Stop Pitching So Hard
I realized a funny thing this past week.
Since we began Presentality in late-2017, we’ve worked with hundreds of entrepreneurs and companies on how to pitch better. We’ve rebuilt story lines, redesigned decks, and reshaped body language.
But never once have we questioned the basic premise of this work: Is there a problem with pitching itself?
By this, I don’t mean to get into the whole venture-backed vs. bootstrapped debate, and I certainly don’t want to play the semantics game like “let’s replace ‘pitch’ with another word!”
Rather, I’m thinking about the whole set of terms that are often associated with pitching — persuasion, charm, selling, convincing, projecting confidence, etc. — qualities made glamorous by movies and TV shows casting slick-tongued charmers as heroes.
And more than just words, I wonder about the “mindset” that comes with these words — a mindset we’ve observed in too many teams over the years:
- “I want to project confidence and warp reality like Steve Jobs did.”
- “I need the right words and deck to convince investors to give us money.”
- “We have the best technology, but I’m not a salesman like [x], or I could talk all these investors into giving us millions.”
Implicit in these statements is the belief that by wielding the forces of persuasion, entrepreneurs should be able to turn many (if not most) investors they meet into passionate backers.
So… What’s the Problem Here?
“So okay, they really want to win investors over,” you might say, “What’s the problem with that?”
The problem is that, especially for inexperienced founders who haven’t been through the fundraising grind, this mindset can drive some rather unhelpful in-meeting behaviors, such as:
- Going motivational — projecting so much confidence and speaking theatrics that the founder almost becomes a motivational speaker.
- Getting salesy —using over the top praise to describe their own products and services, team capabilities, and market opportunity, etc.
- Turning defensive —the moment investors challenge them on product, direction, etc. (even mildly), they get defensive and even become offended.
- Spraying information —if the investor doesn’t agree, it must be because they don’t have enough information! Answer: overload them with info.
*Some founders also fudge numbers and blur truths to seem more impressive, but we’re wading into ethical territory there…
If you’ve sat in pitch meetings, you’ve likely seen these behaviors before. And they do NOT help the entrepreneurs. In fact, they do the opposite.
With most savvy investors we know, motivational and sales theatrics get filtered right out (or even raise suspicion that the “substance” isn’t solid enough), while defensiveness and info overload make investors less willing to work with the entrepreneur.
Don’t Try to Charm Everyone
From talking to a lot of founders, I also detect a hidden assumption behind these behaviors. Many of them go into fundraising with the expectation that — with the right presentation — a large portion of the investors they pitch should love their ideas and support their business.
Each meeting is a new opportunity to charm funders, and hope, as they say, springs eternal.
Except… most investors fund a minuscule number of companies they meet (Like 5 in 1,000), and most startup will literally go through a hundred meetings to find one backer (if any).
*In fact, even well-respected investors find their fundraising process to be a tough grind, as the tweet here makes clear (I’ve even seen VCs doing thousands of meetings to raise their funds).
Trying to charm everyone, in other words, is neither the right approach nor the best mindset to have.
So what’s the alternative?
Try to Find the Right One
Rather than trying to charm everyone, founders should go into investor meetings to find the right one.
It’s a small shift in mindset that can make a big difference.
It’s not about you pitching and them judging, but about both sides engaging in conversation to figure out if you’re the right fit.
After all, if the founder-funder relationship is indeed a partnership, a “marriage” even, it should begin with conversation, not judgment.
It’s not about giving the most impressive pitch, but about telling the clearest story to help them decide.
Your job is to help investors understand — with the least amount of friction — who you are, why you’re doing this, and how you’re different. It’s not about dressing your pitch up with fancy slogans and trendy design, but about cutting down unnecessary words and confusing graphics that stand in the way of understanding and connection.
It’s not about batting down their objections, but about learning from their insights.
If investors challenge you, your job isn’t to defeat them in an argument so they’ll go: “Ok, you win, we’ll invest.” After all, they may not even be the right investor for you! Instead, you could:
- Clarify misunderstandings: After all, you don’t want a potential partnership ruined due to a misunderstanding. Try to spot where things were unclear in your story.
- Assess fit: You can often tell by their feedback whether they’re the right fit for you (e.g. “we just don’t see potential in this market” or “we don’t believe in this approach”)
- Learn from them: They may be challenging you based on valuable experience and insights that are applicable to you. Draw these out with humble questions, NOT defensiveness (more on this in a later post).
If you understand this, you’ll know that there’s no point in getting defensive. If there’s a genuine difference in perspectives, learn from them. If you feel offended by the way they treat you, maybe they’re just not right for you.
Above all, relax. Stop pitching so hard and trying to make every investor submit to your greatness.
You may read about hot startups being chased by every top tier VC, and aspire to be like them. But more likely you’ll be pitching hundreds to find the right few — like many venerable startup successes did.
So don’t charm everyone. Find the right one.
And if you don’t agree, well, maybe this article just isn’t the right fit for you.
