Positive Sum VC

High-Level Overview

Positive Sum is a venture capital firm that provides patient, long-term capital and deep operational support to early-stage companies, partnering closely with founders who are passionate about their life’s work. Their investment philosophy centers on creating *positive sum outcomes*—situations where companies, customers, and investors all benefit together. They focus on backing companies with unique products in large markets that demonstrate high-frequency, repeatable customer traction, aiming for compounding growth over decades. Positive Sum also helps founders tell their stories and connect with the right audiences through their sister company, Colossus, and offers access to a strong network of founders, operators, and investors[1][2].

Origin Story

Founded in 2020 and headquartered in Greenwich, Connecticut, Positive Sum was established by experienced partners including CEO Patrick O’Shaughnessy and President Alison Davis Riddell. The firm evolved with a focus on long-term partnerships and positive sum outcomes, emphasizing a patient capital approach. Their team brings over a decade of private equity and venture experience, primarily investing in technology, healthcare, and financial services sectors across North America and Europe. Positive Sum has executed more than 30 deals, leveraging a data-driven, operator-first investment style[3][5].

Core Differentiators

• Unique Investment Model: Patient, long-term capital with a focus on positive sum outcomes benefiting all stakeholders.
• Deep Involvement: Makes relatively few investments but is deeply involved with portfolio companies, supporting founders on lifelong quests.
• Network Strength: Provides access to a unique network of founders, operators, and investors, enhancing talent and partnership opportunities.
• Storytelling Support: Helps founders articulate and share their vision through their sister company, Colossus.
• Track Record: Over 30 deals with a focus on companies that strengthen as they grow, aiming for compounding returns over decades[1][3].

Role in the Broader Tech Landscape

Positive Sum rides the trend of long-term, founder-centric venture investing that values sustainable growth and alignment of interests among companies, customers, and investors. This approach is increasingly relevant as startups seek patient capital to build enduring businesses rather than quick exits. The firm’s focus on unconstrained markets with repeatable customer traction aligns with broader market forces favoring scalable, high-frequency business models. By supporting founders deeply and providing storytelling and network resources, Positive Sum influences the ecosystem by promoting durable company-building and positive-sum value creation[1][2].

Quick Take & Future Outlook

Looking ahead, Positive Sum is likely to continue emphasizing long-term partnerships with visionary founders, leveraging its unique network and storytelling capabilities to help portfolio companies scale sustainably. Trends such as increased demand for patient capital, founder-driven narratives, and positive-sum business models will shape their journey. Their influence may grow as more investors and startups seek alignment beyond financial returns, focusing on shared value creation and durable growth. Positive Sum’s commitment to deep involvement and positive sum outcomes positions it well to be a key player in shaping the future of venture capital[1][3].