100 pricing.

You must collect 1P data in your sign-up flow. Use it for sponsors and if you sell something, use it to personalize your sales emails and pages.

Personalization in sales (20-40% CVR boost) is as simple as using 1-2 survey responses to change email subject lines, opening sentences, and sales page headlines.

Ad networks are making it harder to sell your own sponsorships. This helps the beginner, hurts the intermediate, and raises the bar for the expert.

The best sponsor-monetized newsletters will act like marketing partners, not marketing channels. The “end-game” of products/services looks like Industry Dive’s media kit.

Pivot ideas, try not to pivot niches - let your status in a niche compound. My buddy Oliver started an Ecomm brand Tabs when he was 19, bootstrapped it to $10M, sold it for millions when he was 22. Now he runs a SaaS for Ecomm founders. $1M in Y1, will end December at $220k MRR. 

Take a simple idea very seriously. I hired Jason Levin to do street interview ads for The Neuron in 2024. He did them. Got bored. Moved onto a SaaS for memes. 12 months later my buddy Josh started a street interview agency. He did $306,000 last month. He’s 23. 

The most critical first step to starting a company is not meeting a co-founder or having an idea. It’s believing that it is possible. You must indoctrinate yourself with content that makes you so optimistic that you become delusional. Hormozi, How I Built This, Goggins, whatever. Pick your preacher. 

Be playful. When I worked at BCG, all the associates (myself included) were so formal. How is someone going to trust you if you’re always circling back, double clicking, and synergy-ing shit? It’s so much easier to do deals and have people rooting for you when you operate from a place of play. Plus, you’ll have more fun in the process.

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