Please Meet: Cayla Weisberg

This week, we’re revealing our panelists one by one for the 3rd Annual Little Black Dress Night. We want you to get to know our panelists ahead of the event. Today’s reveal is Cayla Weisberg, Partner at InvestHER Ventures

ChiTech: What led you into tech and entrepreneurship?
Cayla Weisberg: My hunger to begin working started in high school, so at 15, I found my first job at a retail store. It was working there that inspired me to start my own business. So, when I was 16, I launched a concierge shopping company which I scaled through high school and college. After I finished my bachelor’s degree, went to work for a Fortune Top 100 company, and developed my fundamentals in business. I stretched myself every day to become better and better and hone in on my craft. After four years and four promotions, I became assistant director, leading a sales division.

At 24 years old, I had an itch to enter back into the entrepreneurial world, so I took a major risk by leaving my cushy job at a well-established company to join a startup to lead sales efforts. I then became director of accounts and sales for another venture-backed tech startup. During these experiences, I noticed there weren’t many female entrepreneurs getting funded, and realized that it was much harder for women to secure capital. After meeting my business partner, Gerri Kahnweiler, we felt like it was our mission to jump in to help solve these issues. In April 2015, InvestHER Ventures was launched, and we have only invested in female technology founders since.

Why does so little funding go to startups led by women?
Without connections to investors or tech leaders, it’s so much harder for women to get access to capital. The startup community is still a boy’s club, unfortunately for women. We found that in 2016, only two percent of venture capital money went to women. Thankfully in Chicago, investors are beginning to share insights about their female-led portfolio companies, shedding light on how important it is to diversify. But at the end of the day, access to capital and to resources are the two pieces that make it harder for women to achieve the same equality their male counterparts have. Statistics show that women-led companies achieve profitability or exit much sooner and have higher valuations than their male counterparts.

How do you see yourself making an impact on INVESTHer company in the next two years?
We’ve already made a huge dent in Chicago, but there’s still so much work to be done. In 2016, we met with over 200 female tech founders and made eight investments since our launch last April. Our plan is to continue to take action instead of just talking about equality.  This includes continuing to invest in new startups, but also help our current companies grow and working on bigger issues like getting strong, competent women board of director seats.

What lessons did you learn from running your own business from a young age?
Stormy seas make the skillful sailor. It is a constant battle and things are hard. But if they’re not hard, you’re not going to improve yourself. I’ve learned to surround myself around really smart, interesting people who have accomplished great things. My advice is to make entrepreneurial friends who you can share best practices with and push you to do better.

What did you want to be when you were a kid?
I always knew I wanted to be involved with my community and inspire people.

What are some of your goals, professional or personal?
Professionally, I’d like InvestHER Ventures to be the #1 sought after destination for female founders across the US. Personally, at the end of the day, I want my family to be healthy, happy and financially secure.

What do you see as your biggest accomplishment so far?
Having a hand in solving the gender gap for women in technology. This is a huge issue that will only be resolved by action, rather than talk. Meeting my business partner, Gerri, was one of the best things to ever happen. Without her, our fund wouldn’t exist. The opportunity I was given to grow and nurture our brand, and give back to the female entrepreneurial community the way that I have, has been the most rewarding personal and professional experiences of my life.

Can you give me three words you would use to describe yourself?
Optimistic, enthusiastic, energetic

Who are your heros?
My husband, Brad. Every single day I am in awe of his strength, courage, tenacity and kindness. He pushes me to be my absolute best and makes me an all around better person. I would not be where I am today personally or professionally without Brad believing in me and helping me along the way.

I have to also mention my Mom, who has been my hero for 29 years and counting. She is a light in my life that has shaped me into who I am. Love you, mom!

When you were in high school, what was your favorite album?
I was all about the Spice Girls. Girl power all the way! It was my first concert, and I had posters all over my room.

Which Spice Girl was your favorite?
Posh Spice was my favorite, but I was elected by my friends to be Ginger Spice for Halloween one year because my hair was red.

What is something not a lot of people know about you or you wish people knew about you?
I’m secretly a homebody. I come across like I’m the ultimate extrovert, but I spend a lot of time meditating and reflecting and working on personal development. What I’ve learned in my life is that you are who you surround yourself with. And, at the end of the day, the most important person you’ll ever spend time with is yourself.

Do you have any words of wisdom for the young ladies of ChiTech?
When I worked in corporate America, I quickly realized that the most threatening person isn’t the one who is smarter than you; it’s the one who will work harder than you. So, always demand more than your parents, your teachers, and your mentors demand of you. Work ethic is the ultimate key to success.

About Cayla Weisberg:

Cayla Weisberg is partner at InvestHER Ventures, a Chicago based venture capital fund that invests in female entrepreneurs with early stage technology companies.

She is focused on investing in software enabled business services, data driven products, and disruptive solutions for large markets. With a track record for driving revenue for both fortune 500 and start-up companies, Cayla brings a strong sales focus to the InvestHER’s growing portfolio of scaling businesses.

Learn more about sponsoring a table for your company at the 3rd Annual Little Black Dress Night by contacting Kelly Jones, Executive Director, at 

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