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AI After Dark

AI After Dark

By: 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.2025 Digital Wildcatters, Inc Economics
Episodes
  • He’s Building an AI Transaction Coordinator for Real Estate

    He’s Building an AI Transaction Coordinator for Real Estate
    Jun 23 2026

    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 story
    0:05:20 Tech cycles from the first browser to AI
    0:07:48 Why intelligence keeps getting cheaper
    0:13:46 Time off and the projects that didn't stick
    0:16:31 How Dealyo started with a real estate headache
    0:18:15 Being the service, not just the tool
    0:22:15 Single player now, big business later
    0:28:10 Houston versus the coastal tech scenes
    0:32:16 Why focus beats boiling the ocean
    0:37:47 Faster horse or build the car
    0:40:05 Spending now to win later
    0:44:01 Losing money slowly on prediction markets
    0:52:08 Optimism, humanities, and self-driving cars
    0:59:28 Staying focused on what's next

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    1 hr and 1 min
  • How AI Agents Are Changing Grocery Shopping Forever

    How AI Agents Are Changing Grocery Shopping Forever
    Jun 9 2026

    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 2013
    0:02:12 Building an AI native team
    0:04:30 Never delegate understanding
    0:06:11 Cooklist and the food data play
    0:08:48 The jump from ML to agentic AI
    0:12:34 Betting on the exponential
    0:15:53 When the models start eating software
    0:22:32 Disintermediating judgment
    0:24:41 Why humanities still matter
    0:27:19 The harness and the wrapper debate
    0:33:22 The human as the bottleneck
    0:38:26 A year of work built in a weekend
    0:42:16 Daniel's road to becoming a builder
    0:46:58 What Cooklist is today
    0:52:16 Agentic search and merchandising
    0:58:07 A controversial take on self sovereign AI

    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
    Show More Show Less
    1 hr
  • Ex-CIA Operator: Why America Is Losing The Cyber War

    Ex-CIA Operator: Why America Is Losing The Cyber War
    May 28 2026

    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 stealth
    1:20 Getting recruited into the CIA at 25
    4:30 The leap of faith and the mission pull
    6:40 The resume gap nobody can read
    8:30 Why she left the agency
    11:15 Disruptors as black sheep
    14:35 Playing poker against China and Russia
    15:55 Offense will always beat defense
    17:15 Why crypto rails are leaking intelligence
    19:25 Suitcases of cash do not work anymore
    21:40 Introducing Numan
    24:14 How the wallet works for operators
    25:53 Building alongside the customer
    28:55 Why government adoption is broken
    33:41 Trading repeatability for security
    38:43 Raising pre-seed and the road ahead
    44:29 Why the agency looks nothing like TV
    45:53 Skip a generation
    46:17 China is playing the long game
    49:53 Trust as the founder advantage
    50:20 Silicon Valley discovers defense tech
    52:15 Trying to land a one liner
    54:22 Outpacing private sector copycats
    55:19 What one ups Numan
    57:03 Electromagnetic warfare and old oil rigs
    59:31 Nobody planned for the digital attack
    1:02:00 The most controversial position
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    1 hr and 5 mins
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