42:48

In this episode of the You Winning Life Podcast, host Jason Wasser, LMFT, interviews entrepreneur and podcaster Jeremy Siegel. Jeremy shares his journey from aspiring CFO to serial entrepreneur, highlighting how he repeatedly needed to give himself permission to pursue entrepreneurship and to share his voice publicly. He discusses overcoming introversion through Toastmasters and mastermind groups, building a personal brand that amassed over 200,000 organic followers, and launching the "Why Influence" podcast to help others share hidden knowledge. The conversation covers practical tactics for content creation (video vs. audio, re‑editing, challenges), handling criticism and trolls, and advice for introverts on taking the first steps. Jeremy also reflects on the dynamics of an entrepreneurial marriage, the value of strategic retreats, and the importance of discovering and evolving one’s “why.” The episode ends with actionable tips for building a YouTube channel, guest outreach, and a call to listeners to support both podcasts.

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