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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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You’ve got the idea. The hustle. The vision.
Now the question is—who do you need to build it?
In this episode of The Unsexy Entrepreneur, hosts Charles Harris (CPA, firm owner) and Dr. Seth Jenson (business strategist) dive into one of the most high-stakes decisions every founder must face:
👉 Should you go solo? Bring on a co-founder? Hire employees? Or just outsource?
This conversation is your blueprint for building your startup team the right way—without wasting time, money, or equity.
💡 You’ll Learn:
- Why your first few team decisions shape the future of your business
- When to hire vs. outsource vs. figure it out yourself
- The “value multiplicative” test for bringing on a co-founder
- Why many startup partnerships fail (and how to avoid that fate)
- How to avoid giving away expensive equity when a simple contractor will do
- The real cost of your first hire (it’s not just salary!)
- How to future-proof your business by building around your bottlenecks
- When to trust your long-term vision—and when to just listen to your business
Whether you’re in the Zero to One phase or scaling up your firm, this episode offers practical frameworks and personal stories to help you build smart from the ground up.
17 episodes
