Own Pain Startups

ShipHawk is a transportation management system and fulfillment software for mid-market e-commerce retailers, manufacturers, and distributors (typically $10M-$500M ARR). Launched in 2013, the company has grown to serve 300+ paying customers including Grove Collaborative, achieving negative 15% net revenue churn and over 100% year-over-year growth. The company raised $12.5M in capital and generated south of $8.4M in ARR as of 2017, with most customer acquisition driven through platform partnerships with mid-market ERPs.

Cloudflare, founded by Matthew Prince in 2010, built a global content delivery and security network spanning nearly 100 countries that now handles over 10 trillion requests per month from 2.5 billion people. The company achieved $50M ARR in 4.5 years (by 2015) and has grown to north of $100M annually with 50-100% YoY growth, powered primarily by word-of-mouth and inbound marketing with extremely low customer acquisition costs ($1.3M ACV for enterprise sales teams).

AppDirect is a cloud commerce platform founded in 2009 and officially launched in 2011 by Dan Sax and a co-founder, enabling businesses to find, buy, and use cloud services through a marketplace ecosystem. The company started with Bell Canada as their first customer and has scaled to over 650 employees and 35 million customers (across their customer network), raising $245 million in venture funding. Their platform generates revenue through platform fees and transaction fees, with customers ranging from a few thousand dollars monthly to hundreds of thousands for complex deployments, and they've achieved net dollar retention above 100% across customer cohorts.

Elizabeth Ozder runs a 10-year-old consulting firm (The Ozder Group) specializing in media strategy and digital transformation, while also serving as head of revenue at LaCona, a content management platform powering 150 million unique monthly users across 60% of local markets. She advises legacy media brands and publishers on navigating the shift from scale-based ad models to subscription and engaged audience models, with clients including AOL, Univision, Associated Press, and others.

Predict Leads is a B2B SaaS company providing competitive intelligence and business data via API to VCs, corporate VCs, and sales enablement platforms. Founded in 2015 by Rox Seever and co-founders in Slovenia, the company crawls billions of data points to extract signals about new partnerships, client acquisitions, and hiring intent. Growing from ~$40-50K ARR in 2017 to ~$325K ARR in 2018 (at the time of interview), the company has 30 customers paying an average of $12K annually, bootstrapped with only $15K from an accelerator.

Seaforge (platform: Fatfinger) is a no-code app builder for frontline workers in heavy industry, launched in 2011 and bootstrapped before raising $1.5M. The company serves ~50 customer logos with hundreds to thousands of total seats, growing through a bottom-up product-led strategy where frontline employees build apps that then get adopted company-wide. With 9 team members, 200-300% net revenue retention, and charging ~$9 per seat, James McDonough has kept the company lean and focused on organic growth and customer success rather than aggressive sales.

TransferWise launched in January 2011 after founder Tavit Hinrikus experienced expensive international money transfers while working at Skype. The company got its first customer (sending 2000 pounds) within 15 minutes of a TechCrunch article and grew to 4 million users processing $3.9-4 billion monthly by 2018. TransferWise achieved profitability while scaling globally, expanding into borderless accounts and debit cards to disrupt traditional banking.

Encompass Corporation, founded in 2012 by Wayne Johnson, is a RegTech SaaS platform that automates Know Your Customer (KYC) compliance and due diligence for legal, accounting, and banking sectors. The company grew to 250 customers across London, Glasgow, and Sydney offices, generating south of $1M monthly revenue with 34% quarterly growth, 3% annual revenue churn, and strong unit economics ($75k CAC, 15-21 month payback). Growth is driven primarily by direct sales and increasingly by channel partnerships with revenue-sharing agreements.

Grossumo is a SaaS platform that helps enterprises like Intuit, Asana, and Buffer manage their reseller and channel partner networks at scale. Founded in 2015 by Luke Swanak and co-founders Bryn Neal and John Neal, the company charges a base fee (averaging $1,500-$3,500/month) plus performance-based fees tied to partner-driven revenue. Growing 25-35% month-over-month with ~200 customers, less than 2% logo churn, and a team of 20 based in Toronto, Grossumo has raised over $1M in capital and operates with capital-efficient, humble growth principles.

Oramed Pharmaceuticals, founded in 2006 by Ndave Kydron, developed proprietary technology to deliver insulin orally rather than through injections, targeting the massive diabetes market. The company went public on NASDAQ in 2013 pre-revenue and secured a major partnership with a Chinese pharmaceutical firm that paid $50 million ($12M investment + $38M licensing deal) while conducting FDA trials for approval.

