AI Literacy for Entrepreneurs – Details, episodes & analysis

Should you build custom GPTs, agents, digital interns, Gems, and artefacts… or just learn to prompt better? In this roundtable, Susan, social media + AI power user Andrew Jenkins, and GTM + custom GPT builder Dr. Jim Kanichirayil unpack when you actually need a custom build, when a strong prompt is enough, and how to stop treating AI output like a finished product.

In this episode, Susan brings back two favourite guests who sit on different ends of the AI usage spectrum:

• Andrew Jenkins - multi-tool explorer, author, and agency owner who "puts the chat in ChatGPT" and loves talking with his data.

• Dr. Jim Kanichirayil - founder of Cascading Leadership, builder of thought leadership custom GPTs for go-to-market, content, and analysis.

Together they break down:

• How Andrew uses conversation, prompt optimizers, projects, and tools like NotebookLM and Dojo AI to "talk to" his book, podcast, and data.

• How Dr. Jim uses a simple Role-Task-Output framework to design custom GPTs, train them on his voice (and the voices of his clients), and keep them on track with root-cause analysis when they drift.

• The messy reality of limits, context windows, and why AI is still terrible at telling you what it can't do.

• Why using AI on autopilot (especially for outreach and content) is a brand risk, and how to use it as a drafting and analysis system instead.
  
  

Key takeaways

You don't have to choose only prompts or only custom GPTs.
Strong prompting is the starting point. Custom GPTs make sense when you see the same task, drift, or "bleed out" happening over and over again.

Start every workflow with three things: Role, Task, Output.
Who is the AI supposed to be?
What exact job is it doing?
What should the output include and exclude?
Then ask the model: "What else do you need to execute this well and in my voice?"

Knowledge bases are just your best examples and instructions in one place.
Transcripts, scripts, PDFs, posts, style packs, platform-specific examples - they're all training material. AI does best when you feed it gold standard samples, not vibes.

Projects and talking to your data are the future of reading and research.
Andrew uses his entire book in Markdown as a project, then has conversations like "find me five governance examples" instead of scrolling a PDF. NotebookLM turns bullet points into decks, mind maps, and videos, then lets you interrogate them.

AI is a 60-70% draft, not a finished product.
If you post straight from the model, it will sound generic, over-written, and slightly robotic. The job is to take that draft and ask: "Does this sound like me? Would I actually say this?"

Automation is good. Autopilot is dangerous.
Using AI to analyze content performance, structure research, or standardise parts of a workflow = smart.
Letting AI write content and outreach you never review = reputation risk and audience fatigue.

More content is not the goal. Better feedback loops are.
Dr. Jim chains GPTs: one for drafting with his voice, one for performance analysis, one for insights. That loop makes the next round of content sharper instead of just… louder.

Episode highlights

[00:13] The core question: build digital interns (agents/custom GPTs) or just prompt better?

[01:09] Andrew's origin story and why he "puts the chat in ChatGPT."

[03:39] How Andrew uses prompt optimizers, multiple models, and Dojo AI as an agentic interface.

[07:24] Dr. Jim's world: sticking to GPT, building tightly scoped custom GPTs for repetitive work.

[08:37] When "bleed out" in prompts tells you it's time to build a custom GPT.

[09:26] Using root-cause analysis inside the GPT configuration when outputs go off the rails.

[10:25] Projects, books in Markdown, and "talking to your own material" via AI.

[13:05] Case study: using AI to surface case examples from a 3.5-year-old book instead of scrolling PDFs.

[14:27] NotebookLM for founders and students: one email of bullet points → infographic, map, slide deck, video.

[19:03] The Role–Task–Output framework and the importance of explicitly designing for your voice.

[22:02] Platform-specific style packs and use cases (spicy vs informational vs editorial).

[26:29] The frustrating reality of token limits and why models rarely warn you before they hit a wall.

[36:54] What's happening "in the wild": early-stage founders treating AI output as final product.

[39:01] Why "more" isn't better, "better" is better: drafts, polish, and content analysis GPTs.

