Imposter Syndrome Fundraising Mistakes

Jason Yeh
June 25, 2021

A variety of studies estimate anywhere from 2 out of 5 successful people all the way to 70% of the entire population experience imposter syndrome. I’ve certainly struggled with it in my career. First-hand experience has helped me identify when it rears its ugly head during fundraising. 

In a live pitch workshop for the last cohort of Fundraise with Confidence, I saw multiple founders make two mistakes that I attribute at least partially to that common affliction. 

If you deal with imposter syndrome at all, look out for these two blunders in your fundraising pitches.

  1. Rushing past small talk
What those with Imposter Syndrome do vs. what they should do


During the workshop, I asked students to engage in a mock live pitch on Zoom. We set up the exercise to accurately reflect a real-world call, starting each mock pitch from the time the call connects. 

A lot of entrepreneurs think about how to jump into their pitch, talk through their slides, and begin their script, but they don’t consider the importance of the first few minutes engaging with an investor. It’s huge. Those few minutes provide a critical opportunity to connect with investors on a human level and can materially affect the investor’s perception.

It can feel awkward for some though. A couple students in particular heard simple questions like where they were from, gave one-word answers, and then immediately began their pitch.  

Especially if the thought “I’m not supposed to be here…” creeps into your mind, you may be tempted to blow past small talk and begin talking about your company. I understand the anxiety. It’s a feeling that if you don’t start talking about something substantial, you won’t be able to convince them that you belong. 

Fight that feeling. Allow yourself to engage in natural, non-company-related conversation before comfortably switching the focus back to your pitch.

  1. Answering questions that weren’t asked


Don't over explain.

One of the things I preach in fundraising is telling a concise, punchy story that quickly hooks listeners with just enough interesting detail to make an investor want to learn more. The enemy of this gospel is the nagging thought “they don’t think I belong here,” because it can lead to “I need to tell them more to convince them."

In my workshop, that behavior showed up in two ways. The first was founders would come to a slide that made a nice big point and proceed to deliver all the supporting details. It bogged down the listener’s thinking and slowed down the escalation of excitement. 

The second happened when an investor chimed in mid-pitch with questions. They asked “What market are you starting with?” Instead of a confident, concise answer like “We’re starting with small businesses who have the greatest pain,” the founder proceeded to break down their decision-making process, the pros and cons of other markets, and how they planned on growing to other markets in the future. 

The investor didn’t ask for all the details. If they actually wanted more information, they would ask.

Small questions can trigger imposter syndrome as founders think to themselves “they don’t believe me.” That again leads to “I need to prove I belong!” Next comes the deluge of over-explaining and answers to questions that weren’t asked. This breaks flow, kills momentum, and wastes valuable time that could be used covering more important things.

When investors ask questions, remind yourself that’s their job. Believe that they’re excited about you. They wouldn't have taken the meeting in the first place if that weren’t the case, so answer with confidence and move on.

You belong.


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