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How do the rules of positioning apply to independent software businesses?

It used to be that you would build something and people would use it. But it’s not enough to just make a tool that works anymore. That’s where positioning comes in, or the process of making your product stand out in a competitive market.

In this paid lesson, we’ll be going deep on how to apply a simple positioning to independent software businesses. If you’ve never gone through this exercise before, start here.

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#217
July 17, 2025
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Post-LLM value-based design

Over the past two weeks, we talked a little about the high-level view of post-LLM design and how buyers view design now. Apparently “the nickd take on LLM” resonates, since all of my opinions are universally correct and many of you are wondering how to move going forward.

I’m going to write a little more today and a little next week, and then we’ll get back to our regular programming, because (despite what you may have heard) there’s quite a bit more to value-based design than how we respond to LLM. In the meantime, I might package some of my thoughts on post-LLM design into a smaller offering. Hit reply if you might be interested.


“Post-LLM value-based design” is a bit of a mouthful, and it’s also inaccurate, because value-based design is an evergreen principle that responds to conditions.

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#216
July 15, 2025
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How do you write & adapt long primary CTA text?

Presumably, your home page has a masthead, and that masthead has a button for someone to get started using your product. In this lesson, we’ll talk about how to write ones that get a little… wordy.

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#215
July 10, 2025
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How are buyers of design treating LLM?

Our monthly office hours for paid members is today! Join us at 1p Central Time to chat about all things value-based design. Happy to answer any questions or pressing issues you may currently have. Find out what 1p Central Time is in your time zone here. If you’re a paid member, our meeting link is at the end of this email. If you sign up between now and 1p, we’ll send the meeting link your way.


In last week’s letter, I wrote about the world we exist in as designers after LLM’s broad-scale introduction. Now I’d like to talk a little bit about the labor aspects of LLM, which are, like it or not, heavily influencing those who buy design as of press time.

There’s a lot of noise out there. Almost all writing on this topic is unreadable. I sort of get why people are getting loud, though, considering western civilization is slowly collapsing and nothing feels remotely safe or permanent anymore. Kinda makes sense why people would think LLM is a cool safety blanket of future-forward manifestation, eh?

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#214
July 8, 2025
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How can social proof be used as your headline?

First, our monthly office hours for paid members is coming up! Join us on Tuesday, July 8 to ask me anything about value-based design & getting an impact with your work. These vary in attendance from 1 to 10 people, and they’re always helpful for you and for me. Signup link after the jump!


First, two stories about how social proof can be put in your headline. Then, a lesson about why and when you should do so.

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#213
July 3, 2025
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Initial notes on post-LLM design

Our prices on new consultative work will change at 5p CDT today. Now’s your last chance to buy a teardown, roadmap, or call with us at our current rate. If you’re an active client, your fees will not change for the duration of your work with us.


A couple of weeks ago, I surveyed everyone about what we should write about next, and “post-LLM design” won by a landslide. I find this to be fascinating, because we’ve positioned ourselves rather firmly as skeptical of LLM, at least with respect to some of the messaging that exists around it.

For the first half of my career, tech was changing the world, and there was a lot of optimism & promise around it. We didn’t really question much. The iPhone came out, then we all made a bunch of apps, then we ruined taxis & hotels. The internet was a place where we could all connect with one another and understand the world’s information. Twitter had infighting, but we thought it was funny.

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#212
July 1, 2025
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How is design surviving?

We already established that design is not dead. In this paid lesson, we’ll discuss the specific ways that design is surviving, alongside some steps for you to take.

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#211
June 26, 2025
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Is design dead?

No.

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#210
June 24, 2025
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How do value-based designers address ripoff designs?

Asking for design input from a wide range of stakeholders has its upsides and downsides. One downside is when someone sees a large company or influencer offering a specific solution, and they think “well, we should do that, too.”

On face, this is not a horrible idea. Other people did all of this work and succeeded, so why not us? It’s more efficient, helps us compete.

You know better, so let’s talk about it.

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#209
June 19, 2025
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Notes on fiat plays

Some business announcements this week, and then a brief note on fiat plays:

  • Our repositioning is more-or-less complete. If you find anything on our site that looks off or requires a rewrite, please let us know.
  • We’re kicking off a major summerlong project on the topic of onboarding, and I’m doing a small literature review for it. I’m already intimately aware of Hulick’s work, but if you have any other books or resources for me to review, hit reply and point me to ‘em.
  • For the first time in five years, we’re going to be changing our fees for new work in a few weeks. Since we could change it all right now, that means a lot of things are on sale as of the conclusion of this sentence. Now would be a very good time to book a roadmap, call, or retainer, if you feel so called. Thanks for your support of us, now & always.
  • Lastly, one brief question: what would you like me to write about next?


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#208
June 17, 2025
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How do you start to apply consistent design to your product?

In last week’s paid lesson, we defined the seam and discussed what you can do to address it. We’re building on that lesson by talking about why a style guide is important, and what makes it different from a design system.

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#207
June 12, 2025
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Move slowly & fix things

Our monthly office hours for paid members is today! Join us at 1p Central Time to chat about all things value-based design. Happy to answer any questions or pressing issues you may currently have. Find out what 1p Central Time is in your time zone here.If you’re a paid member, our meeting link is at the end of this email. If you sign up between now and 1p, we’ll send the meeting link your way.

