Simplex Ventures

# Simplex Ventures: A Fintech-Focused Investment Arm Backed by Trading Expertise

High-Level Overview

Simplex Ventures operates as the venture capital arm of Simplex Trading, a technology-driven proprietary trading firm headquartered in Chicago.[1][2] The firm's mission centers on identifying and investing in early-stage companies that are reshaping the financial services landscape. Rather than pursuing a broad investment mandate, Simplex Ventures maintains a focused thesis: backing visionary founders building fintech solutions designed to disrupt and transform traditional finance.[2]

The investment philosophy reflects the parent company's DNA—a deep commitment to technology, data-driven decision-making, and operational excellence. Simplex Ventures positions itself as more than a capital provider; it functions as a strategic partner that leverages the trading firm's two decades of market expertise, proprietary technology infrastructure, and industry relationships to support portfolio companies.[1][2] This hybrid model—combining venture capital with the operational credibility of an active market participant—creates a distinctive value proposition in the fintech investment space.

Origin Story

Simplex Trading was founded in Chicago in 2004 as a proprietary trading firm, establishing itself as a technology-driven market maker focused on innovation and automation.[1][3] The parent company built its reputation by developing proprietary software and leveraging advanced data analysis to identify and capitalize on financial market opportunities. This foundation of technical excellence and market acumen became the bedrock upon which Simplex Ventures would later emerge.

Simplex Ventures itself represents an evolution of the parent firm's strategic thinking—a recognition that the future of finance would be shaped not just by trading firms, but by innovative startups disrupting traditional financial infrastructure. By launching its venture capital arm, Simplex Trading extended its influence beyond proprietary trading into the startup ecosystem, positioning itself as both a market participant and an investor in the companies reshaping that market. Leadership includes Erik Swanson as Chief Executive Officer and Kate Kitto as Head of Venture Capital, bringing both trading expertise and venture acumen to investment decisions.[1]

Core Differentiators

Operational Expertise from Active Trading

Unlike traditional venture firms that operate at arm's length from markets, Simplex Ventures benefits from the parent company's real-time market intelligence and proprietary technology infrastructure. This creates a unique advantage: portfolio companies gain access not just to capital, but to a partner that understands market microstructure, liquidity dynamics, and the technical challenges of building financial software at scale.

Strategic Investment Focus

Simplex Ventures concentrates on early-stage fintech companies, particularly those addressing market-making, trading infrastructure, and financial innovation.[4] This sector focus—rather than a spray-and-pray approach—allows the firm to develop deep domain expertise and create meaningful synergies between portfolio companies and the parent trading operation.

Collaborative Partnership Model

The firm explicitly emphasizes "truly collaborative partnerships" with founders, positioning itself as an entrepreneurial partner rather than a passive investor.[2] This approach suggests hands-on involvement in portfolio company strategy, potentially including technical guidance, market access, and operational support drawn from Simplex Trading's two decades of experience.

Track Record and Investment Activity

As of May 2025, Simplex Ventures has made nine disclosed investments, with recent activity spanning seed-stage and Series A rounds.[4][5] Notable investments include Sarna Finance ($2.5M seed in April 2023), Prevu ($6M Series A in December 2023), Cognito Health ($2M seed in March 2024), Fin—sustainable logistics ($7M seed in October 2024), and Pulse Charter Connect ($2M seed in May 2025).[4][5] The firm demonstrates willingness to co-invest with established venture players and specialized health-focused funds, suggesting a collaborative rather than territorial approach to deal-making.

Role in the Broader Tech Landscape

Simplex Ventures sits at an interesting intersection of traditional finance and fintech disruption. The firm represents a broader trend: established financial institutions and trading firms recognizing that innovation in their industry will increasingly come from outside their walls, prompting them to invest in and partner with startups rather than compete solely through internal R&D.

The timing is particularly relevant. As regulatory frameworks around financial technology mature, as institutional adoption of fintech infrastructure accelerates, and as the cost of building financial software decreases, early-stage companies can now tackle problems that previously required massive capital or regulatory moats. Simplex Ventures' positioning allows it to identify these opportunities while simultaneously providing portfolio companies with credibility and market access that would take years to build independently.

The firm also influences the broader ecosystem by demonstrating that venture capital in fintech need not be purely financial. By embedding venture investment within an active trading operation, Simplex Ventures creates a model where portfolio companies can access not just capital, but operational partnerships, technical infrastructure, and market intelligence—resources that traditional venture firms cannot easily replicate.

Quick Take & Future Outlook

Simplex Ventures represents a sophisticated evolution in how established financial firms engage with innovation. Rather than viewing startups as threats or distractions, the firm treats them as extensions of its own strategic vision—partners in reshaping financial markets.

Looking forward, several trends will likely shape Simplex Ventures' trajectory. First, regulatory clarity around fintech will accelerate institutional adoption of startup-built infrastructure, creating larger exit opportunities and justifying larger check sizes. Second, the consolidation of fintech infrastructure—where multiple point solutions merge into comprehensive platforms—will reward investors with deep market knowledge and operational relationships. Third, as artificial intelligence reshapes financial services, early-stage companies building AI-native trading and risk management tools will attract significant capital, and Simplex's technical credibility positions it well to evaluate these opportunities.

The firm's future influence will likely depend on its ability to generate strong returns while maintaining its collaborative ethos. If Simplex Ventures can demonstrate that its hybrid model—combining venture capital with operational partnership—produces superior outcomes for founders and investors alike, it may inspire other trading firms and financial institutions to adopt similar strategies. In doing so, it would reshape how capital flows into fintech innovation, moving away from purely financial transactions toward genuine strategic partnerships rooted in domain expertise.