Brandon Jacoby - Seeing Taste vs. Creating Taste as a designer

00:00:00I think the tastemakers know when tobreak the rules and when to push beyondthe boundaries of what exists today andwhen to quiet and to go with the flow.And I think that is actually the likecore ability that AI doesn't allow forright now is like knowing that balance.It's like knowing when to go super deepinto many different prompts to reallylike kind of shape and build somethingnew versus, you know, it's okay to notfight every battle and to say like[music] not everything needs to be newand like that process of zooming in andout, I think is is what creates taste.Welcome to Dive Club. My name is Rid andthis is where designers never stoplearning. Today's episode is withBrandon Jacoby who's had some seriouslyhigh-profile design roles at early CashApp as the first hire at Capital andmost recently at X. But the focus ofthis conversation is going to be aboutwhat Brandon is doing next [music]because he's starting an all newindependent practice to help founderspush past good enough. He shares somereally interesting thoughts on taste,what it takes to be creative with AI,and how to thrive in a zero-to-oneenvironment. But before we get into allof that, I had to know what it was likedesigning at X. It broke my brain alittle

00:01:15bituh when I first joined and you know, Iknew it was going to be crazy. I knew itwas going to be a grind and that waspart of the excitement that went into megoing there. Umbut it really blew like any expectationthat I had out of the water, especiallyaround just questioning everything. Alot of people talk about Elon'smethodology and way of working andquestioning every requirement andthinking from first principles and whileyou like see that and read about it andtry to emulate it if you're a fan ofthat way of working, like it truly justyou can't wrap your head around it untilyou've seen it firsthand. And I rememberin one of my first ever design reviewswith him,we're reviewing a bunch of differentthings from all different people acrossthe org, across the business. There wassomething that has been reported on, Ithink, you know, week over week forprobably months long before I got to thecompany. A new idea came up and becauseof this like long historical,you know, journey that this thing hasbeen on, this metric was being tracked.There was just like a question of or oran opinion, I should say, of well, wecan't we can't change it because, youknow, it's there's this this historywith it. And you know, you you become socomfortable with looking at the samemetrics, with looking at the sameproducts, and iterating it and trying toimprove it week over week.

00:02:30And someonequestioned like why why are we eventracking this metric? Like why not lookat this other thing that's going to tellthe same story but in a completelydifferent way and it might piss off alot of users if we change it, it mightchange the product completely if wechange it. But what if we did it? And Iremember the response like in any otherorganization I've been at, big company,small company, startup, you know,publicly traded, you know, large designorg, the response always would havebeen, well, let's get into it. And it'snot always, you know, people alwaysassume that it's going to be like no inbig companies, but it's not always no.Like the the hardest part about bigcompanies is not like that you can't getanything done, it's just that everythingtakes a long time to get done or ittakes a long time before you find out ifit can get done. And at X, Twitter,it was justinstant. Everything happened on a whim.Yeses, no's,there's no committees, there was justdecisions. And as crazy as anddisruptiveas it is to like mypreexisting ways ofreality, it's really cool. I thinkthat's something that again, like you Iwould never be able to learn in atextbook or as much as I could readabout Elon, like seeing someone justruthlessly discern and ruthlessly payforward on something, whether it's

00:03:45in a positive or a negative way, likeyou just have to question everyrequirement andif someone says anything that would getin the way of questioning a requirement,why is that a requirement in and ofitself? And it's just there's nobarriers, there's no walls. And thattook a little bit of getting used to,especially like designing something. Ithink the design is made up of so manymicro decisions.And I found myself designing interfaces,like deep in the weeds design work,questioningmyself at every second saying, well,actually like why am I not deciding justto do this crazy thing that I wouldn'tnormally think about? And designers Ithink have such acalloused way of working in those microdecisions where constraints are justlike these passive things floatingaround in the back of your mind. Andbeing able to like turn that off waslike a really big hill to climb to beable to to turn that off and just likedesign without thinking for the firsttime in my career. It's actually one ofthe keywords that I've been payingattention to recently is decisiveness.And even just thinking about some of thesuccessful traits in different orgsmoving forward, again, a world where wecan get more ideas and create more realestate for these micro decisions toexist, decisiveness actually is areally, really big deal for this yearand beyond.

00:05:01It's interesting to hearlike the extent of which that wasalready happening. Real quick messageand then we can jump back into it. Allright, Framer just released two killerAI features that I have to tell youabout. The first is wire framer. You canchat with AI to skip the blank canvasand spark all kinds of ideas. Andthere's no easier way to spin up aresponsive page with structure andstarter content that's ready to edit.Now, the second feature is workshop.It's a way to create advanced componentsusing natural language. So, you can spinup all types of new visual effects, nocoding required. It's just anotherreason why I recommend Framer toabsolutely everyone. [music]And you can start using these featurestoday. Just head to dive.club/framer.

