Own Pain Startups

Yo Shirt is a mobile app enabling users to design and order custom on-demand apparel directly from their iOS device. Founded in 2014 by Ben Williamson (former senior-level Apple engineer), the company raised $1.1M in a priced equity round in early 2015 and reached $3M in revenue by end of 2015, with projections to hit $10M in 2016. Growth was driven primarily through strategic brand partnerships (notably Fallout Boy, which generated over 1,000 units in a single tour activation) and organic marketing including Apple App Store features.

Laurie Lane Zucker founded Impact Entrepreneur Center after 10+ years in social enterprise and impact investing to build an ecosystem for entrepreneurs focused on triple bottom line business (financial, social, and environmental returns). The organization operates as a LinkedIn-based network of 10,700+ members across 150+ countries and generates revenue through consulting engagements, success fees on funded deals (typically 5% of seed rounds), retainers, speaking engagements, and mentoring. Laurie is now scaling the model into a physical center combining incubation, acceleration, remote learning, and regional economic development initiatives in Massachusetts.

Doorman is an on-demand package delivery service founded by Xander Adel, a former Pixar technical director, that solves last-mile delivery problems by allowing customers to schedule package arrivals at convenient evening hours (6 PM to midnight). By 2016, the company had raised over $3 million, built a team of 10, and delivered over 100,000 packages across three markets (San Francisco, Chicago, and New York) with both direct-to-consumer and retail partnership models.

Pixie is an image optimization SaaS platform launched in 2014 by Holly Cardew that helps e-commerce merchants automatically edit and optimize product photos for multiple platforms within 24 hours. The company is self-funded with $150k in angel investment, operates with a distributed team of 16 (plus 100+ freelance designers), and is processing hundreds of thousands of images with over 7,000 customers. Holly grew the company to breakeven by 2015 and found the most explosive growth through an affiliate program that generated 1,000 signups and 70 paying customers in just three weeks.

Steve Sims is a luxury experience broker who has built an agency connecting high-net-worth entrepreneurs and self-made individuals with exclusive, once-in-a-lifetime experiences (meeting celebrities, private performances, etc.). Operating since at least 2015 with just under 3,000 clients worldwide, the business generated just under $10 million in revenue in 2015, operating with a lean team of 11-12 people. Steve's core differentiator is his credibility chain networking approach—leveraging relationships to gain access to otherwise unreachable people and opportunities.

Juice Land is a bootstrapped organic juice bar chain founded by Matt in Austin, Texas, with origins tracing back to 2001. As of 2015, the company operates 16 locations across Austin, Houston, and Brooklyn with $10M in annual revenue and 275 employees. Growth has been driven by word-of-mouth and location selection based on foot traffic observation, with a focus on premium organic ingredients and product consistency despite razor-thin net margins of approximately 5%.

Cool Leaf is a B2B SaaS platform that helps mid-sized businesses and Fortune 500 companies organize, communicate, and track employee engagement efforts. Founded in 2011 by Prem Bhatian and co-founder John, the company has evolved from an initial B2C focus to a successful B2B enterprise with 26 active customers paying an average of $25-30k annually. By March 2016, Cool Leaf had raised $800k in funding (including from 500 Startups), generated less than $500k in 2015 revenue, and was aiming to hit $1M ARR by end of 2016.

Glintz is a career discovery and talent marketplace founded in late 2013 by Chin-Un Luy that connects employers with young graduates and fresh talent in Singapore. The company grew from $7,000 in first-year revenue (2013-2014) to nearly $500,000 in 2015, achieving 15% month-over-month talent database growth while spending less than $1,000 per month on marketing, primarily through word-of-mouth and direct university partnerships.

Map My Fitness (Map My Ride, Map My Run, Map My Walk, Map My Hike) was founded in 2006 by Robin Thurston after a cycling trip in Switzerland. The company grew to 20 million monthly active users by 2013 through purely organic, word-of-mouth growth with no paid customer acquisition. At exit, the company had $17 million in trailing 12-month revenue across multiple business lines (advertising, subscriptions, and SaaS API licensing) and was acquired by Under Armour for approximately $150 million.

John Bowen is a serial entrepreneur who built and sold multiple financial services businesses, including a $2 billion advisory firm and a company taken public on the Canadian market. He now runs CEG Worldwide, which coaches top financial advisors through a subscription model, and co-founded AESNation.com with thought leaders like Dan Sullivan and Joe Polish to research and educate entrepreneurs on wealth creation and best practices.

