Season 4

|

Episode 4

How to bring your ideas to life

Tommy Geoco

Owner of UX Tools

Jan 11, 2024

Jan 11, 2024

|

51 mins

51 mins

music by Dennis

About this Episode

In this episode we get to learn from Tommy Geoco who has launched countless projects, sold a startup, and built an audience of almost a million designers online. This conversation has everything—here’s a little taste of what you can expect:

  • The wild story behind Tommy selling his first company

  • Why design tools matter more than ever

  • How to become better at selling yourself

  • Tons of strategies for your next side project

  • Tommy’s mental model for learning as a self-taught designer

  • Why Tommy doesn’t care about being novel

  • Ways to improve your “taste” as a designer

  • Why Tommy acquired UX Tools (and his plans for it)

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Lauren LoPrete

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Design Lead @ Gusto

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Deep Dives

Get our weekly breakdowns

Insights + resources from top designers 👇

Lauren LoPrete

Director of Design Systems @ Cash App

David Hoang

VP of Marketing and Design @ Replit

Adrien Griveau

Founding Designer @ Linear

James McDonald

Designer @ Clerk

Femke

Design Lead @ Gusto

Join 10K+ designers

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Transcript chapters

Tommy's journey into design

Tommy: I think it was like 2010 and I was on my way out of the military, but I recognize that, , my spouse at the time and a lot of the other Marine Corps spouses on base were really keen on yard sailing together and they wouldn't really go out of the base. It was a very local thing. So I was like, Oh, that would be an interesting like website to create.

And I didn't know how to code. I didn't even know what a designer was. And so I went and bought a script. Pinterest had just dropped not long ago and it was in its like very rudimentary form.

But they had that beautiful kind of masonry grid scrolling feature that just blew everybody away. And I bought this script that replicated that feature. And it was basically a Pinterest clone. And I was like, well, that won't do, but , the entire feature of it was cool. I was like, I'll let people post their items and then I'll just go in and I'll try to make it look different.

So I don't get sued by Pinterest was kind of my concern. And so my nights and weekends were spent going in between training and running and all the, the headache of the Marine Corps and then trying to figure out how to change the interface just enough. So this thing looked different. And then I just started telling people about it around base and it just caught like wildfire and then I got this wise idea. I was like, okay, this is clearly taking off. I had like higher ups asking me about it.

And I said, I'm going to take it all down. I'm going to completely redesign it and come out like a real brand. And that decision ended up killing the whole hype that it had because I never got to the redesign fast enough I didn't know how to code as much as I was trying to cram learning php And then the whole thing just fell apart and it turned into this like facebook page that actually still worked for people But it was it was such a heartbreaking and very big lesson learned for me that sometimes you just have to make fast, scrappy decisions and it's not going to look how you ideally want it to look.

, but if you don't have the runway to survive to get to that point, it's never going to look the way you want it to look.

Ridd: I love to learn by doing, just throw yourself at it. Like, I'm just going to download a script and ship this thing. I definitely think that that's kind of been like a little bit of a theme in your journey for sure, is just, trying things and putting yourself out there. So maybe even like continue along with the story a little bit.

And can you take us to that moment? I think it's a roughly around like nine, 10 years ago. And you decide that you're going to leave your job and this idea of comfort and start something. What was that like?

Tommy's journey into design

Tommy: I think it was like 2010 and I was on my way out of the military, but I recognize that, , my spouse at the time and a lot of the other Marine Corps spouses on base were really keen on yard sailing together and they wouldn't really go out of the base. It was a very local thing. So I was like, Oh, that would be an interesting like website to create.

And I didn't know how to code. I didn't even know what a designer was. And so I went and bought a script. Pinterest had just dropped not long ago and it was in its like very rudimentary form.

But they had that beautiful kind of masonry grid scrolling feature that just blew everybody away. And I bought this script that replicated that feature. And it was basically a Pinterest clone. And I was like, well, that won't do, but , the entire feature of it was cool. I was like, I'll let people post their items and then I'll just go in and I'll try to make it look different.

So I don't get sued by Pinterest was kind of my concern. And so my nights and weekends were spent going in between training and running and all the, the headache of the Marine Corps and then trying to figure out how to change the interface just enough. So this thing looked different. And then I just started telling people about it around base and it just caught like wildfire and then I got this wise idea. I was like, okay, this is clearly taking off. I had like higher ups asking me about it.

And I said, I'm going to take it all down. I'm going to completely redesign it and come out like a real brand. And that decision ended up killing the whole hype that it had because I never got to the redesign fast enough I didn't know how to code as much as I was trying to cram learning php And then the whole thing just fell apart and it turned into this like facebook page that actually still worked for people But it was it was such a heartbreaking and very big lesson learned for me that sometimes you just have to make fast, scrappy decisions and it's not going to look how you ideally want it to look.

, but if you don't have the runway to survive to get to that point, it's never going to look the way you want it to look.

Ridd: I love to learn by doing, just throw yourself at it. Like, I'm just going to download a script and ship this thing. I definitely think that that's kind of been like a little bit of a theme in your journey for sure, is just, trying things and putting yourself out there. So maybe even like continue along with the story a little bit.

And can you take us to that moment? I think it's a roughly around like nine, 10 years ago. And you decide that you're going to leave your job and this idea of comfort and start something. What was that like?

Tommy's live-streaming startup

Tommy: What that taught me was that I really liked trying to solve problems with technology. And I got a taste of what it looked like when you built something and people started using it. And I got immediately addicted to that.

And I was like, how do I do that? And so I would spend like. A handful of years working agency, but always trying to build my own thing. It was like lead generation for local pool businesses, you know, little WordPress websites. , it was e sports betting platform, but then eventually while I'm working at an agency, I met one of my co founders and he's an incredible technical guy. And in the e sports kind of genre, Justin TV had become a really big place where people who were playing video games in e sports, , communities were kind of flocking to it was the place to watch this stuff because no one else was giving it the time of day.

And what we realized is Justin TV was turning into Twitch. There were a lot of streamers who were willing to pay for custom development so they could have cool graphics on their screen. And we're like, Hey. Let's create this like self serve way to do that. So people could accept donations and do this whole thing.

And we ended up building a platform and there's a couple other people who recognize this opportunity too. So we're racing to do this thing and we get to market and it just, it blows up on us. It absolutely blows up. And the thing that was really terrifying to me. Was I've got four kids, a wife, and I have some client work I'm supposed to be working on that I could not bring myself to do because I'm just looking at this app and I've never seen this kind of growth. I recognize there's an opportunity here and we're not charging any money for it. And so we see 100,000 daily active users within three months. And we have no money. I was afraid to turn on the money faucet.

I didn't want to charge for donations. I didn't want to charge anything, but I'm going absolutely broke, and TwitchCon, the very first TwitchCon ever, , is happening that fall. And it's 10, 000 to go and get a booth at TwitchCon as a vendor.

We do not have 10,000. We scraped together just enough money to get like a small little billboard that stood up on its own. A little pop up that I designed for. Enough money to print out the design. We got these really crappy t shirts made that said our company name on it. StreamPro. And we got a really rough hotel in the tenderloin and we ate Walgreens sub sandwiches.

When we stayed out there, we didn't realize how hilly the place was in San Francisco. And so we didn't Uber anywhere and we just walked places and we'd be drenched in sweat because we're just climbing these incline hills when we were walking around and fortunately my BizDev founder, he had made some relationships.

