The Wisdom Wall

“in, in some ways, listen, for some, for some practices hallucination, hallucination is a bug, but in some areas it's also a feature, right? So if I'm trying to discover some cool new music, I mean, I can imagine that might be a feature as opposed to a bug. You know, when you're trying to do generative fill in Photoshop…”

“Actually, I think that's, that's sort of the right answer is you should build models if you're the best company in the world to build them.”

“I do think we executed well, but I also think that there's some nuances of this, this platform shift in particular that do favor those companies that know their customer well and already reach them.”

“I think you should abstract yourself out of almost every function. Except for the one that is your superpower, that you are the unique person in the world to do, and you should keep doing that as long as humanly possible.”

“we can't celebrate fake wins. You know, I see some teams celebrate financing, celebrate getting an award that frankly they paid for, or getting some press coverage that they clearly paid for, and that is dangerous because what you're doing is you're getting the team to Celebrate non-productive action.”

“I actually never try to ask Tam up front. I never try to think about the existing market, because when you're a seed investor in the early stage, at least I feel like I'm in a business of exceptions.”

“And, uh, and those companies oftentimes fail and they fail because they never build the muscle memory, the instincts around how to mine difficult moments, how to run postmortems, not because you want to, but because you need to, because you can't screw this up again or you're dead. There's a sense of resourcefulness…”

“I think one thing I also learned from the team is that it's not a scalable business. I've always admired how the team over the years has defied many of the spotlights of seduction, whether it is building an online database or a website for a Entrepreneurs to use, or making the team much bigger, raising much bigger…”

“The failure of the first mile for most products is that the teams fail to remember that every user in his or her 15 seconds is lazy, vain, and selfish.”

“it's not the technology that makes us successful. It's the user's experience of the technology that makes us successful. And that's why I think the role of designers is more important, not less important in this modern world.”

“I think you should abstract yourself out of almost every function, except for the one that is your superpower, that you are the unique person in the world to do, and you should keep doing that as long as humanly possible.”

“I believe that some of the initial product reviews should only be with the product and design team, because engineers are really there to discuss the cost of something.”

“intuition is what brings you to a mountain to climb. Data is what helps you climb it.”

“every customer, at least initially in their 1:30 seconds of a product experience, is lazy, vain, and selfish, right? You know, you don't want to read stuff, you don't want to watch a video, you don't want to take a tour. You kind of want things done for you.”

“first of all, I believe that some of the initial product reviews should only be with the product and design team. Engineers are really there to discuss the cost of something, but how can you reconcile the cost of something while you're actually first starting to think about what we actually want to do, what's best for…”

“You know, even when it comes to the speed and performance of a product, you know, design is actually oftentimes a solution before engineering is a solution, just based on the fact that sometimes you have to replatform something, right? Sometimes you have to change the, an underlying service when in fact, with design,…”

“I think that's a mistake most leaders do, because you hire an all-star, and then you're like, oh, she's an all-star. She'll figure it out, when in fact, if she's in a great team, you know, the team needs to adjust in order to accommodate her.”

“The competitive advantage of most businesses is that they stick together long enough to figure it out.”

“I love the idea of building a splash page before even building a product of thinking about the brand language and the typography and just the one liners of value proposition before starting to build the product. Because to me, these are parts of your compass for all of the most important decisions that you'll make.”

“the greatest investments typically made markets as opposed to, like, We've exploited a common knowledge, large existing market that everyone's excited about, and in order to make a market or expand a market vastly beyond what it is, it has to fundamentally change something in human behavior, in pricing availability, in…”

“I think I believe more in initiative over experience, and I think that there's just, everyone's obsessed with resumes, and everyone's obsessed with what the experience is Someone has and how those can help them be the most effective leaders in something new. And I've in fact found often the opposite, you know, it's an…”

“these companies aren't necessarily great candidates for venture capital backing. However, they have a much lower risk ratio than a lot of typical venture backed companies. So the expected outcome is maybe smaller, but the risk is lower, which may be called into the need, a new class of capital.”

“I think as an earlier stage angel seed investor, it's all about investing in the potential of a product or the potential of a team. When you start to do more traditional venture capital And certainly venture capital at the benchmark level level. It's a lot more, or it's also about momentum because, um, you know, there…”

“oftentimes the trouble with momentum also is that when something has too much momentum too quickly, in my experience, at least it tends to fade out.”

“UI in some cases should disappear, but there's new UI these days in the form of the tone of a product and the way that something is, um, is the inflections that are used, the persona. You know, I'm, I'm like thinking about UI design in the future as in some ways like persona design.”

“a product always speaks to the DNA of the team behind it. You can tell who wasn't talking to one another, you know, what the values were, whether there was a designer outsourced, or in the room, sufficiently empowered, etc.”

“I deeply, deeply believe in the fact that a prototype is worth a hundred meetings, and if you can have a discussion around a PowerPoint with bullet points and stuff, I mean, you're gonna miss so much”

“I mean, life cycle, the life cycle of a product is somewhat perverse. It starts simple, And all these people, you know, flee the products they're using because they're fascinated by this new simple alternative on the market. And so customers flock to a simple product. That simple products takes all of its users for…”

“What few teams realize is that every new cohort of new customers is increasingly pragmatic. You know, needs a different type of first mile experience.”

“a prototype is worth a hundred meetings. And if you can have a discussion around a PowerPoint with bullet points and stuff, I mean, you're going to miss so much. You're going to have unnecessary disagreements and debates, and you're not going to have everyone aligned on where the flag is planted in terms of the…”

“I think most companies, you know, suffer from a lack of alignment because they talk about generalities, but they're not all really anchoring on the exact experience we want to enable for customers.”

