Figure Eight Investments Research Document
Overview
Figure Eight Investments is an impact-oriented family office founded in 2017 by Diana Anthony and Kaushik Chakravarti, headquartered in Boulder, Colorado, with the leadership team recently relocating to Western North Carolina. The fund operates as a marriage of pedagogical expertise and entrepreneurial/venture capital experience, deploying capital in the $50K-$500K range across carefully selected sectors aligned with systemic impact.
Investment Thesis
Figure Eight Investments is driven by a coherent, values-aligned thesis focused on catalyzing systemic change through investments in three interconnected impact sectors: inclusive education, healthcare accessibility, and climate solutions linked to social mobility. Their fundamental belief is that investment capital can be a powerful tool for systemic change when deployed with intentionality around expanding accessibility, reducing costs of essential services, breaking down geographic barriers, and building sustainable long-term systems.
The fund's thesis is unique in its explicit commitment to a "virtuous cycle" model: Diana and Kaushik commit 10% of all investment profits to evidence-based nonprofits, creating a dual-impact mechanism where financial returns fund social impact work directly.
Founders and Team
Diana Anthony, Managing Partner / Co-Founder
- Former Montessori educator with deep experience in pedagogical philosophy and practice
- Taught in the US, UK, and Switzerland, bringing global perspective to impact investing
- MA in Literacy Learning from University College London
- Fulbright Teaching Scholar
- AMI Montessori diploma
- Brings strategic insight in education technology, student wellbeing, and experiential learning
- LinkedIn: https://www.linkedin.com/in/diana-anthony-600930154/
Kaushik Chakravarti, Partner / Co-Founder
- Twice-exited entrepreneur with deep operations and venture experience
- Currently CEO of CFI, an agricultural input financing platform
- Former investor in renewables and healthcare spinouts at PUK Ventures (British Treasury-backed VC)
- Founded and successfully exited two companies in the automobile and telecom sectors
- Strong expertise in climate solutions, agricultural innovation, and operational support
- LinkedIn: https://www.linkedin.com/in/kaushik-chakravarti-4296b37/
The structure is explicitly partnership-based, with both founders equally involved in decision-making and portfolio support. The fund emphasizes being "admin light and swift executors" with direct access to decision makers—founders work directly with Diana and Kaushik, not with junior investment professionals.
Sector Focus and Thesis Breakdown
Education (Core Pillar)
Figure Eight invests across three education sub-themes:
Employable Skills & Career Pathways
- Focus on products that open doors in founders' lives and reinvigorate the economy
- Portfolio includes Signal Vine (higher-ed text messaging), Pathful/Nepris (career exposure platform), and BitClass (independent live class management for teachers)
Experiential Learning & Pedagogy
- Immersive pedagogy that connects practice and instruction, providing safe spaces for simulated experience
- Portfolio company Mursion exemplifies this (virtual environment for professionals to practice complex interpersonal skills)
- Strong alignment with Diana's Montessori background and teaching experience
Student Wellbeing
- Tools and services that develop students' social, mental, and physical health
- Portfolio includes Bettermynd (mental health for higher-ed), Valera Health (personalized mental health services), and Learnfully (learning intervention for neurodiverse learners)
Healthcare (Core Pillar)
Focused on three healthcare sub-themes:
Inclusivity & Cultural Relevance
- Healthcare that is culturally relevant and financially inclusive for all demographics
- Portfolio includes Clever Care (holistic Medicare alternative for diverse communities) and Brellium (AI compliance platform)
Better Outcomes & Cost Reduction
- Healthcare that is straightforward, accessible, and reduces spending while improving treatment at scale
- Focus on operational efficiency and patient outcomes as co-equal drivers
Value-Based Care
- Funding products that tie compensation to patient results for more equitable provider models
- Alignment of financial incentives with health outcomes
Climate (Core Pillar)
Focused on two climate sub-themes:
Market Mechanisms & Financial Systems
- Financial and market systems that scale climate solutions (banking, insurance, measurement platforms)
- Portfolio includes Oka (carbon insurance solutions de-risking global carbon markets) and Clean Energy Credit Union (affordable clean energy financing)
- Emphasis on aligning economic incentives with environmental benefits
Agricultural Innovation
- Solutions that improve soil health, reduce agricultural emissions, and enhance farm productivity
- Sustainable inputs and practices that benefit both farmers and the environment
- Direct connection to Kaushik's CFI platform and venture history in agricultural economics
Stage Focus and Check Size
Figure Eight focuses exclusively on early-stage companies with a documented preference for Seed stage, with check sizes of $50K-$500K. They occasionally follow on Series A for exceptional portfolio companies and consider pre-seed for founders with exceptional track records. The documented check size range indicates a focused strategy on early-stage capital deployment, often serving as first institutional money for impact-oriented founders.
Geographic Focus
- Primary: US (with particular strength in education and healthcare given US market scale)
- Secondary: UK and Europe (Diana's teaching background, Kaushik's PUK Ventures experience)
- Emerging: Global for climate solutions (carbon markets are inherently global)
The firm has lived experience across UK, Switzerland, and Colorado, suggesting a multi-geography investment orientation. However, US-focused impact is the dominant geographic thesis.
Recent Activity and Fund Status
Figure Eight launched in 2017, now operating for ~8 years. Portfolio companies span the full lifecycle with multiple exits/acquisitions indicating successful outcomes. Currently actively deploying from existing fund capacity and continuing to add new portfolio companies across all three sectors. Recent expansion of operations (team relocation to Western NC) suggests ongoing growth.
Portfolio Overview
Figure Eight's visible portfolio spans 25+ companies across three core sectors:
Education Portfolio: Osmosis, Signal Vine, Pathful/Nepris, BitClass, Learnfully, Mursion, Sparkwise
Healthcare Portfolio: Clever Care, Brellium, Valera Health, Bettermynd, Mintago, Prosapient
Climate Portfolio: Clean Energy Credit Union, Oka, Walapay
Decision Process and Investment Approach
Figure Eight operates as a partnership model with two co-founders making investment decisions. They emphasize swift execution with minimal administrative overhead and maintain a deep, operational engagement model. Founders work directly with Diana and Kaushik (not filtered through junior staff). They leverage Diana's pedagogical expertise and Kaushik's operational/entrepreneurial background, with stated commitment to lasting relationships and support throughout company lifecycle. Warm introductions are the preferred entry mechanism.
Founder Preferences
Figure Eight explicitly targets impact-oriented founders who share values alignment, demonstrate operational capability, have founder-led product vision (particularly for education), understand system-level impact (not just revenue growth), and seek deep partnership rather than just capital.
Competitive Positioning
Figure Eight's competitive advantages include the unique founder pairing (educator + repeat entrepreneur), pedagogical rigor ensuring education companies are truly improving learning outcomes, operational expertise from Kaushik's multiple exits, long-term commitment through 10% profits-to-nonprofits model, access to expertise through Diana's global teaching experience and Kaushik's CFI platform, and sector specialization in education, healthcare, and climate.
Conclusion
Figure Eight Investments represents a rare institutional combination: serious capital deployment with genuine impact commitment, run by two founders who bring complementary expertise (pedagogy + entrepreneurship) and deep values alignment. The fund's coherent thesis around inclusive education, healthcare accessibility, and climate solutions creates natural syndication opportunities and deep competitive advantage in identifying exceptional impact founders. With $50K-$500K check sizes and a partnership-based decision model, Figure Eight positions itself as the ideal lead investor for early-stage impact companies seeking both capital and operational partnership.