Gritty Startups and AI’s Billion-dollar Bets

Hello, and happy Sunday! In anticipation of back-to-school season, we’ve been prepping for our new course, How to Write With AI, that Evan Armstrong will be teaching starting on September 19. Our cohort of nearly 60 students includes executives from companies like Netflix, Midjourney, and leading AI startups. There’s still time to enroll, so check out the course website for more information. In the meantime, read on for everything we published last week and our take on the latest tech news.—Kate Lee

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Knowledge base

🔏 "Welcome to the Era of the Gritty Startup" by Evan Armstrong/Napkin Math: The age of gluttonous startups is over, and we're entering the era of grit. With venture capital funding drying up and growth slowing, it's time for a new breed of startups. Evan outlines three lessons from the past (hint: stock-based compensation isn't free money) and paints a picture of the future: smaller teams, bigger visions, and a focus on cash flow. Read this if you want to build a startup that can thrive in leaner times.

"OpenAI's New Model, Strawberry, Explained" by Dan Shipper/Chain of Thought: ChatGPT is famous for being unable to count the "r"s in "strawberry." OpenAI's latest model, Strawberry, might just solve that conundrum. It's trained on step-by-step reasoning, potentially making it smarter than your average AI bear. Read this if you want to understand why your next chat with ChatGPT might feel more like talking to a math whiz than a lucky guesser.

"Benevolent Billionaire or Despot—Or Both?" by Evan Armstrong/Napkin Math: Properly judging Bill Gates entails balancing his Jeffrey Epstein connections with his saving millions of lives with his philanthropy—the moral math gets complicated, fast. Evan reviews a new book that attempts to profile Gates. Read this for a thought-provoking look at the ethics of extreme wealth and why billionaires might represent a kind of moral singularity beyond our usual frameworks.

🎧 “The Browser Company Is Building a Brand That Drives Viral Growth" by Dan Shipper/Chain of Thought: The Browser Company's head of storytelling, Nashilu Mouen-Makoua, reveals how she’s using AI to build a brand that doesn’t feel like a brand with the Arc browser. From hosting keynotes in diners to using ChatGPT for research, Nash shares her playbook for creating authentic narratives that resonate beyond Silicon Valley. 🎧 Watch on X or YouTube, or listen on Spotify or Apple Podcasts. Subscribers have access to the full transcript. 

🔏 "Inside the Pod: Can AI Solve the Adult Friendship Problem?" by Rhea Purohit/Chain of Thought: If you’ve been feeling lonely, AI may be able to help. New York Times columnist Kevin Roose made 18 new friends—with AI companions. His experiment reveals the potential and pitfalls of digital friendships, whether getting parenting advice or fit checks. Read this for a glimpse into the future of social connections and to learn how a tech expert uses AI in his daily life and work.