Chris Spiek and Ryan Singer on Shape Up

September 28, 2022 • #

Reading Ryan Singer’s Shape Up a few years ago was formative (or re-formative, or something) in my thinking on how product development can and should work. After that it was a rabbit hole on jobs-to-be-done, Bob Moesta’s Demand-Side Sales, demand thinking, and more.

Since he wrote the book in 2019, he talks about 2 new concepts that extend Shape Up a little further: the role of the “technical shaper” and the stage of “framing” that happens prior to shaping.

Framing is a particularly useful device to add meat onto the bone of working through defining the problem you’re trying to solve. Shaping as the first step doesn’t leave enough space for the team to really articulate the dimensions of the problem it’s attempting to solve. Shaping is looking for the contours of a particular solution, setting the desired appetite for a solution (“we’re okay spending 6 weeks worth of time on this problem”), and laying out the boundaries around the scope for the team to work within.

I know in our team, the worst project execution happens when the problem is poorly-defined before we get started, or when we don’t get down into enough specificity to set proper scopes. I love these additions to the framework.

Popper on Great Man Theory

September 27, 2022 • #

This just showed up in my Readwise highlights today, from Karl Popper’s The Open Society and its Enemies:

It springs rather from my conviction that, if our civilization is to survive, we must break with the habit of deference to great men. Great men may make great mistakes; and as the book tries to show, some of the greatest leaders of the past supported the perennial attack on freedom and reason.

Popper opposes the historicist Great man theory, where we attribute outsized impact on the world to singular people. Here he reminds us that deference to great men encourages hubris and overconfidence. We should remember that some of the worst assaults on the freedom and open societies are also the doings of these “great men”.

Ian Inbound

September 26, 2022 • #

As of this weekend, Hurricane Ian is in the Caribbean with a projected track that puts it making landfall this week on the western coast of Florida, not far from where we are. Looks like we’ll be spending some time getting the house prepared for the storm. Doesn’t look like there’ll be an evacuation for us.

Portals Into Earth

September 21, 2022 • #

From John McPhee’s Annals of the Former World:

Geologists on the whole are inconsistent drivers. When a roadcut presents itself, they tend to lurch and weave. To them, the roadcut is a portal, a fragment of a regional story, a proscenium arch that leads their imaginations into the earth and through the surrounding terrane.

This is a book I’d love to revisit. So many great bits of history.

The Simplest Thing

September 20, 2022 • #

When working through problems, the most impressive creators to me aren’t those that divine an entire solution in their brain for an hour, then slam out a perfect result (spoiler: this doesn’t exist outside of the occasional savant). I love to watch people who are great at avoiding the temptation to overcomplicate. People who can break problems down into components. People who can simplify complex problems by isolating parts, and blocking and tackling.

I enjoyed this, from an interview with Ward Cunningham (programmer and inventor of the wiki):

It was a question: “Given what we’re trying to do now, what is the simplest thing that could possibly work?” In other words, let’s focus on the goal. The goal right now is to make this routine do this thing. Let’s not worry about what somebody reading the code tomorrow is going to think. Let’s not worry about whether it’s efficient. Let’s not even worry about whether it will work. Let’s just write the simplest thing that could possibly work.

Once we had written it, we could look at it. And we’d say, “Oh yeah, now we know what’s going on,” because the mere act of writing it organized our thoughts. Maybe it worked. Maybe it didn’t. Maybe we had to code some more. But we had been blocked from making progress, and now we weren’t. We had been thinking about too much at once, trying to achieve too complicated a goal, trying to code it too well. Maybe we had been trying to impress our friends with our knowledge of computer science, whatever. But we decided to try whatever is most simple: to write an if statement, return a constant, use a linear search. We would just write it and see it work. We knew that once it worked, we’d be in a better position to think of what we really wanted.

The most impressive software engineers I’ve worked with have a knack for this type of chewing through work. The simplest thing usually isn’t the cleanest, fewest lines of code, fewest moving parts, or the most well-tested. Simple means “does a basic function”, something you can categorically check and verify, something a collaborator can easily understand.

