3 founder playbooks + 7 wild headlines = one ruthless VC prompt

Hi ,

I spend a shocking amount of time writing things for LinkedIn that occasionally gets likes.

linkedin.com/in/estesryan

I will occasionally like your stuff too.

Let’s dive in.

This week from the AI for Founders podcast on Spotify:

How SmartLab Builds STEM Identity LINK
Jennifer Berry shows how SmartLab turns classrooms into hands-on ecosystems that manufacture “aha moments” and build future-ready students with STEM identity.

Privacy-First Computer Vision with Galvin Widjaja LINK
From running restaurants to building Lauretta.io, Galvin explains how empathy-first leadership drives privacy-first AI trusted by the U.S. government.

Building Secure AI Foundations with Ben Wilcox LINK
ProArch CTO/CISO Ben Wilcox breaks down compliance-first scaling, Microsoft Copilot realities, and how to adopt AI without blowing up security.

Tip of the spear:

OpenAI Wants to Predict Your Age LINK
OpenAI is experimenting with models that can estimate human age, sparking privacy debates about how such data could be used.

Meta’s Next Ray-Bans Get Smarter LINK
Meta is rolling out smart glasses with built-in displays in partnership with Ray-Ban and Oakley, aiming to make wearables mainstream.

Google Pushes Agent-Driven Shopping LINK
Google has launched a protocol that lets AI agents make purchases directly on users’ behalf, raising new questions about trust and control.

YouTube Creators to Get Bigger Payouts LINK
YouTube is hiking creator payments as competition for talent intensifies across TikTok, Instagram, and Twitch.

Used EVs Now Cheaper Than Gas Cars LINK
For the first time, used electric vehicles are selling for less than comparable gas-powered cars, flipping the market script.

Nepal’s Political Crisis Spills Into Discord LINK
Nepal’s unfolding political crisis has bizarrely migrated to Discord, where protests and debates are playing out in real time.

Musk Eyes Starlink as a Global Carrier LINK
Elon Musk is considering turning Starlink into a full global telecom carrier after a major deal with EchoStar.

Prompt of the week:

Role-play as a skeptical venture capitalist reviewing my business. Your job is to tear apart my business model with brutal honesty, highlighting every weak point, hidden assumption, and risk that would make you hesitate to invest. Be direct and adversarial, not polite. Specifically:

• Question my revenue model, pricing, and scalability.

• Challenge my customer acquisition strategy and distribution channels.

• Push back on my competitive moat and differentiation.

• Stress-test my financial projections and funding plan.

• Identify regulatory, operational, or team risks I may be overlooking.
  End by listing the top 5 objections you would bring up in a pitch meeting that could kill the deal. Assume I will defend myself, so make the objections sharp and detailed.

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Keep it moving

Tesla Stock Rockets Back LINK
Tesla has erased its yearly losses, surging over 80% since April’s low on renewed investor optimism.

Robinhood Opens Startup Investing to All LINK
Robinhood is planning a fund that lets everyday investors put money into startups, democratizing access to venture-style bets.

Gemini Beats ChatGPT on iPhones LINK
Google’s Gemini has overtaken ChatGPT as the top free iPhone app, signaling a power shift in the AI app wars.

Senior Devs Become AI Babysitters LINK
Vibe coding is forcing senior developers to babysit AI-generated code, but many say the tradeoff is worth the speed.

Models Can Prompt Themselves LINK
Researchers are showing how AI models can generate their own prompts, raising both efficiency and safety concerns.

Ant Group Unveils Tesla Bot Rival LINK
China’s Ant Group has revealed its own humanoid robot, directly challenging Tesla’s Optimus in the race for consumer robots.

Microsoft and OpenAI Double Down LINK
Microsoft and OpenAI announced the next phase of their partnership, hinting at deeper integration of AI into Windows and Office.

Google Kills Its Airtable Clone LINK
Google is shutting down Tables, its Airtable competitor, leaving users scrambling for alternatives.

Claude Gets a Memory Upgrade LINK
Anthropic’s Claude can now remember past interactions, making workflows smoother for businesses and teams.

Code Story Podcast: It’s like therapy for startup founders, except the therapist is a microphone and everyone’s listening. Code, chaos, and confessions served weekly.

What I’m thinking about:

• What if your biggest success came from a total collapse? Interview

• Give people their flowers when they earn them. Interview

• The Founder Challenge Quiz Survey

Uncover the AI tools (here) you didn’t ask for, but now you’re weirdly into.

Thanks for being here.

-Ryan

p.s. When you are ready, here’s how I can help.

We have successfully booked podcast interviews for over 800 funded startup founders, entrepreneurs with exits, and C-suite executives. If you're ready to lead your company from the front, let Kitcaster handle your podcast scheduling and create a powerful stream of content for you and your brand.

I write about Revops, Product, and Founder-led marketing on Linkedin, Twitter, and my blog.