Ladies…make the BIG ask

Consistently but not always, women tend to cross their t’s and dot their i’s which is a good thing but sometimes it is a bad thing. Making that big ask to put a foot on the gas and attempt to hit it out of the park is not always how women operate. We tend to be more methodical just like crossing those t’s.

Venture Capitalists want founders to manage to the upside not to the downside. You certainly should be aware of the downside but it is all about attempting to hit it out of the park. If you don’t try to swing for the fences then someone else might come in with a bigger check and compete. Most of the time being the first to market can be game changing.

Also, VC’s don’t care about losing the money because that is part of the job. It doesn’t feel great losing millions on a company but that is the risk of the business they are in. They want to see big hitters not people who are just looking to get to base hit by hit.

If it is obvious that your business is at the point where money changes the game because product market fit is right there, then make the big ask. Women need to get better at making that big ask meaning more than you think you need.

Comments (Archived):

  1. awaldstein

    Quite insightful”Venture Capitalists want founders to manage to the upside not to the downside.”I agree.Also as someone who has both won and at other times not been able to make payroll, understand the innate friction and just madness that is what entrepreneurial ceo’s must live through.

    1. Gotham Gal

      lots of madness for sure!

  2. William Mougayar

    “ If you don’t try to swing for the fences then someone else might come in with a bigger check and compete. Most of the time being the first to market can be game changing.”- so true. Even men founders can make those mistakes. I recently turned down funding a (male) founder because he was ultra conservative in his go-to-market. Although he had a good product, he was afraid to swing for the fences, and kept everything close to his chest and seemed happy with a handful of customers instead of blazing out to the world what he had developed to gain top mindshare and pull many more users for his products.He got some money from casual wealthy people he knew (who don’t have VC experience), and none from professional angels or early stage VCs. Classical mistake situation, often made by first time entrepreneurs coming out of a corporate environment where the product entry process is more measured and deterministic where they want all the answers (t’s, i’s) before going to the market.

    1. Gotham Gal

      Def classic

  3. LE

    Making that big ask to put a foot on the gas and attempt to hit it out of the park is not always how women operate.You see this (and not me) and have identified it as a ‘woman’ thing so it’s almost certainly correct (with startup raises) but what I have seen in both men and women is a tendency of what I will call ‘negotiate for the other party’. That is this idea that there is no point in asking because ‘oh they are not going to do that’. This actually applies to all types of situations. As only one example (and I have many more) I was giving advice to both of my sisters when they were buying condos and all I kept hearing from them was ‘oh the seller is not going to go along with that’. Ditto for my wife when she was negotiating a raise for her job.I do think that women have been raised to not be bold and/or ruffle feathers.That said attached is an email that I got from a woman who wants to rent some medical office space. I’ve made her a really good and flexible deal (if I may say so). Yet she keeps coming at me! (I think this is great and I told her that in the reply as well.). By ‘coming at me’ I mean she doesn’t just take what I say and then think ‘oh wow he will never do X so I guess I have to move on and find something else’. And she needs the space it’s the most convenient to her existing business location she needs it for expansion…. https://uploads.disquscdn.c

  4. pointsnfigures

    Active language. Makes a big difference. I don’t agree that VCs don’t mind losing money-they do but realize losses come early and are a part of it as you know well…