Guides

Guides for Going AI-Native

Operator teardowns from the companies I run myself, plus founder playbooks built from real data.

Operator Systems

AI 10 min read

Harness Engineering: The OS Behind 5 Companies

What 200+ AI Engineers Named the Thing I Already Run

In early 2026, engineers from OpenAI, Anthropic, IBM, and Google DeepMind independently described the same discipline: harness engineering — everything around the model that makes an agent reliable. I run five AI-native companies on it with zero hired employees. This is the teardown: the 5 artifacts, the principles, and why the harness is built to be deleted.

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AI 12 min read

How I Run 5 Companies with Zero Hired Employees

The Architecture Teardown

I run a multi-product portfolio company (GameTape, Sena, Precis, TrueStandard, Gavel) with zero employees. This is the actual operating system: the build order, the five primitives that make agents reliable, and the one thing each company replaced that would normally need a team. Architecture, not prompts.

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AI 11 min read

How Much of Your Company Lives in 3 People's Heads?

The Locked-Context Audit

The models are smart enough. The bottleneck is the company-specific context locked in your senior people's heads. Score your company on 9 questions, then get the teardown: the closed loop, the 5 building blocks, the roles a system replaced, and what it ships, across a portfolio run with zero employees (cofounders + agents).

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AI 14 min read

Every Agentic Engineering Hack I Know

10 Patterns From Running 5 AI-Native Companies on Agents

I run five AI-native companies on agents with zero hired employees. These are the ten agentic-engineering hacks that actually hold up in production. Each one I run myself, and each is backed by a builder from the AI Engineer stage who landed on the same pattern independently.

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AI 13 min read

What It Actually Means to Be AI-Native

People, Agents, and Context — From an Operator Who Runs Five Companies on It

Everyone says 'AI-native'; almost nobody means it. The real bar: people manage agents, agents read and write to the company, and the company gets smarter over time. This is the linear teardown of the three layers — people, agents, context — plus the two live workflows that turn the system into speed-to-signal, from an operator who runs five AI-native companies with zero hired employees.

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AI 12 min read

Where to Point AI First: The Function-Selection Playbook

How Mid-Market Companies Choose the Right Workflow to Make AI-Native

Five live operator guides show how to build an AI-native system. None tells you where to aim it. This is the selection layer: the three vectors (industry × function × company size), the frequency × value grid, and the exact rubric I score a workflow with before I build it — drawn from running five AI-native companies with zero hired employees.

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AI 13 min read

What 26,000 Operators Are Actually Asking About AI

The Demand Map — 10 Questions Mined From 26,000 Comments, Answered by an Operator

I mined ~26,000 comments across five AI channels and ranked what people in the trenches actually ask. The catch: they're builders, not buyers — but their loudest frustrations (shipping, cost, security, maintenance) are exactly what stalls AI inside mid-market companies, seen from the other side of the table. This is the demand map: the 10 questions that dominate, the four that kill the deal, and how I answer each one across five companies I run with zero hired employees.

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AI 12 min read

Service-as-a-Software Is the 2026 Model I've Run for Two Years

The Business Model Behind Five Companies, Run With Zero Hired Employees

Everyone's calling "service-as-a-software" the 2026 model: work that ships like a service but runs on software instead of a team. I'm not forecasting it — I've operated five companies this way for two years with zero hired employees. This is the business model from inside it: the three ways to sell work, why the services model breaks, the five companies as five services delivered as software, the four layers it runs on, and what changes to the unit economics when you stop pricing human time — corroborated against 22,319 comments from the AI-native channels I cache and track.

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Founder Playbooks

Business 18 min read

The $100K/Year Side Business Blueprint

Patterns from 100 Founder Stories

We analyzed 143 videos from Starter Story, My First Million, and Greg Isenberg to extract what actually works: business models, revenue milestones, and the strategies founders use to build $100K+ side businesses.

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Business 15 min read

How to Build an AI Automation Agency

The 2025 Playbook

We analyzed 100+ videos from 3 top AI creators to extract what actually works: service offerings that sell, pricing models, tool stacks, and client acquisition strategies.

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Career 18 min read

10 Skills for Thriving in the Age of AI

Insights from 200+ Expert Interviews

We analyzed 200+ interviews on Lenny's Podcast to identify the skills that top product leaders, founders, and executives say matter most as AI transforms every industry.

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Startup 20 min read

How to Get Your First Customers

14 Strategies from 50 Founders

We watched 50 founder interviews on Starter Story and extracted exactly how they got their early users. No theory. Just what worked.

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AI 20 min read

AI Model Selection for Startups

Claude vs GPT vs Gemini: What YC Partners Recommend

We analyzed 47 Y Combinator videos featuring Andrej Karpathy, Sam Altman, Dario Amodei, and other AI leaders to extract practical guidance on which models to use and when.

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AI 18 min read

The Vibe Coding Playbook

Build Apps Without Writing Code

We analyzed 25 videos from Greg Isenberg to extract the vibe coding philosophy: tools that work, shipping strategies, and how non-technical founders are building apps faster than developers.

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Business 16 min read

Rapid Startup Building & Selling

The Side Project Flipper Playbook

We analyzed 18 videos from Greg Isenberg on the philosophy of building and flipping startups fast: ship in days, validate quickly, and sell while momentum is high.

