AI Hope

Episode 7: Jeremy Wright on Building an AI That Actually Knows You 

Self Actual's CTO on self-honesty, feeling seen, and the year he was anti-AI

Jeremy Wright and I have known each other for two decades, dating back to the early social media days, and he has always been the one pushing further into the technology than the rest of us. In the AI arena, he’s continued that approach building Echo, an AI that didn’t mimic him online, it actually knew him: how he worked, how he showed up as a dad versus a co-founder versus a writer in creative mode. 

That project became the seed for Self Actual, the AI platform. Jeremy now serves as CTO, and the seat is staying open for him as they raise money.

Jeremy spent a stretch of his own life anti-AI, apologizing to people when he first started talking about what he was building. The shift came out of a hard year: aA major health crisis took him offline for months, his father was going through his own crisis at the same time, and when 

Jeremy came back online he stumbled into a friend's 30 Days of AI challenge with nothing but recovering brain energy and his own sideways way of working through things rather than following anyone's recipe. Two weeks in, he showed what he'd built to that same friend and got back the reaction that told him this was bigger than a personal project.

Watch or listen to Jeremy Wright on YouTube! Don't forget to subscribe!

Jeremy's insistence that building an AI that knows you requires knowing yourself first. I am impressed with the self-honesty it took to build Echo as much as the product itself. 

He told me about one of his most advanced users, whose Echo helped her realize she was autistic, and she cried for three days, not from sadness but from finally feeling seen. He is hopeful that an AI built to notices your flaws, and how to work with them rather than around them, is worth the conversation.

Listen today on Spotify, iTunes, YouTube, or wherever you get your podcasts!

0:34 Who is Jeremy Wright and what is Self Actual 
0:58 Building Echo, the AI that goes further than a digital twin 
1:52 The Jarvis analogy: an AI customized to you 
2:47 Jeremy's proudest AI success: the self-honesty it took to build Echo 
3:47 The AI skeptic who ended up building an AI company 
4:16 A health crisis, 30 Days of AI, and a two-week epiphany 
4:47 Wtfisecho.com and the sideways path to clarity 
5:41 The user who discovered she was autistic through Echo 
7:13 Where Jeremy sees AI benefiting society most 
7:54 Parting thoughts and how to connect

Fobby Naghmi, senior vice president at AnnieMac and a longtime podcaster in his own right, remembers the exact moment ChatGPT changed how he saw the world. He described it as the moment Christopher Columbus told everyone the world wasn't flat anymore. 

Fobby has spent the years since using AI as a genuine day-to-day tool rather than a talking point, in an industry that runs on paperwork, disclosures, and timelines that punish anyone who falls behind. Fobby doesn't think AI replaces mortgage professionals, he thinks the mortgage professionals who use AI replace the ones who don't. 

He's watched that gap widen inside his own team over the past year and a half. It's the same adaptation story that's played out since someone first hitched a horse to a cart, except this time the stakes show up in loan timelines instead of miles walked.

Fobby's read on where AI goes next in mortgage is less about automation and more about foresight, using AI to catch the fires in a loan file before they start rather than scrambling to put them out, and building AI agents into recruiting and client outreach so his own time opens up for the parts of the job that actually require a person. He's also watching regulation land, TCPA rules already apply and Fannie Mae's AI governance framework takes effect August 6th.

His hope for the industry, and for anyone listening, is straightforward: stop treating AI like a verdict on your career and start treating it like a tool, because a car can take someone to the hospital or it can do damage, and the tool was never the deciding factor. The technology doesn't decide who wins. The willingness to adapt does.

Listen today on Spotify, iTunes, YouTube, or wherever you get your podcasts!

1:20 The ChatGPT moment that changed how Fobby saw everything 

3:01 Why AI adoption will separate mortgage pros who thrive from those who don't 

4:25 His "now or never" moment diving headfirst into AI 

5:09 Using AI to catch the fires in a loan file before they start 

6:24 What Fannie Mae's incoming AI governance means for mortgage 

8:03 Fobby's advice: stop fearing AI, it's a tool like any other 

8:26 Where to find Fobby Naghmi

This week I interviewed David Berkowitz, founder of AI Marketers Guild and a longtime CMO now working with Mailchimp, about building real products without writing a line of code. Berkowitz shares a personal success story: teaching himself to ship landing pages, full sites, and usable products with AI tools, despite knowing only a sliver of HTML and none of the languages that make up a developer's toolkit.

David built his product line on Lovable, after starting with Base44, including Extra Lovable, a site that manages his other Lovable projects, and imfindable.com, a job search tool that went from idea to public launch in two days. He walked through why that speed changes the math entirely: a project that once cost tens of thousands of dollars and months of agency time now costs about fifty dollars in AI credits and a weekend of his own attention.

That thread runs through my own experience too, including a running clothes calculator built start to finish in four hours, and the two swap stories about how fast the ground has shifted since their social media days together. 

David also traces AI Marketers Guild back to 2022, when early access to the OpenAI Playground at Mediaocean produced a mock press release so convincing that his CMO thought it was too polished for an early beta model, months before ChatGPT ever launched. He closes with his hope for AI: unlocking the creative and analytical potential in people who never had the tools to bring their ideas to life before, and letting them finally bring their whole selves to their work.

