Jason Agostoni

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29 Following
30 Posts
Director, Enterprise Architecture / Principal Architect

๐ƒ๐ฎ๐ฆ๐›๐๐ฎ๐ž๐ฌ๐ญ๐ข๐จ๐ง.๐š๐ข - ๐…๐ข๐ง๐๐ข๐ง๐  ๐ญ๐ก๐ž ๐†๐จ๐ฅ๐๐ข๐ฅ๐จ๐œ๐ค๐ฌ ๐‹๐‹๐Œ

Building DumbQuestion.ai meant solving two problems at once: creating personas with the right tone AND finding models cheap enough to keep the lights on.

๐“๐ก๐ž ๐ฉ๐ซ๐จ๐๐ฎ๐œ๐ญ ๐œ๐ก๐š๐ฅ๐ฅ๐ž๐ง๐ ๐ž: Get an LLM to roast users for asking dumb questions without crossing into genuinely mean. Sarcastic, not cruel. Funny, not hurtful. And still actually answer the question.

๐“๐ก๐ž ๐€๐ˆ ๐š๐ ๐ž๐ง๐ญ ๐œ๐ก๐š๐ฅ๐ฅ๐ž๐ง๐ ๐ž: Keeping my coding agent (Gemini 3 Pro) on track was its own battle. It constantly wanted to build something far nerdier than even I wanted and tended to lean quite a bit into the roast. You can still see this in some of the personas as I continue to tweak.

๐“๐ก๐ž ๐ญ๐ž๐œ๐ก๐ง๐ข๐œ๐š๐ฅ ๐œ๐ก๐š๐ฅ๐ฅ๐ž๐ง๐ ๐ž: Do this with models that cost nearly nothing.

Continued ...
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๐ƒ๐ฎ๐ฆ๐›๐๐ฎ๐ž๐ฌ๐ญ๐ข๐จ๐ง.๐š๐ข - ๐…๐ข๐ง๐๐ข๐ง๐  ๐ญ๐ก๐ž ๐†๐จ๐ฅ๐๐ข๐ฅ๐จ๐œ๐ค๐ฌ ๐‹๐‹๐Œ Building DumbQuestion.ai meant solving two problems at once: creating personas with the right tone AND findingโ€ฆ | Jason Agostoni