WatchIt is an enterprise video creation platform launched in 2012 that combines automation, creative tools, and licensed content to help brands and publishers create short-form videos in minutes. Founded by George Ginsberg, the company has raised $29M and serves over 200 enterprise clients with minimum first-year ACV of $50k and lifetime value of $300k+, achieving healthy sub-6-month payback periods through content marketing and direct sales.

Zuberance is an SaaS platform for advocate marketing that helps brands activate their existing customers to become brand advocates. Founded by Rob Fugetta in 2008 after his decade at Apple, the company has worked with 250+ brands including Intuit, Lyft, and Nido Robotics, with 100+ brands paying monthly subscriptions averaging $10k-$20k per month. The company generates over $1M in monthly revenue with 80% annual retention and a 6-month payback period.

Volio is a social trading platform that enables groups of friends, family, and colleagues to invest together while splitting trading fees. Founded by Thomas Beatty, a recovering investment banker, the platform addresses barriers to entry by lowering costs, enabling diversification, and leveraging collective intelligence. After raising $5 million and launching soft in March of last year, Volio has attracted hundreds of real-money users and is now expanding into crypto and exploring white-label partnerships with credit unions and community banks.

BioWave is a medical device company founded by Brad Smith in 2007 that uses electrical signal technology to provide FDA-cleared, non-opioid pain relief. The company sells professional-grade devices ($3,500) to sports teams and hospitals, consumer home units ($895), and recurring revenue through disposable gel pads ($15 per pair) and high-margin percutaneous needle electrodes ($150 per pair). With 16 employees, 90+ pro sports teams as customers, presence in 34 VA hospitals, and a growing network of 70+ distributors, BioWave is projected to cross $5 million in annual revenue.

Lucky Orange is a SaaS conversion optimization suite founded in 2014 by Danny Weitzman and Brian Gruber that helps websites track visitor behavior and improve conversion rates. The bootstrapped Kansas City-based company serves 15,000+ paying customers across diverse verticals with a diversified revenue model where partnerships account for approximately 40% of revenue. Growing 80-100% annually with 3% monthly logo churn and a healthy two-month CAC payback period, Lucky Orange demonstrates sustainable unit economics despite being deliberately lean at nine team members.

ChatMeter is an online reputation and local SEO SaaS platform founded in 2009 by Colin Holmes that helps large multi-location businesses manage their presence and reputation across review sites like Google Maps and Yelp. After bootstrapping to $2M ARR in the first 4-5 years with less than $100k in initial funding, the company pivoted to enterprise-focused deals and has grown to approximately $10M ARR with 90% annual retention. The company serves hundreds of enterprise brands managing hundreds of thousands of individual locations across the country.

LogicBay is a partner relationship management (PRM) software company founded in 2003 by John Panna Chone, built from a spun-out US government contract worth $3M that couldn't transfer to an acquiring company. After 15 years of bootstrapping and selective fundraising ($2.5M equity, $3M debt), the company serves ~60 customers with 99% renewal rates, 5% annual logo churn, and generates $10-15M ARR with 10-15% YoY growth. The business focuses on wallet expansion within existing Fortune 500 customers rather than new account acquisition, achieving 90%+ net revenue retention and profitability at 10% EBITDA.

Zendesk is a customer service platform that revolutionized the industry by making complex support software simple and accessible. Founded in 2007, it grew to over 2,000 employees across multiple offices globally, achieving profitability through a product-led growth model that attracted 10,000 customers without a sales team before IPO in 2015. The company continues to expand through acquisitions like Outbound and internal innovations like Answer Bot, focusing on increasing wallet share with existing customers while moving upmarket and exploring new buyer groups.

Best Food Trucks is a marketplace platform helping food truck operators book premium locations and enabling consumers to order ahead while reducing wait times. Founded by Kevin Davis (who previously sold GeekAtoo for $20M in 2016) after merging with his co-founder's existing food truck booking platform, the company has 1,000 trucks across 10 cities and processed $1M in transactions in 2017. The business operates on multiple revenue streams: lot booking fees ($5 per $50 transaction), SaaS subscriptions for truck operators ($149/month), and convenience fees for customers.

ShareThrough, founded by Dan Greenberg in 2008, is a SaaS platform that powers in-feed native advertising for major publishers like Rolling Stone, Vice, ABC News, and Disney. The company charges on a SaaS model (CPM-based at 25-50 cents per thousand impressions) plus a revenue share on programmatic ad spend. With 200 employees, 1,200 publisher customers, and processing approximately $250 million in annual gross ad spend, ShareThrough has raised $30 million and generates $25+ million in annual revenue, positioning itself as an alternative to the Google-Facebook duopoly in digital advertising.