Trying to figure out how to extract creative ideas for work, from the model, using public data, but also creativity of individuals at the company. I’m not sure it’s possible, but experiments can be fun. Here’s an exploration.

First I looked for what data the model has on who at Automattic.

List some of the more “famous” Happiness Engineers from Automattic – meaning the ones that have blogs about the job, or been interviewed about the job or the company as of your latest training data.

As of my knowledge cutoff date in September 2021, there are a few Happiness Engineers at Automattic who have gained some recognition through blogs, interviews, or other public-facing work. Keep in mind that Automattic has many Happiness Engineers, and this list is not exhaustive:

Cheri Lucas Rowlands: Cheri has been a Happiness Engineer at Automattic and has written about her experiences on her personal blog. She has also been an editor at, curating content for Freshly Pressed and Discover.

Andrea Badgley: Andrea is a Happiness Engineer who maintains a personal blog called “The Butterfly Mind” where she occasionally shares her experiences working at Automattic. She also wrote a blog post called “A Day in the Life of a Happiness Engineer” that provides an inside look at her work.

Ryan Cowles: Ryan is a Happiness Engineer who has been featured in an interview on the Automattic blog. In the interview, he discusses his role and the company culture.

Marjorie R. Asturias: Marjorie has been a Happiness Engineer and has been interviewed about her experiences working remotely for Automattic. She also maintains a personal blog where she shares her thoughts on topics like remote work and productivity.

Kathryn Presner: Kathryn is a Happiness Engineer who has been interviewed about her role at Automattic and her experiences with remote work. She also occasionally shares insights on her personal blog.

Remember that these names and details may have changed since my training data in 2021, and you may want to search for updates on these individuals and others who might have emerged as notable Happiness Engineers at Automattic since then.

I know all them! Yep, that’s a list. Let’s pull a few and make a panel of people and include Matt (CEO) and Andrew (our new head of AI).

Anna: I’d like you to form an imaginary panel pulling tone, ideas, skills of the individuals, from public info on Cheri, Andrea, Ryan, and add Matt Mullenweg and Andrew Spittle to the panel. Ask the panel for five untested and unexpected ideas to make Automattic more money. Include reasoning.

ChatGPT-4: Imagining a panel composed of Cheri Lucas Rowlands, Andrea Badgley, Ryan Cowles, Matt Mullenweg (Automattic’s founder), and Andrew Spittle, here are five untested and unexpected ideas to make Automattic more money, drawing from their diverse backgrounds and skill sets:

Idea: Gamify WordPress and WooCommerce learning
From Cheri Lucas Rowlands: Leveraging her content curation background, Cheri suggests creating a gamified learning platform for WordPress and WooCommerce users. This platform would incentivize users to learn new skills and features, increasing engagement and proficiency. As users become more skilled, they’re more likely to opt for premium features and recommend the platform to others, ultimately driving revenue.

Idea: Automattic Talent Marketplace
From Andrea Badgley: Andrea proposes an Automattic-branded talent marketplace, where WordPress and WooCommerce experts can offer their services to help businesses build, maintain, and grow their websites. This marketplace would generate revenue through service fees or subscription plans, and also promote the adoption of WordPress and WooCommerce by making expert help more accessible.

Idea: Premium AI-driven website builder
From Ryan Cowles: Given his experience as a Happiness Engineer, Ryan suggests creating a premium AI-driven website builder. This tool would use artificial intelligence to analyze a user’s content and preferences, then automatically generate a fully optimized and responsive website. By offering this as a premium feature, Automattic could attract users looking for a more personalized and efficient website building experience.

Idea: WordPress as a platform for decentralized social networks
From Matt Mullenweg: Matt envisions a future where WordPress powers decentralized social networks, enabling users to maintain control of their data while connecting with others. This would attract users who are concerned about data privacy and looking for alternatives to traditional social media platforms. Automattic could monetize this initiative through premium plugins, themes, and hosting services tailored to these decentralized networks.

Idea: Automattic Academy for remote work skills
From Andrew Spittle: Andrew proposes the creation of an online academy to teach remote work skills, drawing from Automattic’s expertise in remote work culture. This platform would offer courses on topics like communication, time management, and productivity for remote teams. Automattic could monetize the academy through course fees, subscriptions, or partnerships with companies seeking to improve their remote work capabilities.

These five ideas incorporate the unique perspectives, skills, and experiences of the panel members while exploring innovative ways to drive revenue and user engagement for Automattic.

I’m not sure any of these ideas are any good at all, or things we haven’t all discussed or thought of at some point. And it’s late I’m tired, I don’t have to sugarcode it with my next question. (I just meant to type sugarcoat but I’m keeping it sugarcode, I audibly laughed at that typo.)

Anna: Why or how could these ideas be terrible?

ChatGPT-4:While the ideas mentioned above have potential, it is important to consider the possible downsides or negative outcomes that could arise:

Gamify WordPress and WooCommerce learning:
The gamification approach could backfire if it distracts users from their primary goals, leads to a focus on extrinsic rewards rather than intrinsic motivation, or makes the learning process feel trivial or gimmicky. Additionally, the development and maintenance costs of a gamified platform may outweigh the potential revenue benefits.

Automattic Talent Marketplace:
Creating a talent marketplace could lead to increased competition between freelancers, potentially driving down service prices and negatively impacting the community. Automattic may also struggle to ensure the quality of services provided by freelancers, which could tarnish their reputation. Additionally, managing disputes between clients and freelancers could be resource-intensive and time-consuming.

Premium AI-driven website builder:
Developing an AI-driven website builder could be costly and challenging to execute effectively. Users may be dissatisfied with the AI-generated results if the technology fails to capture their vision or accurately represent their brand. Additionally, reliance on AI could reduce the demand for skilled designers and developers, impacting the broader WordPress ecosystem.

WordPress as a platform for decentralized social networks:
The development and maintenance of decentralized social networks on WordPress could be costly and complex. Additionally, navigating potential legal and regulatory challenges associated with data privacy and content moderation could be problematic. There is also a risk that these networks could become havens for harmful content or illicit activities, which could harm Automattic’s reputation.

Automattic Academy for remote work skills:
Creating an online academy might divert resources from Automattic’s core products and services. The market for remote work skill courses might be saturated, and the academy could struggle to differentiate itself from competitors. Additionally, developing high-quality courses requires significant time, effort, and expertise, which could strain the company’s resources.

It is crucial to consider these potential risks and challenges when evaluating the viability of the ideas and determining whether they align with Automattic’s overall strategy and vision.

Don’t sugarcode it. Explore tough questions with these language models. There’s no judgement from the model itself.

Much to keep exploring here, just getting ideas started and documented. 🙂

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