The Flag

What The Flag does

The Flag is a U.S.-based digital media brand and email newsletter founded in 2016 by Brooks in New York City. The company delivers nonpartisan political news coverage and American historical storytelling to politically engaged American readers, structured as a freemium product: a free weekday 'Flag's Five' edition summarizing top political headlines from both left- and right-leaning perspectives, plus a paid premium Sunday edition featuring in-depth American history stories. Content is produced and edited by a small team of approximately five employees.

The technology stack is intentionally lean. Distribution relies on the third-party beehiiv email publishing platform for newsletter delivery and on organic social media channels — Instagram and Facebook — where the brand has accumulated a combined following of over 250,000 users. The company's website (theflag.org) hosts an archive of past editions and subscription sign-up pages but is not described as carrying proprietary technology. There are no AI/ML systems, proprietary algorithms, or developer APIs in evidence; the product is fundamentally human-edited editorial content.

The business model is a recurring subscription model with monthly billing on the premium tier, supplemented by free-tier audience scale used as a funnel and as a platform for any ad or sponsorship activity. Specific pricing is not publicly disclosed. As of October 2025, the company announced an indefinite pause to the newsletter and a suspension of premium subscriber billing, with founder Brooks redirecting focus and resources toward a separate newsletter brand, The Street Sheet, which he also owns. The Flag itself has no disclosed external funding, no institutional investors, no acquisitions, and no patents or trademarks on record.

Name

The Flag

Legal name

THE FLAG

Website

https://theflag.org

Company type

Private

Founded year

2016

Operating status

Operating

Headcount range

1–10 employees

Short description

The Flag is a U.S.-based email newsletter and social media media brand founded in 2016 by Brooks, delivering nonpartisan political news summaries and American historical storytelling to American readers via beehiiv and Instagram/Facebook. The newsletter is currently paused as founder focus shifts to sister brand The Street Sheet.

Ownership category

akta.pro rank

Product category

Political News Newsletter

NAICS

Periodical Publishers (513120), Periodical Publishers (51312)

SIC

Periodicals: Publishing Or Publishing & Printing (2721)

akta.pro primary industry

Newsletters & Email-Based News Publishers (B2B/B2C) (MPAJADAJ)

akta.pro secondary industry

News, Politics & Current Affairs Magazines (MPAJAEAO)

Keywords

• Political news newsletter
• Email newsletter publishing
• Nonpartisan news coverage
• American history content
• News media subscription

GTM type

B2C

Offering type

Digital Commerce or Content

Cost components

Personnel, Operations, Marketing or Sales, Technology or R&D

Revenue model

1. Premium Newsletter Subscription: Paid subscription model offering access to Sunday premium historical content editions and ad-free reading experience. Free tier provides weekday 'Flag's Five' political news summaries. Premium members have payments paused during current operational pause.

Pricing tiers

Go-to-market motion1 record

Distribution channels2 records

Marketing channels4 records

Core offering

The Flag publishes a nonpartisan U.S. political news newsletter delivered by email, offering free Monday-Friday "The Flag's Five" editions that summarize five top political headlines with perspectives from both left and right. A premium Sunday subscription tier adds ad-free American historical stories, subscriber-only content, and commenting privileges. The newsletter is distributed via the beehiiv email platform and promoted through Instagram and Facebook social channels with a combined 250,000+ follower audience.

Product overview

The Flag is a single newsletter product offered in two tiers: a free tier providing Monday-Friday political news coverage through 'The Flag's Five' segments, and a premium subscription tier that includes an ad-free Sunday newsletter featuring American historical stories. The product is delivered via email and social media platforms, with premium subscribers gaining access to subscriber-only content and commenting abilities.

Differentiator

Problem solved

Functional benefit

Products and services

• The Flag Newsletter A daily nonpartisan U.S. political news newsletter delivered via email, offering free Monday-Friday editions under the "The Flag's Five" format covering five top political headlines with perspectives from both left and right, plus a premium paid Sunday edition featuring ad-free American historical stories and subscriber-only content. Targeted at individual politically engaged American readers and American history enthusiasts.

Segments1 record

Ideal customer profiles1 record

Technology focussed No

API detail

Has API

No

API docs

API detail

Core technology

AI maturity

App detail

Partnerships

One partnership is on record.

• The Street SheetcoreOthersThe Street Sheet is another newsletter brand owned by the same founder (Brooks). The Flag is currently pausing operations to focus resources on The Street Sheet, which is described as driving better returns. This is an internal brand strategy decision rather than an external partnership.

Scale indicators2 records

Recent moves5 records

Expansion highlights4 records

Direct peers

• Punchbowl News: A subscription political newsletter covering Congress and Washington politics. Comparable in target audience (politically engaged readers), newsletter-first distribution, and paid subscription model.
• The Street Sheet: The founder Brooks's other newsletter brand, which is currently being prioritized over The Flag. Operates the same newsletter format on beehiiv with a similar target audience of politically engaged American readers.
• Ground News: A news comparison platform and newsletter that explicitly aims to help readers identify political bias in coverage. Closely comparable in nonpartisan value proposition and politically engaged reader segment.
• The Dispatch: A digital political media company offering newsletters covering politics and policy with explicit both-sides framing. Closely comparable in nonpartisan positioning, newsletter-centric distribution, and politically engaged readership.
• Morning Brew: A leading daily newsletter covering business and politics for a young professional audience. Closely comparable in format (daily email newsletter), freemium model, and politically engaged readership.
• The Daily Wire: A conservative-leaning political media company with newsletter and podcast products targeting politically engaged Americans. Comparable in subscription-based political news model and target audience, though with a different editorial stance.

Others

• beehiiv: The newsletter publishing platform that hosts The Flag's email distribution. Comparable as an enabling infrastructure provider rather than direct competitor, but relevant given The Flag's dependence on this platform for distribution.

Emerging players

• Semafor: A global news startup launching in 2022 with a newsletter-led format covering politics, business, and technology. Comparable in newsletter-first distribution model and focus on balanced news coverage for engaged readers.

Broad incumbents

• Axios: Major digital news outlet known for its 'Smart Brevity' newsletter format covering politics and policy. Directly comparable in nonpartisan political coverage with established newsletter products like Axios AM and Axios PM.
• Politico: An established political news outlet with newsletter products (Playbook, Politico Pulse) targeting Washington insiders and politically engaged readers. Comparable in coverage area and audience, though much larger in scale.

Market position

Strengths5 records

Weaknesses5 records

Competitive moat2 records

Key risks6 records

Key highlights5 records

Customer concentration

• Facebookfacebook.com/tagtheflag
• Instagraminstagram.com/tagtheflag
• LinkedInlinkedin.com/company/tag-the-flag

Revenue estimate

Valuation estimate

Number of profiles

Profiles1 record

Funding overview

Funding rounds

Investors

Funding detail is available on the Subscription and Enterprise plan.Contact sales →

M&A

Investments

M&A and investment is available on the Subscription and Enterprise plan.Contact sales →

Frequently asked questions about The Flag