AI After Dark

About AI After Dark

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.

Publisher

Alex Gras

Category

business · technology

Language

en

Explicit

No

First episode

18 Feb 2026

Latest episode

10 Sept 2026

Latest episodes

15 episodes in the feed.

1. 

   10 Sept 2026

   "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. (https://app.collide.io/content/PGwRWid) 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 (http://collide.io/) Click here to view the episode transcript. (https://share.transistor.fm/s/9d996897/transcript) 0:00 How legacy industries actually adopt AI 1:15 Margaritas, little league, and starting Houston AI Help 3:49 Two hour whiteboard beats a month of discovery 7:34 Six hours versus six months on the first quick win 11:52 What Zach will not build for you 15:37 Running an entire business on agents 19:33 Uber data lessons and permanent corporate memory 23:42 Going to market without cold calling mom and pops 28:41 The wife who got her job automated 32:24 Bay Area bubble versus everybody else 36:08 Why he is not raising venture money 39:25 Disposable software that still pays off 45:05 Zooming out on the weekly report 48:14 Getting AI to grill you instead 49:47 What year two might look like 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

2. 

   18 Aug 2026

   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. (https://app.collide.io/content/Wp7aHfM) 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 (http://collide.io/) Click here to view the episode transcript. (https://share.transistor.fm/s/79de0a81/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. 

   28 Jul 2026

   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 (http://collide.io/) Click here to view the episode transcript. (https://share.transistor.fm/s/b7bbe422/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. 

   16 Jul 2026

   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. (https://app.collide.io/content/vw544ke) 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 (http://collide.io/) Click here to view the episode transcript. (https://share.transistor.fm/s/3357b692/transcript) 00:00  What innovation actually means (people, not just tech) 02:00  Creating space for change without mandating it 05:45  Adopting AI outside the startup bubble 08:00  6,000 proptech startups and the point solution trap 13:00  The framework for buying vs building 16:00  Rolling out Claude, and the foundational model risk 19:00  Who's really paying for all these tokens 22:00  Lease abstraction and the snowball effect 24:00  Standing out with trust and the human component 30:00  His role as the connector between teams 36:00  The tenant retention data mess 37:30  Fix your governance before your data 40:00  The retention gap nobody underwrites for 43:00  Build with AI vs build AI, and deterministic predictors 47:00  The biggest unlock: an AI that manages the noise 50:00  Short-termism and wrapping up 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

5. 

   23 Jun 2026

   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. (https://app.collide.io/content/XTJgnqU) 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 (http://collide.io/) Click here to view the episode transcript. (https://share.transistor.fm/s/ace5a355/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 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

6. 

   9 Jun 2026

   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 (http://collide.io/) 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

7. 

   28 May 2026

   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. (https://app.collide.io/content/1x8wmgF) 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 (http://collide.io/) Click here to view the episode transcript. (https://share.transistor.fm/s/49fd5d3c/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

8. 

   12 May 2026

   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. (https://app.collide.io/content/4FWDRaw) 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 (http://collide.io/) Click here to view the episode transcript. (https://share.transistor.fm/s/4f8ae41f/transcript) 00:00 - Screen real estate and the death of the application 04:00 - Building Moshi after eight years of trading 08:00 - Tribal knowledge, generational gaps, and AI FOMO 12:30 - A statistical edge in a zero-sum industry 17:30 - Toyotas vs Ferraris and learning to fail fast 23:30 - Team culture at startup speed 27:00 - Solo founding and always selling 33:30 - From a careers book at Warwick to JP Morgan 37:00 - Leaving the dream job for a Fulbright to Rice 43:30 - Prioritization and listening without taking it personally 49:30 - The hard moments and finding conviction

9. 

   29 Apr 2026

   How AI Turned a Designer Into a CTO

   Going from designer to CTO sounds like an impossible career pivot, but Kyle Ledbetter, Co-Founder and CTO of Dreambase, walks through how AI handed him the permission slip he didn't know he needed. We get into building a Dream Team of data agents on top of Supabase, why dashboards are just the Trojan horse, agent orchestration, the case for CLI as the default interface, and the slightly terrifying moment his wife's AI generated Instagram feed knew her better than he did. Click here to watch a video of this episode. (https://app.collide.io/content/bHQxRfS) 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 (http://collide.io/) Click here to view the episode transcript. (https://share.transistor.fm/s/1b59cad8/transcript) 00:00 From designer to CTO 04:30 The co-founder unlock and imposter syndrome 07:30 Rethinking team design with AI 10:00 Mini CEOs and agents as employees 12:00 The Dream Team of data agents 15:00 Why Dream Base sits on Supabase 18:30 Why can't Claude just build this 21:00 Specialization beats generalists 25:00 MCP apps and email as UI 30:30 Critical thinking for the next generation 37:30 What keeps Kyle up at night 42:00 Faster horse vs building a car 45:00 Legacy industries adopting AI 48:00 What comes after dashboards 50:30 The rise of the CLI 54:00 When the algorithm knows you better than your spouse 58:00 What Dream Base really is

10. 

