This conversation brings together Eimear McCrann, Director EY Entrepreneur Of The Year and Anne Heraty, EOY Judge and Founder CPL Resourced, to unpack the realities of entrepreneurship from two deeply experienced perspectives β one from building and leading a business over decades, and the other from supporting hundreds of founders through every stage of growth.
Anne reflects on the long arc of her entrepreneurial journey, from early beginnings to international expansion, public markets, and ultimately stepping back from the business she built. She shares honest insights into resilience, leadership under scrutiny, and the personal trade-offs that come with responsibility.
Eimear shares what she has learned from working at the heart of the Entrepreneur of the Year programme, including why women often hesitate to put themselves forward despite strong businesses. Together, they explore how community, shared learning, and trusted relationships can make entrepreneurship more sustainable β especially during periods of uncertainty and change.
Leadership Requires Comfort With Uncertainty
Entrepreneurs must make decisions without full information, learning to respond rather than react when things change.
Building Through Cycles of Change
Businesses move through booms, crashes, and reinvention, requiring resilience and adaptability at every stage.
Confidence Gaps Still Affect Female Founders
Women tend to underestimate their readiness, particularly when recognition or visibility is involved.
Peer Networks Accelerate Better Decisions
Access to founders with lived experience helps entrepreneurs navigate challenges more effectively.
Letting Go Is a Leadership Skill
Stepping back from a business requires trust, planning, and an identity shift, not just financial readiness.
Entrepreneurship Is Ultimately About People
Teams, trust, and shared values shape sustainable businesses.
CPL
Founded by Anne Heraty in 1990, CPL grew from a small recruitment firm into a large international recruitment and outsourcing group employing thousands of people across multiple countries.
Irelandβs flagship entrepreneurship programme supporting founders through a year-long process focused on community, learning, and long-term impact.
00:00 β Introduction and Focus on Female Entrepreneurship
03:10 β What the EY Entrepreneur of the Year Programme Really Is
06:20 β Anne Heratyβs Early Business Beginnings
10:15 β Scaling, Market Crashes, and Reinvention
15:30 β Confidence, Timing, and Women Putting Themselves Forward
20:10 β The Value of Entrepreneurial Community
24:40 β Expanding Into New Markets and Cultural Differences
29:30 β Leadership, Uncertainty, and Decision-Making
33:45 β Letting Go of a Business and Life After Exit
38:10 β Advice for Young People and Building Relationships
42:30 β Reflections on Meaning, Legacy, and Impact
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