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Ever wondered why so many high-achieving leaders and communicators struggle to recognize their own value? In our 100th episode of Speaking with Confidence, we tackle this powerful question and much more with a very special guest who’s played a major role in my own podcasting journey—Alex Sanfilippo.

I kicked off this milestone episode reflecting on the journey so far and the importance of crafting your communication skills. From day one, Speaking with Confidence has been about helping you show up as your most authentic, impactful self—whether it's in storytelling, leadership, podcasting, or daily conversations. To celebrate our 100th episode, I invited Alex Sanfilippo, founder of PodMatch.com and the host of Podcasting Made Simple, to join me. If you’re not familiar, PodMatch is a brilliant platform that automatically matches podcast hosts and guests, a true game changer for podcasters looking to deliver more value and connect with new audiences.

We dove deep into topics that every communicator and leader will relate to—especially if you’ve ever doubted the impact you make. Alex Sanfilippo shared honestly about his own struggle with imposter syndrome, the challenge of recognizing the ripple effects of our work, and why surrounding yourself with the right people is so critical—not only for accountability but for remembering your successes and celebrating your growth. We reminisced about some of Alex’s earliest lessons as a 10-year-old entrepreneur selling golf balls, and how those negotiations with adults laid the foundation for his confidence and communication today.

Here’s what you’ll learn in this episode:

• Why so many high achievers underestimate their own value and impact
• How imposter syndrome shows up (even for seasoned leaders and creators)
• The importance of community—having people who’ll tell you when you’re doing great and when you need to grow
• How laughter, play, and fun can transform not just your mood, but your effectiveness as a communicator
• Lessons from childhood entrepreneurship that still apply to adult leadership and negotiations
• How to reflect on your day and extract lessons that drive growth
• The difference between representing yourself as a brand and representing a company—and why authenticity matters more than ever
• A powerful story about vulnerability on stage, and how genuine emotion connects more deeply than perfection ever could
• Tips for managing nerves before speaking, including “mindset hacks” to recast anxiety as excitement
• Why storytelling, not just well-organized points, is at the heart of powerful communication
• How to use your walk-up song or other rituals to channel energy and confidence before you speak

Whether you’re a podcaster, leader, or someone simply looking to speak up with more confidence, this 100th episode is packed with honest insights, practical strategies, a few laughs, and plenty of encouragement about the unique value only you can offer.

Thank you for being part of this incredible journey to 100 episodes. Tune in to hear my conversation with Alex Sanfilippo—I promise you’ll walk away ready to communicate (and live!) with more confidence.

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