by Andrew Bridge.

As a forty-something professional,  I’ve been on my share of first dates. As an investor in early-stage consumer businesses, I’ve sat through more investor meetings than I can remember.  There are a surprising number of parallels between the two-in fact, the qualities of a great first date are very similar to those in an investor meeting.  

With that in mind, here are the top five reasons to treat an investor meeting like a first date:

  1. Cyber-stalking is encouraged.

Chances are low you’d accept a date without doing a little due-diligence online. The same applies to investor meetings. You can bet we’ve done a lot of homework on your business, your industry, and you personally. You should do the same. Make it clear to investors that you’ve done your research — you should know who we are, why we’d make a good partner, what our strengths and weaknesses are and be ready to ask questions to fill in the gaps. A lot of the typical first-date material can be done before-hand, leaving us free to dive into the details instead.

  1. First Impressions Matter.

Workplace cultures are shifting to become more casual. We’re into it – we like jeans as much as the next guy.  We know it’s important for you to present yourself and your business authentically, and we appreciate that. Just make sure it’s the best representation of what you stand for. You wouldn’t show up to a first date in sweatpants and a dirty tee, would you?  Showing up disheveled doesn’t make us think you’re too busy being awesome to do laundry – it tells us that you don’t care what kind of impression you’re making.

  1. So does table-talk.

We’ve all been there – the awkward silences, blank stares or meandering answers that leave you with more questions than you started with. Avoid conversation collapse by coming prepared.  Be ready for a wide range of questions regarding your business and operations, and answer clearly and concisely. If you don’t know the answer, be upfront and follow up later. Being prepared tells us you’re serious about moving forward – and we’ll appreciate that you’re respecting our time.

  1. Be ready to talk about your baggage.

Far from being a red flag, your past relationship history can provide helpful intel for investors on the kinds of people you like to work with and whether we’d make a good partner. The reason things didn’t work out with other potential investors, past partners or co-founders aren’t flaws – they’re roadmaps to a better partnership. Similarly, skeletons in your closet aren’t necessarily deal breakers, but they’re way less likely to become obstacles if you’re upfront about them in the first place. It gives us a sense of the sorts of challenges we’ll face together.

  1. Finish Strong.

The end of the date will go one of two ways. Be gracious no matter what. How you finish the meeting is just as important as how you start. If it’s not going to work, don’t take it personally. It’s just as much about how we’re not right for you as it is that you’re not right for us. We don’t want to get into a relationship where we know we can’t add value – you deserve better than that. And it’s quite possible that while we might not be your perfect match, we have someone who would be in our rolodex. And how you handle your exit will determine whether we refer you or not.

We’ve seen the good, the bad and the ugly. So if you ever end up across the table from me and are struck by my first-date prowess, you can thank the Founders who’ve come before.