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First Sip

First Sip

Hosted by Dekimbe Smith

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Episodes

160

Latest episode

Aug 2026

Language

EN-US

About the show

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!

Listen to episodes

60 recent
August 11, 2026Episode 16116 min

How an AI Hedge Fund Lost $35 Billion in One Month | Business & Tech | EP. 161

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 YouTubeWhat 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/subscribeCONNECT WITH DEKIMBE: YouTubeInstagram  Facebook LinkedInFOLLOW THE PODCAST:InstagramApple PodcastsSpotifyFor podcast sponsorship & advertising opportunities please contact: firstsippod@gmail.com

July 21, 2026Episode 16012 min

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

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 problemThe real numbers behind accountabilityWhat a video game character's stat sheet gets right about progress that most of us get wrong in real lifeThe 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 YouTubeWhat 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/subscribeCONNECT WITH DEKIMBE: YouTubeInstagram  Facebook LinkedInFOLLOW THE PODCAST:InstagramApple PodcastsSpotifyFor podcast sponsorship & advertising opportunities please contact: firstsippod@gmail.com

July 14, 2026Episode 15915 min

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

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 YouTubeHere'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 behindA simple way to know which one to reach for depending on what you're actually trying to get done that dayWhy you don't have to be techy to get real value out of either one, and the easiest way to just get startedThe 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 style00:57 — Welcome back, why "which one's better" is the wrong question03:15 — ChatGPT: the everyday ecosystem vs Claude's edge for deep work05:36 — Connecting tools to Notion, and why preference matters most07:54 — Becoming a "power user" and running into usage limits10:11 — Splitting the work between tools, and standing out at your job12:27 — Where to start if you're new, plus image generation and taste14:42 — The adoption curve, and where you want to beWhat 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/subscribeCONNECT WITH DEKIMBE: YouTubeInstagram  Facebook LinkedInFOLLOW THE PODCAST:InstagramApple PodcastsSpotifyFor podcast sponsorship & advertising opportunities please contact: firstsippod@gmail.com

July 7, 2026Episode 15813 min

The AI Skills Gap: Why "Darwinian" Is the Right Word for 2026 | Career Growth | EP. 158

Nikesh Arora, CEO of Palo Alto Networks, says 90% of his employees aren't AI-ready. The AI skills gap is quietly becoming the biggest career risk most professionals aren't watching, and instead of mass layoffs, he's rebuilding his team through hackathons and natural attrition.This week we cover what he said on the 20VC podcast, why he's calling out leaders like Coinbase's CEO and Block's Jack Dorsey for how they're handling AI-driven cuts, and why this moment feels a lot like the one our parents lived through when computers first showed up at work and typing classes felt optional. If you've been wondering whether AI will replace your job, this is really a conversation about how to stay ahead of it.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 rightHow to tell if your role is one of the "replaceable" ones he's really talking aboutOne question to ask your parents that explains exactly where this AI moment is headedFive 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 YouTubeTimestamps:00:00 The 90% AI Readiness Problem01:00 Settling In: The Move to Guyana02:00 Who Is Nikesh Arora and Palo Alto Networks03:00 Natural Attrition and Hiring Through Hackathons04:00 The Jobs Most at Risk Right Now05:00 Calling Out Coinbase and Block's Layoff Approach06:00 The Parents-and-Computers Parallel09:00 A Free Tool to Validate Your Next Idea11:00 Using ChatGPT and Claude to Move Faster12:00 Are You Seeing This Resistance Too13:00 Final Thoughts and Sign-OffWhat 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/subscribeCONNECT WITH DEKIMBE: YouTubeInstagram  Facebook LinkedInFOLLOW THE PODCAST:InstagramApple PodcastsSpotifyFor podcast sponsorship & advertising opportunities please contact: firstsippod@gmail.com

