Dutchess Opportunity Fund II
50 Commonwealth Avenue, Suite 2, Boston, MA, 02116, United States
Overview
Since 1996, Dutchess has managed over $2 billion in transactional value for companies which span a wide array of sectors. With offices in Boston, New York, London, Beijing and Sao Paulo, Dutchess invests in global investment opportunities. For more than a decade Dutchess has been a global leader in Equity Line Facilities ("ELF") and has transacted in excess of $1.8 billion in such financings. The ELF is a flexible financing structure by which publicly traded companies can raise capital quickly and more efficiently than most traditional offerings.
- Total investments
- 2
- Lead investments
- 1
- Investments · 12mo
- 1
- Active investors
- 0
Sector focus
- Venture Capital
Investment portfolio
- Chowbus
Participated · Equity · Mar 2026
Founded in 2016, Chowbus offers a full-stack restaurant operating system that combines cloud-based POS, analytics, and AI-driven marketing solutions tailored to independent, culturally focused eateries. Its first AI product, AI Digital Ads, helps restaurants run targeted campaigns, and the company is now adding AI modules for automated accounting, supply ordering, insurance, and other back-office functions. Chowbus supports thousands of restaurants across all 50 U.S. states and Canada, processing roughly $4 billion in annualized transaction volume. The business currently generates more than $120 million in Annual Recurring Revenue—representing 9× growth over the past four years—and positions itself as a mission-critical partner rather than just a software vendor. Management plans to deepen its service integration, reduce operator overhead, and expand further into Canada. By leveraging AI to deliver 10× efficiency gains versus traditional solutions, Chowbus aims to help independent restaurants compete with large chains. The company’s strategy centers on becoming the comprehensive operating system for the $240 billion Asian restaurant segment and adjacent culturally rooted markets.
- MassRoots
Led · Equity · Mar 2014
MassRoots is a private social network serving the legalized cannabis community, offering a semi-anonymous environment for users to share cannabis-related experiences, connect with other consumers, and discover cannabis content. Since launching in July 2013, the app has grown rapidly, reporting 80,000 monthly active users, 14 million interactions, and more than 50,000 daily app opens. The platform emphasizes user privacy by not requiring personally identifiable information and targets users who prefer not to post cannabis activity on mainstream networks. MassRoots positions itself as a marketing and distribution channel for legalized cannabis and ancillary products, aiming to integrate mobile technology with the growing legalized cannabis industry. The company is building a location-based service to connect users with the cannabis community around them. Management describes the network as the premier digital hub for legalized cannabis users. MassRoots is an app-based social network dedicated to the medical cannabis community, launched in July 2013 and co-founded by Isaac Dietrich. The platform centers on high-quality cannabis content and aims to connect marijuana consumers while supporting the legalization movement. It does not require a user’s name, email or phone number to join, providing privacy and anonymity. The company says it seeks to build a marketing and distribution channel for legal cannabis and to empower the legalization movement. MassRoots closed $150K in seed funding from members of the ArcView Group and is using the funds for user adoption. The company is continuing to raise capital.
Team
No current team members are available.