So I do have kind of an extensive questionnaire, so we just touch on a few things, but one thing I think first and foremost is, what are your values? And I think it's really essential to do some sort of values clarification exercise. You can find a ton of them online. You can find a list of values and just pull out your core values and just compare them with each other because when you are aligned, it's great. Or when you're adjacent, it's also great. I might care a lot about excellence, Lenny, you might care a lot about learning. Fantastic. Those are great values that we can kind of, go together. I might care about excellence and you might care about work-life balance. Wow, let's talk about that because I think it's going to be really important as we go through our startup journey that we understand both of us, what does work-life balance mean and what does excellence mean?

One of the founders I worked with, he would text or Slack his co-founder on weekends and the co-founder wouldn't respond. And that was extremely frustrating to the person, to the co-founder I was talking to. And it turned out, after they finally addressed it, it really was about wanting to have some downtime and some, quote unquote, "Balance."

I'm so great at bringing things up." But the person who's close to you might say, "You seethe until you're ready to bring something up and it's really uncomfortable in the seething period." So it just gives you a little more self-awareness about how you actually handle conflict.

The other person might be a person who totally wants to talk about the conflict but wants to let it settle first and wants to also go through their own thinking process about what's important to them and might actually feel like they've resolved it themselves without having to have a conversation with you.

And if you're the person who's like, "Let's talk about it, let's talk about it, let's talk about it." And they're like, "I'm working through it myself." Now you have conflict over the conflict and it just turns into dynamic that's not necessary.

While you might think turning a yellow spot into the sun is mainly about strong execution, it’s equally about inventiveness and vision. There are situations where I wouldn’t have been able to describe what the person ended up creating. I had a version of what “great” looked like in my mind—and they surpassed it in ways I wouldn’t have been able to articulate in advance.

Arielle because Balsamiq is a newsletter sponsor. She shared a story that’s an example of turning a yellow spot into the sun. Here’s what she said: “Something I did that completely changed my career in its early years: I kept a work journal. I noted down decisions I made as an IC and manager, decisions my managers made, the outcomes, the impact, and what I learned. I wrote down those "inside thoughts" we all have during meetings. I wrote down the advice I HATED and why, as well as the helpful stuff. I wrote down pivotal interactions with clients, peers, leaders, and direct reports. I wrote down specific phrases different leaders liked to use. It was almost scientific—I applied basic tactics I learned in science/psychology classes about field observation. I still reference that journal to this day.”

Most people in her shoes would have said, “I need a mentor. I need someone to teach me strategy. I need support. I need to ask execs to explain their decisions and get their feedback.” Not Arielle. Arielle took a little (i.e. the lived experiences she was getting on the job, like all her peers)—and she turned it into a lot.

There is no set of rules (beyond the first principles I cover here each week) to memorize. It’s the same foundational principles, like knowing your assets/levers/constraints, asking the question behind the question, thinking rigorously, etc.

Before you move on to the next shiny object, consider if you’ve really squeezed every last drop of juice from your current endeavor.

People celebrate the strategy at the beginning and the outcome at the end, but if you look more deeply, there was usually good decision-making and craft at each step, which layered up to greatness. That’s why turning a yellow spot into the sun isn’t only for dramatic projects. It’s equally about elevating stuff most folks think of as boring and small.

Keep an eye out for anything that makes you stop in your tracks, even small things. Note what makes it feel magical and add it to your mental swipe file.

Forget trying to decide what your life’s destiny is. That’s too grand. Instead, just figure out what you should do in the next 2 years.

Visuals can stir up feelings or paint a scene in an instant. However, they may not always nail down the details or explain things as clearly as words can. Words can be very precise and give you all the information you need. Yet, sometimes they miss that instant impact or emotional punch.

For each visual you add to your presentation, you should ask yourself “What does it really say?” And then check: Does it enhance the meaning of my message, or is it purely decorative? Does it belong at this point in my presentation? Would it be better for another slide? Is there a better image that says what I want to say?

Computers don’t feel, and that means: they don’t understand what they do, they grow images like cancer grows cells: They just replicate something into the blue. This becomes apparent in the often outright creepiness of AI images.

AI is really good at making scary images. Even if the prompt lacks all hints of horror kitsch, you need to get ready to see or feel something disturbing when you look at AI images. It’s like a spell. Part of the scariness comes from the cancer-like pattern that reproduces the same ornament without considering its meaning and consequence.

Placing pictures next to each other will invite comparisons. We also compare images that follow each other. Make sure that you do not inadvertently compare apples and oranges.

When placing multiple images in a grid or on one slide after the other, ensure they don’t clash in terms of colors, style, or resolution. Otherwise, people will focus more on the contrast between the images rather than their content.

Repeating what everyone can see is bad practice. To make pictures and text work, they need to have something to say about each other.

Don’t write next to the image what people already see. A caption is not an ALT text.

The most powerful combination of text and image happens when the text says about the image what you can’t see at first sight, and when the image renders what is hard to imagine.

Do not be boring or overly explanatory. The visual should attract their attention to your words and vice-versa.

If a visual lacks meaning, it becomes a decorative placeholder. It can dilute your message, distract from what you want to say, and even express disrespect to your audience.

There are four signs your idea has legs:People pay you money: Several people start to pay for your product, ideally people you don’t have a direct connection toContinued usage: People continue to use your prototype product, even if it’s hackyStrong emotion: You’re hearing hatred for the incumbents (i.e. pain) or a deep and strong emotional reaction to your idea (i.e. pull)Cold inbound interest: You’re seeing cold inbound interest in your product

Every prosumer collaboration product, including Figma, Notion, Coda, Airtable, Miro, and Slack, spent three to four years wandering in the dark until they stumbled on something that clicked.