    21 Apr 2026

    Why This AI Startup Doesn't Use AI For Math

    Hunter Honnessy, CTO and Co-Founder at Unlimited.ai, gets into what defensibility actually looks like when anyone can vibe code a SaaS over a weekend. Conversation runs through building moats with data plus intelligence layers, why finance software doesn't have to suck, forward deployed engineering, where vibe coding leaves junior devs, a grounded take on AI fear mongering, and why 2026 is the year agentic workflows stop being primitive. Click here to watch a video of this episode. (https://app.collide.io/content/cXt1GHQ) 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 (http://collide.io/) Click here to view the episode transcript. (https://share.transistor.fm/s/891cc9d4/transcript) 0:00:00 Defensibility in an AI-native world 0:04:00 User delight and the wow factor as a moat 0:07:00 Who Unlimited serves and finance's legacy problem 0:11:00 Why business-minded CTOs ship faster 0:15:00 Monthly releases and cutting prototypes to hours 0:21:00 Forward deployed engineering and what keeps Hunter up at night 0:26:00 Vibe coding and the future of junior engineers 0:33:00 Painkillers vs vitamins and how Unlimited came together 0:39:00 Hiring cracked engineers and the Jim Simons lesson 0:45:00 AI as augmentation, not replacement 0:46:30 2026 as the year of agentic workflows 0:52:45 What's next for Hunter and Unlimited 0:57:00 AI fear mongering vs the good news nobody reports 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

11. 

    7 Apr 2026

    How AI Cut Hiring From 42 Days To An Afternoon

    Alex Gras sits down with Gustavo Herrera, Founder and CTO of Knowme Global, to talk through why recruiting still sucks and how AI might actually fix it by doing the one thing everyone avoids, sitting down and talking to people for two hours. Gustavo breaks down why LLMs are just glorified averaging, how he picked Llama Index over LangChain by keeping it simple, and why the industry's obsession with automation is backwards when the hardest part is capturing who someone actually is. They dig into prompt versus context engineering, why philosophy matters more than people think, and how AI is forcing everyone back to the most human things we do. Click here to watch a video of this episode. (https://app.collide.io/content/cS8mvnC) 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 (http://collide.io/) Click here to view the episode transcript. (https://share.transistor.fm/s/45b14e89/transcript) 0:00 - Why Gustavo went back to school to learn AI for recruiting 4:30 - Choosing tech stacks and avoiding bleeding edge tools 9:15 - How Knowme ingests long-format interviews to build candidate profiles 14:45 - Prompt engineering versus context engineering 19:00 - Why LLMs will never be truly intelligent 24:20 - Philosophy's role in shaping AI and society 30:45 - How employers don't actually know what they want 36:15 - Speeding up the 42-day hiring process with AI interviews 42:00 - Why Knowme does the unscalable thing nobody wants to do 47:30 - Preventing AI from embellishing candidate answers 54:10 - Training interviewers to strike the right conversational tone 58:45 - When to use deterministic solutions versus agentic AI 1:01:40 - AI bringing us back to our humanity https://twitter.com/collide_io 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/digitalwildcatters.bsky.social https://www.linkedin.com/company/collide-digital-wildcatters

12. 

    24 Mar 2026

    The Best AI Product Is The One You Never Log Into

    Bowden Kelly from Nutiliti joins Alex on AI After Dark to explain why being a fast follower beats bleeding-edge adoption, particularly when your customers just want accurate utility bills paid on time and don't care about your tech stack. He breaks down why AI native companies often confuse magic demos with production reality, why replacing his entire engineering team with agents would be insane, and how the paradigm shift isn't about chat interfaces but building artifacts that make high school interns into experienced employees. The conversation reveals why Nutiliti spent years building PDF parsers only to discover LLMs weren't good enough yet, his controversial take that the agentic AI wave is overhyped, and how the hiring equation is flipping from one PM managing ten engineers to five PMs with two engineers because code execution is getting commoditized while business reasoning stays expensive. Click here to watch a video of this episode. (https://app.collide.io/content/2JRPQiy) 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 (http://collide.io/) Click here to view the episode transcript. (https://share.transistor.fm/s/61513b12/transcript) 00:00 Fast follower versus bleeding edge adoption philosophy 07:38 Paradigm shifts from blockchain to mobile to AI 13:29 Tech debt concerns and why Google engineer stories mislead 21:10 Cloud Code improvements and managing context windows 28:04 MCP servers and the actual problem of data access 34:47 Why non-technical users aren't ready for AI interfaces 39:07 Building artifacts versus executing tasks as organizational design 46:17 High school intern analogy for training agentic AI 51:18 Controversial take on AI being overhyped despite being valuable 55:02 Hiring shift from programmers to business-minded builders 01;06;05 Fundraising strategy for non-unicorn companies 01;08;05 Why companies force AI into products for the story https://twitter.com/collide_io 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/digitalwildcatters.bsky.social https://www.linkedin.com/company/collide-digital-wildcatters

13. 

