• Jill Volpe Kirk

The male dominated world of angel investing

There are some things I'm very good at - creating, big ideas, solving problems - and there are some things I'm not so good at - like pretending I'm something I am not.

Selling myself, my company, and convincing a complete stranger to hand over huge sums of money in exchange for equity in an idea are not things I had ever planned on doing in my life. But sales and pitching became a big part of the equation when Accomplish went from idea, to development, to reality. We reached out to every contact any of us had ever made, leveraged LinkedIn, networking events, entrepreneur groups on Facebook, and friends of friends to be connected to the type of people we believed would change our business.

We pitched Accomplish app to every person who would listen and we got better each time. Steve Jobs notably said that you have to do something for 10,000 hours before you're an expert at it - we're working our way every day to that number and getting close. Pitching became second nature - talking about this business and making connections were now natural and enjoyable. We left many meetings high-fiving in the elevator and congratulating ourselves on a job well done.

For a while, the only thing that mattered was our business, our plan, and our team. All of them were strong, but even still we prepared ourselves for the inevitable rejection when someone just didn't get what Accomplish app set out to do. We knew it was going to happen, and it did, but we were ready and the disappointment was not a setback.

What we were not prepared for was being rejected for something that we could not change - not our business, not the fear of customer acquisition, the difficulty to scale, or the relative inexperience of a team of young entrepreneurs - but instead, being women and mothers.

We sat down at a meeting with someone who could have been our perfect investor - he had a portfolio of companies with such synergy to ours and years of experience to offer. The conversation started off unlike any other we've had - not our backgrounds, not what drove this idea into fruition - but rather, the ages and genders of ours kids and if we enjoyed our time home with them. The saying "you don't get a second chance at a first impression" rang true here - from that first moment on, we were not business people with a strong business, stronger idea, and incredible work ethic. He began to see us as his wife/sister/daughter/mother, women he knew and liked but could not imagine doing business with.

So we allowed ourselves a day to dwell on this - how it was unfair, antiquated, shocking, and just plain wrong. When the day was up, we moved on and found ways to do better next time without compromising who we are: young, passionate, hardworking, business people - and yes, women and mothers.


There is a lot to be said for personal relationships and connecting to someone on a familiar level outside of work. However, when it comes to being a woman in a man's world, talking fluent "business" is your best bet. Forget the pleasantries of childrens' names, ages, and afterschool activities. If you both love wine and drive motorcycles, you can figure that out together once the business relationship is solidified.


Yes, it's annoying that this matters.

Yes, it's sexist.

No, you aren't going to be the one to change it today.

So overdress. Find a well fitting suit from the nicest place you can afford - invest in yourself. Make it full coverage, tailored, structured, and updated. Feel great about yourself in it and know that of all the things you will be judged on, your clothing won't be one of them.


These fillers words know no gender and both females and males should avoid using them. When you've practiced your pitch for 10,000 hours and you know your business inside out, these words will naturally fall away. But you will meet a person that is intimidating and you'll be asked questions you had not thought of before and when that happens, the filler words will fill right back in. Be aware of every word you're about to say - think before you speak. Take thoughtful pauses, consider the question, deliver an incredible answer.

Any other tips, send them my way!




New York, New York

support@now accomplish.com

  • Instagram Social Icon
  • Facebook Social Icon
  • LinkedIn Social Icon