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Guy Kawasaki’s journey from a lower-middle-class neighborhood in Hawaii to becoming a Silicon Valley icon is clear proof of grit and transformation. After working in the jewelry business, he pivoted to tech and joined Apple as Chief Evangelist. There, he played a key role in launching the Macintosh, shaping Apple’s brand, and transforming how technology is marketed. Today, Guy is a venture capitalist, startup advisor, and Chief Evangelist at Canva. In this episode, Guy shares his battle with hearing loss, why passion is overrated, his top sales strategies, and advice for scaling a business as an entrepreneur. Guy Kawasaki is a marketing specialist, bestselling author, venture capitalist, and speaker. As the former Chief Evangelist for Apple, he played a pivotal role in launching the Macintosh and now serves as Chief Evangelist at Canva. In this episode, Ilana and Guy will discuss: 00:00 Introduction: Leaving Apple and Career Highlights 01:26 Early Life and Education in Hawaii 03:19 Journey to Silicon Valley 04:17 Choosing Psychology and Law School 05:59 Sales and Marketing Lessons 08:02 The Reality of Sales 10:59 The Decision to Pivot Careers 14:22 The Importance of College and Networking 17:45 Getting into Apple: The Role of Nepotism 22:36 Working with Steve Jobs 26:14 The Art of Evangelism 28:18 Leaving Apple and Entrepreneurial Ventures 30:31 Reflecting on Career Choices and Apple 33:52 The Importance of Strategic Quitting 34:30 Navigating Career Transitions and Challenges 36:08 The Myth of Finding Your Passion 40:11 Embracing Grit and Resilience 44:06 Overcoming Personal Hardships 49:48 Advice for Aspiring Entrepreneurs 56:30 Empathy in Business and Customer Understanding 01:01:08 Final Thoughts and Farewell Guy Kawasaki is a marketing specialist, bestselling author, venture capitalist, and speaker. As the former Chief Evangelist for Apple, he played a pivotal role in launching the Macintosh and now serves as Chief Evangelist at Canva. Despite experiencing hearing loss and receiving a cochlear implant, Guy’s passion for sharing ideas remains unwavering. He hosts the Remarkable People podcast and delivers over fifty keynote speeches annually for clients like Apple, Nike, Google, and Microsoft. Connect with Guy: Guy’s Website: https://guykawasaki.com Guy’s LinkedIn: / guykawasaki Resources Mentioned: Guy’s Podcast, Remarkable People: https://bit.ly/RemarkablePeoplePod Guy’s Book, Think Remarkable: 9 Paths to Transform Your Life and Make a Difference: https://www.amazon.com/Think-Remarkab... 📖Leap Academy📖: LeapCon is the #1 Conference for Reinvention, Leadership & Career — a powerful 3‑day experience designed to help you unlock what’s next in your career and life. 📍 San Jose, CA 📅 Feb 26–28, 2025 If you’re ready to step into clarity, confidence, and bold action, this is your moment. 👉 Grab your ticket before doors close at https://leapacademy.com/leapcon 📈 Ready to reinvent your career and leap into your next big chapter? Leap Academy helps professionals transition into portfolio careers, land board seats, grow executive leadership skills, and unlock multiple income streams through expert coaching, personal branding, and career development strategies. Whether you want to land high-level roles, build a portfolio career, or grow your executive presence—Leap Academy with Ilana Golan is where bold professionals come to grow. 🎯 Start with a free strategy call: https://www.leapacademy.com/yt-schedule 🎓 Watch our free masterclass on building multiple income streams: https://bit.ly/leap--free-training 👇 Like what you see? Comment below and let us know what resonated! 📌 Subscribe for weekly insights, career strategy, and behind-the-scenes mentorship from Ilana: / @ilanagolan-leap-academy ⭐⭐ Hear how others made their leap: https://www.leapacademy.com/reviews 🧠 Explore actionable tips on our blog: https://www.leapacademy.com/blog-1 --------------- 🎧 *PODCAST | Leap Academy with Ilana Golan* Inspiring, unfiltered conversations with top thinkers, leaders, and professionals who broke the mold. Learn how to build your reputation, impact, and income—on your terms. ▶️ https://leapacademy.com/podcast --------------- 🔔 Hit the bell so you never miss a strategy-packed episode. 📲 Connect with Ilana: Facebook ▶️ / ilanagolanleapacademy LinkedIn ▶️ / ilanagolan Instagram ▶️ / ilanagolanleap Website ▶️ https://www.leapacademy.com/ #IlanaGolan #LeapAcademy #PortfolioCareers #CareerStrategy #LeadershipDevelopment #CareerReinvention