subscription Startups

Brendan Schaub transitioned from UFC fighter to stand-up comedian to podcast entrepreneur. After 6 years building Showtime's podcast division from zero to 600k subscribers, he left to start Thick Boy Studios in December 2022, bringing 7 shows including 'Fighter and the Kid' and 'The Shop Show'. A year in, he's rebuilt to ~160-170k subscribers and focuses on audio metrics over YouTube vanity metrics.

Divi is a clean haircare and scalp care brand launched by Jordan Austin, an Instagram influencer with 2-2.5M followers across platforms, in October 2021. The product originated from Jordan's personal struggle with stress-induced hair loss and evolved from DIY scalp serum recipes she shared with her audience. In just over one year, Divi generated approximately $40M in revenue, driven almost entirely by organic word-of-mouth and user-generated before-and-after content rather than Jordan's direct audience.

PetEx is a highly technical specialist software company for oil and gas operations based in Aberdeen, Scotland. Started in 1990 as a consulting firm, they pivoted to software and generated £78 million (~$100 million USD) in revenue last year with £58 million (~$67 million USD) in profit, paying out £41 million (~$60 million USD) in dividends. With only 420 customers paying ~$300,000/year per license, they achieve exceptional profitability through enterprise-focused, high-value relationships.

After.com is a cremation-as-a-service platform founded by Mormons based in Provo, Utah. The company handles the full logistics of cremation—from lead capture to tracking—similar to Domino's Pizza Tracker, allowing customers to pre-plan or arrange services after death. The business was built on recognizing a major demographic trend: cremation in the US rose from 10% to over 50-70% of end-of-life choices in the past 20 years, a 'one chart business' opportunity.

Laird Superfood began as Laird Hamilton's home-made superfood recipe that evolved into a commercial product launched online with minimal capital investment of $20-30k. The company achieved rapid early traction through Hamilton's existing following and engaged community, reaching approximately $100-150k in revenue within the first year. The brand went public at a $400 million market cap when doing roughly $40 million in annual revenue, though stock performance has declined recently.

Derek built a nine-figure business portfolio (Gorilla Mind supplements, Merrick Health telemedicine, Intelligent Elephant hair loss products) starting from YouTube content and affiliate marketing. Gorilla Mind alone is estimated at $6-8M monthly revenue with over 1M monthly visitors, while Merrick Health operates a subscription-based telemedicine model at $300+/month per customer. His strategy: monetize what he already uses, replace affiliate recommendations with owned products, and leverage 1.9M YouTube subscribers and influencer partnerships spanning tens of millions of followers.

Brett Adcock founded Figure AI to build humanoid robots for commercial labor after selling his recruiting marketplace Vettery for $110 million and taking Archer Aviation (electric VTOL aircraft) public at a $1.5B valuation. He went all-in on Figure, nearly bankrupting himself personally while the company reached a $7M/month burn rate, ultimately betting that the humanoid robotics market could become one of the world's largest industries worth more than autonomous vehicles.

Blockworks is a crypto-native media and information company founded in December 2017 by Jason and co-founder Mike. Starting from cold LinkedIn outreach (300 messages/day), they bootstrapped to $25M+ revenue by building a media platform with podcasts, newsletters, conferences, and eventually a subscription research platform (Blockworks Research). The company scaled profitably from day one, with major conferences like Permissionless generating over $10M in revenue.

Moises Ali bootstrapped Native Deodorant from a kitchen table to a $100M exit to Procter & Gamble. He built the initial website in 3 days using WordPress and Woo Commerce, deliberately avoiding expensive design agencies. The brand grew through word-of-mouth and built a post-purchase upsell mechanism that generated $700k monthly in travel-size sales.

Resi Club is a content-first platform focused on residential real estate coverage and data, co-founded by Anthony Pompliano and real estate expert Lance Lampard (former Fortune real estate editor). Launched just two months before this interview, the platform achieved profitability within the first month on a $100k initial investment and is positioned as the dominant voice in residential real estate commentary.

Spencer Scott launched Lonestar Trash in January 2024 after getting frustrated with his neighborhood's trash collection service leaving bins scattered across lawns and ditches. He posted in a Facebook community group asking about switching providers, received 150 comments, and convinced 200 households to commit to his new service. Within 24-48 hours of launching a simple website with a referral program, he collected $15,000 in pre-sales, purchased 200 trash bins, bought a garbage truck via American Express credit line, and launched his first route.