June 29, 2026Episode 1578 min

Moving to Guyana: Building a Business From Abroad | Business & Life | EP. 157

After  years of going back and forth, I finally made the decision to move to Guyana. A one way ticket from Philadelphia to Georgetown, with no scheduled return date. Life in Guyana has been something I've been building toward for a while now, from the Airbnb, consulting work, the connections on the ground, and moving there just became the next logical step. This episode is a quick update on what made me pull the trigger, what the business picture actually looks like on the ground in Georgetown, and what Season 4 of the First Sip Podcast is going to look like from here.Here's what we're sippin on:- What finally made the decision click after two-plus years of going back and forth- What Guyana's economic boom actually means at the street level, and why it matters for entrepreneurs right now- What stays the same on the show and what's changing now that First Sip is officially going internationalIf you've been thinking about making a move, going all in on something, or just wondering what it looks like to build a business in a new market, this one is for you.Thank you for listening, and as always...enjoy your first sip!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/subscribeCONNECT WITH DEKIMBE: YouTubeInstagram  Facebook LinkedInFOLLOW THE PODCAST:InstagramApple PodcastsSpotifyFor podcast sponsorship & advertising opportunities please contact: firstsippod@gmail.com

June 11, 2026Episode 15616 min

Anthropic's IPO vs. Shrinking AI Budgets: What the Split Signals | Business & Tech | EP. 156

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 numberWhy Microsoft and Uber are cutting AI spend even though the tools are workingWhat 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 nowIf 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 YouTubeWhat 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/subscribeCONNECT WITH DEKIMBE: YouTubeInstagram  Facebook LinkedInFOLLOW THE PODCAST:InstagramApple PodcastsSpotifyFor podcast sponsorship & advertising opportunities please contact: firstsippod@gmail.com

May 28, 2026Episode 15519 min

AI Data Centers: Who Actually Pays for the Buildout | Business & Tech | EP. 155

Click here to watch the full episode on YouTubeAI data centers are popping up across the country at a pace nobody's really talking about, and they might be the reason your electric bill keeps climbing. This week we're getting into what these data centers actually are, who's really paying for them, and where the money is moving behind the scenes.Here's what we're sippin on:Why your electric bill is climbing even if you're cutting off every light in the houseThe companies getting billions in tax incentives to build in your backyard, and who ends up footing the billHow to position yourself on the right side of a $7 trillion shift instead of just paying for itIf you've noticed your bill going up and you've been wondering what's actually going on behind the scenes, this one is for you.Thank you for listening, and as always... enjoy your first sip!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/subscribeCONNECT WITH DEKIMBE: YouTubeInstagram  Facebook LinkedInFOLLOW THE PODCAST:InstagramApple PodcastsSpotifyFor podcast sponsorship & advertising opportunities please contact: firstsippod@gmail.com

May 12, 2026Episode 15421 min

Claude Has Taken Over the AI Race...For Now | Business & Tech | EP. 154

Click here to watch the full episode on YouTubeMost of us picked one AI tool a couple years ago and never looked back. If that tool is ChatGPT, there is a real chance you’re leaving a lot on the table and you might not even know it yet. This week we’re getting into the AI race as it stands right now in 2026.Here's what we're sippin on:One company just lapped the entire industry and it happened faster than anyone expectedThe four major AI tools broken down so you actually know which one to use and whenHow the company behind Claude is building its own product differently than any tech company before itIf you have been using the same tool since the beginning and wondering why everyone else seems to be moving faster, this one is for you.Thank you for listening, and as always…enjoy your first sip! ━━━━━━━━━━━━━━━━━━━━━━━━TIMESTAMPS00:00 The AI race and why the conversation has changed01:13 Welcome and what we are sipping on today02:00 How Dekimbe has been using AI in his business and life03:00 Breaking down the four major players in the race right now04:43 What LLMs actually are and how they work05:40 Why Claude is the deep thinker and how it compares to ChatGPT07:18 ChatGPT's image generation and where it still wins07:38 Gemini and its integration across the Google Suite08:13 Why Gemini and NotebookLM are a powerful combo for content creators09:18 Grok and where real-time information gives it an edge09:35 How the race shifted and what happened to OpenAI's lead10:38 Anthropic's growth from $9 billion to $30 billion in four months11:12 Why it took Salesforce 20 years to do what Anthropic did in three11:47 Enterprise adoption and over 1,000 companies paying $1M or more a year13:28 Anthropic using Claude Code to write its own code14:24 The Elon and Anthropic data center deal and what it means15:48 How to pick the right AI tool for the right task16:15 The knife analogy breakdown for ChatGPT, Claude, Grok, and Gemini20:06 A simple challenge to compare tools on the same prompt this week21:14 How Claude connects to the tools you are already usingWhat 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/subscribeCONNECT WITH DEKIMBE: YouTubeInstagram  Facebook LinkedInFOLLOW THE PODCAST:InstagramApple PodcastsSpotifyFor podcast sponsorship & advertising opportunities please contact: firstsippod@gmail.com

