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Participants:

Gary Sheng & Yash Chitneni - AI Writing Workshop at Gauntlet AI

July 12, 2025 - Austin, Texas​

Event Overview​

Gary Sheng conducted a workshop titled "Supercharging Your Writing with AI" for Gauntlet AI Cohort 2 at their Austin office, with Yash Chitneni serving as the primary demonstration subject. The workshop showcased practical AI-assisted writing techniques using Cursor and voice transcription tools.

Key Participants​

  • Gary Sheng: Workshop leader, former Google engineer, AI writing expert
  • Yash Chitneni: Primary participant, CEO of Seren Pods, Gauntlet AI Cohort 2 member
  • Ash Tilawat: Gauntlet AI Head of Product (booked the workshop)
  • Audience: Gauntlet AI Cohort 2 participants (~65 people)

Workshop Content & Methodology​

Gary's Background & Credibility​

Gary established his credentials early: "I started my career at Google after Duke University in 2015. It was a pretty good experience, but it was very slow. A lot of you have done legacy software engineering, and it's a completely different experience. It's harder to get into flow state."

He emphasized his transformation: "Cursor caught my attention last year. I couldn't help but just see what I could do, and started building little apps with it. Eventually saw Austin's tweet, and decided to sign up. It was a really, really great decision."

Core Writing Philosophy​

Gary outlined his fundamental approach: "There's basically, in my view, only one way, one approach to writing with AI that makes any sense. I'm sure you've heard of the distinction between, or at least the clarification of, from prompt engineering to context engineering."

Essential Context Elements for AI Writing:

  • Audience understanding
  • Tone specification
  • Relevant existing literature
  • Primary evidence and inspiration
  • Past writing samples (especially best work)

The Voice-to-AI Process​

Gary demonstrated his preferred methodology: "What I'll do, like, if I have something that is from my heart that I want to express, now I've gotten pretty good at, like, just talking to myself. Or, if I really need to, I'll put on grok voice mode and just talk in grok voice mode for like 30 minutes. Get the transcript and just be like, this is my root context."

Yash's Content Development Session​

The "Doors and Windows" Concept​

Yash introduced his core metaphor: "The doors you open in life lead you to the windows of opportunities. You have to open the door to see what's on the other side, and we're kind of going to flesh it all out."

Olympic National Park Inspiration: "Last year I went to this place at Olympic National Park. This is a hole in the wall, and you can only get to this place at a very specific time because the tide does not allow you to get to this point any other time of the day. There's only a very small window at which the tide is low enough for you to walk through this space."

Personal Philosophy on Timing​

Yash connected this to his Gauntlet experience: "65 plus of us are here in this next seven weeks, and it is a window of opportunity to change the direction of our lives, go in a whole new space, and to show up and maximize what this window looks like is down to us opening the doors that are available and being ready for that moment."

The Serendipity Creation Framework​

On Creating Opportunities: "I think A, it falls under this mission that I have of creating serendipity, and serendipity to me is, you know, first part of that is following curiosity and realizing that you have to keep following that to the point that there's going to be a moment that shows up that you have to stay ready where it's going to change trajectories."

On Timing and Readiness: "If I waited a year, I would probably say now I am not the person opening that door for the first time to be able to carve out what it looks like past it. So it feels that I could wait a year and there's more things mapped out and I can learn easier, but learning I think comes at a better rate and speed when you put yourself at the threshold of it."

Strategic Insights on Content Creation​

Social Media as Door Creator​

Gary probed deeper: "Is part of your philosophy that social media creates new doors?"

Yash confirmed: "Most definitely. Social media allows us to get to the point which is a great equalizer of that. I get to have conversations with people that I never would and it also creates the dynamic of perceptions."

The Win-Win Content Strategy​

Yash's Community-First Approach: "Part of my purpose is to shine a light on as many people here as possible because it's the opposite of a zero-sum game, you know? The more that you shine a light on every person who's individually dealing... My goal is to not only learn in this moment, but to be able to show that, you know, there's all these rock stars, and that helps, you know, put light on them, and it helps me too at the end of the day."

Gary's Positioning Assessment​

Gary recognized Yash's potential: "I feel like if I were to just kind of riff on... You're like, you're literally like, you're like a very inviting person that's like, you can do this too. You can also change your life. We're not gatekeeping the process of changing our lives. I think that you're a great communicator. I think that you're not pretentious about it."

Strategic Positioning Insight: "If I were to say, besides following the Gauntlet account, you're positioning yourself to be like the one account that anyone needs to follow, because you're going to tag other people too, right? It's like a, you know, is this resonating?"

