Katherine Fry
Katherine (Katie) Fry is a business advisor and entrepreneur based in Richmond, Virginia, who has built a career around creativity, entrepreneurship, and leadership transforming her early experience in scenic design into a successful business and, later, a mission-driven career helping other entrepreneurs grow. She currently serves as a Business Advisor at Cultivate Advisors, where she partners with small business owners to develop practical strategies that drive sustainable growth, strengthen teams, and increase enterprise value. Katherine specializes in client management, team development, and what she calls “soft infrastructure”—the intersection of emotional intelligence and business ownership helping leaders navigate complex business challenges while building resilient organizations.
Katherine began her career in a completely different world, studying theatrical scenic design for live events at Virginia Commonwealth University before moving to New York City to pursue freelance work as a designer and scenic artist. As her freelance career expanded, she identified a gap in the live events industry for scenic art-focused work, including creating thematic art for productions such as Broadway backdrops and installations for cultural institutions like the Minneapolis Institute of Art and MoMA. She later co-founded Infinite Scenic LLC with a business partner, eventually buying out her partner and growing the company independently. With an all-female management team and no outside investors or funding, Katherine bootstrapped Infinite Scenic into a seven-figure business within three years, growing to a full-time staff of eight and a freelance network of more than 100 creatives while serving clients ranging from small nonprofits to major organizations such as the Public Art Fund.
After successfully guiding the company through the COVID-19 pandemic and executing a strategic exit, Katherine transitioned into business advising to help other entrepreneurs avoid the operational and strategic challenges she had to learn through experience. She was drawn to Cultivate Advisors because of its mission-driven approach and the fact that all advisors are former business owners who bring real-world experience to their clients. Today, Katherine focuses on helping business owners strengthen operations, develop high-performing teams, and build the emotional and strategic foundations necessary for long-term success, combining her creative background, business acumen, and passion for empowering entrepreneurs.
• Emergency First Response Primary Care (CPR)
• Certificate of Fitness for Flame Retardant Treatment (C-15)
• Virginia Commonwealth University - BFA, Theatreical Scene Design
What do you attribute your success to?
I attribute my success to hard work, persistent networking, and the discipline of building and scaling a business through bootstrapping without outside funding. I’ve learned valuable lessons by doing things the hard way through hands-on experience, while prioritizing strong team building and leadership particularly through developing and working alongside an all-female management team. These experiences shaped my ability to solve problems strategically, stay resilient through challenges, and grow organizations from the ground up.
What are the biggest challenges or opportunities in your field right now?
I think it could be a challenge, but it's too soon to say - I'm very interested to see how AI is going to impact really every aspect of our society. Ironically, my husband is an AI developer, so we have lots of debates in the household about ethics and application. I'm interested to see how much we're going to embrace AI, what pitfalls we're going to find from that, and then how we are, as a society, going to adapt once we identify the pitfalls. I think the applications are so vast, which is really cool and exciting, but for the most part, it's probably just going to simplify parts of life. But there are other things where, when it starts to replace different parts of learning or human interaction, how is society going to rebound from that? How much damage is going to get done to society before we identify that it's a problem? More tangibly, I think as much as I've already been doing this for a couple years, I do still feel like I am transitioning, and I'm not sure that feeling will ever go away. I've been thinking a lot about this - many of us, especially with the pandemic, pivoted or transitioned or decided to make a big life change, and when does it ever become normal? I'm not sure it does.
What values are most important to you in your work and personal life?
The values most important to me in both my work and personal life include helping individual business owners thrive, fostering autonomy and independence for entrepreneurs, and emphasizing emotional intelligence in leadership. I’m also deeply committed to supporting team growth, creating environments where people can succeed, and protecting individuals’ time so they can focus on what matters most.