My riff in it for software is “if you’re so smart, then why don’t you ship?”
Most teams in software think they’re above standards SDLC practice. They’ll adopt the easy stuff (sprints, ceremonies, etc), but make bizarre changes to “suit the needs of the team”. Just today, a principal engineer suggested 4 week sprints, with the first week reserved for planning. This, he says, is perfect for us, because it gives us the space to figure out what we’re doing.
This is supposed to help us reliably commit to work and deliver it on time. No other changes to how we intake projects or refine them or decompose them or assign them. We‘ll just tweak a couple of variables. Compress all the refinement into one week, and tack an extra week into the working time.
I’m a scrum purist. Or a Shape Up purist. Hell, I’d even get behind waterfall if we followed the methodology to a T. I think I’m pretty smart, but I’ve learned that I’m not smarter than a coherent SDLC methodology. Your company is not going to win because you have a novel way of delivering software.
The best teams I’ve worked with live and die by the book. Except that they don’t die, they just reliably deliver high quality software, then go home to live in bliss, because they didn’t spend all day trying to untangle whatever mess their newfangled project management system got them into.
Like every other team that does this, we’ll try it out for a couple of months, realize it isn’t working, and chalk it up to “learning as we go”. But god forbid someone suggest that we just follow the handbook. That’s just not going to work for us. We’re different. Our team is special.
To which I say, “if we’re so smart, why aren’t we happy?”
August 11, 2026
Grok Bot dropped today and it’s a bright spot in my otherwise pessimistic AI outlook of late. It’s the first love child of the Cursor and SpaceXAI merger (it really is a merger, even though it’s technically an acquisition). It feels just like Cursor, and has the personality of new X (Benji Taylor’s fingerprints are everywhere).
Just a month ago, commenting on Cursor’s new side chats feature, I tweeted:
Once Cursor builds a harness for general purpose knowledge work, everyone else is fuckin toast. They’re the only AI company with a cohesive product, and over the next couple they’ll start lapping the competition.
I wasn’t expecting to see it happen quite this soon, but I’m not at all surprised it’s been executed so well. I’ve been using Cursor as my daily driver for the last 2 years, with Composer (and lately Grok) as my main models. That combo hits the sweet spot of smart, speedy, and pleasant to deal with. Cursor’s harness is really great, doesn’t require any skills to be effective, and lately has made great use of subagents.
Grok Bot feels exactly the same in my initial use. I created my first agent by asking Grok about to build me a fleet of agents:
Help me create a fleet of agents that can help me launch and grow a product design agency that helps seed to series B b2b SaaS companies improve their onboarding and activation. I follow a lot of what Alex hormozi has to say about offers, and also what Daniel fazio of client ascension has said about ai assisted agencies.
Bobjobs understood the assignment, and spun up 7 additional agents to put under his command.
The main agent then helped me “launch” my agency by summoning the specialist agents to build offers, research my ICP, create lead lists, and more. The handoff is relatively seamless, the main agent will delegate a task, continue doing its own work, and wait for the other agent to report back.
Like in Cursor, you’ll frequently be presented with multiple choice questions to keep the agents on track. They’ll calmly do what they’re asked, and spit out documents as they go to give you durable artifacts of their work.
A distinguishing feature between Grok Bot and every other AI tool I’ve used is that your work with the agents feels durable. Rather than turn-based chats about a single topic, Grok Bot is meant to behave like iMessage or Slack. Conversations are continuous, and not meant to be thrown away when you’ve reached a conclusion.
Agents truly act as coworkers. You can tag them in and out as you need, or spin up new group chats to work together on something specific.
None of this is earth shattering. Some folks have been developing patterns like this over the course of the year. But Grok Bot is the first time I’ve seen this tech put into a polished product that feels like more than a demo.
I’m really, really excited to see what the Cursor and X teams are able to build together. Both companies feel collaborative, and give an MMORPG vibe. Claude and OpenAI, in contrast, very much feel like thousands upon thousands of single player games being played simultaneously.
To Americans, this comes out of left field. I find it fascinating that Dario was adamant to push back against the US government earlier this year, but gives into the EU without much fanfare. I’m sure activist groups on this side of the pond will pick up on this headline and push for similar regulations here.
Anthropic says that all text and graphics generated by Claude will include these watermarks, but doesn’t call out code one way or another. That will be a very slippery slope, because they could be laying the groundwork for accepting liability when the LLM’s code wreaks havoc down the line.
To me, liability is going to be the biggest roadblock to widespread agentic AI. Our world depends on having wringable necks to take responsibility when things go awry. When you remove humans from the loop, you also remove the easy placement of blame.
