The Exchanges

Q Do you have a favorite product you have recently discovered that you love?

A I love my computer. I'm fast at my computer. Um, being fast on my computer helps me just go from intention to just out in the world. I've fallen back in love with Raycast, uh, which is a automation tool for those who have watched the journey of Spotlight and Quicksilver and Alfred and all these automator services. Raycast seems to have cracked the nut on Automation, nerd complexity, but also UI ease and some nice touches and just like loads quickly does the basics. It's fully programmable, extensible, just like a huge fan of Raycast. And then I think for product people, you, if you don't have clean shot installed for screenshots, you're just behind the curve. There's so being able to take a screenshot and blur particular things or point at stuff or have arrows and lines and just like have that be second nature, fast, instantaneous is so useful. To be able to communicate what you're seeing. So when I get a new laptop, it's Raycast first and CleanShot second.

AI assessment note: “I've fallen back in love with Raycast, uh, which is a automation tool”

Q things like that. I know there's some new stuff coming that you're going to share, but one last question about study groups, who, how do you decide what product you're going to pick to do a study group on? And then what is the expectation with the result? I imagine there's a PM sitting around like, oh my God, I just got this 10 page report on all the problems.

A So initially I just made up a list of stuff that I thought would be fun to study group to kind of kick it off. And now because it has a bit of an internal Brand and it's exciting. And people have gone to study group, say nice things about study group. They're, they actually proactively say, Hey, we should study group blah, or, uh, we're launching something next week. We should study group it before it goes out the door or. Now I actually just have a huge backlog of things to study group, uh, based on what people want. And then, and now we're kind of, again, franchising it. So we're gonna have study group captains and people around their own study groups. And so I can, we can really scale this behavior, but we did our first study group of an internal tool recently. And so that's, I think it's gonna catch on just any, anything at all can be study group. It just takes about an hour and a couple of people and you open up the zoom and that's it. And then for expectation wise, look, you can, It is, it is so tempting to put more regulation on something. Okay. Well, everything coming out of this program needs to be scored and rubric and have SLAs. That is extremely reasonable as some of these next steps, because we do notice things that are of serious issues and we You know, we have some formal processes inside of Stripe for elevating bugs to certain priority levels that get tagged and…

AI assessment note: “we kind of funnel the outputs of a study group into our already existing formal processes”

Q class that I'm potentially the worst at. This isn't how most people think this is how most people operate. Usually people want to get good grades. They want to be at the top of their class. Clearly you have a different approach and a different mindset. Where did this come from for you and how did this shape the way you think about product and the work that you do?

A Some of it was just the fact that I wasn't particularly good at the class and had to rationalize it for myself in some form. So, uh, in retrospect, that sounds kind of highfalutin, but at the time I just wasn't particularly good at the classes I was in, but I think it comes from Growing up, I went to a pretty hippy dippy K through 12 school in Baltimore, Maryland, where we were really Asked to think about why we were in school and to pick any of the courses that were of interest to us outside of AP programs or grades or any particular requirements. You really got to choose your own path, and I recall one particular class in high school, uh, which was, you know, sort of somewhat a science class, but it was called the History of Science, And we actually walked through and studied all of the, at the time, best understood ways the world worked in science, but then later were turned out to be wrong, right? In the 1500, we believed X, Y, and Z. In the 1600, we've A, B, and C. Just very confidently in 1500, we thought something, and then the 1600, they thought something very different. And so this class was quite impactful on me, where we spent an entire year Studying things that are not true, and it was fascinating, and that particular teacher employed another trick on us during that class, which was, um, he took the tuition fee of our school and divided it by the number of hours and…

AI assessment note: “I went to a pretty hippy dippy K through 12 school in Baltimore”

Q complicated stuff that people talk about in PM circles when the most straightforward, obvious thing is probably right. I get so annoyed after calls with Jeff sometimes because I know he's right about something. I bang my head against the wall for months. And so talk about just like what you've done, what you've learned about getting stuff done at a large company. What do you need to do right?

