Spotlight: Empowering Entrepreneurs with HPA's Bess Goodfellow

Bess is passionate about empowering founders as they build transformative companies. As a Principal, Bess is tasked with sourcing high growth companies across the Midwest and supporting those investments through their lifecycle. Her portfolio of investments spans a broad spectrum of industry including enterprise, fintech, consumer, and digital health. Bess joined HPA in 2017 as an Analyst. Prior to HPA, Bess graduated from the University of Chicago with degrees in Economics and Sociology.

1. Tell us more about your career journey and how HPA has supported your evolution from Intern to Principal. 

I’ve had a unique journey of starting at a venture firm after college and progressing from intern to Principal. Initially, I joined HPA as an intern and used my technical experience to apply different analytics to companies the firm was evaluating. After joining HPA full time as an Analyst, I learned a lot about making investments and became interested in how technology is applied when building businesses. As I became more plugged into VC and HPA’s portfolio, I realized that I enjoy working with founders and supporting them in their entrepreneurial journey. My promotion to Associate enabled me to meet with a high volume of entrepreneurs, which helped me learn how to identify and better articulate why a company is a fit for our investment or not. The development of these skills enabled me to handle the responsibilities I have today as a Principal: investing in high growth companies and supporting them to a successful exit. 

You’re always learning in VC – industries evolve, innovations emerge, and new challenges are presented. After a few years, I knew I wanted to become Principal so that I could work directly with founders as they transform industries. HPA has uniquely provided me with mentorship from our Members, the ability to invest in top Midwestern companies, and hands-on experiences helping entrepreneurs. I’m grateful that I’ve been able to develop these skills all under one roof. 

2. Your career has continued to progress while at HPA. What drives you as you work with entrepreneurs? 

I love being on the investor side because I am passionate about supporting founders on their journey to build something. I am motivated by helping to provide resources, financial capital, connections, and advice to see the founder succeed. My own expertise is complemented by the HPA ecosystem driven by our Members and Partners, consisting of domain experts across industries, who I’ve seen deliver immense value to our portfolio companies from day one. As a female investor, I can help advocate for other women and POC as I evaluate and source companies for funding. I’m proud to say that half of the investments I’ve led at HPA have women or POC founders.

Startup founders are transforming their industries through the problems they solve, benefits they provide customers, and employees they support. As investors, we are privileged to watch this industry disruption from the inside and HPA has been early investors in many exciting companies. Two Chicago unicorns, ShipBob and FourKites, have transformed supply chain visibility and ecommerce fulfillment. Provi has emerged as a market leader in the B2B alcohol marketplace and NOCD is now the world’s leading provider of OCD treatment. Helping enable the positive impact these companies have on their employees, industries, and communities drives me as an investor. 

3. Talk about your role as an investor. What do you look for when evaluating a company? What has stood out to you about the entrepreneurs you’ve worked with over the years?

For early-stage investing, you look for predictors of long-term success during a company’s beginning stages. At HPA, we have the unique advantage of leveraging the perspectives of our Members, who are domain experts in innovative fields. For example, I have worked with Stuart Frankel, the co-founder of Chicago-based Narrative Science that sold to Salesforce, on a deal in enterprise software and worked with Caitlyn Truong, CEO and co-founder of Zengines and former MD at Accenture, on a deal about data orchestration. Utilizing the insights from these Members along with the strategies employed by other successful HPA companies allow me to make more informed investment decisions. 

There is a lot you learn during market cycles, and I’ve been fortunate to work with founders who have persevered and navigated uncertainty through turbulent times. I’ve found it helpful to be open-minded and listen to founder stories. Every founder has a different leadership style and a superpower that helps them drive success. As an investor in early-stage companies, you need to have conviction about the founders you’re backing and how they’re going to create long-term value for the company. However, there are many great ways to build businesses and, at the base level, you need to have trust in the founder. 

4. What mentors and organizations have supported you in your career? What advice would you give to someone exploring a career in VC and entrepreneurs trying to build relationships within the ecosystem?

The entire Membership at HPA has been extremely helpful, but especially the female Members I’ve worked closely with like Amanda Lannert, Ann Deters, and Susan Whiting. There are a variety of organizations and networks that provide meaningful support, including All Raise, Women in VC network, 1871, and Intermitten. As a part of working with other investors, I’ve also developed strong relationships within the ecosystem and with other female investors. There are women known for how they support female partners in venture, such as Karen Kerr, Dipa Mehta, Gale Wilkinson, and Samara Mejia Hernandez.

For those looking to build their network, I’d recommend attending events and meeting people within the ecosystem. Especially for founders, it is also a genuine and supportive community. Be willing to appropriately share about what you’re trying to build or what skills you want to develop. Chicago is a great VC ecosystem because it’s a tight-knit community filled with humble people who want to help. Organizations should want to help you develop and grow to become a stronger investor and/or founder.

5. How is HPA thinking about DEI efforts and how do you personally champion diverse founders?

HPA is committed to advancing DEI efforts across its portfolio, membership, and broader community. In the last ten years of investment, about half of HPA’s companies have a diverse founder. Within the membership, we are working with our Membership Chair to implement strategies to attract new female investors. And within the broader community, we are avid supporters of Chicago:Blend, World Business Chicago, GET:Cities, and others who are advancing equity within the Chicago tech ecosystem. 

As a Principal, I’ve personally seen the direct impact I can have as a female investor. Like I mentioned, half of the investments I’ve led had a women or POC founder. I’ve been able to support impressive founders in the HPA portfolio like Katlin Smith from Simple Mills, Coco Meers from Equilibria, and Jan Seale and Coabi Kastan from Out of Office. Broadly, I’m able to offer a different perspective to the HPA Team and I am privileged to be in the position to help HPA find the best companies that represent the greater population.