The Exchanges

Q massively rising prominence of design won. We've also seen another trend, which is the massive rise of deep tech and kind of core tech, be it machine learning, uh, and all that surrounds that. Are those two fundamentally compatible, do you think? Because deep tech and design Often viewed by VCs as kind of fundamentally different in terms of one is the core underlying tech, and one is the wallpaper.

A Yeah, no, they absolutely should go hand in hand, and I think the best companies are where those two things do come together, where you kind of have this deep technology. You know, even, I'll take Facebook as an example, right, their, their newsfeed algorithm is, is amazing tech, right? However, if it's not married with a great user experience, or if, It's not being considered as what is the, what is the purpose of this thing? What is the type of society that we want to create? I think just having a great AI is not going to be enough. You need to actually like also marry that with great research, great product design, make it useful. And you've seen companies where they have a similar feed or similar feed technology that doesn't work as well because the design of the thing, meaning how it works, how you interact with it is not as effective. And so, You need those two things to come together, and I think when those two things come together, that's when you have really beautiful outcomes. I think Tesla's another great example, right? It's like the technology in Tesla vehicles is amazing, but also the design of the product and the way it works and even just the aesthetics make it something that's best in class.

AI assessment note: “Yeah, no, they absolutely should go hand in hand”

Q a, is it quite that binary as good or bad? And is it not a matter of subjective belief in, in what makes one good and what makes one bad? You know, the Chinese have very different, uh, preferences towards UI than Western cultures where we're much more clean and generous. How do you view that kind of subjectiveness with design? Are products good or bad? Is it that binary?

A I think definitely there's, there's a gradation, right? Everything is like, uh, there's a gradation. And I think also there are so many different layers of Consideration when you think about is a product achieving its goal? So great products, they probably have different goals, right? There's business goals. There are goals for the end consumer. There are goals for society, right? Ideally, all those things are aligning beautifully where if a business does well, and if the product does well, then people get what they want out of the product. And actually we, the output is a better society. But Not many companies have all those things aligned. I'll get like a great example from the designer fund portfolio. We have a company called Omada Health, which is a diabetes prevention platform, and what they've done is they've built a product that mimics landmark research that shows that there was a program that if you, for 16 weeks, join with a cohort of other individuals, with a coach, and go through that program, then basically they can get you off the path To diabetes. And so, they put that program online, and they've actually seen better efficacy for that than the brick-and-mortar program. For companies that pay their own healthcare, paying for employees who are at risk of diabetes to go through the program can be a huge financial win for those companies. And if the product does well,…

AI assessment note: “I think definitely there's, there's a gradation, right? Everything is like, uh, there's a gradation.”

Q I think that's product market fit if there ever is one, but I do, but, but I do, I am really intrigued. I mean, you know, I've never had a designer turned VC on the show, so I'm super intrigued to hear how does your design background then inform your investing and how you really support companies?

A In terms of our design background, helping to support companies, there's a couple of ways. So One is as a designer that's built products at Facebook, and then before that, I actually worked at agencies, and so I've built products for a lot of companies, so I actually know what makes a great product and what makes a bad product, because I've built them before, and so we can actually, we have a better sense of that. Additionally, we look at, just because you have a great product now, doesn't mean you actually have a good replicable process that you can continue, and so not only do we look at, can this team Do they have a great product now? Do they also have a process to continue to produce great products going forward? Because one of the things that we're realizing this idea of like product market fit as a thing that you either have or don't have, it's not really true. That's not really the way it works. You can get closer to product market fit and product market fit is this thing you should be continuously striving to achieve. And so we want to see teams that have a replicable design and product Process to continue to iterate and continue to build a product that is, you know, that has that product market fit, if you will, over time. And so that's number one is that we're, by being designers, we're able to recognize that. And the second thing is we actually treat venture as a ser…

AI assessment note: “In terms of our design background, helping to support companies, there's a couple of ways.”

