Dropbox Startups

Patriot Chimney is a Virginia-based chimney and dryer cleaning, repair, and building company launched in August 2018 by three co-owners (Mitchell Blackmon, Matt Blackmon, and Billy). Starting with just $12,000 in their first month through door hangers and online platforms, they grew to 350 clients, 5 employees, and $212,000 in revenue through a combination of offline marketing (door hangers, postcards, door-to-door sales) and digital channels (SEO, Google Ads, Facebook, Yelp, referrals, and word of mouth).

Ziglar Corporation, led by Tom Ziglar, is a legacy personal development and training company that has modernized its distribution through digital channels. The company offers a $7,500 five-day Ziglar Legacy Certification course and generates significant traction through 4 million Facebook fans, 400,000-500,000 unique weekly visitors to the Ziglar Vault content hub, and a top-100 US podcast with 35,000+ downloads per episode, adding 3,000-5,000 email subscribers weekly.

Mailbird is a desktop email client and unified communication tool built by CEO Andrea Lubier, based in Bali, Indonesia. Launched in 2012, the company has grown to manage over 1 million email accounts with approximately 500,000 paying customers and $500,000 in annual recurring revenue. The business uses a freemium model with lifetime purchase and annual subscription options, leveraging flash sales and smart pricing structure to achieve 20% conversion rates on their website.

Code 42 is an enterprise data loss prevention and insider threat detection platform that helps organizations prevent employees and contractors from exfiltrating sensitive data. The company achieved $50M ARR after spinning out from its parent company (which sold the legacy CrashPlan product for $250M to private equity), and now serves 800+ customers including major security firms like CrowdStrike, Okta, and Splunk with pricing around $80-120 per employee per year. Founded within another company in 2015 and launched in 2017, Code 42 targets mid-market enterprises (1,000-5,000 employees) through intent-based sales and has several customers paying over $1M annually.

Hurdler is a free mobile app founded in 2012 by Raj Paskar that helps independent workers (Uber drivers, Airbnb hosts, freelancers, real estate agents) manage their business finances in real time with an automated tax calculation engine. The company grew to over 100,000 users primarily through content marketing—creating high-value resources like tax deduction guides and then distributing them through community relationships. Revenue comes from value-added services like H&R Block tax filing partnerships and an API consumed by other financial institutions.

People.ai is an enterprise SaaS platform that uses AI to help sales teams capture all their activities and provide actionable insights. Founded by Oleg Roginski (who previously bootstrapped and sold Cementria, a sentiment analysis API, for $5M ARR), People.ai achieved ~100 logos in 45 days before Y Combinator demo day through intensive customer development and outbound sales, eventually moving upmarket to work with large enterprises and public companies.