Tips on Demo Day and Afterwards for YCombinator Startups

These last few weeks I’ve been part of the Ycombinator Mentors program where we get a few of the YC startups to hang with and help them, as Paul Graham puts it, “convince us to invest in them.” It’s been a great experience going through product and business issues, and helping them shape something meaningful and hopefully world dominating with their initial ideas.
I just completed this email to send out to my mentees (is that a word?) as I realized that, after attending several YC Demo Days, that I have seen a remarkable number of the teams not take advantage of the opportunity to really engage with the audience of investors, reporters, and corporations. As both a reminder and a call to action (mostly to make introverted engineers break out of their shell!), I listed some items that might help. I think it also helps to know how we feel on our end, as we sit through 20+ fast paced presentations and then enter a whirlwind of conversations after.
Here’s the email:
I thought I would send some thoughts on handling Demo Day and its aftermath (if anything to be a good YC mentor..!) as I’ve seen some YC teams really handle it poorly. This is not about the presentation as I’m sure that PG and others are hammering you guys on getting that good. Rather, this about what happens during Demo Day after the presentations and how to manage the crowd, and even afterwards.
BEFOREHAND:
1. If you don’t have business cards, get some made now! Go to FedEx/Kinko’s and give them an illustrator file. They can make business cards overnight.
2. PG undoubtedly has an attendee list; can you get that from him? Review it beforehand and try to prioritize those people to meet. Keep it in your pocket and check off people that you meet and make quick notes on interest, experience, follow ups, next steps, etc.
If you can, prepare beforehand a little about what you may talk to certain people about. This can be as simple as knowing a few of the recent investments an investor has made, or how you can help Google build one of their products better. Or perhaps you’d like to get in touch with someone’s portfolio company. This can be as simple as a conversation starter to break the ice, or as big as trying to do a deal with Google to integrate your technology.
3. Think about your own status. Are you raising money now? Soon? Or not? Have you raised money already? Looking for business partnerships? Want to sell out or get acquired right now?
Make sure you decide as much of this beforehand as it will undoubtedly affect your conversations. You will inevitably be asked, “are you raising money now?” and you should have some sense for yes or no, and if yes, for how much. You want to be confident in your progress and in your answers, not wishy washy. The worst thing you could say is, “well, I don’t know…maybe…we’re not really sure yet…hem haw…” But also, don’t lie or make things up. This is more about anticipating what questions will be asked of you post-presentations and just taking a bit of time to prepare your response.
4. Try to get a good night’s sleep the night before. Try to arrive at the top of your game, not sleep deprived and/or over-caffeinated.
AT DEMO DAY, AFTER THE PRESENTATIONS:
1. The crowd as you can imagine is filled with reporters, corporate representatives (typically from venture arms), angel investors, and venture capitalists. It is really like speed dating; you should get out there and meet as many people as possible, getting their contact info and gauging their interest in you.
It will be, and expect it to be, overwhelming. It is definitely overwhelming to us. We’ll have been overloaded by the quick machine gun set of presentations and trying to absorb it all, and then we’re thrown into fast smoozing with those startups that somehow have grabbed our attention. We’ll be scribbling fast notes on our Demo Day sheets and then we’re going to try to go back and figure out who we want to meet first before we have to leave.
2. Don’t be a wallflower! I’ve seen some teams hang on the sidelines and not mingle. This is bad! This is a chance for you to meet and try to woo some investors to be interested in you! If you don’t meet them now, you may never get a chance to interact face to face with them again. If you have more than one founder, split up and meet more people! There are 20+ teams this time; everyone is going to be competing for attention of the audience. Get in there and meet!
3. As you get business cards, make notes on the back of their cards as well. Stick them in a safe place and don’t lose them! I’ve met many people who simply lost my business card and somehow found me later. Bad!
4. Regarding reporters: you probably have never gone through media training but it’s not hard. You should just prepare some great sound bites for reporters to hang onto and include in their writeups. These are simple sentences that sound great, and of course promote your product/company/service.
5. Be lively, upbeat, friendly, excited about what you’re working on, and excited about future prospects. I think that engineering types tend to be very introverted. Unfortunately, this doesn’t serve you well here! So go out and be an extrovert. Force yourself to go out and meet everyone and to be Mr. Fun and Cool with the best product in the world to talk about. People react to and engage with people they like; boring, uninteresting people get left behind. It sucks but it’s true.
So psyche yourself up for some power smoozing and have a positive attitude about it. This won’t be the last time you’ll be power smoozing for your business!
6. Gauge whether a conversation is going nowhere or somewhere. Lack of interest, conversation seems to slow down or feel strained, etc. all are signs that you should disengage gracefully and move on to the next person. Shake their hand, make eye contact and say nice meeting you and move on!
Definitely stay with someone a bit longer at least if they are interested in you and what you’re doing. But don’t extend the conversation too long as you only have about 2-3 hours after the presentations end to talk to all the people you want to talk to. People start trickling away after an hour of smoozing; remember many people have other meetings and places to go. It’s very rare that people stay all the way to the end! Again, disengage with set action items to follow up, and with contact info exchanged.
AFTERMATH:
1. Write a follow up email to everyone you met! Say hi, it was nice meeting up and you’d love to get together to talk further. Remind them with what you and he discussed.
Keep in the mindset of the folks you meet – remember that we’re going to be totally talked out and our brains won’t be able to remember all the conversations and people we’ve met. We’ll have gone through so many people in so little time; it’s overwhelming and you will want to rise above the noise by following up.
2. Keep an email list of everyone you met for updates. This is to keep reminding everyone of the progress you’re making. Don’t spam this list; just put out an update once a month or every two months. This is also to keep in everyone’s mindshare. Even if someone doesn’t invest in you today, they may invest in you tomorrow when you’re bigger. Or they may contact you for a deal, or to acquire you. They won’t do any of that if they forget about you.
3. Pursue those follow up meetings! Get feedback on why someone isn’t investing and improve yourself, your product, and your pitch. It’s amazing how I’ve had to contact people afterwards and chase them down. But that also signals poorly; aggressive fund raisers who don’t give up are those who succeed in raising the money they need. Passive entrepreneurs only increase the risk that they will fail, because they aren’t aggressive.
A lot of this is basic smoozing, or “How to Work a Room” 101. I just wanted to bring it up because while some of this is basic, it’s been obvious to me from attending past Demo Days that many YCers either haven’t learned it, or maybe forgot about it in the heat of prepping for Demo Day.
Looking forward to Demo Day next week!

  • Definitely good pointers. It’s all about the hustling. Yes. Mentees is a word.