I doubt that Anthropic counsel and shareholders will allow the company to hold the bag, and this move to attach provenance to Claude’s output gets them one step closer to some very uncomfortable situations.
August 9, 2026
Every so often, I stumble upon an interesting book in Amazon's recommendations that I've never seen.
Yesterday, it was Articulating Design Decisions by Tom Greever. I would've normally (and likely have previously) scrolled right past it, because on the surface, it sounds pedestrian.
But lately, I'm finding myself having to articulate my design decisions! In the last quarter, our company lost the PM that I've worked with for over 3 years, and also the CTO who'd sponsored our big project. You forget how luxurious familiarity can be until you find yourself surrounded by strangers, trying to work without the faith that once empowered you to move without resistance.
Last week, I was caught off guard by reasonable questions about my work, and felt embarassed that I wasn't prepared with a good response. All the context is gone, the relationships lacking, and my confidence is disappearing. So a book about articulating is serendipitous.
Most of the book throws red flags, as it's written in the spirit of How to Win Friends and Influence People and Seven Habits of Highly Effective People. I'm allergic to people-pleasing, and this book points out that a successful designer is often the most agreeable one. It also suggests that the way to articulate choices is by having lots and lots and lots of meetings.
I almost put the book down, until I realized that there are two types of designers:
Designers that take orders
Designers that make magic
Most designers are the former. They'll provide a menu, but are happy to allow stakeholders to customize their orders.
But the best designers, the ones that make magic, are omakase designers. Somehow, some way, they gain the trust of stakeholders so much that they're able to do whatever they want, and the stakeholders excitedly eat it up, no matter what. The most celebrated products are made by omakase designers, who are have a vision and the leash to make it reality.
Just how does a designer get that leash? What do they do that gains them so much trust from the people footing the bill?
It's not because they have a better pedigree or are more talented or have better ideas.
It's because they communicate precisely why their solution is not just the right solution to a problem, but the only solution. They know that the place they landed is inevitable, and pull the rest of the team along in such a way that they know it too.
Here are 5 key traits of the omakase designer:
They're aware of the problem that needs to be solved
They know how a solution will be deemed successful
They are aware of each choice, big and small, that they made inside their process
They're able to explain why they made each choice in the process
They document all of the above in a way that makes the points above visible
Everything else is finesse. You can be a flaming asshole or a hack of a designer and still be successful if you're able to communicate why your solution is the best one available. The author tries to convince the reader that all the intangible skills are imperative, but they're secondary to your ability to bring your audience along for the ride.
August 8, 2026
The world wants you to be Kroger. Be Jungle Jim.
August 7, 2026
If you Google “through of disillusionment” you’ll find a bunch of premature articles from 2024 and 2025 talking about how AI is in the low point of the current hype cycle.
Summer of 2026 will go down as the real trough, and January 2026 will be remembered as the peak. The tech didn’t get good enough until late 2025, and it took the holiday downtime for people to realize how powerful it had become.
Leaders spent Q1 trying to mandate agentic workflows, and by Q3 they realized that they blew through the year’s budget with little to show.
Come September, when everyone’s back from Summer, there’s a lot of sobering up to be done. Startups that raised on insane valuations will have to face the economic realities of their business. Established players will shift focus from agents back into their core line of business.
By early 2027, the industry will restructure around these realities, and sanity will return.
Tech companies are shipping the most impressive things their models can do—such as navigating a website or writing code—rather than creating products tailored to their customers' desires. Those capabilities may become great features some day, but right now, they feel more like demos.
There are but a few companies making coherent agentic products. The two leading model labs, while their tech is magical, are increasingly feeling like playgrounds, not products.
Unsurprisingly, Lenny's Newsletter is at the top. I'm curious what other newsletters for PMs are popular among startups. There are a few that come to mind, but they're all derivative of the style Lenny made famous.
On the whole, the landscape for software-related media is bleak. Based on what's popular, you can tell that the appetite for content is exclusively big picture. It's all about "strategy", war stories, and unempirical pontification. Don't get me wrong, there's a lot of great stuff from Lenny and company. But more and more, the top players in tech media feel like empty calories.
And it shows. The fat are getting fatter, gobbling up talent and VC dollars in pursuit of the singularity. Basic technical and economic fundamentals don't apply, at least not right now. Sooner or later, bad habits will catch up with them. You'd hope they will shape up with diet and exercise. But more realistically, they'll push the peptides and act like nothing was ever out of sorts.
