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.
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Full transcript: www.complexsystemspodcast.com/getting-better-at-llms-with-zvi-mowshowitz/

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Sponsor:  Vanta

Vanta automates security compliance and builds trust, helping companies streamline ISO, SOC 2, and AI framework certifications. Learn more at https://vanta.com/complex

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Links:

• Don’t Worry About the Vase https://thezvi.wordpress.com/ 

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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

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.
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Full transcript available here: https://www.complexsystemspodcast.com/machine-learning-meets-malware-with-caleb-fenton/

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Sponsor:  Mercury

This 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.
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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/ 

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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

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.

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Full transcript available here:
www.complexsystemspodcast.com/how-to-negotiate-your-salary-package/

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Sponsor:  Mercury

This 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.
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Recommended in this episode:

• Patrick’s essay Salary Negotiation: Make More Money, Be More Valued: https://www.kalzumeus.com/2012/01/23/salary-negotiation/ 

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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

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.

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Full transcript available here: https://www.complexsystemspodcast.com/capitalists-guide-to-podcasting-with-ross-rheingans-yoo

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Sponsor:  Mercury

This 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.

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Recommended in this episode:

• Development and Research Podcast: https://developmentandresearch.bio/ 
• Podcast Twitter feed: @DevAndResearch
• Ross & Ricki’s Trading Bootcamp June 3-5: https://trading.camp/complex 
• Ross' first appearance on Complex Systems: https://open.spotify.com/episode/4GiO0KYqxJNCIdltCyhN6m
• Ricki Heicklen on Complex Systems (our first episode!): https://open.spotify.com/episode/11kEUYRn4gXZGju232hzcg

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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

In this episode, Patrick McKenzie (patio11) is joined by Jacob Swett of Blueprint Biosecurity to discuss far UVC technology - a specialized wavelength of UV light that kills airborne pathogens while remaining safe for humans. Jacob explains how widespread deployment of this technology in schools, hospitals, and public spaces could dramatically reduce respiratory diseases and prevent future pandemics, comparing our approach to air quality with the water sanitation revolution that eliminated diseases like typhoid. They discuss the economics of implementation (starting around $30 per student annually with costs likely decreasing), the historical reasons why this technology hasn't been widely deployed, and Blueprint Biosecurity's roadmap for increasing adoption from early users to eventual regulations similar to fire safety codes.

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Full transcript available here: https://www.complexsystemspodcast.com/killing-viruses-with-light-with-jacob-swett/ 

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Sponsor:  Mercury

This 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.

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Recommended in this episode: 

• Blueprint Report: https://blueprintbiosecurity.org/u/2025/03/Blueprint-for-Far-UVC-PREPRINTv1.0.pdf 

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Timestamps:
(00:00) Intro

(00:31) The importance of indoor air quality

(01:29) Technologies for cleaner air

(02:31) The promise of Far-UVC

(03:10) Impact of COVID-19 on air quality awareness

(04:11) Understanding Far-UVC light

(06:44) Applications and benefits of Far-UVC

(16:42) Challenges and adoption of Far-UVC

(20:40) Sponsor: Mercury

(21:53) Challenges and adoption of Far-UVC (Part 2)

(23:19) Cost and benefits of Far-UVC

(26:40) The broader impact of respiratory pathogens

(29:41) Rediscovering the world for better health

(30:05) Historical perspectives on infectious diseases

(30:57) The role of sanitation and antibiotics

(33:02) Miasma theory and airborne transmission

(34:59) Impact of World War II on disease research

(38:06) The evolution of public health priorities

(42:39) Future of Far-UVC Technology

(46:03) Challenges in implementing Far-UVC

(56:47) The importance of rigorous studies

(01:00:33) Wrap

In this episode, Patrick McKenzie (patio11) is joined by Zac Townsend, a serial founder and CEO of Meanwhile, a fully regulated life insurance company operating in Bitcoin. They explore the differences between life and property insurance, explain why term life is essential financial protection everyone should consider, and dive into the tax benefits that shape the industry. Zac shares insights on how private equity firms are acquiring insurers for their stable capital base, and explains Bermuda's role as the world's insurance capital.

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Full transcript available here: https://www.complexsystemspodcast.com/life-insurance-and-your-money-with-zac-townsend/

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Sponsor:  Mercury

This 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.

