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How to Activate AI-Assisted Writing with Robert Riggs [MAICON 2025 Speaker Series]

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MAICON brings together top visionaries and experts in the field of AI during a three-day conference packed with actionable sessions and networking events—all to position you as the change agent your organization (and career) needs. In this ongoing speaker series, we’re featuring these extraordinary leaders, with forward-looking predictions, actionable tips you can use today, and a preview of their MAICON 2025 sessions.

Robert Riggs is the host and creator of the Webby Award-winning True Crime Reporter® podcast. Shortly after its debut, he transformed the podcast’s first season—centered on a notorious serial killer—into a five-part streaming docuseries, Freed To Kill, which premiered on Fox Nation in March 2022.

Before his success as a podcaster and author, Riggs spent over 30 years as a broadcast journalist, reporting from The White House, Congress, the Pentagon, and various federal agencies during the Reagan and George H. W. Bush administrations. He was also embedded with the U.S. Army during the 2003 invasion of Iraq as a CBS reporter and later uncovered domestic links to terrorist networks.

Throughout his journalism career, Riggs earned prestigious recognition, including a Peabody Award and three Alfred I. duPont–Columbia University Awards for Investigative Reporting.

Robert became interested in AI when ChatGPT was originally released in 2022. He started listening to The Artificial Intelligence Show on a regular basis and devoted at least two hours daily to experimenting with AI as a writing and research assistant. 

Today, Robert expertly uses AI as an editorial assistant, research assistant, production assistant, and so much more. 

Session Preview: Elevate Your Content Creation Productivity 

In this MAICON session, Robert will demonstrate how to harness AI tools to supercharge your writing workflow and boost productivity—all while staying grounded in the principle that AI should enhance, not replace, compelling storytelling.

Teaching from experience, Robert taught his AI assistant to write in his personal style—submitting a hybrid of articles from the New York Times, Washington Post, and "New Journalism" created by the late Tom Wolfe.

Today, he leverages advanced chatbots across nearly every stage of the content creation process, including:

  • Using podcast transcripts to generate titles, introductions, Sora podcast art, and social media content
  • Extracting text from JPG images or PDFs of historical documents, such as old newspapers, for research
  • Summarizing PDFs of books authored by true crime writers featured on his podcast
  • Summarizing court documents and trial transcripts
  • Generating similes, metaphors, analogies, and foreshadowing elements
  • Writing closing statements or episode summaries
  • Creating YouTube content elements, including titles, thumbnail text, hashtags, and video descriptions
  • Summarizing analytical reports and offering audience engagement strategies
  • Conducting advanced research using Gemini Deep Research

Through real-world examples and hands-on insight, Robert proves that the potential to extend the reach and purpose of your content is limitless when you integrate AI with intention. Discover how you can unlock new levels of efficiency and creativity in your own storytelling.

Lesson Learned: Always Go Deeper 

As the saying goes, there’s more than meets the eye. Even if you ask your AI tools open-ended questions, always follow up. 

Robert puts it simply, “Don’t accept the first answer to your prompt.” 

Instead, take it a step further. Always go deeper. Ask “why,” “what else,” or “what’s missing?” 

The best insights often come a few questions later. Staying curious, and staying current, is key in a fast-moving AI landscape.

Looking Ahead: The Future Is Independent 

AI is causing a massive shift in media production. Thanks to AI tools for scriptwriting, voiceover, video editing, and more, creators can now produce high-quality content at a fraction of the cost of traditional methods.

Robert says, “Artificial intelligence will enable small independent TV producers and content creators to cost-effectively produce shows, which will permit them to retain ownership rights.”

Independent creators have more power than ever to create professional content without the help of big production houses. 

Links We Like 

In all the following pieces, Robert leverages ChatGPT and Sora to write, create titles, produce social media posts, and create videos and/or images. 

Will You Break The Silence for $1 Million? - Cold Case Murder Mystery Award

Skip to these timestamps to see exactly where Robert used Sora:

  • Crime scene reenactment: :35 - :39
  • Cell phone tower: 13:02 - 13:24 
  • Animation: 15:17 - 15:44 
  • Recreation detective: 15:45

Why Do Women Love True Crime?

Robert noted that this piece is a prime example of using Sora to create podcast art. 

The James Bondesque Mafia Spies Plot To Kill Castro With A Poison Cigar

In this example, see how Robert used ChatGPT to convert the podcast script into a print story for newspapers and my website.

CIA Mafia Plot To Kill Castro Hidden From JFK Assassination Probe

Discover how Robert leveraged Sora to create Photoshop-style graphic images of the mobsters Johnny Roselli and Sam Giancana. In order to create these, he uploaded photographs of both men and prompted Sora to respectively place them in a late 1950s scene on Sunset Blvd. and at a Casino in Havana.

Robert’s Session at MAICON

AI-Assisted Writing for Storytellers 

Robert previously collaborated with a team of producers and researchers to craft his television stories. Today, Open AI’s ChatGPT and Anthropic’s Claude serve as his virtual collaborators in the storytelling process for his Webby Award-winning True Crime Reporter® Podcast.

In his presentation, Riggs will guide creators through how he harnesses AI to streamline the production process, using it to assist with research, generate titles, create thumbnails, and craft engaging introductions for each episode. He will also showcase how he has trained AI to write in his signature New York Times style, seamlessly converting episode transcripts into 1,000-word print articles for both his podcast and newspapers.

Additionally, Riggs will share his method for transforming podcast episodes into a cohesive audiobook series and a digital book for Kindle, using AI to expand his content across multiple platforms.

He emphasizes that AI is not a replacement for creativity. Instead, it is a powerful tool that, when used correctly, serves as an efficient assistant and significantly boosts productivity.

Keep Up with Robert (and AI) 

For more Robert Riggs, follow his storytelling journey through the True Crime Reporter podcast and on social media:

Plus, you can purchase his new book, Texas Crime Stories: Vol 1 Riding Herd On The Lawless, now on Amazon

Join Us at MAICON 2025 

Marketing Artificial Intelligence Conference (MAICON) was created for marketing leaders and practitioners seeking to drive the next frontier of digital marketing transformation within their organizations.

We’re excited to host our 5th annual MAICON—Marketing AI Conference—at this pivotal point for our industry.  Join us from October 14 to 16, 2025, in Cleveland, Ohio, and use the special code SPEAKERSERIES100 at checkout to receive $100 off your registration!

Learn More About MAICON

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