[42:03] Automation vs autopilot in B2B social, and why Andrew refuses to buy from a bot.

[43:29] Emerging tools: Google's Pommely, Nano Banana for image creation, and AI browsers like Atlas, Comet, and Neo.

If you've been stuck wondering whether to spend time on custom GPTs or just prompt better, this episode gives you the mental models to decide.

Share it with:

• The teammate who keeps saying "we should build a GPT" but hasn't defined the workflow.

• The founder treating AI drafts as finished copy.

• The ops brain in your org who secretly wants to be a bridge builder.
  
  

Then ask as a team: "Where do we actually need great prompts, and where do we need a repeatable GPT or project with a real knowledge base?"

Connect with Susan Diaz on LinkedIn to get a conversation started.

Agile teams move fast. Grab our 10 AI Deep Research Prompts to see how proven frameworks can unlock clarity in hours, not months. Find the prompt pack here.

You may have heard host Susan Diaz say she "swan dove backwards off the cliff into AI". In this episode, she unpacks what that actually means, how it became the working title of her book, and the concrete frameworks leaders can use to move boldly into AI without being reckless.

This is a personal, behind-the-scenes episode.

Susan shares how she went from not being in the famous first 6 million users of ChatGPT… to becoming the person who showed up a week later and refused to leave.

She explains why generative AI felt different from every underwhelming AI-ish tool she'd used before.
Then she introduces two big ideas that will run through the book and the podcast series:

• The four cliff archetypes of AI in organizations.

• The five moves of a swan dive that turn bold experimentation into lasting infrastructure.

It's part origin story, part field guide, and part invitation to join the Early Divers instead of waiting for the bridge to magically appear.

Key takeaways

Generative AI was a pattern-breaker. What hooked Susan wasn't hype. It was the combo of: credible output, ability to handle large volumes of messy information, and being free to use. That trifecta changed the game for everyday operators.

"Swan dive backwards" is not recklessness. It's a personality pattern. Quick starts jump with a scan for rocks and a plan to tuck their elbows. The instinct is to move, not freeze, when the path ends.

Every organization has four cliff archetypes of AI:

1. Divers - the early experimenters pressing all the buttons.
   
   

2. Pathfinders - the risk-mappers and governance folks asking "how do we do this safely?"
   
   

3. Operators - the people who turn experiments into actual workflows and pilots.
   
   

4. Bridge builders - the systems people who turn one-time wins into playbooks, platforms, and training.

You are rarely just one archetype. You're more like a sound mix across all four. That mix determines how you respond when AI shows up as a cliff, not a gentle slope.

The five moves of a swan dive give you a pattern:

1. Spot the cliff - recognize this is a step-change, not another incremental tool.
   
   

2. Check the water - test, set guardrails, understand risks and boundaries.
   
   

3. The dive - move out of analysis into real use on real work.
   
   

4. Surface with a map - name patterns, document what's working, share stories.
   
   

5. Build the bridge - turn what you learned into infrastructure so others don't have to jump cold.
   
   

AI is too big to leave to one personality type. Divers alone will splatter. Pathfinders alone will stall. Operators without bridge builders will create one-off wins that never stick. You need all four.

This book and series are a public swan dive. Backwards! The 30-episode challenge, the naming of Swan Dive Backwards, and the frameworks are all being built where others can see and eventually walk the bridge.

Episode highlights

[00:00] "I swan dive backwards off the cliff into AI" - why that line sticks and what it actually means.

[01:19] Naming the book Swan Dive Backwards and the meta moment for future readers.

[01:47] Why Susan was not in the first 6 million ChatGPT users, and why early AI tools had underwhelmed her.

[03:03] The three markers that made generative AI different: credible output, large-volume handling, and being free.

[05:27] "Late to the party, then refused to leave" – how personality type shaped her AI journey.

[06:28] The cliff analogy: divers, plotters, doers, bridge builders.

[09:33] Why Susan is a classic "diver" and how that shows up in entrepreneurship.

[12:08] The LinkedIn comment from Alison Garwood-Jones that locked in the book title.