One of the companies we made a relationship with just said, Hey, come and like, occupy this four foot space right next to us. And we're like, we'll do it. And when I land in San Francisco, my wife calls me and says, our vehicle engine just broke down. It's going to be a 3, 000 repair. And I literally landed.

We got to the hotel and I broke down crying. Because I, at that moment, I had realized I've probably been making a mistake, like I haven't been focusing on the financial things that were important to me. I'm in a situation now where I've left my family to pursue this wild dream and so my buddies said, Hey, like we're already here. Let's go ahead and do this three day event. Let's try to make the most of it. And we'll talk about what this looks like moving forward. Three weeks later, we got acquired. And it was because of that event in TwitchCon. And it was the wildest adventure for me.

I'll be honest with you. We sold way too early. We should have been a situation that said no, because I think that would have been the right answer at the time.

Tommy's live-streaming startup

Tommy: What that taught me was that I really liked trying to solve problems with technology. And I got a taste of what it looked like when you built something and people started using it. And I got immediately addicted to that.

And I was like, how do I do that? And so I would spend like. A handful of years working agency, but always trying to build my own thing. It was like lead generation for local pool businesses, you know, little WordPress websites. , it was e sports betting platform, but then eventually while I'm working at an agency, I met one of my co founders and he's an incredible technical guy. And in the e sports kind of genre, Justin TV had become a really big place where people who were playing video games in e sports, , communities were kind of flocking to it was the place to watch this stuff because no one else was giving it the time of day.

And what we realized is Justin TV was turning into Twitch. There were a lot of streamers who were willing to pay for custom development so they could have cool graphics on their screen. And we're like, Hey. Let's create this like self serve way to do that. So people could accept donations and do this whole thing.

And we ended up building a platform and there's a couple other people who recognize this opportunity too. So we're racing to do this thing and we get to market and it just, it blows up on us. It absolutely blows up. And the thing that was really terrifying to me. Was I've got four kids, a wife, and I have some client work I'm supposed to be working on that I could not bring myself to do because I'm just looking at this app and I've never seen this kind of growth. I recognize there's an opportunity here and we're not charging any money for it. And so we see 100,000 daily active users within three months. And we have no money. I was afraid to turn on the money faucet.

I didn't want to charge for donations. I didn't want to charge anything, but I'm going absolutely broke, and TwitchCon, the very first TwitchCon ever, , is happening that fall. And it's 10, 000 to go and get a booth at TwitchCon as a vendor.

We do not have 10,000. We scraped together just enough money to get like a small little billboard that stood up on its own. A little pop up that I designed for. Enough money to print out the design. We got these really crappy t shirts made that said our company name on it. StreamPro. And we got a really rough hotel in the tenderloin and we ate Walgreens sub sandwiches.

When we stayed out there, we didn't realize how hilly the place was in San Francisco. And so we didn't Uber anywhere and we just walked places and we'd be drenched in sweat because we're just climbing these incline hills when we were walking around and fortunately my BizDev founder, he had made some relationships.

One of the companies we made a relationship with just said, Hey, come and like, occupy this four foot space right next to us. And we're like, we'll do it. And when I land in San Francisco, my wife calls me and says, our vehicle engine just broke down. It's going to be a 3, 000 repair. And I literally landed.

We got to the hotel and I broke down crying. Because I, at that moment, I had realized I've probably been making a mistake, like I haven't been focusing on the financial things that were important to me. I'm in a situation now where I've left my family to pursue this wild dream and so my buddies said, Hey, like we're already here. Let's go ahead and do this three day event. Let's try to make the most of it. And we'll talk about what this looks like moving forward. Three weeks later, we got acquired. And it was because of that event in TwitchCon. And it was the wildest adventure for me.

I'll be honest with you. We sold way too early. We should have been a situation that said no, because I think that would have been the right answer at the time.

UX Tools and design education


Ridd: We recently announced one of the biggest swings that I've seen a designer take in a while with the acquisition of UX tools. co. Can you give us a little bit of that backstory and. Why you made that decision and kind of what your vision is with it moving forward.

Tommy: I'm really excited about UX tools and I'm also staying up at night, terrified about it this is the first time I've ever invested like the amount of money I've invested into this and the time, if this doesn't work, I'm going to have to, I'm gonna have to figure something out. It's going to be a scary time if this doesn't work, but this is really something I believe in because before I went into the military, I tried to go to school and it wasn't for me. I just, I can't, I can't consume a large. Curriculum. I like to be trying to build something and learning at the same time. And so many of the prerequisites and things just weren't doing it for me. I tried again after the military.

I was like, well, I'll do I'll work on some of this website development and I'll go to school at the same time. It just was not doing it. I wanted to be learning python right then and there. I didn't want to have to worry about everything that led up to my first computer science class. I didn't want to do that.

And I owe such a large part of my career to The ability for the internet to provide me online learning opportunities to go and find independent courses. If that did not exist, my life would look so much more different right now.

I didn't, I did not come up from this like upbringing where, you know, I had a single mom who was working all the time. I did not have this wonderful network. I had my first child when I was 19 years old. I was a military vet, not an officer. I was, you know, a low ranking grunt. , I had all these things that statistically this probably doesn't look this way if online education did not exist for me. And I look at that, and I realize that there are two things I think missing from people who want to work in these more lucrative roles.

one, oh man, I wish we had more apprenticeships, like I really do. I think this is such a field, that would benefit so strongly. From having someone smacking your hand with the ruler while you're trying to work on a real problem at a company and teaching you as you're doing it.

That would be like the most ideal situation and it takes a lot, not just a company. It takes really, uh, an entire society's structural system to be different for that to be how we operate. So UX tools to me or online education in general.

Is kind of the next best iteration because we had boot camps come out and we've had a lot of people go to boot camps, and I do think boot camps were well meaning. I think the problem that started to happen with boot camps. There's a couple of things, but one of them is, you know, the curriculum gets dated very quickly.

This production line has changed. It's continuing to change, right? but Then on top of that, the barrier to entry. To people who can create content or create ideas now with social media, with how common it is to just own a really advanced piece of technology in your pocket, all of that has come together to make it easy for anybody to share ideas or to transfer knowledge online and with that lower barrier to entry has become a lot of different You know, variance in quality, so the question is, what do we do about that? And for me, the way I've always learned and not everyone learns like me, and I'm going to learn a lot about this, but the way I've always learned is to try a thing. Build that military yard sale app, try and get people to pay me for leads. And then when I get stuck, go and try to learn and find the information, wherever it exists about what I'm stuck on, learned the thing in some capacity.

And I'm not going to be a pro at it, but it'll at least give me like a hammer to hit the brick wall with get unstuck and then continue forward. And so that try get stuck, learn, get unstuck loop has been such a big part of how I've. You know, I guess become a designer really.

And that's what I want to do for people

UX Tools and design education


Ridd: We recently announced one of the biggest swings that I've seen a designer take in a while with the acquisition of UX tools. co. Can you give us a little bit of that backstory and. Why you made that decision and kind of what your vision is with it moving forward.

Tommy: I'm really excited about UX tools and I'm also staying up at night, terrified about it this is the first time I've ever invested like the amount of money I've invested into this and the time, if this doesn't work, I'm going to have to, I'm gonna have to figure something out. It's going to be a scary time if this doesn't work, but this is really something I believe in because before I went into the military, I tried to go to school and it wasn't for me. I just, I can't, I can't consume a large. Curriculum. I like to be trying to build something and learning at the same time. And so many of the prerequisites and things just weren't doing it for me. I tried again after the military.

