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.

Building a thriving company requires more than strategy and execution. But what if the key to becoming a better leader lies in embracing your vulnerabilities rather than hiding them?

How can authenticity transform your relationships with employees, family, and yourself? What role does purpose play when financial goals are met but fulfillment remains elusive?

In this episode, Taylor Nissi, CFP®, CEPA, sits down with Todd Palmer, Coach & Retreat Facilitator at Extraordinary Advisors and author of From Suck to Success, to explore how business owners can break through obstacles by leading with authenticity, transparency, and vulnerability. Todd shares his journey from being $600,000 in debt to making the Inc. 5,000 list six times, and reveals the frameworks that helped him turn his company and life around while addressing imposter syndrome and building genuine connections.

Todd discusses:

• How authenticity, transparency, and vulnerability (ATV) helped him overcome imposter syndrome and transform his leadership
• Why open-book management builds trust with employees and teaches financial literacy across the organization
• The Ikigai concept and how identifying your true purpose prevents post-exit emptiness and regret
• Why setting intentions rather than expectations leads to faster iteration and better problem-solving
• How breaking generational trauma through honest conversations strengthens family relationships and business outcomes
• And more!

Resources:

• Strategic Wealth Scorecard (2-minute assessment): Strategic Wealth Score Card
• Book: From Suck to Success by Todd Palmer

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 Todd Palmer:

• LinkedIn: Todd D. Palmer
• Website: Extraordinary Advisors

About our Guest:

Todd Palmer is a coach and retreat facilitator at Extraordinary Advisors, a global corporate human capital consultancy that leads organizations and their leaders to undergo significant transformation. With over 25 years of experience as a CEO, entrepreneur, author, and keynote speaker, he has made it his mission to improve lives by teaching, guiding, and empowering leaders and entrepreneurs on how to take the complex and make it simple regarding human capital and culture.

He works with growth-minded leaders and entrepreneurs who want to achieve their highest personal and organizational potential. He helps them adopt a growth mindset and develop the necessary business skills to create a business and life by design. He also helps them become employers of choice, inspiring their employees to be engaged, loyal, and connected. He uses a proven four-step model that defines, stabilizes, and strengthens organizational leadership and culture. Through his work, he enables leaders and entrepreneurs to overcome any internal challenges that impact decision-making, such as imposter syndrome, fear, or self-doubt.

Building a business demands everything from you. But what if the key to performing at your best isn’t working harder, but working smarter with your biology?

How can busy founders manage stress without overhauling their lives? What small, science-backed changes actually move the needle on focus, resilience, and clarity?

In this episode, Taylor Nissi, CFP®, CEPA, sits down with Jamey Maniscalco, PhD, a neuroscientist and founder of Manifest Wellness, to explore how entrepreneurs can leverage brain science for better performance. Jamey shares his journey from studying stress in graduate school to founding a wellness startup focused on accessible, evidence-based practices. The conversation unpacks how stress can be beneficial, why neuroplasticity matters, and practical techniques like the physiological sigh that take seconds but deliver real results.

Jamey discusses:

• His transition from neuroscience professor to wellness startup founder focused on accessible health practices
• Why stress isn’t always harmful and how perception changes mortality outcomes by up to 60%
• The physiological sigh breathing technique that calms your nervous system in 10 seconds
• How neuroplasticity allows you to rewire thought patterns through intentional practice
• Why hustle culture undermines cognitive performance and how rest fuels creativity
• And more!

Resources:

• Strategic Wealth Scorecard (2-minute assessment): Strategic Wealth Score Card
• The Upside of Stress by Kelly McGonigal (book)

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 Jamey Maniscalco:

• LinkedIn: Jamey Maniscalco
• Website: Manifest Wellness
• Instagram: Jamey Maniscalco (@nextdoorneuro)

About our Guest:

Jamey Maniscalco is a neuroscientist and the Founder of Manifest Wellness, a health-focused startup designed to meet people where they are in their daily lives. With a background spanning academic research, pharmaceuticals, consulting, and higher education, Jamey brings neuroscience out of the lab and into practical, everyday habits. His work centers on stress, behavior change, and small intentional practices that support clarity, focus, and emotional balance for busy professionals and entrepreneurs.