1/26/25

Ep. 36 | Upscale Socks | Leonard Underwood | The Journey of Building Two Successful Businesses |

Join us on this episode of the Realistic CEO Podcast as we hear from Lenny, the founder of Underwood Photography and Upscale Socks. Learn how Lenny pursued his dreams despite being told to get a 'real job,' transitioning his passion for photography into a full-time business and later launching a successful sock line inspired by a vivid dream. Lenny shares insights on the importance of networking, the challenges of balancing work and life, and the significance of stepping out of your comfort zone to grow personally and professionally. Don't miss this inspiring conversation filled with practical advice for aspiring entrepreneurs!

00:00 Introduction: Defying Expectations

00:23 Welcome to the Realistic CEO Podcast

00:40 Lenny's Journey: From Hobby to Business

03:01 Overcoming Doubts and Challenges

05:39 The Importance of Networking

08:08 The Birth of Upscale Socks

15:37 Balancing Multiple Ventures

22:55 Advice for Aspiring Entrepreneurs

28:26 Balancing Work and Personal Life

30:12 Fun Facts and Conclusion

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Ep. 37 | Digiarks | Rob Madrid | Journey to Building a Successful Digital Marketing Agency

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Ep. 35 | Link To Libraries | Laurie Flynn | Books as Bridges: Journey to Empower Young Readers