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 …
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 …
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 …
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®, …
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 …
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 …
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 …
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 …