Follow Up Boss is a vertical SaaS CRM built specifically for real estate agents to manage leads from platforms like Zillow and Redfin. Founded by Dan (from Australia, based in Wyoming) 12 years before exit, the company took 4 years to reach $100k MRR with just 11 employees, bootstrapped entirely through Facebook group engagement and word-of-mouth. The company sold for $500 million ($400M cash upfront + $100M earn-out), demonstrating the power of patient, niche-focused founder persistence and organic growth.

Jenny AI is an AI-powered writing assistant for college students, founded by David Park. Started at $2K MRR in 2021, it grew to $300K MRR ($3.6M ARR) through strategic community building in Facebook groups and viral marketing on TikTok. The company was offered $3M but rejected it, now valued at $10-15M.

Syed Balkhi bootstrapped a billion-dollar portfolio empire centered on WordPress and related SaaS products without raising external capital. His strategy leverages what Andrew Wilkinson calls 'barnacle on the whale'—becoming deeply embedded in growing ecosystems like WordPress, QuickBooks, and Xero. His portfolio now generates over $100M in annual revenue and includes investments in companies like Seahawk Media (productized WordPress development services) and positions in open-source projects.

37signals is a 25-year-old self-funded software company built on the principle of profitability, high margins, and independence. Founded by Jason Fried and David Heinemeier Hansson, the company generates tens of millions in annual profits and maintains over 100,000 paying customers across multiple products including Basecamp, HEY, and their new ONCE line of one-time-purchase software. They've achieved this without external investment (except for shares sold to Jeff Bezos in 2006), aggressive marketing, or traditional goal-setting—instead operating with a focus on craftsmanship, low costs, and thoughtful product philosophy.

Umax is a viral mobile app that uses AI to rate users' physical attractiveness and provide personalized grooming and fitness advice to help them improve their appearance. Founded by an entrepreneur who observed the lookmaxxing trend on Reddit, the app has achieved 3.5 million downloads with 5,000 new signups per day and is generating $6M ARR through a $3.99/week subscription model, capitalizing on the growing cultural shift of men investing in personal aesthetics.

Support Shepherd is an offshore staffing SaaS platform founded by Marshall Haas around 2020 that helps e-commerce and service businesses hire skilled talent from Latin America and the Philippines at significantly lower costs. The company grew to a $52 million valuation within four years, with explosive growth after audience co-founders Sean Perry and Nick Huber joined as equity partners. In 2024, Nick Huber acquired a majority stake for $29.7 million, demonstrating the power of the 'audience co-founder' model in B2B SaaS growth.

FireCrown Media, founded by Craig Fuller (also founder of FreightWaves), acquired Flying Magazine in 2021 as a side project and scaled it into a $50M ARR media holding company. The business model inverts traditional magazine economics: instead of making money from readers, FireCrown uses media to acquire high-net-worth customers for higher-margin products like luxury real estate (an airport community development project in Tennessee with $25M in pre-deposits), jet brokerage, and marina investments across 44 magazine titles in expensive hobbies.

Firecrown Media is a portfolio of 54+ niche magazines (aviation, boating, trains, astronomy) acquired by entrepreneur Craig Fuller starting in 2021. Fuller bought Flying Magazine for ~$3.5M and grew it from $2.5M to $7M revenue in the first year by raising prices, upgrading quality, and building engaged subscriber bases. The company now generates ~$60M in revenue with 20% margins ($12M profit) and has expanded into adjacent commerce businesses—aircraft financing, e-commerce, and a 1,500-acre aviation community development—leveraging the magazine audiences' high purchase intent.

Christina Cacioppo left her role at Union Square Ventures to teach herself to code, spending two years building 35 failed projects before joining Dropbox. At Dropbox, while working on Paper, she encountered security and compliance (SOC 2) requirements that blocked product launches—a problem she realized startups faced without dedicated security teams. She validated the idea using just an Excel spreadsheet with early customers, then built Vanta into a multi-billion dollar compliance software company through word-of-mouth, founder networks, and podcast advertising.