I was like, well, I'll do I'll work on some of this website development and I'll go to school at the same time. It just was not doing it. I wanted to be learning python right then and there. I didn't want to have to worry about everything that led up to my first computer science class. I didn't want to do that.

And I owe such a large part of my career to The ability for the internet to provide me online learning opportunities to go and find independent courses. If that did not exist, my life would look so much more different right now.

I didn't, I did not come up from this like upbringing where, you know, I had a single mom who was working all the time. I did not have this wonderful network. I had my first child when I was 19 years old. I was a military vet, not an officer. I was, you know, a low ranking grunt. , I had all these things that statistically this probably doesn't look this way if online education did not exist for me. And I look at that, and I realize that there are two things I think missing from people who want to work in these more lucrative roles.

one, oh man, I wish we had more apprenticeships, like I really do. I think this is such a field, that would benefit so strongly. From having someone smacking your hand with the ruler while you're trying to work on a real problem at a company and teaching you as you're doing it.

That would be like the most ideal situation and it takes a lot, not just a company. It takes really, uh, an entire society's structural system to be different for that to be how we operate. So UX tools to me or online education in general.

Is kind of the next best iteration because we had boot camps come out and we've had a lot of people go to boot camps, and I do think boot camps were well meaning. I think the problem that started to happen with boot camps. There's a couple of things, but one of them is, you know, the curriculum gets dated very quickly.

This production line has changed. It's continuing to change, right? but Then on top of that, the barrier to entry. To people who can create content or create ideas now with social media, with how common it is to just own a really advanced piece of technology in your pocket, all of that has come together to make it easy for anybody to share ideas or to transfer knowledge online and with that lower barrier to entry has become a lot of different You know, variance in quality, so the question is, what do we do about that? And for me, the way I've always learned and not everyone learns like me, and I'm going to learn a lot about this, but the way I've always learned is to try a thing. Build that military yard sale app, try and get people to pay me for leads. And then when I get stuck, go and try to learn and find the information, wherever it exists about what I'm stuck on, learned the thing in some capacity.

And I'm not going to be a pro at it, but it'll at least give me like a hammer to hit the brick wall with get unstuck and then continue forward. And so that try get stuck, learn, get unstuck loop has been such a big part of how I've. You know, I guess become a designer really.

And that's what I want to do for people

Shipping = oxygen

Ridd: I love hearing you talk about that loop. Because something that's clear, listening to you talk is you have this bias toward action when a lot of people come to me and they're like, man, how do I get out of tutorial land? I keep learning and like duping myself by believing I'm making all this progress, but I'm really just consuming without actually creating and working towards something.

So having that like end goal and thing that you want to bring into the world as a reason to learn, you can almost default to. To ship and to build and to tinker and to explore and learn when you're stuck and not just like wake up and say, you know, I'm going to consume another tutorial today, man, I think that's such an excellent way and just like a higher level model to approach this idea of investing in yourself and learning on the go.

Tommy: The feedback loop with people who use or consume the stuff you create is almost like oxygen. That's how I view it. The longer you keep all of your ideas inside of that Figma file or just kind of inside of your head, , the, the quicker you're going to essentially lose the ability.

To make that a reality but the minute I had that feedback loop, the motivation, the hunger, the ability and willingness to, to push through the oncoming brick walls, and if you're ever going to create something and you have the ability to try and distribute that idea and it's that versus, well, let me just like refine this a few more iterations, go with the former because that oxygen is going to carry you so much further than, you know, feeling good about the third iteration of the thing.

Shipping = oxygen

Ridd: I love hearing you talk about that loop. Because something that's clear, listening to you talk is you have this bias toward action when a lot of people come to me and they're like, man, how do I get out of tutorial land? I keep learning and like duping myself by believing I'm making all this progress, but I'm really just consuming without actually creating and working towards something.

So having that like end goal and thing that you want to bring into the world as a reason to learn, you can almost default to. To ship and to build and to tinker and to explore and learn when you're stuck and not just like wake up and say, you know, I'm going to consume another tutorial today, man, I think that's such an excellent way and just like a higher level model to approach this idea of investing in yourself and learning on the go.

Tommy: The feedback loop with people who use or consume the stuff you create is almost like oxygen. That's how I view it. The longer you keep all of your ideas inside of that Figma file or just kind of inside of your head, , the, the quicker you're going to essentially lose the ability.

To make that a reality but the minute I had that feedback loop, the motivation, the hunger, the ability and willingness to, to push through the oncoming brick walls, and if you're ever going to create something and you have the ability to try and distribute that idea and it's that versus, well, let me just like refine this a few more iterations, go with the former because that oxygen is going to carry you so much further than, you know, feeling good about the third iteration of the thing.

How the role of designer is about to change

Ridd: You said something interesting about how easy it is for bootcamp curriculums to become out of date. And I think that's like increasing rapidly as even from my own perspective, like having invested so much into this curriculum and then all of a sudden Figma releases variables and it just totally blows everything to smithereens and you have to start over.

One of the things that you talked about in your launch announcement for the UX tools acquisition was basically making a bet that the way we design software is fundamentally going to change. Can you talk a little bit about what you mean by that? What you see coming and then how do you then approach building an education business on top of that reality?

Tommy: I think hard skills have kind of gotten a little bit of a bad reputation over the last five years, a lot of design leaders or certain design disciplines kind of say, Hey, design is more than the tooling.

And so for that reason, I think some people might be tricked into discounting the tools that exist. But the truth is those tools, I really think more than ever, we need to be paying attention to today. For example, I think we're going to see a lot more hybrid responsibilities, not because economically we're being, it's being demanded of us. Although I do think that's part of it, but also because it's just going to become more feasible in the past. It's not necessarily the most feasible thing for a product designer to be doing product management work all the time.

That's an exhausting ask. You're probably not being compensated for it. And so those things didn't always make sense. I think that that's going to continue to become less and less the case it's not a leap for you to go, Hey, I'm going to spend my Thursday on competitive analysis today those are the kinds of things that I think. think we're going to see more empowerment, so many designers are like, should I learn to code? Listen, that path has been there for a long time. And I do think there are things designers should know about the medium we're creating in the box model, image optimization, how load times are impacted based on API calls, like those things like know those things, if you're inclined to build, like if you want to live in code and debug and do things like that, go do that.

But if you don't really want to debug, like you like building, but you don't want to debug, because I'm telling you right now, debugging is what killed coding for me. If you don't, if you would rather just build and solve problems, , you're probably very well suited in that product management bucket, being able to really evaluate an industry.

And so I think those paths are really going to exist. Now, do we ditch altogether the PM engineer design model? I don't know, but I can tell you what typically seems to happen is the people we look up to in Silicon Valley, make a decision a couple of years later. The industry as a whole evaluates that decision, and then you see the domino effect kind of affects the rest of the regions in the world.

Right? And so people are going to look at Airbnb in two or three years, and then say, Was that a good decision? And the day someone in media proclaims yes, then you're going to see everybody start to do it, right? , and so we're going to see a lot of things like that, but I think it just makes sense. And you're not just going to see designers go into these other fields, you're going to see product managers.

And they're asking me already, like, I want to do more design work. I don't want to consider myself a designer, but like my company's asking me to do the design work. How do I learn the skills of a designer? And when you think about that, you think less about, I need to take a product design course. And you think more about, I need to learn how to do Figma to create a prototype.

You know what I mean? That, in my mind, is the kind of hard skills that I think I think we'll deserve and get the emphasis moving forward because you're going to just see a lot of design adjacent people wanting to learn design skills.

