freemium Startups

Darren Rouse built Pro Blogger starting in 2002 as a personal blog, eventually consolidating 20-30 topic-specific blogs into his two main properties: Pro Blogger and Digital Photography School. Pro Blogger generates ~$4,000-5,000/month from eBooks plus six-figure event profits, while Digital Photography School reaches 4 million monthly visitors and generates over $1M annually through eBooks, affiliate marketing, and advertising. Growth is driven primarily through organic search, content marketing (7-8 pieces per week), and an email list of 950,000 subscribers adding 800 new emails daily.

Tweet Jukebox is a content distribution system launched by Tim Fargo in February 2015 to solve his own pain point of managing frequent tweets for marketing purposes. The product grew to 16,000 users by the time of this interview, with approximately 150,000 tweets distributed daily, operating on a free model before planned paid tiers launching in 2016 at $9.99/month entry level.

Yuri Elkaim built a digital health and nutrition business centered around the Super Nutrition Academy membership ($49/month) and the Defeating Diabetes Kit ($37 one-time offer). By offering a free 1-month academy trial with the diabetes kit, he achieved a 60% upsell conversion rate and ~$237 average customer lifetime value, enabling him to profitably acquire customers through paid media at $50-55 CPA, generating approximately $65,000 monthly from the academy alone (1,300 members) plus additional revenue from nine other product brands and consumable products.

Stephanie Nicolich founded Success Society in August 2015 as a free community platform for women entrepreneurs, offering resources, tools, training, and mentoring from seven expert CEOs. The platform has grown to tens of thousands of active members with over 500 fully profiled members, generating revenue through a $97/month e-course offering and an $1,997 eight-week intensive bootcamp that runs quarterly with attendance doubling each iteration. She's built a team of eight and leveraged email marketing (4,000 opt-ins in a four-week period from a free lead magnet) to drive growth.

Jim Fowler is a serial entrepreneur who built Jigsaw, a business data company, from 2003 and sold it to Salesforce in 2010 for $175 million (with a $25 million earnout). The company had $17-18 million in annual revenue the prior year with a $25 million run rate at the time of sale and was already cash flow positive. He is now the founder of Owler, a free competitive intelligence tool that tracks over 13 million companies using a crowdsourced model.

Scott Voelker built The Amazing Seller as a podcast and educational platform teaching others how to sell on Amazon through FBA private labeling. Starting his Amazon business in October 2014, he achieved $307,000 in gross revenue within 12 months with a 38% margin (~$114,000 net), while simultaneously building a successful podcast and coaching business. His teaching business now generates 75% of his income, demonstrating the power of documenting and monetizing expertise.

Bundle is a location-driven mobile app that aggregates local news as users move around their city. Kelvin Lockwood left a £35k account management job in the UK to build the app, which had 50 beta testers in the UK and 20 in the US at the time of this interview. The business model relies on mobile advertising, with projections of £25M annual revenue from 6 million users based on a £5-7 CPM.

Nick Sonnenberg is a former Wall Street high-frequency trader who gave up a seven-figure salary to launch Calvin App, a productivity tool that helps users store 'someday' events and simplifies scheduling by showing overlapping free time without exposing full calendar details. Launched in public beta with ~400 monthly active users after being featured at Twitter's developer conference for innovative API integration, Calvin is pursuing a $750K funding round at a $6-8M pre-money valuation with plans to monetize through affiliate partnerships and brand integrations.

iSideWith is a political information platform that uses an engaging quiz format to match voters with political candidates and issues. Founded by Taylor Peck and an engineer co-founder, the platform went viral on Facebook, reaching over 25 million quiz takers in four years through organic sharing, with 1.5 million new completed quizzes per month. While currently generating modest revenue (~$10k/month from Google AdSense), Taylor is building toward monetization through sponsored candidate communication tools and email-based campaign offerings.

Harry Campbell quit a six-figure aerospace engineering job at Boeing to build The Ride Share Guy, a leading content platform serving ride share drivers. Starting with a blog and podcast, he's grown to 450,000 monthly page views and 10,000 email subscribers, generating $25K/month through driver referrals, direct advertising, and an insurance marketplace.

