Big Bets & Bracket Busters
Get ready to dive into epic wagers and wild bracket surprises—all in one awesome live event!
Big Bets & Bracket Busters
Every March, we’re reminded how quickly certainty disappears. Brackets bust. Favorites fall. Outcomes rarely follow the script.
CEOs live in that same reality every day.
This CEO Leadership Forums session explores a core leadership truth: great leaders and investors are not defined by perfect outcomes, but by the soundness of their decisions.
In private investing, no one expects every bet to win. What separates successful investors over time is not prediction, but disciplined decision-making, clarity of process, and the courage to act without perfect information. The same is true for CEOs.
This session is designed for leaders navigating growth, uncertainty, and high-stakes decisions who want to sharpen judgment, move with conviction, and avoid waiting for certainty that never comes.
Get ready to dive into epic wagers and wild bracket surprises—all in one awesome live event!
Big Bets & Bracket Busters
Every March, we’re reminded how quickly certainty disappears. Brackets bust. Favorites fall. Outcomes rarely follow the script.
CEOs live in that same reality every day.
This CEO Leadership Forums session explores a core leadership truth: great leaders and investors are not defined by perfect outcomes, but by the soundness of their decisions.
In private investing, no one expects every bet to win. What separates successful investors over time is not prediction, but disciplined decision-making, clarity of process, and the courage to act without perfect information. The same is true for CEOs.
This session is designed for leaders navigating growth, uncertainty, and high-stakes decisions who want to sharpen judgment, move with conviction, and avoid waiting for certainty that never comes.
What We’ll Explore
● Why waiting for perfect information often costs opportunity
● Decision quality vs. outcomes and why leaders confuse the two
● How investors evaluate risk without knowing the result
● When staying the course is the right call and when exiting is leadership
● How disciplined decision-making compounds over time
Lineup
John Crossman - President
Good to know
Highlights
- 2 hours
- In person
Refund Policy
Location
Legion Place
Legion Place
Orlando, FL 32801
How do you want to get there?

Agenda
-
Registration and Networking
Connect with fellow CEOs and business leaders before the session begins.
-
Keynote and Investor Perspective
A candid look at decision-making through the investor lens.
-
Facilitated Group Discussion
A peer-driven conversation on how CEOs are making and evaluating big decisions today.