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:

• LinkedIn: Stefan Cherneski
• StefanCherneski@lifeadvisorsolutions.com
• (860) 874-2750

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.