00:05:47So, Jitter just released image to videoand it's a pretty big deal. All you haveto do is upload an asset and Jitter willinstantly generate a short video clip[music] from it with the help of AI.It's an easy way to add motion and depthto static backgrounds, maybe createlittle clips for brand visuals, or justin general [music] make any scene feelmore alive with subtle movement. It'ssuper fun to play with and availabletoday. Just head [music] todive.club/jitterto try it out. Now, on to the episode.Before we move on from Twitter, there'sone other tweet that I literally havebeen wanting to ask you about formonths. Nikita hadfreshly joined as head of product and Ithink you quote tweeted it or replied orsomething and you said that like in hisfirst week he had already taken you toonboarding school. Put us into that roomfor a second. What did you learn andwhat was that like?>> Yeah, it's funny cuz it actually reallyconnects to what we were talking aboutwith discernment. For kind of somehistorical context, I led design for thegrowth team at Cash App for a good chunkof my my early career. Onboarding was abig part of that, you know, it was a bigcompany. There were at the most like 45million people using product when when Iwas there. We were making microoptimizations, you know, we did bigexperiments and and big changes thatthat would, you

00:07:02know, hopefully move theneedle in big ways, but we were also,you know, doing small AB tests andfiguring things out. And I've beenaround onboarding flows for a long time,which is like the most nerdy thing I'veever said as a designer. But I actuallycan't stand designing onboarding flows,just as a side note. But, [laughter] youknow, have been around them and havedesigned a lot of uh onboarding flowsfor other startups and products,consumer, B2B. All that to say, I feltlike I knew onboarding a little bit. Iwas on a trip, it's actually in Hawaiiwith my family, and Nikita had justjoined andlike ran into the hotel room for a quickmeeting because we were working ononboarding for X. And we had spent along time going back and forth ondifferent designs. There were somedifferent directions that were beingproposed from different people acrossthe company. And, you know, with aproduct at X's scale, onboarding issomething that you don't want to break,you know, it'sso precious. You don't want to likebreak the most important flow tothe internet. And Nikita and I hopped ona call and he just like pulled up thisdoc that was like the inside of Nikita'sbrain that people know and and love fromthe outside, but seeing the inside ofit, it was like a I don't know, justlike a treasure chest and like Pandora'sBox of justlike the onboarding oracle came down andlike opened the veil and it was just,yeah, the craziest thing

00:08:17ever. But itwas wild because it was all things thatI'm like, oh, okay, that completelymakes sense and I wasn't thinking aboutit and no one else is thinking about it,but like Nikita is good at what he doesfor a reason and I left the companyshortly after that, not connected tothat, but just, you know, as far astiming goes, a lot of the onboardingstuff that he was looking at is whatended up getting implemented and itseems to be I know it's tricky subjectsometimes going into the weeds of X, butnow that you are working on differentproducts again, I'm curious if thatsession has shaped the way that youthink about onboarding for otherproducts. Like is there some maybe evennugget that you could impart to peoplelistening today that you carried withyou from that session? The biggesttakeaway in my whole career for likegrowth-related things>> like onboarding and and kind of morelike utilitarian flows in product arethere are patterns that work that showup in 90% of the products out there.Those patterns are there for a reasonand like a lot of designers, and I'mguilty of this myself, reinvent thewheel. And while reinventing the wheelis actually a really good thing and I wecan talk more about this, but I think alot of like the issue our industry facesright now is like people trying to stickto the pattern a little bit too much andkind of like revert to the mean a littlebit too much. There are such largegrowth teams

00:09:33and product teams that arehyper-focused on optimizing theironboarding flows that there is so muchinformation out there to pull from forsomething like that, especially foryoung designers, that it's like knowwhen to reinvent the wheel, know when tofollow patterns. And I think that thatskill of knowing when to do either ofthose is like the number one trait thatany, especially junior designer, canhave right now that I think will letthem go very far. Let's move ahead intothis next chapter here because you yousomewhat recently left X and kind ofventured out on to your own. So, talk tome a little bit about what that journeyhas been like. Cuz I know you're now atthe point where like, yeah, this is thething that I want to do. This is whatthis next part of my career is going tolook like. So, Yeah. what about themonths after X do you think highlights,you know, what you bring to the table asa designer and what you kind of wantedto double down on moving forward withyour career? I spent a little bit oftime immediately after I left reallyunsure what I wanted to do. Coming outof the burnoutof X mixed with the uncertainty of whatI wanted to do next, it was like aprettydifficult challenge. And I startedhelping some friends startups andstarted incubating some projects on theside.

00:10:48Very ex- but very exploratory and verykind of open-ended, independent, and,you know,things with a lot of flexibility. And Idid that as a form of exploration. Igave myself 3 monthsto to do that before kind of reallyramping up any actual decisions.And what I found what I was surprised bywas that exploratoryphase of life was actually the mostfulfilling thing that I had been doingin my career foryears prior. Being able to wake up everyday and explore different types ofroles, different, you know, acrossdesign and product design and branddesign and creative direction andproduct stuff that was outside of designentirely. Like being able to just thinkabout all of those different things,even though it was for the purpose ofexploring what I wanted to do next in mycareer, was actually fulfilling in andof itself. What was interesting is likethat was at a time where like the modelskind of hit this I think like thresholdwhereit really started to feel like anyonecould build anything whenever they want.And the tools being able to get to apoint where I suddenly feltre-inspired to just like sit down andhack on an idea that I had was reallypowerful. And all of that together waskind of a catalyst for

00:12:03this next chapterof leaning into the independent solopractice essentially and sayingexploring is a good thing, havingautonomy is a good thing, and like AItoolsI think more than ever allow people tobe autonomous because it can fill thegaps of what they feel like they can'tdo and it allows them to move quickerand more efficiently, but at the sametime focus onwhat I was good at. So, it's like, youknow, I was exploring and coding andI've historically been a prettynon-technical person. Um, just enough tolike piss off engineers that I've workedwith in my career in the past. But, forthe first time like I could actuallyfeel like I could build something andtake it as far as I could go, but not atthe risk of no longer being in Figma. Ilove Figma. I use it every day and Ithink like tinkering and draggingrectangles around is like actually stillthe best form of expression of exploringlike, you know, UI design for me. But,being able to like build and explore anduse AI to like supplement what I feellike I'm really good at was the coolestthing ever. And that was I think onlydiscovering that was only possible bygoing to that chapter of not knowing anduncertainty. I was about to say youprobably had the perfect overlap betweenyour own