Sometimes you just need to first do the Simplest Thing before you can find the Correct thing.

Steve Jobs on Ideas vs. Products

September 19, 2022 • #

A lot of Steve Jobs content is hagiography at this point, but this clip is fantastic:

There’s an enormous delta between idea and execution. Someone can take a great idea and squander it. Or conversely, someone could take a middling and obvious idea and execute so well they build a billion dollar business. From the first part of the clip:

One of the things that really hurt Apple was after I left John Sculley got a very serious disease. And that disease, I’ve seen other people get it, too, it’s the disease of thinking that a really great idea is 90 percent of the work, and that if you just tell all these other people “here’s this great idea” then of course they can go off and make it happen. And the problem with that is that there’s a just a tremendous amount of craftsmanship in-between a great idea and a great product, and as you evolve that great idea it changes and grows it never comes out like it starts because you learn a lot more as you get into the subtleties of it. And you also find there’s tremendous trade-offs that you have to make. There are there are just certain things you can’t make electrons do, there are certain things you can’t make plastic do or glass do or factories do or robots do. And as you get into all these things, designing a product is keeping 5,000 things in your brain, these concepts, and fitting them all together and kind of continuing to push to fit them together in new and different ways to get what you want and every day you discover something new that is a new problem or a new opportunity to fit these things together a little differently. It’s that process that is the magic.

The idea of “making to know”, or of starting the work in order to figure out the specific contours of the work, these are fascinating concepts to me. So many of the great innovations of our time are the function of the college dropout, or the less-educated craftsperson, experimenting through years of trial and error to make something happen. Often the only way to know the true bottlenecks, challenges, and chokepoints of bringing an idea to consumers (buyers, audiences, customers) is to get started. Make the map of the territory along the way.

On Markets, TAMs, and Agency

September 16, 2022 • #

If you’ve been involved in investing or fundraising activities in the past, you’ve likely heard about “TAMs” (total addressable market), as in “So what’s your TAM look like?” The general idea is to determine a metric that communicates in few words the nature of a given market for a product or service. Investors want to know how a company thinks about its market opportunity (investors generally want large ones), and startup founders need to have a sense for what they can realistically target, build for, sell to, and capture to build a business. You may also have heard of TAM’s cousins, like SAM and SOM (serviceable addressable market and serviceable obtainable market), but let’s stick to the big one here.

TAM is part of the lingua franca of the fundraising process, a term thrown around casually and understood in a variety of ways by investors and operators alike. For those of us on the operator side of the table, calculating your TAM is a necessary part of the company-building and fundraising process. Most founders don’t start with the question of “What’s the biggest TAM I could target?” before starting on their idea. Picking apart the market specifics is typically downstream of prototyping an idea for a job to be done. As a founder you have to think about how to effectively communicate just enough here to be useful to the audience. But how is TAM useful? What is an investor doing with those numbers beyond saying “Yep, this is big enough”?


What TAM analysis is good for

Firstly, a TAM serves to communicate how a company thinks about its target customer. Let’s say you build a team collaboration tool for cross-company projects. Who are the targets? What size companies? Is there a narrower industry focus? Generally the wider your target, the harder it will be to convincingly portray a useful TAM. Simply saying “anyone on Earth could be a customer, our TAM is $500 trillion” won’t persuade anyone, not to mention you’ve got quite the uphill battle to build and sell to such a broad audience. Being narrower isn’t a flaw, it’s a feature.

Which brings me to the second use for TAM: signaling the quality of your thinking about your business. A thoughtful, concise TAM analysis functions not only as a means to convey who your target is, but also as a sign of how thoroughly you’ve thought about the prospects of the business itself, meaning how to tackle a go-to-market. If you can tell a persuasive story about your target market, it lends credibility to why an investor should trust you with their money. A sloppy, or overconfident, or poorly-articulated market description (even if you have a baller product) doesn’t reassure anyone that you’ll be a good steward of the dollars. It’s like some people say about college degrees: they’re useful as signals of wherewithal and commitment as much as they are on their own merits of intelligence. They signal that you see something through to the end, a quality in higher demand by some employers than whether you have a BS in physics or a BA in philosophy.

