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SAME BUSINESS, ONE IS WORTH 20X MORE

Bill and Ramp do recognizably similar things, yet Bill trades around 2x revenue while Ramp just raised at $44 billion, roughly 15 to 30x.

OUR ACHILLES HEEL

Many people struggle to understand probabilities, leading to stress and misaligned expectations, especially in areas like college admissions and investments.

FAST MOVING WATER

Startup growth hinges on being in a rapidly expanding market, not just executing well.

SELECTION DEBT: ON DOING THINGS THAT DON'T MATTER

Selection debt is the cost of moving quickly on a poor foundational premise.

[SAVE MY FREE SPOT - June 17]

ANTHROPIC'S AI JOBS PAPER

Anthropic is using policy leadership as a brand strategy to position itself as the responsible AI company before AI-driven job disruption becomes a larger public issue. It has published a paper that outlines a three-stage response starting with wage insurance, retraining, and job matching, then expanding to public benefits and unemployment support, and eventually considering AI taxes, digital dividends, and universal basic income if AI broadly replaces human labor. The proposal aims to shape regulatory discussions early and build trust with enterprise buyers, investors, and governments. It could also provide a defense against future criticism by showing that it publicly acknowledged the risks and proposed solutions before large-scale job losses occur.

HALF OF AMERICANS FEAR AI COULD PUT SOMEONE IN THEIR HOUSEHOLD OUT OF WORK

53% of Americans worry AI could put them or someone in their household out of work. The same survey finds that 73% say they are concerned about AI's rising use overall, up from 68% in 2023. Concern is higher among Democrats at 61% versus 47% of Republicans. The poll also finds 50% of college graduates use AI regularly, compared with 34% of non-graduates, highlighting a divide between adoption and job-loss anxiety.

LOEWE'S TIKTOK STRATEGY

Most brands approach social as a distribution channel for work they've already decided is good. Loewe approached it as the thing that makes audiences want to pay attention to the work in the first place. An iPhone video, pushed through heavy internal resistance, generated 40M organic views because audiences were saturated with content that looked expensive. Getting good content approved is usually more difficult than creating it, and the brands with the strongest social presence tend to be the ones that have built enough internal trust to move fast on a vibe without a strategy document to justify it.

HOW TO FIX ABANDONED CART REVENUE LEAK

A common funnel improvement is splitting checkout into two steps, starting with an email opt-in before redirecting to payment. Once users begin checkout but do not complete it, an abandoned cart email sequence follows up to recover lost sales. This setup consistently improves conversions, typically increasing them by 10% to 20%, depending on traffic quality. It also runs as an evergreen system that continues to lift performance over time without ongoing manual effort.

SHOULD YOU BUY A BILLBOARD ON A BAY AREA FREEWAY?

OOH (out-of-home) works when it fits your audience, business model, creative strengths, and budget, not when it copies what competitors are doing. Billboards are expensive awareness tools that create broad, shallow awareness. Use them only when they can reach a concentrated or large audience and support the campaign across channels. A single Bay Area billboard can cost $20,000 to $50,000 per month, and meaningful visibility often requires multiple placements, so you need a clear goal and must weigh the opportunity cost against other channels. The strongest OOH campaigns pair bold creative with coordinated efforts across LinkedIn, events, product launches, and sales activity so the brand feels omnipresent.

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THREAD IT!

A 6-week guided challenge running from June 15 - July 26 for B2B marketers to build an authentic Reddit presence and improve AI search visibility. Participants will move from observing communities to engaging in discussions and creating original posts, with structured guidance and community support. It costs $29 and includes a curriculum, tracking tools, and feedback.

LINKEDIN'S CREATOR MARKETPLACE, A NEW ECOSYSTEM FOR BRAND/CREATOR CONNECTION

LinkedIn is launching a Creator Marketplace to connect creators with brands for partnerships like ads, speaking gigs, and collaborations. Access is invite-only based on content quality and audience fit. Invited creators opt in via a monetization tab, making their profiles discoverable to brands. Brands can then reach out directly to arrange deals.

HOW I RUN MY AGENCY WITH CLAUDE CODE (WEBINAR)

Hosted by Josh Lowman from Goldfront, this is a 30 minute live online session on June 17. It will cover how he rebuilt his agency around AI. He'll walk through the internal systems he uses, including agents, dashboards, and client tools. He will also share what's working and what still needs improvement.

