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A British Criminal Barrister's guide to pitching investors in Silicon Valley



I specialize in helping founders and management teams create and deliver outstanding investor presentations. Over the past 10 years I’ve listened to 100's of pitches from companies at all stages, from seed and series A, B, C through to PE exits and IPOs. I started my career at the Criminal Bar in London where I spent several years prosecuting and defending jury trials. Recently, it struck me that there were many similarities between the techniques barristers use to prepare / run a criminal trial and how founders prepare to pitch investors, so I decided to share them…



Start with your closing


When you are preparing a criminal trial as a barrister, you start by preparing your closing speech. This is the last thing the jury hears from you before they retire to make their decision so it needs to include all the crucial elements of your case and be highly compelling. Once you have identified the key messages for your closing, you then go through all of the evidence available to you, witness statements, DNA, police interviews and whatever else you have, drawing out from that mass of material the elements that support the key messages of your case. Everything else is noise.

I apply this methodology to preparing an investor pitch. Start by working out the handful of core messages that absolutely need to be lodged in the investors’ mind when you leave the room, then work back from there, pulling out supporting evidence and memorable colour. In working with startup founders, one of the most common problems I encounter is information overload. Founders can literally drown in their own story. What stays out of a VC pitch deck is just as important as what goes in…noise is a big distraction.


Tell a story


People remember good stories, they don’t remember collections of facts, or a bunch of apparent non-sequiturs.


Jurors debate between themselves in the jury room — if there are ten in favour of convicting, then those ten set about persuading the last two to do the same. They make the arguments on your behalf — you’re not there anymore, but they are taking your case and arguing it for you. They can even become the champion for your case in your absence. But, they can only do this effectively if they can remember it! Therefore the story is key, it needs to be exciting, concise and memorable.


It’s the same way for the VC who’s heard your pitch — they have to be able to be an advocate for your company with their other partners on the investment committee. You won’t be in the room. They need to advocate for you, so tell them a story they believe, that is crisp and that they can remember.


Credibility is key


A judge will specifically direct the jury to carefully consider the credibility of all the witnesses, so don’t be far-fetched. Avoid hyperbole, because do you believe the person that over-exaggerates everything? No, you automatically discount it; it turns you off. Measured enthusiasm that exudes confidence beats jazz hands any day. Even in Silicon valley.


Adapt, but stay disciplined


Stay disciplined. You’ve prepared your case and you’ve worked out what needs to be said. You did all that prep for a reason. As the trial proceeds and things are going well, you can be tempted to ad lib a little — after all the jury are with you, hanging on your every word and even smiling when you crack a small joke. So what could go wrong?


Just about everything.


It's obviously important to read the verbal and non verbal cues from investors, and react accordingly, doubling down on clear areas of interest and being respectful of lines of questioning. But, something I see a lot is founders who warm to their theme, stray off track and cumulatively build on their script, forgetting the central story.


Another problem can be boredom — suddenly deciding, mid-presentation, to completely reinvent the wheel and tell your story in a totally different way. Don’t do that on the fly!


There is always a great way to tell a story; once you’ve worked out what that is, then stick with it.


Questions — have the confidence to stop talking


Know when to sit down. It’s all going your way… you’re on your feet cross examining and the answers are spilling out, building your case for you one by one.


And then whoops you ask one too many. You get the wrong answer and all your patient work is undone! Your case is under-mined. If only you had just stopped talking.


The investor analogy here is centred around answering questions rather than asking them. When responding to a question, make sure you answer it, be succinct and have the confidence to stop talking.


Make eye contact and engage


Eye contact is crucial. As a lawyer, you don’t open your case to the judge, or the back wall, you turn and face the jury and you look them all in the eye.


You don’t talk at them, you talk to them, engage, measure reactions and adjust. A script is a terrible thing — if you’re reading your lines, it doesn’t sound like you mean your lines. You come across an insincere. Ploughing on regardless, ignoring the wrinkled brow, means your audience gets left behind. And then they just give up.


Juries are a group of human beings who have their own prejudices. They bring these with them into the courtroom. They might think they know how this is going to end up at the start and just want to ask a couple of questions to confirm this before convicting, but they don’t know what there is to know! Barristers don’t just stand there and let the jury ask a couple of questions before retiring to make their decision! They present their case.


The same goes for investors who maybe didn’t want to take the meeting, or who maybe think they know your business better than you do. But they did take the meeting, and it is yours as much as theirs. Don’t let them hog it; you have to hold the room, tell your story and make your points. They can never know your story as well as you, so make sure you get it out there. It’s your chance to make them see opportunity for your business the same way you see it.


So there you go. Many parallels. I miss my days as a barrister, but at least as a pitch coach I don’t have to wear a horsehair wig…those things are itchy.

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© Claire Macmillan