How the role of designer is about to change

Ridd: You said something interesting about how easy it is for bootcamp curriculums to become out of date. And I think that's like increasing rapidly as even from my own perspective, like having invested so much into this curriculum and then all of a sudden Figma releases variables and it just totally blows everything to smithereens and you have to start over.

One of the things that you talked about in your launch announcement for the UX tools acquisition was basically making a bet that the way we design software is fundamentally going to change. Can you talk a little bit about what you mean by that? What you see coming and then how do you then approach building an education business on top of that reality?

Tommy: I think hard skills have kind of gotten a little bit of a bad reputation over the last five years, a lot of design leaders or certain design disciplines kind of say, Hey, design is more than the tooling.

And so for that reason, I think some people might be tricked into discounting the tools that exist. But the truth is those tools, I really think more than ever, we need to be paying attention to today. For example, I think we're going to see a lot more hybrid responsibilities, not because economically we're being, it's being demanded of us. Although I do think that's part of it, but also because it's just going to become more feasible in the past. It's not necessarily the most feasible thing for a product designer to be doing product management work all the time.

That's an exhausting ask. You're probably not being compensated for it. And so those things didn't always make sense. I think that that's going to continue to become less and less the case it's not a leap for you to go, Hey, I'm going to spend my Thursday on competitive analysis today those are the kinds of things that I think. think we're going to see more empowerment, so many designers are like, should I learn to code? Listen, that path has been there for a long time. And I do think there are things designers should know about the medium we're creating in the box model, image optimization, how load times are impacted based on API calls, like those things like know those things, if you're inclined to build, like if you want to live in code and debug and do things like that, go do that.

But if you don't really want to debug, like you like building, but you don't want to debug, because I'm telling you right now, debugging is what killed coding for me. If you don't, if you would rather just build and solve problems, , you're probably very well suited in that product management bucket, being able to really evaluate an industry.

And so I think those paths are really going to exist. Now, do we ditch altogether the PM engineer design model? I don't know, but I can tell you what typically seems to happen is the people we look up to in Silicon Valley, make a decision a couple of years later. The industry as a whole evaluates that decision, and then you see the domino effect kind of affects the rest of the regions in the world.

Right? And so people are going to look at Airbnb in two or three years, and then say, Was that a good decision? And the day someone in media proclaims yes, then you're going to see everybody start to do it, right? , and so we're going to see a lot of things like that, but I think it just makes sense. And you're not just going to see designers go into these other fields, you're going to see product managers.

And they're asking me already, like, I want to do more design work. I don't want to consider myself a designer, but like my company's asking me to do the design work. How do I learn the skills of a designer? And when you think about that, you think less about, I need to take a product design course. And you think more about, I need to learn how to do Figma to create a prototype.

You know what I mean? That, in my mind, is the kind of hard skills that I think I think we'll deserve and get the emphasis moving forward because you're going to just see a lot of design adjacent people wanting to learn design skills.

Why design tools matter more than ever

Ridd: man. There's so much to unpack there. Like I love those points. We've all seen so many people write something along the lines of like, well, it's not the tools that matter.

It's the designer, you know? And it's like, yes, totally true. However, man, our tools have changed a lot. And the biggest way that they've changed is they're inherently collaborative. You can't say, Oh, I could do just as good of a job as a, as a UX designer on a napkin nowadays, because nobody else can play on that napkin with you.

And the more collaborative that our tools become, I think the harder it is to ignore them.

Why design tools matter more than ever

Ridd: man. There's so much to unpack there. Like I love those points. We've all seen so many people write something along the lines of like, well, it's not the tools that matter.

It's the designer, you know? And it's like, yes, totally true. However, man, our tools have changed a lot. And the biggest way that they've changed is they're inherently collaborative. You can't say, Oh, I could do just as good of a job as a, as a UX designer on a napkin nowadays, because nobody else can play on that napkin with you.

And the more collaborative that our tools become, I think the harder it is to ignore them.

Becoming "multi-class" as a designer

Ridd: So I've been thinking a lot about, well, how do designers respond to this flattening of the stack, trying to think of design as less of like a predefined role and more of a skill set that you bring to the table and What is like one other skillset that you can combine it with, like based off of your skills and interests, what is your intersection point of things that you bring to the table? And yeah, maybe it's product management.

Maybe it's, you can write a little bit of front end. But maybe it's like, actually, I really like UX writing and copywriting. And that's something that I don't have to be reliant on another person for. Or maybe I feel pretty comfortable making simple marketing videos and being a part of those go to market conversations.

Like that design plus X mental exercise, I think is a really interesting way to think about how to position yourself as a candidate today.

Tommy: When I came up into this field, I didn't say to myself, I want to be a designer. And today that's, that's like a thing.

That's an aspiration. People say, I want to be a designer. And they have this predefined definition and My kind of view of what that looks like. I will do these responsibilities. I will be in charge of this for me. It was that coding was really hard and I had ideas that I wanted to get to market, so design was kind of the most. feasible way to bring an idea, to life just enough in order for me to determine if I should invest into it. When you really do think about it that way, that like my role as a designer is not to make this.

Pixel perfect Figma prototype that does all this bells and whistles and like it basically functions as a standalone app in Figma Really my job is just to communicate the key parts for whatever the challenges that we're dealing with Whether that's I need to inform instruction to engineers or I need to help the growth team convey this message to potential customers when you really start to understand like as a designer my job is just to Better communicate the ideas that are already in the room.

Then you really start to have the conversation with yourself of is this thing I'm spending half my day on a value added activity. Or is this kind of playground work that maybe I should make some time for on my weekend? If you just kind of think about like, what does my team need right now? And what's kind of the threshold of, You know, the critical mass of all right, they've got it.

And now everything I'm continuing to work on is more for me. And I should like I should roll back on that just a little bit. Those have been the things I've been trying to communicate, and I'm still learning the best way to communicate that to people because there certainly is a gap between someone like me who became a designer because I was a bad coder and someone who was a bad coder.

grew up in an industry that had already existed and said, Hey, like that's the role that I someday see myself in.

Ridd: I'm another fellow designer who only became a designer because I was a bad coder. So that totally resonates with me. You know, man, there are so many different ways to invest in your skillset as a designer. And I think that's historically been the case. And then you can make the argument based off of even some of the things that we were just talking about, that it's only going to be more of the case where there are just a lot of different ways that you can make an impact and move the needle.

Becoming "multi-class" as a designer

Ridd: So I've been thinking a lot about, well, how do designers respond to this flattening of the stack, trying to think of design as less of like a predefined role and more of a skill set that you bring to the table and What is like one other skillset that you can combine it with, like based off of your skills and interests, what is your intersection point of things that you bring to the table? And yeah, maybe it's product management.

Maybe it's, you can write a little bit of front end. But maybe it's like, actually, I really like UX writing and copywriting. And that's something that I don't have to be reliant on another person for. Or maybe I feel pretty comfortable making simple marketing videos and being a part of those go to market conversations.

Like that design plus X mental exercise, I think is a really interesting way to think about how to position yourself as a candidate today.

Tommy: When I came up into this field, I didn't say to myself, I want to be a designer. And today that's, that's like a thing.

That's an aspiration. People say, I want to be a designer. And they have this predefined definition and My kind of view of what that looks like. I will do these responsibilities. I will be in charge of this for me. It was that coding was really hard and I had ideas that I wanted to get to market, so design was kind of the most. feasible way to bring an idea, to life just enough in order for me to determine if I should invest into it. When you really do think about it that way, that like my role as a designer is not to make this.

