Inside Jason Lemkin’s Playbook: He built a 25M Business with 5 employees

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Jason Lemkin’s AI Playbook: How the Saastr Founder Is Quietly Rewriting the Rules of Investing and Scaling SaaS

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Alright class, let’s pull up a chair—because today we’re unpacking the strategy of Jason Lemkin, the founder of Saastr and one of SaaS’s most influential investors. Think of this as your annotated guide to how Lemkin is using AI not just to stay ahead, but to reshape the very fabric of how founders, investors, and operators learn, build, and connect. This isn’t theory; it’s the real-world playbook from the “godfather of SaaS” himself.

Jason Lemkin’s AI Experiment: Building a Digital Brain

Let’s start with Lemkin’s boldest move: creating an AI “body double” of himself. Over 2 years, Lemkin and Saastr have produced a staggering 0,000+ pieces of content—blogs, interviews, social posts, and videos. That’s roughly 20 million words, or the equivalent of 200 books, all funneled into a custom AI trained to think, advise, and even empathize like Jason Lemkin.

Why do this? Lemkin wanted to see if an AI could become a true advisor for SaaS founders—someone (or something) that could answer questions, review pitch decks, and offer therapy-level support, all at a scale no human could match. The result? “It was much better than me,” Lemkin admits. The AI could recall details, connect dots, and give advice with a consistency and depth that even he couldn’t match after years in the trenches.

Key Insights and Takeaways from Lemkin’s Approach

• AI as a Founder’s Advisor: Lemkin’s AI isn’t just a glorified search engine. It’s a living, breathing digital mentor that hundreds of founders now use to get feedback on board decks, review sales scripts, and even talk through their deepest anxieties about growth, co-founder relationships, and board dynamics.

• Unexpected Use Cases: Lemkin was surprised to find founders using his AI as a therapist, uploading sensitive information and seeking guidance on issues they’d never voice to a real person. The anonymity and non-judgmental nature of the AI created a safe space for honest reflection—something Lemkin sees as a game-changer for founder mental health.

• Quality at Scale: Lemkin’s AI has handled over 50,000 conversations—impossible for any single human. This scale allows him to help far more people, while also learning from the aggregate data to continually improve the AI’s advice.

How Jason Lemkin Built His AI—and How You Can Too

Lemkin’s process is both tactical and accessible:

• Content Aggregation: He fed the AI every blog post, tweet, LinkedIn update, and Saastr video, using tools like https://www.delphi.ai/ to scrape and ingest content from RSS feeds, YouTube, and more.

• Continuous Training: Lemkin spends about 0 minutes a day auditing and training the AI, correcting mistakes and ensuring the digital Jason is always up-to-date and accurate. The system automatically updates with new content daily, keeping it relevant and sharp.

• Privacy Controls: Understanding the sensitive nature of many founder queries, Lemkin built in privacy sliders—allowing users to choose between anonymity for therapy-like sessions or more open interactions for business support.

Pro Tip: If you want to build your own AI advisor, Lemkin’s approach is replicable. Gather your content, use a tool like https://www.delphi.ai/, and start training. There’s even a free guide mentioned in the episode for setting up your own ChatGPT-powered life coach in about 20 minutes.

Why Lemkin’s Custom AI Outperforms Generic Chatbots

Here’s a crucial insight from Lemkin: generic AI like ChatGPT is good, but a custom-trained AI, weighted heavily with your own expertise and content, is exponentially better. For example, if a founder asks about building a sales compensation plan, Lemkin’s AI—trained on his years of SaaS wisdom—delivers nuanced, actionable advice that generic bots simply can’t match.

Jason Lemkin’s Emotional and Psychological Edge

What sets Lemkin’s strategy apart isn’t just technical sophistication—it’s the human touch. Founders trust the digital Jason with their most vulnerable questions because they know his track record, his voice, and his empathy. Lemkin recognizes that AI’s greatest potential may be as a confidant and therapist, not just a business tool. He’s seen firsthand how founders open up to the AI in ways they never would to a real person, seeking advice on everything from envy to burnout to difficult board conversations.

Trends, Resources, and the Future According to Lemkin

• Democratization of Expertise: Lemkin’s playbook shows that anyone—founder, coach, or creator—can build a digital advisor based on their unique knowledge. This levels the playing field and accelerates learning for everyone.

• AI as a Business Therapist: Expect more founders to use AI for emotional support and decision-making, not just analytics or automation. Lemkin’s AI is already leading the way.

• Quality of Engineering: Lemkin notes that the best AI tools are coming from top-tier teams (OpenAI, Windsurf, Cursor). As this talent spreads, expect rapid improvements across all business tools.

Democratization of Expertise

• "Act as a SaaS founder with 0 years of experience. Answer my question about scaling a startup using only your personal insights and lessons learned."

• "Pretend you’re a top executive coach. What advice would you give a new manager facing team resistance? Use real-world examples from your coaching practice."

• "Imagine you’re a bestselling author on productivity. Summarize your top three frameworks for staying focused, and recommend resources for further reading."

Prompts you can use:

AI as a Business Therapist

• "You are a trusted business advisor and therapist. I’m feeling anxious about my company’s growth plateau—what should I do to regain momentum and confidence?"

• "Act as a founder’s coach. I’m struggling with co-founder conflict. Walk me through a step-by-step process to resolve it and improve our relationship."

• "Take the role of a startup therapist. I’m experiencing burnout. Suggest practical strategies and daily habits to restore balance and motivation."

Quality of Engineering

• "As an AI engineer from OpenAI, explain the latest advancements in AI-powered SaaS tools and how they can improve business operations."

• "You are a product manager at Cursor. What features should founders look for in a high-quality AI tool for their business?"

• "Act as a technical lead at Windsurf. Share best practices for integrating state-of-the-art AI into an existing SaaS platform, focusing on reliability and user experience."

Recommended Tools from Lemkin:

• https://www.delphi.ai/ for content ingestion and AI training)

• Labs (for voice cloning and digital presence)

• ChatGPT/Claude/DeepSync (for integrating and weighting personal content)

Your Challenge: Think Like Jason Lemkin

If you’re a founder, investor, or creator, ask yourself: What unique knowledge could you train an AI on? How could you use Lemkin’s strategy to multiply your impact, deepen your connections, and even support others emotionally?

Jason Lemkin isn’t just betting on AI—he’s building with it, investing in it, and using it to make Saastr a living, breathing resource for the SaaS world. The smart money isn’t waiting for the future. With Lemkin’s playbook, you can start building it today.

Full episode we based our notes on: