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Fintech and Venture Capital Journey

Oct 3, 2025

Overview

This podcast episode features a discussion with Ian Sheridan, co-founder of Go Ventures and Vestigo Ventures, focusing on his journey in fintech, the evolution of financial technology and venture capital, and the importance of relationships, data, and teamwork in successful investing.

Ian Sheridan’s Early Career in Fintech

  • Ian began his career as a summer intern on the New York Stock Exchange, gaining hands-on experience on the trading floor.
  • Early exposure to both manual and emerging automated trading systems influenced his career direction.
  • Key mentors encouraged him to finish college, which later led to an opportunity with Goldman Sachs.
  • Noted the transformational impact of the transition from manual to computerized trading.

Evolution of Retirement and Asset Management

  • American workers transitioned from defined benefit pensions to 401(k)s and mutual funds during Ian’s early career.
  • The rapid growth in mutual funds and retirement plans led to significant changes in Wall Street technology and operations.
  • Data analytics and automation became increasingly vital in asset management.

Founding of Vestigo Ventures

  • Vestigo Ventures was founded by Ian Sheridan, Mark Cassidy, and Dave Blondon to invest in early-stage fintech and AI companies.
  • The founding vision emphasized supporting the Boston ecosystem and leveraging advances in data and predictive analytics.
  • Dave Blondon brought expertise in AI, launching multiple startups and building data-centric labs near MIT.
  • Vestigo’s funds have evolved to focus more heavily on AI and deep tech startups.

Approach to Venture Capital and Team Building

  • The team prioritized creating a multigenerational, diverse group reflecting the markets and founders they support.
  • Data and analytics have been central to investment decision-making, helping to identify promising startups.
  • Interns and younger team members brought fresh perspectives and helped identify potential biases in data interpretation.
  • Human connections at industry events and ecosystem involvement were critical for sourcing investment opportunities.

Use of Data and AI in VC Operations

  • Vestigo initially used in-house algorithms and manual scoring to assess potential investments.
  • As technology evolved, machine learning and large language models now automate much of the sourcing and filtering process.
  • Today, Ian leverages AI tools like ChatGPT and Claude for research and decision support.

Reflections on Impact and Collaboration

  • Relationships and simple acts of kindness were highlighted as instrumental in career growth and success.
  • Teamwork, collaboration, and a strong organizational culture are considered essential to sustained venture capital performance.

Questions / Follow-Ups

  • How does Go Ventures further differentiate itself from other VC firms in its daily operations?
  • What specific strategies are used to maintain and enhance team culture as the organization grows?
  • What trends are anticipated for the next phase of AI and fintech investing?