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.