Own Pain Startups

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.

Gimlet Media is a premium podcast network founded by Alex Bloomberg, a veteran of This American Life and Planet Money. The company produces high-quality narrative audio shows including Startup, Reply All, Mystery Show, Science Versus, and Surprisingly Awesome, generating over $1 million in annual ad revenue per show through CPM-based sponsorships well above industry standards ($50+ CPM vs. industry average of $20-30).

Tom Hunt is a 26-year-old founder who left his job at Accenture in 2015 to launch Virtual Valley, a marketplace connecting entrepreneurs with vetted virtual assistants from the Philippines. The platform charges a 20% markup on assistant salaries ($500-$1,000/month per assistant) and offers recruitment, payment escrow, and time-tracking software. Tom projects $7,000 MRR by February 2016 and aims to build to $15,000 MRR by year-end, with a long-term goal of selling the company for $4 million.

SeamlessDocs is a SaaS platform that transforms static PDFs into smart, interactive online forms for government and enterprise clients. Founded in 2013 by Jonathan Endin, the company struggled for the first year trying to serve small businesses before pivoting to local and state governments as their ideal customer. With over 300+ government customers across 40 states, a 99% annual retention rate, and $17,000 average annual contract value, they were projected to reach $2M in 2015 revenue and $20M in 2016.

Mark Gunye is a serial entrepreneur who operates two businesses: Gunye Tumie Inc., a family-run electronics components sales organization processing $2-4 million monthly in transaction volume with 2-5% margins, and Bridge Equity Group, a real estate fix-and-flip and multi-family acquisition business in Northern California. He generates approximately $100-200K+ profit per real estate deal (averaging 6 deals annually) by identifying undervalued properties through MLS listings, agents, and wholesalers, then adding value through renovations and strategic improvements before resale.

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.

Michael Devlin launched Profits Engine, a membership platform combining e-commerce software tools with education for Amazon sellers. He generated approximately $110,000 in upfront revenue from 104 customers through a single webinar to his LinkedIn network (10.5k followers), with customers paying $997 for the Amazoners Academy course and upgrading to recurring subscriptions ($99-$199/month) for the Profits Engine software and tools.

Liz Piccarazzi left a six-figure job at American Express to launch Checklist Home Services in 2011, a professionally-run handyman service in Brooklyn and Queens that prioritizes customer experience. Completing 65 jobs in October at an average price of $400 per job with net profit of $60-$75 per job, the business operates with W2 employees rather than 1099 contractors and has expanded into a second venture, Citibin.

Batchbook is a SaaS CRM platform founded by Pam O'Hara in 2006 to help small businesses manage customer relationships. The company bootstrapped to over 10,000 paying customers with an average monthly spend of $42 per customer and above 95% retention rates, using word-of-mouth and targeted paid social as primary growth channels.

Kimra Luna launched Be True Brand U, a $2,000 digital course program, in May 2014 and generated $880,000 in first-year revenue (May 2014-February 2015) through a combination of Facebook ads and webinars. She grew her email list from 5,000 to 10,000+ people and built a 20,000-member Facebook community, using a strategy of list-building with a free mini course, retargeting existing audience members through webinars, and aggressive email campaigns on launch closing days.

Stig Broderson left a six-figure commodities trading career in 2011 to pursue teaching and creating The Investors Podcast, inspired by Warren Buffett's philosophy of living authentically. Co-hosted with a friend in Maryland, the podcast has become the number one podcast in the world in stock investing, ranking #1 in its category with 17 competitors tracked. The show operates on a free model with no monetization yet, as Stig focuses on building value and maintaining editorial integrity.

Sellbreaker is a legal-tech SaaS platform founded by John Colgan that helps consumers cancel cell phone contracts without paying early termination fees by identifying carrier breaches in contracts. The company charges 35% of the savings (ETF amounts) and achieved a $13 million annual run rate by August 2015 with 13,000 users, maintaining a 100% success rate. Colgan raised just under $300,000 in convertible notes (partly from 500 Startups) and planned to expand to other consumer contracts under a new vertical-agnostic brand called Vito.

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.

Chad Whitman is a serial entrepreneur who first built Edranck Checker, a Facebook analytics tool that grew to $60K MRR before selling to Social Bakers for approximately $2.8M in 2014. He then co-founded Dolly, an on-demand moving marketplace that leverages pickup truck owners as a unique asset class, raising $1.7M seed and $8M Series A (valuation ~$50M range) by taking a 20% cut of jobs on the platform.

Justin and Tara Williams built 8 Minute Millionaire, an education platform teaching real estate investment and business building, after achieving $4.5 million in net real estate profits over four years. Their online education business, launched two years prior to this interview, rapidly accelerated in the last three months with $85,000, $125,000, and then $500,000 in revenue from newly launched high-end coaching programs ($25,000 per program with 20 slots). They leverage their podcast and existing audience to drive growth while maintaining time efficiency through delegation.

Dory Clark is a bestselling author, keynote speaker, and business consultant who successfully diversified her revenue from consulting into a multi-stream business including book sales, speaking engagements, and coaching. Starting with her first paid speaking gig of $5,000 in 2013 for her book 'Reinventing You,' she scaled to delivering 59-61 talks annually and generating $125,000-$150,000 from speaking alone in 2015, while her books have sold over 30,000 copies (Reinventing You) and 6,000+ copies (Stand Out) within months of launch.

Billy Murphy built Forever Jobless into a content platform with 96,000 Instagram followers by organizing shout-for-shout cross-promotion groups and direct outreach to influencers. He converted his Instagram audience into a 26,000-person email list and launched an Instagram course at $397 one-time payment, generating $20,000-$30,000 in revenue in August alone. His strategy demonstrates how organic Instagram growth through peer promotion can be significantly more cost-effective than paid advertising.

Due is an online invoicing and time-tracking platform founded by Murray Newlands that helps freelancers and small businesses manage invoices and get paid. After just three months, the company had 75,000 registered users with over 500 paying customers, primarily acquired through content marketing including a 7,000-word freelancer guide and strategic media placements on Entrepreneur, TechCrunch, and Time. The team is bootstrapped, self-funded, and focused on building partnerships and differentiating features before a full market launch.

Scott Gerber founded the Young Entrepreneurial Council (YEC), an invitation-only membership organization with 1,600+ vetted entrepreneurs from companies collectively generating $13 billion in revenue with $9 billion in venture capital backing. The organization maintains exceptional 90%+ annual retention by focusing on highly personalized, human-centric member experiences including curated networking, quarterly check-ins, and proactive value delivery rather than growth-hacking metrics.

Neville Medhora built CopywritingCourse.com to teach email copywriting after discovering its transformative power while running HouseOfRave.com, an e-commerce business. His first compelling email generated 120 orders in two hours from a list of 7,500 people, convincing him of copywriting's ROI. Today, CopywritingCourse.com has grown to 21,000 email subscribers, with Neville focused on list-building as his primary growth lever.