Risk & Reward

Play. Decide. Learn.

Where games of chance meet the workplace.

What poker tables, casino floors, sportsbooks and office brackets teach about decisions, engagement and team culture, and how each generation approaches games of chance. Written for adults, with a leader's eye.

Sports Betting Apps and the Young Professional

Risk & Reward · October 3, 2026

Since Murphy v. NCAA, betting apps have moved into the same pocket as banking and food delivery. Here is what managers notice, and why bankroll basics belong among adult life skills.

What Poker Teaches the Next Generation of Leaders

Risk & Reward · September 4, 2026

Poker is the rare game where you can play perfectly and lose. That is exactly why it makes such a good classroom for young leaders learning to decide under uncertainty.

Office Pools, Brackets and Squares as Team Culture

Risk & Reward · August 10, 2026

Brackets, fantasy leagues and Super Bowl squares are among the few work rituals that truly cross generations. Here is how to run them so everyone feels invited to play.

A Las Vegas Conference Survival Guide for Speakers

Risk & Reward · July 12, 2026

Las Vegas hosts some of the biggest trade shows of the year. Our guide for speakers and attendees covers energy, schedules, resort networking and trying the tables the smart way.

What Casino Loyalty Programs Teach About Engagement

Risk & Reward · June 17, 2026

Casinos have spent decades learning how to make people feel valued enough to come back. Their loyalty programs hold real lessons for managers, and some clear limits.

Gamification at Work and the Slot Machine Problem

Risk & Reward · May 19, 2026

Points, badges and leaderboards borrow their power from the same psychology as slot machines. Here is how slots really work, and how to use game mechanics at work for meaning.

Risk Appetite Across Generations, From Bingo to Apps

Risk & Reward · April 24, 2026

Boomers met chance in the bingo hall, millennials at the online poker table, Gen Z on a betting app. Those first encounters say a lot about how each generation takes risks at work.

Articles and essays

More to read about managing and engaging every generation at work.

Four Reasons You Probably Need a Coach

Most of us rarely push ourselves outside our comfort zone. Here are four practical reasons a coach can help managers see their blind spots, follow through and lead better.

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Values, Skills and Passions: Find Where You Add the Most Value

Three overlapping circles, one sheet of paper and thirty minutes: a practical way to find the work where your values, skills and passions meet, and where you add the most value.

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How to Win the Millennial Race (and the Gen Z One)

A restored talk outline, updated for Gen Z: the trends that define younger generations, how to bridge youth and experience, and how to stay relevant as things keep changing.

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Header photo: Clément Bardot, CC BY-SA 3.0, via Wikimedia Commons.