Gemini Gets an Upgrade, Rare Character Steals the Show, and the Fifth Segment Goes Off

Gemini Gets an Upgrade, Rare Character Steals the Show, and the Fifth Segment Goes Off

Brad jumps back into his discussion of the top AI Apps picking up with the newly upgraded Gemini AI App after Google’s big conference announcements, and he breaks down Gemini Spark, Gemini Daily Brief, Gemini 3.5 Flash, and the ambitious Gemini Omni. The guys crack open a killer bottle of bourbon from former guest and friend Eric Kowalski. It’s a Rare Character Limited Release, Batch No. 02, and they give it the full Bourbon with Brad treatment. Brad shares a couple of past head‑stand adventures, gambling stories, and the kind of personal chaos that only comes out over a good pour. And as always, the Fifth Segment delivers pure, lighthearted, next‑level laughter. Pour a glass and join us. Cheers! Legal Disclaimer: The views & opinions shared on the Podcast are our own & those of our guests. Nothing we discuss should be taken as financial, legal, business, or gambling advice. Don’t make investment, business, or betting decisions based on our conversations as you should always talk to a qualified professional. Listeners must always drink responsibly, never drink & drive, & only consume alcohol if you are of legal drinking age. Disclosure: Some of the images in the Podcast were AI generated &/or edited with AI. The cover image was AI generated. The voice overs are original AI generated voices. The theme music is an original instrumental created using AI. Support this podcast at — https://redcircle.com/bourbon-with-brad/donations [https://redcircle.com/bourbon-with-brad/donations] Advertising Inquiries: https://redcircle.com/brands [https://redcircle.com/brands] Privacy & Opt-Out: https://redcircle.com/privacy [https://redcircle.com/privacy]

Omar Periu: Mentors, Mistakes & the Magic of Not Taking Yourself Too Seriously

The Bourbon with Brad crew uncorked a legendary pour this week. The iconic Horse Soldier Bourbon, forged in fire by the very soldiers who rode into Afghanistan on horseback after 9/11. Its story sets the tone perfectly for a conversation built on grit, legacy, and the kind of wisdom you only get from a life fully lived. And our special guest? Omar Periu — the New York Times bestselling author, peak‑performance architect, and legendary mentor to millions brings the heat. Omar opens up with powerful, deeply human stories about: * Business breakthroughs that shaped his career * Meaningful Mentorship moments * Family lessons that grounded his success * The mindset required to build wealth, resilience, and purpose But don’t worry as this isn’t a lecture. Brad, Lou, and Perry are in full form, which means: * A dangerous amount of laughter * Lou’s ongoing quest to define the perfect Loubricity Level * Perry’s great commentary  * Brad trying (and failing) to keep the show on the rails It’s inspiring. It’s unfiltered. It’s hilarious. And it’s one of the most energizing episodes we’ve ever recorded. Pour a glass of Horse Soldier. Settle in. And get ready to rethink what’s possible. Cheers! Legal Disclaimer: The views & opinions shared on the Podcast are our own & those of our guests. Nothing we discuss should be taken as financial, legal, business, or gambling advice. Don’t make investment, business, or betting decisions based on our conversations as you should always talk to a qualified professional. Listeners must always drink responsibly, never drink & drive, & only consume alcohol if you are of legal drinking age. Disclosure: Some of the images in the Podcast were AI generated &/or edited with AI. The cover image was AI generated. The voice overs are original AI generated voices. The theme music is an original instrumental created using AI. Support this podcast at — https://redcircle.com/bourbon-with-brad/donations [https://redcircle.com/bourbon-with-brad/donations] Advertising Inquiries: https://redcircle.com/brands [https://redcircle.com/brands] Privacy & Opt-Out: https://redcircle.com/privacy [https://redcircle.com/privacy]

