ABOUT THIS PODCAST 🔗

Update frequency:
biweekly
Average audio length:
29 minutes
Guest interviews
English
United States
22 episodes
since Dec. 18, 2025
episodic

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What kind of person earns a software engineering degree, lands a government job, and voluntarily chooses to live in a 1986 Suburban? The kind who understands that a respectable life can still leave you feeling controlled. Everyone around Nickolas Natali could see the comfortable future waiting fo…

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A lot of traditional law firms say they value fresh thinking. They just seem far less interested once the fresh thinking comes from the youngest person in the room. In this episode of The Black Sheep Network, I sit down with Paloma Goggins, founder of Nocturnal Legal, a boutique M&A firm help…
Gen Z has entered the workforce and with 4 different generations now in one office - it’s presenting a problem.  Especially because there’s so many unspoken rules we take for granted.   Like when to speak in a meeting. What “professional” actually means. How much of yourself you’re allowed to bri…
She hit a deep burnout while loving everything she was doing. Nothing about it felt wrong and that is exactly what made it so dangerous. It’s the specific trap Hannah Abad has spent fifteen years pulling high achievers out of. In this episode of The Black Sheep Network, I sat down with Hannah Abad…
There is a version of success that almost every industry rewards. Look the part. Protect your own interests. Follow the playbook. Do business the way it's always been done. Then there are the people who decide that if the rules are built on gatekeeping, they aren't worth following in the first pl…
There is a version of success that looks flawless on paper: a Duke MBA, a career at Deloitte, and a résumé filled with leadership positions. Then there is the version no one sees: waking up at 3 a.m. convinced the life you've worked so hard to build is no longer the one you want. In this episode …
There is a version of leadership that looks impressive from the outside and disconnected on the inside - actually that’s the majority of leaders.  It looks like a calendar packed with meetings. No room to think. No room to breathe. No room to notice what your body has been trying to tell you for m…
Every mentor he paid told him to stop talking to his own software customers. So he listened. Built a 17-person team. Removed himself completely. And watched his company go numb. On this episode of Black Sheep Network, I sit down with Alex Sanfilippo, the founder of Podmatch, and we get into one …
What if the thing everyone said would kill your business is actually what saved it? That is exactly what happened to Stephanie Gross, founder of Bumby Wool. She did not start with a business plan. She started because she could not find what she wanted, so she made it herself. From her basement. …
Becoming a parent comes with a lot of complex questions. And depending on your answer you could be labeled a Black Sheep for life.  On this episode of Black Sheep Network, I sat down with Kristina Miller Weston to talk about Just Wait, an upcoming feature film centered on one of the most emotiona…
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