Pixel perfect Figma prototype that does all this bells and whistles and like it basically functions as a standalone app in Figma Really my job is just to communicate the key parts for whatever the challenges that we're dealing with Whether that's I need to inform instruction to engineers or I need to help the growth team convey this message to potential customers when you really start to understand like as a designer my job is just to Better communicate the ideas that are already in the room.

Then you really start to have the conversation with yourself of is this thing I'm spending half my day on a value added activity. Or is this kind of playground work that maybe I should make some time for on my weekend? If you just kind of think about like, what does my team need right now? And what's kind of the threshold of, You know, the critical mass of all right, they've got it.

And now everything I'm continuing to work on is more for me. And I should like I should roll back on that just a little bit. Those have been the things I've been trying to communicate, and I'm still learning the best way to communicate that to people because there certainly is a gap between someone like me who became a designer because I was a bad coder and someone who was a bad coder.

grew up in an industry that had already existed and said, Hey, like that's the role that I someday see myself in.

Ridd: I'm another fellow designer who only became a designer because I was a bad coder. So that totally resonates with me. You know, man, there are so many different ways to invest in your skillset as a designer. And I think that's historically been the case. And then you can make the argument based off of even some of the things that we were just talking about, that it's only going to be more of the case where there are just a lot of different ways that you can make an impact and move the needle.

How senior designers can invest in the future

Ridd: So I want to talk. A couple hypotheticals and maybe just even brainstorm potential learning pathways for people. And the first person is, let's say that they're a senior designer. They've been doing this for a few years, but they want to skate to where the puck is going. What are some of the. Tactical skill sets that you think people can invest in now to future proof themselves based off of where design is headed in the coming years.

Tommy: I say two things, which is one on the, on the mindset side, you got to get rid of the cynicism. Like when you see these new tools coming out and listen, we've been through the crypto hype. We've been through hype cycles. Now, many of us. And so it's easy to look at another hype cycle and get cynical about it.

I understand that. But we can't do that if we want to continue to, like you put it, skate to where the puck's going, cynicism is going to kill your ability to do that effectively. So you got to ditch the cynicism as best you can. And the best way to do that is to just go out there and spend time playing with new tools.

For example, you could go and just say, Hey, I'm going to go and invest into a coding for designers course. a bad thing. And some people might learn really well that way. But then there's another entry point to learning to be a coder as a designer, right? And that's maybe going and playing with some of the tools that have come out.

Like Framer is one that I really love. And not that that's going to allow you and teach you to create these like robust product experiences, but it is going to help you understand how you're. Figma design is going to translate to the screen medium, and that acts as a gateway to, okay, I see what the limitations in framer are. How can I actually extend this further? Oh, I've got to learn a little bit more about JavaScript. So like I'm going to go and look and again, go getting into that, try get stuck, learn, get unstuck loop. That's one way that I would say to somebody who's already been in this field who has probably.

Um, gotten comfortable in their seat and said, this is what the job's going to look like for the next 15 years. And now suddenly they're like, wait a second, things are changing. What am I supposed to do? Well, my answer to them is go and play with the tools, go and play with the tools. Meaningfully go and create something that doesn't necessarily have to make money.

Hey, if you're inclined and you want to build something that actually goes to market and makes money. That's fine. Just know that the kind of lessons you're going to learn are going to have a lot less to do with the hard skill learning and a lot more to do with how do I make money in the marketplace.

And there's, that's a whole other set of skill sets. Instead, spend a Saturday, spend a couple of Saturdays and just learn a new tool and then make the decision. I don't like this tool or I don't like this skill. This isn't for me, but don't make that decision beforehand. Make that decision after you've actually meaningfully built something with it or tried to use whatever that tool is to do something.

Ridd: I love that advice. Just tinkering the importance of tinkering, even a couple more tools that I'll list, like Rive is another one that to me just blows my mind what people are doing, where I'm like, man, if I was wanting to make myself unique as a candidate, being able to contribute Rive files and animations to actual products that are shipping feels like, well, that's, that's a superpower. Another one that I've been playing with is, , visual electric. com. I never really got into mid journey. I'm not like a huge discord person that was intimidating to me.

Holy smokes. What visual electric is doing right now for image generation is incredible. And all of a sudden it's like come to life for me where I'm like making all of my own illustrations and even using it to explore different textures that I can put onto websites that I'm designing. I love that advice.

Tinker, play, explore. I want to have another hypothetical and maybe this one's almost a little bit more challenging, which is.

How senior designers can invest in the future

Ridd: So I want to talk. A couple hypotheticals and maybe just even brainstorm potential learning pathways for people. And the first person is, let's say that they're a senior designer. They've been doing this for a few years, but they want to skate to where the puck is going. What are some of the. Tactical skill sets that you think people can invest in now to future proof themselves based off of where design is headed in the coming years.

Tommy: I say two things, which is one on the, on the mindset side, you got to get rid of the cynicism. Like when you see these new tools coming out and listen, we've been through the crypto hype. We've been through hype cycles. Now, many of us. And so it's easy to look at another hype cycle and get cynical about it.

I understand that. But we can't do that if we want to continue to, like you put it, skate to where the puck's going, cynicism is going to kill your ability to do that effectively. So you got to ditch the cynicism as best you can. And the best way to do that is to just go out there and spend time playing with new tools.

For example, you could go and just say, Hey, I'm going to go and invest into a coding for designers course. a bad thing. And some people might learn really well that way. But then there's another entry point to learning to be a coder as a designer, right? And that's maybe going and playing with some of the tools that have come out.

Like Framer is one that I really love. And not that that's going to allow you and teach you to create these like robust product experiences, but it is going to help you understand how you're. Figma design is going to translate to the screen medium, and that acts as a gateway to, okay, I see what the limitations in framer are. How can I actually extend this further? Oh, I've got to learn a little bit more about JavaScript. So like I'm going to go and look and again, go getting into that, try get stuck, learn, get unstuck loop. That's one way that I would say to somebody who's already been in this field who has probably.

Um, gotten comfortable in their seat and said, this is what the job's going to look like for the next 15 years. And now suddenly they're like, wait a second, things are changing. What am I supposed to do? Well, my answer to them is go and play with the tools, go and play with the tools. Meaningfully go and create something that doesn't necessarily have to make money.

Hey, if you're inclined and you want to build something that actually goes to market and makes money. That's fine. Just know that the kind of lessons you're going to learn are going to have a lot less to do with the hard skill learning and a lot more to do with how do I make money in the marketplace.

And there's, that's a whole other set of skill sets. Instead, spend a Saturday, spend a couple of Saturdays and just learn a new tool and then make the decision. I don't like this tool or I don't like this skill. This isn't for me, but don't make that decision beforehand. Make that decision after you've actually meaningfully built something with it or tried to use whatever that tool is to do something.

Ridd: I love that advice. Just tinkering the importance of tinkering, even a couple more tools that I'll list, like Rive is another one that to me just blows my mind what people are doing, where I'm like, man, if I was wanting to make myself unique as a candidate, being able to contribute Rive files and animations to actual products that are shipping feels like, well, that's, that's a superpower. Another one that I've been playing with is, , visual electric. com. I never really got into mid journey. I'm not like a huge discord person that was intimidating to me.

Holy smokes. What visual electric is doing right now for image generation is incredible. And all of a sudden it's like come to life for me where I'm like making all of my own illustrations and even using it to explore different textures that I can put onto websites that I'm designing. I love that advice.

Tinker, play, explore. I want to have another hypothetical and maybe this one's almost a little bit more challenging, which is.

