EPISODE · Apr 23, 2026 · 53 MIN
April 23, 2026 - Unchained Bobby Mascia and Portal AI Volodymyr Panchenko
from School for Startups Radio · host Jim Beach
Bobby Mascia – CEO of Green Ridge Wealth Planning and Author of Unchained: The Raw Truth About Entrepreneurship, Family Business and Life Balance We’re trying to unchain business owners from feeling like they bought themselves a really expensive job. Robert Mascia, known as “Bobby” to loved ones and clients alike, is a seasoned entrepreneur with a unique background working both on Wall Street and as an owner of several successful businesses. His story begins after graduating from Lehigh University with degrees in finance and marketing, which positioned him to launch his career in downtown New York as a hedge fund and assets management consultant. In 2003, Bobby took an unplanned hiatus from the Street to do something he had sworn off completely – working in the family franchise business. He saw no other choice when 9/11 and his parents’ personal health scares forced him to step away from his dream career. For nine years, Bobby learned every aspect of the Dunkin’ business and played a key role in expanding it. During his time there, Bobby helped grow his family’s ownership from 20 to 40 locations and $50m in revenue by developing a strong team and leveraging strategic partnerships. While this venture had forced him to abandon finance, it was, unbeknownst to him at the time, preparing him for much bigger things to come. Working with family can come with consequences, and by 2011, Bobby found his relationship with his father deteriorating. At the same time, his love of finance had never waned. Bobby knew that he had reached a fork in the road—continue his current journey or pivot into the unknown. He took a hard right and risked it all to do what he loved. Bobby spent several years preparing to take the giant step of starting his own firm. His vision was to create a financial planning and investment management experience that differed from what he had seen firsthand. He also knew that he had a unique proposition for business owners and entrepreneurs—a wealth of knowledge from his years of firsthand experience in the family business. Among the most valuable lessons he had learned about achieving financial success was the importance of quality relationships with smart, capable professionals. By 2016, he was ready and launched Green Ridge Wealth Planning. Fast forward to the present day. Bobby has built a firm true to his vision, offering business owners, individuals and families a boutique, highly personalized financial planning and investment management experience. He continues to stay true to his promise to be transparent, accessible and reliable, giving his firm what clients call “a family feel.” Bobby has built a team that shares his vision and passion for excellence. The result? A growing business where clients trust our team to guide them through life’s financial complexities so that they can live their best lives. Volodymyr Panchenko – CEO and Co-Founder of Portal AI Everyone has a personal AI agent, which can remember, care and do anything you want for you, about you and with you. Volodymyr Panchenko, CEO and co-founder of Portal.ai, He recently launched Portal One+, a platform built around persistent AI agents that remember context, understand users over time, and help execute tasks and workflows continuously rather than resetting each session. Previously, he founded DMarket, a digital asset marketplace acquired by Mythical Games, giving him firsthand experience with scaling, fundraising, and exiting in fast-moving markets. He can speak to why most founder–investor conversations fail in the first 10 minutes, how continuity and context change decision-making, what founders misunderstand about investor psychology, and how AI is shifting from reactive tools to systems that support ongoing execution.
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April 23, 2026 - Unchained Bobby Mascia and Portal AI Volodymyr Panchenko
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