Own Pain Startups

Angelo Ramora built Ohio Cash Flow, a real estate investment company that buys distressed properties, renovates them, tenants them, and sells them to passive investors across the US, UK, Canada, and Australia. Starting from a failed highly-leveraged approach at age 23 that lost $3-4k monthly, he pivoted to cash-flow focused investing and scaled to 7 closed deals generating $210k in profit by January 2016, with a goal of 250+ deals that year. The company operates two offices with 10 full-time staff and provides end-to-end property management services to investors seeking passive real estate income.

Project Repat turns customers' old t-shirts into quilts made in the USA with recycled plastic bottle fleece. Starting with just $25k in seed funding and $8k in the bank, Nathan Rothstein and his co-founder scaled from struggling with a Groupon viral moment in August 2012 (selling 2,000 quilts in a week) to $750k in revenue by November 2015. They aggressively scaled through Facebook ads and email marketing (Klaviyo), reinvesting heavily into customer acquisition to dominate the blue ocean market of affordable t-shirt quilts.

Gusto is a SaaS platform helping small businesses manage payroll, HR, benefits, and health insurance. Founded by Josh Reeves (who previously co-founded Unwrap, acquired in 2010), Gusto has grown to over 25,000 paid customers with a 98% conversion rate from free trial to paid status, serving companies with 1-100 employees at $29/month plus $6 per employee.

Lila Zimmerman is a 19-year-old University of Maryland sophomore who built Fresh Fit and Fearless, a content-driven lifestyle brand centered on plant-based vegan eating. She grew her Instagram account from zero to nearly 15,000 followers in approximately one year (with serious effort starting at 6 months) through consistent quality content, strategic hashtags, and share-for-share partnerships. Her monetization strategy includes a $14.99 recipe e-book that has generated approximately $900 in sales, plus sponsored posts ($100 per two posts) and free product partnerships from 20-30 companies monthly.

Kristi Zouki left a six-figure salary at Procter & Gamble to found Knowledge Hound, a SaaS platform that solves 'corporate amnesia' by making companies' market research searchable and discoverable. The platform had grown with double-digit growth rates for three years by 2016, with a goal to hit $5 million in annual revenue by the end of that year.

Sue Zimmerman built a multi-million dollar business selling online Instagram marketing courses and coaching services. Her flagship "Insta Results" course priced at $997 generated approximately $67,000 from 67 sales in one year, though total course revenue exceeded $300,000+ when including her lower-priced offerings. Her primary growth channels were speaking engagements, podcast interviews, and strategic email list building (4,900 subscribers from a single strategy guide funnel), focusing on relationship building before conversion.

SoundBetter is a two-person marketplace connecting self-producing musicians with freelance audio professionals (including Grammy winners) to help them complete professional-quality songs. As of June 2015, the company achieved an $800k annual run rate through a two-sided commission model: freelancers pay $4 per proposal and 5% of completed job value. Their primary growth driver is organic search traffic, bringing in approximately 30,000 unique monthly visitors searching for audio production services.

Jamie Turner is the CEO of 60 Second Communications, a full-service marketing agency that has helped major brands like Coca-Cola and AT&T with complex marketing problems. He built thought leadership through his blog 60 Second Marketer and speaking engagements, starting with free university gigs 15 years ago and eventually commanding $5,000+ per speaking engagement. Speaking now comprises approximately 25% of his annual revenue, which exceeds $100,000 per year from speaking alone.

Franklin Cole is a sales funnel architect and advertising strategist who helps high-revenue entrepreneurs ($10M+) scale their businesses through strategic Facebook advertising and funnel optimization. He generates revenue through monthly retainers plus performance-based compensation, and has driven over $40 million in combined client revenue by spending $3-3.5 million on ad campaigns—demonstrating a 12x+ ROI. His approach focuses on mapping profitability paths before spending any money and optimizing for revenue-per-lead metrics.

The Art of Charm is a personal development school and podcast network founded by Jordan Harbinger, a former Wall Street lawyer. The company operates a residential 5-day in-person training program in LA teaching advanced social skills and networking to military special forces, intelligence agents, and high-end sales professionals, charging $6,000-$8,000 per person. With 2 million monthly podcast downloads and a wait list booked 6 months in advance (serving 8 clients per week at ~$64k weekly revenue from live programs alone), plus seven-figure revenue streams from podcast advertising and online courses, The Art of Charm has grown into a multi-seven-figure business over 8.5 years.