Advice for junior designers

Ridd: Let's say someone's listening to this. Where they potentially have even recently transitioned into design. Maybe they have some kind of an internship, a little bit of experience under their belt, or maybe they just got laid off after their first role.

Unfortunately, a lot of people are in that situation. How do you think about. Where designers should invest from there and specifically like the sequencing of learning because there's so many different things to learn. You can so easily be overwhelmed by the landscape. What would you do if you were in that situation?

Tommy: It's hard and I feel for people who are on the, kind of first half of their career right now because it's tough, but what I would tell people is that now more than ever, it is important for you to learn how to sell yourself. And there's a number of ways you can do that.

That's in person. That's portfolio work. That's making decisions based on how those decisions are going to impact your ability to sell yourself. Here's what I mean. It's a bad word to say, do free work. Many of us who have been in this field for a long time have a privilege. Because , we can tell people don't do free work because I won't do free work and I can afford not to do free work.

But there are other people out there who need a portfolio and you're not going to get clients without real work in your portfolio. So you can fight the good fight with those of us saying don't do free work and you can support our cause and we'll make you a martyr. But that's not going to help solve your problem in selling yourself.

And so I'm not necessarily saying go and strive to do free work. What I'm saying is you need to make decisions that are right for you. And for some people doing less than optimal projects like I'm probably too good for that project because it doesn't, uh, inspire me or I, it doesn't pay me the amount that I think I'm worth a cut, whatever the criteria is right now, if you are early in your career and your portfolio does not help sell yourself, if you don't know how to sell yourself, if you don't know where to get leads, those are the types of activities that I would be focusing on.

That's the work that I personally wouldn't want to do. But it's probably the most valuable work. If you'd rather just sit and your answer to your problem is I'm just going to improve my visual design skill and someone will eventually recognize my visual design skills because I've invested a one month on it right now.

And that's going to solve my problem. This is what I'm talking about. There's value add activities, and then there's performance theater, and that's probably more performance theater. But if you don't even have that problem.

Where you have to prove your visual skill to somebody in an actual job setting, then that's not your problem right now, your problem is I need to get people to give me a chance, and you have to sell yourself, and that's uncomfortable. That's not the skillset that a lot of people promised you that you would have to learn, but it is the skillset you're gonna have to figure out, because it doesn't just end there learning how to sell yourself and learning how to sell your ideas, that's that's the job of design.

Like, that really is just our job, is building these ideas out and finding different ways to communicate them.

Advice for junior designers

Ridd: Let's say someone's listening to this. Where they potentially have even recently transitioned into design. Maybe they have some kind of an internship, a little bit of experience under their belt, or maybe they just got laid off after their first role.

Unfortunately, a lot of people are in that situation. How do you think about. Where designers should invest from there and specifically like the sequencing of learning because there's so many different things to learn. You can so easily be overwhelmed by the landscape. What would you do if you were in that situation?

Tommy: It's hard and I feel for people who are on the, kind of first half of their career right now because it's tough, but what I would tell people is that now more than ever, it is important for you to learn how to sell yourself. And there's a number of ways you can do that.

That's in person. That's portfolio work. That's making decisions based on how those decisions are going to impact your ability to sell yourself. Here's what I mean. It's a bad word to say, do free work. Many of us who have been in this field for a long time have a privilege. Because , we can tell people don't do free work because I won't do free work and I can afford not to do free work.

But there are other people out there who need a portfolio and you're not going to get clients without real work in your portfolio. So you can fight the good fight with those of us saying don't do free work and you can support our cause and we'll make you a martyr. But that's not going to help solve your problem in selling yourself.

And so I'm not necessarily saying go and strive to do free work. What I'm saying is you need to make decisions that are right for you. And for some people doing less than optimal projects like I'm probably too good for that project because it doesn't, uh, inspire me or I, it doesn't pay me the amount that I think I'm worth a cut, whatever the criteria is right now, if you are early in your career and your portfolio does not help sell yourself, if you don't know how to sell yourself, if you don't know where to get leads, those are the types of activities that I would be focusing on.

That's the work that I personally wouldn't want to do. But it's probably the most valuable work. If you'd rather just sit and your answer to your problem is I'm just going to improve my visual design skill and someone will eventually recognize my visual design skills because I've invested a one month on it right now.

And that's going to solve my problem. This is what I'm talking about. There's value add activities, and then there's performance theater, and that's probably more performance theater. But if you don't even have that problem.

Where you have to prove your visual skill to somebody in an actual job setting, then that's not your problem right now, your problem is I need to get people to give me a chance, and you have to sell yourself, and that's uncomfortable. That's not the skillset that a lot of people promised you that you would have to learn, but it is the skillset you're gonna have to figure out, because it doesn't just end there learning how to sell yourself and learning how to sell your ideas, that's that's the job of design.

Like, that really is just our job, is building these ideas out and finding different ways to communicate them.

How to approach your next side project

Ridd: I think a lot of people listening to this are inspired by how you're selling yourself and taking these big swings with UX tools and shipping and experimenting. And I'd love to learn a little bit more from you, how did you think about effectively allocating?

Your time outside of work to these different like passion projects or, uh, skill sets that you were hoping to learn, like what was exciting to you and how did you make that decision? And maybe you could even talk a little bit more broadly to about advice for designers who like have this itch , to make something, to ship something, but they don't yet have clarity for what that should be.

Tommy: today, right now as you're talking to me today, I feel like I'm in a really fortunate position. I've more or less learned how to hustle, so to speak, meaning I don't sacrifice, you know, my, my personal health. I don't sacrifice my relationships with my family, and I still find ways to work hard.

I've learned how to make those trade offs. It's not perfect, but it's pretty good, and I'm happy with it. That wasn't always the case. I literally would spend, Almost four years, and I'm not exaggerating when I say this, almost four years working 60 to 80 hour weeks wouldn't take any kind of holiday breaks, wasn't spending a lot of time with the family, and that would eventually turn into this reckoning.

My mental health reckoning. I had a very, very dark period of my life after I sold the company where it kind of all just came crashing down on me. And suddenly this hustle culture that I had subscribed to, , I really started to resent.

And I said, why did I do that? I don't know if that was worth it. Sure, it got me to Silicon Valley. Sure, I was able to sell a company. But like, I did not feel like a winner. And that was something I really had to come to terms with. And so what I would say to people today is make time for play, make time for your mental health, but don't, you know, the pendulum has swung a bit.

And even for me, I'm, I'm the extreme case where like I subscribed hardcore to hustle culture and like the consequences kicked my butt. So I don't, I don't preach hustle culture, go out there and hustle. You don't need your weekends. What I will say is, hard work is still necessary. Don't flinch against hard work.

The way that I pursue hard work, though, is, I might go into, like, monk mode for a week, or for a weekend, or maybe at a max two weeks. There's an initiative that really needs my attention, either at the job, or a project I'm working on. But then the following weekend or the next week, like I'm going to get that time back.

I'm blocking that off. And I'm telling people, Hey, like minimum effort this week, I'm chilling. I'm going to go hang out with the family. I'm going to focus on me. There's something I've always wanted to work on or, or, or make or unrelated to the job. I'm going to go do that. And I make that important. , we are essentially our priorities.

You know, whatever we make important, that's what we become. To answer your question there. At the beginning of my career was not intentional. All I knew was money, money, money. And that's what I had to pursue. Today. I'm just more intentional about it.

And what I would say to somebody who's kind of thinking about wanting to do a side project, don't feel like you need that thing to succeed right now today. And if you have. a day job. If you have something that's paying the bills, have fun with that. Yes, that means your Monday through Friday is probably taken up a bit, but like, have fun with the Saturday.

