May 2–5, 2027 | Kansas City, MO
May 2–5, 2027 | Kansas City, MO
Opening Keynote · Monday, May 3
Bert Jacobs is the co-founder and CEO of the $160 million lifestyle brand Life is Good. When he and his brother John started the company in 1994, they had $78 in their pockets, lived out of their van, and sold T-shirts on the streets of Boston. Was this their way of avoiding the “real world?” You bet. Did it turn into something much bigger? Absolutely.
Thirty years later, Bert and John still champion the same mission: to spread the power of optimism. They draw inspiration from a community of resilient optimists who embody three simple words: “Life is Good.”
The brothers also know life isn’t easy. The company donates 10% of its annual net profits to the Life is Good Playmaker Project, which helps over one million kids overcome poverty, violence, and illness annually. This for-profit/non-profit model puts the business to work for others.
Because of his unique perspective, which ties rational optimism to business, Bert has received honorary degrees from five universities and colleges. He has spoken at Inc. 5000, Morgan Stanley, SAP Sapphire, and Discover. He and John have been featured in Forbes, The New York Times, and The Wall Street Journal, and on NPR’s “How I Built This” and NBC’s “The Today Show.”
Tuesday Breakfast Keynote · Tuesday, May 4
Sarah Robb O’Hagan’s career is a story of bold risks, big wins, and resilience at the highest levels of business. Fired twice in her twenties, she became one of the youngest executives to lead a multibillion-dollar brand. By 38, she was Global President of Gatorade, driving its turnaround into a sports performance brand. That arc of falling, learning, and climbing higher shapes her view of leadership and peak performance.
In high-energy keynotes, Sarah gives audiences practical tools to unlock performance, individually and as a team. With candor and humor, she shares the behind-the-scenes grit of leading world-class teams. Audiences leave with strategies for finding their competitive edge, turning setbacks into comebacks, and building teams that collaborate with trust.
Sarah reimagined Virgin Atlantic’s brand partnerships, reinvented Gatorade, transitioned Equinox into a digital-first fitness powerhouse, and, as CEO of EXOS, pioneered a workplace culture model that increased productivity while reducing burnout. Fortune 100 companies have adopted her approach.
Forbes named her one of the “Most Powerful Women in Sports,” and Fast Company named her one of the “Most Creative People in Business.” She has served on the boards of Strava and JetBlue Airways and championed initiatives empowering women and girls through sports.
Wednesday Breakfast Keynote · Wednesday, May 5
Known as The Iron Cowboy for the hat he wears while racing so his five kids can spot him from afar, James Lawrence is an ultra-endurance athlete who has pushed past what many doctors believed was physiologically possible.
A former high school wrestler, James spent a decade in mortgage and finance before losing everything in the 2008 financial crisis. At rock bottom, he struggled to finish a four-mile fun run with his wife, Sunny, and learned a lesson that has guided him since.
“I learned quickly that everyone’s ‘hard’ is different. Back then, four miles was really difficult for me. I learned that one of the most important things in life is to just show up.” — James Lawrence
In 2012, James completed 30 Ironman triathlons (a 2.4-mile swim, 112-mile bike, and 26.2-mile run) in one year, earning a Guinness World Record. In 2015, he completed 50 in 50 consecutive days in 50 states while raising money to combat childhood obesity, the subject of the Amazon Prime documentary Iron Cowboy. In 2021, he completed 100 in 100 consecutive days, raising money to combat sex trafficking.
He has also summited Mount Kilimanjaro on a bicycle, completed the Race Across America, and run 235 miles across Greece.
A best-selling author, James has shared his story with audiences in 50 countries.
Titleholders Luncheon Keynote · Wednesday, May 5
The Best of Second City show brings world-class Second City performers delivering a mix of on-the-spot improvisational comedy inspired by suggestions from the audience, and pre-written sketches featuring some of their best work from over 50 years of performances!
Join us for an unforgettable keynote session of laughter and improvisation inspired by YOU!
