Building Jason wasn’t some grand tech startup story where I had a brilliant idea in the shower and coded it up over a weekend. Honestly? It was messier than that. Way messier.
Every single feature in Jason exists because I screwed something up first. And I mean really, spectacularly screwed up in ways that cost me time, clients, and quite a bit of my sanity.
Let me pull back the curtain on how my biggest mistakes became Jason’s best features.
The Client Disaster That Started Everything
February 2024. I’m working with this marketing agency on a campaign for their biggest client – a regional healthcare system. They need social media content that feels authoritative but approachable. Medical expertise without being intimidating.
My prompt to ChatGPT: “Write social media posts about preventive healthcare that sound professional but friendly.”
The result? Generic health tips that could’ve come from any wellness blog. “Eat your vegetables!” “Exercise regularly!” “Get enough sleep!”
Nothing about their specific services. Nothing that positioned them as local healthcare experts. Nothing that would make someone choose them over the hospital down the street.
The agency director looked at my work and said, “This could be for any healthcare system anywhere. Where’s their voice? Where’s what makes them different?”
I had no answer. Because my prompt had no voice, no differentiation, no specific positioning. Just vague instructions that led to vague content.
That humbling moment became the foundation for Jason’s Brand Voice Analyzer feature.
The Night I Almost Quit
Three weeks after the healthcare disaster, I’m up at 2 AM working on content for a local restaurant chain. Five locations, each with slightly different vibes. The downtown spot attracts young professionals. The family location draws suburban parents. The college town restaurant serves late-night crowds.
My brilliant strategy? Use the same prompt for all five locations and just change the restaurant name.
“Write Instagram posts for [Restaurant Name] that showcase their atmosphere and food.”
The results were identical except for the names. Same generic food photos descriptions. Same “come dine with us” messaging. Same everything.
When the owner saw the content, he was confused. “Why does my family restaurant sound exactly like my college bar? They’re completely different places serving different people.”
He was right. I’d completely ignored that context matters – not just for the brand overall, but for specific locations, audiences, and situations.
That failure led to Jason’s Context Layering System. Instead of one-size-fits-all prompts, Jason asks about specific audience segments, locations, situations, and goals. Then it builds prompts that account for these nuances.
The Email Campaign That Taught Me About Timing
May 2024 was rough. I’m helping this online course creator launch their new program. She’s in the personal development space, working with people who’ve been burned by other “gurus” and are skeptical of big promises.
My email sequence prompts were all over the place:
- “Write a launch email that gets people excited”
- “Create urgency for the course enrollment”
- “Send a testimonial email that builds trust”
Each prompt treated every email like a standalone piece instead of part of a coordinated sequence. The tone shifted randomly between messages. One email was super enthusiastic, the next was cautious and trust-building, then back to hype mode.
My client’s audience was confused. The emails felt like they were written by different people with different agendas.
“These emails don’t flow together,” she told me. “It’s like my personality changes every time I email my list.”
That’s when I realized prompts needed to understand sequential context – how each piece of content relates to what came before and what comes next.
Jason’s Sequential Prompting feature now asks about content series, campaign goals, and how individual pieces fit into larger strategies. No more jarring tone shifts or disconnected messaging.
The Product Launch That Almost Bombed
June brought its own special kind of disaster. I’m working with this small software company launching a project management tool. They’re competing against giants like Asana and Monday.com, so positioning is crucial.
My product description prompts were disasters: “Write about project management software features” “Create copy that explains why this tool is better” “Generate marketing content for small businesses”
The results? Feature lists that sounded like every other PM tool. Benefits that could apply to any software. Nothing that explained why someone would choose this specific tool over established competitors.
The founder read my work and sighed. “This makes us sound like everyone else. What about our story? What about why we built this differently?”
Their story was actually compelling – they’d built the tool because existing solutions were too complex for small teams. But my prompts never captured that narrative.
That experience created Jason’s Differentiation Engine. It asks specific questions about competitive landscape, unique value propositions, origin stories, and target market pain points. Then it builds prompts that highlight what makes each brand genuinely different.
The Social Media Disaster That Nearly Ended a Friendship
This one still makes me cringe. My friend Lisa runs a boutique fitness studio specializing in prenatal and postnatal workouts. Super niche, very specific audience needs, requires a lot of sensitivity and expertise.
My social media prompts treated her business like any generic gym: “Create fitness motivation posts” “Write about workout benefits”
“Generate content about staying healthy”
The resulting content was tone-deaf. Generic fitness motivation for women dealing with pregnancy symptoms. Workout tips that ignored physical limitations new moms face. “Push through the pain” messaging for people who need to listen to their bodies more than ever.
Lisa was horrified. “This doesn’t understand my clients at all. Pregnant women can’t just ‘push harder’ – that could be dangerous.”
