World Series Champion helping leaders and teams build belief, ownership, and a winning culture.
Keynote speaker, workshop leader, and coach · Author of The Why Not Journal
Leadership and CultureResilience and Mental WellbeingPeak Performance and Mindset+2 moreForum Skills and DevelopmentTransitions and Difficult Conversations
The Why Not Mindset: Build Belief, Take Ownership, Create Momentum
$15,000
Keynote·Under 1 hour·In person or virtual
For entrepreneurs and business owners, CEOs and senior executives, executive peer groups, next-generation leaders, general corporate audiences, and boards and nonprofit leaders.
Drawing on a 10-year Major League Baseball career that included a World Series championship and being sent down, traded, or released 26 times, Ryan connects candid stories and humor with practical tools for leading through uncertainty. Through guided reflection and an audience action exercise, participants explore four questions: 'Why Not You, More, Us, and Now?' and leave with a specific commitment to strengthen their own performance and their team's.
A reframing tool to challenge limiting beliefs and act before confidence feels complete.
A practical approach to create and sustain momentum through setbacks, uncertainty, and change.
A “Why Not Now?” action plan connecting personal ownership to stronger team performance.
I'm a World Series Champion, Olympian, and former Major League Baseball catcher. But the most useful lessons I share come from being sent down, traded, or released 26 times. And learning how to keep believing, adapting, and contributing.
Today, I help leaders and teams apply The Why Not Mindset to their own challenges: building belief, taking ownership, strengthening trust, and turning intention into action. My work includes keynotes for organizations such as Pizza Hut, Hubbell, and Empower, executive coaching, and leadership development with the Chicago Cubs.
I bring candid stories, humor, and practical exercises that help people connect what happens on a baseball field to what happens in their workplace. At home in Denver, I'm a husband, a girl dad, and an Ironman finisher who keeps asking, “Why not more?”
The Why Not Journal helps readers turn reflection into action.
Executive coaching: Individual coaching helps leaders build confidence, take ownership, and navigate difficult decisions.
Leadership training: Customized workshops help teams strengthen trust, communication, accountability, and performance.
Organizer feedback
5.08 organizer reviews
Collected by Short List Speakers from organizers who booked Ryan and published regardless of sentiment. How we collect feedback
What organizers mention most: Engaging, Prepared, and Stayed on topic.
Every year, we conduct a survey, following our annual conference at the Colorado staffing association, and it was evident that Ryan’s presentation unanimously was viewed as one of the best key notes we have ever had! I would highly recommend him
Before the eventRyan was very communicative, and he was very accommodating to ensure that he met with the board of our association, a number of times leading up to our conference
During the sessionEveryone was locked in… Now only was he entertaining and energetic, but his content was tangible, and it truly teed up kicking off our annual conference with the right passion and energy, and mindset to be able to glean everything we could from the rest of the conference
After the eventRyan did a phenomenal job following up after the conference to ensure that his content and contact information was available to our organization. He has even done a wonderful job of going above and beyond in staying in contact with us just from a human standpoint.
Adrian · Colorado Staffing AssociationThe Why Not Mindset
Leadership is a complex and often discussed topic, and can easily be perceived as a "not this again" topic . Don't let that stereotype make you bypass an opportunity to work with Ryan. Ryan exemplifies leadership. His personal story showcases triumph over adversity. He engages the audience, tells funny and compelling stories to illustrate his points, dances, and makes fun of himself in the process of demonstrating what extraordinary leadership looks like. The three hours he spoke to my team felt like 30 minutes. People were fully engaged, and still refer to him almost a year later.
Before the eventBooking Ryan was easy - he was available for the date I wanted, he was easy to schedule time with for the planning session, and he touched base the week of the event to finalize everything as well.
During the sessionPeople relate to Ryan - he is the guy that everyone likes, and he knows his stuff. His real life stories bring his concepts to life. He is funny and engaging and his content is immediately applicable.
After the eventHe was open to feedback (all positive) and several of the people in the audience were able to connect with him post speaking session. His authenticity makes him approachable.