00:13:19period of discovery and then all ofthese models just exploding. Like in thewhole spectrum of tech history, like itwas actually kind of flawless. Yeah, andbecause the models have gotten to wherethey're at, there's so much debatearound people saying that they'redeleting Figma and they're only buildingthings and designing things in cloudcode and or some people are the extremeother end of the spectrum and, you know,like to stand on the hill and yell howthe models aren't good at design and,you know, human taste and the humantouch is going to be there forever issuper important. And it's kind of like,I don't know, the way I look at that isit doesn't really matter. Like greatdesign has always been great designagnostic of the tools. And like sure thetools that are popular at any give onegiven time are help guide and shapeespecially like aesthetics that are kindof in trend at any given moment. But,design has always been aboutdecisiveness and judgment. And in aworld where suddenly a lot more peopleare equipped to design and to build,there's still the art of design and thescience of design that allow people tosay I'm just going to use whatever toolthat I want and the results are going tobe what I get. And I think that'sactually like another benefit of kind ofbeing in this independent path is like Ihave

00:14:34an agent that helps me with likelogistics and some client management andmy email and I wake up every day and Iget a little recap of stuff thathappened on a project overnight and Iget help from, you know, Figma make andsome of the other like AI tools to helpwhen I have a creative block. And thenI'm building things in cloud code andit's like I'm using the tools, but Ifeel like my like job hasn't reallychanged. I'm just like being a greatdesigner that's helping mold the worldand shape products into something that'sreally valuable for for customers andpeople that interact with thoseproducts. I kind of want to duck all theway down this rabbit hole now that we'restaring down it. So, Let's let's jumpin. During this period of explorationand tinkering,what did you learn about how you wantedto utilize these different AI tools inactual client work? Especially fromsomebody who sees a lot of value inbeing able to sling things around on acanvas,how do you think about when to reach forwhat tool for what purpose? The singlebiggest way that AI specifically hashelped with client work is actually theability to like build my own designtools.And I think you've you've like had otherguests on that or seen like kind of asimilar note. And I think that like thatis becoming a trend

00:15:49that I see with likethe best designers that I know is likebeing able to finally not only havedesign tools that exist including AItools, but using that AI to be able tobuild our own tools for whateverspecific purpose we have is like themost creatively empowering feeling thatI think I've ever had in my career.There was this old quote by JohnLasseter that I absolutely love and longbefore AI like I would come back to itall the time. And John Lasseter said itwith regards tothe creation of Toy Story.And he said the technology inspired theart, the art challenged the technology.I think we're at this pivotal momentwhere the limit of technologyto create the tooling that we need tolike create the things that we see inour head that we think are that aregreat, that limit's gone. And that againhas just been the most like freeingfeeling as a creative. I'm smiling fortwo reasons. One because I just am acomplete Pixar nerd. Especially OG Pixarlike John Lasseter high regard in mybook. But then also, even down to thelast like 24 hours that quote has beenso representative of my own experiencewhere I'm like working on this websiteand I kind of have this idea

00:17:04and Iliterally have no idea how to make it. Idon't even know if it's possible. But,I'm kind of like, is this possible? Andthen, you know, Claude's like, yeah,actually I think it kind of is. Andyou're like, okay, cool. Can we justlike try it? And you just hit enter andthen you're just like, okay, what'sgoing to happen? What's going to happen?And it's like sure enough I made thisreally cool likeparticle effect where it assembles intoicons for these feature cards. And stillI have no clue what the tech is. I haveno idea how it works. But, it was likekind of what was in my brain and it'sbeautiful. And I just keep having thosemoments where I'm like, oh my gosh, I Ican do almost anything, you know. Peopleare leveraging AI enough to like get toa certain point and then they're like,oh, I wish I like knew how to use AI todo XYZ thing in this tool that I'mbuilding. Like I wish I knew how to likeuse AI to build this like WebGL 3Drender. And it's just like I don't knowhow to like I don't even know whatquestions to ask. Ask Claude.>> [laughter]>> And like I find myself doing that myselfwhere I'm like, oh, like I wish I could,you know, I got to a certain point. I'mlike, I wish I could figure out how tolike get an agent to like do somethingor other I'm forgetting.And I remember sitting back in my chairand being like, oh, I should just askClaude like how to do this. And Ifigured it out. And actually like Claudedid a lot of it and I don't

00:18:19really knowwhat I would work, but it did. And it'slike I it's kind of tie it back to likethe experience at X of just likequestioning reality. Like I feel likeAI's like kind of challenged a lot ofpeople's reality where it's like you'reno longer bound by anything. All right,one more question before we move on fromAI. And then I do want to zoom out andtalk a little bit about your practiceand how you're thinking aboutpositioning yourself. But,you know, we talk a lot about AI as anamplifier.And what I've been thinking aboutrecently is thatyou know, not everybody has the samelevel of amplification. There is aspectrum. There are people that areabsolutely, you know, turning intorocket ships with AI. And then there arepeople who, you know, maybe getsomething out of it, but their theirceiling is a little bit capped. And so,I'm curious if you have a take on, youknow, what are some of the dominantvariables that dictate where a designeris on that spectrum? Who gets the mostamplified with AI today? It's funnybecause we were talking about how AI haslike allowed us to like become unboundand like it's removed barriers in a lotof ways that would typically be there ina design process. I've worked with a lotof people that have like shown me whatthat looks like long before AI. I thinkback to the early Cash App design days.They were,

