What happens when a generation grows up with AI as a daily companion—and the rest of us are still catching up? In this episode, we sit down with New York Times journalist and podcaster Kevin Roose to unpack how artificial intelligence is already transforming the way we work, learn, and connect. From teens using AI to write essays or talk through their emotions, to companies quietly integrating it into operations while navigating public backlash, the changes are happening fast—and not always out in the open.

We explore with Kevin why media outlets remain skeptical, shaped by years of tech industry overpromises, and how employers are weighing the reputational risks of automation against its undeniable advantages. Kevin calls for more honest, transparent leadership as AI reshapes the economy and society in real time.

As we dig into these tensions, we also talk about Kevin’s long-standing fascination with belief systems—whether rooted in religion, finance, or tech—and how journalism helps him trace the deeper human motivations behind them. This is more than a conversation about where AI is going—it’s about who we are becoming as it gets there.

About Kevin Roose

Kevin Roose is an American author and award-winning technology columnist for The New York Times. He is the author of three books, the co-host of the “Hard Fork” podcast, and was included on the 2015 Forbes 30 Under 30 list.

Sponsored by:
Delve.

It ingests every public mention across your online universe, then decodes and pushes it past the top-level insights to create real, usable intelligence. Top global companies and agencies already use Delve to stay ahead.
Learn more at delve.news/shift

Resources discussed in this episode:

• Anthropic
• Chat GPT
• Futureproof: 9 Rules for Humans in the Age of Automation
• Vinod Khosla
• DALL-E
• Midjourney
• Cursor
• Replit AI
• Bolt
• Claude
• Hard Fork Podcast
• Character AI
• Replika

Contact Allison Braley and Sean Garrett:

• MixingBoard.co
• LinkedIn: Allison Braley
• LinkedIn: Sean Garrett
• Linkedin: Mixing Board
  
  

Contact Kevin Roose:

• Website: kevinroose.com
• Instagram: Kevin Roose
• Facebook: Kevin Roose
• X: Kevin Roose
• Linkedin: Kevin Roose
  
  

What does it take to make the bold switch from a successful career in comms to venture investing? We sit down with Ashley Mayer to find out why and how she made her career transition. We talk about those early Twitter days—when social media was still uncharted territory—and how Ashley helped her then-CEO build a voice online while simultaneously growing her own presence. She even revisits that unforgettable “AirPod subway rescue” moment, a reminder of how randomness and relatability can shape what resonates online.

We dig into the art of storytelling in both media and business. Ashley makes a compelling case for why founders should prioritize narrative clarity and strategic intent over the allure of personal branding or chasing viral fame. It's about substance, not just splash. Ashley also opens up about the challenges of early-stage investing—from evaluating founders’ visions to navigating uncertainty—and shares how she made the leap from communications to venture capital. Her reflections on timing, serendipity, and career evolution are refreshingly candid.

And of course, we get into her latest venture: the podcast Great Chat. Ashley gives us a behind-the-scenes look at what it takes to build something authentic from the ground up—why experimentation matters, how to stay patient, and what it really means to engage with an audience. Join us for a thoughtful and inspiring conversation about tech, media, and building with intention.

About Ashley Mayer

Ashley Mayer is the cofounder and GP of Coalition Operators, where she and her partners back early-stage founders. She began her career at enterprise software company Box, where she led global communications from a 50-person startup through IPO. She then moved to Social Capital, where she led all things marketing and communications for three years, helping to launch new capital products and working with founders spanning healthcare, aerospace, climate, fintech, enterprise and education. Most recently, she led communications at a New York-based beauty company, Glossier.

Ashley has also been a key advisor to Mixing Board since before its official inception and serves on the organization’s operating council.

Sponsored by:
Delve.

It ingests every public mention across your online universe, then decodes and pushes it past the top-level insights to create real, usable intelligence. Top global companies and agencies already use Delve to stay ahead.
Learn more at delve.news/shift

Resources discussed in this episode:

• Box
• Glossier
• Great Chat podcast
• Chat GPT - Open AI
• Brian Johnson - New York Times article
• Magentic
• Platformer
• Hard Fork podcast
• Lingo
• Aura

Contact Allison Braley and Sean Garrett:

• MixingBoard.co
• LinkedIn: Allison Braley
• LinkedIn: Sean Garrett
• LinkedIn: Mixing Board
  
  

Contact Ashley Mayer:

• Website: coalitionoperators.com
• X: @ashleymayer
• LinkedIn: Ashley Mayer
  
  

What does it take to write words that move a nation—and still feel deeply personal? We sit down with Cody Keenan, former chief speechwriter for President Barack Obama, to pull back the curtain on the craft of writing speeches that don’t just inform, but inspire. From Obama’s electrifying 2004 DNC address to poignant eulogies and everyday policy remarks, we explore how structure, storytelling, and emotional clarity come together to leave a lasting mark.

Cody walks us through his process, emphasizing why every great speech needs a clear beginning, middle, and end—and how tapping into values and real human experiences makes a message resonate long after the applause fades. We talk about the pressure and privilege of writing during high-stakes, high-emotion moments, and how Cody learned to write like it might be the only chance the audience would ever hear the speaker’s voice.

We also dive into how social media has completely reshaped the way speeches are received. How do you strike the balance between crafting a thoughtful message and creating a moment that cuts through the noise? Cody brings a grounded, behind-the-scenes perspective on that constant creative tension. Plus, we explore where speechwriting is headed next—from AI’s growing presence in the writing world to Cody’s work mentoring the next generation of communicators at Northwestern. He even gives us a peek into his life outside the spotlight—raising kids and staying inspired by the writers of tomorrow.

About Cody Keenan

Cody Keenan is Barack Obama’s former chief speechwriter and a current partner at Fenway Strategies. He spent over a decade crafting some of the most memorable speeches of the Obama presidency and now teaches political speechwriting at Northwestern University. Cody’s work has been featured on The Late Show with Stephen Colbert, Morning Joe, The Circus, and Pod Save America. A Chicago native and die-hard Cubs fan, he lives in New York City with his wife and two kids.

Sponsored by:
Delve.

It ingests every public mention across your online universe, then decodes and pushes it past the top-level insights to create real, usable intelligence. Top global companies and agencies already use Delve to stay ahead.
Learn more at delve.news/shift

Resources discussed in this episode:

• Grace: President Obama and Ten Days in the Battle for America by Cody Keenan
• Between Two Ferns with Barack Obama

Contact Allison Braley and Sean Garrett:

• MixingBoard.co
• LinkedIn: Allison Braley
• LinkedIn: Sean Garrett
• LinkedIn: Mixing Board
  
  

Contact Cody Keenan | Fenway Strategies:

• Website: codykeenan.com
• Website: fenwaystrategies.com
• Instagram: @codykeenan
• X: @codykeenan
• Facebook: Cody Keenan
• LinkedIn: Cody Keenan