freemium Startups

NightEye is a dark mode browser extension launched in May 2018 that grew to 100,000 users and 4,500 paying customers through organic SEO. The bootstrapped side project from Razor Labs agency charges $9/year for subscriptions and $40 for lifetime licenses, generating approximately $2,500-$2,700 in monthly recurring revenue with an 86% annual retention rate.

Flowster is a workflow and process management SaaS tool built by serial entrepreneur Trent Deersmid after he sold $412,000 worth of documented Amazon reseller processes in the first seven days of offering them. Starting with 5,000 free users and 500 paying subscribers at $20/month average ($120k ARR), Trent bootstrapped the company while running a parallel $3.1M e-commerce business, and is now expanding upstream to serve brand owners with enterprise-focused pricing at $99/month.

Doist, founded in 2007 by Amir Salihefendic as a side project, bootstrapped Todoist to $14M ARR with 200,000+ customers through native mobile apps and organic growth. The company remains fully remote, 100% bootstrapped, and profitable from early years, with founder declining acquisition offers to pursue a $100M revenue goal within five years. They recently launched Twist, an asynchronous communication tool, generating $600K annually.

ThinkOutLoud.io is a bootstrapped SaaS product being built by Jim (a UX designer and coach) and his technical co-founder Scott to democratize user testing. Launched in private beta in May 2021 with 30 beta signups, the founders are approaching this as a lifestyle business, dedicating only 8 hours per week while Jim generates $5.3K/month from his UX coaching and design services agency. They aim to acquire 10 paying customers by end of year with a freemium pricing model determined by user feedback.

Divvy modernizes finance for businesses by combining expense management software and corporate cards into a single platform, offered free to SMBs while monetizing through credit card interchange fees (200-300 basis points). Founded by Alex Bean and Blake in 2017, the company grew from 1,000 customers in 2019 to over 10,000 customers today, with 100% year-over-year revenue growth and a clear path to $100M+ ARR within two years, processing between $1B-$100B in annual spend across their customer base.

Clap is an asynchronous meeting platform founded by Pierre Tuzovic and Robin that allows teams to share video updates, collect in-context feedback, and make decisions without being in the same room at the same time. After a viral LinkedIn announcement in January 2024 that garnered 45,000 views, the startup raised $3 million at a $17.5M post-money valuation while still in private beta with 3,000 waitlist signups and 100 monthly active users.

Yabs is an interview intelligence platform built on top of Zoom that helps companies record, transcribe, and analyze interviews to improve hiring quality and speed. Founded in 2018 by French entrepreneur Raphael Danilo, the company grew from serving Fortune 500 customers like Nissan to adopting a product-led growth strategy with a free forever plan. After bootstrapping initially, Yabs raised a $2.5M seed round in 2021 and has grown 3x year-over-year to $20K MRR.

Play is a native iOS design tool that lets teams design, prototype, and share mobile products directly on their devices, leveraging native iOS elements that desktop tools like Figma cannot access. Founded by Dan Lasa Vita and three co-founders from the agency Firstborn (sold to Dentsu in 2012), Play raised $3M pre-seed and $6.1M seed funding, accumulating 30,000 waitlist signups, 11,000 app installs, and 4,500 active users with strong retention cohorts (80-85% at 5-7 weeks). The product is gaining traction through word-of-mouth among product designers who value the ability to design with real native iOS gestures and controls.

Disco is a SaaS platform for knowledge creators to build live learning communities, founded by Candace Factor (former head of business at Wattpad). Launched in August 2020, the company raised $750k in pre-seed (friends & family) and $5M in seed funding, with plans to hit $1M+ in revenue. They use a freemium model (10% take rate) plus $85/month SaaS plans, with hundreds of customers and some creators on track to do seven figures annually.

Markup Hero is a bootstrapped screenshot and annotation tool founded by serial entrepreneur Jeff Solomon in 2020. The product has grown to ~10,000 paying customers generating approximately $20,000/month MRR through SEO-driven content marketing and a freemium model ($4/month for paid tier). Operating as a lean 3-person team with minimal overhead, it's positioned as a profitable lifestyle business.

