Young and Profiting with Hala Taha (Entrepreneurship, Sales, Marketing)
Ryan Holiday: How Stoicism Transforms Leadership and Decision-Making in Business | Leadership | E347
22 Apr 2025
Ryan Holiday dropped out of college to apprentice under Robert Greene, gaining invaluable insights on writing, entrepreneurship, leadership, and human nature. This mentorship laid the foundation for his bold marketing campaigns at American Apparel and his rise as a bestselling author and entrepreneur. In this episode, Ryan reveals how stoic principles can sharpen leadership skills, improve decision-making, enhance problem-solving, and empower entrepreneurs to overcome challenges for sustainable growth. In this episode, Hala and Ryan will discuss: (00:00) Introduction (01:44) Robert Greene's Influence on His Career (09:04) Leveraging Controversy for Marketing Success (14:18) Media Manipulation and Its Impact (18:30) The Stoic Approach to Life and Business (26:39) The Four Stoic Virtues for Personal Development (28:01) Embracing the Realities of Entrepreneurship (30:29) Mastering Clear Decision-Making (36:07) The Dangers of Ego in Leadership (38:31) How Stoicism Drives Productivity (42:59) Building Ethical Habits and Leadership Skills (47:50) The Power of Effective Time Management Ryan Holiday is a bestselling author, entrepreneur, and media strategist known for popularizing Stoic philosophy in modern culture. He served as Director of Marketing at American Apparel before founding his creative agency, Brass Check. Ryan’s books, including The Obstacle Is the Way and The Daily Stoic, have sold over 2 million copies in 30 languages. His work helps leaders and creatives apply Stoic principles to overcome challenges. Sponsored By: Shopify - Sign up for a one-dollar-per-month trial period at youngandprofiting.co/shopify Airbnb - Find yourself a co-host at airbnb.com/host Indeed - Get a $75 sponsored job credit at indeed.com/profiting Microsoft Teams - Stop paying for tools. Get everything you need, for free at aka.ms/profiting LinkedIn Marketing Solutions - Get a $100 credit on your next campaign at linkedin.com/profiting Bilt - Start paying rent through Bilt and take advantage of your Neighborhood Benefits™ by going to joinbilt.com/PROFITING. Mercury - Streamline your banking and finances in one place. Learn more at mercury.com/profiting Resources Mentioned: Ryan’s Book, Trust Me, I'm Lying: bit.ly/TrustMeLying Ryan’s Book, Right Thing, Right Now: bit.ly/RightThingNow Ryan’s Podcast, The Daily Stoic: bit.ly/DailyStoicPod Active Deals - youngandprofiting.com/deals Key YAP Links Reviews - ratethispodcast.com/yap Youtube - youtube.com/c/YoungandProfiting LinkedIn - linkedin.com/in/htaha/ Instagram - instagram.com/yapwithhala/ Social + Podcast Services: yapmedia.com Transcripts - youngandprofiting.com/episodes-new Entrepreneurship, Entrepreneurship Podcast, Business, Business Podcast, Self Improvement, Self-Improvement, Personal Development, Starting a Business, Strategy, Investing, Sales, Selling, Psychology, Productivity, Entrepreneurs, AI, Artificial Intelligence, Technology, Marketing, Negotiation, Money, Finance, Side Hustle, Mental Health, Career, Leadership, Mindset, Health, Growth Mindset, Networking, Goal Setting, Strategic Planning, Mindset, Team Building.
Full Episode
Today's episode is sponsored in part by Airbnb and Microsoft Teams. Hosting on Airbnb has never been easier with Airbnb's new co-host network. Find yourself a co-host at Airbnb.com slash host. If you're looking for a way to collaborate with remote workers, your co-founders, interns, and volunteers, then you need to check out Microsoft Teams Free.
Today's episode is sponsored in part by Airbnb and Microsoft Teams. Hosting on Airbnb has never been easier with Airbnb's new co-host network. Find yourself a co-host at Airbnb.com slash host. If you're looking for a way to collaborate with remote workers, your co-founders, interns, and volunteers, then you need to check out Microsoft Teams Free.
Try Microsoft Teams Free today at aka.ms slash profiting. As always, you can find all of our incredible deals in the show notes or at youngandprofiting.com slash deals.
Try Microsoft Teams Free today at aka.ms slash profiting. As always, you can find all of our incredible deals in the show notes or at youngandprofiting.com slash deals.
The Stokes would say that the greatest empire is command of yourself. It's not things that upset us. It's our opinion about things. And realizing like as an entrepreneur, there's no such thing as a good market or a bad market. There just is. Life is objective. That's what the discipline of perception is about. What is the point of doing your own thing if you're not going to do it right?
You're the boss. You get to decide what you pay people, what materials you use. If you're not going to use that to make a positive difference in the world, what are you doing? There's so many ways you can make money. And if money was all you cared about, you should just go work in finance. It's less risky and the upsides are probably higher.
How do you define a good life in Stoic terms?
The Stoics believed that life was...
Yap gang, we are about to go super deep on the podcast today. We're getting philosophical with today's guest, and I can't wait. Ryan Holiday is joining us. He's a philosopher, an entrepreneur, a marketer, and an author who has transformed ancient Stoic principles into actionable insights that we can use as modern entrepreneurs today.
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