I still very clearly remember my first years living in New York City. I had moved to NYC a few years after getting my BFA in Fine Arts and Art History from the School of the Art Institute of Chicago. I was heading to the city to get my MFA from the School of Visual Arts, and I had $3,000 to my name.

During my MFA years—and for several years after—I was committed to making a go of it, being a working artist in New York City. And for all of you creatives out there, this will probably sound familiar: I was betting on myself with limited resources—but unlimited determination.

It’s those early days—of first understanding my own cash flow and then years later, helping other creative entrepreneurs do the same in the early days of Creative Business, Inc.—that showed me the incredible potential for creative businesses to scale.

In this month’s newsletter, we’ll explore the unique financial journey of creative enterprises: from scaling your financial operations, to the key strategic investments that mark exponential growth, to the specialized financial infrastructure that established creative businesses need to thrive at scale. Because we all know: Building a significant creative enterprise requires a balanced approach to financial management, one that supports your creative vision while driving revenue growth.

Understanding your finances (as your business grows)

When I first started working with creative businesses, I discovered that financial management doesn’t have to be complicated to be effective. While there are plenty of automated tools out there to help, one of my best pieces of advice is to find the right approach for your current business stage, rather than trying to adapt something before you’re ready.

For newer businesses, simple systems work well—like the accordion files divided by month that I used to recommend to clients starting out. As your business grows, your financial approach can shift right along with it, so don’t be afraid to simply start where you are. As their businesses have progressed, many of our established clients have moved beyond basic tracking to implementing more robust systems—working with dedicated bookkeepers and financial advisors or even bringing these roles in-house as their operations expand.

The key is creating scalable routines that align with your business operations and creative processes. Whether you’re reviewing finances monthly with your team or meeting quarterly with financial advisors, successful creative businesses establish financial protocols that complement their production cycles and strategic planning.

The evolution of a creative business

Drawing from my years helping creatives build sustainable businesses, I’ve observed that the transition from “creative” to “creative entrepreneur” involves more than just financial shifts. It requires a fundamental evolution in how you think about your work.

In Creative Business’s early years, I noticed a pattern: Many talented creatives struggled not because of an inability to scale their ideas, but because they hadn’t yet developed the business infrastructure to support their vision. Here’s what I’ve learned about making this crucial transition:

• Start with systems: Begin with basic financial organization—those accordion files I mentioned earlier are just the start. Set regular days for reviewing finances and paying bills. This creates the foundation for more sophisticated financial management as you grow.
• Recognize your brilliance AND your blind spots: Identify your specific financial pain points. Is it tax compliance for your international clients? Managing payroll for your growing team? Understanding insurance requirements across multiple projects? Once identified, build dedicated systems or bring in specialized talent to address these specific areas—allowing you to focus on your creative brilliance while ensuring your financial foundation supports your global ambitions.
• Diversify Your Revenue: The most resilient creative businesses I work with have multiple income streams. An artist might combine original works, limited editions, and teaching. A design house or creative agency might balance client projects with the launch of a complimentary product or service. Think of it as creating financial stability through creative variety.
• Build Your Financial Literacy: Understanding cash flow, profit margins, and basic financial forecasting isn’t just about numbers. It’s about giving yourself the tools to make informed decisions about your creative future. Start small, but start somewhere.
• Invest in Growth: Successful creative entrepreneurs understand that investing in their business—whether through professional development, marketing, or building a support team—is essential for sustainable growth.
• Remember the Tax Reality: I often see creative entrepreneurs caught off guard by tax obligations. Set aside a percentage of your income (I recommend at least 30%) for taxes from day one, and commit to paying your quarterly taxes. Think of it as a cost of doing business—and work with tax and accounting professionals who can proactively help you stay on track.

Building this kind of financial infrastructure doesn’t mean compromising your creative vision—it’s the foundation that will allow your vision to truly be realized. Start with the basics, and build from there.

Do creative businesses need specialized financial support? Yes.

When someone suggests creative businesses can get by with generalist financial services, I think about the architecture firm that just told us they need to finance a project spanning three years. Or the gallery owner wrestling with seasonal cash flow. Or the design studio balancing client projects with product development. Each of these scenarios requires financial guidance that goes beyond standard accounting practices.

At Creative Business, Inc., our work across the creative spectrum gives us a unique vantage point. What we learn from helping a successful illustrator diversify their revenue streams might inform how we guide a photography studio through similar challenges. The insights we gain from helping an architectural firm manage long-term project financing could help a design agency structure its own extended engagements.

This cross-pollination of knowledge is so meaningful. When you work with industry-specific advisors, you’re not just getting someone who understands debits and credits—you’re accessing a knowledge base built from hundreds of creative businesses facing similar challenges:

• Understanding how to structure contracts for creative work
• Managing the complexities of project-based revenue
• Navigating industry-specific insurance and legal requirements
• Identifying growth patterns typical in creative businesses
• Recognizing when to scale and how to do it sustainably

I often hear from clients who previously worked with generalist firms about the frustration of having to explain basic industry concepts or justify common creative business practices.

The right financial partner should already understand your business model and be able to provide insights based on real experience with similar creative enterprises. They should know, for instance, that a creative business hitting $250K in revenue faces different challenges than a retail business at the same revenue level, or that creative businesses often need to reinvent their service offerings every few years to stay competitive.

This specialized knowledge becomes particularly crucial during major transitions. Hiring key team members, expanding services, or adapting to market changes. Having a financial partner who’s guided other creative businesses through similar transitions can mean the difference between growth and stagnation.