Q massively rising prominence of design won. We've also seen another trend, which is the massive rise of deep tech and kind of core tech, be it machine learning, uh, and all that surrounds that. Are those two fundamentally compatible, do you think? Because deep tech and design Often viewed by VCs as kind of fundamentally different in terms of one is the core underlying tech, and one is the wallpaper.

A Yeah, no, they absolutely should go hand in hand, and I think the best companies are where those two things do come together, where you kind of have this deep technology. You know, even, I'll take Facebook as an example, right, their, their newsfeed algorithm is, is amazing tech, right? However, if it's not married with a great user experience, or if, It's not being considered as what is the, what is the purpose of this thing? What is the type of society that we want to create? I think just having a great AI is not going to be enough. You need to actually like also marry that with great research, great product design, make it useful. And you've seen companies where they have a similar feed or similar feed technology that doesn't work as well because the design of the thing, meaning how it works, how you interact with it is not as effective. And so, You need those two things to come together, and I think when those two things come together, that's when you have really beautiful outcomes. I think Tesla's another great example, right? It's like the technology in Tesla vehicles is amazing, but also the design of the product and the way it works and even just the aesthetics make it something that's best in class.

AI assessment note: “Yeah, no, they absolutely should go hand in hand”

Q Now, as you know, I do interview many, many VCs, and it's really the first case at Probably where you really do treat venture as a product in implementing those, uh, the software that you've built personally. I'm intrigued, though, how that means you view the current crop of VCs and how they view design first. How is that for you when you look at the scene?

A Yeah, so I'm, so I think one of the trends, I do think that more and more VCs value design. We are seeing that, and I think that's great. You're seeing more designers join VC firms as design partners. And I think we're seeing more interest from designers. There's a lot more designers being angel investors, and I think we'll see more designers wanting to be actual investment partners. So someone, you know, like Scott Belsky or like Jeff Veen. So we're seeing that that happen. At the same time, I think there is still a vast majority of investors who view design as this thing that you kind of add on after the fact, or that is, you know, kind of a visual layer that is not necessarily available. A necessity in building a company, and we want to get to the place where, you know, great design, great engineering, and great tech are table stakes in terms of building a great startup going forward, and so that's the world that we want to see, and that we want VCs to move forward into, and so a big part of what we do is try to be huge evangelists for design, and whenever we meet with other investors, whenever we meet with founders, kind of continuously champion The value of design and kind of show its, its effectiveness in building great companies.

AI assessment note: “I think that more and more VCs value design.”

Q I have to say, I subscribe to all of them. They are, they are my favorites too. But then, but then design-led founder you most respect and admire?

A I guess it's cliche, but Joe and Brian at Airbnb, right? The company, Airbnb is by no means, you know, a perfect company, but The way that they've instilled design in every aspect of that company, and the risks that they've taken, and put that company in a position to just be one of the great companies in the last, you know, 1020 years is amazing. And then, kind of, the new one, and, you know, over time, I've really come to admire what Evan and Snapchat are doing, because I think they're a very non-Silicon Valley approach to company building. They just do things that are Fun and wacky and silly, you know, things that, like, uh, you rarely see Silicon Valley firms do, right? Companies do. They tend to be very rational and logical and growth-oriented and metric-oriented, and Snapchat just think, they seem to just do things just because. It's like, we're doing it just because we can, and I think there's something to that. I think a lot of Silicon Valley companies can learn from that style.

AI assessment note: “I guess it's cliche, but Joe and Brian at Airbnb”

Q I think that's product market fit if there ever is one, but I do, but, but I do, I am really intrigued. I mean, you know, I've never had a designer turned VC on the show, so I'm super intrigued to hear how does your design background then inform your investing and how you really support companies?

