How To: Pitch Your Startup

According to folks who know how to do it good, I guess.

Hey friends!

Hope you’ve had a good week thus far! I’ve been superbusywithstuff… in and around the startup. TL;DR: I swapped twitter accounts and re-branded around “metacreator”-ish language. The evolution never stops.

Let me leave you with this… I had penned this for a friend who was preparing for a pitch and I realized that this might be more useful in the form of a blog post — so, here you go.

To infinity & community,

— john


An unbelievably-useful resource from Stripe on how to effectively pitch your startup. I’ve pulled a few things that I liked the most with some commentary below but this is worth a bookmark if this is in your zone:

Many outcomes important to startups are gated by pitching: the ability to quickly tell someone about your company and make them intrigued enough to want to learn more. You pitch your company every day to everyone—potential employees, investors, and prospects.

This is not a natural skill for many founders.

Sadly, this is entirely true and it’s not a natural skill for most founders. I didn’t know how important this was until I realized that it was stopping me from getting to the next major milestones for my businesses. My first real attempt (with a positive outcome!) was nauseating and scary.

Guess what? It still is, even now.

But, I don’t nearly freak out as I used to which is just to say: Progress.

Don’t sell yourself short! We all have doubts, insecurities, and places where our skillset isn’t where we want it to be. You don’t have to belabor these in your application. Remember, you only have two minutes. Describe what you’re doing and what you’ve accomplished, not what you couldn’t do and couldn’t accomplish. Failure is only as relevant as the insight you drew from that experimental result.

It’s hard to talk about ourselves in a way that communicates the historical truth without embellishment and without skipping important, meaningful details.

Okay, this:

Include a concise description of what exactly you are building and who should use it.

The most common problem, by far, among the pitches Stripe Atlas reviews is a lack of clear detail about what is being built. Reviewers use ability to describe what one is doing as a heuristic to determine whether one can successfully do it.

This has historically been the most challenging thing for me because I am often tempted to use “insider” language that assumes too much of my audience. The process of distilling down to the absolute, fundamental essentials is hard, painstaking work.

But, it is worth the effort because the person who is listening will actually get it. And that makes the difference between (early) success and failure.

Doing a startup means you are going to spend several years learning every nook and cranny of a problem space. You should already be thinking about this problem, in detail, and doing your research, both in reading voraciously and in talking to potential customers.

Make it obvious to your reviewer that you’ve already started this work.

It’s clear that you have to be a student of the space and problem if you’re ever going to build anything significant. It wasn’t always clear to me that this particular information was useful but I’ve realized that it’s one of the more powerful narratives that a founder and entrepreneur can share.

I can be a bit dense, most of the time.

A good pitch should have a clear narrative flow. What the future will look like and why, how we’re going to make it happen, and why we have the team and proof points to do it. It should tell a story, not just be a jumble of facts.

JOHN COLLISON, STRIPE

I pulled a pull-quote. LOL. But Collison is right: You need a clear narrative that clearly communicates what the future will be when you win. If you can’t do that then you won’t be able to successfully build a product that holds the narrative in a powerful way and is able to be executed with precision, you won’t be able to recruit talent because they will be confused as to what you’re building (and your clarity or lack thereof), and you won’t be able to convince anyone to give you money.

It is what it is. Never forget: We believe and love a leader’s integrity but in reality we’ll oftentimes choose to follow clarity.

Cite metrics correctlyespecially revenue. Do not cite gross merchandise volume (GMV) as revenue; if you facilitate a transaction between two parties and collect a fee then the total transaction is GMV but only your cut is revenue. Do not cite one-off payments for a long service as revenue in a particular month; an annual contract for e.g. software might be invoiced in March and collected in April but the revenue is recognized evenly over the period of service, not all in March or April. Fudging revenue suggests malevolent intent or incompetence.

You might be so early in your company that you don’t have good instrumentation built yet to report metrics. This is common, but you should at least demonstrate understanding of the metrics to convey that you will make data-driven decisions in the future.

All data can be crafted into a compelling narrative but not all narratives are true. Good investors can’t tell the difference while great investors see the nonsensical bullshit before they even open the deck.

Or, maybe they have to open the deck.

You need to make the reviewer’s first few minutes with your software absolutely sing.

There are some pretty fun ways to do this; the more creative the better. Most technical founders will never be able to ship something that doesn’t technically work the way it should and this misses the point entirely (and we lose out on opportunities to progress the conversation forward as a result).

Be willing to kill your ego a tad so that your startup can get the capital it needs. I have a big problem with this as well, to a real fault. So, I’m struggling to write this as I type it.

This is a gem at the end:

Don’t give up. This will not be the hardest moment in your company’s life; dust yourself off and try again. Improve yourself, your company, and your pitch for the next opportunity.

A single pitch isn’t shit. You’re going to do it thousands of times. Sometimes it’s going to land and you’re not going to really understand why it does while other times you may have “killed it” and yet the audience leaves scratching their damn head.

The point of the exercise isn’t just to convince them that you matter; it’s a way to practice communicating clearly that your project and your dream already matters in very meaningful ways and they simply haven’t figured it out quite yet.

See the difference? Keep going. Don’t give up.