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Financially, we have something here called the breakeven point, where we know we’ll be able to live comfortably, meet our expenses, and do what we want to do for the year. This typically comes around late August, when a lot of businesses lock in their strategies for the rest of the year and have chosen to get us involved. A couple of years, it didn’t happen at all. One year, it happened in early June because everybody suddenly invested in our work in response to a global pandemic.

I don’t want to jinx anything, but it’s nonzero likely that we’ll reach the breakeven point soon. Our existing client portfolio has not changed since last September, and a couple of them have chosen to hire us for more expansive work. With one more renewal, we’ll be good for the year.

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#206
June 10, 2025
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What is “the seam,” and what can you do about it?

Have you ever signed up for software that had a lovely-looking marketing page, and the product itself was… lacking? We call the transition between marketing & product the seam, and we think it’s of profound importance for your business.

A prominent seam results in lower retention and higher churn, plain & simple. Competitors can take advantage of it. And it’s just not a good look.

That’s because your marketing page promises something, and so your customers expect the quality of your design to translate, in some form, to the product. When someone goes through a well-designed conversion funnel, joins, pays you, and encounters something that looks like it was built ten years ago, they feel deceived.

In this paid lesson, we’ll discuss what the seam is, where it typically occurs, why it occurs, and what you can do about it.

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#205
June 5, 2025
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What is the goal of the independent consultant?

First, our monthly office hours for paid members is coming up! Join us on Tuesday, June 10 to ask me anything about value-based design & getting an impact with your work. These vary in attendance from 1 to 10 people, and they’re always helpful for you and for me. Signup link after the jump!


I’m currently writing this in my garden, which is the sort of place that causes people to go slack-jawed and slow down as they walk through. I garden a lot. I pull weeds on my way inside and throw them in a little basket next to the door. I harvest plants from my raised bed and make lunches from them.

I pause for lunch every day. I make lunch every other Thursday for anybody who wants to show up. I’m sitting under a 12-foot-tall serviceberry bush right now, and in a couple of weeks its fruit will start to ripen, at which point I’ll be swatting squirrels & birds away as I pick the thing clean. Then I’ll make jam with it, jar it for my close people, and hand the jars out exclusively at my biggest party of the year, which is on the second Saturday of July.

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#204
June 3, 2025
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What will happen now that design has won?

Incorrect people have recently been declaring the death of design. This is weird, because we see design everywhere. We see design in places where we don’t expect to find design. We can only conclude, in this moment, that design has won.

So what now?

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#203
May 29, 2025
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Sometimes positioning hurts, so make it hurt good

One more about repositioning.

We often speak here about new positioning being easy to adopt, technically speaking. You change your home page, spin up a landing page, ask people if they’re interested. You put on new positioning like it’s a new outfit.

The real challenge is when you reposition after a decade of a previous positioning. That’s a fourth of your career! You’re kind of flushing it! Suddenly you’ve been boiling-frog’d into one of the most load-bearing decisions of your life.

There are ways to slow-pedal this and soften the impact. If you keep your existing portfolio of clients, and even your existing messaging and educational initiatives, you can test the new market without burning any bridges.

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#202
May 27, 2025
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What tiers should your pricing start at?

Expanding on our recent universally correct lesson about pricing, we’d like to talk about pricing tiers: namely, what goes into the strategies behind establishing each price, and what you can do to move into a correct space for pricing.

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#201
May 22, 2025
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Notes on delegation

Thanks for your patience while we were out in sunny, profoundly warm Mexico. I watched a thunderstorm roll in while drinking coffee on my balcony, overlooking the Caribbean, and I felt really grateful to be alive, doing what I do for all of you.

A few small announcements:

  1. I’ll be doing teardowns at MicroConf Remote tomorrow, May 21, in the morning. MicroConf is one of those extended-family things that I’ve been honored to attend over the past few years, and I’m really grateful to be on some form of stage for them. Please come through & heckle!
  2. I was quoted on the App Collective’s latest episode on the topic of how we vet trusted partners. Don’t call us, we’ll call you.
  3. Not a Draft-y thing, but we enjoyed this A/B test. Not a very high sample size, but you’re dividing by zero, so.

Okay, actual letter time.

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#200
May 20, 2025
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Office hours today

Our monthly office hours for paid members is today!

Join us at 1p Central Time to chat about all things value-based design. Happy to answer any questions or pressing issues you may currently have. Find out what 1p Central Time is in your time zone here.

If you’re a paid member, our meeting link is below. If you sign up between now and 1p, we’ll send the meeting link your way.

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#199
May 13, 2025
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Open questions in software marketing

As a humble reminder, we’re out at a conference this week. We’ll be back the week of May 19.

One of my favorite things about software is how there are so many bespoke cases that people end up with these roiling debates about how to do a thing. “Don’t charge less than $50 a month,” one says, forgetting that this is literally how dozens of thriving businesses work. “Never have a free plan,” they say, even though many businesses, including one I work for, use free plans as ways to cleanly ladder people into revenue generation.

And so there are still quite a few open questions. These are “myths,” I guess, to some, but for us they’re rules that just happen to get broken a lot. Let’s go through some of them, and outline some exceptions and contingencies.

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#198
May 8, 2025
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