Own Pain 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.

MyTime is a two-sided marketplace and SaaS platform connecting consumers with local service businesses. The company operates a marketplace that takes a 40% commission on new customer acquisitions, plus MyTime Scheduler, online booking software designed to help businesses acquire, book, and retain customers. The platform serves over 2.5 million nearby businesses with approximately 1 million monthly visitors.

Scoop is a news discovery network and marketplace connecting journalists with newsmakers/companies. Founded by Bill Hanks, former VP of Corporate Communications at Real Networks and PR director at Microsoft, the platform has 630 registered journalists (6% of business journalism market) after 7 months and recently began generating revenue (~$1,000/month) by charging companies $250 to algorithmically match their news to relevant reporters.

BiggerPockets is a freemium community marketplace for real estate investors founded by Joshua Dorkin in 2004. Starting as a personal forum to help himself learn real estate investing, Dorkin spent 3-5 years focused purely on building community before monetizing. The platform now has 390,000 members, over 10,000 paid subscribers at $9-$29/month, 1.2 million monthly unique visitors, and a podcast ranked #14 in business podcasts, generating well over $1.1 million in annual recurring revenue.

Neil Patel built Quicksprout into a content powerhouse generating 3.9 million monthly website visits, collecting approximately 1,000 email leads per day through educational marketing content. He is now building a SaaS product that automates the marketing optimization tasks he and his team have performed for hundreds of clients, offering a freemium model to help small businesses grow their web traffic without expensive consulting.

Jason Zook is a creative entrepreneur who sold his last name twice (first for $45,000 to headsets.com) and is known for making over a million dollars wearing t-shirts for brands. His latest venture, Buy My Future, launched with a unique 60-day transparent journal on Medium documenting the entire project, followed by 44 customer interviews to craft messaging. In just two weeks, he sold 165 lifetime access units at $1,000 each, generating $165,000 in revenue with $120,000 in profit after $8,900 in expenses, building a community around guaranteed access to his future projects.

Basic Bananas is a marketing consulting and education agency founded by Christo Haugh that sells a year-long program called "The Clever Bunch" to small business owners in Australia (expanding to New Zealand and Los Angeles). The program costs $8,000-$12,000 annually and includes monthly workshops, weekly webinars, and online support. Over the past 12 months, Basic Bananas generated between $2-3 million in revenue with a 14-person team, using a paid advertising funnel that costs $20-50 per workshop attendee and converts 10% to the full program.

The Sales Whisperer, founded by Wes Schaefer in 2006, is a sales and marketing agency that generates approximately $500k annually by helping entrepreneurs implement CRM systems and sales strategies. Wes has built a recurring revenue business through Infusionsoft affiliate partnerships, earning $30k-$40k monthly in passive commissions from 300+ active customers, while diversifying into HubSpot, Active Campaign, and done-for-you support services.

Charisma on Command is an online education platform co-founded by Charlie Hooper that teaches social confidence and charisma. Using a lean startup approach with customer surveys and a creative scholarship contest, Charlie pre-sold $12,500 worth of a course that didn't exist yet by having 50 people write persuasive essays about why they needed the program. The course has since evolved into a membership portal with a sales page converting at 2-3% from cold traffic.

Baby Bathwater Event Series, co-founded by Hollis Carter and Michael Lubbidge, is a high-end mastermind event that brings together 100 carefully curated entrepreneurs and founders. The second official event generated approximately $330,000 in revenue from 110 attendees paying $3,000-$5,000 per ticket, with all profits reinvested into the community and future events.

Ignite the Drive is a content platform founded by Garrett Dunham, a serial entrepreneur and startup advisor from Silicon Valley, after his previous accelerator Pre-Backed shut down due to burnout and a failed enterprise deal. The site shares tips, tricks, and frameworks for entrepreneurial mental fortitude through blogging and a newsletter. Currently generating revenue in the hundreds of dollars, it operates as a labor of love rather than a primary revenue driver.