Tanya · Above The Tree Line Consulting GroupWhy Not Leadership
The preparation was done via email and text. I have known Ryan for a few years and there was comfort in that approach. He has a great story and he positioned it well. 12 year career in the major leagues and was sent down or downright released 26 times. A great story on resilience and dedication. His other key takeaway was "why not me?". He spiced in the right amount of humor and connected with the great and with individuals in the group. I have referred Ryan to several business colleagues and know he is engaged with a few of them.
Brian · CRC BenefitsUnleashing Potential
The first time I brought Ryan in I thought I was doing him a favor. But the team was blown away, I was blown away by what he brought to the table. I brought him in again to speak to our executive leadership team and the whole team was pumped for our special guest!
Before the eventRyan is a total pro. Clear communication and delivered exactly what was expected.
During the sessionRyan connects with his audience incredibly well. The newer members of the team loved him as much as the senior members. Great delivery!
After the eventSmooth and well executed!
Dan · Spear PTThe Why Not Mindset
I am just in awe of you as a human being, and then you are such a dynamic speaker on top of that. I truly cannot sing your praises enough. If I come across opportunities where I can share your name or what you're doing, I absolutely will. I know you don't need me to do that, but I would be honored to. You bring such an incredible energy into a room. The way you engage an audience is unlike anything I've seen recently. There is something really special about the way you bring people into your journey and your story while also using humor to make those moments connect. I'm not kidding when I say my jaws literally hurt by the end of your talk from laughing so much. You were exactly what we needed to close the day. After everything that had been shared and experienced in that room, you brought this incredible energy that allowed us to end on such a high. I also feel incredibly honored that you put together something new at the end of your talk specifically for this event.
Before the eventRyan was professional from our very first conversation. Booking him, coordinating his involvement, and arranging payment were easy and efficient.
During the sessionRyan’s session was one of the most engaging and hilarious sessions of the day while remaining professional throughout.
After the eventRyan followed up to ensure we had any materials we wanted to share with the audience.
Candice · Warrior DefinedThe Why Not Mindset
It was such a privilege, and a real highlight of my journey, to share the stage with you over the past two days. You have a natural ability to connect with leaders of all ages. Your energy and animated style invited everyone to take part in your keynote, creating an experience where attendees could engage with your ideas rather than simply sit and listen. I also appreciated the time you took to learn about our event before you arrived. Your preparation helped create seamless connections between your message and our other presenters' work. We heard wonderful feedback today, especially about how your message complemented Erin and Katie’s work. That combination could be powerful for audiences here in Connecticut and across the country, and I’d love to explore how we can continue working together.
Before the eventRyan was responsive, personable, and thoughtful from the start. He took time to understand our event, audience, mission, and values, tailoring his message to support our work beyond the presentation.
During the sessionDuring the session, Ryan proved a master storyteller, engaging participants through thoughtful insights, laughter, and emotion. He naturally connected, engaged, and inspired leaders across generations
After the eventRyan stayed through the event's conclusion, making time to connect personally with attendees. He also followed up with our organizers for feedback, and we're already planning his next appearance.
Mindset of a Champion
Ryan is a pro, has a solid message and would inspire any audience to reflect on their own performance, owning their results and building resilience.
Before the eventEasy to coordinate and communicate with - prepared and clear on our mutual objectives
During the sessionProfessional, at ease with the attendees - connected quickly drawing them into his content. Great storyteller.
After the eventGreat communication - generous offerings for further support.
Nancy · Vistage WorldwideRedefining Resilience
Thank you so much for your fantastic presentation at the TACUA event! We received so much positive feedback about your session, it was the perfect way to kick off the conference. Your ability to connect your message so effectively and resonate with Internal Audit made a strong impression and really set the tone for the rest of the week. We truly appreciate how engaging and insightful your session was, and it was a pleasure working with you throughout the process. Thank you again for helping make the event such a success!
Before the eventBooking, preparation and communication was a breeze. Ryan was very engaging and he wanted to learn all the details of the audience he would be presenting to.
During the sessionThe feedback from the audience was very positive, Ryan's presentation stood out because he had completed the research on what internal auditors do and the language that we speak.
After the eventNo specific follow up was completed other than to thank him for the great presentation and let him know that it was very well received and appreciated.