00:19:35you know, Cash App is in high regardfrom a design perspective for a reasonbecause the team there, especially theearly team, is so talented. And a lot ofthat had to do with people just movingforward and like blazing trails and likerunning through walls.And if I like look at the golden threadbetween like every like great personthat I've had the pleasure of workingwith. They all share this like commontrait of running through walls, nottaking no for an answer, not from like abeing, you know, not from like acharacter standpoint, but just the Elonthing that I mentioned before of likequestioning everything, questioning whysomething's a requirement. If they getstuck on something, figuring out asolution, going in long before AI ifthey couldn't build it themselves,working with an engineer to build asolution to something that was inventinga new technology that would unlock somenew design path. That thing has alwaysexisted. AI has made it way easier, waybetter, and I think that the people thathave had a tendency to to do that beforeare like, you know, on this upward slopeof now having even more autonomy andlike there's less things that they needto partner with or like people that theyneed to partner with to like go runthrough those walls, but the people thatwere like scared to run through thosewalls, they would externalize blockers,that would get stuck. I I don't know ifAI's suddenly going to

00:20:50to empower themto to go do that. You still have to kindof,you know, take the initiative to to go,you know, take not take no for ananswer. The other thing I would say onit is, especially from like a visualdesign perspective, visual designrequires creativity, requires taste,requires feeling and empathy to be ableto sit back and say, "How how is someonegoing to feel when they look at this?"And it's like if it's a bunch of text ona page and there's weird alignment andlike really basic principles that arebroken, it's easy to say that someone'snot going to feel at peace when they'reusing this product. And that doesn'tmean that going and throwing a soft,neutral color palette with earth tonesis suddenly going to make them feelpeaceful. It's like there are so manydesign visual design fundamentals thatlike change how someone feels when theyinteract with the product. Thoseprinciples are still so true and, youknow, vibe code products or like peoplethat are just jumping to AI to kind offill their the gaps in the visual designand yeah, I think like the theactive visual design of like knowing howto get someone to feel a certain waythroughthe products that you create.>> let's dig into how you're leveragingthis, but maybe first to even zoom outfor a second to kind of set the stage.

00:22:06So, you're at the point now where you'regoing all in on this independentpractice. And I guess, you know, giventhe insanity of today's market, like howdo you think about even positioning anew solo practice? What types of clientsdo you want to work with? What are yourhopes for what this could even become?Taste is having a moment and people likeGreg Brockman are talking about howtaste is the new core skill or a newcore skill. People that are at thepinnacle of of like our industry in techare finally, I think a lot of designerswould say, coming around to what they'vebeen beating the drum on, which isdesign is important and taste isimportant. But so much of design havebecome homogeneous where designers aredesigning for other designers and tryingtoput into words or pictures or designs oflike what this like taste thing is. AndI think a lot of people could like pointat like a interface designed by Appleor, you know, insert great designcompany here and say, "Oh, that's acompany with taste because it's minimaland it has a left-aligned bold font withlike clean typography below that." Butlike taste is so much more about thejourney of design, much more than theresult. And on the like spectrum of likeyou're born with it and it's an

00:23:21innateability and you have it or you don't tolike it's something that can be learned,I like fall probably closer to the firstone, but I think it can be informed andshaped. I don't think it's likeimpossible to learn taste, but I thinkit's something that you have to foster.It's a muscle. Some people aregenetically gifted and born that to bean athlete and but they still have to goto the gym and train and work very hardto to be great at, you know, any sportor to to be strong in in a gymenvironment. Taste is the same way. Youknow, maybe some people are born with alittle bit more of a natural ability toto be a tastemaker and not just seetaste, but to create taste, but youstill have to foster it. And I thinkenvironment has to do with that so much.It's hard to just look at something andand copy it, but taste is so much deeperthan than just something visually thatyou have to let it sit with, you know,your your innermost being. One thingthat Dive Club has made abundantly clearto me over the last year is that thepractice of design is changing. And theold process of getting feedback justdoesn't quite cut it in today's world.>> [music]>> And that's why I'm excited to announcethat Inflight is officially in openbeta. It's the feedback tool that I'vealways wanted and

00:24:36it's built for a worldthat moves at the speed of AI. So, I canshare my prototypes, give context invideo walkthroughs, and Inflight makesit easy to get the exact feedback that Ineed to move forward, whether it'svoting on directions or maybe evengetting the green light to ship a newidea. And all of this is available in asingle link that [music] I can drop intoSlack or maybe even share with powerusers to test out a new prototype. I useInflight every day and it's totally[music] transformed the way that I sharework. So, I'm excited for you to try theproduct and if you ever want to jamabout it, just email me at [music]rid@inflight.co.Can we dig into this differentiationbetween seeing taste and creating taste?Like what does it require to be able tomake that jump as a designer? I thinkseeing taste is the thing that everyonehas. It's like you know it when you seeit, you know it when you feel it. Maybeyou don't. Maybe there's like somethreshold that you need to get to beforeyou, you know, you can tell when you'reusing something that'sbeautifully and thoughtfully crafted.But there's another level of like beingable to recognize, I think what I saidbefore even, like when to followexisting patterns versus when to blazenew trails, knowing what makes sense tofollow within the status quo

