AI After Dark

Alex Gras
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AI After Dark is a podcast hosted by Alex Gras, venture capitalist at Mercury, focused on how real companies are built once the hype fades and the hard decisions begin. Through candid conversations with founders, CTOs, and operators, the show cuts through buzzwords to talk about people, systems, risk, and the trade-offs that actually matter. Alex brings a background as an operator, founder, and revenue leader, with a belief that technology matters, but people come first. This podcast is for builders who care less about trends and more about what lasts.

  1. 2d ago

    "You Completely Automated My Job." Now What?

    Margaritas and a little league draft app somehow turned into a business. Zach Smith left Uber, bought a small dental benefits company, and now runs Houston AI Help, embedding with small and mid sized firms around town to build the stuff they did not know they could have. He gets into quick wins over month long discovery, why he will not rip out the software that runs your company, running his whole day through agents, and the moment his wife realized he had automated her job. Click here to watch a video of this episode. Join the conversation shaping the future of energy.Collide is the community where oil & gas professionals connect, share insights, and solve real-world problems together. No noise. No fluff. Just the discussions that move our industry forward.Apply today at collide.io Click here to view the episode transcript. 0:00 How legacy industries actually adopt AI1:15 Margaritas, little league, and starting Houston AI Help3:49 Two hour whiteboard beats a month of discovery7:34 Six hours versus six months on the first quick win11:52 What Zach will not build for you15:37 Running an entire business on agents19:33 Uber data lessons and permanent corporate memory23:42 Going to market without cold calling mom and pops28:41 The wife who got her job automated32:24 Bay Area bubble versus everybody else36:08 Why he is not raising venture money39:25 Disposable software that still pays off45:05 Zooming out on the weekly report48:14 Getting AI to grill you instead49:47 What year two might look likehttps://twitter.com/collide_aihttps://www.tiktok.com/@collide.iohttps://www.facebook.com/collide.iohttps://www.instagram.com/collide.iohttps://www.youtube.com/@collide_iohttps://bsky.app/profile/collide-ai.bsky.socialhttps://www.linkedin.com/company/collideai

  2. Aug 18

    We Want Everyone Using AI. Then We Judge Them for It

    Front porches became phone lines, phone lines became chat rooms, and now the whole conversation is a thumbs up emoji. That is the thread Prasanth Chilukuri, Founder and Managing Partner of Soul Street Ventures, pulls on here, from running the same health question through four different AI models to treating one as his chief strategist to the thing that actually keeps him up at night, which is what happens to his kids when the center keeps moving and nobody can say where it should land. Click here to watch a video of this episode. Join the conversation shaping the future of energy.Collide is the community where oil & gas professionals connect, share insights, and solve real-world problems together. No noise. No fluff. Just the discussions that move our industry forward.Apply today at collide.io Click here to view the episode transcript. 0:00:00 London, kids, and escaping the Houston summer 0:01:50 Building an AI tutor for a third grader 0:03:15 Why AI projects never actually get finished 0:07:00 Soul Street Ventures and portfolio companies figuring out AI 0:08:15 Taking health into his own hands 0:14:20 Trust but verify across four models 0:15:45 AI as chief strategist 0:18:00 Everybody's board deck is AI generated now 0:20:45 Starlink on planes and not reading anymore 0:24:35 Turning 41 and thinking is working 0:27:15 Front porches to phone lines to emojis 0:29:35 Brown water and the AI filter 0:33:00 What happens to human connection 0:36:15 Singularity, Elon, and the abundance case 0:43:25 Travel when everywhere has evolved with you 0:48:30 Vibe coding and building from nothing 0:50:10 Your AI will never disappoint you 0:53:57 The salt shaker and moving the center 0:59:07 School has not changed and neither has the path 1:04:55 The greatest sci fi story is the one we are in https://twitter.com/collide_ai https://www.tiktok.com/@collide.io https://www.facebook.com/collide.io https://www.instagram.com/collide.io https://www.youtube.com/@collide_io https://bsky.app/profile/collide-ai.bsky.social https://www.linkedin.com/company/collideai

  3. Jul 28

    AI Can Do Anything. That’s the Problem.

