Postmortem: An evening of wine and deals #angel #investing

This is a postmortem of an experimental event RVI held last night. You can find a detailed description of that event here.

What Went Right:

• For Entrepreneurs – Felt this was a dramatically better setting than the typical morning meetings of angel groups they had pitched at before. The cocktails and dinner conversations let entrepreneurs start building relationship momentum. The dinner presentations went well. The extensive face-time with investors after dinner, was much better than the 20 minutes of Q&A at a morning meeting they were used to (many guests stayed with the entrepreneurs for >1 hr). They also liked that the only people in their corner were people interested in their deal. The naysayers went somewhere else. The audience was almost entirely investors.
• For RVI Members – They liked the opportunity to meet the entrepreneurs in this format, enjoyed having a more social setting to chat with fellow RVI members, loved meeting so many new people, and had fun.
• For Non Members – Walked away with a very positive view of RVI and, I believe, are far more likely to co-invest with us or join the group.
• Attendance – Our goal was 20 attendees. We wanted many non-members attend. We had over 30 attendees and a large percentage were not RVI members.  We even had an angel from another angel group come, hopefully more of that will happen in time.

What Went Wrong:

• Too many presenters – The guests often liked more than one of the companies, but the format didn’t effectively let them spend time with more than one. The crowd for each group felt a little below critical-mass.
• Breakouts – Putting the breakouts in corners of a room not much bigger than the 5 tables we used for dinner meant that the room was loud, making it difficult for entrepreneurs to Q&A with the angels in their breakout group. The audience was understandably slow to migrate to “corners,” and in some cases snagged one member of a company’s team and started a little 2-on-1 parallel breakout session.
• Champion Pitches – After each entrepreneur gave their pitch their champion (generally lead investor) gave a 2-minute pitch on why the rest of us should invest. None of the champions had done this before and so they naturally didn’t have the experience to deliver their pitches optimally. That was my mistake as I should have provided them a template that they could (optionally!) rely on.
• Incomplete entrepreneur pitches – The entrepreneurs needed some guidance on what facts were most relevant to share.  One team didn’t even mention how much they were raising and under what terms.  I also should have suggested a standardized set of handouts.

What We Can Do Better:

• Limit of Two presenters
• Allow Q&A during dinner – With only two presenters, we can allow Q&A to happen over dinner. This will give the audience more data so they can decide which company to follow-up with.
• Separate room(s) for breakouts – We need to move at least one of the presenters into a separate room so that noise will be less of an issue. We also need to explore other tricks for ensuring entrepreneurs can be heard (possibly microphones?)
• Consider having mini-cash-bars – One entrepreneur suggested we set up two cash bars, but that they are right next to the breakout areas for the entrepreneurs. This will ensure that nearly all attendees will migrate towards one of the two presenters vs getting snagged in fun chit-chat right after dinner.
• Help Champions – I will provide deal champions a template (optional!) for their pitches and offer to do a “dry run” with them before the event.
• Help Entrepreneurs – Give entrepreneurs a set of recommendations (not mandates) on facts they should make sure to cover during their pitch and some best practices RE docs they should be sharing.

If I missed anything, please don’t hesitate to let me know in the comments or via email :).

-Paul