Dear Media

What Dear Media does

Dear Media is a multi-platform podcast network founded in 2018 by Michael Bosstick (with co-founder Raina Penchansky), operating more than 100 shows with roughly 90% of its catalog skewed to female-facing audiences in pop culture, wellness, and lifestyle. The network's core product is an owned-and-operated portfolio of podcasts distributed across Apple, Spotify, and YouTube, anchored by a small group of A-list hosts including a flagship property tied to the Kardashian franchise (The Toast, renewed under a three-year deal in late 2025). Dear Media also operates Dear Media Shop, an in-house commerce surface, and runs Dear Media By Night/Day live events, including geographic activations such as Austin, that convert its online audience into in-person and merchandise revenue.

The company generates revenue through three primary streams: (1) podcast advertising and sponsorships from brands in beauty, wellness, fashion, and consumer lifestyle; (2) commerce, including Dear Media Shop and equity-backed DTC brands such as The Skinny Confidential and, post-June 2025, Obé Fitness; and (3) live events and experiential monetization. The capital base includes an approximately $8 million round from Magnet Companies in April 2020 and an SEC-registered exempt offering of approximately $4.99 million in August 2022, with growth funded further through advertising cash flow and bolt-on M&A. According to Axios reporting referenced in the input, Dear Media crossed $50 million in revenue in 2024 with roughly 70% year-over-year growth, supported by a 101–250 employee base. Strategically, the company has pursued an offensive posture through vertical integration (fitness via Obé, lifestyle via Skinny Confidential), exclusive talent lock-ups (The Toast renewal), and new content surfaces (Polymarket partnership for "What Are The Odds?"), while operating with no disclosed proprietary AI/ML capability.

Name

Dear Media

Legal name

Dear Media LLC

Website

https://dearmedia.com

Company type

Private

Founded year

2018

Operating status

Operating

Headcount range

101–250 employees

Short description

Dear Media is a female-focused multi-platform podcast network of 100+ shows in pop culture, wellness, and lifestyle, founded by Michael Bosstick in 2018, monetizing through advertising, owned commerce, acquired DTC brands, and live events.

Ownership category

akta.pro rank

Product category

Podcast Network

NAICS

Media Streaming Distribution Services, Social Networks, and Other Media Networks and Content Providers (516210)

akta.pro primary industry

Podcast Networks & Multi-Show Publishers (MPACADAB)

akta.pro secondary industries

Podcast Hosting Platforms (RSS, Analytics, Distribution) (MPACADAA), Live Podcast Recordings (MPAGACAJ), Audio Production & Podcasting (BPAFAIAE)

Keywords

• Podcast network
• Digital media
• Creator economy
• Lifestyle content
• Audio entertainment

Headquarters

HQ city

Austin

HQ country

United States

HQ region

North America

Offices1 record

Markets served

GTM type

B2C

Offering type

Digital Commerce or Content

Cost components

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

Revenue model

1. Advertising and Sponsorships: Primary revenue stream from podcast advertising and sponsorships across the network of 100+ shows targeting female audiences in pop culture, entertainment, and lifestyle categories.
2. Commerce and Product Sales: Revenue from direct product sales including The Skinny Confidential branded merchandise (ice rollers, caffeinated sunscreen, mouth tape, nontoxic toilet paper) and Obé Fitness platform.
3. Live Events: Revenue from in-person experiences including 'Dear Media By Night', 'Dear Media By Day' events, and various podcast live tours featuring network talent.
4. Acquisition Investments: Strategic investments and acquisitions such as Obé Fitness to enhance brand-building and monetization capabilities for female-focused content.

Pricing tiers

Go-to-market motion3 records

Distribution channels6 records

Marketing channels5 records

Core offering

Dear Media is a multi-platform podcast network that produces, distributes, and monetizes over 100 podcasts primarily targeting female audiences across pop culture, wellness, beauty, parenting, and lifestyle categories. The company also operates a branded merchandise e-commerce store (Dear Media Shop), produces live events (Dear Media IRL), and has expanded into fitness and wellness content through acquisitions including Obé Fitness and a strategic investment in The Skinny Confidential brand.

Product overview

Dear Media is a multi-platform podcast network and lifestyle media company founded in 2018, operating as a platform-plus-services model. The core product is the Dear Media Podcast Network hosting over 100 shows across categories including pop culture, health and wellness, beauty and style, relationships, career and money, and parenting. The portfolio includes flagship shows like The Toast (with its landmark three-year renewal), Khloé in Wonder Land, Coming In Hot, and The Bossticks, complemented by acquired brands such as The Skinny Confidential (with its product line including ice rollers and skincare) and Obé Fitness (digital fitness platform acquired in 2025). The company has expanded beyond traditional podcasting into creator-led live experiences through Dear Media IRL events (including By Night and By Day formats), e-commerce via the Dear Media Shop, and the What Are The Odds? podcast in partnership with Polymarket. The network maintains a female-focused positioning with approximately 90 percent of content targeting women, generating over $50 million in 2024 revenue with 70 percent year-over-year growth.

