Own Pain Startups

Ash & Anvil is an e-commerce apparel startup founded in 2015 by Steven Mazer and Eric, targeting the underserved market of shorter men (5'8" and under). They launched with an Indiegogo campaign seeking $10,000 and raised $26,000 in pre-orders for their flagship everyday casual button-down shirt. In their first year (November 2015 launch), they generated $50,000 in revenue, sold out 1,000 units in five weeks, and built a customer base approaching 1,000 with a 25% repeat purchase rate.

Skillbridge was a curated marketplace connecting high-end management consultants with companies needing specialized expertise. Founded in 2013 and launched in 2014, the platform used intelligent matching algorithms to connect consultants based on demonstrated competencies rather than ratings. In March 2016, just under $500,000 in projects were posted on the platform, with an average project size of $5,000-$10,000, and the company was acquired by TopTal.

Vango is a marketplace connecting emerging artists with novice art buyers, taking a 30% commission on transactions. Founded in 2013 by Ethan Appleby, the platform had 5,000 active artists and 100,000 lifetime buyers by March 2016, generating $1.6M in revenue in 2015 from nearly $5M in total art sales. Apple selected Vango as one of its top apps.

John Ruland is the #1 distributor among 1.5 million for Cutco Cutlery. Starting as a 20-year-old intern, he built a corporate gifting and consulting business around 'radical generosity'—helping executives strengthen relationships through high-end gifts. His company works with Fortune 500 brands and pro sports teams (25+ clients), creating custom gifts like Bluetooth speakers from Wrigley Field's historic wood, generating hundreds of dollars per gift in revenue.

The Slow Hustle is a long-form interview podcast launched in January 2015 by Peter Awad, who juggles podcasting alongside three other businesses (Import Auto Performance, Mission Meats food brand, and a previous failed startup). The show generates approximately 8,000-10,000 downloads per month with around 2,000 downloads per episode, and recently landed on the iTunes Podcasts homepage through authentic relationships rather than gaming the system. Peter has secured two sponsors (Iowa Startup Accelerator and a law firm) charging $3,000 per 16-episode package, generating roughly $187 per episode, covering costs while maintaining the show as a labor of love.

Ash Kumara built Trade Craft as a digital content network for millennials while generating significant revenue through book sales and speaking engagements. His book 'Confessions from an Entrepreneur' sold over 150,000 copies, generating approximately $300,000-$450,000 in revenue through a B2B approach targeting college entrepreneurship programs. By 2015, Kumara was generating approximately $90,000+ annually from speaking engagements (averaging $5,000 per speech) plus book royalties and startup advisory work.

Nathan Chan launched Founder Magazine in 2015 as a digital publication featuring interviews with successful entrepreneurs. Through aggressive Instagram growth strategies (posting 5-10 times daily with a virtual assistant), he built the account from zero to 700K followers in 16 months, generating 150,000+ email subscribers. Revenue comes from multiple streams including magazine subscriptions, digital courses (Instagram course and Founders Club membership with 400 paying members), and a weekly podcast with 70,000 monthly downloads.

Heather Ann Havenwood built DatingTriggers.com, an information marketing business teaching men dating skills, generating approximately $250,000 in revenue in 2015. The core product is a $47 one-time offer (Dating Up program) with an email list of 25,000 subscribers, but 80% of revenue comes from affiliate marketing partnerships where she earns ~$300-900 per day through email promotions, leveraging her expertise in email marketing and relationships rather than funnel creation.

Verbal Plus Visual is a digital agency founded by Anshay Bhatia in 2009 that specializes in e-commerce strategy, design, development, and optimization for innovative brands. The company grew from $150k in first-year revenue to low seven figures by 2015 with a healthy 20% net margin, and has become a premier Shopify partner. Their growth is driven primarily through strategic partnerships with complementary agencies and inbound leads from their strong portfolio.

Brian Baderra founded Amplify Relations (originally Grassroots 2.0) in 2009 at age 19 after being laid off from a political ad agency, bootstrapping the startup on student loans with his first client being a former employer client offering a few hundred dollars monthly. The company grew to 13 full-time employees and nearly $2 million in revenue by 2015, specializing in high-margin political campaigns, robocalls, and mass-market advertising for political entities, corporations, and startups. Their differentiation came from licensing a robocall system from Canada that yielded 90% margins on certain projects, while positioning themselves as a full-service agency of record.

