The Pleasant Street Pod

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 decision-making gets messy when roles are unclear and how the right structure can unlock faster growth. The conversation also explores why so many founders stay stuck at a plateau, and how better systems, stronger accountability, and the right hires can create momentum both in business and in life. Taylor discusses: Why most businesses plateau, and how to recognize when it is time to change The real risk in growth, and why not hiring may cost more than hiring How implementing systems like EOS can reduce friction and improve decision-making What it takes to move from being the operator to becoming the true leader of your business 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 Dan Bubniak: Upper Echelon LinkedIn: Dan Bubniak About our Guest: Dan Bubniak is a certified EOS implementer based in Connecticut who helps entrepreneurs build better businesses and better lives through the Entrepreneurial Operating System. He began his entrepreneurial journey at 24, stepping into a family business as COO and CFO, where he helped scale the company to over 250 employees and achieve 20x growth. Today, Dan works with leadership teams to bring clarity, accountability, and structure to their organizations so they can break through plateaus and grow with intention.