A In terms of our design background, helping to support companies, there's a couple of ways. So One is as a designer that's built products at Facebook, and then before that, I actually worked at agencies, and so I've built products for a lot of companies, so I actually know what makes a great product and what makes a bad product, because I've built them before, and so we can actually, we have a better sense of that. Additionally, we look at, just because you have a great product now, doesn't mean you actually have a good replicable process that you can continue, and so not only do we look at, can this team Do they have a great product now? Do they also have a process to continue to produce great products going forward? Because one of the things that we're realizing this idea of like product market fit as a thing that you either have or don't have, it's not really true. That's not really the way it works. You can get closer to product market fit and product market fit is this thing you should be continuously striving to achieve. And so we want to see teams that have a replicable design and product Process to continue to iterate and continue to build a product that is, you know, that has that product market fit, if you will, over time. And so that's number one is that we're, by being designers, we're able to recognize that. And the second thing is we actually treat venture as a ser…

AI assessment note: “In terms of our design background, helping to support companies, there's a couple of ways.”

Q Now, as you know, I do interview many, many VCs, and it's really the first case at Probably where you really do treat venture as a product in implementing those, uh, the software that you've built personally. I'm intrigued, though, how that means you view the current crop of VCs and how they view design first. How is that for you when you look at the scene?

A Yeah, so I'm, so I think one of the trends, I do think that more and more VCs value design. We are seeing that, and I think that's great. You're seeing more designers join VC firms as design partners. And I think we're seeing more interest from designers. There's a lot more designers being angel investors, and I think we'll see more designers wanting to be actual investment partners. So someone, you know, like Scott Belsky or like Jeff Veen. So we're seeing that that happen. At the same time, I think there is still a vast majority of investors who view design as this thing that you kind of add on after the fact, or that is, you know, kind of a visual layer that is not necessarily available. A necessity in building a company, and we want to get to the place where, you know, great design, great engineering, and great tech are table stakes in terms of building a great startup going forward, and so that's the world that we want to see, and that we want VCs to move forward into, and so a big part of what we do is try to be huge evangelists for design, and whenever we meet with other investors, whenever we meet with founders, kind of continuously champion The value of design and kind of show its, its effectiveness in building great companies.

AI assessment note: “I do think that more and more VCs value design. We are seeing that”

Q I am really intrigued. As a newly minted VC myself, I'm intrigued to hear your experiences on the, on the onboarding process in the entrance as to, as to how you found the experience going from designer to investor, and what were the potentially surprising elements first, and then the challenging elements for you?

A The way that we minimize the surprises around this is we actually modeled our activities for a couple years before we raised our fund. And so we, you know, both Enrique, Enrique had worked in venture for a few years, Right. And then for me, we were doing angel investing and modeling the behavior of the things that we wanted to do for a couple years. So it wasn't like we just said when woke up one day and just said, oh, we'll just, you know, raise a fund for two years. We, we kind of were in the ecosystem and said, if you had a great design partner as an investor, would that be interesting to you? And we, we, we went to founders. We, with this, we went to big VCs and said, Hey, if you had a co-investor, In your companies that could help your companies build great products and help you hire great designers. Would that be interesting? And all of these are like, this would be amazing to have a, you know, a collaborative investor that could do this alongside us for larger companies. They all, you know, as they scale design, it gets harder and harder. So they would love to have investors that could help with this. Very few investors focus on this. It's, it's a very specific skillset and knowledge and community that most investors aren't tied into. And so We already knew that a lot of the needs were there. We already knew, you know, we already built the relationship. So we actually, i…

AI assessment note: “in terms of surprises, we, I think, did a good job of minimizing those.”

Q What do you believe that most around you do not?

A I was thinking about this, and actually, when I, when I considered what's something I believe that others don't, I'm Jewish, and have recently engaged more with the local Jewish community here in San Francisco, and one of the things that I think not many folks in tech, there are not many Religious folks in the tech community. They tend to be agnostic or atheists. And being Jewish, you know, it's a great way of creating, like, ritual and connecting with heritage for me. And I actually think religion can be a great way to do that. And I think it's a big reason why you see a lot of people now kind of flocking to things like Burning Man and other spiritual forms. Like, once you remove religion, all of a sudden you're like, oh, well, wait a second. Where do I get? It did serve a purpose for many folks so that when you removed it, it's like, well, I need to find that somewhere else. So I think one of the things I believe is that, is that religion can still, when done right, play a really great role in enriching your life for many folks.