But enough about the reasons why TAM matters. Let’s cover some reasons it’s not very useful, at least beyond a “qualifying variable” stage.

Then what’s wrong with TAMs?

Well, nothing is “wrong” with them, but they are quite often overvalued. For investors, how you read a TAM analysis and what emphasis to place on it is something to be circumspect about.

For one, markets aren’t static fixtures; they move, expand, and contract all the time. They’re moving targets. Sure, even with an understanding of this factor, a TAM can be useful as a snapshot in time as it stands the moment a deal is getting done. Even well-defined categories move all over the place. It’s more informative to look at it directionally — whether the market is expanding, or if it’s shrinking or being subsumed by an adjacent one.

Some of the best startups are great precisely because they’re targeting a strange combination of submarkets, or they’re in the early stages of creating a category, where there isn’t even an agreed-upon way of describing it yet. Conjuring TAMs for startups like this involves a mixture of alchemy and storytelling that can sometimes be unconvincing in the early days1.

For example, I’ve been building a low-code platform for field service organizations since 2011, but I’d never heard the term “low-code/no-code” (and we didn’t use it) until the mid-2010s sometime. Had we oriented on the “TAM” of no-code back then, what would we have determined? If you could even define a known boundary around the category at that time, it was probably in the 10s of millions or maybe $100 million total. Now the market is expanding at a CAGR of 30%, headed north of $180 billion by 2030, from around $10 billion in 2019. This market became a known one gradually over time. Initially it was just an undifferentiated, messy mass of people and companies doing things that looked similar to one another with app-builder tools, WYSIWYG editors, and pluggable integrations. Over time the ecosystem became legible and better understood, and now it’s a named category tracked by the likes of G2 and Gartner. But, importantly, some of the best investments in the space happened long before analyst acknowledgement. These are lagging indicators if you’re looking to be the first in, funding the most exciting new ideas.

But an even more important reason why TAMs are dangerous is that even if a market itself is relatively stable over time, your company doesn’t need to be stable. A company has agency. A great product team doesn’t stand still and let their market “happen to” them. Dimitri Dadiomov nails it here — couldn’t have said it better myself:

Part of the calculus with investing in an early product is measuring the future potential of the founders and the company. How a TAM is computed given the current status of a market, or the fitness of a product to said market, is irrelevant to capturing the future potential. A great product team will not stand by and let a better market, or a more focused market pass them by. In the best instances of this, in fact, startups can be singularly responsible for (or close to it) the creation of a market from whole cloth. Or at minimum they can greatly accelerate the realization of latent, obscured demand. Think iPad for tablet devices, Dropbox for personal cloud storage, Salesforce for CRM.

All of this is largely academic if you’re researching your market size to communicate with stakeholders. Take these tips for sizing and refining your definition and run just enough with them to communicate clearly. Just be wary not to internalize too directly the left and right bounds of your market. That’s not to say that defining ideal customer profiles is a bad thing… Far from it! But there’s a difference between “Alex here is the type of persona we’re building for” and “Our market is X big, and defined in this specific way.” Taking to heart what your market looks like without appreciating your own ability to change it can drive fatalistic behavior on the team. If your success in a market is flagging, or you’re making discoveries that the go-to-market angles into a specific customer set aren’t working, you have the steering wheel. You can change course, experiment your way into new markets, and make your TAM simply a snapshot of where you are, not a strict destiny.

  1. But the great angel and seed investors pride themselves on the ability to conjecture about a founder or an idea’s prospects. 

Architecture from Every Country

September 12, 2022 • #

This was a fantastic thread from The Cultural Tutor — so simple, but had me on an epic Wikipedia / Google Maps rabbit hole.

Some of my favorite examples:

Kind of sad to see so many overbearing modernist structures in here, but some of them are nothing if not impressive, at least.

His newsletter, Areopagus, is full of great tidbits on art, history, classics, architecture, rhetoric. Well worth a subscribe.

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