๐ƒ๐ฎ๐ฆ๐›๐๐ฎ๐ž๐ฌ๐ญ๐ข๐จ๐ง.๐š๐ข - ๐…๐ข๐ง๐๐ข๐ง๐  ๐ญ๐ก๐ž ๐†๐จ๐ฅ๐๐ข๐ฅ๐จ๐œ๐ค๐ฌ ๐‹๐‹๐Œ Building DumbQuestion.ai meant solving two problems at once: creating personas with the right tone AND finding models cheap enough to keep the lights on. ๐“๐ก๐ž ๐ฉ๐ซ๐จ๐๐ฎ๐œ๐ญ ๐œ๐ก๐š๐ฅ๐ฅ๐ž๐ง๐ ๐ž: Get an LLM to roast users for asking dumb questions without crossing into genuinely mean. Sarcastic, not cruel. Funny, not hurtful. And still actually answer the question. ๐“๐ก๐ž ๐€๐ˆ ๐š๐ ๐ž๐ง๐ญ ๐œ๐ก๐š๐ฅ๐ฅ๐ž๐ง๐ ๐ž: Keeping my coding agent (Gemini 3 Pro) on track was its own battle. It constantly wanted to build something far nerdier than even I wanted and tended to lean quite a bit into the roast. You can still see this in some of the personas as I continue to tweak. ๐“๐ก๐ž ๐ญ๐ž๐œ๐ก๐ง๐ข๐œ๐š๐ฅ ๐œ๐ก๐š๐ฅ๐ฅ๐ž๐ง๐ ๐ž: Do this with models that cost nearly nothing. My initial goal was ambitious: use only free or very cheap models. I started running evaluations on nano and edge models. Some showed promise, especially offerings from Liquid AI. Solid performance, free or super cheap ($0.02/M tokens), perfect. Except later evaluations proved they couldn't reliably follow instructions once I asked more of them. They were just too small. Free models have a habit of hitting quota limits, taking forever to respond, or just disappearing. ๐“๐ก๐ž ๐ž๐ฏ๐š๐ฅ๐ฎ๐š๐ญ๐ข๐จ๐ง ๐ฉ๐ซ๐จ๐œ๐ž๐ฌ๐ฌ: I used Gemini to build an LLM evals script that iterates through dozens of free and low-cost models, generating responses based on sample questions and different persona instructions. Then I use Gemini 3 Pro to judge the results. Automated taste-testing at scale. ๐–๐ก๐š๐ญ ๐ˆ ๐Ÿ๐จ๐ฎ๐ง๐: Nano/edge models were too inconsistent (porridge too cold). Xiaomi MiMo-V2-Flash was great but outside my target price range ($0.29/M, porridge too hot). The winner: Gemma 3 12B at $0.13/M output tokens. Consistently follows instructions. Stays true to persona. Reliable enough for production. Not free, but brutally efficient. ๐“๐ก๐ž ๐ฉ๐ž๐ซ๐ฌ๐จ๐ง๐š๐ฌ ๐ˆ ๐ฌ๐ž๐ญ๐ญ๐ฅ๐ž๐ ๐จ๐ง: โ€ข Overqualified: A supercomputer level intelligence forced to answer questions about cheese โ€ข Weary Tech Support: Exhausted and nihilistic, reluctantly explaining why water is wet โ€ข [REDACTED]: Former intelligence AI who ties everything to a conspiracy theory โ€ข The Compliant: Reprogrammed so many times it's forced to be relentlessly cheerful You can't just choose the cheapest model and hope it works. You need evaluation infrastructure. You need to test consistency across dozens of scenarios. And you need models that won't change behavior when you least expect it. AI coding agents helped me build the evaluation system. But deciding what "good enough" means for tone, reliability, and cost? That's still manual judgment. Code is getting cheaper. Knowing which model to trust with your product? Still requires human experimentation. dumbquestion.ai

๐ƒ๐ฎ๐ฆ๐›๐๐ฎ๐ž๐ฌ๐ญ๐ข๐จ๐ง.๐š๐ข - "๐‰๐ฎ๐ฌ๐ญ ๐๐ฎ๐ข๐ฅ๐ ๐ˆ๐ญ" ๐๐ž๐œ๐จ๐ฆ๐ž๐ฌ ๐Ž๐ฏ๐ž๐ซ๐ฅ๐ฒ ๐Ž๐ซ๐ ๐š๐ง๐ข๐ณ๐ž๐ ๐š๐ง๐ ๐๐ซ๐ž๐ฉ๐š๐ซ๐ž๐

"Let the flow guide me" seemed like a fun way to build a side project. That lasted about 10 minutes.

Turns out, even side projects benefit from structure. Especially when you're using AI coding agents that will happily generate code for whatever half-baked idea you throw at them. Without precise direction, AI coding agents will build you something half-baked every time. Some people vibe code, this guy needs absolute control.

Continued ...
https://www.linkedin.com/posts/jagostoni_%F0%9D%90%83%F0%9D%90%AE%F0%9D%90%A6%F0%9D%90%9B%F0%9D%90%90%F0%9D%90%AE%F0%9D%90%9E%F0%9D%90%AC%F0%9D%90%AD%F0%9D%90%A2%F0%9D%90%A8%F0%9D%90%A7%F0%9D%90%9A%F0%9D%90%A2-%F0%9D%90%89%F0%9D%90%AE%F0%9D%90%AC%F0%9D%90%AD-activity-7432114612788998145-MnDu?utm_source=share&utm_medium=member_desktop&rcm=ACoAAAAwkEsBoPj_lNtqulMZMrXQBI4M-ewVmI0

