Crosby & Prince

Ventures

Crosby & Prince is a private advisory and venture partner firm working with a select group of leaders at defining moments of growth, complexity, and reinvention.

Portrait of Ryan Trainor, Founder of Crosby & Prince Ventures

My work begins where strategy and the leader's mindset align. Having built and led global companies, I know both the privilege and the pressure of leadership.

My role is uncommon. I step in as an entrepreneur in residence for a company, supporting CEOs both strategically and tactically, while also serving as a trusted confidant.

Sometimes that means shaping strategy. Sometimes it means challenging assumptions. And often it means going deeper with a leader into mindset, energy, and personal health, so clarity and conviction return.

Scroll down to next section
Grow without alignment is speed without direction.
Growth with alignment endures.
Ryan Trainor, Entrepreneur in Residence
Scroll down to next section
Grow without alignment is speed without direction.
Growth with alignment endures.

How I Support

Entrepreneur-in-Residence
& Trusted Counsel

I provide counsel to founders and CEOs at the moments when clarity matters more than momentum. Having built and led companies through capital raises, market entries, cultural realignments, and reinvention, I understand the weight of these decisions.

My role is to create the space for perspective, to test assumptions with honesty, and to support leaders in moving forward with confidence. This is not only about strategy. It is also about alignment, ensuring the leader themselves have the clarity and energy to carry out the decisions that will shape the company and its culture.

How I Support

Venture Partnerships
& Investor support

I engage in venture partnerships only when strategic alignment is clear, and values are built to endure. Capital alone is never enough. Sustainable growth requires stewardship as much as investment.

My work in these partnerships often includes:

  • Investment assessment beyond financial models to evaluate market positioning, strategy, and growth potential.
  • Mentorship of CEOs and founders navigating the pressures of scale, reinvention, and investor expectations.
  • Discreet board representation offering counsel shaped by decades of experience.

I step in where conviction matters and stay engaged where my presence helps ventures grow with clarity, integrity, and long-term impact. When alignment is strong, I often co-invest alongside the investors.

How I Support

Global Expansion
& Capital Access

Cross-border growth requires more than introductions. It requires trust, translation, and execution. Through long-standing networks across the Gulf, India, North America, and Southeast Asia, I help leaders expand with confidence and cultural fluency.

These networks deliver insight and trusted partnerships, bridging differences between markets and mindsets to ensure expansion grounded in discipline and lasting impact.

Next Section Arrow

How I Work

I work with only a small number of leaders and organisations each year. This deliberate focus allows me to bring the depth, trust, and presence that meaningful impact requires. Each engagement is anchored in discretion, clarity, and long-term alignment, with significance always taking precedence over scale.

Start a Conversation

About Ryan

I have spent more than 30 years at the intersection of entrepreneurship and leadership. I have founded and exited global ventures across education, technology, health, media, and gaming, while also chairing boards and guiding companies into more than 40 countries.

Ryan Trainor - Entrepreneur and Advisor

I was recognised as a regional Ernst & Young Entrepreneur of the Year and later served as national Chair of Judges, reflecting my long-standing commitment to the entrepreneurial community.

My work today is shaped as much by inquiry as by experience. I am deeply focused on human potential, the systems that influence how we live and work, and the conviction that growth without alignment rarely sustains. For me, true progress does not come from speed or scale, but from conscious and courageous decisions anchored in clarity and values.

That belief defines how I now work. I partner discreetly with a small number of leaders and ventures each year as an entrepreneur-in-residence and trusted confidant.

Whether supporting founders and CEOs one-on-one, stewarding complex strategy, or guiding cross-market growth, I support leaders and ventures at the moments that matter most.

Connect with Ryan
Ryan Trainor, Founder of Crosby & Prince Ventures