Are You Gambling with Your Business Finances?

From Poker to Profit: How Stephanie Gillenkirk Helps Small Businesses Win with Their Finances

Welcome back to I Know A Guy. Today, we meet Stephanie Gillenkirk, founder of Pittroe and a powerhouse financial expert who helps small businesses,s especially in construction and service-based industries, turn financial chaos into clarity.

🎙 Meet Stephanie Gillenkirk

From poker tables to balance sheets, Stephanie has had a unique journey into entrepreneurship. After years of working in the casino industry as a dealer, she pivoted back to her accounting roots when she saw just how many business owners were gambling with their finances without even realizing it. Today, she’s a fractional CFO and strategic partner for small businesses looking to grow without guessing.

💡 What She Does

Stephanie provides full-spectrum financial services, from basic bookkeeping to high-level financial strategy. She’s especially passionate about working with contractors and tradespeople, helping them raise their prices with confidence, clean up their books, and take control of their cash flow. Her no-jerk policy ensures she only works with values-aligned clients who are ready to make smart moves.

🚧 Pain Points She Solves

If you’re a business owner drowning in receipts, struggling to send clean invoices, or just wondering where your money went, Stephanie is your person. She helps you:

• Separate business and personal finances (for real).

• Clean up chaotic books.

• Implement simple tech tools that make invoicing, mileage tracking, and payment processing a breeze.

• Understand key financial reports like P&L and balance sheets in plain English.

• Stop guessing and start making data-informed decisions.

🔗 Ideal Collaborators

Stephanie collaborates well with:

• HR providers & payroll specialists

• Business attorneys

• PEOs

• Other B2B service providers who serve growing companies

🎯 Advice for Aspiring Entrepreneurs

“Separate your mindset and your money early,” she says. Stephanie encourages new business owners to adopt the CEO mentality from day one and protect their personal assets by keeping clean financial records. That one shift could save you in more ways than you realize.

📈 How She Helps You Grow

Through her financial playbook (yes, she ties it into sports analogies!), Stephanie breaks down financial statements into easy-to-understand tools you can use to drive your business forward. With strategic bookkeeping and consistent reporting, you stop reacting and start planning, whether it’s for tax season, hiring decisions, or growth.

📬 Connect with Stephanie Gillenkirk

• 🌐 Website: www.pittroe.com

• 📧 Email: [email protected]

• 💼 LinkedIn: linkedin.com/in/sgillenkirk

• 📘 Facebook: facebook.com/pittroe

Watch The Full Interview Here