Differentiator

Problem solved

Functional benefit

Brands

• The Skinny Confidential: Beauty and wellness brand by Lauryn Bosstick, including blog, podcast, and product line (ice rollers, skincare, beauty products)
• Dear Media IRL
• Dear Media Shop

Products and services

• Dear Media Podcast Network Multi-platform podcast network hosting over 100 entertainment, pop culture, and lifestyle shows, with 90% female-facing content, offering advertising, production, and creator partnership services for listeners across categories including pop culture, wellness, beauty, parenting, and relationships.
• Dear Media Shop Proprietary e-commerce platform selling branded merchandise and products from podcast hosts and shows, including the Lucky Girl and She's So Lucky product lines, with items ranging from $18 to $55 in price.
• Dear Media IRL Events
• The Toast
• Khloé in Wonder Land
• Obé Fitness Digital fitness platform acquired by Dear Media in 2025, offering innovative workout content tied to popular media and enhancing the company's fitness and wellness vertical for women.
• The Skinny Confidential Brand Beauty and wellness brand founded by Lauryn Bosstick, including blog (300,000 subscribers), podcast content, and product line featuring ice rollers (200,000+ units sold), caffeinated sunscreen, mouth tape, and nontoxic toilet paper.
• What Are The Odds? Weekly podcast partnership between Polymarket and Dear Media combining pop culture news with real-time prediction market trading data, hosted by Claudia and Jackie Oshry (The Toast).

Quantifiable outcome

• Over $50 million in 2024 revenue with 70% year-over-year growth
• +3 more outcomes

Named customers7 records

Segments4 records

Ideal customer profiles3 records

Technology focussed No

API detail

Has API

No

API docs

API detail

Core technology

AI maturity

App detail

Partnerships

Five partnerships are on record, tiered core, flagship and minor.

• PolymarketcoreGTM or Marketing Partner · 20 June 2026Dear Media partnered with Polymarket, the world's largest prediction platform, to launch 'What Are the Odds?' - a weekly 15-minute podcast combining pop culture news with real-time trading data from the platform. The show premiered with hosts Claudia and Jackie Oshry (The Toast) and marks Polymarket's entry into mainstream audio/video content.
• The Toast (Claudia and Jackie Oshry)flagshipStrategic or Co-development Partner · 2 October 2025Landmark three-year renewal deal securing exclusive rights for advertising and production of The Toast podcast. The show outperformed traditional morning shows among millennials and Gen Z, surpassing 100 million Spotify streams. Deal followed competitive bidding involving SiriusXM and iHeart.
• Obé FitnesscoreStrategic or Co-development Partner · 23 June 2025Dear Media acquired Obé Fitness, a digital fitness platform co-founded by former CAA agents Mark Mullett and Ashley Mills. The platform is known for innovative fitness content tied to popular media and celeb-favorite workouts. Acquisition enhances Dear Media's focus on fitness and wellness content.
• Ritual (Kat Schneider)minorStrategic or Co-development Partner · 7 January 2025Dear Media launched 'For The Real Body Builders' podcast hosted by Kat Schneider, founder and CEO of Ritual vitamin company. Partnership brings wellness-focused content to the network.
• The Skinny Confidential (Lauryn Bosstick)coreStrategic or Co-development Partner · 1 January 2021Dear Media invested $1 million in The Skinny Confidential brand alongside Drybar founder Alli Webb. The beauty and wellness blog has grown to 300,000 subscribers and 2.5M social followers. Product line includes ice rollers (200,000+ sold), caffeinated sunscreen, mouth tape, and nontoxic toilet paper.

Scale indicators6 records

Recent moves7 records

Expansion highlights5 records

Direct peers

• iHeartPodcasts: Podcast publishing arm of iHeartMedia, distributing hundreds of shows and competing head-to-head for talent and ad dollars. Closely aligned business model of network aggregation plus monetization.
• Wondery: Amazon-owned premium podcast network producing and licensing scripted and unscripted shows across multiple genres. Directly comparable as a multi-show publisher with celebrity hosts and brand extensions.
• Audioboom: Independent podcast hosting and ad-network platform serving premium creators with monetization, production, and distribution. Comparable as a podcast network/platform serving lifestyle and entertainment creators.
• Pushkin Industries: Premium independent podcast publisher producing high-end narrative and interview shows. Comparable as a multi-show publisher monetizing through advertising, licensing, and branded content.
• Podcast One: Podcast network producing and distributing a large catalog of celebrity and lifestyle shows. Comparable multi-show publisher model targeting advertising and sponsorships.
• Betches Media: Female-focused digital media and podcast company targeting millennial and Gen Z women with pop culture, dating, and lifestyle content. Comparable audience and content vertical.
• The Ringer: Spotify-owned podcast and media network producing pop culture, sports, and lifestyle shows. Comparable multi-show publisher model with comparable celebrity-driven host roster.
• Lemonada Media: Female-founded podcast network focused on storytelling across wellness, relationships, and lifestyle. Closely comparable female-led, premium-narrative podcast network competitor.

Broad incumbents

• SiriusXM: Satellite radio and audio entertainment giant with a large podcast portfolio (including Stitcher). Comparable as a major bidder for Dear Media's flagship talent and as a broader audio incumbent.

Emerging players

• Girlboss Media: Female-focused media and community platform producing editorial, events, and podcasts for millennial and Gen Z women. Comparable female-skewing content vertical with lighter scale.

Market position

Strengths5 records

Weaknesses5 records

Competitive moat5 records

Key risks1 record

Key highlights7 records

Customer concentration

• LinkedInlinkedin.com/company/dear-media
• Xx.com/dearmediastudio
• Facebookfacebook.com/dearmediastudio

Revenue estimate

Valuation estimate

Number of profiles

Profiles4 records

Subsidiaries2 records

Funding overview

Funding rounds2 records

Investors1 record

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

M&A1 record

Investments1 record

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

Frequently asked questions about Dear Media