April 23, 2026Episode 15325 min

The Business Lessons Real Estate Taught Me That Nobody Talks About | Business & Real Estate | EP. 153

Watch the full episode on YouTubeAfter 4 years as a real estate agent in Philadelphia, I'm being honest about what actually happened, what I earned, what I learned, and why I'm making a pivot now.This isn't a real estate episode. It's a business episode. I'm talking about the gap between the fantasy of being your own boss and the reality of building something sustainable, why doing the sales and the marketing at the same time will eventually break you, and how tying your identity to what you do can keep you stuck longer than you should be.I also get into how content marketing quietly worked behind the scenes even while the agent work wasn't, and what that proof of concept is pointing me toward next...If you've ever questioned a pivot, or felt like switching direction meant you failed, this one is for you.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/subscribeCONNECT WITH DEKIMBE: YouTubeInstagram  Facebook LinkedInFOLLOW THE PODCAST:InstagramApple PodcastsSpotifyFor podcast sponsorship & advertising opportunities please contact: firstsippod@gmail.com

March 30, 2026Episode 15258 min

Ryan Conceicao: The LinkedIn Strategy That Gets You in Front of Decision Makers | Career Growth | EP. 152

Watch the Full Episode here on YouTubeImagine applying to dozens of jobs a week for months straight and getting zero interviews. Not one callback. Now imagine someone telling you that the problem was never the job market. It was your process the whole time.This weeks guest, Ryan Conceicao, has spent 11 years in medical sales and the last 8 helping people break into one of the most competitive and well-paying industries out there. He has sat in over 250 interviews himself, built a career coaching program, and is now helping others land their dream job through a job search strategy that actually works in 2026. Like a recent D1 athlete, that went from unemployed to a six figure medical sales offer at one of the most prestigious medical companies in the country in 15 days. Fifteen days.In this episode we get into why most job seekers are networking with the wrong people entirely, the LinkedIn networking tips that get you in the room before you even interview, how AI is quietly giving an unfair advantage to the people who are paying attention, and what it actually means to invest in yourself when time is the only currency that matters.If you have ever felt like the world was moving faster than you, and don't know how to catch up, this one is for you.━━━━━━━━━━━━━━━━━━━━━━━━ TIMESTAMPS00:00 Intro and Ryan's background in medical sales coaching02:00 How Ryan went from helping people one on one to building a course07:00 What Ryan says to people who complain the job market is too hard09:00 The 50/50 formula: networking and interviewing broken down10:30 The LinkedIn strategy that gets you in front of the right hiring manager12:00 How to create raving fans inside companies before you even interview20:00 The D1 athlete who landed a $100K+ medical sales job in 15 days23:00 Why time is the most undervalued currency27:00 Distractions, media noise, and how to stay locked in on what matters36:00 What parenting taught Ryan about self-awareness and behavior42:00 AI is not here to replace you. It is here to make you better43:00 How Ryan's brother built their entire website, funnels, and follow up with AI47:00 The Guyana business opportunity and where AI meets emerging markets52:00 Ryan's closing thoughts on purpose, validation, and why people struggleCONNECT WITH RYAN LinkedInInstagramWhat 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/subscribeCONNECT WITH DEKIMBE: YouTubeInstagram  Facebook LinkedInFOLLOW THE PODCAST:InstagramApple PodcastsSpotifyFor podcast sponsorship & advertising opportunities please contact: firstsippod@gmail.com

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