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Project W - Dancing with the Double-edged Sword: Failing Forward While Fundraising

By Emily Baum
01.13.23
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Starting a startup is an emotional roller coaster full of incredibly high highs and deeply low lows. As a former founder and venture investor, I can say without a doubt that both the highest and lowest points of the journey often happen during the fundraising process. Raising venture capital is a numbers game and most investors will say no, so founders have to be prepared to experience near constant rejection.

Humans are wired to avoid rejection, so the fundraising process is difficult for most founders. In fact, when scientists placed people in functional MRI machines and asked them to recall a recent rejection, they found that the same areas of our brain become activated when we experience rejection as when we experience physical pain.

And for underrepresented founders, the process of raising venture capital often feels rigged. Research has shown that "male and female entrepreneurs get asked different questions by VCs – and it affects how much funding they get." Women entrepreneurs get asked about risk and men get asked about opportunity, and, consequently, about $9 out of every $10 invested in startups is still going to companies run by men. There are tactics women founders can implement to navigate the difference in questioning, but carrying that extra burden is not easy. Additionally, women entrepreneurs are often told their valuation is too high or too low or that they are raising too much or not enough. Threading the needle can feel impossible and anticipating the rejection is a challenge to surmount.

So, how can founders stay energized and motivated when everything feels stacked against them? One of my favorite tricks is to aim to "fail forward" – to set a goal to get X number of "no's" from investors per week. When hearing "no" from an investor becomes reframed as a success, it makes the "no" feel less like a rejection more like a win. While it doesn't remove the barriers, it can make the process of pitching feel a bit lighter and less risky and create the feeling of momentum.

Most founders meet with 40+ investors at a minimum in their early rounds of fundraising to find only a handful who will say "yes," so lessening the weight of the inevitable "no's" can be a powerful tool to keep motivation and morale high during the fundraising process.

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