[14:53] The four cliff archetypes of AI inside companies, in explicit AI terms.

[18:38] Move 1: spotting the cliff – realising AI is a calculator/PC-level shift, not a passing tool.

[19:44] Move 2: checking the water – personal tests, failures, and organisational governance.

[20:45] Move 3: the swan dive – moving from theory to workflow-level experiments.

[21:50] Move 4: surfacing with a map – turning experiences into language, frameworks, audits.

[23:03] Move 5: building the bridge – connecting experiments into ongoing systems and training.

[23:31] Why the real courage is building so others never have to jump cold again.

This episode is both an origin story and a mirror.

Ask yourself and your team

1. Which cliff archetype do you lead with: Diver, Pathfinder, Operator, or Bridge Builder?

2. Where are you on the five moves of the swan dive: staring at the cliff… or quietly building the bridge?
   
   

Share this episode with the biggest "diver" you know and the most trusted "pathfinder" in your organization.
They're going to need each other.

Connect with Susan Diaz on LinkedIn to get a conversation started.

Agile teams move fast. Grab our 10 AI Deep Research Prompts to see how proven frameworks can unlock clarity in hours, not months. Find the prompt pack here.

AI search is here. People are using ChatGPT and other tools to discover businesses - but my guest today on the podcast, Andrew Jenkins shows why the foundations of SEO still matter. Andrew is CEO of Volterra Digital, a top-ranked social media agency, and a long-time member of my Marketing Power Circle (MPC).

We dive into:

• Why getting found on AI isn't a "flip the switch" formula

• The role of reviews, backlinks, and industry recognition in AI search rankings

• How Andrew used Clutch.co to build a discoverability flywheel

• How custom GPTs and vibe coding are transforming small agency workflows

• The mindset shift from AI as content spam to AI as your second brain
  
  

🔗 Connect with host, Susan Diaz on LinkedIn.

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🚀 Ready to go beyond inspiration into implementation?

That's exactly what we do inside Marketing Power Circle (MPC) - my AI implementation mastermind.

It's where founders, consultants, and in-house leaders stop doomscrolling and start doing:

• Building custom GPTs for their workflows

• Repurposing content at scale

• Designing intelligent automations that buy back hours every week

• And most importantly, experimenting with AI in a supportive, peer-driven community
  
  

✨ If you've been watching AI from the sidelines, MPC is the room where it happens. 

It's the only AI implementation mastermind designed for small business teams. 

Learn more here.

 

To kick off a fresh year's dishing sessions on marketing news, Susan is joined by mindset mentor and performance coach Megan O'Neill. What's hot this week? 👇

New Day's Lyric

One of our favourite rising stars, poet Amanda Gorman, made 2021 her own in a whirlwind of events from the US presidential inauguration, to the Met Gala, to the Superbowl, all while snagging a groundbreaking contract with Estée Lauder and penning 3 number 1 bestselling books. Now to ring in the new year, in partnership with Instagram, Amanda has released her latest poem, 'New Day's Lyric' in beautiful video form. The poem speaks of hope, love, and connection.

Pizza Hut Canada decides to make the decision to get decisive about roasting Premier Ford

After yet another lockdown announcement that left us with many many SMH moments, many people took to social media to air their grievances with Ontario Premier Doug Ford. As we love to see happening these days, we caught on to a little bit of Twitter newsjacking brought to us by none other than Pizza Hut, who cheekily took a popular term from the speech that one clever and entertaining step further.  

2021 takes our Golden Girl

As if 2021 didn't already take our sanity, on the last day of the year the legend Betty White passed away at the age of 99. She has touched every generation from her start in show biz. If there was anyone that should have lived forever, based solely on the fact that she was so universally loved, it was Betty. Knowing how wonderful she was, she probably just didn't want to sully the new year with such sad news 😢 We'll miss you, Betty! 

The science of climate humour

The movie Don't Look Up has been popular thanks to its cast of big stars, but it's also raised some questions about its satirical coverage of climate change and politics. Since the topic of climate change is so serious, is it really appropriate to joke about it? In short, yes! We are all about the EQ (Entertainment Quotient) around here, and agree with Canadian comic Leonard Chan who believes that the closer the humour is to crisis or upheaval, the better the humour has to be. Write well, use your common sense, and have some fun!

