First Sip

Welcome to First Sip! I'm Dekimbe Smith, your host, and every week we sit down for curious conversations about building wealth, growing a business, and showing up in your career and life with intention. Just the kind of conversations you wish you were having with someone who gets it. Whether you're figuring out how to start your first business, or want to make smarter career moves, First Sip is where curious people come to level up. New episodes drop weekly. So grab your drink, press play, and as always...enjoy your first sip!

First Sip is a business podcast hosted by Dekimbe Smith, with 160 episodes on record and a Required Pod Score of 80. PitchCentric scores this show on Booking Probability, Listen Score, and live audience signals refreshed every 24 hours.

Dekimbe Smith hosts First Sip, a business show with 160 episodes published.

Our AI reads these to draft pitches. Use them as grounding for a pitch that cites a real guest and a specific topic.

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  Episode #161

  He Was Right About AI...So How Did He Lose $35 Billion?

  Aug 11, 202616 minS4

  A former OpenAI researcher correctly saw where the AI boom was headed, built a hedge fund around that prediction, and watched it grow to roughly $45 billion in assets. Then July happened. Leopold Aschenbrenner’s Situational Awareness fund lost 67% of its portfolio, wiping out roughly $35 billion. But the interesting part of this story is that his original bet on AI may not have been wrong. So how do you lose $35 billion while being right about the bigger trend? In this episode of First Sip, I break down what happened, what a hedge fund actually is, how leverage can multiply both your wins and losses, and how a margin call can force you to sell an investment even when you still believe in it. More importantly, we get into the lesson that applies far beyond Wall Street: being right doesn’t matter if you don’t have enough runway to survive being early. If you’re building a business, investing, using debt, or betting on an idea you believe in, this is a story worth understanding. Stay tuned, stay curious, and as always, enjoy your first sip. Click here to watch the full episode on YouTube What did you think about this episode? -------------------------------- Get the First Sip Field Notes: A weekly newsletter for curious people building better businesses, careers, and lives. You'll also get a free tool to help you decide if that idea you're sitting on is actually worth building. https://firstsipfieldnotes.beehiiv.com/subscribe CONNECT WITH DEKIMBE: YouTube Instagram Facebook LinkedIn FOLLOW THE PODCAST: Instagram Apple Podcasts Spotify For podcast sponsorship & advertising opportunities please contact: firstsippod@gmail.com

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  Episode #160

  Checkpoints: How to Stop Restarting From Zero | Business & Career | EP. 160

  Jul 21, 202613 minS4

  Survival mode isn't a setting you choose. Its a setting we get locked into, that piles on quietly until you don't even notice it's on. This week breaks down why business owners and employees keep restarting from zero, the research-backed reason it happens, and how to get yourself out of that cycle. Here's what we're sippin on: Why researchers gave this exact mental state a name, and why it's not a discipline problem The real numbers behind accountability What a video game character's stat sheet gets right about progress that most of us get wrong in real life The people who keep moving aren't the ones with more willpower, they're the ones who built a way to check in on themselves before they needed it. Thank you for listening, and as always...enjoy your first sip! Click here to watch the full episode on YouTube What did you think about this episode? -------------------------------- Get the First Sip Field Notes: A weekly newsletter for curious people building better businesses, careers, and lives. You'll also get a free tool to help you decide if that idea you're sitting on is actually worth building. https://firstsipfieldnotes.beehiiv.com/subscribe CONNECT WITH DEKIMBE: YouTube Instagram Facebook LinkedIn FOLLOW THE PODCAST: Instagram Apple Podcasts Spotify For podcast sponsorship & advertising opportunities please contact: firstsippod@gmail.com

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  Episode #159

  ChatGPT 5.6 vs Claude: Why Picking a Side Is the Wrong Move | Business & AI | EP. 159

