21hats
21 Hats is a bootstrapped media and community platform founded by journalist Loren Feldman in 2019, producing a daily newsletter, weekly podcast, monthly mastermind sessions, and in-person events for small business owners and entrepreneurs seeking peer-driven business advice.
- Company typePrivate
- Founded2019
- Headquarters—
- Headcount1–10
- GTM typeB2C
- OfferingDigital Commerce or Content
What 21hats does
21 Hats is a privately held, bootstrapped media and community platform founded in 2019 by journalist Loren Feldman to serve small business owners and entrepreneurs. It operates four interconnected products: the 21 Hats Morning Report (a daily email newsletter distributed via Substack), the 21 Hats Podcast (a weekly podcast on Apple Podcasts, Spotify, Google Podcasts, and Stitcher with over 305 episodes), the Founding Members Program (monthly Zoom mastermind sessions), and 21 Hats Live (limited-capacity in-person events for 20 business owners). In late 2025 the company also launched the Simple Numbers 100, an index tracking performance of 100 entrepreneurial businesses, developed with CRI Simple Numbers partner Brandon Gray.
The platform's core technology is content distribution infrastructure rather than proprietary software: a WordPress website, a Substack-hosted newsletter, and standard podcast hosting via spreaker.com. There are no AI/ML products, APIs, or proprietary data products. The company's value proposition is editorial — featuring real business owners having candid conversations about wins, losses, and operational challenges rather than offering prescriptive advice.
21 Hats generates revenue through three streams: recurring subscriptions for the Morning Report newsletter and Founding Members mastermind sessions, fees for 21 Hats Live in-person events, and podcast advertising (e.g., Grasshopper Bank sponsorship). The podcast, blog, and selected conversations are free; pricing for the subscription and mastermind tiers is not publicly disclosed. The company has 1-10 employees, is based in the US with team members distributed across multiple states and the Philippines, and serves audiences primarily in the US, UK, and Philippines. Distribution is global via digital channels, with regional in-person events. The company has no external institutional funding and operates as an independent editorial property.
21hats firmographics
Firmographics- Name
- 21hats
- Legal name
- 21 Hats
- Website
- https://21hats.com
- Company type
- Private
- Founded year
- 2019
- Operating status
- Operating
- Headcount range
- 1–10 employees
- Short description
- 21 Hats is a bootstrapped media and community platform founded by journalist Loren Feldman in 2019, producing a daily newsletter, weekly podcast, monthly mastermind sessions, and in-person events for small business owners and entrepreneurs seeking peer-driven business advice.
- Ownership category
- akta.pro rank
21hats business model
Business model- GTM type
- B2C
- Offering type
- Digital Commerce or Content
- Cost components
- Personnel, Operations, Marketing or Sales, Technology or R&D
Revenue model
- Newsletter Subscription: The company publishes a daily email newsletter (the Morning Report) that Inc. magazine called 'the best newsletter for business owners.' Subscribers pay to access the newsletter content.
- Events and Mastermind Sessions: 21 Hats hosts in-person events (21 Hats Live gatherings limited to 20 business owners) and monthly mastermind sessions for Founding Members, generating revenue through event fees.
- Podcast Sponsorships: The podcast episodes feature sponsors such as Grasshopper Bank, generating advertising revenue.
Pricing tiers
| Model | Billing | Price |
|---|---|---|
| Freemium | Monthly | Free content — podcast, blog, and selected conversations are available at no cost |
Go-to-market motion1 record
Distribution channels4 records
Marketing channels7 records
21hats product offering
Product offeringCore offering
21 Hats produces media and events offering business advice, entrepreneurial insights, and peer conversations for business owners. The company operates a daily email newsletter (the Morning Report), a weekly podcast, monthly mastermind sessions for Founding Members, and limited-capacity in-person events (21 Hats Live). The platform features real business owners speaking candidly about their experiences rather than offering prescriptive how-to advice.
Product overview
21 Hats is a media and community platform for business owners offering four interconnected products: the 21 Hats Morning Report (daily email newsletter), the 21 Hats Podcast (weekly podcast featuring candid owner conversations), the Founding Members Program (monthly mastermind sessions via Zoom), and 21 Hats Live (in-person events). The platform focuses on delivering practical entrepreneurial insights through peer-to-peer learning rather than prescriptive advice, featuring real business owners sharing wins, losses, and lessons learned.
Differentiator
Problem solved
Functional benefit
Brands
- 21 Hats Morning Report: Daily email newsletter for business owners, described by Inc. magazine as 'the best newsletter for business owners'
- 21 Hats Podcast
- 21 Hats Conversations
- Simple Numbers 100
Products and services
- 21 Hats Morning Report A daily email newsletter that combines original articles, interviews, and analyses with the most important news of the day for business owners. Distributed via Substack and delivered to subscribers' inboxes every morning.
- 21 Hats Podcast A weekly podcast moderating conversations among a group of business owners who discuss what's working, what's not, and how they see the challenges all owners confront. Episodes feature three owners discussing real business situations, decisions, and challenges. Available on Apple Podcasts, Spotify, Google Podcasts, and Stitcher.
- Founding Members Program A monthly mastermind session for Founding Members that meets via Zoom, where members compare notes, make connections, and discuss issues relevant to business owners.
- 21 Hats Live In-person events for business owners that include dinners, networking opportunities, podcast recordings, facility tours, and interactions with regular podcast participants. Limited to small groups in various cities.
Companies that use 21hats
Customer profileSegments1 record
Ideal customer profiles1 record
21hats technology and API
TechnologyTechnology focussed No
API detail
- Has API
- No
- API docs
- API detail
Core technology
AI maturity
App detail
21hats partnerships and signals
Strategic signalScale indicators1 record
Recent moves6 records
Expansion highlights6 records
21hats competitors and assessment
Company assessmentMarket position
Weaknesses4 records
Competitive moat4 records
Customer concentration
21hats social profiles
Digital presence21hats financial estimates
Financial estimateRevenue estimate
Valuation estimate
21hats leadership team
Management profileNumber of profiles
Profiles1 record
21hats funding detail
Funding detailFunding overview
Funding rounds
Investors
Funding detail is available on the Subscription and Enterprise plan.Contact sales →
21hats M&A and investment
M&A and investmentM&A
Investments
M&A and investment is available on the Subscription and Enterprise plan.Contact sales →
Frequently asked questions about 21hats
What does 21hats do?
21 Hats produces media and events offering business advice, entrepreneurial insights, and peer conversations for business owners. The company operates a daily email newsletter (the Morning Report), a weekly podcast, monthly mastermind sessions for Founding Members, and limited-capacity in-person events (21 Hats Live). The platform features real business owners speaking candidly about their experiences rather than offering prescriptive how-to advice.
Is 21hats a public or private company?
21hats is a private company. It is classified as founder individual operated bootstrapped and is currently operating.
When was 21hats founded?
21hats was founded in 2019. It employs 1 to 10 people.
How does 21hats make money?
Three revenue lines are on record. Newsletter Subscription is the primary driver. The others are events and Mastermind Sessions and podcast Sponsorships.
Does 21hats have an API?
No public API is recorded for 21hats.