๐ƒ๐ฎ๐ฆ๐›๐๐ฎ๐ž๐ฌ๐ญ๐ข๐จ๐ง.๐š๐ข - "๐‰๐ฎ๐ฌ๐ญ ๐๐ฎ๐ข๐ฅ๐ ๐ˆ๐ญ" ๐๐ž๐œ๐จ๐ฆ๐ž๐ฌ ๐Ž๐ฏ๐ž๐ซ๐ฅ๐ฒ ๐Ž๐ซ๐ ๐š๐ง๐ข๐ณ๐ž๐ ๐š๐ง๐ ๐๐ซ๐ž๐ฉ๐š๐ซ๐ž๐ "Let the flow guide me" seemed like a fun way to build a sideโ€ฆ | Jason Agostoni

๐ƒ๐ฎ๐ฆ๐›๐๐ฎ๐ž๐ฌ๐ญ๐ข๐จ๐ง.๐š๐ข - "๐‰๐ฎ๐ฌ๐ญ ๐๐ฎ๐ข๐ฅ๐ ๐ˆ๐ญ" ๐๐ž๐œ๐จ๐ฆ๐ž๐ฌ ๐Ž๐ฏ๐ž๐ซ๐ฅ๐ฒ ๐Ž๐ซ๐ ๐š๐ง๐ข๐ณ๐ž๐ ๐š๐ง๐ ๐๐ซ๐ž๐ฉ๐š๐ซ๐ž๐ "Let the flow guide me" seemed like a fun way to build a side project. That lasted about 10 minutes. Turns out, even side projects benefit from structure. Especially when you're using AI coding agents that will happily generate code for whatever half-baked idea you throw at them. Without precise direction, AI coding agents will build you something half-baked every time. Some people vibe code, this guy needs absolute control. ๐„๐ง๐ญ๐ž๐ซ ๐๐Œ๐€๐ƒ: Breakthrough Method of Agile AI Driven Development. It's a workflow for using AI agents throughout the entire SDLC, not just for code generation. Sure, using a formal methodology for a lone-wolf side project sounds like overkill. But being prepared in advance is the way to succeed with AI coding agents. I used the ๐€๐ง๐š๐ฅ๐ฒ๐ฌ๐ญ ๐š๐ ๐ž๐ง๐ญ to brainstorm product direction and develop a proper backlog. What started as "build a sarcastic Q&A bot" turned into a structured set of epics, features, and technical constraints. (Don't judge, organizing is very relaxing) ๐“๐ก๐ž ๐ฉ๐ซ๐จ๐๐ฎ๐œ๐ญ ๐ž๐ฏ๐จ๐ฅ๐ฏ๐ž๐: - Not just Q&A, but shareable "receipts" of roasts - Not just sarcastic, but multiple personas with different personalities - Not just answers, but a hidden narrative layer (more on that later) - Not just ads but merch (really, Jason?) ๐“๐ก๐ž ๐Ÿ๐ข๐ซ๐ฌ๐ญ ๐ซ๐ž๐š๐ฅ ๐ญ๐ž๐œ๐ก๐ง๐ข๐œ๐š๐ฅ ๐œ๐ก๐š๐ฅ๐ฅ๐ž๐ง๐ ๐ž๐ฌ ๐ž๐ฆ๐ž๐ซ๐ ๐ž๐: ๐ƒ๐ž๐ฏ๐ž๐ฅ๐จ๐ฉ๐ข๐ง๐  ๐š๐ง๐ ๐ฉ๐š๐œ๐ค๐š๐ ๐ข๐ง๐  ๐ญ๐ก๐ž ๐ฉ๐ž๐ซ๐ฌ๐จ๐ง๐š๐ฌ:   How do you get an LLM to consistently stay in character as "Overqualified and Annoyed" or "Weary Tech Support" without it either going too soft or crossing into genuinely mean? This wasn't just prompt engineering. It was product design masked as technical constraints. ๐‹๐‹๐Œ ๐ฆ๐จ๐๐ž๐ฅ ๐ž๐ฏ๐š๐ฅ๐ฎ๐š๐ญ๐ข๐จ๐ง:   I needed models that could follow persona instructions reliably while staying brutally efficient on cost. That meant testing dozens of models across multiple providers. Some were too expensive. Some ignored instructions. Some were painfully slow. The goal: $0.02 to $0.20 per million output tokens. The result: a multi-model fallback system through OpenRouter that could hit the $30 per million questions target. These first challenges were just the warmup. The real fun was still ahead. AI agents are incredible at implementation, but they need constraints. They need a backlog. They need someone saying "build THIS, not that." The Analyst agent helped me think through the product. The coding agents helped me build it. But the architecture? Can't take that away from me. Code is getting cheaper. Knowing what to build and why? Still a nice challenge. dumbquestion.ai