We've reached the end of 2021, yo. 
The last few days of the year. 

It's been a mixed bag for many people. That said, the one big thing that emerged this year is a deep need for self-care. 

A deep need to renew, rejuvenate, take care of yourself, take care of your mind, your body, and your spirit. 

In this episode, we have tips from three awesome specialists in the health and wellness space, who will speak to different aspects of taking care of the mind, body, and spirit. Pick a practice, and focus on building it in 2022. Good luck! 

 

The art of mindful doodling to relieve stress

Melissa Lloyd, founder and chief doodler at DoodleBreaks points out, we are all born with creativity. And yet, many if not most of us lose that natural urge to doodle. 

Allow your mind to float, and your anxiety settle. 🧠 🧠 🧠

 

The art of slow motion multitasking

​​Zannat Reza is a registered dietician and ambassador in the healthy aging space. She spends her waking hours helping organizations strategize and create memorable food & health content that inspires, educates, and empowers people to live their best lives. She delves into Slow Motion Multitasking.

🧠 🧠 🧠

 

The art of good sleep

Lydia Di Francesco is the CEO and Wellness Consultant at Fit + Healthy 365.  As a workplace wellness consultant, she helps companies understand the connection between well-being and mental health, and employee productivity and retention. 👏👏👏

She advises:

💫 Setting boundaries.
💫 Building what she calls "stress resilience."
💫 Exercise and healthy eating to equal better sleep.

This week, we round up the short episode-arc in which we're spotlighting trends that really dug deep roots into 2021, and will certainly be around to play with in 2022 and beyond. 

Our source of input (delicious at that!) is our weekly live roundup of marketing news, which I co-host with various industry leaders on what's happening in the marketing world, and what we can learn from it. That live round-up is what becomes the podcast, here, for your fine folx!

Through doing that every week on Thursdays, we uncovered some stuff that came up over and over again.

And among those are NFTs. An NFT, for the uninitiated, is a non-fungible token, which is a kind of digital asset to which a cryptocurrency value is assigned. 

It's an asset that you definitively own in the digital space. 

And, broadly, there are a couple of things to know in the space, regardless of your familiarity with the subject.

Know that there's an origin story that comes with an NFT.

This means that if you have an NFT, it belongs to you. You can clearly trace who the thing belongs to via blockchain. And therefore it has huge implications for intellectual property and for creators. 

If NFTs are not something that you want to directly think about right away, don't forget to educate yourself for when you need it.

Whether or not you are getting into the world of NFTs right this second, do educate yourself because there's room to get involved in discussions. There's room to get into collaborations. There's room to see how this all works for your industry, and still be among the early adopters, even if your brand isn't cracking open an NFT right away. 

Happy new year 2022! We can't wait to see what the year brings.

🎧Tune in to hear more!🎧

If you're a repeat visitor to our podcast, please drop us a 5 star review. Thank you!

We continue this mini episode-arc, focusing on some of the key themes that ruled this year on the marketing front, and will reign in 2022. 

We draw your attention to 2 phenomena that are noteworthy, to inspire you as you head into a whole new year of marketing ahead of you.

The first is #freebritney - keep reading! 

The Free Britney movement was created by Britney Spears' fans. 

What started as a hashtag eventually freed Britney from the conservatorship of her father this year! The story is compelling.

The phenomenon that will rule amongst the masses in 2022 is TikTok. Some trends that dominated in 2021 were feta pasta and true crime.

How does this break down to B2B?

We tell you how to incorporate TikTok even if you 'don't dance'. As well as how to really clue into music and think like a creator (or just hire one 😁)

🎧Tune in. Listen up!🎧

If you're a repeat visitor to our podcast, please drop us a 5 star review. Thank you!

We continue this week with our episode arc around what we can learn from winning examples of marketing in 2021 as we head into 2022. 

