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July 22, 2025 55 mins
In this episode of Disciplined Troublemakers, host Scott Shagory sits down with Pam Prior, a CFO and financial coach with over 30 years of experience. Pam has guided a diverse range of clients, including bootstrapped entrepreneurs, private equity investors, Fortune 500 companies, social media influencers, and professional athletes through the complexities of business finances.

Scott and Pam discuss how tech CEOs, whether bootstrapped or funded, can refine their financial storytelling and address challenges that arise from overlooked financials. Pam shares practical advice on establishing reliable bookkeeping practices, balancing growth with profitability, developing effective pricing models, and determining the right time to bring in a CFO or restructure the team.

For those experiencing uncertainty in their business finances or seeking to implement processes that support sustainable growth, this conversation offers valuable insights and actionable strategies. Learn how to achieve financial clarity and make informed decisions that drive your business forward.

Pam Prior is the owner of a bookkeeping and fractional CFO company, a two-time bestselling author, and the host of the Cash Flow and She Said, She Said podcasts. Known as the "Finance Friend in a Foxhole," she is dedicated to supporting 21st-century entrepreneurs.

Chapters:

00:00 – Introduction
01:03 – "Numbers Reveal Business Story"
05:26 – Financial Literacy: Key to Business Success
09:15 – Early Stage Business Strategy
10:55 – Diversify Investments, Understand Cash Flow
16:11 – Pricing Strategy for Niche Coaching
18:58 – Value over Price
20:02 – "Charging Difficult Clients More"
26:23 – Scaling Beyond Founder Limits
28:29 – Scaling Challenges and Leadership Transition
33:15 – "Importance of Client Contracts"
34:12 – Founder to CEO: Prioritize Roles
38:27 – Family Dynamics in Business Hierarchies
43:04 – Evolving Documentation Practices
45:35 – "When to Hire a CFO"
49:04 – CFO Role in Business Strategy
51:01 – Embracing Entrepreneurial Agility
54:34 – Interview with Pam on YouTube
54:55 – Outro

Quotes:

"Seeing your numbers as your business story clears the fog of uncertainty. That clarity brings true freedom."- Pam Prior

"When uncertainty lifts, clarity and perspective bring confidence and limitless growth."- Scott Shagory

Key Takeaways:

Financials Are Your Business Story, Not Just Numbers
Clean Books Are Cheaper (and Less Stressful) than Cleanups
Lift the Fog: Clarity Equals Confidence
For Bootstrappers: Profit, Scale, and Personal Goals Must Be Balanced
Scaling from $1M to $5M Means Reinventing Processes—and Yourself
Process = Freedom, Not Handcuffs
A CFO Is Your Foxhole Ally, Not Just a Number Cruncher

Connect with Pam Prior

LinkedIn: https://www.linkedin.com/in/pamsprior
Website: https://pamprior.com/

Connect with the Host Scott Shagory:

http://purplefinchgroup.com
http://linkedin.com/in/scottshagory
Email: mailto:scott@purplefinchgroup.com

Sponsor: Purple Flinch Group
https://www.purplefinchgroup.com/

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