subscription Startups

Pieter Levels is a solopreneur running a portfolio of 7 bootstrapped projects generating ~$2.7M ARR with 13M monthly active users. Starting in 2014 while traveling, he built Nomad List, Remote.ok, and other niche products targeting remote workers and digital nomads. His approach combines radical transparency (publicly sharing revenue), lean PHP/jQuery stack for fast iteration, and a personal brand flywheel where each product feeds audience and content back into the ecosystem.

Only Problems is a subscription-based app pitched as 'OnlyFans for therapy' where subscribers pay monthly to observe real therapy sessions anonymously in a fly-on-the-wall format. Therapists receive subsidized or free sessions while gaining more clients, viewers get entertainment and secondhand therapeutic benefit, and the platform monetizes through a revenue-sharing model where users can tip therapists with hearts to influence payouts.

Missouri Star Quilt Company is a bootstrapped e-commerce business that grew from zero to over $100M in annual revenue in 12 years by targeting the underserved 45-70 year old quilting demographic. Founded by Tom and his mom in 2009, the company pioneered accessible quilting tutorials on YouTube and built community through forum engagement, eventually expanding into owning two towns (Hamilton and Kingston, Missouri) as physical brand experiences. The company is now 400+ employees, 90% online revenue, and valued at potentially $1B with 20% EBITDA margins.

Nikita Bier, who previously sold his viral high school app TBH to Facebook for $40-100 million, launched a new app called Crush designed to replicate that success with a monetization twist. The app uses a $6.99 weekly subscription ($28/month) model to reveal who voted for you in anonymous polls, and was geofenced to specific high schools in Georgia and Alabama. The app went viral within its targeted high school networks but faced controversy with rumors of misuse, leading to app store takedowns and rebranding efforts.

Kate (Amaranth) is the #1 creator on OnlyFans, earning $30M+ on the platform in just two years (April 2020 onwards). She built a sophisticated media empire with a 5-person core team plus extended staff, then expanded into Real Work—an agency offering virtual assistance services to other OnlyFans creators. Her growth was driven by leveraging an existing Twitch and Patreon audience, strategic use of earned media when her Instagram was banned, and continuous optimization of conversion tactics across multiple platforms.

Yardstick, founded by Anand (founder of CB Insights), is a 90-day-old SaaS platform that charges enterprise software buyers $30-40k annually for researcher-conducted interviews with software vendors about pricing, satisfaction, and competitive positioning. The business inverts the typical review site model by charging buyers (not vendors) for verified data and positions itself as a high-value alternative to G2 Crowd by conducting original research rather than relying on unverified user reviews.

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.