Human-Centered Family Business Succession Planning, with Andrea Carpenter, The Transition Strategists, and Jamie Reynolds, Reynolds CFO Services (Family Business Radio, Episode 65)
In this episode of Family Business Radio, host Anthony Chen welcomes Andrea Carpenter of The Transition Strategists and Jamie Reynolds of Reynolds CFO Services. Andrea shares her journey from UX design to becoming a transition specialist focused on the human side of family business and internal succession planning. Jamie discusses his pivot from a corporate career to launching a fractional CFO firm that supports small and mid-sized businesses. Together, they explore the challenges and strategies of family business transitions, emphasizing the importance of communication, values, and aligning personal passions with business roles. You will gain valuable advice on preparing for succession, maintaining brand equity, and ensuring that next-generation leaders are equipped and passionate about taking over the family enterprise.
Anthony concludes the show with comments on the value of communication and individual identity in family business succession.
Family Business Radio is underwritten and brought to you by Anthony Chen with Lighthouse Financial Network. The show is produced by John Ray and the North Fulton affiliate of Business RadioX®.
Key Takeaways from This Episode:
Andrea Carpenter, The Transition Strategists
- Start with Values Before Structures – True succession success starts with understanding personal goals, non-negotiables, and passions—not just business mechanics.
- Use Dialogue to Prevent Disconnection – Transparent conversations between generations prevent misaligned expectations and foster trust.
- Empower, Don’t Pressure, the Next Generation – Support younger family members in discovering their authentic path—whether inside or outside the family business.
Jamie Reynolds, Reynolds CFO Services
- Fractional CFOs Bring Strategic Clarity – Jamie helps small businesses make financial decisions with confidence, beyond bookkeeping or tax prep.
- Training Beats Replacing – Family members often have the heart, but need the tools. Jamie helps build their capability to lead.
- Work-Life Balance Is a Leadership Priority – After a heart attack, Jamie redefined success: being present with family while helping others grow.
Anthony Chen, Lighthouse Financial and Host, Family Business Radio
- Legacy Is More Than a Business – The real asset being transferred isn’t just ownership. It’s identity, values, and intent.
- Succession Is a Conversation, Not a Conclusion – Families must start talking, even before they feel “ready,” to explore what a good transition looks like.
- You Don’t Have to Become Them to Honor Them – Children don’t have to copy their parents’ careers to carry forward their values and legacy.
Topics Discussed in this Episode
00:00 Introduction to Family Business Radio
00:30 Andrea Carpenter’s Journey into Family Business
02:05 The Human Side of Family Business
12:38 Navigating Family Business Conflicts
26:15 Jamie Reynolds: Transitioning to Business 2.0
31:10 Believing in the Mission
31:38 Relaunching Reynolds CFO Services
32:55 Balancing Family and Business
33:04 Health Scare and Its Impact
33:43 The Flexibility of Business Ownership
37:04 Family Support and Early Return to Work
39:13 Client Success Stories
43:11 The Role of a Fractional CFO
46:57 Contact Information and Services
48:15 Words of Wisdom for Family Business Succession Planning
49:16 Legal Disclaimer and Closing Remarks
Andrea Carpenter, The Transition Strategists
As President of The Transition Strategists, Andrea Carpenter specializes in guiding multi-generational families through complex business succession planning. Her unique perspective as both a successor in her family business and an advisor to transitioning families offers priceless information about the challenges faced by both generations.
Andrea excels at creating psychologically safe environments where families can navigate the delicate balance between preserving legacy and embracing innovation. As a certified XChange facilitator, she combines human-centered design principles with proven facilitation techniques to help clients transform business transitions into opportunities for deeper family connection.
The Transition Strategists is an international boutique consultancy headquartered in Denver, Colorado, with over 30 years of experience in business succession planning and transition strategies. The firm works with family and private business owners, their companies, and their families. They design dynamic, people-first succession plans, balance business objectives with family relationships, and create transition paths that sustain business success and launch leaders into new ventures.
Andrea LinkedIn | Company Website
Jamie Reynolds, Reynolds CFO Services, LLC
Jamie Reynolds is the founder and owner of Reynolds CFO Services, LLC. As the principal of the firm, Jamie specializes in providing financial services to small and medium-sized businesses (SMBs), with a focus on financial planning and analysis (FP&A), bookkeeping, and grant writing
Reynolds CFO Services positions itself as a partner for business owners who need professional financial guidance but may not require a full-time, in-house CFO. The firm’s mission is to provide reliable, actionable financial insights and support, enabling clients to focus on running and growing their businesses. Reynolds CFO Services is renowned for its pragmatic approach and unwavering dedication to assisting clients in reaching their financial objectives.
Jamie LinkedIn | Company Website
Anthony Chen, Host of Family Business Radio
Family Business Radio is sponsored and brought to you by Anthony Chen with Lighthouse Financial Network. Securities and advisory services are offered through OSAIC, member FINRA/SIPC. RAA is separately owned, and other entities and/or marketing names, products, or services referenced here are independent of OSAIC. The main office address is 575 Broadhollow Rd., Melville, NY 11747. You can reach Anthony at 631-465-9090, ext. 5075, or by email at anthonychen@lfnllc.com.
Anthony Chen started his career in financial services with MetLife in Buffalo, NY, in 2008. Born and raised in Elmhurst, Queens, he considers himself a full-blooded New Yorker while now enjoying his Atlanta, GA, home. Specializing in family businesses and their owners, Anthony works to protect what is most important to them. From preserving to creating wealth, Anthony partners with CPAs and attorneys to help address all of the concerns and help clients achieve their goals. By using a combination of financial products ranging from life, disability, and long-term care insurance to many investment options through Royal Alliance, Anthony looks to be the eyes and ears for his client’s financial foundation. In his spare time, Anthony is an avid long-distance runner.
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