Hand Ground is a premium manual coffee grinder co-founded by Daniel Vitello that raised $309,000 in pre-sales on Kickstarter in 30 days through a strategic pre-launch campaign. The company built an Instagram following of 5,000 people before launch, then executed a viral referral campaign in December that leveraged direct messaging and a lottery-style rewards system to drive email signups. Post-Kickstarter, Hand Ground continues to generate daily sales through a link embedded on their Kickstarter page, while focusing on product development and manufacturing partnerships in China.

Carrie Wilkerson launched The Barefoot Executive in August 2007 as an online brand built on conducting interviews with influential business leaders, positioning herself as an expert by funneling information rather than creating it. Within 4-5 months, she received an inbound call from a corporate direct selling company offering her $2,000 to deliver a 60-minute keynote speech, marking the start of her lucrative speaking career. Between 2007 and 2014, her keynoting and associated revenue streams (book deals, audience contracts, consulting) generated well over $1 million, while she maintained work-life balance by working strategically around her four children's schedules.

Flourish and Thrive Academy is an online education platform founded by Tracy Matthews, a jewelry designer with 20+ years of industry experience. After her first jewelry brand failed despite nearly $1 million in sales due to poor business structure, she built an academy to teach emerging jewelry designers business skills, marketing, and operations. The academy has grown to 800 students in three years using a Facebook ad-driven funnel ($500/month spend generating ~1,000 monthly opt-ins) and webinar-based sales, with both one-time courses ($795 generating $160,000 from 245 signups) and newly launched subscription offerings ($49-$78/month).

Ben Uyeda is an architect and designer who founded Zero Energy Design in 2006 and has built a real estate development practice by combining creative design with financial engineering. His flagship Boston project involved acquiring a $100k empty lot zoned for two units, negotiating a zoning variance with the city to build three units through sustainable design proposals, and creating innovative one-bedroom loft-style apartments tailored to Boston's young professional demographic—resulting in units selling for around $500k.

GoPro was founded by Nick Woodman, a surfer who created the camera to capture first-person action footage from his own adventures. Working with marketing strategist Ron Lynch, GoPro employed an innovative TV advertising strategy using cheap remnant time slots ($100-$500 per 30-second spot) on niche sports channels, paired with a contest mechanism that drove users to gopro.com for data capture. This approach generated a 2.5x media efficiency ratio, ultimately scaling the company from $600k in annual revenue to $500M+ in just five years, eventually reaching a $7.8B market cap at IPO.

Mizzen+Main is a performance fabric dress shirt brand founded by Kevin Lovell in July 2012. Starting with 20 shirts sold on day one to friends and family, the company has grown 4-5x year-over-year and sold 100,000+ units. The company commits to American manufacturing and employs veterans, maintaining premium positioning by never discounting products.

Kevin Wilkie's Nitro Marketing generates over $4 million annually by teaching people how to start local marketing consulting businesses. He uses a sophisticated webinar funnel that generates 30% of sales during the live event and 70% through replays and recordings, with a recent webinar converting 398 attendees into 170 sales ($126,000). His growth is driven by affiliate partnerships that promote the webinars to their audiences in exchange for 50% commission on sales.

The Foundation is a 6-month SaaS education program founded by Dane Maxwell that teaches aspiring entrepreneurs how to build lucrative software companies from scratch. With approximately 1,400 students trained over four years and total revenue between $5-6 million, the program focuses on integrating emotional, logical, and physical development alongside business fundamentals. While less than 10% of students graduate with 10 paying customers within six months, 40% launch with at least one paying customer, and the program maintains an impressive 8/10 Net Promoter Score.

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.

Funded Today is a crowdfunding agency co-founded by Zach Smith that has raised over $40 million for 300+ campaigns on Kickstarter and Indiegogo. The company started when Zach's consulting client proposed paying via revenue share instead of upfront fees, which evolved into a three-tiered service offering paid media, press landing, and cross-collaborations. With 31 remote employees and $8M in 2015 revenue, Funded Today takes a 30-35% percentage of funds raised and operates with a unique due diligence testing phase to predict campaign success.