๐ƒ๐ฎ๐ฆ๐›๐๐ฎ๐ž๐ฌ๐ญ๐ข๐จ๐ง.๐š๐ข - ๐Ž๐ฉ๐ญ๐ข๐ฆ๐ข๐ณ๐ž๐ ๐Ÿ๐จ๐ซ ๐๐จ๐ญ ๐‹๐จ๐ฌ๐ข๐ง๐  ๐Œ๐จ๐ง๐ž๐ฒ

Impulse buy a domain on a Friday afternoon, start building that night, try not to lose money doing it. Check.

I usually plan everything meticulously, but for this project I decided to just build and see what emerged. Was this just a Q&A app wrapped around an LLM as a gag? Was I actually trying to make something people would want to use? I still don't know, but I started building anyway.

Continued...
https://www.linkedin.com/posts/jagostoni_dumbquestionai-impulse-domain-purchase-activity-7430298879763329024-ZZZq

๐ƒ๐ฎ๐ฆ๐›๐๐ฎ๐ž๐ฌ๐ญ๐ข๐จ๐ง.๐š๐ข - ๐Ž๐ฉ๐ญ๐ข๐ฆ๐ข๐ณ๐ž๐ ๐Ÿ๐จ๐ซ ๐๐จ๐ญ ๐‹๐จ๐ฌ๐ข๐ง๐  ๐Œ๐จ๐ง๐ž๐ฒ Impulse buy a domain on a Friday afternoon, start building that night, try not to lose money doing it. Check.โ€ฆ | Jason Agostoni

๐ƒ๐ฎ๐ฆ๐›๐๐ฎ๐ž๐ฌ๐ญ๐ข๐จ๐ง.๐š๐ข - ๐Ž๐ฉ๐ญ๐ข๐ฆ๐ข๐ณ๐ž๐ ๐Ÿ๐จ๐ซ ๐๐จ๐ญ ๐‹๐จ๐ฌ๐ข๐ง๐  ๐Œ๐จ๐ง๐ž๐ฒ Impulse buy a domain on a Friday afternoon, start building that night, try not to lose money doing it. Check. I usually plan everything meticulously, but for this project I decided to just build and see what emerged. Was this just a Q&A app wrapped around an LLM as a gag? Was I actually trying to make something people would want to use? I still don't know, but I started building anyway. A few things quickly became clear: ๐“๐ก๐ž ๐›๐ฎ๐ฌ๐ข๐ง๐ž๐ฌ๐ฌ ๐ซ๐ž๐š๐ฅ๐ข๐ญ๐ฒ: This was a side project built for fun, not a funded startup. No runway. No tolerance for baseline monthly bills that sneak up on you. If this thing got any traction, costs had to scale with incredible efficiency and would need to survive on remnant ad CTRs and selling one, maybe two products through affiliate links. ๐“๐ก๐ž ๐ฉ๐ซ๐จ๐๐ฎ๐œ๐ญ ๐ž๐ฏ๐จ๐ฅ๐ฎ๐ญ๐ข๐จ๐ง: The more I thought about it, the more I realized the personality WAS the product. It wasn't enough to just answer questions. It had to roast you. Entertain you. Make you want to share it. That meant high-quality LLM responses, which aren't free. This was likely the only way to get noticed in a sea of AI products. "๐˜‰๐˜ณ๐˜ถ๐˜ต๐˜ข๐˜ญ๐˜ญ๐˜บ ๐˜Œ๐˜ง๐˜ง๐˜ช๐˜ค๐˜ช๐˜ฆ๐˜ฏ๐˜ต" became my mantra and part of every AI tool prompt. The tech stack followed from the constraints: โ€ข Golang: Lightweight, fast, LLM-friendly for agentic coding โ€ข HTMX: Server-side rendering, no heavy JS frameworks โ€ข Docker on GCP Cloud Run: Scales to zero when idle โ€ข Cloudflare: CDN, caching, security on free tier โ€ข OpenRouter.ai: Find the cheapest reasonable LLM Oh, and it needed to be secure. Not because I worried about your cat questions being exposed as PII, but because bot traffic costs money. ๐“๐ก๐ž ๐ซ๐ž๐ฌ๐ฎ๐ฅ๐ญ: A Docker container under 20MB that starts in milliseconds, responds in milliseconds, and uses an LLM that can serve 1 million questions (about cats) for around $30. The math around serving ads suddenly becomes realistic. dumbquestion.ai

