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Launch HN: TeamOut (YC W22) – AI agent for planning company retreats

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Re: Launch HN: TeamOut (YC W22) – AI agent for planning company retreats

#51
Vincent - nice work on this, there's clearly a good kernel of insight here, and I can tell you've been at this a couple years.

I completed a (rather large) contract to reverse-engineer, and eventually rebuild, a hotel chain's property management system from scratch from 2015-2018. We did it all: keycard integration, booking channel sync, credit cards, group bookings, yield management, front-desk GUI, supply management, taking rooms into/out of service, reservation migration from old system to new...you name it, we probably touched it. Dozens of small lessons about the lodging (and broader hospitality i.e. restaurants, country clubs, bars) business domain.

One thing is that hotel = brand (flag) + real estate + operations. You can remix those things in a lot of different ways, e.g. a single ownership group might have two properties on opposite sides of a street, one Hyatt the other Hilton, and they might look different but share staff, or procurement.

The industry's term for brand -- "flag" -- says a lot about how they view Hilton/Hyatt. They come and go, even if the staff running the property stays the same. The main reason hotels choose to flag vs. stay independent, is access to the chain's booking flow.

One of the more interesting consequences of this setup, is that small, independent hotels, are kind of a shit show in terms of technology. Chains generally require a lot of standardization of their member properties, including what software they run to manage the property. Many properties that don't affiliate with a chain don't have any property management system at all. It's basically 10-20 rooms run directly off the moral equivalent of an Excel sheet at the front desk. And why wouldn't it be--small boutique hotels often gross $1-2 million/year; there isn't budget for expensive enterprise software, or maybe more critically, the people who know how to deploy and operate it.

A significant value-add of Expedia and booking.com, especially with independent properties, is getting the supply (hotel) side of the market organized. Many of these hotels outsource their entire reservation tracking system to a single channel (e.g. booking.com) because trying to keep track of bookings across phone, direct web, Expedia, booking.com, and others, is just too hard without specialist software that requires more IT muscle to deploy than a single non-chain hotel can muster.

I mention this because I go to church every Sunday and was thinking about how much real estate churches have (event halls) that sit unused, and what a schlep it would be -- although good for everyone -- to expose the collective supply of the world's churches, HOAs, park districts, and other nonprofits, to the kind of events you're trying to do. It would indeed be a tremendous pain in the ass to get all the physical access (keys), contract terms, payment systems, availability, etc ironed out, but it's a massively underused class of real estate and many of these organizations could really use the cash.

Re: Launch HN: TeamOut (YC W22) – AI agent for planning company retreats

#52

How big is this market? Feels pretty narrow if it stays focused on company outings but are there plans for additional categories?

Good question. Globally, meetings, incentives, conferences, events, and group travel together represent a 500B+ market all in. Almost every mid-sized or large US company runs some form of in-person event each year, whether that is a retreat, sales kickoff, or team meetup. Since COVID, distributed teams have made these gatherings more important, not less. Corporate offsites are just our entry point because the pain is…

Whats the why now? AI makes the aggregation easier at first and then evenutally takes over the communication with the venue for contracts, etc. ?

Re: Launch HN: TeamOut (YC W22) – AI agent for planning company retreats

#53

I understand the pitch, and the extra value add of having some existing relationship with the hotels / etc. But the quality of the actual AI response is just worse than GPT 5.2. Which makes it feel like a tacked on thing and more of a gpt wrapper. I asked about a retreat with our US team that could also include one engineer in Pakistan that needs a visa. And the response was something to the effect of: "Assuming your…

This is interesting thank you for reporting that. I am goi t o investigate that use case deeper. The models at core are Gemini / ChatGPT / claude so you should get a similar level answer or better (because of our data) not worse. I think in the VISA, we may have to do a specific training and setup of the system prompt.

Just so I know, you asked the exact same thing in both ChatGPT and our product? no changes?

Maybe the algorithm was too pushy on venue selection and not enough focused on the understanding of your problem.

Re: Launch HN: TeamOut (YC W22) – AI agent for planning company retreats

#54

Well, I checked your chat cause I'm planning a company retreat to Athens for two teams - one from Poland, the other from Sweden. And the chatbot told me (after saying what a wonderful destination Athens is) that there are direct fligths from both cities to Athens which is simply not true...

Thank you for reporting that problem. I appreciate the help. The agent is supposed to checks real flight API so this is weird, let me investigate that further.

Re: Launch HN: TeamOut (YC W22) – AI agent for planning company retreats

#55

Vincent - nice work on this, there's clearly a good kernel of insight here, and I can tell you've been at this a couple years. I completed a (rather large) contract to reverse-engineer, and eventually rebuild, a hotel chain's property management system from scratch from 2015-2018. We did it all: keycard integration, booking channel sync, credit cards, group bookings, yield management, front-desk GUI, supply managemen…

Thanks a lot for this insight. Genuinely appreciate you taking the time to help me.

I 100% agree, the interface is the least interesting part. Anyone can build a chat UI. That’s not the moat.

What matters is the messy stuff in the backend. Vendors. Hotels. Quotes that change. Someone forgetting to update availability. Contracts. Deposits. Random edge cases. That coordination layer is the real product.

The UI is just the tip. The hard part is keeping state across dozens of moving pieces and async back-and-forth.

My belief is that AI finally makes some of this operational glue automatable. Not in a magical way. But in a very practical loop:

ask → get info → update plan → trigger action → wait → adjust → repeat

Planning is basically structured ping-pong. It’s not search. It’s evolving constraints over time. That’s why it feels agent-shaped.

What I am basically saying is : Event planning is really AI agent prone and very conversation prone, that is why this kind of interface will take over travel and event planning. It is like you have a personal travel agent sitting next to you and it showing you options.

Totally agree with you though. organizing fragmented supply is the hard, unsexy, painful work. That’s where the real value is built.

Re: Launch HN: TeamOut (YC W22) – AI agent for planning company retreats

#59

I understand the pitch, and the extra value add of having some existing relationship with the hotels / etc. But the quality of the actual AI response is just worse than GPT 5.2. Which makes it feel like a tacked on thing and more of a gpt wrapper. I asked about a retreat with our US team that could also include one engineer in Pakistan that needs a visa. And the response was something to the effect of: "Assuming your…

Similar for me. I asked for a retreat in Lima, Peru, and got one low star option in Lima and then places in Ohio, Mexico and Colombia... ChatGPT got it on first try

Re: Launch HN: TeamOut (YC W22) – AI agent for planning company retreats

#60

I asked it for locations in the Randstad (area in The Netherlands around Amsterdam) and I got: 1. Hoofddorp, Noord-Holland, Netherlands (actually ok location) 2. Marysville, Ohio, United States 3. Lisboa, Portugal 4. Nashville, Tennessee, United States 5. Kenmore, Washington, United States 6. Golden, Colorado, United States I would expect there to be some reviewer agent that ensures that all found locations are at le…

Thank you for reporting that. It is a real issue. We are actually pushing an update on that, we want to make the distinctions between Exact Matches (respecting destination criteria) and Non Exaft Matches , that. are suggestions. The below options were suggestions (because we have limited supply in Netherlands ) but it not clear at all for the user: 2. Marysville, Ohio, United States 3. Lisboa, Portugal 4. Nashville,…

This might be a situation where an old-school filter that I can control (same for price range) could add value rather than relying 100% on AI?

Did you push an update? I tried again and now got 6 locations in NL. For my initial comment I had prompted multiple times in different sessions but always got max 2 dutch locations.

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