KauffmanWomen: Q&A with Gale Wilkinson

This month, we interviewed early-stage investor Gale Wilkinson. Gale is the founder and managing partner of Vitalize, a seed fund and angel community investing in the future of work software. Previously, Gale founded IrishAngels, one of the largest angel groups in the country. Gale has deployed over $65 million in capital across 80 early-stage companies. She has also made over 25 personal angel investments.

Her experience prior to venture capital includes founding two startups, consulting for new product launches with Nielsen, and guiding strategy with Orbitz. She was a founding board member of C200 Scholars Network and is currently a founding board member of Chicago Blend, an organization focused on increasing diversity in venture capital and startups. She received her BBA with honors from the University of Notre Dame du Lac and MBA with honors from the University of Chicago.

In this interview, Gale shares her work in early-stage investing, thoughts on opportunities for LPs, and women leaders who inspire her.

What inspired you to start the venture fund Vitalize, and then the angel group Vitalize Angels?

I have been investing in VC deals since 2013, first as the founder of IrishAngels, and for the last three years as GP at Vitalize. I was inspired to build a career in VC so that I can help founders at the very early stage. I am an entrepreneur, a problem solver, and a coach by nature. As such, VC is a perfect fit. Vitalize has a seed-stage fund and an angel community, both investing in early future of work deals.

Vitalize Angels is an “angel group for everyone.” I think early-stage VC is changing; as part of that, founders are asking for more diversity on their cap tables. It’s really difficult for legacy firms to change the face of their teams overnight which is one of the reasons we still only see a small percentage of women and people of color in VC partner roles. We wanted to remove these barriers to access and create a way for literally everyone in the world to be able to learn how to invest in VC deals. Our community launched a few months ago and has over 300 angels, 70% of whom are under-represented. Our angels have access to educational content, guest speakers from the VC world, and robust due diligence packets for all companies in which we consider investing. We have also rolled out a program that allows our angels to learn how to conduct due diligence first-hand, with 25 of our angels enrolled already. Becoming a good angel investor or VC requires at-bats — our community is a low-pressure way for people to get the reps they need to build confidence that they can in fact be good investors. Success to us is helping thousands of people become angel investors, with many of them going on to become GPs or LPs.

What message do you have for LPs investing in new funds?

I applaud all of the LPs out there who are deploying their capital with emerging managers, and I am confident these LPs will be rewarded financially. Data shows that funds 1,2 and 3 tend to out-perform, and smaller funds tend to outperform because the outcomes don’t have to be quite as high to still yield strong returns. Emerging managers are scrappy, they think differently, and founders want to work with them. Once again, VC is changing rapidly, and I think emerging managers fill a huge white space we’ve had in the industry at the earliest stages.

I think there is a huge opportunity for an LP that has access to billions of dollars to build a firm dedicated exclusively to small VC funds. If I weren’t building Vitalize and Vitalize Angels, I would seriously consider innovating in the LP world, as a data science approach to invest $1–10M into hundreds of small and emerging VC funds makes so much sense to me based on what I see happening in the industry.

What is the best advice you’ve received from an entrepreneur?

My mentor John Evarts is an entrepreneur who has given me so much advice over the years. Through all of it rings the truth of staying authentic to myself and not letting anything (or anyone) hold me down. I am forever grateful to him and the many others who have helped me on my journey.

If you could immediately gain one skill, what would it be?

While it doesn’t have anything to do with VC, I wish I were a better singer!

What woman leader inspires you the most?

I’ll share some of my favorite women leaders in VC who inspire me often: Kate Mitchell, Aileen Lee, Arlan Hamilton, Elizabeth Yin, Lolita Taub, Paige Doherty, Noramay Cadena, Shila Nieves Burney, and so many more!!

How have you leveraged the KF network, or what have you enjoyed most about the program?

I am extremely grateful to the Kauffman Fellows team and program for bringing together a fabulous group of VCs. I have made lifelong friends, co-invested in deals, and learned a lot about what works and doesn’t work in venture. Most importantly, Kauffman Fellows are always open to provide help and support to one another. Just today, I spoke with a Kauffman Fellow in another class who responded to a cold email I sent, and we had an interesting conversation about the future of venture capital. I recommend the program to other GPs quite often!

KauffmanWomen features insights from women investors, entrepreneurs, and executives within the Kauffman Fellows network. The series is edited by Ernestine Fu (Class 17) and Jessica Straus (Class 22), co-chairs of the Kauffman Women’s Group. Have ideas for future articles? Submit your ideas here.