AI & Crypto Headlines - May 18, 2026

It’s a packed news cycle. Trump and Xi met in Beijing with AI chips on the table and walked away empty-handed. Anthropic is closing in on a $30 billion raise at a near-trillion-dollar valuation, just days after announcing a $200 million deal with the Gates Foundation to bring AI to global health, farming, and education. OpenAI launched a whole new deployment company. Google I/O opens tomorrow with Gemini under pressure. The entire founding team at SpaceXAI has walked out the door. Bitcoin is taking a macro beating. And AI-powered hackers are coming for the crypto sector. Pour something good — there’s a lot to get into. Legal Disclaimer: The views & opinions shared on the Podcast are our own & those of our guests. Nothing we discuss should be taken as financial, legal, business, or gambling advice. Don’t make investment, business, or betting decisions based on our conversations as you should always talk to a qualified professional. Listeners must always drink responsibly, never drink & drive, & only consume alcohol if you are of legal drinking age. Disclosure: Some of the images in the Podcast were AI generated &/or edited with AI. The cover image was AI generated. The voice overs are original AI generated voices. The theme music is an original instrumental created using AI. Support this podcast at — https://redcircle.com/bourbon-with-brad/donations [https://redcircle.com/bourbon-with-brad/donations] Advertising Inquiries: https://redcircle.com/brands [https://redcircle.com/brands] Privacy & Opt-Out: https://redcircle.com/privacy [https://redcircle.com/privacy]

Orbiting Data Centers, Penelope Pours, and the 5th Segment Chaos

Tonight’s pour is the classic Penelope Bourbon, and it sets the tone for an episode that swings from the stratosphere to the seafloor. Brad kicks things off by asking the week’s most unhinged infrastructure question: If we’re putting data centers in orbit and in the ocean… why not slap them on the poles too? The logic is questionable. The bourbon is not. From there, the conversation shifts as we wrap up our thoughts on Claude and dive headfirst into Microsoft Copilot—what it is, what it isn’t, and why it’s about to reshape how people work. And of course… it wouldn’t be Bourbon with Brad without The 5th Segment—the part of the show where structure goes to die and the best ideas somehow show up anyway. Legal Disclaimer: The views & opinions shared on the Podcast are our own & those of our guests. Nothing we discuss should be taken as financial, legal, business, or gambling advice. Don’t make investment, business, or betting decisions based on our conversations as you should always talk to a qualified professional. Listeners must always drink responsibly, never drink & drive, & only consume alcohol if you are of legal drinking age. Disclosure: Some of the images in the Podcast were AI generated &/or edited with AI. The cover image was AI generated. The voice overs are original AI generated voices. The theme music is an original instrumental created using AI. Support this podcast at — https://redcircle.com/bourbon-with-brad/donations [https://redcircle.com/bourbon-with-brad/donations] Advertising Inquiries: https://redcircle.com/brands [https://redcircle.com/brands] Privacy & Opt-Out: https://redcircle.com/privacy [https://redcircle.com/privacy]

AI & Crypto Daily Headlines - May 14, 2026

The AI world surges ahead as CloakBrowser cracks every major bot‑detection suite, Google’s Addy Osmani pushes agents into real engineering workflows, and Anthropic locks in a $1.8B compute deal while Mistral races toward $1B ARR on sovereign‑AI demand. OpenAI drops a real‑time translation blueprint, Anthropic reveals how “evil AI” fiction can distort model behavior, Allen AI debuts a self‑organizing MoE breakthrough, and Google blocks the first AI‑discovered zero‑day. In Washington, Microsoft CTO Kevin Scott testifies about the pivotal 2018 email at the center of Musk’s allegations. On the crypto side, Ether ETFs smash records with a $726M inflow while Bitcoin whipsaws below $79K after $304M in longs are liquidated on hot inflation data. Legal Disclaimer: The views & opinions shared on the Podcast are our own & those of our guests. Nothing we discuss should be taken as financial, legal, business, or gambling advice. Don’t make investment, business, or betting decisions based on our conversations as you should always talk to a qualified professional. Listeners must always drink responsibly, never drink & drive, & only consume alcohol if you are of legal drinking age. Disclosure: Some of the images in the Podcast were AI generated &/or edited with AI. The cover image was AI generated. The voice overs are original AI generated voices. The theme music is an original instrumental created using AI. Support this podcast at — https://redcircle.com/bourbon-with-brad/donations [https://redcircle.com/bourbon-with-brad/donations] Advertising Inquiries: https://redcircle.com/brands [https://redcircle.com/brands] Privacy & Opt-Out: https://redcircle.com/privacy [https://redcircle.com/privacy]