00:25:51and when topush the boundaries. Cuz it's not a hardand fast rule where, you know,tastemakers break all the rules andreinvent the wheel. I think thetastemakers know when to break the rulesand when topush beyond the boundaries of whatexists todayand when to quiet and to go with theflow. And I think that is actually thelike core ability that AI doesn't allowfor right now is like knowing thatbalance. It's like you can, you know,that's still the the part of AI toolsthat require human input. It's likeknowing when to go super deep into manydifferent prompts to really like kind ofshape and build something new versus,you know, it's okay to not fight everybattle and to say like not everythingneeds to be needs to be new. And likethat process of zooming in and out, Ithink is is what creates taste. I likethat distinction because we're enteringthis world or maybe we're already eventhere where if you see something that isgood, you can kind of replicate it. Youknow, like AI is pretty good atreplicating things. And so, all the timeI'll see a design where I'm like, "Thatis good." But maybe I know that it isgood because I have a full Notiondatabase of things that look like itthat I have decided are good. But thenevery once in a while you see somethingwhere you're like, "That is good andI've never seen anything like it." Andit takes a level of creativity

00:27:07to arriveat that. I don't even know if that'snecessarily a spike of mine. I'm more ofthe remixer, you know, I'm I'm taste bycuration and then subtle tweaks. Butthen I see something like for somereason the app Tonal comes to mind rightnow. I remember the first time I wentthrough that onboarding and used thatapp and I was like, "This isunbelievable."And it exists so far outside of the boxthat I draw from as a designer. And Idon't know, I think a lot about how toget there, but it's not an easy muscleto grow. Human creativity is so muchbigger than just design. When we talkabout taste, it's easy to like jump intolike tasteful product design or tastefulbrand design. Taste exists so farbeyond like the work that we do. Likeit's very rare that you meet someonewho's like an expert at their craft whodoesn't live that same craft outside ofthe work that they produce. And I thinklike, I don't know, work is just like anextension of of who you are as a person.You know, I'm excited [clears throat] inthis next chapter of my career. I'vealways been a really curious person andan exploratory person and I'm excited tofinally have a a solo practice, anindependent way of working where I canwork on a bunch of different things andwork

00:28:22with really great people andthat might be one group of peopleone week or one month and then the nextmonth that it's an entirely differentway of thinking, a different set ofpeople, and a different problem set. AndI think like that's like a big part ofwhat makesuhfor a great career step is like findingsomething that's very true to to who youare. All right, so talk to me a littlebit about your plans to effectivelybuild a a business model around sellingtaste. I know that's a little bit of acrude way to put it, but at the end ofthe day that is kind of what it is,right? Like most people who have anidea, who have some kind of a product,they don't have this ability that thatseparates truly great designers. And so,how do you even think aboutgoing to market with something like thator how it impacts the type of servicesyou want to offer or the way that youwork with clients? Like let's just getinto the weeds on how you want thispractice to operate. There's anotherpodcast I was listening to and I'mforgetting who said this, so I apologizeif that person happens to hear this cuzI'm going to totally paraphrase it andprobably butcher it.But they were saying, you know, if thecost of materials and labor for realestate went to zero overnight, assumingregulation is okay with growing a lot ofhousing. Like if if that were to happen,suddenly housing would explode and thereare, you know,

00:29:37there are infinite moreplaces to to reside. People would stillchoosewhere to live. There would still be achoice that people have to make in wherethey want [clears throat] to live, wherethey want to be, how it's going to makethem feel when they live there versussomewhere else. And I think software isis no different. Like software is thisform of hospitality where you're you'rewelcoming a user base into a product.And with AI and where the industry isgoing, like that thing of like cost ofmaterials and labor rapidly decreasing,and that is happening, but I think thesame is going to be true where it's likein a world whereanyone can create anything whenever theywant and everyone's empowered to justbuild something that solves a need theyhave, how are we going to choose what tobuild?How are consumersof that product going to be able tochoose to build it themselves versus usesomething else that's already created?How are these models going to know whatto build for that specific thing? Itstill requires human input. Humansaren't just like slaves to thetechnology that we create, maybe yet,but like, you know, we're we're notthere yet. And so in a world where it'slike super easy to build like goodenough, the thing that I'm like sellingis how to be great, and that's not

00:30:53tosay that I'm some, you know, oracle thatthat that can make, you know, I don'thave a Midas touch. I wish that weretrue. I wish I could touch anything andmake great, but I think I have like agood amount of experience that I've likebeen able to lean on working for bigcompanies and small companies acrossproducts and product design and branddesign and working under people likeElon but also Jack Dorsey and some otherlike great startup leadersto be able to say in a world where it'sreally easy to build like good enough,like how do we how do we build somethingthat's great? When you reflect on yourjourney working at, you know, some ofthese prolific companies, being early Imean, I remember when Party Round first,which I guess that was Capital. LikeParty Round design was so sick. Likewhen you first rolled that out, I waslike, "Oh my gosh, who is behind this?"Turns out it is you. So, when youreflect on this set of experiences indifferent roles that you've been in, I'mcurious if there are any moments thatreally rise to the top in terms of howthat set of experiences has shaped whoyou are as a designer, who you want tobe in working with these new companiesthrough the solo practice. Like whatwere some of the more formative timesthat really grew you as a designer? Ifeel like I've had like a really weird,interesting, diverse career. It's likebeen mixed with like some big companies