    Blockchain was supposed to fix oil and gas payments. It didn't. Cameron Sinclair, CEO of SmartChain, explains why the company traded smart blockchain for smart supply chain, and why leading a pitch with AI is the fastest way to lose the room. There's talk of dirty boots as a sales strategy, the grandfather's ax problem of rebuilding your stack every month, and why this industry can smell nonsense from across the table. Click here to watch a video of this episode. Join the conversation shaping the future of energy.Collide is the community where oil & gas professionals connect, share insights, and solve real-world problems together. No noise. No fluff. Just the discussions that move our industry forward.Apply today at collide.io Click here to view the episode transcript. 0:00:00 From blockchain to supply chain 0:02:31 Why technology can't lead the pitch 0:07:10 Selling AI enabled, not AI first 0:10:47 Agents that read invoices like people 0:15:33 Everything becomes table stakes 0:17:36 Dirty boots and earned trust 0:19:31 Why the big AI houses struggle here 0:25:48 The grandfather's ax problem 0:28:38 Nobody knows what tokens will cost 0:35:24 Building a leaner team 0:40:09 Knowing when to stop vibe coding 0:44:13 The graveyard of micro apps 0:47:36 The case for intrapreneur programs 0:57:37 Where AI hasn't helped 1:00:09 How Alex uses AI day to day 1:03:45 The Tesla automation lesson https://twitter.com/collide_ai https://www.tiktok.com/@collide.io https://www.facebook.com/collide.io https://www.instagram.com/collide.io https://www.youtube.com/@collide_io https://bsky.app/profile/collide-ai.bsky.social https://www.linkedin.com/company/collideai

  4. Jul 16

    AI Is Making Software Easier to Build and Harder to Buy

    Innovation gets treated like a tech problem, but Patrick Keltner of Griffin Partners argues it's really about people and building the space to actually change. He breaks down why most of the 6,000 proptech startups don't move the needle, how his team builds with AI instead of building AI, and the buried tenant retention gap they found by fixing governance before touching the data. Also why trust and human judgment still matter when anyone can just hand the work to a model. Click here to watch a video of this episode. Join the conversation shaping the future of energy.Collide is the community where oil & gas professionals connect, share insights, and solve real-world problems together. No noise. No fluff. Just the discussions that move our industry forward.Apply today at collide.io Click here to view the episode transcript. 00:00  What innovation actually means (people, not just tech)02:00  Creating space for change without mandating it05:45  Adopting AI outside the startup bubble08:00  6,000 proptech startups and the point solution trap13:00  The framework for buying vs building16:00  Rolling out Claude, and the foundational model risk19:00  Who's really paying for all these tokens22:00  Lease abstraction and the snowball effect24:00  Standing out with trust and the human component30:00  His role as the connector between teams36:00  The tenant retention data mess37:30  Fix your governance before your data40:00  The retention gap nobody underwrites for43:00  Build with AI vs build AI, and deterministic predictors47:00  The biggest unlock: an AI that manages the noise50:00  Short-termism and wrapping uphttps://twitter.com/collide_ai https://www.tiktok.com/@collide.io https://www.facebook.com/collide.io https://www.instagram.com/collide.io https://www.youtube.com/@collide_io https://bsky.app/profile/collide-ai.bsky.social https://www.linkedin.com/company/collideai

  5. Jun 23

    He’s Building an AI Transaction Coordinator for Real Estate

    From a food startup that accidentally became a catering company, to a fitness business he sold, to a real estate tool launching now, Nathaniel McNamara has surfed every tech wave since the first web browser. Building Dealyo, he gets into why focus beats boiling the ocean, how he lost money slowly on Polymarket to learn faster, and why optimism keeps winning the AI argument with his wife. Click here to watch a video of this episode. Join the conversation shaping the future of energy.Collide is the community where oil & gas professionals connect, share insights, and solve real-world problems together. No noise. No fluff. Just the discussions that move our industry forward.Apply today at collide.io Click here to view the episode transcript. 0:00:00   The food-to-fitness studio story0:05:20   Tech cycles from the first browser to AI0:07:48   Why intelligence keeps getting cheaper0:13:46   Time off and the projects that didn't stick0:16:31   How Dealyo started with a real estate headache0:18:15   Being the service, not just the tool0:22:15   Single player now, big business later0:28:10   Houston versus the coastal tech scenes0:32:16   Why focus beats boiling the ocean0:37:47   Faster horse or build the car0:40:05   Spending now to win later0:44:01   Losing money slowly on prediction markets0:52:08   Optimism, humanities, and self-driving cars0:59:28   Staying focused on what's nexthttps://twitter.com/collide_ai https://www.tiktok.com/@collide.io https://www.facebook.com/collide.io https://www.instagram.com/collide.io https://www.youtube.com/@collide_io https://bsky.app/profile/collide-ai.bsky.social https://www.linkedin.com/company/collideai

