Direct Investment Resources

A Trusted Advisor to Family Offices

Randy Castleman

Founder & Managing Partner

Senior Advisor, Forestay Capital (a unit of Waypoint Capital)

Senior Advisor, IP Group US

Senior Advisor, Signature Family Wealth Advisors

Co-Founder & Managing Partner, Court Square Ventures

EIR, Harvard's Wyss Institute for Biologically Inspired Engineering

BA, Princeton University

MBA, University of Virginia Darden School of Business

Experience with Emerging Technologies and Business Models Including

  • Artificial intelligence
  • Autonomous vehicles
  • Collaborative Robotics
  • Software 2.0
  • Industrial process optimization
  • DNA for data storage
  • Synthetic biology
  • Focused ultrasound therapeutics
  • Blockchain technologies
  • Software as a Service
  • Robotics as a Service
  • IOT and other edge comms

Family Office and Venture Investing Experience

Randy is an experienced venture investor and advisor to family offices multi-family offices, and outsourced CIOs on direct private investments, particularly in disruptive emerging technologies.

Single and Multifamily Office Experience

Randy currently works with single family offices on their direct investing. He recently advised a $5B multifamily office on the re-conception of its venture investing program via funds and direct investments, building a pipeline of high-quality venture managers in which the MFO could invest over the long term. This entailed developing a theoretical framework for the asset class (basic rationale, amount, strategies, timing, etc.) and practical implementation (sourcing and evaluating, due diligence, manager selection, and monitoring). Before his career in venture capital, he was president of a single family office, managing its direct investing, asset allocation, manager selection and monitoring.

Venture Capital Experience

Randy was a co-founder and partner of Court Square Ventures (Automated Insights, CSTV, Yandex), a venture capital firm investing in enabling technologies in communications, digital media, and information technology. There, he was involved in all aspects of the firm's operations, including fund conception and fundraising, staffing, deal sourcing and selection, portfolio management and company development, investment liquidity, and relationships with the firm’s top-tier institutional limited partners.

Emerging Technologies Experience

Randy has served as an entrepreneur in residence at Harvard's Wyss Institute for Biologically Inspired Engineering, where he advised top research scientists on commercial opportunities in robotics, artificial intelligence and DNA for data storage .

He was involved in the formation of synthetic biology startup Rheogene (acquired by Intrexon), was a senior advisor to a White House-convened CEO advisory council on intellectual property, privacy, and security, and headed technology strategy at ASCAP in NY. A career in media technology prior to business school included a founding role with Jodie Foster’s PolyGram-backed production company and roles with Interscope Communications in Los Angeles and Ogilvy & Mather in NY.

Randy has a BA from Princeton University and an MBA from the University of Virginia’s Darden School.

A Diverse Global Network

DIR's network is global and highly diverse, including industry decision-makers in communications, information technology, automation, robotics, and media. In finance, the DIR network includes venture capitalists, family offices and multifamiliy offices, OCIOs, endowments and pension funds as well as investment bankers and public fund managers. And in academia it includes some of the most prominent scientists and innovators in robotics, automation, materials science and synthetic biology. This network can be brought to bear on tough diligence questions, to de-risk investments and create business opportunities for portfolio companies.

DIR also has a network of trusted legal, tax and technical professionals around the world with which it works on all types of private investments.

Stewardship Alignment Returns