John Heflebower is a seasoned executive and strategic advisor with over four decades of experience guiding businesses through operational growth, succession planning, and strategic transitions. With a diverse background spanning the wine and spirits industry, cybersecurity, energy management, and food safety, John brings a unique multidisciplinary perspective to every leadership role he assumes.
Currently serving as the Founding Partner and Senior Business Consultant at JVH Business Solutions in St. Helena, California, John specializes in preparing mature businesses for successful exits and liquidity events. His approach is comprehensive—ensuring corporate documentation is audit-ready, cybersecurity and insurance measures are robust, and tax strategies are optimized for upcoming transitions. As a Certified Exit Planning Advisor (CEPA), John utilizes platforms like CAPITAIZ to analyze financial performance and drive value-creation strategies, empowering owners to increase business worth and readiness for sale.
John also holds the Certified Financial Planner (CFP) designation, which enhances his ability to provide deeply integrated business and personal financial advice. His financial expertise is further leveraged through his part-time role with Malcom Risk Advisors, where he advises on business analysis and strategic risk planning.
A former Senior Vice President at Merrill Lynch for over 33 years, John’s tenure there laid the foundation for his expertise in financial services, investment management, and corporate benefits strategy, including 401(k) plans and deferred compensation structures. Although now under a non-compete restriction from the financial sector, he continues to apply his knowledge to industries where strategic growth and operational alignment are paramount.
John is particularly interested in industries such as wine and spirits, landscaping, cybersecurity, food safety, and energy management—especially companies that are scaling beyond $100 million in annual revenue. He thrives in environments where businesses are on the cusp of transformative growth and need experienced guidance to navigate complexity and unlock new potential.
Beyond his technical acumen, John is a passionate communicator and mentor. He has served on college boards for more than a decade and has nonprofit board experience (namely in the areas of governance, budgeting and planned giving programs), underlining his commitment to organizational stewardship and educational development. John is also a founding board member with the Napa Valley Community Foundation and the UpValley Centers in the Napa Valley. While he has not been publicly quoted or engaged in speaking events due to previous restrictions, he is currently developing written thought leadership pieces and plans to launch a professional blog to share insights on strategy, operations, and transition planning.
A lifelong learner, John holds a credential in Business Strategy from Harvard Business School Online and earned his undergraduate degree from Ripon College, where he studied Liberal Arts with concentrations in Economics and Art History. He is fluent in English and conversational in Spanish, with international exposure in Central America.
John believes in staying mentally engaged and contributing his wealth of knowledge to help others think outside the box. His career—from corporate executive to startup advisor—reflects a consistent drive to solve problems, unlock value, and support sustainable growth. As he explores advisory and board opportunities, he offers a rare blend of strategic insight, operational experience, and financial acumen to organizations seeking to scale, transform, or transition.
Character: John is a principled and purpose-driven leader who values continuous learning and helping others succeed through thoughtful guidance and integrity.
Knowledge: With over 40 years of experience across financial planning, business operations, and exit strategy, John brings deep expertise in navigating complex business transitions.
Strategic: He excels at identifying growth opportunities and aligning organizational operations with long-term objectives, particularly for companies preparing for scale or sale.
Communication: John is a clear and empathetic communicator who effectively mentors stakeholders, simplifies complex issues, and is currently developing written thought leadership to broaden his impact.
