“Encourage Girls to Think Big” with Madeline Keulen of Victress Capital

As part of my series about “the five things we need to do to close the VC gender gap” I had the pleasure of interviewing Madeline Keulen. Madeline is an investor at Victress Capital where she focuses on identifying game changing startups led by diverse teams. Madeline frequently speaks to groups of entrepreneurs and investors on topics ranging from investment strategy to professional development and is an active member of women in venture / tech groups including All Raise and Declare. Prior to venture capital, Madeline worked in management consulting. She holds an MBA from Harvard Business School.

Thank you so much for joining us! Can you tell us the “backstory” that brought you to this career path?

After years advising Fortune 500 companies on how to compete amidst innovative market entrants, I became engrossed in following the growth trajectories of emerging technology companies. As friends began founding and joining early stage startups, I found myself wanting to learn as much as possible about why, what, and how their firms were disrupting markets.

Prior to starting business school I reconnected with a man I look up to who is a successful venture capitalist in Austin and began learning more about venture through working with him as I started my MBA. I met the two founding GPs at Victress through a professor during my first semester at HBS. I loved their mission, was impressed by what they had built as angel investors and was thrilled for the opportunity to help build Victress’ capabilities as a venture firm working part-time during school and full-time upon graduating with my MBA.

Venture is a terrific career path for those interested in both the macro picture of what the future holds as well as the intricate details of individual business models and approaches. It’s also a tremendously rewarding role in terms of the amount of impact you’re able to drive.

Can you share a story of your most successful Angel or VC investment? In your opinion, what was its main lesson?

Victress recently invested in WaitWhat’s series A round. As a self-proclaimed podcast junkie and an avid listener of “Masters of Scale” I found the opportunity to invest in the burgeoning podcast industry to be exciting. As early stage investors it’s our task to look beyond where companies and entire industries are today and imagine how the future will unfold. I’ve learned that having conviction amongst uncertainty is key.

Can you share a story of an Angel or VC funding “failure” of yours? Is there a lesson or take away that you took out of that that our readers can learn from?

We’ve passed on a few deals that could have potentially returned the fund. While it’s difficult to let go of these misses, it’s valuable to lean into them in order to fully understand what went wrong and how you can avoid making the same type of mistake in the future.

Was there a company that you turned down, but now regret? Can you share the story? What lesson did you learn from that?

We passed on Lola at the seed stage which has since grown to be a phenomenal force, continuing to attract customers, capital, and talent. We were busy chasing other deals at the time and failed to see how big the opportunity could become. Focus is extremely important for both investors and entrepreneurs and knowing when to re-direct can be tough.

Ok let’s jump to the main focus of our interview. According to this article in Fortune, only 2.2% of VC dollars went to women in 2018. Can you share with our readers what your firm is doing to help close the VC gender gap?

Victress Capital invests solely in diverse teams. It’s both an investment strategy that has proven itself through our fund’s returns and a mandate we believe is important to make a change in the industry. There is a tremendous amount of opportunity in this space and we’re excited to be part of capitalizing on it.

Can you recommend 5 things that need to be done on a broader societal level to close the VC gender gap.

1. Encourage girls to think big
   - From the time girls are young, we must encourage and support them to be whoever they wish to be, unconfined by gender stereotypes. We need young women to see themselves as builders and entrepreneurs in the same way young men are encouraged to.
2. Create the infrastructure for women and men to thrive in the workplace
   - Policies need to reflect the needs of a diverse workforce. Individuals and families require flexible arrangements in order to thrive. Both men and women should have the ability to take care of themselves and their loved ones while also succeeding at work.
3. Be open to mentoring those who are different
   - Women need to mentor young men just as men need to mentor young women. We need to create environments to learn from and find commonalities with people who may at first seem different.
4. Don’t quit
   - Don’t give up — even when things are hard. Seek support. Seek change.
5. Be part of the solution
   - It’s both easy to complain and to make others’ lives more difficult even without meaning to. Find ways to build empathy and be supportive to those who need it. Find ways at a micro or macro level to make a difference.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. :-)

I’d love to see personal finance being taught to children and young adults. My journey into learning about personal finances began the hard way — I cashed out my first 401k plan when leaving Apple not knowing what else to do. Since that point I’ve taken it upon myself to study up and manage my investment strategy more closely. We need to de-stigmatize investing as something that is inaccessible or scary and empower people from a young age to take charge of their financial future.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

Carpe diem. I know it’s cheesy, but the phrase is as meaningful to me today as it was back when I was a bubbly nerd of a teenager scribbling it on my notepads. To me it’s a reminder to be thankful for what we have each and every day and to take advantage of each and every opportunity.

Some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US whom you would love to have a private breakfast or lunch with, and why? He or she might see this, especially if we tag them. :-)

I’d love to share a meal with Kirsten Green. Kirsten is an iconic investor and well known to be a highly valued board member and advisor to the companies she backs. I also admire that she breaks the mold in that she’s a successful VC who is not from a founder/operator background.

This was really meaningful! Thank you so much for your time.