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Recommended in this episode:

• Meanwhile https://meanwhile.bm/

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Timestamps:

(00:00) Intro

(00:23) Overview of Meanwhile Insurance

(00:56) How Bitcoin is being used in the insurance industry

(02:12) Understanding different types of insurance

(06:13) Term life insurance explained

(07:26) Life insurance tips for tech professionals

(12:47) Permanent life insurance and annuities

(18:57) Sponsor: Mercury

(20:11) Insurance regulatory insights

(25:46) Principal-agent problems in insurance

(37:09) Tax considerations in life insurance

(42:16) Leveraging life insurance for estate planning

(44:55) Premium financing explained

(47:39) Wealth management and market segmentation

(52:09) Regulatory challenges and mispricing in insurance

(01:03:32) Reinsurance and the role of bermuda

(01:10:27) Private equity's interest in insurance

(01:14:24) Building a crypto life insurance company

(01:20:02) Wrap

In this episode, Patrick McKenzie (@patio11) is joined by Mikey Dickerson to discuss the complex realities behind government software projects. Mikey shares insights from leading the healthcare.gov rescue effort and founding the United States Digital Service, explaining how procurement processes create requirements through committee decision-making without market-based feedback loops. They explore how government systems handle software development differently than industry, with Mikey noting that the issues are less about individual competence and more about systemic incentives that reward risk aversion. The conversation covers the challenges of "modernization" efforts, the loss of organizational management knowledge over decades, and reflection on when and how technologists might effectively contribute to public service.

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Full transcript available here: https://www.complexsystemspodcast.com/episodes/fixing-government-technology-with-mikey-dickerson/

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Sponsor:  Mercury

This 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.

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Recommended in this episode:
www.complexsystemspodcast.com/fixing-government-technology-with-mikey-dickerson/

• Bureaucracy by James Q. Wilson: https://www.amazon.com/Bureaucracy-Government-Agencies-Basic-Classics/dp/0465007856 
• Movie: The Pentagon Wars https://en.wikipedia.org/wiki/The_Pentagon_Wars 
• Mikey Dickerson's company Layer Aleph: https://layeraleph.com/ 
• Complex Systems with Dan Davies https://open.spotify.com/episode/5QKxzgumJXSQuaWCmYAoM9?si=uQWgAx1iSzGm5iCUBWei8A 
• Complex Systems with Dave Guarino https://open.spotify.com/episode/0UlTIRosmjtvpcdHQ7t2tK?si=MlUqO3uWRie1E_GRQ5D7jg 

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Timestamps:

(00:00) Intro

(00:24) Government software procurement

(06:02) Fighter planes and requirements

(08:37) Software development cycles

(11:37) Deadline challenges

(12:18) California vaccine scheduling

(16:15) Pandemic priorities

(17:27) Sponsor: Mercury

(18:40) Government employee competence

(22:30) Government pay scales

(25:56) IRS modernization reports
(27:48) System modernization plans

(34:33) Healthcare.gov lessons

(36:59) Government software capability

(40:29) Feedback loops in civil service

(44:09) Legislative expertise

(46:49) Applied mathematics

(47:57) Loss of knowledge

(49:28) Tour of duty recommendation

(53:06) Wrap

In this episode, Patrick McKenzie (@patio11) is joined by Daniel Golliher, founder of Maximum New York, to discuss the opaque mechanics of political power and how everyday people can effectively engage with government systems. They explore the stark gap between formal political science degrees and how politics actually works, practical tactics for influencing policy (like optimizing the printability of a blog post to placing well-timed calls to legislators), and Daniel’s concept of ‘blue tape’. Throughout the conversation, they emphasize that participating in governance requires far less expertise and connections than most people assume—mainly just the willingness to show up prepared.

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Full transcript available here:
www.complexsystemspodcast.com/understanding-and-wielding-power-in-local-government-with-daniel-golliher/

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Sponsor:  Vanta

Vanta automates security compliance and builds trust, helping companies streamline ISO, SOC 2, and AI framework certifications. Learn more at https://vanta.com/complex

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Recommended in this episode:

• Daniel Golliher’s essay: Political Science Degrees Must End: https://www.maximumnewyork.com/p/political-science-degrees 
• Patrick McKenzie: https://worksinprogress.co/issue/the-story-of-vaccinateca/ 
• Statecraft by Santi Ruiz: https://www.statecraft.pub/ 

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Timestamps

(00:00) Intro
(00:33) The reality of political science education
(02:45) The apprenticeship model in government
(04:24) Challenges in government training
(07:06) The role of legislative aides
(10:33) Local government and housing policies
(14:24) Effective political engagement
(16:15) The power of communication in policy
(20:26) Sponsor: Vanta
(21:44) Witnessing government in action
(31:29) Learning government and politics
(32:21) LLMs and policy
(35:10) Engaging with local politics
(37:58) Influencing policy
(43:25) Running for office
(47:10) Blue tape
(58:39) Wrap

In this episode, Patrick McKenzie (@patio11) is joined by Tim Fist, Director of Emerging Technologies at the Institute for Progress, to discuss how energy constraints could bottleneck AI development. They explore how AI training clusters will soon require gigawatts of power—equivalent to multiple nuclear plants—with projections showing a single cluster needing 5 gigawatts by 2030. Tim explains why behind-the-meter generation and geothermal energy offer promising solutions while regulatory hurdles like NEPA and transmission permitting create "litigation doom loops" that threaten America's competitiveness. The conversation covers the global race for compute infrastructure, with China and the UAE making aggressive investments while the US struggles with permitting delays, highlighting how energy policy will determine which nations lead the AI revolution.