The categories and channels of marketing have changed.
Where's your innovation going to come from? 

Today, we wanted to dive deeper into the subject of newsjacking. One of the things that has proved successful for brands over and over again during the pandemic is newsjacking. 

Marketing is no longer a one-way, broadcast-only model. What really gets noticed is agility - being able to get involved in conversations, and do it fast. It's certainly the only thing that stands out on social media! 

In 2021 brands excelled at newsjacking.
It's easy to assume that the brands in question are always like the big enterprises and the B2C brands - like the fast food chains certainly do it. 

That said, those are not the only brands that have newsjacked effectively; that have made it their purpose to get out there and get social. 

There was Bernie Sanders and the mittens from the US presidential inauguration. Every brand used that meme eventually! 
Senator Sanders' own team got involved and used the traction to raise funds for charity. 

That said, special mention to one of the Canadian geniused in this category! 
Ottawa Public Health! 

They created the character 'Bruce' And it went viral. Even Ryan Reynolds got involved! They are small municipal level government account, and they've done some amazing work in newsjacking. 

What can you learn from those examples? 

Take a listen!

This week Susan is joined by Colleen O'Connell-Campbell, Wealth Advisor at RBC Dominion Securities, and host of 'I'm a millionaire. So, now what?' 🎙

Budweiser NFT sells out   If you've been wondering 'wassuuuuup' with Budweiser lately, you'll be excited to hear that they've moved into the metaverse, releasing a brand new collection of limited edition digital art known as the 'Heritage Collection'. 1,900 "Core Heritage Cans" at $499 each and 36 "Gold Heritage Cans" at $999 each sold out within an hour.   Hiring in the metaverse   No longer just for gamers, the metaverse is now beginning to be used by companies like Hyundai and Siemens to help hire people in an immersive environment. Thanks to Facebook changing its name to Meta, people are now really paying attention to the metaverse and accepting that this new world is going to become mainstream.   Governor General's awards for some of our fave stars   Proudly Canadian actors Catherine O'Hara and Ryan Reynolds were recently awarded Governor General's Performing Arts Awards. Thanks to the miracle of YouTube we were able to share in their reactions as they were honoured via serenade, Ryan by singer Steven Page, and Catherine by her Schitt's Creek costar Noah Reid. Their genuine reactions are so adorable we promise you'll get something in your eye if you give them a watch.    Twitter Transforms   Jack Dorsey, CEO of Twitter, resigned earlier this week and will be replaced by former CTO Parag Agrawal. Some changes were immediate. A huge can of worms was opened with the announcement of new privacy policies relating to the sharing of unowned images and we're really having hard time believing this will be sustainable for Twitter.   Shopify tops the pack for sales   The post Black Friday/Cyber Monday stats are in and it looks like shopping is down all across the board - except on Shopify. Colleen's take is that people are really trying to find that balance between supporting small businesses while also having it be convenient. As consumers, where we spend our money is the way we express how we want to shop, so we're seeing consumers empowered to support local and  smaller business.   For these stories and more, including what's happening in the business world after Black Friday, listen to the whole episode.    

In this episode arc, we're going to focus on some specific trends and learnings that you can take with you going into 2022 in your marketing.

This is a significant inflexion point in the evolution of the way we communicate, market, and sell.

Things have changed a lot during the pandemic with a whole new virtual world open. 

The things we thought to be the vehicles or tools of marketing distribution have changed. 

What's getting attention? 
What is really cutting the scroll? 

We break down 2 key things to focus on. 

1. The categories of distribution of content marketing
2. New examples to be inspired by that you won't find traditional marketing books because things are moving so fast.

Take a listen.

We are joined by 6 guest judges.

Andrea Henry, founder of Henry business law. 
We have Darien Kovacs, founder of jelly marketing. 
We have Megan O'Neill, performance coach. 
We've got Martin Waxman, instructor at University of Toronto and PR expert. 
Mohit Rajhans, media commentator and founder of thinkstart
And Rohini Mukherji, Vice President at narrative PR 

If you're a return listener, please leave us a 5-star review? Thanks 💫