Founder Weekly (Issue 697 August 27 2025)

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Welcome to issue 697 of Founder Weekly. Let's get straight to the links this week.

The future of AI customer service is at Pioneer

There’s only one place where CS leaders at the cutting edge will gather to explore the incredible opportunities presented by AI Agents: Pioneer.

Pioneer is a summit for AI customer service leaders to come together and discuss the trends and trajectory of AI and customer service. You’ll hear from innovators at Anthropic, Toast, Rocket Money, Boston Consulting Group, and more—plus a special guest keynote delivered by Gary Vaynerchuk.

You’ll also get the chance to meet the team behind Fin, the #1 AI Agent for customer service. The whole team will be on site, from Intercom’s PhD AI engineers, to product executives and leaders, and the solutions engineers deploying Fin in the market.

Join Pioneer in-person or online on October 9th, 2025. Register today.

General

Every Reframe Starts with a Refusal

Pattern-breaking founders succeed by refusing the unspoken, limiting conventions that shape industries, thereby reframing how people think and act with bold, contrarian alternatives. This refusal breaks old mental models, captures attention, and creates breakthroughs by replacing accepted "rules" with new, surprising truths that change markets and mindsets.

The $1T Opportunity to Build the Next Amazon in Retail

The next major technology shift set to transform retail is artificial intelligence. This means big opportunities for startups with new ideas.

From LLM Wrappers to RL Sculptors: The Dawn of Reasoning AI

AI is undergoing a shift from simple LLM wrappers to reasoning agents that use reinforcement learning and iterative computation to achieve complex, goal-driven tasks. This new generation can plan, self-correct, and tackle open-ended problems, making previously “unautomatable” workflows like advanced math and coding competitions are now achievable for machines.

In the Costco Era of Software, Design Is the Differentiator

In the “Costco era” of software, where AI tools have mass-produced coding and lowered development costs, design quality and taste become the main product differentiators. With commoditized technology, users gravitate to elegant, intuitive products making thoughtful design principles critical for startups and incumbents to stand out in a crowded market.

How to build an AI company in a new market

Behind-the-scenes with Delphi and their vision to build a digital mind.

Marketing, Sales and PR

The Sales Playbook For Founders

Drawing from his experience founding Monzo and GoCardless, YC's Tom Blomfield shares his playbook for running a tight sales process that lands real, recurring revenue. He walks through each step—free and paid pilots, opt-out contracts, long-term deals—and shows how to prove value and close customers.

Don’t Ship Your Pitch Deck to Your Website. Here’s How to Translate Your Story for Customers

Your customers don’t want to read your pitch deck. Marketing expert Emily Kramer explains how to turn your investor talking points into your website messaging.

How to use Deep Research for GTM

You could save 10+ hours per week with this underused AI function.s

Much ado about margins: The grossly overhyped AI gross margin debate

There has been a lot of chatter recently on the "ugly" gross margin profiles of fast-growing early-stage AI companies. Is this a point-in-time feature or a long-term bug?

The perfect Product Pages for SaaS founders

Feature Pages, Use-case Pages & Customer-segment pages.

Money and Finance

Is Venture Broken?

What 2,000+ Priced Early-Stage Rounds Tell Us about the State of Seed & Series A.

Winner-Take-All Has Taken Over Venture. The Top 1% of AI Start-Ups Are Now Valued at 3-10x ‘Normal’ Multiples

The top 1% of AI startups now command valuation multiples 3 to 10 times higher than traditional SaaS companies, driven by deep AI moats, massive TAM expansion, and improving unit economics. This winner-take-all dynamic creates a stark market split where AI-native category creators receive unprecedented valuations compared to AI-enhanced or traditional SaaS businesses.

Women’s Health 2.0: Beyond Fertility

Women's health is a $66B opportunity. Learn why investors ignoring it risk missing massive returns as science, tech and culture align for change.

Valuation Matters

VCs face a tension between paying too much and risking reputation or paying too little and losing deals; success lies in paying market prices and differentiating on factors beyond price. While exceptions exist for transformative companies, overpaying as a norm jeopardizes portfolio returns and investor credibility, so the strategy is to "pay market, win by differentiation" with exceptions being rare.

Why Travel is the Next Big Opportunity in Sports

Travelers are spending more than ever on sports, but the consumer experience is still broken.