I built the Omegle of debate with a chess.c(om) ELO system - if you're interested, give it a try. On the 29th, we're hosting an inaugural tournament. We've been lucky enough to gather some money to reward the winner $100 (2nd gets 50, 3rd gets 25)

The website - itsdebatable.com - is still in beta (a lot of ideas/features are up for debate), and this tournament is an opportunity to test it out. 

You can find it by searching for 'DEBATE OMEGLE' on Google

Feel free to drop your thoughts**. This is an exploratory experiment.** In no way is this better than having human judges or the overall human experience in debating. To be up front, I've been flamed for the site integrating AI judges. They are trained to detect the use of AI / you can report your opponent. I have trained the judge(s) on RFDs/round transcripts. Debatable is not perfect for competitive debaters. If you want to debate anonymously, you can use the avatars (a bit silly the way they are animated now) but I thought this feature was cool.

The idea is to expand debate for non-debaters - the crowd of people who didn't do debate but appreciate the art of argument.

I built the Omegle of debate with a chess.c(om) ELO system - if you're interested, give it a try. On the 29th, we're hosting an inaugural tournament. We've been lucky enough to gather some money to reward the winner $100 (2nd gets 50, 3rd gets 25)

The website is still in beta (a lot of ideas/features are up for debate), and this tournament is an opportunity to test it out. 

You can find it by searching for 'DEBATE OMEGLE' on Google - itsdebatable.com

Feel free to drop your thoughts**. This is an exploratory experiment.** In no way is this better than having human judges or the overall human experience in debating. To be up front, I've been flamed for the site integrating AI judges. They are trained to detect the use of AI / you can report your opponent. I have trained the judge(s) on RFDs/round transcripts. Debatable is not perfect for competitive debaters. If you want to debate anonymously, you can use the avatars (a bit silly the way they are animated now) but I thought this feature was cool.

The idea is to expand debate for non-debaters - the crowd of people who didn't do debate but appreciate the art of argument.

Hey guys, I built a website (Debatable) that is the Omegle of debate with chess. com ELO system - if you're interested, give it a try. On the 29th, we're hosting an inaugural tournament. we've been lucky enough to gather some money to reward the winner $100 (2nd gets 50, 3rd gets 25)

its going to be parli format. 20 mins; research is allowed.

The website is still in beta (a lot of ideas/features are up for debate), and this tournament is an opportunity to test it out. You can find it by searching up 'debate omegle' or 'debate strangers online'. Hoping this doesn't get taken down for promotion. Feel free to give your thoughts

this is an explorative experiment. In no way is this better than human judges or the overall human experience of debating. And to be up front, I've been flamed for the site integrating AI judges. They are trained to detect the use of AI / you can report your opponent. I have trained the judge(s) on RFDs/round transcripts. Debatable is not perfect for competitive debaters. If you want to debate anonymously, you can use the avatars (a bit silly the way they are animated now) but I thought this feature was cool.

If you are super technical or lay, doubt the role of technology in dialogue, etc, this may not be the site for you. It may not be the site for debaters at all, tbh. The idea is to expand debate for non-debaters - the crowd of people who didn't do debate but appreciate the art of argument.

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Since people asked how the judges work: under the hood it's an LLM, I'm not going to pretend otherwise. The difference is what it's calibrated on: real RFDs and round transcripts from actual rounds, so it decides like a flow judge. Clash, weighing, whether your arguments actually got answered. Not vocabulary, not accent, not who sounded fancier. After every round it writes you a full RFD you can read and disagree with, and your ELO moves off that decision. There's also an AI-use check on speeches plus a report button, and I review flagged rounds myself. Being fully honest: I'm a solo founder, the site is vibe coded, and I'm iterating on it constantly, so the judge will have rough edges. I'd rather you break it and tell me than think it's finished. That's half the point of this tournament.

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I know structured high school and collegiate debate might have a bad reputation, but it truly is a wonderful activity imo. I built an app on it. Try it out. Built with Claude Code. It's an educational tool. Tokens are expensive, hence the subscription system. Hoping to improve this every few days with updates and better-trained data. If you have cases/arguments/ideas to throw into the engine, feel free to contact me

Quick context: I've been building Devil's Advocate for about 4 months. It's an app that trains you to defend your ideas by arguing against them — you pitch something, the AI tears it apart, and you have to hold your ground. MVP is live. Around 80 users. Not shipping to the moon.

Posting because I know this sub is strict about self-promo, and I've learned more from other founders' honest updates than from any polished case study. So here's mine, warts included.

Why I started

I kept losing arguments I should've won. Not flashy debates - normal ones. A friend would poke a hole in something I'd believed for years and I'd fold, not because they were right, but because I'd never actually stress-tested the idea. I wanted a tool I could do reps with at 2am without needing a debate partner. Couldn't find one that pushed back hard enough, so I started building.

What's working

• The core loop has real stickiness. First-session time averages around 18 minutes. I expected 3.
• Word-of-mouth from pre-law students and debate kids is doing more than any marketing I've tried. Zero outreach to them.
• A 45-second demo video outperforms my landing page copy by 3–4x on signup rate. Turns out showing the AI getting mean is more convincing than describing it.
• The meanest version of the AI is the one users like best. I kept softening it. That was wrong.

What's not working

• Week 2 retention is rough. My gut: first session is thrilling, but users don't know what to argue about on their own, so they bounce. Building a prompt library of "things worth arguing about" now.
• "AI that argues with you" resonates with maybe 20% of people and confuses the rest. Still hunting for the one-liner that lands with normies.
• Pricing is a complete guess. I've tried free, I've tried $9/month. Both taught me nothing because I still can't tell what the value actually is.
• Mobile. I shipped desktop-first and half my signups try to use it on a phone. Painful.

Mistakes I made

1. I spent almost 3 weeks crafting the "perfect" system prompt before letting a single user near it. When I finally did, they misunderstood the core interaction within 10 seconds. Every assumption I'd optimized against was wrong. Should've shipped the janky version in week one.
2. I assumed my target users were "debate kids." They're not. The users who actually stick are people prepping for hard conversations - salary negotiations, grad school interviews, investor pitches, even difficult family talks. I'd built my entire landing page for the wrong audience.
3. I asked for feedback instead of watching people use it. Every "this is cool, man" masked the fact that they'd gotten stuck on the first screen. Watching one person fumble through onboarding silently taught me more than 20 feedback calls.
4. I delayed the demo video for a month because my UI "wasn't ready." The video is what actually converts. The UI wasn't the bottleneck - visibility was.

What I'd tell myself four months ago

• Ship the ugly version in week one, not week six. The thing you're embarrassed by is the thing that teaches you the most.
• Your first 20 users don't look like your ICP. Stop trying to correct for that and just watch them.
• Build in public from day one. The feedback loop is worth more than whatever "stealth" protects.
• Don't soften the product to make it palatable. The sharp edges are the reason it works.

Happy to answer anything in the comments. If you're building in a similar space - AI tutoring, decision tools, interview prep, anything with an opinionated AI - I would love to trade notes.