Founder Weekly (Issue 687 May 28 2025)

Welcome to issue 687 of Founder Weekly. Let's get straight to the links this week.

Keep more of what you earn

Collective helps members keep more of what they earn — saving an average of $10,000 a year in taxes* — while taking countless hours of administrative work off their plates.

Your membership includes LLC and S Corp formation, payroll, monthly bookkeeping, quarterly tax estimates, annual business tax filing and more.

Get your first month free with code SPRINGFREE

_{*Based on the average 2022 tax savings of active Collective users with an S Corp tax election for the 2022 tax year}

General

Conviction-Led Contrarianism

The article explores the concept of conviction-led contrarianism, emphasizing that true progress and innovation often require challenging the status quo—but simply being contrarian isn’t enough; you must also be right. It warns against contrarianism for its own sake, highlighting that independent thinking must consider real-world dependencies and that the courage to act differently is only valuable when paired with sound judgment and awareness of reality.

How to Build for a Market That Doesn’t Exist Yet — Braze’s Path to Product-Market Fit

The Braze founding team shares all the early moves they made to lay the path to IPO.

Vertical AI's Integration Problem

Vertical AI startups face major integration challenges because legacy industry software often restricts or complicates access to essential data, making it hard for new AI tools to deliver value. Founders are tackling this with creative strategies—like wedge products, data extraction, SMB focus, partnerships, and leveraging new AI infrastructure standards—but integration remains a critical hurdle for scaling vertical AI solutions.

Voice AI is Working. Here’s Where It Wins First

Voice AI is now ready for mainstream adoption thanks to breakthroughs in speed, cost, and accessibility, enabling startups to build compelling voice-first applications. The article highlights how this shift is driving rapid growth in B2B automation, new consumer experiences, and opening opportunities for emotionally intelligent, “soulful” AI interactions.

The Architects of Experience

The article explores how modern brands are redefining consumer experiences by blending digital innovation with human-centric design. It emphasizes that companies who thoughtfully architect every touchpoint can build deeper customer loyalty and lasting business value.

Marketing, Sales and PR

Growth tactics from OpenAI and Stripe’s first marketer

Krithika Shankarraman, the first marketing hire at OpenAI and Stripe, shares lessons from building marketing foundations at leading tech companies, emphasizing the importance of deeply understanding customers over following generic playbooks. She discusses how effective marketing clarifies product use cases, why being “better” than competitors isn’t enough, and how creativity and consistency drive lasting impact—especially in the rapidly evolving AI space.

Developer marketing is show and tell

Tell them what you're going to ship. Tell them what you've shipped. Tell them what others have shipped with your tool.

YouTube Comment Section is a Marketing Goldmine (If You Know How)

Your best marketing channel might be hiding in plain sight: YouTube comments. It's not about spam, it's about value, and knowing the strategy.

How to measure topical authority [in 2025]

Topical Authority is still a mystical concept, partly because we don't have a good way to measure it. In this post, I want to offer a method to quantify Topic Authority.

Money and Finance

Red Flags in Deep Tech Pitches That Look Like Green Flags

And how founders can reframe them to earn trust, not skepticism.

The First 40 Months

Why founders should precisely understand what milestones are needed through their first two rounds of fundraising instead of sprinting from round to round.