Rob Burke founded MindTalk Technology to create communication devices built into mouth guards that let users hear through vibrations transmitted via their jawbone and teeth. The company has soft commitments for 5,000 units and is working with professional teams like the Dallas Cowboys and Dallas Stars. Rob is raising $1.7 million on a convertible note with 6% interest, having already secured $100,000 in soft commitments.

Jonathan Goodman is a 29-year-old entrepreneur who built the Personal Trainer Development Center and Viral Nomics brand, selling courses, books, and training programs to fitness professionals. His 1K Extra course launch from September 28-October 6 generated $299,962.15 in revenue with $285,433.38 in profit by using social-gated content (an Instagram operations document), email list leverage, and strategic $3,012 retargeting spend that drove 78-118 additional sales. He travels the world full-time with his girlfriend, using revenue to fund experiences across Hawaii, Thailand, Uruguay, Iceland, and Costa Rica.

Brian Brushwood is an entertainer and content creator with over 400 Discovery Channel episodes, 1M+ YouTube subscribers, and multiple podcasts. Three years ago, he launched Scam Stuff (Modern Rogue Gear), an online store selling magic equipment, lockpicking sets, and bar culture products. The online store has become his highest revenue stream, complementing his diversified income from podcasts ($2,000/episode via Patreon), corporate speaking ($10,000+/gig), stage shows, and TV production work.

MeowTel is an Airbnb-style marketplace for cat sitting that shares profits with local shelters. Founded by Sanya Petkovich in August 2015 after she left a career in big tobacco, the platform had 50 registered sitters and 2-3 actual bookings three months after launch. The business is bootstrapped and focuses on building supply and demand equilibrium across its initial markets of San Diego, Richmond Virginia, and the San Francisco Bay Area.

Colin Huggins is a classical pianist who performs on the streets of Washington Square Park in New York, earning approximately $100,000 annually through donations. Over nine years, he refined his performance strategy—from making $100-150 per day initially to rarely making less than $1,000 per day by understanding audience psychology, strategic music selection, and crowd dynamics. Beyond street performance, he works with the Reciprocity Foundation, writing songs for homeless youth in New York City.

Elliot Hulse built Strength Camp from the back of his car while drowning in $90,000 of credit card debt (2007-2010), transforming it into a seven-figure business with 1.3+ million YouTube subscribers and 300,000+ email subscribers. His business model combines free content marketing via YouTube with a customer ascension ladder selling ebooks, programs, workshops, and high-ticket conferences like the Non-Jobs Summit ($297-$397 per ticket). Revenue peaked at $80,000+ per month through strategic content repurposing and email conversion optimization.

Joe Pulizzi built Content Marketing Institute into a dominant player in content marketing education through a multi-revenue model centered on large-scale events. Content Marketing World, their flagship conference, generates approximately 70% of revenue through paid registrations ($1,100 average yield per person) and sponsorships, with the 2016 event projected to bring in $9.25-$9.5M in total revenue and $2.5M in profit.

Jeffrey Zorofsky co-founded Witchcraft in 2003, a fine dining-quality sandwich shop that brought seasonal, locally-sourced ingredients to a casual format. The first location generated over $1.5 million in its first year with lines out the door, and the concept scaled to 15 active locations (17 total opened, 2 closed) across 6 years, reaching approximately $20 million in annual revenue with 400+ employees. Jeffrey later became a judge on Bravo's Best New Restaurant and shifted focus to advising food entrepreneurs and businesses.

Bazi Hassan is an affiliate marketer who generated $1.1 million in sales revenue over 3.5 years by mastering paid traffic acquisition (primarily via TrafficVents PPV network) and email marketing funnel optimization. Starting with just $5,000, he built a 165,000-person email list and earned approximately $500,000 in commissions by promoting high-EPC offers like MOPE (nophonebiz.com). He is now launching his own coaching platform to serve the customers he surveyed and learned from while marketing affiliate products.