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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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In this episode of the Learnings and Missteps podcast, Jesse reconnects with Megan Shapiro, an accomplished lawyer and repeat guest. They discuss her evolving career and ventures, including launching the Converge Construction Summit and her business coaching initiatives. Megan shares insights on navigating setbacks, growing her network, and intentionally serving her community. With candid stories of her unique branding journey and strategic goals, this episode offers inspiration for professionals looking to leverage their skills and passion for greater impact in their industries.
00:00 Overcoming Setbacks and Learning from Failures
00:18 Introducing the Guest: Megan Shapiro
02:10 The Power of Branding and Personal Style
03:36 Embracing the Pink Blazer: A Branding Journey
06:43 Building a Community and Networking
11:54 The Importance of Tenacity and Resilience
13:09 Creating and Marketing Online Courses
16:41 The Value of Authentic Engagement
21:06 In-Person Networking and Building Relationships
26:20 Exploring New Ventures: Do It Like a Lawyer
31:15 From Conversation to Workshop
31:44 The Make Your Case Workshop
32:29 Challenges with Male Audiences
33:14 Success with Women-Focused Workshops
34:08 Resilience and Rejection
35:41 Expanding Influence and Impact
40:02 Balancing Law and Business
42:43 The Converged Construction Summit
53:47 Future Plans and Intentional Growth
58:23 Final Thoughts and Reflections
Set the stage for an amazing new year with the Self First Framework.
https://calendly.com/jesse04/self-first-webinar
Download a PDF copy of Becoming the Promise You are Intended to Be
https://www.depthbuilder.com/books
Chapters
1. Lessons From a Launch That Flopped (00:00:00)
2. Meet Megan Again: The Repeat Guest (00:02:24)
3. The Hot Pink Brand Origin Story (00:04:20)
4. Embracing Feedback Over Insecurity (00:09:50)
5. The First Course: Built, Launched, Sold Zero (00:12:36)
6. Community, Accountability, and Honest Feedback (00:17:45)
7. How to Build Real Relationships Online (00:22:50)
8. From DMs to Plane Tickets: IRL Connections (00:28:40)
9. Contract Coaching: Offers and Approach (00:33:20)
10. Do It Like a Lawyer: Finding Product-Market Fit (00:38:58)
11. Serving Women in Male-Dominated Industries (00:45:18)
12. Growth Without a Traditional Plan (00:51:03)
13. Converge: Why the Summit Works (00:56:08)
14. Chicago 2026: Format, Dates, and Vision (01:00:58)
202 episodes