Design Online Right is a web development agency founded by Rob Riggs in 2004 that builds technical, functional websites for small businesses and nonprofits. The agency grew from $5,000 in first-year revenue to $1.2M in 2015 with a 30% net margin, driven almost entirely by referrals and relationship-based sales targeting small to mid-market clients and marketing agencies needing technical implementation.

OneUp Repairs is a bootstrapped, profitable cell phone and computer repair shop operating two locations in Austin and San Marcos, Texas. Founded by John and joined by Erica Douglas in December 2014 with a $17,000 investment for 50% equity, the business grew from $62,000 in 2014 to $380,000 in 2015 and was on track to exceed $1 million in 2016. The company's growth has been driven by exceptional customer service, high-quality parts sourcing, and outstanding Yelp reviews (167 five-star reviews), making it Austin's highest-rated independent repair shop.

Alpha Rank is a data science SaaS company founded by 26-year-old Brian Lay that uses time-series analysis to infer network structures and identify influential customers for brands. Drawing from his background in epidemiology and observations of human behavior patterns, Brian created a tool that scores customer influence and predicts network lifetime value. As of 2016, the company had raised $500,000 from angels and VCs, was in private beta doing free case studies, and remained pre-revenue while building out the technology with a team of seven engineers.

Grandex is a media and e-commerce company founded in 2010 by Madison Wickham and a co-founder, starting as a simple one-liner comedy website called Total Frat Move (TFM) targeting college fraternity culture. The company grew from $2,000/month in ad revenue (August 2010) to $10M in annual revenue by 2015 through diversification into branded merchandise (Rowdy Gentlemen), premium retail curation (Man Outfitters), and expanded media properties. They raised $2.3M in angel funding at a $20M pre-money valuation around 2014, and now operate with 40+ employees using owned media channels to drive traffic to their e-commerce and advertising businesses.

Beate Chelette built an image licensing business focusing on architecture and interior photography that became the industry leader, eventually licensing celebrity content to 76 countries. She sold the business to Bill Gates' Corbis in 2006 for a significant multiple of the ~$1M revenue and has since pivoted to coaching creative entrepreneurs and women in business, building targeted email lists of 12,000+ and helping clients scale to six and seven-figure businesses.

Todd Tresetter is a hedge fund manager who retired at 35 and launched Financial Mentor (financialmentor.com) to teach unconventional investment and retirement planning strategies. Starting as a boutique coaching practice, the platform has grown significantly through word-of-mouth, with Todd now converting one-on-one coaching into scalable courses. The site offers free resources including an ebook and a 52-week financial freedom course to build community and provide value-based education.

ZynePak is a custom publication and VIP merchandise agency founded in 2011 by Kim Kaup that creates exclusive fan packages for entertainers, brands, and celebrities. Starting with $600,000 in revenue in 2011, the company grew to $2.8M by 2015 and appeared on Shark Tank, receiving offers from four out of five sharks (though ultimately declining to accept). They work with major artists like Justin Bieber, Shawn Mendes, Katy Perry, and sports teams like the Boston Red Sox and New York Mets, operating on a B2B wholesale model with 20-35% gross margins.

Khalid Salid founded InVesp in 2006, a conversion optimization consulting agency that helps enterprise clients like eBay, O'Reilly, 3M, and Dish Network increase online revenue. Starting with $15-20K in first year revenue while maintaining a $100K+ corporate salary, the company grew to over $1 million by 2011 through high-touch consulting ($8,000+/month retainers averaging 15-24 months). By 2016, Khalid decided to transition the business into a SaaS platform offering A/B testing, heatmaps, video recording, and analytics to compete in the conversion optimization software space.

Hourly Nerd is an online marketplace connecting elite business talent (MBAs, professors, industry experts) with companies needing specialized expertise on a project basis. Founded in 2013 by Rob Biedermann and two co-founders from Harvard Business School, the company takes a percentage (15-20%) of each project transaction and had grown to 21,000 experts serving 5,000+ customers including major clients like GE by 2015. With $10 million raised including a $750K seed from Mark Cuban and a $7.8M Series B, Hourly Nerd reached over $5M in ARR by 2015 with a 58-person Boston-based team.

Graham Williams co-founded Fun Fun Fun Fest in 2006 with Tim Leigh, growing it from a single-day event with 3,000 attendees and a $100k budget to a three-day festival attracting approximately 20,000 people with a $4-5M production budget. He also built Transmission Agency, a year-round booking and promotions company that operates across Texas. The business model generates revenue primarily through ticket sales (approximately $1-2M), sponsorships, and bar/beverage sales.