00:32:08and startups and some venture things inbetween and companies that are morechaotic like X and companies that aremoremellow, call it. That mix has shaped whoI am as a designer more than any onemoment that I can point to within any ofthose experiences. Like there are peoplefor sure that have impacted me on alevel that I can't even describe thatI'm super thankful to work with. Manypeople from Cash App, many people fromParty Round and Capital, many peoplefrom X, many people from, you know,things in between. A mentor of minewho's he's thehead of business, he's an executive, Iforget his exact title, but OwenJennings at Block, taught me so much ofwhat I know outside of design, and wepartnered super closely for for the fouryears that I was at Cash App.AndI think it's easy as a designer to lookfor mentors and designers that we lookup to, but there's so much to be learnedas a designer that's outside of ourcraft that is actually going to be thething that like propels your careerforward so much more than getting adesign crit with someone who's at acompany that you look up to that hold inhigh regard. So I think like people likeOwen, people

00:33:23like Jordi who is CEO at atParty Round, host of of TBPN now,another great podcast. People like himwho, you know, you're in the trenchestogether building stuff, and I learned alot that, you know, he let me do what Iwas great at, and I learned a lot fromwhat he was great at.>> even just building a solo practicestretches you in similar ways where allof a sudden your set of deliverables andthe things you have to think aboutaren't confined to whatever productyou're working on, but it's actuallylike how do how do I even make thishappen as a business, you know? Yes andno. The nice part about it is like itlike I said before, it feels like I canjust like be fully myself. There's waymore that you have to put upwithin a big companythat's like outside of design andoutside of like what I enjoy doing thanI'm finding the solo practice. I'm like,"Sure, there's like practical stuff oflike high management and projectmanagement, context switching betweendifferent things at once, and like taxesand accounting." But like I'd muchrather have like that be the likeannoying side stuff and then go reallydeep on just like working on things thatI'm passionate about thatfire me up with great people that arehopefully going to like change the worldversus likedealing with the things that you get atnot

00:34:38just big companies, but, you know,any structured organization in afull-time capacity. Are there anyspecific projects and clients, likeanything that you can talk about thatyou think highlights the way that youlike to insert yourself into thesecompanies? I've been working withAngelList. I was approached by them andtheir leadership team to build a apretty net new product project that theywere working on and and thinking aboutfor I think a pretty long time that, youknow, now is kind of finally the righttime to build it. And it was a projectthat was at the center of kind of myexperience between Cash App and PartyRound and even a little bit of X, and itwas like the most fun project to work onbecause I feel like I got to like pullfrom all these different experiences andlike it was the sum of all of myexperience that I could just like pourmy heart and soul and design and craftinto because it allowed me to just likefully be myself as a designer. I got topull from all those different threads.And that's what I'm saying like thedream for me, right? Like in the solopractice is is something that I can feellike that I can like stand on what I'vedone so far in my career, but also likescratch the curiosity itch at the sametime and like apply what I know and bearound a bunch of people that are somuch smarter

00:35:53than me and like push me tolearn new things that challenge me, butat the same time, you know,aren't just a replication of the samething over and over again. When wechatted earlier, you talked about thisidea of craft meets consequence. Can youunpack what you mean by that? Craftmeets consequence to me is like a ideawhere it challengeswhere a lot of our industry has gone todesigning for other designers. There aremany portfolios out there thatlook fantastic that I think in like asea of a of portfolios that hiringmanagers would be looking at, they theystand out and they catch the attentionof designers for XYZ reason. And as adesign industry, we're really good atthat. We're really good at likeunderstanding our users and like whatusers could be understood more thanourselves. So we're really good atunderstanding other designers andproducing work, meaning like aportfolio, that looks great to them. Andon the other end of the spectrum, youhave like teams and roles and peoplewithin an organization that sometimescome into conflict with what a lot ofnewer designers in their career want todo, which is some novel thing and theywant to spend a bunch of time on it,which I mean AI isbeautiful because it's kind of allowedsome of those things to actually happenmore naturally.

00:37:08But like historically,like there's always this toil betweenlike a PM and a designer to say, "Well,you need to ship by this date, but weneed to, you know, but as a designer, Ireally want to like ship this novel newarea." And the PM or the CEO is saying,"Well, we need to, you know, movemetrics and it doesn't make sense towork on this thing that's going todistract from this real, you know,consequential thing to build." And it'slike this thing it's been this back andforth. For me, like I've always vieweddesign as like my craft for building abusiness and building products, productsthat sell and and make people's livesbetter. Craft meets consequence is thisidea that like those two things canexist at the same time. They're notmutually exclusive. You can takesomething that is consequential and andshapes the world and and changespeople's lives, hopefully for like abusiness perspective, if it's like acommercial opportunity, like somethingthat makes a lot of money as well. Butat the same time is like having reallydeep and thoughtful craft and intention.I wish like more people would wouldunderstand that like those two thingscan can live in harmony, and like that'swhere the best products are are created.Like they're they follow each other,right? Like form follows function, butat the same time like craft followsconsequence, consequence follows craft.

00:38:23They like the more they live in harmonytogether, like the I think the thebigger, the better, the the greatestanything can become. A lot of the thingsthat you're saying about the role ofunderstanding like actually like thebusiness and what what moves the righttypes of needles in like productstrategy, but also this level ofcreativity that is very, very difficultto achieve given a lot of constraints.Like I'm kind of bundling a lot of thisin my brain into this correlationbetween the stage at which you aredesigning to. Cuz if you're going tojoin like a late stage giant company,like it's really hard to to make thistype of impact or design this type ofway or to come in and be like, "I havethis totally creative idea for thevisual identity." You know, it's likethat people are just going to kind oflaugh you out of the room a bit. Do yousee that type of correlation? Like doyou gravitate more early stage as aresult? I find myself gravitatingtowards new things. And sometimes thescale of that new thing looks like acompany, and world building with just meand a founder in a room where we'redesigning the company, not just theproduct of the company, but what is thecompany? What is the org design? What isthe brand identity? Andon a deeper level than the logo

