Sports & Pop Culture Media Personality; Creator & Host of "Sundae Conversation"; Former Host at Barstool Sports

Live Event: $50,000 - $100,000 Virtual Event: Please Contact More Fee Info

Caleb Pressley Biography

Caleb Pressley is a media personality, content creator, and interviewer known for his work at the intersection of sports, comedy, and pop culture. Before entering the media industry, Pressley was a walk-on quarterback for the North Carolina Tar Heels football team, where he became known as the self-proclaimed Supervisor of Morale. After graduating from the University of North Carolina, he joined Barstool Sports, where he gained recognition through blogging, podcasting, and conducting viral celebrity interviews.

Pressley's podcasting work includes "Young & Happy" and "51 Strokes," a series chronicling his pursuit of a professional golf career. His short-form interview series, "Sundae Conversation," on YouTube, has established his reputation as an inventive interviewer in digital media. The show, co-hosted with Glen Medoro, features Pressley posing offbeat questions to celebrities while his co-host eats ice cream. The series has attracted guests such as Drake, Post Malone, Cardi B, Ed Sheeran, Josh Allen, Drew Barrymore, Theo Von, and Druski, and has accumulated hundreds of millions of views across YouTube and social media platforms.

Pressley's work extends beyond digital media. He has announced the new artist of the year at the CMA Awards and served as a host for Concert For Carolina in Charlotte, North Carolina, highlighting his experience as a live event emcee. He also hosted Season 2 of Druski's reality dating parody series "Coulda Been Love," expanding his presence in both scripted and unscripted entertainment.

Pressley later left Barstool Sports to launch his independent production company, Bill Joe Productions, through which he continues to produce and distribute "Sundae Conversation." This venture is supported by a partnership with Shadow Lion on sales, talent production, and collaborative projects. Pressley's personal brand and comedic, celebrity-driven content have garnered a substantial social media following and a diverse roster of high-profile guests, positioning him as a distinctive voice in modern media, sports entertainment, and digital content creation.

BOOK Caleb Pressley

Speaker profile last updated by AAE Talent Team on 10/05/2026.

Caleb Pressley Videos

DANNY MCBRIDE: Sundae Conversation with Caleb Pressley

DANNY MCBRIDE: Sundae Conversation with Caleb Pressley

Danny McBride and Caleb discuss what can be taught in schools.

  • How do I book Caleb Pressley to speak at my event?

    Our experienced booking agents have successfully helped clients around the world secure speakers like Caleb Pressley for speaking engagements, personal appearances, product endorsements, or corporate entertainment since 2002. Click the Check Availability button above and complete the form on this page to check availability for Caleb Pressley, or call our office at 1.800.698.2536 to discuss your upcoming event. One of our experienced agents will be happy to help you get speaking fee information and check availability for Caleb Pressley or any other speaker of your choice.
  • What are the speaker fees for Caleb Pressley

    Speaking fees for Caleb Pressley, or any other speakers and celebrities, are determined based on a number of factors and may change without notice. The estimated fees to book Caleb Pressley are $50,000 - $100,000 for live events and available upon request for virtual events. For the most current speaking fee to hire Caleb Pressley, click the Check Availability button above and complete the form on this page, or call our office at 1.800.698.2536 to speak directly with an experienced booking agent.
  • What topics does Caleb Pressley speak about?

    Caleb Pressley is a keynote speaker and industry expert whose speaking topics include Culture, Football, Host & Emcee, Marketing, Podcast Host, Social Media, Sports, Sports Journalism & Broadcasting, Television & Film
  • Where does Caleb Pressley travel from?

    Caleb Pressley generally travels from an undisclosed location, but can be booked for private corporate events, personal appearances, keynote speeches, or other performances. For more details, please contact an AAE Booking agent.
  • Who is Caleb Pressley’s agent?

    AAE Speakers Bureau has successfully booked keynote speakers like Caleb Pressley for clients worldwide since 2002. As a full-service speaker booking agency, we have access to virtually any speaker or celebrity in the world. Our agents are happy and able to submit an offer to the speaker or celebrity of your choice, letting you benefit from our reputation and long-standing relationships in the industry. Please click the Check Availability button above and complete the form on this page including the details of your event, or call our office at 1.800.698.2536, and one of our agents will assist you to book Caleb Pressley for your next private or corporate function.
  • What is a full-service speaker booking agency?

    AAE Speakers Bureau is a full-service speaker booking agency, meaning we can completely manage the speaker’s or celebrity’s engagement with your organization from the time of booking your speaker through the event’s completion. We provide all of the services you need to host Caleb Pressley or any other speaker of your choice, including offer negotiation, contractual assistance, accounting and billing, and event speaker travel and logistics services. When you book a speaker with us, we manage the process of hosting a speaker for you as an extension of your team. Our goal is to give our clients peace of mind and a best-in-class service experience when booking a speaker with us.
  • Why is AAE Speakers Bureau different from other booking agencies?

    If you’re looking for the best, unbiased speaker recommendations, paired with a top-notch customer service experience, you’re in the right place. At AAE Speakers Bureau, we exclusively represent the interests of our clients - professional organizations, companies, universities, and associations. We intentionally do not represent the speakers we feature or book. That is so we can present our clients with the broadest and best performing set of speaker options in the market today, and we can make these recommendations without any obligation to promote a specific speaker over another. This is why when our agents suggest a speaker for your event, you can be assured that they are of the highest quality with a history of proven success with our other clients.

Caleb Pressley is a keynote speaker and industry expert who speaks on a wide range of topics. The estimated speaking fee range to book Caleb Pressley for your event is $50,000 - $100,000. Caleb Pressley generally travels from and can be booked for (private) corporate events, personal appearances, keynote speeches, or other performances. Similar motivational celebrity speakers are Akbar Gbaja-Biamila, Madelyn Burke, Elisa Hernandez, Josina Anderson and Greg Wolf. Contact All American Speakers for ratings, reviews, videos and information on scheduling Caleb Pressley for an upcoming live or virtual event.

Tell us about your event!

During normal business hours, we respond to most inquiries within 4 hours.
Please Select Event Budget
Please enter your message
Please Enter Your Name
Please Enter Your Email
  • Customized Service

    Our agents find the right fit for your event

  • Unparalleled Database

    Full access to all speakers & celebrities

  • One Stop Shopping

    A reliable and unbiased point of contact

  • Logistics Management

    Your personal Logistics Manager who takes care of all event details

This website is a resource for event professionals and strives to provide the most comprehensive catalog of thought leaders and industry experts to consider for speaking engagements. A listing or profile on this website does not imply an agency affiliation or endorsement by the talent.

All American Entertainment (AAE) exclusively represents the interests of talent buyers, and does not claim to be the agency or management for any speaker or artist on this site. AAE is a talent booking agency for paid events only. We do not handle requests for donation of time or media requests for interviews, and cannot provide celebrity contact information.

If you are the talent and wish to request a profile update or removal from our online directory, please submit a profile request form.

TOP