Recent content in Writing on Craig McCaskill
If you self-host on a cloud VPS, you’ve probably noticed by now that some of your services can’t send email. DigitalOcean, AWS Lightsail, Linode, and Vultr all block outbound SMTP on ports 25, 465, and 587. It’s an anti-abuse measure: compromised VMs make great spam relays, and one bad actor can burn the reputation of an entire IP range. The official recommendation is to use a…
Two environmental artists. Three months. Five hand-built buildings for an indie game’s city district. Every facade custom. Every texture intentional. Three months of craft for five structures players will sprint past in eight seconds on their way to the next quest marker. Or: a generation pipeline produces fifty convincing models in an hour. Variation, weathering, architectural detail. Good…
Or: before you blame the players, check the rules. I once watched a team of smart, well-intentioned people spend six months optimizing a metric that didn’t matter. Not because they were confused about what actually mattered. Because the metric was what got discussed in leadership reviews. Everyone on the team could have told you what would move the business. They also knew it wouldn’t show up on…
Or: intellectual honesty is your competitive advantage. In 2011, Netflix made a decision that, at the time, looked catastrophic. They split their DVD-by-mail service from streaming, raised prices by 60%, and watched 800,000 subscribers cancel in three months. The stock cratered from $300 to $77 in a single day. Saturday Night Live mocked them. Investors called for Reed Hastings to resign.…
Imagine you watch a video. Multiple angles, timestamped, from bystanders with phones. You see what happens. A confrontation. A shooting. The sequence of events is clear. Then you read the official statement, and it describes something else entirely. Not a different interpretation of ambiguous footage. A different set of facts. The victim attacked officers, the statement says. The officer was…
The four words that precede every crash: “This time is different.” Except this time, the person warning about a bubble is Sam Altman, the CEO most responsible for creating it. When OpenAI’s chief executive warned last week that investors were “overexcited” about AI, markets reacted immediately. Nvidia fell 3.5%, Palantir dropped nearly 10%, and the selloff spread globally. The warning came amid a…
Product management is built on a contradiction. We’re supposed to be data-driven, yet our most important decisions happen in the absence of clear data. We’re meant to be customer-focused, yet customers can’t tell us what they’ll want tomorrow. Navigating this requires two underappreciated skills: sensing and sensemaking. These aren’t the skills we talk about at product conferences or test for in…
Your product is crushing it. Customer satisfaction scores are through the roof. Your biggest clients are renewing multi-year contracts. The board is thrilled with your margins. And yet, somewhere in a garage or a dorm room, someone is building the thing that will make your product irrelevant. The scariest part? Doing everything “right” according to conventional business wisdom is exactly what will…
New tools don’t just change what we can do, they change who wins. The printing press didn’t eliminate scribes overnight, but it made literate societies dramatically more powerful than illiterate ones. Every technological shift creates a predictable pattern and early adopters gain disproportionate advantage over those who wait. What makes AI different isn’t the technology itself, but the speed at…
I’ve been writing again. After nearly four years of letting my website collect digital dust—publishing only a few posts while my day job consumed all my creative energy. I finally felt the itch to both write and fix the stagnant site that housed my thoughts. The site functioned—posts appeared, links worked, the basics held together. But navigating it was like searching through a poorly organized…
Something humbling happened last week: three hours of my life disappeared into a blank document with barely a paragraph to show for it. I sat down to write a product strategy document – something I thought I’d mastered after years of practice. In meetings, I can usually help teams navigate the tough questions: what to build next, how features connect to business goals, which metrics matter most.…
Every company claims to be disciplined about prioritization; most roadmaps look like feature buffets with everything marked “high priority.” The space between strategic intention and daily execution is littered with good ideas that never shipped. The irony wasn’t lost on me: I was writing about prioritization while completely failing to prioritize my own content. What started as a focused piece…
The math of product is simple but brutal: too many demands, not enough resources. Your backlog isn’t just full—it’s a graveyard of good intentions. When every feature is called “critical,” nothing actually gets built well. This isn’t about managing tasks better. It’s about survival. Because when everything matters, nothing really does. The True Cost of Poor Prioritization Poor prioritization costs…
You ship feature after feature, your development team works overtime, your backlog is always full—yet customer satisfaction remains flat and business metrics barely budge. Sound familiar? You’re not alone. Most product organizations have fallen into what Melissa Perri calls “the build trap”: the dangerous cycle of equating more features with more success while losing sight of actual customer…
AI is making us all smarter in exactly the same way, and that might be the problem. What happens when the most accessible knowledge becomes the most uniform? As AI increasingly curates what information we see, are we trading the beautiful messiness of diverse human thought for algorithmic convenience? Andrew Peterson’s April 2024 research paper “AI and the Problem of Knowledge Collapse” 1 reveals…
In the quest for clarity and alignment, modern organizations increasingly embrace structured goal-setting frameworks like OKRs (Objectives and Key Results). But beneath the surface of these seemingly rational systems lies a deeper question: Are we measuring what truly matters, or simply what’s easy to measure? The Metrics Paradox Here’s the hard truth about metrics: we’ve become obsessed with…
In 2012, Netflix was a meticulously organized catalog that helped you discover films and shows across genres, decades, and continents. In 2015, Spotify was a music lover’s sanctuary that put your personal library and thoughtful exploration front and center. Fast forward to today, and these platforms—along with YouTube, LinkedIn, and countless others—have morphed into something unrecognizable to…
Last week, philosopher Harry G. Frankfurt passed away. As a young adult, his essay “On Bullshit” completely changed how I thought about truth and lies, especially given a personal history with family who had a tenuous relationship with the truth. When I heard the news of his death, I felt pulled to read it again, wondering if it would hit differently after a couple decades of life experience.…
Here are the slides for the lightning talk I gave at Conversion Conf 2014, aimed as an introduction to psychology in design, why it matters and what drives us to make decisions. The goal of this talk was to give people without a design background a quick intro into psychology and how large an impact it can have on your products.
For anyone looking to get into User Experience, I can’t recommend enough that you read Jesse James Garret’s book The Elements of User Experience . It provides a great framework for thinking about design and gives you a structured rationale and toolkit to deal with just about anything. This is the book you read to find out just how little you actually know about UX, and what those gaps are. Jesse…
Imagine you have never used an iPad before, but I tell you that you can play chess on it. Before you turn it on, you will already have started building a mental model of how the chess game will look, how you will interact with it, and what you will be able to do. This is a different way of thinking about chess from someone who has already used an iPad, from someone who is a chess master playing on…