CakeEquity is a cap table management platform for startup founders built by Kim Hansen after struggling with equity management in his previous ventures. The company launched in 2019, pivoted from blockchain, and achieved $70K MRR with 650 paying customers through a product-led growth shift and strategic partnerships. They've raised $4.5M total ($500K pre-seed, $1M seed, $3M series round) and are expanding globally across the US, UK, and Singapore.

B is a visual builder SaaS for creating emails, landing pages, and other digital assets, founded in 2014 as a business unit within publicly-traded Italian company Growance. Starting with just a €500k credit line and bootstrapped growth, B has grown to $10M ARR through product-led growth, with half the revenue from white-label embeds in other software and half from direct customers. The company recently embraced freemium, which increased signups by 60% and active user growth from 17% to 55% year-over-year.

Toggle 3D is a freemium 3D studio platform that democratizes 3D content creation for e-commerce, AR/VR, and metaverse applications. Spun out from 3D.ai (acquired by Next Tech in 2021), the company launched in beta in September 2022 with 145 users and an 85% activation rate. They offer a free tier and a $29/month pro plan with unlimited designs and export capabilities.

NP Digital is a nine-figure revenue ad agency founded by Neil Patel that pioneered a product-led growth strategy by acquiring and giving away free software tools (Ubersuggest, Answer the Public) to generate leads. With 40% of agency customers coming from Ubersuggest users and collecting 20,000+ leads monthly, the company demonstrates how free premium software can drive acquisition into higher-margin services, generating eight figures in EBITDA from both the software division and agency services.

You Can Book Me is a bootstrapped SaaS scheduling tool founded by Bridget Harris and co-founder Keith that has reached $5M ARR with over 20,000 customers. Built in 2003 as an alternative to SurveyMonkey-like products, the company deliberately chose to bootstrap rather than raise venture capital, allowing it to remain profitable and maintain control over growth. Bridget shared five key lessons from bootstrapping to $5M ARR at SaaSOpen conference: timing, skills, hiring, cash management, and maintaining personal boundaries.

Chaser is a Slack-native project management tool that lets users delegate tasks to anyone via Slack or email without requiring them to be platform users. With 100 companies signed up over 16 weeks and 43% retention, the team (2 unpaid co-founders + 2 full-time contract developers) raised $120k ($100k pre-seed at $7M cap + $20k angels) and is focusing on growth and product-market fit before monetization.

CJ built Mostly Metrics, a newsletter for CFOs launched in December 2020, starting from zero subscribers by obsessively engaging on Twitter around relevant keywords and partnering with B2B companies like Ramp and Brex. The newsletter grew to 35,000 subscribers (7,000 of whom are actual CFOs) in 1.5 years with a 46% open rate and 5-7% click-through rate, attracting sponsorships of $5-10k per post and up to $100k for bundled deals. He also launched a podcast called Run the Numbers with Turpentine Network while maintaining his full-time role as CFO at Parts Tech, planning to transition fully to media within three years.

Tropical MBA is a content and coaching platform for entrepreneurs, led by Dan and Ian. They provide educational content on business fundamentals including customer acquisition, pricing, retention, and growth strategies through podcasts, newsletters, and coaching communities. The platform serves entrepreneurs at various levels, from $250K+ founders to 1M+ revenue founders.

Discord is a social platform founded by Jason Citron in 2015 that evolved from his earlier failed gaming social platform ventures. Originally designed as a digital gathering space for gamers, it has grown to 150 million monthly active users and now serves as a communication hub for diverse communities beyond gaming. The platform represents Citron's successful pivot after two previous business failures.

Matt Mullenweg built WordPress after his employer CNET rejected his pitch for WordPress.com, launching it independently and eventually housing it under Automattic. The platform grew to power over 40% of websites on the internet, with Automattic reaching nearly 2,000 employees and a $7 billion valuation through a freemium model emphasizing free, customizable code.