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.