Navigating Your Numbers: From Stressing to Strategizing

Managing your business finances can feel stressful—but it doesn’t have to stay that way.

Too often, founders are juggling everything—customers, operations, growth—and the financial side of things ends up being reactive instead of strategic. It’s not that they’re doing anything wrong, it’s just that most early-stage entrepreneurs aren’t handed a playbook for how to manage their numbers with clarity or confidence. Understanding your finances isn’t just about bookkeeping—it’s about making decisions, spotting patterns, and building a business that can grow sustainably. In our latest founder workshop, Navigating Your Numbers, we teamed up with experts across the financial world to help entrepreneurs build a more confident, informed relationship with their finances.

Money Management Basics

One of the biggest mindset shifts entrepreneurs can make is realizing that managing your finances doesn’t require perfection, just a willingness to build habits that make the process feel more approachable over time.

A good starting point?

It sounds simple, but opening a dedicated business bank account early, even before you feel “ready," can lay the foundation for clearer tracking, smarter decisions, and a lot less stress come tax season. From there, choosing tools and systems that fit you makes a huge difference. Whether it’s a spreadsheet, a free accounting platform, or even a recurring calendar reminder, consistency matters more than complexity. When founders use tools they actually enjoy, or at least don’t dread, they’re far more likely to stick with them and gain real clarity over time.

Just as important is building in time to check in. Spending even 15 minutes a week reviewing your numbers can go a long way toward understanding your cash flow, catching issues early, and feeling more in control. It’s not about becoming a financial expert overnight—it’s about making small, intentional moves that build confidence as you grow.

Planning What's Next

As your business grows, your financial needs—and the questions you’re asking—start to shift. Early on, it’s about staying afloat and making sure you can cover expenses. But as things begin to stabilize, your focus naturally turns to what’s ahead: How do I plan for the future? What decisions should I be making now to support where I want to go? One of the biggest shifts founders can make is moving from reacting to planning. That’s especially true when it comes to taxes. Instead of waiting until tax season to sort everything out, building in checkpoints throughout the year can help reduce surprises and make things far less stressful. Using a tool to collect receipt snapshots, setting aside funds regularly, understanding your tax obligations, and—if possible—checking in with a CPA periodically can go a long way toward helping you stay compliant and confident.

Another helpful approach is creating a 12-month rolling outlook. Rather than only focusing on this month or next, zoom out and think about where you want the business to be a year from now. Then work backwards. What needs to happen six months from now to support that vision? What should you focus on this quarter to stay on track?  Turn your numbers into a roadmap—so every decision you make today supports where you want to be tomorrow.

Financial Decisions That Position You For Growth

As your business gains traction, it’s easy to get caught up in the day-to-day—but the decisions you make during these growth stages can have a lasting impact. From how your business is structured to how you protect your assets and plan for future opportunities, laying the right foundation matters.

Structure Matters.

One of the most overlooked areas for early-stage founders is legal and operational planning. Choosing the right business structure (LLC, S-Corp, etc.), isn’t just a formality. It affects everything from how you're taxed to your ability to raise capital or bring on partners down the line. And while it might feel premature to think about those things early on, setting your business up the right way now can prevent unnecessary costs and headaches later.

Ask for help early on.

Founders often wait until something goes wrong to seek out legal or financial advice, but by then, the damage is done. Whether it’s reviewing contracts, checking for compliance, or making sure your systems are set up correctly, reaching out early can help you avoid common pitfalls—and make better decisions along the way.

Plan like a CEO

Thinking like a CEO means making decisions not just for where your business is today, but for where you want it to go. That could mean budgeting for your next hire, reviewing your operational systems, protecting your intellectual property, or preparing to seek funding. Strategic planning is part of positioning yourself to grow on purpose, not by accident.

Financial confidence doesn’t come from having all the answers—it comes from building habits that help you make informed decisions as you grow. Even something as simple as a

monthly check-in can help you track what matters, reflect on your progress, and use your numbers to guide your next move. With the right foundation, your numbers can become one of your most powerful tools.

About the Panelists:

Laura Lee has been in banking for 12 years, with 8 of those years at BMO Bank. BMO's slogan is, "Boldly grow the good, in business and in life", and Laura strives to live that out each day! She has a passion for making banking simple and helping people reach their financial goals.

Lindsey Barbour is an experienced CFO and Tax Strategy Consultant, specializing in working with entrepreneurs. With nearly 20 years of CFO, consulting, entrepreneurial and teaching experience, Lindsey's true passion is investing in others: her family, her community, and emerging CCK Strategy professionals, to help them develop their niche and grow in knowledge.

Brittany Littleton owns and operates Littleton Legal. Her practice focuses on business law, estate planning, and probate and trust administration. An active participant in the local entrepreneurial community, Brittany is passionate about helping Oklahoma businesses prosper. Her extensive experience as a former In-House Counsel and Chief Operating Officer for multi-million-dollar businesses gives her a unique perspective when acting as outside general counsel services for local companies. 

Monthly Check-in Guide:

Business Finance Worksheet.

Download • 63KB