00:39:38of likewhat what is this thing? And, you know,the founder says, I have this idea, butlike I what is a company? That's where Ilike plugging in. And then of coursetaking that and building the derivativesof that with what is the core MVP? Whatare like the five hero screens of theproduct? What are what is like the coreuser flow that someone's going to beinteracting with? What is the brandidentity? What is that like MVP brandlook like? So, it's like the the newthing in that sense is like the companyand like the the zero-to-one, you know,world build. But, there are bigcompanies as well that are doing newthings. And, you know, AngelList was agood example. I I also did a stint withCoinbase late last year where there's areally big new thing that was happening,but it was a really small team that wasthinking about this new thing and I gotto embed with that group and help shapeand inform what this new thing was goingto be. And yeah, whether it's like a bigcompany like like Coinbase or AngelListor a small startup that's just gettingstarted and hasn't even raised a roundof funding yet, it's still the sameconcept which is building something newandcrafting it. I think like one of themost beautiful parts about being adesigner is like the moment that ithappens that feels like magic whereyou're staring at a blank canvas and youlike shut your eyes and you're like whatshould be on this canvas? And then inthe best

00:40:54case scenario like it happens.And then other people see that canvasand other people interact with it. Andagain, whether it's at a big company ora small company, that is like a magicalmoment that got me wanting to design inthe first place and now I get toreplicate it over and over and overagain with with a bunch of differentgreat teams and great people with withreally cool ideas at a bunch ofdifferent places. And yeah, it feelslike a feels like magic. I live for thatmoment where you kind of get to hitcommand N and just start from scratch.And it's probably my favorite part aboutbeing a designer. So, maybe we could goa little bit deeper there for a secondand speak to somebody who perhaps hasn'tbeen in that situation. Either they'reearlier in their career or maybe they'vebeen you know, working at big companiesfor the last 10 years. And yeah, they'reinterested especially given the state ofthe market of joining something smallerwhere you are designing the company andnot just designing the interfaces thatexist within this product. And you know,you've been in that role so many times.Not only with clients, but in in youknow, some of thesebig time roles. I guess I'm curious tohear you talk a little bit about what itlooks like to thrive as a designer inthat environment. And if there are anyspecific things that designers who dowant to grow these muscles can do tobecome someone who excels

00:42:09in thiszero-to-one early stage role. The numberone thing that I would say to thatperson is find someone who you enjoyworking with.Whether it's a super early company andit's like a CEO or founderthat's hiring you. It's just going to beyou and them or there's a small teamthat's forming around a startup. Findinga a team that you enjoy working withbecause the earlier that you go in likea company's age that you're going to beworking with, like the more important itis to like jive well with the teamoutside of design of course. Like ifyou're the only designer, like thepeople you're going to be collaboratingwith are leadership, CEO, founder, headof engineering, CTO, maybe somemarketing people.Maybe not. Maybe it's just, you know,yeah, like you and a and a couple otherpeople. And finding great thoughtpartners that will bring the best workout of you is like the most importantthing, especially for someone who hasn'tbeen in that environment. And I thinkbeing able to to trust yourself in beinga designer in that room is is like the[snorts] other skill I think toto really push yourself on is like theability to have confidence in ideas andconfidence in your own inspiration.

00:43:24Andif you feel like that inspiration comesfrom looking at other great products andcopying them, it's like an okay place tostart. I'm like the the hardest placesor the hardest part in a a kind of ablank canvas design process is is whereto start and how it I mean especiallywith AI, but even outside of like thespecific tools, it's progress is thebest possible thing from going from zeroto one. And it's like you can sit thereand try to like close your eyes andthink of it in your headand then wait for, you know, somethingto happen, but like it's never going tohappen unless you just do something.Earlier in my career, I think I was likereally afraid of beingwrong.And I was really afraid to just trysomething. Not even for shippingsomething and being wrong and likelearning the hard way that no one wantsto use the product that you'redesigning, but like even just formyself. Like I'm staring at this blankcanvas. I don't know what to create. Imust be I must not be cut out forthis. I've grown in my career enough andreflected upon my own work enough to saythat like I know with 100% certaintythat even though I can get to a productthat looks like it could be pretty goodat this point, I know that I will designsomething the first time that looks likeabsolute garbage.And the first version of everything thatI create

00:44:40is so bad. I now again amconfident that I can like get it to agood spot and likeit's going to be great. That's the barthat I hold myself to, but starting isnot where you finish and doesn't have tobe where you finish. And like justcreating something that's terrible toget a idea on the paper is what likestarts the snowball rolling down thehill. And it's like you're you're nevergoing to figure out how to like find thebest solution and find that like momentthat it clicks for you to be like, "Ohyeah, this is this is gold." withouttrying something first. Especially justbecause like we were saying, you can beworking so closely with a founder whoprobably has a decent idea of the bigpicture vision. But especially ifthey're not a designer, like the thedetails and what they could actuallylook like in practice sometimes isn'tall the way flushed out. And so I evenfind that having as many quote unquotebad ideas or wrong ideas as possible isa good way for the them to help themnavigate their own mind, too. They cansee something and be like, "Oh, I didn'trealize that I thought this, but I'mlooking at this and this is wrong."quote unquote for you know, XYZ reasons.And now you're you're almost helpingthem think. Like the more artifacts youcan produce actually accelerates thefounders thinking in a way that I thinkmakes a good partner as well.

