Here are some of my thoughts on structure:
Workshops: I have really enjoyed some workshops, but it is quite hard to get right. I think guiding developers along the way is a great way to introduce new developers to an ecosystem, but it might not be the best format if most people in attendance are not new to the ecosystem. That being said, I always love a good demo.
Presentations: I would love to see presentations on the history of Interledger, possibly leading into the current strengths and weaknesses of the existing implementations, and briefly touch on future directions. This would also serve as a good placeholder replacement for the existing whitepaper.
I would also like to see presentations on scalability efforts from Strata Labs and some of the challenges they have faced. I have been messing around with Rafiki, and although it is well documented, it would be nice to see a presentation from the team behind it. Some other interesting areas include: security, liquidity exhaustion, wallet design, and possibly regulation.
Perhaps it wouldn’t make sense for an invite-only event, but if it is recorded, it would be nice to see some tangentially related projects present, such as Handshake, Summa One, Cosmos, and how other projects are thinking about value transfer and interoperability.
I know @danrobinson has been an active proponent of ILP, and spoke about it at Stanford Blockchain Conference, so I would love to hear more about some of the work he and others like him have been doing. For example, Starlight channels seem to be a great fit for ILP. How are blockchain companies thinking about ILP? How are existing payment solutions thinking about ILP? Are there any merchants interested in ILP? How do we make it easier to on-board existing developer ecosystems like Bitcoin and Ethereum?
Panel Discussions: Typically, I am not a big fan of panel discussions because they are largely unorganized and lead to only a few talking points and consensus or stalemate. I could see it being interesting in some cases, but for the most part, I do not think it is a good use of time.
Hackathon: I like hackathons, but I am not exactly sure about the format. When I have helped with hackathons in the past, I think it is really easy for people to get overwhelmed. Prizes for bounties and certain criteria are great for incentivizing people, but I am just not sure on how it would be best organized. Interledger is still maturing, but there are still a lot of services and plug-ins that need to be built out. A lot of submissions might prove to be starting points to critical infrastructure, but lack “creativity” because it is “just” a [much needed] wallet integration or what have you.
Side note: If anybody else is like me, I don’t like asking questions in front of a bunch of other people in some auditorium, and certainly not when there is a camera recording it. It’d be nice to have some kind of “ping” system (maybe just a sticky note with included interests like @emschwartz suggested, or just a lobby area with suggested times) to get some one-on-one discussion time with presenters.