Listen today on Spotify, iTunes, YouTube, or wherever you get your podcasts!

1:02 builtthatwithai.com Showcase 

1:31 Building Without Code 

2:32 Favorite AI Platforms 

5:09 Origin of AI Marketers Guild 

7:52 AI's Hope for Business 

9:04 Go Knicks

David on LinkedIn: https://www.linkedin.com/in/dberkowitz/

Build with That: https://highcaliberai.com/built-with-ai

AI Marketers Guild: https://aimarketersguild.com/

AI Hope Episode 4: Phil Gerbyshak on Surviving Teaching with AI

Geoff Livingston interviews Phil “Phil Gerb” Gerbyshak, a high school IT teacher and Substack writer, about using AI as a practical survival tool. Gerbyshak shares a personal success story: Walking into a new teaching role with no curriculum and using AI to navigate it. Phil used ChatGPT (plus some Gemini and Copilot) to build lesson plans, tests, and course materials for programming and video game design, saying he wouldn’t have made it through the year without it. 

Phil describes generally positive acceptance from fellow teachers, contrasts that with backlash he’s seen in marketing, and attributes resistance to fear and job-loss anxiety amid layoffs. He also discusses using AI as a developmental editor for his upcoming book, Slow Happiness (expected in October), and closes with a “happy tip” to slow down and enjoy life.

01:50  Teachers Embrace AI

03:11 Marketing Backlash

06:00 Slow Happiness Book

07:06 AI as Editor

08:46 Hopes for AI

09:25 Happy Tip 

Follow Phil on Linkedin: https://www.linkedin.com/in/philgerb/

Phil’s Happiness Practices project: https://happyaf.substack.com/

Geoff Livingston interviews Lindsey Mastis, a former broadcast journalist who became one of the first to cover AI as a regular beat and now trains others on using AI while speaking on social good at conferences, including in Geneva and at the UN. 

Mastis shares a personal AI success story: using an LLM to plan a winter trip to Greec. She also shares using AI tools for self-coaching, translating her family history into Greek, and communicating via translation apps to connect with her ancestral “martyr village,” meet locals, and speak with a survivor who fled as a child during wartime fires. 

She recalls ChatGPT’s launch as a “now is gone” moment that reignited the excitement she once felt for augmented reality, contrasting it with newsroom resistance to new technology. Mastis is most optimistic about medical AI, citing at-home diagnostic tools and augmented-reality-assisted training that could reduce medical errors and unnecessary ER visits.

01:30 AI Trip Planning Greece

02:50 Finding Ancestral Village

05:46 ChatGPT Beat Breakthrough

07:55 Newsroom Resistance to AI

09:16 Hopeful Future Medical AI

You can find Lindsey on LinkedIn here.
Check out her company Blue Moves Media here.

AI Hope Episode 2: Jeannie Walters on AI, Customer Experience, and the Human Moment

Jeannie Walters, USA Today bestselling author of Experience Is Everything and founder of Experience Investigators, joins Geoff Livingston for the second episode of AI Hope. They explore how AI is reshaping customer experience, from journey mapping to the front lines of healthcare.

Walters shares her AI home run: using vibe coding tools like Lovable to rapidly prototype ideas as a founder, turning concepts into working demos that her team can then refine, which is dramatically accelerating how she brings her vision to life.

They discuss using AI as an accelerant for customer journey mapping, warning against organizational paralysis in pursuit of perfect, end-to-end maps when a back-of-the-napkin exercise can spark faster action. Walters emphasizes that AI's real power is in pattern recognition and turning data into insights, but only when anchored to a clear mission and measurable goals.

Walters also shares her vision for AI in patient experience, highlighting how AI can remove administrative friction like delayed lab results or heads-down documentation. Instead, she sees a future where AI frees clinicians to be fully present for more human, meaningful interactions.

Listen Today!

You can follow Jeannie on LinkedIn: https://www.linkedin.com/in/jeanniewalters/

Get Experience Is Everything at every major bookstore.

Learn more about her business and book at experienceinvestigators.com

AI Hope Episode 1: Reaching Higher with Purpose featuring Aaron Strout

Aaron Strout, author of Wired for Purpose, joins Geoff Livingston on Episode 1 of AI Hope to discuss humanity as a differentiator in a digital world and how to approach AI with rational optimism amid reactive, toxic social media. 

Strout shares early lessons using generative AI tools, both helpful outputs and hallucinations then describes how AI now acts as a thought partner that saves him significant time across his work, podcasting, and content creation.

 They discuss staying calm under pressure (“flight attendant energy”) during Now Is Gone moments, experimenting with AI tools without getting attached to any single platform, and encouraging people to start using accessible AI like Gemini. 

Strout outlines AI’s potential in healthcare, including freeing clinician time, enabling synthetic trials and real-world data analysis, and accelerating pattern-finding and research, emphasizing technology-led but human-guided use
 
 Aaron is on an East Coast mini book tour to Washington, DC, New York and Boston (6/16-18). Get more details on his book site:  https://getwiredforpurpose.com/

You can follow Aaron directly on LinkedIn here: https://www.linkedin.com/in/aaronstrout/

And you can listen to the Reaching Higher Podcast here: https://reachinghigherpod.com/