Episode 22; Getting Real with Scott Stephens of Rate.com

09/10/2025 1h 3min Temporada 2 Episodio 22

Listen "Episode 22; Getting Real with Scott Stephens of Rate.com"

Episode Synopsis

Back from our Summer break, Rich hand I invite a close personal friend, Scott Stephens, to the Podcast. While currently an executive at Rate.com, his career spans a stint at the first SPAM agency (90’s), and as the former COO of Playboy (2000’s), leading their first foray into digital transformation.In this conversation, we are completely unprofessional for most of the episode, with fits of seriousness as we talk about his role at Rate, and their goal of becoming a beacon for financial and health education. Before that however, we discuss his injuries from Pickleball, including knowing himself out and putting his head through a wall to win a point.We also go deep into micro-dosing, our culinary adventures, sharing humorous anecdotes about a potential cooking challenge built around Penne Alla Vodka. They also explore the intersection of food and romance, recounting how cooking has played a significant role in their relationships. The discussion takes a turn towards the professional realm as they reflect on Scott's extensive career at Playboy and the impact of the digital revolution on the brand. The episode is filled with laughter, camaraderie, a shared passion for food, and a good deal of ribbing.Chapters00:00 Introduction and Personal Updates02:13 Celebrating Rich's Book Launch05:16 Pickleball injuries06:58 The Infamous Tattoo Story 10:16 Micro-dosing and Mental Health13:04 Transitioning to Fintech at Rate.com16:00 Financial Literacy and Youth Education21:41 Understanding Financial Literacy and Cash Flow24:12 The Mortgage Market and Its Complexities25:52 Real Estate vs. Stock Market: A Long-Term Perspective29:41 The Emotional Value of Home Ownership31:10 Generational Wealth and Family Assets32:26 Creating Memories vs. Financial Investments35:26 Culinary Adventures and Personal Connections42:50 Tattoo Memories and Culinary Adventures45:13 Cooking Techniques and Personal Recipes47:45 Food and Romance: A Culinary Love Story51:27 The Playboy Experience: Insights and Anecdotes55:44 The Evolution of Online Content and Business StrategiesPeace. -t...

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