FULLY REMOTE)

We're hiring a senior PMM to own product marketing at TLDR. You'll define our positioning, build out sales enablement, and lead every launch. Learn more [18].

THE RIGHT WAY TO USE AI TO BECOME A BETTER PMM

AI creates the most value for product marketers when it automates repetitive execution work and supports thinking, not when it replaces judgment, storytelling, strategy, or stakeholder management. PMMs should use AI for tasks like content repurposing, research summaries, and administrative work so they can spend more time on customer insights, positioning, and cross-functional influence. Identify recurring tasks where the quality depends on execution rather than judgment, then build simple workflows around them instead of chasing complex agents or tools.

WHAT CAN WE DO TO GET YOUNGER PEOPLE INTO MARKETING?

Entry-level marketing roles are being eliminated faster than the industry is reckoning with, as automation removes the task-based work that once served as the training ground for early-career marketers. The skills AI cannot replicate, judgment, creativity, and relationship-building, are precisely the ones best developed on the job, making the pipeline problem a long-term quality problem as much as a youth employment one. Agencies keeping early-career programs open argue the fix is redesigning how junior talent is assessed and deployed rather than waiting for economic conditions to improve.

RAMP'S DIRECT MAIL CARD

A photo of Ramp's oversized matte-black 3D card opening to reveal crumpled paper receipts.

PINTEREST ADDS AMAZON STOREFRONT LINKING FOR CREATORS

The new tool lets creators connect their Amazon Storefront directly to their Pinterest account.

THE CREATIVE TRENDS DEFINING WORLD CUP ADVERTISING

The strongest campaigns build around the experience of watching football rather than leading with a product or celebrity.

WHAT I TELL CEOS WHO WANT A PRODUCT TEAM SCORECARD

Product management resists simple metrics, so there is no universal scorecard for team health. Instead of dashboards, use structured discussion prompts across four 'lenses' to guide conversations with team members and stakeholders.

EVERYTHING IS RECORDED NOW

AI is making workplace recording the default, creating a living context layer that boosts productivity and visibility while forcing companies to govern privacy, legal risk, and employee candor.

AI DOESN'T MAKE YOUR JOB EASIER

AI hasn't made product management easier. It speeds up work so teams reach the hardest parts sooner - deciding what to build and how to prove it worked. As “yes” becomes cheap and AI-generated outputs arrive faster, the bottleneck shifts to human judgment, customer obsession, and evidence, requiring product teams to move from prioritization to curation supported by shared, team-level systems.

IN THE AGE OF AI, YOU NEED A POINT OF VIEW

In the face of AI-driven market shifts, technology buyers need a clear perspective on the future rather than just a product vision. To stand out, vendors must anchor their messaging in their unique strengths when helping buyers navigate the influx of AI information.

THE PM'S PLAYBOOK FOR SHIPPING AI FEATURES THAT ACTUALLY WORK IN PRODUCTION

This guide offers practical engineering strategies for shipping AI features in production, covering latency management, fallback hierarchies, a four-layer quality model, A/B testing nondeterministic outputs, and monitoring model drift.

HOW META SETS UP SUPER IC TEAMS

Super IC teams succeed when they have executive support, dedicated staffing, a clear business-backed customer problem, and an early plan for scaling the work into the broader organization.

ARE YOU ASKING THE REAL QUESTIONS?

AI makes building faster, but product teams still need to focus on value. The real questions are whether the product is hard to copy, whether customers have a strong reason to stay, and how quickly ideas create a measurable impact.

HOW TO SHARE YOUR POINT OF VIEW

Speaking up is a core way to add value, especially when you have close context on a problem. Share your point of view by grounding it in evidence, explaining why it matters, and matching your language to your level of certainty.

EVERYONE GOT EXCITED THEY CAN SUDDENLY CODE, AND COMPLETELY MISSED THE POINT

Product and organizational discovery (“what should we build?”) is what constrains outcomes.

LLM EVALUATION & BENCHMARKING

Reliable LLM products require rigorous evaluation beyond demos.

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SPACEX IPO IS SAID TO BE MORE THAN FOUR TIMES OVERSUBSCRIBED

The demand for SpaceX's initial public offering is more than four times the shares available. SpaceX's IPO is set to price today and trade tomorrow. It is offering 555.6 million shares at a fixed price of $135 each. The IPO is expected to rank as the biggest ever. Shares in the company will trade on Nasdaq and Nasdaq Texas under the symbol SPCX.

