Episodes

Most people think negotiation is about getting what you want. In reality, it’s about understanding what the other person needs. In this episode of The Pleasant Street Pod, host Taylor Nissi, CFP®, CEPA, welcomes negotiation expert and Black Swan Group trainer Jonathan B. Smith for a conversation about tactical empathy, active listening, and how better communication can improve leadership, business decisions, and relationships. Taylor and Jonathan discuss: Why tactical empathy creates better out...

What if you didn’t have to sell your investments every time you needed cash? There’s a different way to think about liquidity, and most people have never heard of it. In this episode of The Pleasant Street Pod, host Taylor Nissi, CFP®, CEPA, sits down with Joseph Wang, Co-Founder and Chief Revenue Officer of SyntheticFI. They get into a tool that’s been showing up more and more in real client conversations, especially for high earners and entrepreneurs who have built significant portfolios but s...

Growth sounds exciting, but most entrepreneurs hit a point where what used to work suddenly stops working. The challenge is not just growing the business; it’s changing how you lead it. In this episode of The Pleasant Street Pod, host Taylor Nissi, CFP®, CEPA, sits down with Dan Bubniak, certified EOS implementer and former COO/CFO, to unpack what it takes to scale a business with clarity, structure, and confidence. Dan shares lessons from helping grow a family business 20x, including why decisi...

What if “everything looks normal” is actually the problem? For high performers, average health may be the very thing holding you back. In this episode of The Pleasant Street Pod, host Taylor Nissi, CFP®, CEPA, sits down with biologist and Second Prime founder Andrew Martin to explore what it really means to take a proactive, data-driven approach to health. Andrew shares his personal journey through years of unresolved health challenges and how that experience led him to help entrepreneurs optimi...

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: The R...

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 taugh...

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 ...

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...

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 finance...

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 W...

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....

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 Pos...