How to Pitch Like an American

Americans are born confident. They pretty much come out of the womb oozing confidence. So much so that the rest of the world often mistakes it for arrogance.  But in many aspects of life, American confidence — born of a deeply held belief that success is manifest destiny — is an unfair advantage.

In fundraising, it’s a game-changer.

As Canadians, we’re taught from a young age to be humble. We’re famous the world over for apologizing for everything.

In most contexts, our national propensity to say ‘sorry’ ends up little more than the butt of well-meaning jokes. But in the context of pitching, our collective humility is often mistaken as weakness, particularly by U.S. investors.

Why?

The average investor meets dozens of founders each week.  For investors based in Silicon Valley, the vast majority of those founders are — you guessed it — American. VCs are only human (believe it or not) and humans are prone to pattern match. If I meet with confidence-oozing founders who pitch as though their success is preordained every single day, when I talk to anyone who doesn’t exert that same level of confidence, they will likely come across as weak, inadequate or lesser. 

Sure, you can argue that as an investor, I should know better, but the reality is that most VCs look to invest in companies that feel inevitable. Projecting confidence is a big part of that.

Here are 3 ways that even the most mild-mannered Canadian can project confidence when pitching:

1. Answer First, Explain Second

When asked a question, most Canadians (and, in fact, most people from across the Commonwealth) respond using the format <explanation>, <answer>. As in:

Investor: What is your revenue?

Founder: Well, we just started monetizing a few months ago,…

By the time you eventually answer the question, I’m convinced that you’re making excuses. So even if the answer is awesome, I’ll have already discounted it. Instead, answer the question directly, then add any context:

Investor: What is your revenue?

Founder: We’re currently at $1,500 MRR. We just started monetizing a few months ago,…

Even in written form, the second version clearly comes across as more confident than the original.

2. Answer First and Don’t Explain

Want to project even more confidence? Hold off on providing any explanation until/unless the investor asks:

Investor: What is your revenue?

Founder: We’re currently at $1,500 MRR.

For a lot of people, this is really hard. The need to justify answers and provide additional context can be almost overwhelming, but keep your mouth shut! If the investor wants to know more, she’ll ask (I promise).

In many cases, you’ll be surprised to find that investors don’t actually care about the details you often dive into. Most people neither want nor need all that context. Being concise projects confidence. For founders who feel like they talk too much, this is a great strategy for staying out of the weeds, which is especially important in first meetings.

3. Be Proud of Every. Single. Answer.

Many founders I’ve talked to feel like fundraising is a school test: if I give the right answers, then I’ll pass the test and the investor will give me money. But that’s not how it works.

Yes, VCs look at metrics like revenue when making investment decisions, but they also know that in order to make a billion dollars you have to start with one.

For most investors, there is no “right” answer to the questions they ask. I’ve passed on startups making millions in ARR with the same conviction that I’ve invested in pre-revenue companies. The questions I ask help me to understand where you are in your startup journey, in order to figure out if your company (at its current stage) is a match for my investment thesis.

What I am definitely looking for is confidence in your answers. That means being proud whether you’re at $100 MRR or $100,000 MRR. Whether you’ve just signed your first pilot agreement or closed your 100th customer. The more confident you are in sharing your journey with me (both in terms of where you’ve been and where you’re going), the more confidence I will have in you. And I need to be confident in you in order to invest.

Be Hungry and Humble

This isn’t to say that confidence is everything. There’s a fine line between confident and cocky.

In my experience, the best founders are “hungry and humble.” They have supreme confidence in themselves, their team, and the opportunity they’re going after, a hunger to win, and the humility to learn and absorb new information along the way. In other words, the confidence of an American and the humility of a Canadian.

Hmm…on second thought, go out there and pitch like a Canadian. An Olympic gold medal-winning Canadian.