Puck Pays $16M for Air Mail // Rise of Journalist-led Newsletters
November 7, 2025 by Chris Erwin
RockWater Roundup
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Today we discuss Puck’s acquisition of Air Mail, a digital media and newsletter company covering culture, travel, fashion, politics, and lifestyle. We analyze deal details, strategic rationale, journalist-led media brands and how they’re financed, balancing talent empowerment AND parent co performance, and news media disruption.
Let’s break it down…
–SELLER: Air Mail–
Overview
- Digital media and newsletter company covering culture, travel, fashion, politics, and lifestyle
- Known for premium editorial tone, high-quality photography, investigative journalism, and satirical commentary
- Targets high-income professionals, creatives, and international readers
- HQ’d in NY with contributors and editorial staff across US and Europe
- Founded in 2019 by Graydon Carter and Alessandra Stanley
- Raised ~$32M from Standard Investments, TPG, dmg ventures, and RedBird Capital Partners
- 80+ associated members on LinkedIn
Founding Story
- Before Air Mail, Graydon Carter served as Editor-in-Chief of Vanity Fair and Alessandra Stanley as New York Times’s Moscow and Rome bureau chief
- After leaving Vanity Fair, Carter believed traditional magazines had become “too slow, too corporate, too disconnected from affluent, globally minded readers.”
- Carter then raised funds to launch Air Mail as a digital weekend magazine delivered via email
- The first issue was published on July 2019 featuring international reporting, crime stories, arts coverage, travel, fashion, and political satire
Company Highlights
- Known contributors include Ashley Baker, Michael Hainey, and William D. Cohan
- Estimated 500K total subscribers
- Estimated $15M+ in annual revenue (March 2023)
- E-commerce is ~15-20% of total revenue
- In 2023, launched Italian and French editions
- Air Mail’s Morning Meeting podcast: Weekly show covering news, culture, and notable stories with 260+ episodes, ranks in the Top 1% of podcasts
Business Lines / Service Offerings
- Overview…
- Digital media and newsletter publisher with revenue from subscriptions, luxury advertising, affiliate deals, e-commerce (Air Supply), events, and travel partnerships
- Air Mail Digital Newsletter…
- Weekly email magazine with premium editorial voice
- Air Mail Travel…
- Curated city guides, boutique hotel recommendations, and travel concierge partnerships
- Podcasts & Audio…
- Morning Meeting podcast: weekly news and culture discussion hosted by Graydon Carter and Ashley Baker
- Events & Member Experiences…
- Invite-only salons, book launches, and gatherings in NYC, London, and Paris to deepen loyalty and brand community
Capital Markets History
- Oct ‘25 Acquired by Puck
- Dec ‘21 Raised $17M in Series B funding from TPG, Standard Investments, and Redbird Capital Partners
- Jan ‘19 Raised $15M in Series A funding from TPG and dmg ventures
–BUYER: Puck–
Overview
- Subscription-based digital media company covering the power dynamics of Wall Street, Hollywood, Silicon Valley, Washington, fashion, and culture
- Serves executives and high profile audiences seeking “news behind the news”
- Puck’s model positions journalists as the face of distinct newsletter “franchises,” with readers drawn to the personalities over the parent brand
- Founded in 2021 by Jon Kelly, alongside co-founders John Thornton, Julia Ioffe, and Peter Hamby
- In Jan 2024, Sarah Personette announced as CEO, took over role from Kelly
- HQ’d in NY, with contributors and editorial staff in LA, DC, London
- Raised ~$20M from British Business Investments, J Rothschild Capital Management, Forty North Media, Standard Investments, and TPG
- 70+ associated members on LinkedIn
Founding Story
- Founded in April 2021 by former Vanity Fair and Hollywood Reporter editor Jon Kelly, a former mentee of Air Mail founder Graydon Carter
- Founders believed traditional media undervalued star journalists, so built model where writers are treated as equity partners and creators
- Business launched in September 2021 with four founding journalists and its first verticals: Wall Street, Hollywood, Washington, and Silicon Valley
Company Highlights
- By November 2022, Puck had nearly 200k+ email subscribers, with 20k+ paid
- Puck’s average newsletter open rate is ~70%, significantly higher than typical industry newsletter open rates of ~30%
- Unique ownership model: writers receive equity stakes + bonuses based on new paid subscribers and subscriber retention
Business Lines / Service Offerings
- Paid Digital Subscriptions & Newsletters…
- Core revenue driver, includes verticals like “What I’m Hearing…” (Hollywood) and “Dry Powder” (finance)
- Podcasts & Shows…
- Flagships include The Powers That Be and The Town — news, media, dealmaking, and politics discussions led by Puck journalists
- Sponsorship & Branded Content…
- Brand partnerships across sectors like financial services, entertainment, and luxury goods.
