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

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

Guest Bio:

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.

Host Bio:

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.

To see a list of Sharon’s clients, please visit LeadingLarge.com.

Resources or websites mentioned in this episode:

Mirasee
Sharon’s website: LeadingLarge.com
Small Business CFO’s website: www.SBCFO.com
Jonathan’s LinkedIn: LinkedIn.com/in/sbcfo
E-Myth Revisited (book): MichaeleGerberCompanies.com/product/the-e-myth-revisited

Credits:

Host: Sharon Richmond
Producer and Editor: Andrew Chapman
Executive Producer: Danny Iny
Music Soundscape: Chad Michael Snavely
Making our hosts sound great: Home Brew Audio

Music credits:

Track Title: Escaping Light
Artist: Aaron Sprinkle
Writer: Aaron Sprinkle
Publisher: A SOUNDSTRIPE PRODUCTION

Track Title: Bright Future
Artist: Be Still The Earth
Writer: Marshall Usinger
Publisher: A SOUNDSTRIPE PRODUCTION

Track Title: Coo Coos
Artist: Dresden, The Flamingo
Writer: Matthew Wigton
Publisher: A SOUNDSTRIPE PRODUCTION

Track Title: Grace
Artist Name: Shimmer
Writer Name: Matthew Wigton
Publisher Name: BOSS SOUNDSTRIPE PRODUCTIONS

Special effects credits:

24990513_birds-chirping_by_promission used with permission of the author and under license by AudioJungle/Envato Market.

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Episode transcript: Scaling Leadership from Solo to Team: Lessons for Small Businesses (Jonathan Ankney) coming soon.

Creators and Guests

Host

Sharon Richmond

Producer

Andrew Chapman

Editor

Andrew Chapman

Guest

Jonathan Ankney

Founder and CEO of Small Business CFO

What is To Lead Is Human?

In this podcast, executive coach Sharon Richmond interviews successful leaders who have applied their professional and personal growth to produce tangible business outcomes. They discuss challenges, lessons learned, and what has helped them guide their organizations to success. Sharon helps listeners supercharge their own leadership with coaching tips on how to apply the lessons learned from our guests.