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Lessons from going freemium: a decision that broke our business

In Lessons from going freemium: a decision that broke our business, Bobby Pinero (CEO of Equals) makes some interesting points about what they’ve learned about freemium pricing models. This point about how user friction is not always a bad thing stood out to me:

In all of our pursuit of getting people into the product, the thing we forgot is that the goal of onboarding is not for people to complete onboarding. It’s not to just get people into the product. The goal of onboarding is for people to get their first moments of value from your product. To get “activated.” And removing friction is actually detached from this goal.

Just like everything in product, this all depends. Every business is different. But it’s nice to see things from another perspective

You are probably not one feature away from success

I like this perspective from Ed Sim on recognizing that you can’t always build yourself into product-market fit…

There is no easy answer for a lack of customer traction, but my one suggestion before you commit to the idea that you are one feature away from success, is to go back to the basics and first ask if this is the right user or customer. If you believe you have that nailed, try multiple messages and keep learning from every interaction. You may have the right product today but for the wrong user. Or you simply may just have a cool technology in search of a problem to solve in which case you should start completely over. 

The 10x Exercise for Entrepreneurs

I don’t like the “10x” terminology in tech, but The 10x Exercise for Entrepreneurs is not that. It’s about a thought exercise for entrepreneurs as they start to reach product-market fit:

What does our employee org chart look like with ten times the scale? What will our customer mix look like at ten times the revenue? What types of funding sources and capital stack will I need to fund the growth of the business to achieve this scale? What types of partnerships, infrastructure, and geographic locations will be necessary to 10X the business?

Still uncool, but finally useful

I wholeheartedly endorse the RawSignal team’s take on performance reviews:

A great performance review is not an evaluation conversation, it’s an alignment conversation. It shouldn’t be a conversation about which things happened, it should be a conversation about which things matter. It’s an opportunity for you and your person to get onto the same page about where you’re seeing the work differently, because that is informative in terms of how the next year is going to feel.

Algorithms Hijacked My Generation. I Fear For Gen Alpha.

This is a bleak take, but I have to admit that I am also concerned.

I believe we have some personal agency. I also believe that a 12-year-old’s mind is no match for a giant corporation using the most advanced AI to manipulate her behavior. Gen Z were the first generation to have our vulnerabilities and insecurities fed into a machine that magnified and refracted them back at us before we had any sense of who we were.

Link roundup for November 8, 2023

It’s been a bit quiet on the blog lately, so I thought I’d bring back the link roundup thing I used to do quite a bit. Here’s some stuff I read and enjoyed recently outside the regular product/business topics I usually write about here…


Very good summary of The OpenAI Keynote by Ben Thompson. This bit stood out to me:

The fact of the matter is that a lot of people use ChatGPT for information despite the fact it has a well-documented flaw when it comes to the truth; that flaw is acceptable, because to the customer ease-of-use is worth the loss of accuracy.


I’ve been following Craig Mod’s work for over a decade and know what to expect, yet his reflections on “Aloneness” took my breath away.

The real shitter is that if you’ve inured yourself to living in this state of aloneness, it can be difficult to break the habits that have led to it. Aloneness as default becomes comforting, and habits built around aloneness feel palliative because they’re known, and we tend to repeat familiar actions, even if they hurt us.


Great essay by Anne Helen Peterson on how friendship changes over time—including a period she calls “The Friendship Dip”:

Right now, the way our society is organized, we have a prolonged stretch of adulthood that is not conducive to forging or sustaining friendship or community. In many cases, I’d say it’s actually hostile to it.

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Everything about the new U2 show sounds amazing. So sad I don’t have tickets.

Zoo TV had predated reality TV, fake news, social media—all these things. Bono had heard about this new venue in Vegas with nearly 20,000 seats, custom sound and an incredible screen that was akin to the whole audience having a VR experience. In the post-Covid era, it was appealing not to have to travel every night


Every new house in Portland uses this font for the house number, and now I can’t get this article out of my head. “The gentrification font: how a sleek typeface became a neighborhood omen”:

As Neutraface house numbers have become too commonplace to ignore, some now associate them (along with gray paint jobs) with neighborhoods overtaken by construction and renovations.


Feels like spam is about to get a lot harder to detect… “Inside the Underground World of Black Market AI Chatbots”:

We’ve got folks who are building LLMs that are designed to write more convincing phishing email scams or allowing them to code new types of malware because they’re trained off the code from previously available malware.


And finally, for my fellow Northerners… “How to light the dark months” has some excellent advice—not just the normal stuff we’ve all read a thousand times.

Lighting winter is an art and a daily practice, an act of survival and a gesture of love. Here are 10 ideas for fighting the gloom in the dark half of the year.

When To Hire Your First PM

Good advice here on when (and when not!) to hire the first product manager in a startup. This is also a good reminder to “let PMs be PMs”…

PMs are the strategy arm of this process, and should be empowered to own the roadmaps for how they’ll better the business, not just the execution of getting things built. In an ideal world, PMs will have better decision-making and execution than you within their domains due to focus and proximity to customer needs. This is how you scale. If you continue to hold all of the strategic decisions close to the vest and use PMs as glorified interns, you’re wasting all of the focus that they could be bringing to bear.

2023 State of DevOps Report: Culture is everything

There’s some good insights in this year’s 2023 State of DevOps Report. It’s well worth skimming through. Things like this aren’t exactly surprising, but it’s nice to have some data around it:

Teams with generative cultures, composed of people who felt included and like they belonged on their team, have 30% higher organizational performance than organizations without a generative culture.

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