  Jul 14, 202615 minS4

  ChatGPT vs Claude is the debate everyone's back to having this week, thanks to the release of ChatGPT 5.6. People are asking if they should switch back after just getting comfortable with Claude, and the honest answer is that's the wrong question to be asking in the first place. Click here to watch the full episode on YouTube Here's what we're sippin on: Why becoming AI literate matters more right now than picking the "right" tool, and how to actually get there without feeling behind A simple way to know which one to reach for depending on what you're actually trying to get done that day Why you don't have to be techy to get real value out of either one, and the easiest way to just get started The real risk right now isn't picking the wrong AI tool, it's sitting on the sidelines while everyone else is moving forward. Thank you for listening, and as always...enjoy your first sip! TIMESTAMPS: 00:00 — The ChatGPT vs Claude debate, PlayStation vs Xbox style 00:57 — Welcome back, why "which one's better" is the wrong question 03:15 — ChatGPT: the everyday ecosystem vs Claude's edge for deep work 05:36 — Connecting tools to Notion, and why preference matters most 07:54 — Becoming a "power user" and running into usage limits 10:11 — Splitting the work between tools, and standing out at your job 12:27 — Where to start if you're new, plus image generation and taste 14:42 — The adoption curve, and where you want to be What did you think about this episode? -------------------------------- Get the First Sip Field Notes: A weekly newsletter for curious people building better businesses, careers, and lives. You'll also get a free tool to help you decide if that idea you're sitting on is actually worth building. https://firstsipfieldnotes.beehiiv.com/subscribe CONNECT WITH DEKIMBE: YouTube Instagram Facebook LinkedIn FOLLOW THE PODCAST: Instagram Apple Podcasts Spotify For podcast sponsorship & advertising opportunities please contact: firstsippod@gmail.com

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  Episode #158

  The AI-Darwin Moment: 90% of Employees Aren't Ready for What’s Coming | EP. 158

  Jul 7, 202613 minS4

  The CEO of a $270 billion cybersecurity company just said 90% of his own employees aren't ready for what AI is bringing next. Nikesh Arora of Palo Alto Networks isn't doing mass layoffs to solve this, he's rebuilding his company through hackathons and natural attrition instead. This week we break down what he actually said on the 20VC podcast, why he's pushing back on companies like Coinbase and Block for cutting jobs instead of building people up, and what this AI skills gap really means for the average professional, not just the tech industry. Plus, why this whole moment feels a lot like the one our parents lived through when computers first showed up at work. Here's what we're sippin on: The exact numbers behind his 12-month and 3-year plan, and what he says happens if he's right How to tell if your role is one of the "replaceable" ones he's really talking about One question to ask your parents that explains exactly where this AI moment is headed Five years from now, this either ages like a warning you caught early or one you ignored. Thank you for listening, and as always...enjoy your first sip! Click here to watch the full episode on YouTube Timestamps: 00:00 The 90% AI Readiness Problem 01:00 Settling In: The Move to Guyana 02:00 Who Is Nikesh Arora and Palo Alto Networks 03:00 Natural Attrition and Hiring Through Hackathons 04:00 The Jobs Most at Risk Right Now 05:00 Calling Out Coinbase and Block's Layoff Approach 06:00 The Parents-and-Computers Parallel 09:00 A Free Tool to Validate Your Next Idea 11:00 Using ChatGPT and Claude to Move Faster 12:00 Are You Seeing This Resistance Too 13:00 Final Thoughts and Sign-Off What did you think about this episode? -------------------------------- Get the First Sip Field Notes: A weekly newsletter for curious people building better businesses, careers, and lives. You'll also get a free tool to help you decide if that idea you're sitting on is actually worth building. https://firstsipfieldnotes.beehiiv.com/subscribe CONNECT WITH DEKIMBE: YouTube Instagram Facebook LinkedIn FOLLOW THE PODCAST: Instagram Apple Podcasts Spotify For podcast sponsorship & advertising opportunities please contact: firstsippod@gmail.com

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  Episode #156

  Anthropic Is Going Public While Customers Cut AI Spend | EP. 156

  Jun 11, 202616 minS3

  The Anthropic IPO is officially in motion. IPO season is back, and companies like Anthropic and SpaceX are leading the race to go public. Anthropic just filed confidentially with the SEC at nearly a trillion dollar valuation, and Claude has been dominating the AI conversation all year. Almost at the same time, two of their biggest customers, Microsoft and Uber, are quietly pulling back on how much they're actually spending on AI. That tension is what this episode is all about. Here's what we're sippin on: What an SEC filing actually means, and why the timing of Anthropic's IPO matters more than the number Why Microsoft and Uber are cutting AI spend even though the tools are working What the Gartner forecast on AI budgets tells us about where this whole thing is headed, and what it means for anyone investing in AI right now If you've been watching the AI market and wondering what any of this means for you on the ground, this one is for you. A SpaceX deep dive is coming soon, so stay subscribed for that one. Thank you for listening, and as always... enjoy your first sip! Click here to watch the full episode on YouTube What did you think about this episode? -------------------------------- JOIN THE NEWSLETTER: Stay sharp on business, career, and life. First Sip Weekly delivers honest lessons, tips, and real conversations from the show to your inbox every week. https://firstsipweekly.beehiiv.com/ CONNECT WITH DEKIMBE: YouTube Instagram Facebook LinkedIn FOLLOW THE PODCAST: Instagram Apple Podcasts Spotify For podcast sponsorship & advertising opportunities please contact: firstsippod@gmail.com

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