Gift Starter is a consumer crowdfunding platform that allows people to break down expensive online purchases into affordable chunks that friends and family can co-purchase as gifts. Founded by Aerie Ewen in July 2014 after winning a hackathon, the company pivoted from a B2B e-commerce plugin model to a consumer-facing payments platform, raising $525,000 in angel capital and achieving $12K revenue in 2015 with plans to reach $50K in 2016.

Bounce Exchange is a behavioral automation software company that helps e-commerce and publisher sites increase conversion rates by reacting to users' digital body language. Founded by Ryan Urban in 2012, the company grew to $17M in 2015 revenue with a run rate goal of $40M by end of 2016, serving 250-300 paying customers across ~700 websites. The company eschewed traditional VC-funded growth models, staying mostly inbound, hiring minimal sales staff, and maintaining nearly break-even profitability while scaling.

Jefferson Lilly co-founded Park Street Partners in 2013 after spending 7 years personally investing in mobile home parks, discovering 20-40% cash-on-cash returns far exceeded traditional real estate. By 2016, he had raised a $5 million fund and personally owned 11 mobile home park communities generating over $100,000 in annual cash flow from his two Oklahoma properties, positioning himself as an industry educator and expert.

Haz Design is a product design agency founded by Tracy Hazard and her husband Tom that has co-designed over 250 consumer products generating over $1 billion in retail sales. Their flagship product, an office chair launched in Costco around 2010, has sold over 1 million units and generated approximately $1 million in combined fees and royalties. The business operates on a retainer-plus-royalty model, with monthly fees ($10,000-$20,000) covering costs and 2-3% royalties on product sales, achieving an 86% success rate for products launched in the last 10 years.

Steals.com is a daily deal e-commerce marketplace founded by Jaina Francis in 2008 that features one high-quality brand per day across four niche sites (BabySteals, KidSteals, ScrapbookSteals, SheSteals). Built entirely bootstrapped without investors, the company generates approximately $8 million in annual revenue with a 17% net margin, driven primarily by email marketing (55% of revenue) and direct traffic (25%). With 22 full-time employees in Utah and a custom-built platform, Jaina is seeking $2 million in equity funding at an $8 million pre-money valuation to fuel growth.

Jason Hartman is a serial entrepreneur and real estate investor who has built a media empire around podcasting, most notably The Creating Wealth Show, which has over 640 episodes and reaches listeners in 164 countries with approximately 5,000 downloads per episode. His primary revenue comes from his real estate investment company that helps clients invest in properties, generating approximately $2.4 million in referral fees from managing around 500 properties annually. He leverages his popular podcast as a marketing tool to drive attendance at Jason Hartman University events and promote his real estate investment services.

Combat Flip Flops is a social impact e-commerce business founded in January 2012 by veteran Matt Griffin and co-founders Donald Lee and Andy that manufactures and sells tactical lifestyle products (flip-flops, shemas, cashmere wraps) made by entrepreneurs in conflict areas like Afghanistan. The company grew from $5,000 initial investment to $300,000+ in 2015 sales and $400,000+ in early 2016, with a goal of $1.4M annually, while donating 10% of margins to women's education in Afghanistan. Growth was driven through strategic media relations with military/tactical blogs, a simple e-commerce website, Facebook affiliate marketing, and a compelling veteran-led mission.

Joe Fairless left a $150k+ VP role at a NYC ad agency in 2013 to pursue real estate syndication after an initial consulting business failed. He acquired his first 168-unit apartment complex for $6.3M in July 2013, raising $1.3M from investors. Since then, he has scaled to 250+ units and launched a daily real estate podcast (120k monthly downloads as of Feb 2016) that generates ~$2-3k/month in net sponsorship revenue and has raised over $800k from podcast listeners.

Michael Slavin built US Emerald Energy, an oil and gas exploration company that brings investors into drilling partnerships, after recovering from bankruptcy post-military service. Starting with $203,000 raised from four people (including a stranger met at a gas station) in his first week and a half, he grew the company to $1 million in profit within 3.5 years. The company has operated for over 23 years, maintaining an 85-90% success rate on wells by focusing on PUD (Proved Undeveloped) reserves with 3D seismic data, and profiting from both investor management fees (20%) and direct well ownership stakes.

Molly Marie Kaiser is a serial entrepreneur who bootstrapped her way from $50,000 in debt to building multiple six-figure businesses. Her most recent venture, Venture Shorts, is an online info product platform that teaches creative entrepreneurs how to build their own knowledge-based businesses, generating just over six figures in its first year through course sales and eBooks.