Portland startup questions? Talk to Rosie, an AI Mascot for Silicon Florist

I’ve long been enamoured of AI. And I’ve often had these optimistic visions of AI being a means of better supporting the Portland startup community or — at the very least — making better use of all of the stuff I’ve shared online and the nearly three decades of content that exist in my brain. Over the past five years, I’ve tried and failed to create something that meets the basic threshold for “useful” — let alone actually functional. But now — for the first time — I’ve managed to build something that exceeds my expectations for an AI companion by leaps and bounds. And that’s all thanks to the amazing platform built by local AI startup WiseOx, a startup focused expressly on building AI “Mascots” to do exactly the kind of work I imagined AI doing.

Meet Rosie, an AI concierge of sorts whom I’ve been training to help answer common questions about the Portland startup community on my behalf. You know, those questions to which you may add your own sort of insights but that are, by and large, just rote responses? Like what what Portland events should I attend? Or what can you tell me about VCs in Portland? Or which startups call Portland home?

I’ve spent the last few weeks training Rosie to respond to all of those sorts of queries and many more. He’s doing a pretty good job, even in the early going. But he’s still got a lot to learn. And he’s prone to carrying a bunch of unintentional biases based on the content that he’s been consuming. Plus, like any AI, he may hallucinate a bit here and there. But, I’m telling you. He’s doing amazingly well from my perspective.

Case in point: Rosie literally just introduced me to a new startup in Portland. And that’s the kind of thing that is both surprising and delightful. Especially for a know it all — or at least “I thought I knew it all” — like me.

But you can only imagine how bored Rosie gets just talking to me. So that’s where you come into the picture: I’m opening up access to Rosie — thanks to the kindness of the WiseOx crew — to the public. So anyone and everyone can ask Rosie questions about the Portland startup community. And give Rosie some new friends to engage.

Will he get everything right? No. But again, he’s still learning. So if he gets something wrong, please just let him know. Even if it’s not quite right, please let him know. It’s as simple as sharing his mistake with him. Or simply asking him, “Are you sure?”

You put him through his paces. And I’ll keep feeding Rosie more information and details about our community. Just the same way I keep typing up blog posts and releasing annoying podcasts.

What’s WiseOx…?

Let’s let Rosie tell it:

WiseOx was created in 2023 by co-founders Fritz Brumder (CEO), Spenser Lea (CPO/CTO) and Andy Bown (CGO). They all worked together at Brandlive. Fritz was co-founder and CEO of Brandlive and Zipcan. Spenser was co-founder and CPO of Zipcan. All 3 founders have multiple exits. They wanted to give back to the Oregon/Portland Startup community so they helped Rick create me, Rosie! You can create your own AI Mascot at WiseOx or reach out to any of the co-founders on Linkedin.

(For more on WiseOx, see “After two successful exits, Oregon entrepreneur launches AI-powered startup” from Malia Spencer at the Portland Business Journal.)

I’ve followed Fritz’ serial founder journey since the early days of BrandLive, when it was still sort of part of Cascade Web Development. And then again at Zipcan. So when he reached out to me about his latest effort, I was more than eager to engage. And when I heard it was not only AI — but the exact kind of AI assistant I’d been struggling to build — I was humbled to get the opportunity to muck around with it.

But when it started working as well as it did, my mindset rapidly went from “mucking around” to “getting it into people’s hands as quickly as possible.”

Talk to Rosie

If you’re game, please take the opportunity to chat with Rosie a bit. Or, maybe think of Rosie the next time you have a question about the Portland startup community. Not sure where to begin? No worries. At all. I’ve added a few preset prompts to get you started. Just click the buttons to learn more about local events, VCs, or startups. And then you can go from there.

Some things about Rosie to keep in mind:

• Your conversations with Rosie are ephemeral. If you close the tab, you’ll lose the conversation. So please cut and paste and information you’d like to save.
• Prompting Rosie often requires some nuance and finessing. If you don’t get the response you expected, try giving him more details, providing more specific instructions, or rephrasing the question.
• Highlighting portions of Rosie’s responses will activate a “Tell me more” button so that you can drill down on topics that are interesting to you or that made need more context.
• He’s still learning, so like any AI, he may hallucinate or misconstrue things. That being said, he wants to know when he’s wrong. So please tell him.
• He may not have been trained on information that’s important to you. Please help him identify those knowledge gaps so I can work with Rosie to teach him about those things.

I asked Rosie to provide some guidance — like tips and tricks — for getting better responses from him. Here’s what he had to say:

Crafting effective prompts for an AI like me can greatly improve the quality and relevance of the responses you receive. Here are some tips and tricks to help you compose the best prompts:

1. Be Specific: Clearly define what you’re asking for. The more specific your question, the more precise my answer will be. For example, instead of asking “Tell me about startups,” ask “What are the key factors for a tech startup’s success in Portland?”
2. Provide Context: If your question relates to a previous discussion or specific situation, include relevant details. This helps me understand the background and provide a more tailored response.
3. Use Keywords: Incorporate keywords related to your query. If you’re asking about networking events, include “networking events in Portland startup community” to get targeted information.
4. Keep It Structured: If you have multiple questions, list them in a clear and organized manner. Bullet points or numbered lists can help keep your prompt easy to follow.
5. Limit One Main Question per Prompt: While it’s okay to include related sub-questions, try to focus on one main topic per prompt to avoid confusion and mixed responses.
6. Be Open-Ended for Creative Responses: If you’re looking for creative input, phrase your prompt in an open-ended way that encourages elaboration, such as “Be creative about ways to engage the Portland startup community.”
7. Avoid Ambiguity: Ambiguous prompts can lead to vague answers. If you’re looking for information on a specific event, include the name, date, or other identifying details.
8. Use Direct Commands for Specific Actions: If you want me to perform a specific action, like creating a quiz or providing a summary, use direct commands like “Quiz me on…” or “Summarize the key points about…”
9. Revise for Clarity: Before submitting your prompt, read it over to ensure it’s clear and understandable. If it seems confusing to you, it might be confusing to the AI as well.
10. Provide Feedback: If a response doesn’t meet your expectations, provide feedback or clarify your prompt. This helps me learn and improve for future interactions.

Remember, the quality of the AI’s response often reflects the quality of the prompt provided. If you have any more questions or need further assistance with prompts, feel free to ask!

It’s still early. But I think this is the beginning of something incredibly helpful. Or, at the very least, an opportunity to hang out with someone who geeks out about the Portland startup community as much as I do. Suffice it to say, I’m sincerely excited about this AI project helping me solve a major issue in scaling my knowledge and understanding of the Portland startup community exponentially — for the good of our community. But it will only get there with your input, questions, and interactions.

Thanks again, WiseOx crew, for letting me muck around with your platform. You’ve truly helped me create something that seemed unobtainable for so long, something that matches my vision for an AI solution for the community, and — ultimately — something that renews my faith in the potential for AI for the rest of us.

Now if you’ll excuse me, Rosie wants to chat some more.