Scaling Leadership from Solo to Team: Lessons for Small Businesses (Jonathan Ankney)

Episode # 56

Jun 25, 2025

Blending creativity and finance, Jonathan Ankney went from solo entrepreneur to leading a small business by blending grace, accountability, and faith-based principles. He explores leadership challenges and scaling with purpose—offering insights for small business owners and nonprofit leaders alike.

This is To Lead Is Human — listen to learn how you can uplevel your leadership and shape cultures of accountability, respect, and candor.

“ Every year my job description changes. ”

Jonathan Ankney
Jonathan Ankney

Jonathan Ankney is the Founder and CEO of Small Business CFO, Inc., a financial consulting firm dedicated to helping small businesses and nonprofit organizations build financially resilient operations. Since 2004, Jonathan has led his team of eight in delivering CFO-level insights, accounting systems design, forecasting, and financial strategy to organizations with revenues up to $8 million. His clients—ranging from creative firms and tech startups to nonprofits—rely on his ability to translate complex financial data into practical, forward-looking decisions that drive growth and stability.

With a background in both finance and arts administration, Jonathan combines technical expertise with strategic vision. He’s personally managed more than 100 client engagements, supporting capital planning, business modeling, cash flow optimization, and financial clean-up projects. His team also specializes in managing clients’ books, multi-entity reporting, payroll, and review of financial records. A problem-solver at heart, Jonathan is known for stepping into high-stakes situations—such as audit preparations and turnaround scenarios—and bringing clarity and structure to the financial side of the business.

Jonathan holds an MBA in Finance from Binghamton University and is a sought-after speaker and educator on small business finance. His work has been featured in podcasts, webinars, and conferences, and he authored Freedom to Serve, a financial guidebook for ministry leaders. When he’s not advising clients or building systems, Jonathan is an endurance cyclist, active church leader, and Distinguished Toastmaster, passionate about helping others communicate their vision and stay financially focused.

Sharon Richmond

For more than 30 years, Sharon Richmond has partnered with C-level executives from mid-size and small, fast-growing companies who want to up-level their leadership and build companies they are proud of. Clients accelerate their leadership by embracing mindset and behavior changes, building self-awareness and self-management skills, and focusing on the three things all leaders must ensure: focus, energy, and delivery.

Sharon’s purpose as an executive coach is to help leaders 10X their impact by leveraging the power afforded by their roles to build organizations that are forces for good, both economically and socially. She also advises CEOs on shaping organization culture and leading change.

Sharon has taught leadership at Stanford GSB, where she now helps leaders increase influence, manage conflict, and prepare to build high-performing teams.

Resources or websites mentioned in this episode:

Credits:

  • Guest: Jonathan Ankney
  • Host: Sharon Richmond
  • Producer and Editor: Andrew Chapman
  • Executive producer: Danny Iny
  • Music soundscape: Chad Michael Snavely
  • Making our host sound great: Home Brew Audio

Music and SFX credits:

Every business leader has a huge impact on their organization. In this podcast, Sharon Richmond interviews successful leaders who have turned personal growth into tangible business outcomes. They discuss overcoming challenges, lessons learned and what helps them make a positive impact in their organization. Sharon offers insight and advice to help listeners envision how they can supercharge their own leadership by blending the art and science of leading with intention.

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