    10 Mar 2026

    How AI Could Turn 100,000 Homes Into A Power Plant

    Matt Robillard from SmartAC joins Alex on AI After Dark to explain why he walked into a company with product-market fit but antiquated tech stack and immediately started rewriting everything with AI at its core. He breaks down the difference between horizontal process automation that Service Titan can eventually replicate versus vertical intelligence modeling the actual thermodynamics of HVAC systems that nobody else can touch, why clean energy is magical thinking constrained by the Shockley-Queisser limit and Betz limit, and how hiring the best AI talent in HVAC meant recruiting from SpaceX, Databricks and Perplexity by selling real-world impact over another CRM with AI slapped on. The conversation reveals why OEMs surprisingly embrace their solution instead of fearing disruption, his controversial take that LLMs are stochastic parrots not true intelligence, and how the marginal cost of code going to zero is pure hype when production systems at scale still require senior engineers who deeply understand customer pain points. Click here to watch a video of this episode. (https://app.collide.io/content/aG7ieEM) 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 (http://collide.io/) Click here to view the episode transcript. (https://share.transistor.fm/s/8c3e3964/transcript) 00:00 CES takeaways and hardware semiconductor relationships 01:53 Joining SmartAC post product-market fit with legacy tech 07:15 Data platform challenges and ML model development 12:14 Vertical AI defensibility versus horizontal automation 18:26 Alignment with Josh and commercial-product pairing 24:17 Replatforming effort and organizational design overhaul 29:27 Recruiting top AI talent from SpaceX and Databricks 36:03 Development velocity changes and junior engineer growth 41:01 AGI possibility and stochastic parrots debate 48:21 Controversial clean energy physics constraints opinion 56:42 Smart home promises and Tesla-style behavioral nudges 01;01;10 VC organizational design mistakes over two years 01;05;13 Who else should be on AI After Dark https://twitter.com/collide_io 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/digitalwildcatters.bsky.social https://www.linkedin.com/company/collide-digital-wildcatters

14. 

    24 Feb 2026

    Chat Is The Lousiest Way To Interact With AI

    Akhil Mantripragada from Pie joins Alex on AI After Dark to trace his journey from coding without a computer in eighth grade India to building a $100M+ revenue AI-native marketing platform for SMBs. He shares how changing seven schools growing up forced him to become adaptable, why he spent hours writing multiple code versions on paper with only one hour per week at a computer lab, and how selling his first ed-tech company to UTSA funded grad school at Columbia. The conversation reveals why Pi's first three hires were designers instead of engineers, his controversial belief that chat is the "lousiest way to interact with AI," and how meeting users where they're at - not where you want them to be - became the core design philosophy that lets three engineers do what used to take thirty. Plus, the framework for building modular systems where perfection lies in the architecture's inputs and outputs, not the code inside the black box. Click here to watch a video of this episode. (https://app.collide.io/content/ymw8nq9) 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 (http://collide.io/) Click here to view the episode transcript. (https://share.transistor.fm/s/c9f56a20/transcript) 00:00 Growing up moving between seven schools in India 01:39 Learning to code without a computer access 07:13 Starting an events management company as an introvert 12:18 The arrogance and humility combination that drives builders 15:12 First website job at UTSA and learning by doing 18:01 Building quantitative literacy tracking system for professors 24:17 Why school being too easy created entrepreneurial opportunities 26:45 Columbia grad school and starting Edu Link collaboration tool 35:14 The two acquisition experiences and MIT licensing lessons 40:56 Blockchain land registry in India and creator platform experiments 43:35 Why education will become skill-based not credit-based 46:15 Joining Toast's New Ventures program and building benchmarking 56:07 Recruiting A-players through bias for action and ownership 01;02;40 Why Pi hired three designers before the first engineer 01;06;54 Meeting users where they're at versus forcing chat interfaces 01;12;48 The black box modularity philosophy for AI-native startups https://twitter.com/collide_io 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/digitalwildcatters.bsky.social https://www.linkedin.com/company/collide-digital-wildcatters

15. 

    18 Feb 2026

    Why The First Hire For An AI Startup Isn't An AI Engineer

    In this kickoff to a new series, AI After Dark, Alex Gras (VC @ Mercury Fund) talks with Canisius Rozario (CTO @ Collide) about how he built a top-tier AI team in oil & gas without any industry background. It’s a sharp, candid look at hiring, learning fast, and building AI-first systems, packed with practical takeaways for founders, CTOs, and early builders working in high-stakes, data-heavy industries. Click here to watch a video of this episode. (https://app.collide.io/content/mHkFKRx) 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 (http://collide.io/) Click here to view the episode transcript. (https://share.transistor.fm/s/55173814/transcript) 0:00 Introduction and series kickoff 1:50 Canisius career background and journey through tech 9:30 Joining Collide and the decision to go AI-native 20:00 First 90 days as CTO and the "sniff test" 33:00 Why senior engineers beat junior hires in AI builds 37:00 Incorporating oil and gas experts into AI model training 41:45 The Forward Deploy Engineer model and how it works 46:00 Prioritization process for POCs and customer feedback 52:50 What to look for in the next generation of AI CTOs 56:30 What does "AI native" actually mean and audience Q&A https://twitter.com/collide_io 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/digitalwildcatters.bsky.social https://www.linkedin.com/company/collide-digital-wildcatters

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