As a teacher I’d cringe – watching the nervous, shaking, 14-year-old freshman read from his slides at the front of class. Did he get some credit for trying? Sure. Did I expect him to improve for the next presentation? You better believe it. And the expectations for preparedness, delivery, cohesiveness, etc. are much higher when you pitch your company to a VC.
In my combined years at Emerson Collective and Boost VC, I was fortunate enough to have observed hundreds of pitches, and read over thousands of pitch decks. Here are a handful of red flags I’ve observed that consistently derail a founder’s pitch:
1️⃣ Not answering their question(s)
One of the fastest ways to lose a VC on a call is when they become irritated, impatient, or worse: confused. I’ve seen VCs on calls I’ve been on exhibit all three, at varying degrees. And it’s almost always subtle. Most people don’t pick up on it, but my job at its core as an Executive Assistant and Chief of Staff was to study and read people. Most won’t tell you, or bother to dig deeper because they’re trying to be nice, or they don’t have the patience to ask you the same question 7 different ways to get at 1 response. Founders are typically doing the following to cause this:
Defaulting to vagueness (signaling the founder doesn’t know the answer to the question)
Diverting to adjacent details (to draw attention away from the question, signaling the founder doesn’t know the answer to the question, or the founder didn’t understand the question in the first place)
Brushing off the question with a rapid, surface-level response
Ignoring the question completely and proceeding down whatever tangent the founder is adamant about pursuing
To this last point, I remember being on a call with a founder, and my MD had asked him “how does your company scale?” His response: “This is a HUGE PROBLEM!” The vigor that accompanied his response didn’t shift the direction of the conversation, and my MD calmly responded with “Hear me – I’m in agreement that this is very much a problem. But with live tutors, how does this company scale?” He followed with a vague response about a training program for tutors.
We did not invest.
2️⃣ The pitch takes up 25 minutes of the 30 minute meeting
Your pitch shouldn’t take longer than 6-8 minutes (this is the sweet spot). You’re usually spending the first few minutes waiting for folks to join the call. Once everyone is joined in, you’re doing intros. At this point you’re about 8 minutes into a 30 minute call and you’ve said nothing about your company. See where I’m going with this?
You want to leave room at the end, so they can ask questions, and you can ask questions back.
3️⃣ Reading off the slides and/or reading a script while on a Video Call
Pre-COVID this wasn’t a huge issue, given pitch meetings were mostly done in person. But the standard today starts with an initial pitch video call, ranging from 15-30 minutes. It’s the most awkward thing watching two humans on the same call tune each other out. One: clearly reading from a script and switching between slides, not even pausing to take notice of if the VC is engaged, confused, curious, etc. The other: after watching you read from a script, 5 minutes in, decides to shift their attention to their inbox or X feed.
Whatever you do, don’t read word-for-word off every single slide – VCs can read it. Always start with intros, and then “so would you like me to run through the deck or just jump straight into the website or the demo?” and then add “feel free to stop me at anytime to ask questions” If the VC asks a question, don’t say “oh that’s coming at the end” and proceed through your presentation. They asked now. Answer it in that moment.
A founder’s inability to go off script is a huge red flag that the best VCs confirm. For instance, Naval Ravikant on Episode 1309 of the Joe Rogan Experience podcast said, “If you look at the most powerful thinkers, especially the ones where money or life is on the line, they have to understand the basics really, really well…when you’re memorizing, it’s an indication that you don’t understand. You should be able to rederive anything on the spot, and if you can’t, you don’t know it.”
During SXSW I attended a panel that two colleagues of mine were on, and what they had to say is gold, and I hope their advice echoes in the mind of every early stage founder:
“The biggest mistake I see founders make on those initial calls is they talk AT me….you want to let [the VC] drive the conversation. The 3 magic words you want to hear: Tell me more.” - Mike @ The Veteran Fund
Founders: if you’d like someone to help you hone your pitch, I’d be happy to hop on a 15 minute call. Shoot me an email or LinkedIn DM!
If you’re scaling faster than your systems, I offer fractional Chief of Staff support to help founders and GPs/MDs regain execution momentum. Drop me a line 👩🏻💻🦸🏻♀️