John Lee Dumas built Entrepreneur on Fire, a daily podcast interviewing successful entrepreneurs, which generates over $300,000 annually with over 1 billion unique monthly listens. Recognizing a gap in helping his audience actually accomplish their goals (not just be inspired), he created the Freedom Journal, a physical goal-setting workbook priced at $35 with a $6.50 production cost, launching via Kickstarter with a partnership to donate $25,000 per funding level to pencils of promise charity.

Chat with Traders is a weekly podcast launched by 25-year-old Aaron Feifield in January 2015 that interviews successful traders to help others learn trading. Starting from zero monetization but focused on audience growth, the podcast reached over 620,000 cumulative downloads in its first year with nearly 5,800 email subscribers, primarily driven by consistent weekly episodes and active Twitter engagement.

Clue is a period tracking and fertility app founded by Aida Tannen that has grown to nearly 3 million monthly active users across 180+ countries. The company raised $10 million from Union Square Ventures and other investors while remaining pre-revenue, strategically focusing on user growth before monetization. With a team of 24, Clue is one of the most popular health and fitness apps globally, particularly in the US, Germany, France, and Mexico.

Blab is a live conversation platform launched in January 2016 that allows users to broadcast live discussions where audiences can comment, chat, and call in to join conversations. Founded by Sean Peary after experiences in sushi, biotech, and an idea lab in San Francisco, Blab achieved millions of watch minutes per week with daily active users watching for over an hour per day, competing with Netflix and traditional TV by offering niche content from everyone ranging from basement creators to major brands like ESPN, UFC, Adobe, IBM, and Cisco.

Latergram is a freemium SaaS platform that allows users to schedule and post to Instagram, launched in May 2014 by Matt Smith and co-founders. Starting with 20,000 signups at launch through heavy PR and founder outreach, the company grew to nearly 500,000 users and 3,000-4,000 paying customers generating $50,000 MRR by January 2016. The company raised a $1.2M seed round from investors including Rocket Ship and angels like Heaton Shaw and Aspect Ventures, aiming to reach $1M ARR in 2016 with 25-30% month-over-month growth.

Shelf Media is a digital-only publishing company founded by Margaret Brown in 2010 that creates niche magazines including Shelf Unbound (indie book reviews with 125,000 readers across 75+ countries), Middle Shelf, and newly launched Podster (about podcasts). The company generates revenue through advertising and competitions, with Shelf Unbound alone generating approximately $120,000 annually from ad sales at $20,000 per bi-monthly issue, plus $40,000 annually from a book competition with 1,000 entries per year.

iMoji is a sticker platform that enables users to create and share custom emojis across messaging apps. Founded by Daniel Gruselowski and Jason Stein with four other co-founders, the company raised $2M in seed funding and grew to over 1 billion impressions per month by December 2015. They monetize through partnerships with messaging apps and plan native advertising as their primary revenue model.

Mailbird is a desktop email client and unified communication tool built by CEO Andrea Lubier, based in Bali, Indonesia. Launched in 2012, the company has grown to manage over 1 million email accounts with approximately 500,000 paying customers and $500,000 in annual recurring revenue. The business uses a freemium model with lifetime purchase and annual subscription options, leveraging flash sales and smart pricing structure to achieve 20% conversion rates on their website.

12 Labs, co-founded by Ashu Dubey, is a data science-powered weight loss application called Applays that has achieved over 500,000 downloads with approximately 75,000 monthly active users as of early 2016. The company raised approximately $1 million in a priced round led by Salesforce founder Mark Benioff in 2014, focusing on solving the engagement problem that plagues most health apps. While the free app generates no direct revenue, 12 Labs monetizes through an engagement platform for wearables that powers Applays and has shown a 7x improvement in user retention.

Stacking Benjamins is a financial entertainment podcast launched in March 2012 by Joe Saul-Sehy that grew to 152,000 monthly downloads by featuring accessible, magazine-style money content with personality. The show generates approximately $5,500 monthly from two main sponsors (Magnify Money and SoFi) at an 18 CPM rate, operates with minimal production costs (~$480/month), and is expanding into online courses to monetize the audience attention.