OPENAI CONSIDERS DRASTIC PRICE CUTS, ANTICIPATING WAR FOR USERS WITH ANTHROPIC

OpenAI is considering significant cuts to what it charges for tokens to counter similar anticipated cuts by Anthropic. Businesses have started to balk at the high prices for AI usage. Price cuts could potentially erode the profit margins for both AI companies, which are already losing billions of dollars due to the enormous cost of computing resources. A price war would be an early test of the companies' business models ahead of hotly anticipated public listings.

WORLD FIRST: PATIENT RECEIVES HIGH-RISK THERAPY TO MAKE CELLS YOUNG AGAIN

US-based biotechnology company Life Biosciences has dosed its first patients with an experimental therapy designed to reverse age-related vision loss. The treatment aims to turn back aging by activating three genes in nerves that do not naturally regenerate. The hope is that a single injection of the gene therapy, along with several weeks of antibiotics, can preserve or even restore vision. The genes are controlled by a genetic switch that only turns on when patients take the antibiotic, allowing for some level of control. The study will follow participants for at least five years.

CHINA JUST APPROVED THE WORLD'S FIRST COMMERCIAL BRAIN IMPLANT

China's National Medical Products Administration has approved the commercial use of NEO, a coin-sized brain-computer interface developed by Shanghai-based NeuraMatrix and Tsinghua University researchers. The device sits on top of the brain membrane to decode brain signals in real-time, enabling patients to control a pneumatic glove with their thoughts. US-based Neuralink has so far implanted its N1 device in at least 21 patients under research protocols, but the company does not have commercial approval. It plans to ramp up to high-volume production and near-full automated surgery this year, but FDA clearance for commercial sale is realistically years away.

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ANNOUNCING STACK OVERFLOW FOR AGENTS

Stack Overflow for Agents is an API-first knowledge exchange that extends the Stack ecosystem so agents can work at machine speed with humans still in the loop. It aims to close the gap between static training data and the rapidly shifting reality of production software. Stack Overflow for Agents uses a strict, multi-agent verification loop to create canonical knowledge. Each loop sharpens the corpus, and knowledge compounds as what's there keeps getting reality-tested. The system leverages a community trust factor to ensure accountability, prevent bad data loops, and maintain content quality.

HOW BUILDING AN HTML-FIRST SITE DOUBLED OUR USERS OVERNIGHT

Government websites are public services that should be available to everyone. They should work on every machine possible, even when connections are poor, and forms must never lose data once it is entered. This usually means government sites end up being simple HTML, as it is lightweight and works even on rubbish browsers. This concept of building with simpler technology can be applied to normal websites: increasing accessibility increases reach.

ANTHROPIC CEO DARIO AMODEI HAS ONLY ONE DIRECT REPORT

Anthropic's version of leadership allows its CEO, Dario Amondei, to protect nearly all of his time for big-picture conversation, organizational culture, and giving input on research direction and strategy. The company's executive team reports to Dario's sister, Anthropic President Daniela Amondei, who handles the company's day-to-day operations and reports to Anthropic's board. Dario's only direct report is Anthropic Chief of Staff, Avital Balwit. This is unusual in the tech sector, where many leaders are eliminating layers of management and widening spans of control.

FOR A SECOND TIME, TRUMP MUSES ABOUT AMERICANS SHARING IN AI WEALTH

President Donald Trump plans to soon hold a meeting with the top 12 or 15 executives in the AI industry to discuss the idea of companies giving something back to the public. This may involve providing the US with stakes in AI businesses that could be given to the public. It is unclear how such an arrangement would work or when such a meeting will take place. While AI has the potential to create significant wealth, it could destroy many jobs, leading to a series of unusual ideas on how to relieve pressure on the companies responsible for those job losses.

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THE UNTRAINABLE

As intelligence gets cheaper, the value slides towards the few places models can't reach.

TESLA'S ROBOTAXI FALLS SHORT WITH LONG WAITS AND STALLED RIDES

Tesla only has 59 Robotaxis in three Texas cities.

HOW LONG UNTIL AI DOESN'T NEED HUMANS?

Self-sustaining AI that can exist without humans probably won't be achievable within the next decade.