She was absolutely right. My prompts had no awareness of the specialized knowledge her audience needed or the trust required in her particular market.
That wake-up call led to Jason’s Audience Sensitivity Scanner. It identifies when content needs specialized expertise, cultural awareness, or extra care around sensitive topics. Then it builds prompts that account for these considerations.
The Blog Series That Made No Sense
August was particularly educational in all the wrong ways. I’m helping a financial advisor create a blog series about retirement planning. Should’ve been straightforward – break down complex topics for regular people approaching retirement.
My approach? Individual prompts for each blog post with no connection to the others:
- “Write about 401k basics”
- “Explain Social Security benefits”
- “Create content about retirement timeline”
Each post was fine in isolation. But together? They made no sense as a series. Information was repeated randomly, topics weren’t introduced in logical order, and the complexity level jumped around unpredictably.
Readers were confused. “Why are we talking about advanced investment strategies in post two, then explaining what a 401k is in post four?”
That’s when I understood that content series need architectural thinking – careful sequencing, logical progression, and consistent complexity levels.
Jason’s Content Architecture Planner now maps out how individual pieces fit together, ensuring logical flow and appropriate information sequencing.
The Crisis That Created the Emergency Feature
September brought my most stressful client situation ever. A local business faced a minor PR crisis – nothing major, but they needed to respond quickly and appropriately to social media backlash.
My crisis communication prompts were completely inadequate: “Write a response to negative comments” “Create an apology that sounds genuine”
The generated responses felt corporate and disconnected. They ignored the specific concerns people raised and used language that made the business sound defensive rather than understanding.
When your business reputation is on the line, you can’t afford generic crisis communication. You need responses that address specific concerns, match your brand voice, and actually resolve the underlying issues.
That crisis led to Jason’s Situation-Specific Prompting. It includes templates for sensitive situations like customer complaints, PR issues, difficult conversations, and crisis communication. Each template accounts for emotional context, stakeholder concerns, and desired outcomes.
The Feature That Came from My Own Laziness
By October, I’d been manually building complex prompts for months. I was getting better results, but it was taking forever. I’d spend 15 minutes crafting a single prompt, then another 10 minutes refining it based on the output.
The irony wasn’t lost on me – I was using AI to save time, but spending more time writing prompts than I used to spend writing content.
That’s when I built Jason’s Smart Template System. Instead of starting from scratch each time, it learns from successful prompts and suggests frameworks based on content type, industry, and goals.
Now what used to take 15 minutes takes 2 minutes. And the results are consistently better because the templates incorporate all the lessons I learned from months of failures.
The Testing That Almost Broke Me
November was testing month. I’d built all these features, but did they actually work for people who weren’t me?
I gave Jason to 20 different content creators and watched them use it. The results were… humbling.
People kept trying to use it like every other prompt tool – typing in vague requests and expecting magic. They’d skip the context questions, ignore the audience analysis, and wonder why their results weren’t amazing.
That’s when I realized Jason needed guided workflows. Instead of dumping features on users, it needed to walk them through the thinking process that creates great prompts.
The current version doesn’t just generate prompts – it teaches users why certain elements matter and how different contexts change prompting strategies.
What All These Failures Taught Me
Every disaster, every client disappointment, every late-night panic session contributed to making Jason more useful. Not because I’m some visionary product genius, but because I made every possible mistake first.
The healthcare campaign taught me about brand voice consistency. The restaurant chain showed me why context layering matters.
The email sequence revealed the importance of sequential thinking. The software launch highlighted differentiation challenges. The fitness studio incident emphasized audience sensitivity. The financial blog series demonstrated architectural planning needs. The PR crisis showed why situation-specific prompts matter.
Each failure became a feature because I experienced firsthand how frustrating it is when AI doesn’t understand what you actually need.
Why This Approach Works
Jason isn’t built from theoretical best practices or academic research. It’s built from real-world failures and the solutions that actually fixed them.
When you use Jason, you’re not just getting a prompt generator. You’re getting the benefit of every mistake I made, every client conversation that went wrong, every late-night realization about why something didn’t work.
That’s why Jason asks different questions than other prompt tools. That’s why it considers contexts other tools miss. That’s why it produces prompts that actually understand your specific situation instead of generic templates that sort of work sometimes.
The Feature That Doesn’t Exist Yet
I’m still making mistakes, still learning from client projects, still discovering new ways prompting can go wrong.
Last week I realized Jason needs better support for evolving brand voices – companies that are intentionally shifting their positioning or expanding into new markets. That’s becoming the next feature because I watched a client struggle with exactly that challenge.
The tool keeps growing because the learning never stops. Every new client situation, every different industry, every unique challenge teaches me something about how to prompt better.
What’s the biggest prompting disaster you’ve experienced? Share your story below – it might inspire the next feature that helps everyone avoid that same mistake.