  6. Jun 9

    How AI Agents Are Changing Grocery Shopping Forever

    What happens when the models keep doubling and you have to bet your whole company on where they land? Daniel Vitiello of Cooklist Inc. gets into building AI native from day one, why his rule is to never delegate understanding, and how the right harness turns a general model into something that actually ships. Also the pivot from consumer app to powering grocery e commerce, agents that do your shopping, and a wild take on self sovereign AI earning its own money by 2029. Click here to watch a video of this episode. Join the conversation shaping the future of energy.Collide is the community where oil & gas professionals connect, share insights, and solve real-world problems together. No noise. No fluff. Just the discussions that move our industry forward.Apply today at collide.io Click here to view the episode transcript. 0:00:00 Why AI has been the bet since 20130:02:12 Building an AI native team0:04:30 Never delegate understanding0:06:11 Cooklist and the food data play0:08:48 The jump from ML to agentic AI0:12:34 Betting on the exponential0:15:53 When the models start eating software0:22:32 Disintermediating judgment0:24:41 Why humanities still matter0:27:19 The harness and the wrapper debate0:33:22 The human as the bottleneck0:38:26 A year of work built in a weekend0:42:16 Daniel's road to becoming a builder0:46:58 What Cooklist is today0:52:16 Agentic search and merchandising0:58:07 A controversial take on self sovereign AIhttps://twitter.com/collide_ai https://www.tiktok.com/@collide.io https://www.facebook.com/collide.io https://www.instagram.com/collide.io https://www.youtube.com/@collide_io https://bsky.app/profile/collide-ai.bsky.social https://www.linkedin.com/company/collideai

  7. May 28

    Ex-CIA Operator: Why America Is Losing The Cyber War

    Ashley Vaughan spent years inside the CIA running cyber ops before realizing the tools meant to keep clandestine work invisible were leaving fingerprints all over the blockchain. Now she is building Numan, a stealth startup using AI and crypto rails to create private financial infrastructure for national security ops and anyone who needs money movement to stay quiet. She gets into polygraph interviews, why the agency treats disruptors like black sheep, and why space could be the next frontier. Click here to watch a video of this episode. Join the conversation shaping the future of energy.Collide is the community where oil & gas professionals connect, share insights, and solve real-world problems together. No noise. No fluff. Just the discussions that move our industry forward.Apply today at collide.io Click here to view the episode transcript. 0:00 What Ashley is building in stealth1:20 Getting recruited into the CIA at 254:30 The leap of faith and the mission pull6:40 The resume gap nobody can read8:30 Why she left the agency11:15 Disruptors as black sheep14:35 Playing poker against China and Russia15:55 Offense will always beat defense17:15 Why crypto rails are leaking intelligence19:25 Suitcases of cash do not work anymore21:40 Introducing Numan24:14 How the wallet works for operators25:53 Building alongside the customer28:55 Why government adoption is broken33:41 Trading repeatability for security38:43 Raising pre-seed and the road ahead44:29 Why the agency looks nothing like TV45:53 Skip a generation46:17 China is playing the long game49:53 Trust as the founder advantage50:20 Silicon Valley discovers defense tech52:15 Trying to land a one liner54:22 Outpacing private sector copycats55:19 What one ups Numan57:03 Electromagnetic warfare and old oil rigs59:31 Nobody planned for the digital attack1:02:00 The most controversial position

  8. May 12

    Ex-JPM Trader: Why Expertise Is No Longer The Edge

    Seven years trading at JP Morgan, a Fulbright scholarship to the US, and one circled line in a careers book at Warwick. Anekha Sokhal, Founder and Machine Learning Engineer at Moshi, walks through how she's building an AI-native analyst platform for energy and macro traders. We get into screen real estate wars on trading desks, why people lie about their workflows, building Toyotas instead of Ferraris, and what it actually takes to leave a dream job to chase a harder one. Click here to watch a video of this episode. Join the conversation shaping the future of energy.Collide is the community where oil & gas professionals connect, share insights, and solve real-world problems together. No noise. No fluff. Just the discussions that move our industry forward.Apply today at collide.io Click here to view the episode transcript. 00:00 - Screen real estate and the death of the application04:00 - Building Moshi after eight years of trading08:00 - Tribal knowledge, generational gaps, and AI FOMO12:30 - A statistical edge in a zero-sum industry17:30 - Toyotas vs Ferraris and learning to fail fast23:30 - Team culture at startup speed27:00 - Solo founding and always selling33:30 - From a careers book at Warwick to JP Morgan37:00 - Leaving the dream job for a Fulbright to Rice43:30 - Prioritization and listening without taking it personally49:30 - The hard moments and finding conviction

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About

AI After Dark is a podcast hosted by Alex Gras, venture capitalist at Mercury, focused on how real companies are built once the hype fades and the hard decisions begin. Through candid conversations with founders, CTOs, and operators, the show cuts through buzzwords to talk about people, systems, risk, and the trade-offs that actually matter. Alex brings a background as an operator, founder, and revenue leader, with a belief that technology matters, but people come first. This podcast is for builders who care less about trends and more about what lasts.

Information

  • Creator
    Alex Gras
  • Years Active
    2026
  • Episodes
    14
  • Rating
    Explicit
  • Copyright
    © 2025 Digital Wildcatters, Inc
  • Show Website
    AI After Dark