Practical AI Writing Demonstration​

The Cursor Process​

Gary walked through the technical implementation:

  1. Context Setting: "What you're going to do is open up a cursor repo. And then how would you give context to cursor about what you're trying to do?"

  2. Voice Transcription: Using Apple Voice Recorder for automatic transcription: "The nice thing about Apple Voice Recorder is it automatically transcribes, so you don't have to go through another service."

  3. Iterative Refinement: "Don't accept the first drafts. Keep drilling at it with manual typing, and also you can just chat with your essays now, right? That's a thing."

Technical Advantages​

Cursor's Diff System: "If you do one comment about how you want it changed, you can see seven diffs. You can accept, reject, right? That level of granularity is very important."

Context Accumulation: "I have a repo where I basically do all my writing, and it just... Every new piece of writing is there, because that's where I'm drafting it and editing it to the point of completion. And so it's always being able to reference all of the writing that I have."

Community Building & Knowledge Sharing​

The Daily Insight Framework​

Yash's Practical Advice: "The easiest formula with us going through Gauntlet and becoming AI engineers is reflect on what was the most challenging thing that you went through today and what was your discovery pattern of that. And then try and just relay that back in as elementary terms as possible."

Value Proposition: "Because the eyeballs that we currently have on X, on Twitter, is just that these guys in this cohort, in this environment are pushing the boundaries of what we can do with AI. And I get to look at them and I'm interested in wanting to learn from them by following them, by specifically the insights that they give."

Gary's Encouragement for Content Creation​

The Importance of Demonstrating Knowledge: "You are getting a great vibe AI-first engineering education right now with Ash. And I just wanted, this is like something that it's not hard to learn, but it's totally life-changing. Because demonstrating your knowledge about something is valuable forever. Forever."

On Unique Experiences: "Communicating something that reflects your unique experiences, that is locked in your head, but just often just needs one person that kind of gets it as well, but can kind of drill in with you. That's a lifelong skill."

Workshop Outcomes & Insights​

AI Writing Effectiveness Assessment​

Gary distinguished between different types of content: "This is my personal preference, but for like Naval length tweets, let's say, it just comes from the gut for me. And I'll vibe check it with a couple friends before I post it. From my experience, AI sucks at those Naval one-liner type things. For longer form, it's excellent in speeding up the process of creating a really good blog post."

The Embodiment Strategy​

Gary's Strategic Insight: "The world is waiting for this, essentially. For you to create the best version of this because it's reminding people about this law of Zeitgeist Universe, about content and success and serendipity flywheels that they don't have to abstractly wonder how that's happening. You are the embodiment. You are an embodiment that is surrounded by embodiments."

Community Offer​

Yash's Collaborative Approach: "For those of you that don't know, I've got a walking pad at my desk. And if one of you guys are like, yeah, I wanted to talk a lot today and get some ideas flowing, I'm willing to, if you guys want to take the walking pad and put it at your desk, welcome to come grab it and use it."

Key Takeaways & Principles​

Context Engineering Over Prompt Engineering​

  • Voice transcription provides authentic, detailed context
  • Historical writing samples improve AI output quality
  • Specific audience and tone guidance essential

The 15-Minute Content Creation Formula​

  • 5 minutes of voice conversation/interrogation
  • 10 minutes of AI-assisted editing in Cursor
  • Results in content that would otherwise take "infinite time or never happen"

Social Media as Infrastructure​

  • Platforms create new opportunities and connections
  • Consistent sharing builds expertise demonstration
  • Win-win approaches scale better than zero-sum thinking

The Serendipity Creation System​

  1. Follow curiosity consistently
  2. Stay ready for transformative moments
  3. Expand surface area through content creation
  4. Build community through highlighting others

Community-First Growth Strategy​

  • Shine light on others to create mutual benefit
  • Document learning journey for others following similar paths
  • Position as connector and amplifier, not just individual expert

Workshop Impact & Future Implications​

The workshop demonstrated how AI tools can democratize high-quality content creation when combined with authentic voice and strategic thinking. Yash's approach of creating serendipity through intentional content creation, combined with Gary's technical methodology, provides a replicable framework for the Gauntlet AI community to build their expertise and audience simultaneously.

The session highlighted the importance of timing, readiness, and community-first approaches in leveraging AI tools for both personal growth and ecosystem building. The practical demonstration showed how voice-to-AI workflows can transform scattered thoughts into structured, publishable content in minutes rather than hours or days.