- Examples include cultural programming (e.g., the Tom Wolfe Literary Prize), live event series, and native newsletter placements
Capital Markets History
- Oct ‘25 Acquired Air Mail for $16M for cash & stock
- Apr ‘24 Acquired Artelligence, a newsletter publishing company, from Substack
- Aug ‘23 Raised $13M in Series B funding from British Business Investments and J Rothschild Capital Management
- Mar ‘21 Raised $7M in Series A funding from Forty North Media, Standard Investments, and TPG
–DEAL DETAILS–
Overview
- Announced October 30, 2025
- Estimated transaction value: $16M incl mix of cash and stock
- Represents a loss for investors, who get back ~50 cents on the dollar, since $32M was initially raised.
Strategic Rationale
- Expands Puck’s coverage into lifestyle and culture, adding to its existing strengths in politics, business, and entertainment
- Brings Air Mail’s high-income, global subscribers into Puck’s growing paid membership base
- Combines two subscription-first media brands that prioritize loyal, high-value audiences over mass traffic
- Creates new opportunities for cross-promotion, bundled subscriptions, and premium advertiser partnerships
- With TPG as a major investor in both companies, the deal consolidates its portfolio of newsletter-first media assets, positioning Air Mail as a bolt on to Puck
- “Air Mail was always envisioned as the weekend edition to a digital daily news engine, and in Puck we have the perfect alignment,” said Graydon Carter
Post-Deal Operations
- Julia Vitale becomes editor-in-chief of Air Mail
- Graydon Carter, founder of Air Mail to step back as editor and transition to consultant role
- Air Mail stays independent in voice but becomes Puck’s “weekend edition.”
- Bundled subscriptions + shared login infrastructure to come in 2026
- Joint podcasts, travel guides, and editorial collaborations in development
- Sales, marketing, and membership ops to consolidate under Puck
- Editorial teams remain separate but aligned on strategy
- Air Mail migrates onto Puck’s subscription and analytics platform
–WHAT ELSE I FIND INTERESTING–
- Journalist-led media brands are turning independence into sustainable subscription and ad-supported media businesses.
- Puck and Air Mail were both started by former magazine editors who left to build paid newsletters for loyal, upscale audiences.
- The Free Press, which recently sold for $150M to Paramount, followed a similar path (our deal analysis). Founder Bari Weiss left the New York Times in 2020 citing workplace hostility and lack of ideological diversity, and then launched TFP the same year.
- And then just last week, the launch of Scalable Pod was announced, which followed the departure of Kaya Yurieff from The Information and Jasmine Enberg from EMARKETER. Both Kaya and Jasmine built large personal brand awareness and followings by leveraging their employer’s platforms, and then realized they could build a modern news media brand that they had owned (and did so via a JV with Whalar Group / The Lighthouse).
- This is all part of a larger shake-up in traditional news media; see analysis at bottom for a more detailed analysis and POV here by our team. There’s also other helpful context here from Natalie Jarvey’s Like & Subscribe newsletter, which is one of a few newsletters under parent co Ankler Media.
- This all raises a question about how these modern news publications are financing their media newco’s…
- What is market precedent for financing a modern, journalist-led, news media co launch?
- Here are some capital markets questions our team is asking based on the Air Mail / Puck deal…
- What are the pros / cons of self-funding? Does it make sense to raise money? If so, at what point in the lifecycle of the newco launch? Can only mass-appeal journalists with big personal brands raise funding? Who are the types of investors funding these businesses?
- Thanks to the trend of decreasing resource and cost requirements for getting a newco off the ground, there are many tools for creators and journalists that make it easy to build a D2C media business.
- For example, Substack is a turnkey newsletter platform that takes 10% of subscription revenue, and manages all the infrastructure including payments, email templates and delivery, and analytics.
- There are also incubators and accelerators for news media creators and journalists building their own D2C brands, including those by newsletter platforms Substack and Beehiiv, amongst others, which offer seed capital, product guidance, and distribution boosts in exchange for equity or revenue share.
- This is such a win for the journalist and news media creator class.
- But when the aspirations for a modern news media outfit are a bit more grandiose, we’re seeing significant money flow into the space, as well as key strategic partnerships to accelerate growth.
- Let’s dive into a few examples…
- Highlights of capital markets activity for journalist-led media brands.
- While not an exhaustive list, a few deals stand out…
- Bari Weiss and The Free Press – raised $15M in Series A funding in Sep 2024 and $1-5M seed funding in 2022, two years after launch. Main seed investors were angels including Marc Andreesen, David Sacks, former Starbucks CEO Howard Schultz, and others. Rumors were $15M of revenue, unprofitable, sold for $150M to Paramount (our deal analysis).
- Air Mail – raised $17M in Series B funding in Dec 2021 and $15M in Series A funding in Jan 2019, the founding year. Main investors were TPG (private equity), Standard Investments (diversified industrials / family office), dmg ventures (vc fund), and Redbird Capital Partners (private equity).
- Puck – raised $13M in Series B funding in Aug 2023 and $7M in Series A funding in Mar 2021, the founding year. Main investors were British Business Investments (private investments), J Rothschild Capital Management (family office), Forty North Media (ad agency), Standard Investments and TPG.
- Ankler Media – in 2022 raised $1.5M seed from Y Combinator and Dick Parsons’ Imagination Capital, Goodwater Capital, Pioneer Fund, FilKor Capital, and individual investors. Focused on paid subscriptions, got a $20M valuation. Founded by former The Hollywood Reporter editor Janice Min and Hollywood reporting veteran Richard Rushfield.
- Scalable Pod – Launched in 2025, did 50-50 joint venture with Whalar’s Group’s The Lighthouse, which is providing capital (unknown amount, perhaps covering salaries and startup costs) and operational support including podcast studio space, production, branding and marketing, and advertiser sales. Cofounders maintain editorial control. Also joined Beehiiv accelerator, gets suite of resource to grow newsletter in exchange for commitment to Beehiiv platform.
- Tucker Carlson & Megn Kelly – hired Red Seat Ventures to support content production, ad sales, and other admin / ops in building and running D2C media businesses after departing from Fox (but have now returned, read our deal analysis). Due to their national celebrity profiles and previous financial success, perhaps they self-funded launch. TBD if there were any minimum guarantees from RSV, or perhaps there were advertiser pre-sales.
- So what are my takeaways from all of this?…
- Modern news media companies are attracting investment from a diverse set of investors.
- Investor types are broad, ranging from angels and VC to family offices and private equity.
- Funding sequencing follows that of typical startups, where there’s a seed round to support launch, then larger growth rounds via Series A and B that follow over the next two to three years.
- Subscription models by high-profile personalities or creative execs (e.g. print media editors or TV broadcasters) with an existing audience install base / national recognition, professional ops, and a track record of recurring reader revenues, are attracting the most funding.
- Large national celebrities, who have significant financial resources, still seek professional services to scale up.
- The investment thesis may not always be about financial ROI. Investors and wealthy individuals have a longstanding track record of investing in media, where the end goal is cultural and political influence (some similar investment themes in our deal analysis of Highmount investing in Dude Perfect). In this deal specifically, Air Mail raised about $32M and is getting back $16M in cash and stock, so they’re returning about 50 cents on the dollar. Not a great outcome…
- Overall, these are just a few datapoints, so I don’t want to extrapolate any definitive financing models from a limited data set. But, I do believe these reference points do signal in broad strokes how these modern news media co’s are being built and financed.
- Puck’s biz model incents writers to grow audiences = aligns with creator economy DIY values.
- Puck ties writer pay to subscriber growth and retention, and gives their writers equity and incentives for audience expansion.
- This is a savvy move. Writers are the company’s most valuable asset, and could walk out the door if not properly motivated. Just see the journalist defection list throughout today’s newsletter!
- But, going it alone is hard. Just ask the long tail of the creator economy where most are not even earning a living wage. Therefore, Puck is striving to find the balance of both making journalists feel that they have ownership and independence in what they’re building, but also feel like they’re part of something bigger, and with professional support and community to achieve great success than if they were to do it alone.
- I like this quote from Sarah Personette, Puck CEO, from a Digiday podcast earlier this year: “You almost have sub-brands under Puck that are franchises anchored by core talent versus in probably that first two years, it was a newsletter anchored by core talent.”
- New business models that empower and retain high-profile talent within a larger corporate organization, is something that many companies within the creator space are working to figure out. A similar dynamic is playing out amongst talent representation firms, like management companies and agencies, and particularly those repping digital-native talent.
