Building wealth requires more than growing your business. What happens when life takes an unexpected turn?
In this episode of The Pleasant Street Pod, host Taylor Nissi, CFP®, CEPA, sits down with Stefan Cherneski, CFP®, Private Wealth Insurance Specialist, to explore how business owners can protect what they’ve built through strategic risk management. Stefan shares his remarkable journey from being a first-round NHL draft pick to building a career in insurance after a career-ending injury taught him the importance of proper planning.
The conversation unpacks critical insurance strategies, from buy-sell agreements to wealth replacement trusts, and why protecting your business becomes more important as it grows.
Stefan discusses:
- His career-ending injury at 21 and how a disability insurance policy changed his trajectory
- Why business owners underestimate the risk of being the primary rainmaker in their company
- The critical difference between funded and unfunded buy-sell agreements for partnerships
- How wealth replacement trusts preserve family legacies while pursuing charitable objectives
- Why dynamic planning is essential as business values and personal wealth continue to increase: https://strategicwealthscorecard.scoreapp.com/
- And more!
Resources:
- Strategic Wealth Scorecard (2-minute assessment): Strategic Wealth Score Card
Connect with Taylor Nissi:
- Pleasant Street Wealth Advisors
- LinkedIn: Taylor Nissi CFP®, CEPA
- Book some time with Taylor (Book 20 Minute Strategy Call)
Connect with Stefan Cherneski:
About our Guest:
Stefan Cherneski is a Private Wealth Insurance Specialist with extensive experience supporting financial advisors, business owners, and high-income earners. He focuses on integrating insurance solutions into broader personal, business, and estate planning strategies to help address risk and continuity. With a background in economics and hands-on experience working with complex ownership structures, Stefan brings a practical planning perspective shaped by both professional insight and personal experience.
About Taylor Nissi:
Taylor A. Nissi, CFP® CEPA, is a founder of Pleasant Street Wealth Advisors. As a Certified Financial Planner, Taylor provides high-impact financial advice and guidance to individuals, businesses, and families. Taylor also holds the Certified Exit Planning Advisor designation. As a Certified Exit Planning Advisor, Taylor works with business owners of all stages to help them build valuable transferrable businesses.
The Pleasant Street Wealth Advisors team is on a mission to help more people have confidence, peace of mind, and clarity in their financial life. When our clients reach that level of confidence and peace of mind in their financial life, they can spend more time and energy on the people and passions that bring them joy. We call that “Experiencing Your Wealth’s Possibilities.”
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Entrepreneurs and business owners.
Serves a national or global client base.
Based in Westchester County NY
High Net Worth individuals