I miss the days of old, where you could actually learn your craft one blog post at a time. Entire brands and businesses were born by sharing practical knowledge that readers could apply to the work they were doing that very day. I owe my career to Chris Coyier and the team that ran CSS Tricks. And I learned how to become a designer thanks to many podcasts, YouTube videos, and other how-to content on the web.
There was a type of clean eating I practiced early in my career that accelerated my growth. All that media molded me into the pro I am today. But I look around now, and take stock of the calories I've eaten lately, and it's no wonder why everything feels bloated.
so many teams want to move fast but are stuck in the trap of "the first calendar slot that works for everyone is next Thursday at 2pm so we'll kick things off then"
Loaded calendars are a cancer lurking inside of software companies. If I had a dollar for every time someone's daily update alluded to wall-to-wall meetings, I'd be sitting on a beach instead of writing on this blog.
If there's one concept that this industry struggles with, it's opportunity cost. We believe that because we can, we should. So we say yes to everything, not realizing all of the possibility lost because we're going with the flow.
So we go with the flow until we find ourselves paralyzed by a laissez faire attitude towards time. Regular 1:1s become the norm. Everything has to get run through a committee. We find ourselves in meetings about meetings. The workday is filled with metawork, everyone knows it, but nobody is willing to raise their hand and say "this is wrong".
I'm reminded of Shopify's 2023 memo to employees, where they enforced a "calendar purge" in order to free up time to do the work that matters.
"The best thing founders can do is subtraction,” Chief Executive Officer Tobi Lutke, who co-founded the company, said in an emailed statement. “It’s much easier to add things than to remove things. If you say yes to a thing, you actually say no to every other thing you could have done with that period of time. As people add things, the set of things that can be done becomes smaller. Then, you end up with more and more people just maintaining the status quo.”
When you're operating on the manager's schedule you can do something you'd never want to do on the maker's: you can have speculative meetings. You can meet someone just to get to know one another. If you have an empty slot in your schedule, why not? Maybe it will turn out you can help one another in some way.
Business people in Silicon Valley (and the whole world, for that matter) have speculative meetings all the time. They're effectively free if you're on the manager's schedule. They're so common that there's distinctive language for proposing them: saying that you want to "grab coffee," for example.
Speculative meetings are terribly costly if you're on the maker's schedule, though. Which puts us in something of a bind. Everyone assumes that, like other investors, we run on the manager's schedule. So they introduce us to someone they think we ought to meet, or send us an email proposing we grab coffee. At this point we have two options, neither of them good: we can meet with them, and lose half a day's work; or we can try to avoid meeting them, and probably offend them.
Graham's solution is regularly scheduled office hours, which sounds nice in principle, but doesn't feel scalable. Inevitably, people will want more access and more information and more connectedness. Office hours will begin happening daily, then multiple times per day, until someone decides that dedicated recurring meetings are the better option.
All products with strong brand recognition that have gotten lost after the ZIRP grow-at-all-cost era. Each fits squarely into a SMB segment that's willing to pay (but not pay big) for software that does what it says on the tin.
These are all "finished products" that can be shaped up, then put in KTLO mode as steady profit machines. All you'd need to to is create the appropriate unit economics and make sure the brand stays visible when people enter buying scenarios.
The commentariat will have the world believing that Airtable is yet another victim of the AI revolution. They'll say that Airtable was simply not needed because people can build build their own apps and workflows with their trusty LLM.
But that ignores everything that came before AI.
Airtable (alongside Notion) were the darlings of the no-code movement that boomed from the late 2010s until 2023. Entire businesses were built around no-code platforms, largely aimed at helping SMBs automate workflows and build custom solutions to their problems. This was revolutionary, because bespoke software was formerly reserved for the enterprise.
In hindsight, it's really surprising that Airtable was very public about their shift to an enterprise GTM back in 2023. The Fortune 500 have fleets of engineers building and maintaining custom software. If they're using no-code tools like Airtable, it's to manage the scraps. Those projects that weren't deemed important enough by the CIO to get on the yearly budget are made possible with bubblegum, duck tape, and Airtable.
Relatively speaking, these enterprise customers surely have the highest contract values and, on the surface, that's really exciting to executives who are looking to squeeze every ounce of juice from the company. There's nothing wrong with going after these whales, but doing it at the expense of the small fish is a huge gamble.
