• Kale

Startups, 3 keys to not blowing your big pitch

Stop listening to advice from people who have never been in your shoes and do these 3 things.



I’ve been there. I’ve fucked it up. I’ve rambled on and stumbled over neatly prepared slides.

I admit this because you are likely getting a ton of advice (whether it be in person or other books/articles) about how to pitch your startup to investors and most of them have never actually started a company.

Yeah sure, they’ve invested in startups before. They’ve sat through tons of pitches just like yours and now are “experts” who can provide unchallenged advice to you but oh wait, they have no intention of investing in your company.

Think about this real quick — you are going to listen to the advice of someone who, even after telling you exactly what to say, wouldn’t give you a dime.

So what this really is is an ego-driven asshole lecture with zero actual value. With that said, you still do need quality advice from someone so you can avoid as many mistakes as possible. This won’t insulate you entirely but it’s a needed head start that most won’t have (because they’re listening to the asshole I just described and copying AirBnBs pitch deck).

Don’t just type it out and memorize verbatim

So you have a pitch coming up and hopefully, you’ve put together a half-way decent pitch deck to provide cover fire as your enemy (the investors in the room) look for any vulnerable angle to attack. I may come off as aggressive here, but most of these investors have never gone through your struggle and get off on finding holes in your plan (news flash — there are holes in every single plan ever as the future is unpredictable).

With this framework, it’s time to write out a basic script (or at least key points to make) for each slide.

This shouldn’t be a novel but should include all the key points you need to make.

Next, actually read this thing aloud while you go slide by slide through our deck. You can do this alone the first time through.

I’m going to save you the surprise (unless you are an absolute killer and paused reading this article and immediately went and did that) and tell you that you are going to realize that it doesn’t work well.

So that’s why you need to start chopping here — cut each slide’s script down to a few words or a few key statistics/numbers that need to be said. This means cut the shit/fluff. With that being said, what you intend to say should not be anything you have displayed on the slideshow directly behind you.

Believe it or not, people can read. Also, the more words you put on the screen behind you the less they will actually listen to what you have to say (no matter how important it might actually be). I won’t get too deep into this pitch deck here, but keep it incredibly simple with less than 5 words per page if possible (1–2 words is even better).

So once you have a bullet-point, abbreviated script drafted — do a full run-through in front of another human being or a camera. Yeah, it’s awkward. And you will stumble and fuck up the first 5–10 times you go through it and likely realize that the order should be adjusted.

But aren’t these all things that you’ll be glad you took care of before you are actually in front of a room of people? I thought so.

Keep doing this until you can do the entire thing in your sleep and without having to hold any notes in your hand during the pitch (not a good look).

The key point here is to go beyond making a shitty slideshow and writing down a full script. Practice it, figure out what comes across as awkward, and make sure you can do the entire thing without having to rely on notes or look at the screen behind you.

Expect the hard questions to be asked and be ready

I said it above and I’ll say it again, these people are here for a show and to see how they can show how smart they are.

If you leave out a basic but essential detail, like how you are going to make money or what your traction is to date, you will be called out on it.

Here’s what I recommend you do:

Make a list of every single “business killer” for your company (everything from not being able to acquire customers, to changing legislation, to lack of IP to protect competitor imitation).

For every killer, have a reasonable response. (Honestly, this is a good thing to have in general as a company early on so you can have a basic “reaction plan” when shit hits the fan)

Then, make a list of every question that you would ask yourself (or someone like you) who was about to ask you for $1 million dollars. I don’t care if you are raising $20,000, money is money and investors will be equally as unhappy to part with it for both so you need these questions answered.

These should be things like — how many active users do you have now, how much revenue are you earning, what’s the profit margin, what exactly will you use the investment funds for, what impact will these actions have on making your company more money.

Honestly, once you get started it’s not that hard. Especially if you put yourself in their shoes. One of the biggest breakthroughs for my own startup was realizing that I wouldn’t give us a Series-A round either unless we had X thousand user count, XX% monthly growth, and a positive profit margin very early on. This shouldn’t have been a crazy realization, but too often as a founder you will get too close to your business and forget that the outside world (investors) are really only interested in how you are going to make them rich and how much risk exists that you aren’t telling the truth.

We decided to push off fundraising for 6 months so we could run a full Beta and have solid data to back us up. This proved to be the right call and also gave us needed leverage early on so we didn’t get completely fucked in our pre-money valuation.

In summary, plan for the questions that have the hardest answers (the ones that keep you up at night) and make sure you are thinking about it through the frame of someone departing with $X thousand or $X million dollars.

Get to the point (not the PowerPoint)

The best piece of advice I ever received about pitching is that you have about 20 seconds to convince everyone in the room you are worth listening to or they will tune out.

How can you tell if you’ve lost them? From personal experience: email checking, texting, looking away from the front, flipping through whatever is in front of them, or some combination of all of these.

You need to make sure that you come in hot.

This does not mean a really cool slide with your company name on it and a shit ton of logo porn (aka, the million companies that you are “associated with” — when really you just had that one meeting one time with a guy who works there).

This means leading with your most compelling shit, getting everyone to sit up a little straighter in their chairs, and then carrying the room for however long you have their attention. For example

— we are a drone food service delivery company that drops off your food in less than 10 minutes and has 10 million users on our waitlist (or even better, actively paying).

I’d buy that.

I know what you are thinking. You don’t have a million people signed up and you have not made any sales yet. That’s ok and actually the norm for most fundraising below $200,000.

But there has to be something about your company or your team that is going to lead to a “wow” moment, or the best you are going to get is “let’s stay in touch”.

You worked in the space and helped develop a similar product that made a ton of money? You built a company before and sold it for X amount? You have a waitlist with X many people on it?

Just have something memorable and get the words out of your mouth in the first 20 seconds you are given the room/microphone.

If you do this and don’t make a rookie mistake and think a pitch deck should be structured like a murder mystery with the “big reveal” at the end, you just may have 80% of the room pay attention to you (the other 20% aren’t going to listen unless you shoot a cannon through the wall so don’t let it get to you when a few folks are still playing on their iPhone during your life's biggest moment to date).



These should help — but having a great product or service that people actually want to pay for is obviously the essential component.

Without it, no matter how smooth you present, how well you are prepared for questions, and how strong you come out of the gate, you will remain trapped in a perpetual pitching/fundraising cycle that only ends when your emergency fund runs out (please save up for an emergency fund people, good things take time and money).

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