Make that thing. There are so many great tools out there. If you see a tool, you're like, Hey, maybe that will help me get to whatever the outcome of my project is. Go play with that. And even if you end up playing with that all Saturday and you're like, I got nothing done today. I didn't actually make progress on my project.

Appreciate the play that you got from that. And eventually you can get to the place where it's like, okay, I need to, if I want this project to actually turn money, then yes, you can start thinking about what are the right decisions to make, but enjoy the process of bringing something to life without somebody breathing down your neck,

Ridd: I think there are also people listening to this who like do have ideas. Maybe they have a little bit of momentum. They're making something. But perhaps they're a little bit intimidated by this lack of having an audience and maybe even the idea of putting themselves out there is a little bit intimidating.

And I think it's interesting to call out like 10 plus years into your career, you've made the jump to be full time creator working for yourself. So can you talk a little bit about why you made that decision and then any. Lessons or strategies that you've learned along the way that you think other designers listening could use to get momentum on their own journey.

Tommy: There was a period in software where if you built a thing and you just kind of got a little squeaky wheel noise out there, you'd attract customers. Well, now we're like, software's eaten the world. It's saturated.

If you build it, they will not come. And that goes not just for software, but anything you create. It used to be search engine optimization was kind of the distribution model. And Google really cracked down on that because everyone found ways to exploit it.

For me, my first few companies, Reddit was such a great distribution model. , people exploited that and then Reddit's cracked down on that. , and social media was like paid ads for a while, but it wasn't, people weren't like really taking this idea of building in public seriously until a little later.

And then people realized, Oh, if I like, just talk about what I'm building and show the nuts and bolts of it, that's interesting enough that it tracks people who want to continue following what I'm doing and maybe even turn into customers. And what I would say to people today is I get the cynicism around creator culture, but it's no longer just like lifestyle influencers and memes distribution exists at scale.

And I view what social media has become today. Warts and all is kind of an indie movement. It really is. It's a response to corporations that are willing to just fire their employees when economic pullback happens. It's a response to all of the middlemen who like to take their cut from book publishers and record labels.

It's a response to essentially everybody needing to make one bet in a company as a laborer, and then have that bet completely turned on its head. I think that social media creators today, people who use it, it's weird to just like box it into one definition as social media creator. All it is is the new small business.

It's a new distribution that didn't used to exist. And so you might have a bad idea that you spend a lot of time on. And you've got 5, 000 people on TikTok or Instagram who are willing to give it a try. And that idea sucks. Yeah, you might lose a little bit of goodwill and you're gonna have to lick your wounds and think of something else.

But that distribution channel didn't go away. You still have it. And that's what's super cool is that when you have a distribution channel, it can do so many things for you. It can allow you to build a business on top of it. It can have you test ideas before you need to sink a ton of money into it.

Because people are going to tell you if they think that idea is worthwhile. If you're somebody who wants to knowledge transfer, if you see a problem in the market or you see a problem with how design is happening from your bedroom, these four walls of mine. I can try to make that impact. And what I would tell people is if you're starting out, if that's interesting to you, I want to let you know, you know, I've got almost a million followers across different social channels now and all of my content, anytime I ever tried to package an idea.

Right? We say content, but just ideas like I've tried to package an idea. Sometimes my ideas just don't hit. The execution is bad. Maybe the idea is not a very good idea. It happens like there's building in public and then there's like thinking in public, which is a terrifying prospect because you are going to get criticized.

But sometimes people aren't going to criticize you because only 14 people saw it. And that happens a lot, even to me still today. And the truth is, is if you take a short term approach to anything, I'm gonna share my ideas on, you know, TikTok or LinkedIn. And you're like, oh my gosh, after 30 days, this has been a dud.

I'm going to stop doing this. Well, that's going to be a hard way to get better. You can't expect to get any form of mastery. And one of the things I tell people is, you know, your first design or your first, you know, video or your first written sub stack newsletter is not going to be that great.

It's probably going to suck. But your hundreds, your hundredth is going to be pretty good, but you're not going to get there unless you do the reps to get there and you have to do those repetitions. And that just goes with anything. It's like that 10, 000 hour rule. So if you're starting out today, pick one platform, don't try to be everywhere all at once.

Don't do that. Pick one thing that resonates. Do you like to do video? Do you like to create images? Do you like to write? Or are those things that may be like, I don't know if I like to, but I want to try. Okay. Pick one and spend 90 days doing it. Just spend 90 days and practice, think in public, get through the ones that are going to be tough because it's going to be tough try, get stuck, learn, get unstuck

Ridd: I love the idea of thinking in public and also even highlighting the fact that like, man, there's just not as much risk in the beginning of your process as you think there is. Like when I made the decision to think in public, I was like, what if my ideas suck? And I've looked back on some of them and turns out, yeah, some of them sucked.

They totally did, but nobody saw them in the grand scheme of things. Nobody saw them and they were completely meaningless. All they were, were just me getting reps and being more comfortable writing and putting myself out there and even just being a magnet for people who. Have thoughts on similar issues and wanting to even critique things and being able to learn from that and iterate and take that into the next time.

So I think that's just spot on. Like if you're on the fence and you're, you know, struggling to just hit enter, send tweet, post on LinkedIn, whatever it is, make a video,

Tommy: Yeah.

Ridd: man, in the early days, nobody cares about you. And that's actually a blessing.

Tommy: Every single piece of content I've ever made, it makes you kind of a better designer because you treat it like an MVP, treat it like something like there's an idea, there's an execution, I'm going to put it out and I'm going to learn from that.

I used to think my ideas about moving quickly in dysfunctional situations.

Applied to everybody, but it's not true. There are situations where that's just not the case, and it really helped me see that. Okay, there are situations where that's true, and it's true at scale, but that scale is not universal, and that really helped me redefine how I talk about it when I use absolutes and when I don't.

And that has been a really helpful thing just in my life in general, because, you know, at the age of 37 now, I feel like I've experienced a lot of stuff. I start to think, Oh, the chances of me being wrong this time are lower. Well, it's been a nice eye opener to see that that's still, I'm still sprightly. I get it wrong.

How to approach your next side project

Ridd: I think a lot of people listening to this are inspired by how you're selling yourself and taking these big swings with UX tools and shipping and experimenting. And I'd love to learn a little bit more from you, how did you think about effectively allocating?

Your time outside of work to these different like passion projects or, uh, skill sets that you were hoping to learn, like what was exciting to you and how did you make that decision? And maybe you could even talk a little bit more broadly to about advice for designers who like have this itch , to make something, to ship something, but they don't yet have clarity for what that should be.

Tommy: today, right now as you're talking to me today, I feel like I'm in a really fortunate position. I've more or less learned how to hustle, so to speak, meaning I don't sacrifice, you know, my, my personal health. I don't sacrifice my relationships with my family, and I still find ways to work hard.

I've learned how to make those trade offs. It's not perfect, but it's pretty good, and I'm happy with it. That wasn't always the case. I literally would spend, Almost four years, and I'm not exaggerating when I say this, almost four years working 60 to 80 hour weeks wouldn't take any kind of holiday breaks, wasn't spending a lot of time with the family, and that would eventually turn into this reckoning.

My mental health reckoning. I had a very, very dark period of my life after I sold the company where it kind of all just came crashing down on me. And suddenly this hustle culture that I had subscribed to, , I really started to resent.

