Complex Systems with Patrick McKenzie (patio11)

• The AI infrastructure stack with Jennifer Li, a16z

  In this episode, Patrick McKenzie (@patio11) is joined by Jennifer Li, a general partner at a16z investing in enterprise, infrastructure and AI. Jennifer breaks down how AI workloads are creating new demands on everything from inference pipelines to observability systems, explaining why we're seeing a bifurcation between language models and diffusion models at the infrastructure level. They explore emerging categories like reinforcement learning environments that help train agents, the evolution of web scraping for agentic workflows, and why Jennifer believes the API economy is about to experience another boom as agents become the primary consumers of software interfaces.–Full transcript: www.complexsystemspodcast.com/the-ai-infrastructure-stack-with-jennifer-li-a16z/–Sponsor:  VantaVanta automates security compliance and builds trust, helping companies streamline ISO, SOC 2, and AI framework certifications. Learn more at https://vanta.com/complex–Links:Jennifer Li’s writing at a16z https://a16z.com/author/jennifer-li/ –Timestamps:(00:00) Intro(00:55) The AI shift and infrastructure(02:24) Diving into middleware and AI models(04:23) Challenges in AI infrastructure(07:07) Real-world applications and optimizations(15:15) Sponsor: Vanta(16:38) Real-world applications and optimizations (cont’d)(19:05) Reinforcement learning and synthetic environments(23:05) The future of SaaS and AI integration(26:02) Observability and self-healing systems(32:49) Web scraping and automation(37:29) API economy and agent interactions(44:47) Wrap

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• Getting better at LLMs, with Zvi Mowshowitz

  In this episode, Patrick McKenzie (patio11) recorded with Zvi Mowshowitz (TheZvi) live at the LessOnline conference. They explore practical strategies for getting better results from large language models. Zvi explains how to customize AI behavior through thoughtful system prompts, while Patrick shares techniques for using LLMs as writing partners and research assistants. They discuss the evolving relationship between content creators and AI training data, touching on the emerging field of "generative engine optimization" (GEO). The conversation also covers multimodal capabilities, recursive AI use, and strategies for avoiding common failure modes like hallucination and sycophancy. –Full transcript: www.complexsystemspodcast.com/getting-better-at-llms-with-zvi-mowshowitz/–Sponsor:  VantaVanta automates security compliance and builds trust, helping companies streamline ISO, SOC 2, and AI framework certifications. Learn more at https://vanta.com/complex–Links:Don’t Worry About the Vase https://thezvi.wordpress.com/ –Timestamps:(01:08) Understanding system prompts(02:04) Customizing LLM behavior(05:58) Memory features in LLMs(10:21) Generative Engine Optimization (GEO)(15:59) Sponsor: Vanta(17:17) Art and AI: Enhancing creativity(20:36) Recursive use of AIs(25:22) Addressing LLM frustrations(27:05) Checking for hallucinations in AI outputs(28:11) Experimenting with AI models(29:44) Optimizing AI prompts and outputs(31:19) Using AI for writing and editing(32:32) AI as a research and writing partner(33:26) Prompting AI and humans effectively(39:39) Balancing AI assistance with personal voice(51:03) Wrap

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• Machine learning meets malware, with Caleb Fenton

  Patrick McKenzie (patio11) discusses software reversing and AI's transformative impact on cybersecurity with Caleb Fenton, co-founder of Delphos Labs. They explore how LLMs are revolutionizing the traditionally tedious work of analyzing compiled binaries, the nation-state cyber warfare landscape, and how AI is shifting security from reactive to proactive defense. They cover the technical details of malware analysis, the economics of vulnerability detection, and the broader implications as both defenders and attackers gain access to increasingly powerful AI tools. –Full transcript available here: https://www.complexsystemspodcast.com/machine-learning-meets-malware-with-caleb-fenton/–Sponsor:  MercuryThis episode is brought to you by Mercury, the fintech trusted by 200K+ companies — from first milestones to running complex systems. Mercury offers banking that truly understands startups and scales with them. Start today at Mercury.com Mercury is a financial technology company, not a bank. Banking services provided by Choice Financial Group, Column N.A., and Evolve Bank & Trust; Members FDIC.–Links:Delphos Labs: https://delphoslabs.com/ Virus Total: https://www.virustotal.com/gui/home/upload “Thel fraud supply chain”, Bits about Money https://www.bitsaboutmoney.com/archive/the-fraud-supply-chain/ –Timestamps:(00:00) Intro(01:20) Understanding software reversing(03:52) The role of AI in software security(06:12) Nation-state cyber warfare(09:33) The future of digital warfare(16:45) Sponsor: Mercury(17:49) Reverse engineering techniques(30:15) AI's impact on reverse engineering(41:45) The importance of urgency in security alerts(42:47) The future of reverse engineering(43:21) Challenges in security product development(44:46) AI in vulnerability detection(46:09) The evolution of AI models(48:06) Reasoning models and their impact(49:06) AI in software security(49:49) The role of linters in security(57:38) AI's impact on various fields(01:02:42) AI in education and skill acquisition(01:08:51) The future of AI in security and beyond(01:12:43) The adversarial nature of AI in security(01:19:46) Wrap

