Caspar Berry
Most organisations say they want to take more risks. Their leaders then make decisions that feel safe but are, mathematically, far more expensive than the risks they refused. Risk aversion trained into individuals through culture and incentive structures consistently destroys long-term value; not through recklessness, but through chronic underperformance disguised as caution. The organisations that consistently outcompete are not luckier; they understand uncertainty better.
Caspar Berry, a Cambridge-educated former professional poker player and Fellow of the RSA, helps organisations close the gap between their stated appetite for risk and the risk-averse decisions their leaders actually make.
Full Profile
Why organisations work with Caspar Berry
- Berry’s argument has a mathematical foundation, not just a motivational one: every decision is an allocation of scarce resources under uncertainty, and the mathematics of that process produce outcomes that are counterintuitive and consistently misread by leaders operating on instinct and habit.
- He makes the case, grounded in decision-making science, not poker storytelling, that risk aversion is not conservatism but a measurable source of underperformance; organisations leave value on the table not by taking too many risks but by taking the wrong ones for the wrong reasons.
- The poker metaphor functions as a precision instrument: it makes uncertainty undeniable in a way that corporate language typically suppresses, which creates genuine permission for leaders to reexamine how they decide rather than simply defending what they have always done.
- Berry has taken this framework to audiences at RiskMinds International (the senior financial risk conference) and to the UK Home Office leadership, demonstrating that the argument holds at both the technically demanding and the culturally complex ends of the risk conversation.
- Over 400 Mind Gym training sessions and more than 2,500 keynotes across 30 countries have stress-tested and refined the material against organisations from Google and KPMG to Morgan Stanley and Barclays, audiences where the argument must be robust, not just engaging.
Biography highlights
- MA in Economics and Anthropology, Cambridge University
- Professional poker player, Las Vegas: three years competing against leading professionals on the circuit
- Co-founded Twenty First Century Media; built to 40 people; sold to Bob Geldof’s Ten Alps Plc in 2008
- Poker adviser on the 2006 James Bond film Casino Royale; co-presenter of Sky Poker and host of Poker Night Live
- Trainer, The Mind Gym: over 400 sessions delivered to 100+ companies
- Contributor, Financial Risks Today, on behavioural risk and decision-making, for financial risk professionals
- TEDxAcademy: “Dealing with Uncertainty”; featured speaker, RiskMinds International
- ‘Best New Speaker’, Academy of Chief Executives, 2008; Fellow of the RSA
- Over 2,500 speeches and workshops in 30+ countries; clients include Google, IBM, KPMG, Morgan Stanley, Barclays, PayPal, Shell and the UK Home Office
Biography
Caspar Berry studied economics at Cambridge, spent three years as a professional poker player in Las Vegas, built and sold a media company, and then built one of the more rigorous arguments in the speaking world for why most organisations are making worse decisions than they think. The career arc is unusual. The intellectual case it produces is the point.
The core argument is mathematical before it is motivational. Berry treats every decision as an investment; an allocation of scarce resources under conditions of uncertainty. Decision-making science, he argues, reveals a set of counterintuitive implications that consistently lead intelligent leaders astray: some decisions that feel prudent are quantifiably expensive; some that feel reckless are simply the rational choice. Poker, where uncertainty is undeniable and unambiguous, is the vehicle through which those implications become accessible.
After Las Vegas, Berry co-founded Twenty First Century Media, built it to 40 staff and sold it to Ten Alps Plc. He spent several years as a trainer at The Mind Gym (over 400 sessions across more than 100 companies) before establishing his own practice. He has since delivered over 2,500 keynotes and workshops in more than 30 countries, for clients ranging from Google, IBM and PayPal to Morgan Stanley, Barclays and the UK Home Office. He has spoken at RiskMinds International alongside senior financial risk professionals and contributes to Financial Risks Today on behavioural risk and decision-making.
Berry holds a Fellowship of the RSA and was named Best New Speaker by the Academy of Chief Executives in 2008. His TEDxAcademy talk on uncertainty has been cited by investment firms as a reference point for decision-making under ambiguity. The argument is neither a poker book nor a leadership manifesto. It is a framework for thinking about risk – and it is specific enough to be genuinely useful.
Key speaking topics
- Risk-taking and decision-making under uncertainty
- The mathematics and psychology of risk
- Organisational risk culture and innovation
- Intuition, judgement and cognitive bias in high-stakes decisions
- Calculated risk as competitive strategy
- Fear of failure and long-term performance
Ideal for
- Senior leadership teams and executive boards examining risk appetite, innovation culture, or strategic decision-making
- Strategy and transformation leads responsible for shifting how their organisations act under uncertainty
- Financial services, professional services, and consulting firms where risk literacy is commercially material
- Conference programmers building around leadership, performance, or organisational resilience
Audience outcomes
- A reframing of risk: from a hazard to be minimised to a resource to be understood and allocated deliberately
- Working understanding of how decision-making science applies to everyday business choices; including the counterintuitive implications most leaders have never been taught
- Greater awareness of how intuition and cognitive bias distort risk assessment, and practical means of compensating
- Organisational language and permission to discuss risk appetite at leadership level with precision rather than generality
- A renewed confidence to act under uncertainty rather than waiting for a certainty that will not arrive
Talks
Uses poker as a precision metaphor for decision-making science, building the case that all decisions are investment decisions and that organisational risk-aversion is as mathematically costly as it is culturally entrenched.
Key takeaways:
- Every decision is a resource allocation under uncertainty; that reframe changes how decisions get made
- Some risk-averse instincts are not prudent but quantifiably expensive, and the mathematics show it
- The fear of failure, properly understood, can be converted from a brake into a competitive asset