- Over the past 5 to 10 years, the most successful influencer managers departed the big name firms (or refused to even join) and instead bootstrapped and built their own successful representation companies. Many generated outsized revenues and realized successful exits, leading to personal wealth faster than could have been realized if they went and worked for a traditional rep firm. Our RockWater team is grateful to have advised on some of these deals, like Dan Levitt’s Long Haul Management selling to Wasserman (our deal analysis), Chas Lacaillade’s Bottle Rocket Management selling to Night (our deal analysis), and Click Management selling to Gamesquare for $8.5M plus earnout (our deal analysis).
- And today, the competition to retain star talent managers is FIERCE. As a result, there are new modern talent firms being built that strike to find the balance of (1) motivating up-and-coming talent reps to join a larger talent company platform, and maintain the ability to earn the majority of upside in what they build, (2) while concurrently driving parent co performance and building enterprise value for owners. These newcos are redefining the modern talent rep business model (NOTE: one of them is our client, is growing very quickly and is highly profitable, and now seeks a larger strategic partner to support larger growth ambitions. DM me if you want to learn more!)
- Alright, that’s enough writing for today’s newsletter. We’ll close with some former analysis that provides some more context for today’s break down…
- Traditional news media is broken. New digital-native journalists are on the rise, creating a major opportunity in the modern media landscape.
- NOTE: We wrote about this in our analysis of Paramount buying The Free Press, and also in our analysis of Entertainment360 buying OManagement, a boutique news and personality talent management firm (our deal analysis). The breakdown is very relevant to today’s deal, so copying here for reference..
- “More and more journalists are leaving TV networks, publishers, and newspapers to build their own D2C media businesses. They’re starting their own newsletters on Substack, YouTube channels, TikTok feeds, and podcasts. In turn, they’re becoming their own brands as traditional media fragments.
- There are many examples here – Ben Smith left BuzzFeed News and co-founded Semafor, a global digital news platform; Matt Yglesias left Vox to start “Slow Boring” newsletter; Casey Newton left the Verge to start “Platformer” newsletter; Taylor Lorenz left the Washington Post to launch independent tech / culture reporting on Substack and TikTok…the list goes on. This is becoming big business, and traditional media is starting to re-think their news and talent business models – specifically, the departure of top political and news personalities from Fox (e.g. Tucker Carlson, Megyn Kelly), was one of the key drivers behind the landmark Fox’s acquisition of Red Seat Ventures in Jan 2025 (our deal analysis).
- During COVID, John Krasinski’s Some Good News on YouTube showed how news fans seek alternative news media formats to traditional news fare. Today, we’re increasingly seeing audiences, across all ages and not just youths, migrate to modern social and podcast-native alternative news formats. I think of All In Podcast, where 4 “besties” from Silicon Valley cover a range of topics from finance to politics to luxury lifestyle (and recently launched a premium Tequila brand), to YouTuber Tim Pool’s livestreaming news media network, and on-the-ground real-time war coverage on TikTok in Ukraine.
- Our takeaway from all this is that there’s a massive opportunity in the evolving news media ecosystem. From building modern news networks (further building on top of early social news networks like The Young Turks and NowThis), to those companies building support services for these new digital and D2C journalists, like ad sales and talent management.
- Case in point, we’re hearing a lot more from talent rep insiders that they’re focusing on signing fast-growing talent news personalities. Some of these firms have already built meaningful news talent divisions (keeping them anonymous per their request). We’re therefore not surprised by this OManagement deal, and we expect to start seeing a lot more activity in this space. Personally, I’d love to see a modern news media and talent rep outfit represent personalities on both sides of the political aisle here in the US – I haven’t seen anyone crack that code yet, but there’d be fun innovation in content formats, would set a great new precedent for productive political discourse and talent collaborations, and would probably generate great business ROI 😉”
- UPDATE as of 9.11.25 – With Fox buying RSV in January, and assuming Paramount closes on the acquisition of The Free Press, makes me wonder when other traditional news media businesses are going to start making creator-based investments to power their modern news media strategies. The RSV deal was a different flavor (D2C and agency services for various of conservative-leaning talent), and the Free Press Deal is an acquisition of a media company (incl their writer and contributor network) coupled with a large employment deal for a top talent in Bari Weiss.
- Which of these is the best strategy? I lean towards the RSV model – a scalable agency services platform to add many more talent and media channels, with lower revenue concentration and talent flight risk, and not as reliant on a singular 3rd party platform like the TFP has with Substack.
- Further, what might the next flavor of a modern news media deal look like?
- These are questions we should all be asking.
I’m the founder of RockWater Industries. We do M&A and strategy advisory for creator economy and social / audio agencies. From buy / sell-side M&A and fundraising, to consumer research and go-to-market planning.
DM me on LinkedIn or email me chris @ wearerockwater dot com