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• How to negotiate your salary package

  In this episode, Patrick McKenzie (patio11) revisits his widely-shared negotiation essay, which he notes may be the most impactful thing he's done in his career aside from VaccinateCA. The essay covers the psychology and tactics of salary negotiation, emphasizing that engineers have turned being bad at negotiation into a "perverse badge of virtue" and that the financial stakes are enormous—a small salary increase compounds over decades to six-figure differences. Patrick walks through practical advice including never giving a number first, understanding how employers actually think about compensation costs, and reframing negotiation as a professional business discussion rather than something morally questionable. –Full transcript available here:www.complexsystemspodcast.com/how-to-negotiate-your-salary-package/–Sponsor:  MercuryThis episode is brought to you by Mercury, the fintech trusted by 200K+ companies — from first milestones to running complex systems. Mercury offers banking that truly understands startups and scales with them. Start today at Mercury.com Mercury is a financial technology company, not a bank. Banking services provided by Choice Financial Group, Column N.A., and Evolve Bank & Trust; Members FDIC.–Recommended in this episode:Patrick’s essay Salary Negotiation: Make More Money, Be More Valued: https://www.kalzumeus.com/2012/01/23/salary-negotiation/ –Timestamps:(00:00) Intro(03:25) Why negotiation matters(05:21) Shifting your mindset to embrace negotiation(06:49) Your counterparty does not share your mental model of negotiation(12:46) Your negotiation started before you applied to this job(17:21) When does a salary negotiation happen?(19:38) Sponsor: Mercury(23:16) The first rule is what everyone tells you it is: never give a number first(28:45) Listen to what people tell you. Repeat it back to them.(33:22) Research, research, research(37:13) New information is valuable and can be traded for things you want(41:20) You have a multi-dimensional preference set. Use it.(44:08:) For your further perusal

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• The capitalist's guide to podcasting, with Ross Rheingans-Yoo

  In this episode, Patrick McKenzie (patio11) and returning guest Ross Rheingans-Yoo discuss the strategic advantages of starting a podcast, particularly for professionals seeking to build trust, expand their networks, and support fundraising efforts. They explore the nuts and bolts of podcast production models, recording logistics, transcript creation, and how to make the experience frictionless for high-value guests. Ross shares his thought process around his newly-launched show Development and Research while Patrick gives a behind the scenes look at the makings of Complex Systems. –Full transcript available here: https://www.complexsystemspodcast.com/capitalists-guide-to-podcasting-with-ross-rheingans-yoo–Sponsor:  MercuryThis episode is brought to you by Mercury, the fintech trusted by 200K+ companies — from first milestones to running complex systems. Mercury offers banking that truly understands startups and scales with them. Start today at Mercury.com Mercury is a financial technology company, not a bank. Banking services provided by Choice Financial Group, Column N.A., and Evolve Bank & Trust; Members FDIC.–Recommended in this episode:Development and Research Podcast: https://developmentandresearch.bio/ Podcast Twitter feed: @DevAndResearchRoss & Ricki’s Trading Bootcamp June 3-5: https://trading.camp/complex Ross' first appearance on Complex Systems: https://open.spotify.com/episode/4GiO0KYqxJNCIdltCyhN6mRicki Heicklen on Complex Systems (our first episode!): https://open.spotify.com/episode/11kEUYRn4gXZGju232hzcg–Timestamps:(00:00) Intro(01:18) The power of podcasting for venture capitalists(03:09) Building trust through voice (07:11) Podcast production models (16:38) Recording and equipment essentials (23:05) Sponsor: Mercury (24:18) Post-production and transcripts (32:22) Advertising vs. User experience (33:28) Creating standalone artifacts (34:20) The power of video clips (35:22) Challenges in podcast distribution (42:12) The role of guests in podcasts (47:12) Pre-recording preparation (49:22) Recording session best practices (54:22) The value of silence in conversations (56:38) Launching and growing a podcast (59:18) Trading bootcamp (1:02:27) Wrap

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