AI assessment note: “religion can still, when done right, play a really great role in enriching your life”

Q Absolutely. Can I ask, is it challenging to sustain your levels of support on the design front with the ever increasing portfolio?

A It's not because one of the great things that we've done is build programs that scale. And so Bridge allows us to scale our support in a way that offers deep, deep help to our companies over time in a really sustainable fashion. We've also built another program called Designer Founder Guild, which is a program where we bring great designer founders in our portfolio, but also ones outside of our portfolio together on a regular basis. And they exchange best practices and knowledge in terms of, we, we knew that the portfolio would scale and that we'd have to scale with it, so we already put in programs in place that could scale with the portfolio. Now, I think in two, three years, you know, we're gonna need to continue to expand and put in place those kind of structures, but we're always thinking, you know, that far ahead, and I think the other great thing is, for us, we are a, you know, we talk about being a depth over breadth Kind of early stage investor, and so we only do about 10, 10 to 12 investments a year, and so we're not trying to, you know, do 40, 50 investments a year. For us, you know, every founder we back, for us, is really, like, we're thinking, like, do we want to be with this person for the next 10 years? Do we believe this product should exist? Do we want to go to bat for this person and make sure that, and when a designer says, okay, well, which of your portfoli…

AI assessment note: “It's not because one of the great things that we've done is build programs”

Q a, is it quite that binary as good or bad? And is it not a matter of subjective belief in, in what makes one good and what makes one bad? You know, the Chinese have very different, uh, preferences towards UI than Western cultures where we're much more clean and generous. How do you view that kind of subjectiveness with design? Are products good or bad? Is it that binary?

A I think definitely there's, there's a gradation, right? Everything is like, uh, there's a gradation. And I think also there are so many different layers of Consideration when you think about is a product achieving its goal? So great products, they probably have different goals, right? There's business goals. There are goals for the end consumer. There are goals for society, right? Ideally, all those things are aligning beautifully where if a business does well, and if the product does well, then people get what they want out of the product. And actually we, the output is a better society. But Not many companies have all those things aligned. I'll get like a great example from the designer fund portfolio. We have a company called Omada Health, which is a diabetes prevention platform, and what they've done is they've built a product that mimics landmark research that shows that there was a program that if you, for 16 weeks, join with a cohort of other individuals, with a coach, and go through that program, then basically they can get you off the path To diabetes. And so, they put that program online, and they've actually seen better efficacy for that than the brick-and-mortar program. For companies that pay their own healthcare, paying for employees who are at risk of diabetes to go through the program can be a huge financial win for those companies. And if the product does well,…

AI assessment note: “I think definitely there's, there's a gradation, right?”

Q I am really intrigued. As a newly minted VC myself, I'm intrigued to hear your experiences on the, on the onboarding process in the entrance as to, as to how you found the experience going from designer to investor, and what were the potentially surprising elements first, and then the challenging elements for you?

A The way that we minimize the surprises around this is we actually modeled our activities for a couple years before we raised our fund. And so we, you know, both Enrique, Enrique had worked in venture for a few years, Right. And then for me, we were doing angel investing and modeling the behavior of the things that we wanted to do for a couple years. So it wasn't like we just said when woke up one day and just said, oh, we'll just, you know, raise a fund for two years. We, we kind of were in the ecosystem and said, if you had a great design partner as an investor, would that be interesting to you? And we, we, we went to founders. We, with this, we went to big VCs and said, Hey, if you had a co-investor, In your companies that could help your companies build great products and help you hire great designers. Would that be interesting? And all of these are like, this would be amazing to have a, you know, a collaborative investor that could do this alongside us for larger companies. They all, you know, as they scale design, it gets harder and harder. So they would love to have investors that could help with this. Very few investors focus on this. It's, it's a very specific skillset and knowledge and community that most investors aren't tied into. And so We already knew that a lot of the needs were there. We already knew, you know, we already built the relationship. So we actually, i…

AI assessment note: “in terms of surprises, we, I think, did a good job of minimizing those.”