00:45:55Well, Ithink it's like the benefit of hiring adesigner instead of just like saying wedon't need a designer. We're just goingto vibe code something ourselves.Because as great as these models are atlike generating products and if you likeprovide them with the right human input,like they can produce like pretty goodwork. But that [clears throat] likejourney of exploration, the in-betweenmoments that you get when you're movingthings around on a Figma canvas, likethat's where like the real discoveryhappens. Like you can prompt somethingback and forth and like vibe codesomething and, you know, spend anotherhour prompting it to to get to like apretty refined thought. But I feel likeyou like miss out on those moments ofwhen you're just like tinkering. And tokind of connect this all to the tastething, like I think that taste makingcomes from like tinkering anddiscovering something new. And like whenyou're in between the promptsessentially, being able to like discoverand I you know, it's not just A or B,but it's some weird C thing that youdidn't think of originally that like youstumbled upon as like a happy accident.That's where the magic happens and likethat's where I feel like I've been ableto like produce my best work. And that'sthe thing that I feel like you get whenhiring a designerversus just saying that, you know, wedon't need them and then we'll do itourselves.

00:47:11And you almost always have tocross over the this is probably goodenough line in order to get to the someweird C thing that you discover. 100%and like, you know, the the sad part ofthis is like for most people like goodenough will be okay. That's not a badthing. There is a lot of good enough inthe world and like many people just needgood enough. But there's always like theones that push it just a little further.You sometimes have to like break rulesto do that. Sometimes you have to runthrough walls, but for those that aren'tcomfortable with with staying in thegood enough, I think that there's like areally fun thing to experience on theother side of that. Even going back toyour architecture analogy from earlier.It's like well, good enough is theprefab house or the copy and pasteapartment complex that you would seeover and over and over. It's the modernfarmhouse, you know, that I I it's allover in Michigan. They're everywhere,you know? It's like yeah, I've seen that90 times in the last few weeks. And yetthere are whole successful businessesthat have been built around the qualityof the interior, whether it's a hotel orrestaurant. And maybe now you're just inthe position where you kind of almosthave to sell that to companies anyway.Yeah, and and there's like a weirdelement to it where it's like, well, doproducts that are like greatautomatically mean they're like luxuryproducts? Like using your hotel example,like a

00:48:26lot of the like high taste hotelscompared to the things that are copy andpasted everywhere, maybe they're for aspecific set of people that are notaccessible to everyone. And like Iactually I don't think that's true. LikeI actually think if you look at Apple,Apple is likethe ultimate example of taste and andhigh quality products. And whether youlike argue about liquid glass or or not,like it's still a great example of likegreat thoughtful design, especially onlike the hardware front. Two-thirds ofthe world I think have an iPhone. Andlike you can't deny that the big part oftaste is actually figuring out how tolike deliverhigh levels of craft in an accessibleway so that as many people as possiblecan experience it. If you the copy andpaste farmhouse new development examplefor real estate, it's like you have tolike design something that is so goodthat people want it and make itaffordable enough that when people dohave the choice if they if they if it isaffordable enough to make the choice,like how do they choose something thatis great versus just the, you know, themodern farmhouse. Yeah, I I think that'sa good call. Like great is not only onan axis ofcost and luxury. Great could even comefromruthless simplification beyond anythingthat you would get out the box with themodels. And that also requires aphenomenal designer to come

00:49:41in and ownit. So many of the great products thathave been created in my lifetime werethings that were typically inaccessibleor reserved for for high net worthindividual to to experience and likebring it to the masses. And like that isan act of like taste and craft in and ofitself of being able to do that. Like Ithink of Uber as an example. Like Uberis probably like one of the singlebiggest like inventionsthat uses a software invention.Obviously the real world is a big partof it. The world of like transportationwas flipped on its head when anyonecould stand on any street cornerbasically in any city in like mostcountries in the world and press abutton and a car shows up next to themwithin like 10 minutes. Like that'ssomething that just most people couldnever experience until Uber and and Lyftand it was created. That's taste. Likethat's craft to be able to like say thatlike that's something that people need.We've covered a lot of ground. Before Ilet you go, I'm going to give you anopportunity to kind of close your eyesand imagine what the future could looklike for you. So when you think aboutthe potential outcomes for yourself, youknow, Travis is able to imagine Uber,you know, what are you imagining kind ofthing?What do you think this independentpractice

00:50:56could become? Yeah, I think theworld is shifting to be especially withthe design industry is shifting to bemore and more filled with independentpeople.I I feel like Icould namefive people who are like the greatestdesigners that I know in the industryright now and like it just so happensthat they're all independent. There aremany great designers that are stillfull-time and it's nothing against that.But I think in a world wherea lot more people are independent, whereAI and tooling has evolved to like pushpeople even further than they could gobefore. I think that the future for melooks like a call a lot likecollaboration with great people.And not just collaborating with othergreat designers, but collaborating withfounders and leaders of of products andpeople that are that want to startsomething new and collaborating to bringmore taste to fight the slop. But if Ikind of fast forward a few years downthe road, I don't think any of us couldpredict what the world is going to looklike with how fast things are moving andthe rate of change that's happening. Butthe thing that I hope for is that in aworld of a lot more software and like ina world of like abundance and choicethat there is something with, you know,my signature on it that can, you know,stand out that, you know, in a world of

00:52:11a slop and abundance that there's stillsomething great. I can't think of abetter way to end it than fight theslop. So I'm going to hang it up there.Brandon, this has been amazing. Thanksfor coming on and sharing a little bitabout your journey and just everythingthat you're thinking about andexploring. It's been [music]really, really fun. So appreciate you.Thank you so much for having me andyeah, it was was an awesome chat.>> [music]