OpenAI and Anthropic are locked in a high stakes rivalry, and the fallout is hurting public trust in AI overall. In this episode, the "We Fixed It, You're Welcome" panel (Aaron Wolpoff, Melissa Eaton, and Chino) sits down with veteran tech PR strategist Perry Headrick to unpack whether the ChatGPT vs Claude rivalry is a branding win or a trust disaster. With over 20 years of experience representing brands like AOL, Bing, Yelp, and Logitech, Perry brings sharp, no nonsense insight into why both AI giants are missing the mark with everyday users, and what they need to do to fix it.

Guest Bio

Perry Headrick is the founder of Crackle PR, a B2B tech focused communications agency working with startups through publicly traded companies. He also co-hosts the Under Embargo podcast alongside Becca Chambers, CMO at Scale Ventures. Perry brings decades of experience in media strategy, reputation management, and crisis control.

Key Topics Discussed

• Why only 17% of Americans trust the people running major AI companies, and 40% consider them untrustworthy

• The origin of the OpenAI vs Anthropic rivalry, born from a philosophical split within OpenAI

• How the Super Bowl ad wars and competitive digs are backfiring on both brands

• The psychology of "AI dread" and why fear, not excitement, dominates public perception

• Why AI companies make themselves the star instead of the customer

• Perry's real world examples: turning heads at a local Chinese restaurant with an AI generated photo, and using AI to pick better golf clubs

• The case for radical transparency over "promiseware" and vague grandiosity

• Why sycophantic AI responses (agreeing with everything, false reassurances) erode user trust

• The Claude broken links example and why owning limitations matters more than smoothing them over

• Reddit and AMAs as an underused trust building tool

• Are OpenAI and Anthropic "too big to fail," or heading toward a Yahoo vs Google outcome

• Why competing companies dragging each other down risks making the entire AI category look unsafe

• DuckDuckGo's rise as a case study in giving users control (the option to turn AI off)

Connect with Perry Headrick

• LinkedIn: Perry Headrick

• Podcast: Under Embargo (co-hosted with Becca Chambers, CMO at Scale Ventures)

• Website: cracklepr.com

Connect With the Show

Subscribe for more deep dives where we fix big business problems with fresh perspectives.

• Website – www.wefixeditpod.com

• Follow us on:

Instagram – https://www.instagram.com/wefixeditpod

LinkedIn – https://www.linkedin.com/company/wefixeditpod

YouTube – https://www.youtube.com/@WeFixedItPod

If you liked this episode, don’t forget to subscribe, leave a review, and share it with your friends! Keep listening to find out how we fix companies and put them back better than we found them.

Disclaimer

A quick disclaimer. We are going into this somewhat cold and nothing we say should be construed as legal advice, financial advice or anything that would get us in trouble. These are our views and opinions. We’re here to ask the kinds of questions everyone’s thinking, have an engaging conversation and maybe come to some conclusions that we feel are worth exploring.

By the end, if we fixed it, you’re welcome. All trademarks, IP and brand elements discussed are property of their respective owners.

Learn more about your ad choices. Visit megaphone.fm/adchoices