A Not having things be your idea. I think is really powerful. It's like, I just talked to 50 customers who all yell the same thing. Here they are in varieties of quotes and forms and the rest of it, and you put some three bullet points of strategy around why it's important and it's going to help you win more market share and the rest of it and how you can do it well. Cool. I mean, what else could we want to do? Maybe somebody has something where 51 people have the same burning thing, but The majority failure mode is we do nothing. That's the majority failure mode. And so, one, aligning people with deep customer stories, storyboarding some solution visually with a Sharpie and not a pencil, not Figma initially, not high or low fidelity. I can never remember which one is the detailed one, but just like Sharpie. What is the unconstrained perfect solution to this burning problem? And that's, you know, Pixar style storyboard. You don't need to be a designer. You can just draw like stick figures on a piece of paper or whimsical or whatever you want to do. And with those things, If you're not asking for, you know, this, the sun and the moon on headcount and team size to make some forward progress, like who could stop you? You know, let's get some first version working. It was very motivating to get that single piece of paper in the mail with, which was blank to kick us off on the 83, the…

AI assessment note: “Not having things be your idea. I think is really powerful.”

Q I feel like this is something a lot of people are starting to realize is really important and or are trying to get better at either personally or at their company. So first of all, let me just ask, why is, why is this so important to you? Why do you think craft and experience and quality is so important? Why do you put so much emphasis on it yourself?

A I think I'm really working backwards from failures in the past and avoiding them. And so maybe just a quick story. I had a, I started a company several years ago based on just a personal pet peeve of mine, uh, which was, I was a SQL analyst. Many of you listening might have written SQL in the past. Maybe the robots write the SQL for you now, but I still need to write a little SQL yourself. And every single time I Wrote a SQL query. I wanted to run the same subsequent analysis. I wanted great version control. I wanted all the cool stuff that GitHub had for code, but in a, in, in, but for writing data code. And so My friends and I built a little Python tool, which, you know, basically let you run R style queries. It lets you draw, uh, charts and pivot tables quickly and sharing all sort of all this modern SaaS application stuff, but applied to SQL a few years ago. And we turned that into a company. We got some progress, but then there was this moment one day where We had maybe a couple hundred customers and we had an error where we basically by accidentally shut down the service and it was sort of bricked for 10 or 20 minutes. And At the time, we were all kind of hustling in our little dinky office to get the application back online, and we really kind of were proud of ourselves about how reasonably quickly we did, and people went back to using it. It wasn't a super long outage, …

AI assessment note: “I think I'm really working backwards from failures in the past and avoiding them.”

Q great. I was actually gonna ask this technique of using silence to help people actually practice it. You just share this kind of quote of for you to pay 10,000 dollars, it would have to do X. That's a really cool line to use. Is there any other advice there? I've just had to practice this idea of creating silence to help the potential customer share what they actually need.

A I encourage people to take an improv training, improv training class, uh, or two, just to get people out of their skin a bit. By the way, this advice applies to big companies also, not just small ones. And we, we have issues and I hear other larger companies have issues where a big company will say, Hey, we, we're an enterprise and we're going to pay you this Big contract. All you need to do is build features. One, two, three, four, five, six, seven, eight, nine, and go through security steps, ABCD, EFG, and the siren song of the big three year contract of your first enterprise buyer. Even when you're already big, it's, there's always a, you know, you can go from fortune, 1000 to fortune, 500 to fortune, 10 to fortune one, you know, there's always more. There are so many stories in the rug being pulled in the middle and they never, they never actually use it and the contract never lands. Same in partnerships. And so I would say the same thing, which is like, if we're super serious about this, send us a million dollars. Like wire us a million dollars. We'll happily wire it back anytime you need it, but let's actually Put some stake in the ground about the value. And I find that in the cases in which they're like, whoa, wait a second. No, absolutely not. Uh, we can't commit here. That's really good signal because you're about to spend a huge amount of time building something that…

AI assessment note: “I encourage people to take an improv training, improv training class”