Outsiders Fund Research
Investment Thesis
Outsiders Fund is an early-stage venture capital firm that invests in founders bringing outside perspectives to overlook, antiquated, and long-standing industries. Led by Austin McChord (founder of Datto, which sold to Kaseya for $6.2 billion) and Theodore Seem (machine learning engineer from Bridgewater Associates and Resonance), the fund believes that technological innovation is unevenly distributed—the hottest sectors attract all the talent and capital, while massive value creation opportunities exist in unsexy, overlooked industries.
The fund's core thesis is that the most interesting investment opportunities often hide in spaces that have been overlooked by traditional venture investors. By identifying mismatches between sector-specific technological adoption and broader innovation, they discover opportunities to unlock significant value from legacy infrastructure. They specifically seek unique founders with unconventional backgrounds who bring fresh perspectives unburdened by "the way things have always been done."
Investment Focus and Sectors
Outsiders Fund deliberately targets traditionally overlooked markets across multiple sectors:
Industrial & Manufacturing:
- Cattle supply chain (Breedr)
- Industrial painting robotics (PaintJet)
- Heavy equipment servicing (Heave)
- Manufacturing and automation
Infrastructure & Hardware:
- Distributed GPU computing (Juice Labs)
- Electronic design automation (Flux.ai)
- Radiation hardening (Cosmic Shielding)
- Semiconductors and components (Mobius Materials)
- IoT and connected devices
Enterprise & Security:
- HVAC monitoring (Cognition Controls)
- Cybersecurity and cyber warranty (Cork)
- Enterprise software and diligence automation (DualEntry)
- Remote monitoring (Casana)
- Construction technology
Healthcare & Specialty:
- Women's health (Cercle)
- Clinical research (Dyania Health)
- Health monitoring (Lucea Health)
Aerospace & Transportation:
- Space bus manufacturing (Apex Space)
- Commercial aviation services (Kyte, Flight Science)
- Airport ground equipment (AeroVect)
Other Specialty Areas:
- Robotics and automation
- Enterprise tools and SaaS
- AgTech
- Telehealth
Stage and Check Size Focus
Outsiders Fund primarily invests at Seed and Series A stages, with occasional pre-seed investments. Their check size ranges from $500K to $8M, with the following pattern:
- Pre-Seed: $500K-$2M for early-stage concepts
- Seed: $1M-$4M for teams with initial traction
- Series A: $2M-$8M for growth-stage companies
The fund tends to be active in follow-on investments within their portfolio, indicating a "support and scale" approach to portfolio companies.
Geographic Focus
Primarily focused on the United States and Canada, with strong concentration in:
- Northeast (New York, Connecticut, Massachusetts)
- West Coast (California)
- Midwest (Texas, Wisconsin)
- Secondary Canadian investments (Montreal, Vancouver, British Columbia)
Recent Activity and Fund Status
Outsiders Fund appears to be actively deploying capital as of late 2025:
- December 2025: Investment in Mobius Materials (semiconductors)
- December 2024: Lead in Series A for DualEntry (enterprise diligence automation)
- June 2025: Participation in $25M Series A for Slide (MSP-focused cybersecurity, co-led by Base10 Partners)
- Portfolio Growth: 40+ investments made to date, with 4 new investments in the last 12 months as of December 2025
The fund operates with multiple funds (Fund II and Fund III referenced), suggesting sustained capital availability and continued operations.
Leadership and Team
Austin McChord, Co-Managing Partner: Founder and former CEO of Datto (acquired by Vista Equity Partners for $1.3B in 2017, later sold to Kaseya for $6.2B in 2022). McChord remained as a major shareholder and board member through the exit. Recipient of Forbes 30 Under 30 (2015) and EY Tech Entrepreneur of the Year (2016). RIT trustee and graduate. Known for bold investments in unsexy sectors (smart toilet seats portfolio company). Active founder and operator with deep technology and business-building expertise.
Theodore Seem, Co-Managing Partner: Machine learning and infrastructure expertise. Previously held roles as forward-deployed engineer at Bridgewater Associates and investment engineer on FX Research Team. Led machine learning initiatives at Resonance (neural network development). Harvard MBA from Harvard Business School. Amherst College graduate. Brings systematic, quantitative approach to investment decisions. Active in endurance sports and outdoor activities.
Supporting Team:
- Kira Vanderwert (Operating Partner)
- Michael Fass (Venture Partner) - Co-founder of Slide.tech with McChord
- Kevin King (Venture Partner)
- George Easley (Partner)
- Plus associates and operations staff
Decision Process and Involvement
The fund operates as a partnership model, with McChord and Seem as the primary decision-makers. The co-managing partner structure suggests collaborative decision-making rather than solo GP leadership. The operating partner role (Vanderwert) indicates hands-on support for portfolio companies beyond capital provision.
Portfolio Characteristics
Portfolio Size & Activity:
- 40+ portfolio companies
- Mix of seed, series A, and some series B/later stage follow-ons
- 1 successful exit: RootAI (acquired)
- 1 exit in portfolio: Zorus (acquired, cybersecurity/MSP)
Notable Portfolio Companies:
- Slide.tech - $25M Series A (cybersecurity for MSPs, McChord/Fass involvement)
- Flux.ai - Electronic design automation, Series A
- Breedr - Cattle supply chain, Series A
- Casana - Smart toilet seats for health monitoring, Series B
- Dyania Health - Clinical research platform, Series A
- Juice Labs - Distributed GPU computing, Pre-Seed
- Cork - Cyber warranty insurance, Series A
- Planned - Event planning SaaS, Series B
- Kyte - Commercial aviation API, Seed
- Saturday Robotics - Construction robotics, Series A
- PaintJet - Industrial painting automation, Series A
Portfolio Diversity: Wide range of stages (pre-seed through series B), geographies (US and Canada), and sectors. Strong emphasis on technically complex, infrastructure-heavy, or overlooked-market opportunities.
Warm Introductions
Based on the public website and portfolio, the fund appears to welcome inbound interest but likely values warm introductions for priority review. Contact: [email protected]
Investment Philosophy Summary
Outsiders Fund represents a contrarian approach to venture investing: finding massive markets that traditional VC ignores because they lack hype, celebrity, or consumer appeal. They back founders who have the grit and conviction to disrupt unglamorous but essential industries. The partnership structure, founder backgrounds (McChord as a successful operator, Seem as infrastructure engineer), and portfolio composition all reflect a "non-traditional" approach to venture—hence the fund's name.
Key differentiators:
- Market Selection: Overlooked, unglamorous industries with incumbent inefficiency
- Founder Profile: Unconventional backgrounds, technical depth, high conviction
- Support Model: Operating partner, co-founder involvement (McChord), hands-on support
- Stage Focus: Seed to Series A, with capacity for follow-ons
- Thesis Confidence: Clear, articulated investment perspective (not generalist)
Risk Considerations
- Limited Fund History: Founded in 2020 (5 years old), relatively young for VC
- Concentrated Leadership: Two co-managing partners means concentration of decision-making
- Sector Risk: Focus on overlooked sectors may contain higher execution risk
- Limited Public Information: Fund size/AUM not publicly disclosed, suggesting smaller fund or preference for privacy