The First Date – Just Get Out the Slides

The First Date – Just Get Out the Slides


I have had a few meetings in the last few weeks that have reminded me how important some structure is for the first date – or at least when you are really pitching – just quit the “lets just talk it through and see the demo” pitch.  Bring out the slides. I am not kidding. Structure is sweet. I am sure your product is awesome but the demo isn’t enough for me. Unless you are going to levitate, go back in time or some similar Blaine like feat, I am not investing in a demo. I have a lot of awesome interactions and conversations at places like Philz.

Sometimes like this morning I had a meeting to talk with an awesome entrepreneur and she had just taken over as CEO of a company and wanted to get me up to speed on the business as they will be out raising money later this year. Perfect – no slides. No need. But I know her well and I know she will have a deck when she goes to really start raising money. No question. I learn a lot in unstructured meetings (unstructured does not equal without purpose) and hopefully the people I meet with feel the same. Those conversations are great – and they build relationships and trust which are critical – but I cannot imagine really making a decision over a latte. Maybe there are other venture investors that will so chalk it up to just my style.

I know it sounds cool – just talk it through and they will get it. Much more casual and much more fun. But don’t do it. Even if the investor says it’s OK – go to the deck. I am not talking about going through a mountain of slides. Tell the story succinctly and get to critical aspects of the business. The structure makes a huge difference – at least to me. Slides can be light on the details – no one can digest a page of numbers easily but they serve as the illustration to the story you are telling. Just get out the slides. Please. There is some complexity to any business and team and we are all short on time (and maybe I am short on intelligence) but some structured flow to the conversation will not only be the most efficient way to spend out first date but it will also be the best way for teams to get funding. At best, an unstructured first date just leads to a second structured one.

I have made the mistake of letting teams present to my partners in an unstructured way. Totally my fault and I let everyone down.  I made it harder for my partners to fully understand the material – even if they had seen the deck – and I made it harder for the team to really make their key points. Random questions are just terrible in a room full of people because the interaction generally focuses more on one person and then is somewhat disjointed which puts everyone into thinking about what is for lunch.

What you need to do is to engage people. It doesn’t always mean that they are asking questions though that is an easy metric, but it means they are paying attention. They are interested in what you are saying. If a venture investor isn’t interested in what you are saying, does anyone think funding will follow? In conversation, it is way too easy to digress, go down that awful rathole. But it won’t be driving the engagement you need to get to the next step.

I am not sure who out there is giving entrepreneurs the advice to just talk it out – some sort of hug it out fuzzy approach – but I think it is just flawed and not doing anyone any favors. Without structure, its hard to be efficient with time and while I like to think I am probably more liberal than most with first meetings, I really cannot spend the time again on a second if things don’t make sense to me. I really don’t care if its Powerpoint, Keynote, old school foils or Prezi etc. but its got to be structured and thoughtful. Put in the work to distill the story. Iterate on it. Its hard for me to believe that better communication won’t lead to a better outcome.

If you want money for 18 months – be able to answer what that means. Please keep the hand waiving to a minimum. Be direct about what you know and what you don’t know. I don’t expect precise answers but I expect you know directionally what you are doing with the business. I am backing you not some other person I hope to hire.

So back to that product demo – they are great but secondary. I actually like seeing demos. I know you have been working hard on it for weeks or months and its the showcase of all of your vision but its hard for me to see as clearly as you do without the rest of the context.  I care generally about two things – team and market opportunity and the combination of why you are going to win. If we have time – I would love to see the product but lets not skip the main event.

I am not that product person that just gets it. I would posit that the same is true of most venture investors regardless of how they position themselves. You might be tired of talking through the pitch one more time with yet another venture investor. I understand. But my sincere advice is to get over it. It is possibly the easiest thing you will do as an entrepreneur. Really. My partners and I do it when we raise money from our limited partners (our investors). I have come to actually really enjoy telling the story and structure really helps to keep things on track for what I know is a small allotment of time. I know how hard it is to re-tell the same story but there is no reason to make life any harder.

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