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Full transcript available here: www.complexsystemspodcast.com/the-ai-energy-bottleneck-with-tim-fist/
–
Sponsor:  Vanta

Vanta automates security compliance and builds trust, helping companies streamline ISO, SOC 2, and AI framework certifications. Learn more at https://vanta.com/complex

–

Recommended in this episode:

• Compute in America https://ifp.org/compute-in-america/
• Tim Fist on Twitter https://x.com/fiiiiiist 
• The Enchippening by Sarah Constantin https://sarahconstantin.substack.com/p/the-enchippening 
• Solar economics with Casey Handmer https://open.spotify.com/episode/0GHegWgLSubYxvATmbWhQu?si=VKJYaSwaRJq_YcK8kJIdvQ 
• AI & Power economics with Azeem Azhar https://open.spotify.com/episode/3KkvPiYpGvXCRukWxHP7Ch?si=RPEjrs67S9CFA0lLak6OVA
• Fracking with Austin Vernon  https://open.spotify.com/episode/0YDV1XyjUCM2RtuTcBGYH9?si=hSniC3N0QkqhF74ra-XAcA 
• Economics of the grid with Travis Dauwalter https://open.spotify.com/episode/5JY8e84sEXmHFlc8IR2kRb?si=BsqMZGu6Qr-2F7-RSyyEhw

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Timestamps:

(00:00) Intro

(00:40) Energy bottlenecks in AI development

(02:56) Technical and policy solutions for energy needs

(05:18) Challenges in transmission infrastructure

(12:14) Behind the meter generation explained

(17:50) Solar and storage: The future of energy

(18:47) Sponsor: Vanta

(20:05) Solar and storage: The future of energy (part 2)

(29:07) Power purchase agreements and financing

(33:17) Financing geothermal wells

(33:53) The promise of geothermal energy

(35:25) Challenges in geothermal adoption

(36:59) Industrial applications of geothermal heat

(45:01) Geothermal energy and national security

(49:27) Global investments in AI and energy infrastructure

(56:29) Policy and technical expertise in AI

(01:00:54) The role of government in technological advancements

(01:05:07) Wrap

In this episode, Patrick McKenzie (@patio11) is joined by Haseeb Qureshi, a managing partner at Dragonfly, a crypto-focused VC fund. They discuss the evolution of stablecoins, three key use cases, and their impact on international finance. Haseeb explains how stablecoins have grown beyond their initial association with crypto trading and illicit activities to serve legitimate economic functions globally, in ways that many Americans might not fully appreciate. Patrick and Haseeb debate the regulatory landscape, the strategic ambiguity of crypto's positioning, and whether stablecoins represent a parallel financial system that might eventually converge with traditional banking.

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Full transcript available here: www.complexsystemspodcast.com/taking-stablecoins-seriously-with-haseeb-qureshi/

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Sponsor:  Safebase

Ready to save time and close deals faster? Inbound security reviews shouldn’t slow down your team or your sales cycle. Leading companies use SafeBase to eliminate up to 98% of inbound security questionnaires, automate workflows, and accelerate pipeline. Go to safebase.io/podcast 

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Recommended in this episode:

• Zeke Faux on Complex Systems https://open.spotify.com/episode/5OnSK3PuhfipMHv9htvuyb 
• Chopping Block podcast https://unchainedcrypto.com/the-chopping-block/ 
• Haseeb Qureshi’s website https://haseebq.com/about/ 

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Timestamps:
(00:00) Intro

(00:55) Crypto industry insights and tether discussion

(02:52) Stablecoins and their economic models

(05:04) Decentralized stablecoins and their mechanisms

(07:41) VC perspective on stablecoin investments

(13:18) Regulatory challenges and lobbying in crypto

(20:36) Emerging use cases for stablecoins

(24:16) Sponsor: Safebase

(32:35) The initial response to stablecoins

(33:38) Stablecoins and national security concerns

(34:00) The shift in congressional attitude

(34:49) Stablecoins and dollar internationalization

(37:40) Retail payments in high-inflation countries

(38:41) The role of black markets

(46:13) International B2B payments

(01:02:57) The future of stablecoins

(01:05:44) Wrap