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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, I tackle a question I get all the time: 1099 vs W2 — which should you hire? I break down the real differences, share a story about two moving companies that taught me the lesson, and explain why the choice impacts your company culture more than your bank account. Then, for the first time, I share my own Better Humanness Reporting — what I’m reading, how I’m training, and my biggest wins personally and professionally this past week. This is a new style of episode, going a bit longer and behind the scenes. I’d love your feedback.
💡 Key Takeaways:
- 1099 contractors may save money in the short term, but they rarely build long-term culture.
- W2 employees allow you to invest in leadership, development, and a real “crew.”
- Culture is built by consistent teams, not random contractors pieced together.
- Leadership after the first million in business is about succeeding through people.
- Better Humanness Reporting: training, reading, and wins help leaders connect at a deeper level.
⏱️ Chapters:
- 00:00 Intro & New Style of Episode
- 01:10 1099 vs W2 — The Real Question
- 03:00 The Moving Company Story (Contractors vs Crews)
- 06:20 Why W2 Employees Build Better Culture
- 09:00 Leadership Beyond a Million — Succeeding Through People
- 11:30 Introducing Better Humanness Reporting
- 12:15 My Training This Week
- 13:50 What I’m Reading Right Now
- 15:10 Personal & Professional Wins
- 16:30 Asking for Your Feedback
Connect with me: Instagram: https://www.instagram.com/jerred.moon/ My site: https://better.biz Get my book: https://bit.ly/killingcomfort
#leadership #businessgrowth #companyculture #entrepreneurship #tryharder
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