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

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Tea with Rich. Getting Real.

Thomas Obrey

28 episodes

5 days ago

Two friends and former agency executives getting real, and talking about life, leadership, and family with business leaders and eCommerce industry visionaries, delivering a rare and raw look at the realities of delivering with excellence. Whether in life, or the office.

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

Tea with Rich. Getting Real.

1 hour 3 minutes 3 seconds

1 month ago

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

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.

Chapters

00:00 Introduction and Personal Updates

02:13 Celebrating Rich's Book Launch

05:16 Pickleball injuries

06:58 The Infamous Tattoo Story

10:16 Micro-dosing and Mental Health

13:04 Transitioning to Fintech at Rate.com

16:00 Financial Literacy and Youth Education

21:41 Understanding Financial Literacy and Cash Flow

24:12 The Mortgage Market and Its Complexities

25:52 Real Estate vs. Stock Market: A Long-Term Perspective

29:41 The Emotional Value of Home Ownership

31:10 Generational Wealth and Family Assets

32:26 Creating Memories vs. Financial Investments

35:26 Culinary Adventures and Personal Connections

42:50 Tattoo Memories and Culinary Adventures

45:13 Cooking Techniques and Personal Recipes

47:45 Food and Romance: A Culinary Love Story

51:27 The Playboy Experience: Insights and Anecdotes

55:44 The Evolution of Online Content and Business Strategies

Peace. -t

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