A Queens Tale

Fears, Boxes for Boxes, and Those Pesky "Deck" Pics… Life as an Entrepreneur and VC.


Kimmy Scotti grew up in a strict Southern Italian family in Howard Beach, Queens. When she was young, her father made her wear a Catholic schoolgirl uniform to school. This would have been normal had it not been P.S. 207, a public school where no one aside from her siblings wore uniforms!

Her father’s strictness, however, also had a positive side. It instilled a powerful work ethic in the already bright girl, and Scotti excelled in school. She went to FIT for college and upon graduation found a job in Manhattan working for serial entrepreneur and investor Michael Loeb.

After only eight years, she worked up to Executive Director at Loeb Enterprises, yet something was still missing…


After 8 years, you left Loeb this past January. Why?  

I remember hosting a conference at Michael's home in Southampton with all female entrepreneurs and we were talking about what our dreams were.  I remember saying that I wanted to do exactly the same thing that I was doing with him, just by myself.

What were you most scared of, breaking off on your own?

I was most scared of not being able to do this by myself without Michael.  Having an amazing business partner means that you have a lot of warm introductions and a wealth of business experience behind you.  I was really trained at his knee - which was super lucky. I guess that even now, that is still my greatest fear, of not being able to do it without him.

What were you most excited for?

To be able to define my own thesis and brand.  Regardless of the fact that we worked together for a long time, I still had things that I believed in that didn't get his pulse racing.  But, since January, the sky’s the limit, I can now explore those interests.  

What is your thesis?   

On the seed stage side, we focus on tech-enabled consumer and vertical enterprise software.  One of my favorite deals has been Omni, a tech-enabled self-storage solution.  The founder, Tom McCleod would say that it’s an extension of your closet.  When I talk about the kind of entrepreneur that inspired me to become an investor, Tom is on my shortlist.  I’m always looking for people with that passion and fervor about their product.  

How is the environment for a female investor?  

I’ve found that most women entrepreneurs are always like, “thank God you’re here, we need more females on the investing side.” I’ve seen tech-enabled lingerie brands pitching products to male investors who have to pull their assistants in their offices because they don’t understand the product.  Females represent +80% of household consumption, but it is mostly men who are investing and building products.  Getting more women in venture and STEM careers in general is helpful because we’ll eventually get better products out of it. While I’m definitely a feminist, I believe in people and love working with men.

What is the most frustrating question you receive as a female VC?

I think the most difficult thing that happens but less so now, is that people bring you "girl" things to evaluate rather than just allowing me to evaluate all different kinds of deals that I could be interested in. I want to see everything, so bring on the referrals! I think the worst thing that happens is kind of hilarious. I'll be on a date and the guy finds out what I do, and the next day, I get the dreaded 'deck pic'..."Hi Kimmy, I thought I would share what I'm working on..." The end. No second date. Lose my number!

You are building a company called Monthly Gift, what do the ladies of the world need to know about it?  

Upon launch, Monthly Gift is going to look like a subscription service for feminine care, but the most important thing to know is that we’re launching a woman’s healthcare business, focused initially on femme-care because we can solve a pain point for every women by providing a convenient and cost effective solution.  We’re providing the only fully customizable “bespoke box for your box.”  Monthly Gift allows you to fully customize your package.  You choose the tampons, liners, and pads that are right for you - all for one price.  Every woman is getting exactly what she needs when she needs it, without ever having to leave the comfort of her own home.  We’re tired of how sterile the big brands are in the market. There’s an opportunity to build something that is feminine and feels like a luxury, but delivers on value so no matter if you add pads or liners everything will be delivered for as little as $10.  

If a crystal ball could tell you the truth about yourself, your life, the future or anything else, what would you want to know?  

I don’t know that I’d want to know anything.  I’m really having fun stumbling around and figuring out what the next step is.  I still think that the unknown is more exciting than knowing what’s going to happen next.

Michael Farber & Paul Prentice / Breakout

Graham CohenNYCComment