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.

What happens when founders build something meaningful, sell it, and realize the next chapter is not as clear as expected?

In this episode of The Pleasant Street Pod, host Taylor Nissi, CFP®, CEPA, sits down with serial entrepreneur and private equity investor Chris Cali to unpack the real journey behind building, scaling, and exiting a business, and what most founders do not anticipate along the way.

Taylor discusses:

• The early “ramen and rent” phase of entrepreneurship and how personal finances often take a back seat
• The reinvestment dilemma founders face as businesses begin generating real cash flow
• Lessons learned from selling two companies, including why the highest offer is not always the right one
• The emotional and identity shift many founders experience after an exit, and why planning the next chapter matters

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 Chris Cali:

• Newfound Equity
• LinkedIn: Chris Cali

About our Guest:

Chris Cali is a serial entrepreneur and private equity investor who has built and sold two companies in the technology services space. After starting his career as a software engineer, Chris went on to co-found and scale Spark Digital to hundreds of employees across the U.S. and Argentina before selling the firm to a private equity-backed strategic buyer. Today, he is a partner at Newfound Equity, where he works hands-on with founders to help grow businesses while preserving culture and long-term value.

What happens when an athlete-turned-coach discovers his true calling isn’t on the field, but in helping people design meaningful financial lives? Taylor opens up about the pivotal moments and lessons that shaped his approach to wealth, purpose, and planning.

In this inaugural episode of The Pleasant Street Pod, host Taylor Nissi, CFP®, CEPA, founder of Pleasant Street Wealth Advisors, shares the story behind his journey from athlete and coach to financial advisor and founder of Pleasant Street Wealth Advisors. Taylor opens up about the lessons he carried from sports into business, including discipline, process, and the drive to keep improving, and how those same principles shape the way he helps clients align their wealth with their values.

Listeners will hear why Taylor believes true success is about freedom, purpose, and alignment, not just financial results. He also introduces the firm’s Strategic Wealth Operating System, a holistic framework that integrates wealth management, tax strategy, and life coaching to help entrepreneurs and high achievers design a life they love.

Taylor discusses:

• His journey from athlete and coach to financial advisor and firm founder.
• The discipline, process, and mindset from sports that shape his approach to advising.
• Why he built Pleasant Street Wealth Advisors and the importance of tax-integrated planning.
• How the Strategic Wealth Operating System aligns wealth, values, and life design.
• His philosophy on investing, success, and living a purpose-driven life.
• 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)

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.”

As your business grows, your financial life gets more complex. This episode explores why successful entrepreneurs often outgrow traditional, siloed financial advice, and what an integrated approach can unlock instead.

In this episode of The Pleasant Street Pod, host Taylor Nissi, CFP®, CEPA, sits down with Bill Tucker to share the story behind Pleasant Street Wealth Advisors, the meaning behind the pineapple logo, and the planning philosophy built for growth-focused entrepreneurs and executives.

Taylor discusses:

• Why Pleasant Street Wealth Advisors was founded, and how family, values, and vision shaped the firm
• What “the burden of success” looks like for entrepreneurs, executives, and business owners
• Why siloed advice creates gaps in tax, estate, and risk planning over time
• How the Strategic Wealth Operating System brings structure, cadence, and integration to personal wealth
• 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)

Welcome to The Pleasant Street Pod with Taylor Nissi. This show is for entrepreneurs and high-income earners who want to turn the complexity of success into clarity by aligning vision and values with wealth strategy and life design. Each episode explores how high performers can be intentional with both their wealth and their life to create clarity, peace of mind, and confidence. Taylor shares insights from years of guiding clients toward alignment – what he calls ‘Experiencing Their Wealth’s Possibilities’ – along with conversations with guest experts to help you build wealth that supports your life, business, and legacy.

• Do you want to see how well your Wealth is Aligned with your vision? Take our quick 2-minute Strategic Wealth Scorecard quiz.
• Want personal guidance? Or to get a burning question answered? Schedule a conversation with our team.
• If you want more insights and updates, follow Taylor on LinkedIn for fresh perspectives on building a life of financial purpose.