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Marketing 14 min read

GEO: AI Search Optimization

Get Cited by ChatGPT & Perplexity

Get your brand cited by ChatGPT, Perplexity, and Claude. We analyzed 8 videos from Greg Isenberg on the new frontier of search: Generative Engine Optimization.

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Startup 18 min read

Micro-SaaS Marketing Playbook

From Zero to 1,000 Users

We analyzed 49 micro-SaaS founder interviews from Starter Story and extracted the marketing playbooks that actually work. No theory. Just proven tactics from $10K-$400K/month founders.

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Startup 16 min read

App Idea Validation Playbook

Pre-Sell Before You Build

Stop building apps nobody wants. We analyzed 49 micro-SaaS founders from Starter Story to extract how they validated ideas before writing code. The frameworks that reduce startup risk to near zero.

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Product 22 min read

Product Management Frameworks

Lessons from 66 Lenny's Podcast Episodes

We analyzed 66 episodes from Lenny's Podcast to extract 31 frameworks, 12 rules, and 25 principles from the world's top product leaders.

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Leadership 20 min read

Startup Leadership Playbook

19 Frameworks from 67 Expert Interviews

We analyzed 67 expert interviews on Lenny's Podcast to extract 19 leadership frameworks, 7 rules, and 20 principles for founders and leaders.

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Growth 22 min read

Product Growth Playbook

35 Frameworks from Top Growth Leaders

We analyzed 67 episodes from Lenny's Podcast to extract 35 growth frameworks, 20 rules, and 27 principles from elite practitioners like Elena Verna, Sean Ellis, and Sarah Tavel.

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AI 20 min read

AI Agent Deployment Playbook

Lessons from 49 Expert Interviews

We analyzed 49 episodes from Lenny's Podcast and 3,686 comments to extract practical frameworks for deploying AI agents in business. From SaaStr's 20-agent sales team to Intercom's Fin reaching $100M ARR.

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Marketing 18 min read

Answer Engine Optimization (AEO)

Get ChatGPT to Recommend Your Product

Webflow sees 6x higher conversion from LLM traffic. We analyzed Lenny's Podcast episodes with top SEO experts and 3,686 comments to build the definitive AEO playbook for product teams.

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AI 20 min read

The Real Math on AI and Jobs

What 100 a16z Videos and 823 Comments Reveal

We analyzed 100 videos from Andreessen Horowitz and 823 viewer comments to map which jobs AI will displace, what new roles are emerging, and the economic math most people get wrong.

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Business 25 min read

The Solopreneur Playbook

Build a $1M One-Person Business

We analyzed 115 founder interviews from Starter Story and My First Million to extract the systems, habits, and frameworks solopreneurs use to build $1M+ businesses alone.

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Business 25 min read

Scaling to $1M

The Inflection Points That Actually Matter

We analyzed 100+ founder interviews from Starter Story and My First Million to extract the inflection points, frameworks, and decisions that separate $10K businesses from $1M ones.

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AI 22 min read

AI Product Builder's Playbook

From Wrapper to Moat

We analyzed 89 videos from Starter Story and Y Combinator to extract what separates successful AI products from GPT wrappers. Moat strategies, pricing, and distribution — all backed by real founder data.

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Business 25 min read

The Founder's Mental Models

Decision Frameworks from 200+ Interviews

We analyzed 200+ founder interviews from My First Million and Y Combinator to extract the mental models, decision frameworks, and thinking tools top founders use to navigate uncertainty, evaluate risk, and build lasting companies.

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Business 22 min read

Indie App Playbook

Build, Launch, and Monetize a Mobile App

We analyzed 47 indie developer interviews on Starter Story to extract the exact playbooks for building, launching, and monetizing mobile apps as a solo developer. From $12K/month vibe-coded apps to $250K/month one-feature products, here is what actually works.

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Business 22 min read

What 986 Startups With Verified MRR Tell You About What to Build

Niches, Multiples, and Business Models That Actually Work

We scraped 986 startups from TrustMRR with verified revenue through Stripe and RevenueCat. $11.6M in total MRR. 320 founders trying to sell. Here is what the data says about which niches, business models, and pricing strategies actually work.

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Marketing 20 min read

Engineering as Marketing: How Founders Use Free Tools to Drive $10K-$100K MRR

Case Studies and Playbooks from 10+ Founders Who Replaced Paid Ads with Free Tools

We analyzed 10+ founder interviews from Starter Story to extract how they use free tools to drive traffic and revenue. SiteGPT built 50 free tools and gets 50K clicks/month from Google — with zero paid marketing. Here are 6 proven strategies.

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Startup 20 min read

How Many Times Do Solo Founders Fail Before $10K/Month?

Data from 208 Founder Interviews Across 4 Channels

We analyzed 208 founder interviews across StarterStory, TheBrettWay, Steven Cravotta, and Superwall to track how many projects founders ship before hitting $10K/month. 35 founders shared explicit failure counts. The patterns are not what motivational content tells you.

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Marketing 18 min read

The Cold Email Playbook: Tactics from 200+ Founder Interviews

Every Cold Email Tactic That Generated Revenue

We analyzed 200+ founder interviews across StarterStory, TheBrettWay, Steven Cravotta, and Superwall to extract every cold email tactic that actually generated revenue. From Will Cannon's $1M ARR template to Stanley AI's email-as-product-demo approach to Hunter Dickinson's peer group play that scaled to $800M with no marketing team. Eight founders. Eight different approaches. All the numbers.

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