“I am maniacal about capturing things during these conversations. So, you know, if there's a piece of feedback shared, but I don't see the pen move of the designer that's on that area, you know, I will say, like, did you capture that? Because I feel like that's the difference between success and failure.”

“You should not try to do those things for launch. You should not try to do those things before you have product market fit. It's really important. They're great ideas, but just do them later. The things you need to do now are the things that would get in the way of someone finding enough value and success to even have…”

“And if you can just get people through that first mile and then get them to some level of success quickly, you are already in like the top 10% of products out there.”

“intuition is what brings you to a mountain to climb. Data is what helps you climb it.”

“when you build that MVP and put it out there, you should be iterating based on data from there on out until the next big transformation where you have to lead with some intuition.”

“I love not only a prototype of what you're building now, but even a reachy prototype of what you believe the world will look like in three years with your product, because then it's like an anchor. It's like, okay, that's our conviction over the long term. Let's not do anything yet that doesn't yield that.”

“You know, I mean, listen, you have to set metrics, objective metrics, of what you believe progress looks like up front for a few different reasons. First of all, you know, as the messy middle Is you get lost in it, right? And along the way, the progress you're making sometimes won't feel like progress because it's…”

“there are different types of product leaders for different stages of a product. You know, some are very comfortable being very design-driven, setting a product strategy, a vision, rallying the troops around this, and ensuring that the experience is exactly what it needs to be, whereas others are more of the data-driven…”

“I feel like a product Always speaks to the DNA of the team behind it. You can tell who wasn't talking to one another, you know, what the values were, whether there was a designer outsourced or in the room sufficiently empowered, et cetera.”

“The reason that most products are 30 degrees off of what the customer needs, or more, and fail to really achieve that product market fit where it just sings, right, is that we're not shoulder to shoulder with customers enough.”

“I think we focus too much on hiring talent and not enough on grafting talent once you've hired it.”

“You know, startups have the opposite problem. They are working on the most novel news Stacks of technology. They're all building, you know, web apps or AI natively, et cetera. However, they don't have any top of funnel, whereas Adobe has this massive top of funnel, but is making the transformation in terms of the…”

“Well, you know, sometimes people posit it as, Customer happiness and usage versus revenue. When in fact, you know, they should be designed to work together. And the narrative, especially in an early stage venture, you know, needs to be about how one leads with the other.”

“Listen to their problems, but not their proposed solutions.”

“Hiring too quickly and hiring people like them as opposed to people that compliment them.”

“I actually feel like I'm a better investor in the early stages of products by being in the craft as well”

“I actually feel like happiness is very correlated with utilization. When you feel like all of your interests and curiosities and skills, when you feel like a number of different things you're doing in your life truly utilize everything about you that you want to develop and that you're proud of, I think you're in your…”

“how do you hire people, and how do you find which teams to invest in, and one of the things I always apply is, is this someone whom every conversation is more interesting than the one before it, or is it a replay? You know, most people we actually meet, I don't know if you have any people in your life where you go out…”

“I think great leaders are very good at merchandising progress to their teams. They're not manufacturing it. It's not fake. It's real, but it requires repetition that's unnatural. It requires also some marketing.”

“The litmus test for me is always, how will they perform as recruiters? Will people want to work for them? Are they going to teach and mentor people? The people that are coming up in the team. You can make any rationalization for why someone could stretch and fill a role, but if that person is not going to become a…”

“Now, knowing what I know, then quit just because you have venture capital, just because you have a team, you should not keep doing something you don't have conviction in. I have never seen that work.”

“And so I actually believe that teams should identify the one or two things that they think are most distinguishing about their product and they should do it themselves. They shouldn't outsource those things.”

“Users flock to a simple product. They get so excited by something new, novel, simple, shiny, and then that new simple product that enjoyed its launch on product hunt and, you know, has all this really great simplicity that people are compelled by. That new product takes its new users for granted, starts to add features…”

“We'll spend years building a product, and then we'll spend the final mile of our period building the product, like the last few months, thinking about things like the tour and the onboarding and the default user states and everything else. And so in ultimate irony, the last mile of our time building the product is…”

“As product teams, we need to constantly prioritize the newest users experience and recognize that newest user changes, like different cohorts and newest users need different things. And that is, I think, the secret weapon in a product organization to sustaining simplicity over time.”

“I mean, there are certainly stages of certain businesses where they should raise a war chest. Because of the nature of the competitive climate, they've already found product market fit. You know, now it's a, it's a race for globalization, or it's a race for acquiring customers in a market, and you just can do the math,…”

“Well, I think when you're bootstrapping a business, you get a tremendous feel for the granularity of your business, the money coming in, the money coming out, the true cost of every decision that you make. And it's a very healthy way to build a sustainable business because you feel in real time the impact of every…”

“Venture capital and investing in general is a business of exceptions, and whenever you talk to any, uh, seasoned investor about some of their greatest hits, you know, they'll tell you that the Team didn't look right, or the market seemed too small, or, you know, there are a lot of things that struck them as off-putting…”

“Entrepreneurs struggle because they are always focused on that long-term gain from using a product, and they're always trying to get people invested in the product in order to get that benefit, when in fact, they should just be focusing on the first mile.”

“if you get the first mile, the onboarding, the initial user experience of a product perfect for a period of time, you have to continually revisit it and optimize it for new groups of new users with different psychographics, you know, different expectations, different ages.”

“there are three questions you should ask in every screen you look at to ensure that it is accessible and navigatable for new customers. Right? The first is, how did I get here? What do I do now? And then what do I do next?”

“as humans, we typically just take and stick with the default of every experience that we're given. Wherever I land you is where you stay. You know, whatever I outfit you to use in the product by default is what you keep.”

“making a simple product that's great is one thing, but keeping it simple is an entirely different thing”