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The Medley of Misfits – Reflections from Day 2 at the AI Engineer World’s Fair

By Tela Mathias

I love being at events like this, I feel like I have met “my people”. We are this weird, eclectic, smart, funny, and super enthusiastic bunch of nerds. Just really nerdy. And I love it. We are just a medley of misfits. So many great things at Day 2 – but the two major highlights were at the beginning and the end. Simon Willison is a hilariously competent and compelling speaker, and definitely part of our medley of misfits. And closing the day with Greg Brockman was an absolute inspiration. The theme of yesterday was the “the power of optimism”, but maybe that’s just because I’m an optimistic person.

Spark to System: Building the Open Agentic Web with Asha Sharma

Wish I new his name, but the demo guy at Microsoft was ON POINT. He showed what you can do with Github Copilot and I have to say – wow. The intersection of spaces, Jira, agents, and agent task assignment really told a good story. Imagine that an agent is just another team member, logged in and working like you or me. Imagine that you could assign a task to an agent, readme file generation was the example they used, and then the agent does the work and updates the work item. Now imagine that you need a team member to do a machine learning model, yeah you can assign that to a coworker agent too.

This definitely made we want to make sure that we are making maximum use of the full set of Microsoft capabilities at the team level. It was not, however, enough to make me move from AWS Bedrock to Azure AI Foundary. Maybe I’ll regret this decision at some point but I’m sticking for now. You’re welcome Amazon Web Services.

State of Startups and AI 2025 with Sarah Guo

Talk about overcoming adversity, Sarah Guo is a presentation boss. None of the technology was working, AV was a hot mess, and honestly, they barely figured it out. She used the time with mastery, and I was riveted by her take.

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Sarah is the founder of Conviction, an AI venture capital company. She was speaking on the state of startups in 2025 and providing practical advice. One of the things they are very interested in and encouraged is to think about (you know how VC loves their analogies) is: “Cursor for [_X_]”. In our case it would be “Cursor for Compliance” although that’s not where we are yet, but we will be.

One of the reasons Cursor has been so successful is because it was built by engineers for engineers. And engineers know engineers. She out the cherry on top of what we have been hearing for the past six months, content is king. Knowing your customer, knowing your domain space, really building what you know for and market you know – that continues to be the moat.

  1. Domain is king. Needs no further explanation.
  2. Show up informed. Have a product that has an opinion. Have a product that reflects what we know, what our customers know.
  3. Requiring a prompt is a bug, not a feature. Loved this one, and it validated what we have done. The idea that a user has to prompt the system to do what they need is a bug – the system should just do what you need. And present thoughtful outputs at the appropriate times to the right people, in an excellent ux. I mean it’s easy really.
  4. The moat is execution. Just out execute everybody. Move fast. Continue to move fast. Get to market. (I’m here for it, sister!)
  5. Copilots are still underrated and viable solutions. This was kind of a relief, honestly. I straddle federal, commercial mortgage, and Silicon Valley. I see so many different stages on the adoption curve, and different stages of technology delivery maturity. It is really hard to go from the AI future to the mortgage now. I struggle with what we can/should actually do with all this light speed tech, and this was a helpful sentiment.
  6. BE IRONMAN. Think of your solution as a supercharged companion. Some things Tony Stark has to do, some things the suit does autonomously. Over time the suit does more and more and Tony does less, but also more different. Be Ironman.
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I loved the idea that building the ironman suit is the bath of least frustration. Start with what you know, you can always make it better. Sarah Gua is a BOSS. Loved her.

2025 in LLMs so Far with Simon Willison

I had, sadly, never heard of Simon Willison. He was falling out of your chair funny. I love his personal eval, “product an SVG of a pelican riding a bike”. This reminded me of Ethan Mollick and his “otter taking a plane ride” eval. So Simon was there to talk about the past year in LLMs, but there was too much so he skinnied his scope down to the past six months.

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The reason he uses the pelican riding the bike is because (a) he’s tired of the other benchmarks and has lost trust and (b) it’s a great test because it requires technical prowess in producing the SVG, the pelican has very difficult anatomical structures that are incompatible with riding a bicycle, and the bicycle seems simple but is actually a challenge for humans to illustrate due to its interesting geometry.

Some of the key points made clear in the past six months:

  1. Local is good now.
  2. Prices of good models have absolutely plummeted, which is a good thing for us. We will continue to see a crushing pace on the releases of mew models and model upgrades. The basic message here is that there was so much improvement that you really do have to pay attention.
  3. Humorous discussion of the infamous OpenAI sycophantism bug. Evidently the source prompts that were used to fix it leaked so you can see the actual from and to documentation, fascinating. That one was hilarious.
  4. Somber noting of the Grok White Genocide horror show. Enough said there. I just can’t with Elon.
  5. Evidently Claude 4 will “rat you out to the feds” for certain prompts and content generation. I really had no idea, but I guess it makes sense. I’m not sure how I feel about this.
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Impact AI on Consulting

This one was near and dear to my consulting roots. I had never heard of the company, but I really resonated with what they were talking about. They talk about the staffing models – traditional pyramid v. inverted pyramid (relying on junior staff to do most of the work v. relying on senior staff to do most of the work). And their hypothesis on the future for professional services is the inverted pyramid in the center, with traditional pyramids of agents at each side. This makes a lot of sense to me. Not sure I would have illustrated it this way but intuitively, it’s the right move.

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I was surprised that they did not discuss voice agents more specifically, I think the opportunity there is massive. Imagine if you would interview and entire company in, like, two hours. Yeah, voice agents. I’m here for it.

Windsurf Everywhere, Doing Everything, All at Once

I’m so glad that we pivoted away from automating software development because man, Windsurf has pretty much crushed that. This one was personal, when we started this AI journey in December of 2023, I was hell bent on “push button, get software”. Many of our early research meetings were about this idea of automating software development. As we learned more, and really listened to our industry feedback, we realized we needed to be a lot more specific and much closer to the market – hence mortgage compliance change management, of which software development is a key part.

And that was a really good pivot. Windsurf is going to absolutely crush this space. Their vision is ridiculously bold – to be everywhere, doing everything, all at once. And I believe them when they talk about how they intend to do it. I think they will crush everyone, they certainly would have crushed my original product concept. Phew – dodged a bullet there.

Reflections from Greg Brockman, President OpenAI

Greg really gave Jenson a run for his money on being my idol and personal hero (#jensenisstillthegoat). I’m slightly embarrassed to admit I did not know him before this closing keynote. Well, I certainly won’t forget him. He was absolutely inspiring. This will be the subject of a separate article. Too short on time to do it justice.

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