What if the biggest challenge after success is not building more, but knowing what comes next? This episode explores the decisions that quietly shape an entrepreneur’s wealth, time, and sense of freedom.

In this episode of The Pleasant Street Pod, host Taylor Nissi, CFP®, CEPA, sits down with Ali Nasser, Amazon #1 bestselling author of The Business Owner’s Dilemma, to unpack the core challenges high-performing entrepreneurs face as their businesses and wealth grow.

Taylor and Ali discuss:

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About our Guest:

Ali Nasser is the #1 Amazon best-selling author of “The Business Owner’s Dilemma.” He is a passionate entrepreneur and life enthusiast whose goal is to help business owners realize their life’s work.

For over two decades, Ali has been guiding business owners on how to integrate business, wealth, and life decisions to create the Return on Life Experience they truly desire.

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:

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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:

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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:

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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:

And more!

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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:

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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:

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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.