In 2022–2023, they laid off over 1,000 employees over 2 rounds of cuts. During the 2nd phase, their founder and CEO Howie Liu said:
...the cuts will be company-wide, with the largest layoffs hitting product and sales teams that were focused on selling and servicing smaller clients. “We are realigning to go after bigger use cases, and therefore bigger deals. We want to consistently get customers with million-dollar-plus spend rates, versus supporting lots of little ten-thousand-dollar customers from a sales touch standpoint.”
Not only did they choose to go upmarket, but Airtable was actively hostile towards their SMB customers. In 2023, they effectively doubled their pricing on lower tier plans, and since then there have been other policy changes to make the product more expensive for SMBs. Here's a quote from an irrate customer, straight from their community forums:
I've been a customer for more than 3 years, and have spent 1000s of man hours optimizing the system for our needs, and we just got a message that's basically saying that we have 3 weeks to move to another platform, or pay more than twice the money you've been paying just in order to keep things running.
Three years on, Airtable is dealing with the consequences of poor strategy. They pushed a good chunk of revenue out the door, changed their messaging so that prospects go elsewhere, and then discovered that very few enterprises are willing to pay millions of dollars per year for overflow projects and prototypes.
As the AI boom happened, people were building more software than ever, and still needed a place to store all of their data. Mind you, these builders were looking for free and cheap database solutions for their new apps and workflows. Airtable was nowhere to be found, because they turned off all of their marketing targeted at this cohort. In that void, slightly more technical database solutions like Supabase became the LLM's recommendation, further eating into Airtable's growth.
Around this time, Reforge's Unsolicited Feedback podcast interviewed growth leader Elena Verna about Airtable's shift. She was confused by the choice, calling out that most of the company's growth came from SMBs, and most of these SMBs fall in love with the product because of it's self-serve nature. And when you choose to have a sales-led GTM, she believes it's because there's something about the product that users need to be told by a representative from the company.
On the same episode, Fareed Mosavat (formerly Direct of Product at Slack) mentioned some stats about Slack's enterprise deal flow:
97% of our $100K+ enterprise deals started as free. Something like 65% had paid PLG small teams before we engaged them at all with the sales team. The fuel for the enterprise business was the PLG.
Verna went on to mention how the "shift" was a bad idea. You always need to layer one GTM on top of the one that's already working, not replace one with another.
That's exactly what happened at Airtable. Sure, it is still self-serve today, but looking through the messaging, through the logos on their homepage, they are all-in on enterprise sales. And now that their PLG to enterprise pipeline has dried up, the founders have no choice but to sell. It's a downward spiral that's direct fallout of poor marketing strategy.
I'd be foolish if I didn't mention how tech's disrespect of marketing (as a discipline) continues to bite them in the ass. Silicon Valley believes that "distribution" (aka owned channels) is all you need to grow a company. With some humility, they'd read some of the literature coming out of marketing science think tanks like the Ehrenberg Bass Institute, and learn that brands only grow when they can acquire new customers. Selling more to existing customers (like Airtable's enterprise GTM) is the path to stagnation and death.
Bending Spoons knows this. I'd wager their team is well-versed in the works of Byron Sharp and others. Every company in their portfolio has tremendous brand equity, and built their original businesses on the back of a self-serve GTM. They'll return focus to the SMB segment, build goodwill with those buyers, and build a healthy business.
This cartoon from Bob Moesta’s Demand-side Sales 101 is the perfect summary of jobs-to-be-done thinking.
A JTBD is the progress that a person is trying to make in a particular struggling circumstance.
It’s our job as producers to get them from point A to point B in the fastest way or the cheapest way or the most comfortable way, but in the way that best suits the consumer’s current condition.
Everyone has written off the iPad as a serious work machine, but maybe, just maybe, AI apps make it a useful computer. I've long hoped that the switch to M series silicon, and the not-so-subtle convergence of Mac, iPad, and iOS interfaces, meant that we'd have a universal platform by now.
I'm sure we'll get there some day, but using Cursor on iPad can fill the void in the meantime. Marking up a view with the Apple Pencil for Cursor Agent to make changes is especially exciting.
I've not yet played with Paper, but concepts like this one are intriguing. I am still long on Figma, and I suspect that they'll eventually have a hybrid canvas and HTML renderer, so that they can take advantage of a DOM for browser-like features.
We can thank consumer social and e-commerce for the huge cache of research that led to the mobile-first mafia.
Clicks and conversions are king over there, and growth teams figured out the patterns to squeeze every last penny out of each interaction.
Business tools, ironically, get to operate on vibes much more than any data-driven leader would care to admit. It is painfully evident when using many top B2B SaaS tools, where workflows are erratic and it takes 10 clicks to complete one task.