And I said, why did I do that? I don't know if that was worth it. Sure, it got me to Silicon Valley. Sure, I was able to sell a company. But like, I did not feel like a winner. And that was something I really had to come to terms with. And so what I would say to people today is make time for play, make time for your mental health, but don't, you know, the pendulum has swung a bit.

And even for me, I'm, I'm the extreme case where like I subscribed hardcore to hustle culture and like the consequences kicked my butt. So I don't, I don't preach hustle culture, go out there and hustle. You don't need your weekends. What I will say is, hard work is still necessary. Don't flinch against hard work.

The way that I pursue hard work, though, is, I might go into, like, monk mode for a week, or for a weekend, or maybe at a max two weeks. There's an initiative that really needs my attention, either at the job, or a project I'm working on. But then the following weekend or the next week, like I'm going to get that time back.

I'm blocking that off. And I'm telling people, Hey, like minimum effort this week, I'm chilling. I'm going to go hang out with the family. I'm going to focus on me. There's something I've always wanted to work on or, or, or make or unrelated to the job. I'm going to go do that. And I make that important. , we are essentially our priorities.

You know, whatever we make important, that's what we become. To answer your question there. At the beginning of my career was not intentional. All I knew was money, money, money. And that's what I had to pursue. Today. I'm just more intentional about it.

And what I would say to somebody who's kind of thinking about wanting to do a side project, don't feel like you need that thing to succeed right now today. And if you have. a day job. If you have something that's paying the bills, have fun with that. Yes, that means your Monday through Friday is probably taken up a bit, but like, have fun with the Saturday.

Make that thing. There are so many great tools out there. If you see a tool, you're like, Hey, maybe that will help me get to whatever the outcome of my project is. Go play with that. And even if you end up playing with that all Saturday and you're like, I got nothing done today. I didn't actually make progress on my project.

Appreciate the play that you got from that. And eventually you can get to the place where it's like, okay, I need to, if I want this project to actually turn money, then yes, you can start thinking about what are the right decisions to make, but enjoy the process of bringing something to life without somebody breathing down your neck,

Ridd: I think there are also people listening to this who like do have ideas. Maybe they have a little bit of momentum. They're making something. But perhaps they're a little bit intimidated by this lack of having an audience and maybe even the idea of putting themselves out there is a little bit intimidating.

And I think it's interesting to call out like 10 plus years into your career, you've made the jump to be full time creator working for yourself. So can you talk a little bit about why you made that decision and then any. Lessons or strategies that you've learned along the way that you think other designers listening could use to get momentum on their own journey.

Tommy: There was a period in software where if you built a thing and you just kind of got a little squeaky wheel noise out there, you'd attract customers. Well, now we're like, software's eaten the world. It's saturated.

If you build it, they will not come. And that goes not just for software, but anything you create. It used to be search engine optimization was kind of the distribution model. And Google really cracked down on that because everyone found ways to exploit it.

For me, my first few companies, Reddit was such a great distribution model. , people exploited that and then Reddit's cracked down on that. , and social media was like paid ads for a while, but it wasn't, people weren't like really taking this idea of building in public seriously until a little later.

And then people realized, Oh, if I like, just talk about what I'm building and show the nuts and bolts of it, that's interesting enough that it tracks people who want to continue following what I'm doing and maybe even turn into customers. And what I would say to people today is I get the cynicism around creator culture, but it's no longer just like lifestyle influencers and memes distribution exists at scale.

And I view what social media has become today. Warts and all is kind of an indie movement. It really is. It's a response to corporations that are willing to just fire their employees when economic pullback happens. It's a response to all of the middlemen who like to take their cut from book publishers and record labels.

It's a response to essentially everybody needing to make one bet in a company as a laborer, and then have that bet completely turned on its head. I think that social media creators today, people who use it, it's weird to just like box it into one definition as social media creator. All it is is the new small business.

It's a new distribution that didn't used to exist. And so you might have a bad idea that you spend a lot of time on. And you've got 5, 000 people on TikTok or Instagram who are willing to give it a try. And that idea sucks. Yeah, you might lose a little bit of goodwill and you're gonna have to lick your wounds and think of something else.

But that distribution channel didn't go away. You still have it. And that's what's super cool is that when you have a distribution channel, it can do so many things for you. It can allow you to build a business on top of it. It can have you test ideas before you need to sink a ton of money into it.

Because people are going to tell you if they think that idea is worthwhile. If you're somebody who wants to knowledge transfer, if you see a problem in the market or you see a problem with how design is happening from your bedroom, these four walls of mine. I can try to make that impact. And what I would tell people is if you're starting out, if that's interesting to you, I want to let you know, you know, I've got almost a million followers across different social channels now and all of my content, anytime I ever tried to package an idea.

Right? We say content, but just ideas like I've tried to package an idea. Sometimes my ideas just don't hit. The execution is bad. Maybe the idea is not a very good idea. It happens like there's building in public and then there's like thinking in public, which is a terrifying prospect because you are going to get criticized.

But sometimes people aren't going to criticize you because only 14 people saw it. And that happens a lot, even to me still today. And the truth is, is if you take a short term approach to anything, I'm gonna share my ideas on, you know, TikTok or LinkedIn. And you're like, oh my gosh, after 30 days, this has been a dud.

I'm going to stop doing this. Well, that's going to be a hard way to get better. You can't expect to get any form of mastery. And one of the things I tell people is, you know, your first design or your first, you know, video or your first written sub stack newsletter is not going to be that great.

It's probably going to suck. But your hundreds, your hundredth is going to be pretty good, but you're not going to get there unless you do the reps to get there and you have to do those repetitions. And that just goes with anything. It's like that 10, 000 hour rule. So if you're starting out today, pick one platform, don't try to be everywhere all at once.

Don't do that. Pick one thing that resonates. Do you like to do video? Do you like to create images? Do you like to write? Or are those things that may be like, I don't know if I like to, but I want to try. Okay. Pick one and spend 90 days doing it. Just spend 90 days and practice, think in public, get through the ones that are going to be tough because it's going to be tough try, get stuck, learn, get unstuck

Ridd: I love the idea of thinking in public and also even highlighting the fact that like, man, there's just not as much risk in the beginning of your process as you think there is. Like when I made the decision to think in public, I was like, what if my ideas suck? And I've looked back on some of them and turns out, yeah, some of them sucked.

They totally did, but nobody saw them in the grand scheme of things. Nobody saw them and they were completely meaningless. All they were, were just me getting reps and being more comfortable writing and putting myself out there and even just being a magnet for people who. Have thoughts on similar issues and wanting to even critique things and being able to learn from that and iterate and take that into the next time.

So I think that's just spot on. Like if you're on the fence and you're, you know, struggling to just hit enter, send tweet, post on LinkedIn, whatever it is, make a video,

Tommy: Yeah.

Ridd: man, in the early days, nobody cares about you. And that's actually a blessing.

Tommy: Every single piece of content I've ever made, it makes you kind of a better designer because you treat it like an MVP, treat it like something like there's an idea, there's an execution, I'm going to put it out and I'm going to learn from that.

I used to think my ideas about moving quickly in dysfunctional situations.

Applied to everybody, but it's not true. There are situations where that's just not the case, and it really helped me see that. Okay, there are situations where that's true, and it's true at scale, but that scale is not universal, and that really helped me redefine how I talk about it when I use absolutes and when I don't.

And that has been a really helpful thing just in my life in general, because, you know, at the age of 37 now, I feel like I've experienced a lot of stuff. I start to think, Oh, the chances of me being wrong this time are lower. Well, it's been a nice eye opener to see that that's still, I'm still sprightly. I get it wrong.

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