Robert C. Kulle, Jr. is the Founder and CEO of Heritage Capital Strategies, Inc., a boutique firm offering life insurance and wealth-transfer solutions for businesses and high-net-worth families. He leverages his analytical acumen and partnership with M Financial Group to oversee more than $1.5 billion in death benefit coverage, delivering customized, tax-efficient insurance strategies. Based in Westlake Village, California, Robert is also registered with M Holdings Securities and holds securities licenses such as Series 63 and Series 66. In 2025, Forbes named him one of Southern California’s Top Best-in-State Financial Security Professionals.
Here’s a glimpse of what you’ll learn:
- [4:21] Robert Kulle reflects on being recognized by Forbes as a top financial security professional in Southern California
- [8:48] The risks of leaving teaching to pursue a career in financial services
- [12:47] How growing up in a small town in upstate New York shaped Robert’s values
- [15:54] Heritage Capital Strategies’ plan for differentiating through analytics and education
- [18:54] Overcoming negative perceptions of the life insurance industry and building client trust
- [41:16] Common pitfalls in life insurance policies and examples of client successes
In this episode…
Many entrepreneurs underestimate the role of life insurance in their overall financial strategy, often seeing it as just another box to check. Misconceptions, confusing products, and a lack of reviews can leave business owners vulnerable to risks that threaten their families, businesses, and legacies. How can entrepreneurs cut through complexity and ensure their coverage actually protects what matters most?
Robert Kulle, a financial security professional specializing in life insurance planning, emphasizes the importance of education, transparency, and periodic reviews. Robert highlights how entrepreneurs should align their insurance with their broader financial goals, approach coverage with the same discipline they use in investing, and choose advisors with the right licenses to access all available products. He stresses flexibility, client-first planning, and the need to avoid one-size-fits-all solutions that often lead to costly mistakes.
In this episode of The Road Already Traveled, Rich Schuette interviews Robert C. Kulle, Jr., Founder and CEO of Heritage Capital Strategies, about misconceptions in life insurance and smarter strategies for entrepreneurs. Robert shares the importance of regular policy reviews and aligning coverage with financial goals. He also discusses lessons he learned from entrepreneurship, the impact of stress on business owners, and how proper planning safeguards generational wealth.
Resources mentioned in this episode:
- Rich Schuette on LinkedIn
- Avalan Wealth
- Robert Kulle on LinkedIn
- Heritage Capital Strategies: Website | Phone: (805) 604-2728
- M Financial Group
Quotable Moments:
- “To be ranked recognized as the top risk manager in Southern California is really a career highlight.”
- “The supply of 230 hitters far exceeded the demand back then, and that was sobering.”
- “Sometimes the clients and the advisory teams aren’t even willing to explore insurance because of distrust.”
- “Finding that balance between the education, the flexibility, and the simplicity has been a really big boost.”
- “Ninety percent of the life insurance field force doesn’t have a FINRA license to sell variable products.”
Action Steps:
- Schedule regular insurance policy reviews: Frequent checkups ensure coverage aligns with life changes and evolving financial goals.
- Choose advisors with full licensing: Working with specialists who hold all the necessary credentials opens access to the best products.
- Align insurance with overall financial strategy: Treat premiums like other investments so protection complements long-term wealth-building goals.
- Prioritize flexibility and simplicity in planning: Clear, adaptable strategies save entrepreneurs time while safeguarding against unexpected risks.
- Educate yourself and your advisory team: A solid understanding of risks and products prevents costly mistakes and builds lasting trust.
Sponsor for this episode…
This episode is sponsored by Avalan, a wealth management firm dedicated to personalized financial, business, and investment planning.
We work with select high-net-worth individuals, corporations, and trusts, providing guidance tailored to their unique needs.
From supercar entrepreneurs to music industry entrepreneurs, our team employs proven investment strategies to help them preserve wealth, protect assets, and plan charitable giving.
With an unwavering focus on world-class service, our relationships are built to last generations, helping clients achieve lifelong goals through a thoughtful, consultative approach.
To learn how Avalan can empower you to reach your goals, visit https://www.avalanwealth.com/contact/.