Leave or Stick: The Complexity of Career Choices

Guy Kawasaki learned sales the hard way in the jewelry business, where every deal felt like hand-to-hand combat. With no technical background, he later joined Apple and turned those street-level selling skills into world-class software evangelism. He went on to become Chief Evangelist at Canva, shaping how the world thinks about selling ideas. In this episode, Guy breaks down why selling is the most critical skill for entrepreneurs, the sales strategies that helped him win pitches, and how to identify products or ideas that sell.

In this episode, Hala and Guy will discuss:

(00:00) Introduction

(01:29) From Sales Rookie to Apple Evangelist

(07:35) How to Get Your Big Break

(11:49) Leadership Lessons From Apple and Beyond

(17:51) The Art of Knowing When to Quit

(24:53) How Big Career Risks Shape Success

(33:22) Mastering the Sales and Pitch Strategy

(42:07) Evangelism Strategy: Pitch Everyone, Always

(47:43) Building Likability, Trust, and Competence

Guy Kawasaki is a bestselling author, keynote speaker, and the Chief Evangelist of Canva. He previously served as the Chief Evangelist at Apple, where he popularized the concept of secular evangelism and helped make the Macintosh a household name. Guy is also the creator and host of the Remarkable People podcast, featuring world-class entrepreneurs and innovators.

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Resources Mentioned:

Guy’s Website: remarkablepeople.com   

Guy’s Book, Wise Guy: bit.ly/-WiseGuy 

Guy’s Book, Enchantment: bit.ly/-Enchantment 

Guy’s Podcast, Remarkable People: bit.ly/RP-apple 

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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, Startup, Mental Health, Career, Leadership, Mindset, Health, Growth Mindset, Online Selling, Economics, E-commerce, Ecommerce, Prospecting, Persuasion, Inbound, Value Selling, Account Management, Scale, Scaling, Sales Podcast