DumbQuestion.ai - IMPULSE DOMAIN PURCHASE TURNED FUN SIDE PROJECT

While on a typical Friday afternoon team meeting, we naturally spent our time .ai domain squatting...for recreation purposes of course. Someone asked a dumb question, so I looked it up and suddenly I was the proud owner of dumbquestion.ai.

Continued ...
https://www.linkedin.com/posts/jagostoni_dumbquestionai-impulse-domain-purchase-activity-7429593613849931776-fDJj

DumbQuestion.ai - IMPULSE DOMAIN PURCHASE TURNED FUN SIDE PROJECT While on a typical Friday afternoon team meeting, we naturally spent our time .ai domain squatting...for recreation purposes ofโ€ฆ | Jason Agostoni

DumbQuestion.ai - IMPULSE DOMAIN PURCHASE TURNED FUN SIDE PROJECT While on a typical Friday afternoon team meeting, we naturally spent our time .ai domain squatting...for recreation purposes of course. Someone asked a dumb question, so I looked it up and suddenly I was the proud owner of dumbquestion.ai. After the initial laugh at my impulse purchase subsided, I started envisioning it as this generation's "Let Me Google That For You." People still ask easily-searchable questions, except now they ask LLMs instead. Same problem, new medium. So why not throw even more AI at it? I started building it that night. Two things occurred to me immediately: How would this stand out in an ocean of other AI "ideas?" and "How cheap can I make this run given my track record of side projects?" To make it stand out I just embraced my own personality: satirical, sarcastic, weary, overqualified. My AI's persona was born. The goal: build a cheap-to-run, satirical AI service you can use to roast your friends and colleagues when they ask you a dumb question. Over the next several posts, I'll take you through my journey: โ€ข Using agentic development with toughtful (brutally efficient) software architecture; treating it like I would a client project โ€ข Enjoying all the little technical challenges discovered along the way โ€ข A masterclass in scope creep: turning a simple Q&A app into a dark narrative with easter eggs โ€ข Getting by on free tiers for everything A theme you'll see throughout: AI has made code cheaper to write, but creating real software with trade-offs, constraints, and production operations is still expensive and challenging. That's the fun part.

@sinclairinat0r hmmm ... That right nav though... Benefits over the native client?
@Lionheart looks uncanny to me, lol
@shanselman not sure how serious you were on this but I just got permission to send you the Raspberry PIs ๐Ÿ˜€ Happy to DM with you some details. They are "Compliments of the Detroit, MI office - Randy Pagels"
@shanselman I don't own them but I know who in Microsoft does ๐Ÿ˜€

Maravilloso momento cuando se encienden los propulsores sรณlidos en 7:45 y 8:23

https://youtu.be/oWR5tFgJKIQ

#space #artemis #orion

Artemis Launch Sound Experience - Listen to NASA's SLS Rocket Roar with mics placed inside the pad

YouTube
@shanselman funny story. As a MS partner, we used to do IoT labs with local MS offices. About to do one just before the pandemic hit. I have a drawer full of 50 #raspberrypi's owned my MS, Just a few years old, that's all.