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Away: Jen Rubio

from How I Built This with Guy Raz

76m 28s

Away: Jen Rubio

The transcript explores how founders and innovators build successful ventures by addressing fundamental, often overlooked questions—like whether an idea is viable, or what small decisions shape long-term outcomes. Anthropic’s foundation on public feedback about AI ethics exemplifies this, showing how deep, honest inquiry drives purpose. Similarly, Jen Rubio and Steph Corey discovered a gap in the luggage market, where travelers lacked stylish, functional, and emotionally resonant products. Their journey from a personal frustration to launching Away involved rigorous research, early investor engagement, and a bold pivot: creating a coffee table book as a pre-launch product to generate media buzz and pre-orders. This strategy, rooted in storytelling and customer pain points, not only built brand loyalty but also confirmed market demand. Meanwhile, financial and operational decisions—such as switching to a business credit card—highlight how small, intentional choices compound over time. The narrative underscores that true innovation stems not from grand visions alone, but from patient iteration, emotional connection, and the courage to ask hard questions. From travel to finance to AI, the recurring theme is that success begins with a simple, authentic inquiry.

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Our presenting sponsor today is Anthropic, the team behind Claude. Every founder on this show started with a hard question. Not the marketing plan, the 2AM kind. Is this idea any good? Am I the one to build it? Should I quit my job? Anthropic got built the same way. A public-benefit corporation founded on one hard question. How do we make sure AI goes well for people? So they asked, over 100,000 people, their hopes and their fears, and are publishing what they find, even the uncomfortable parts. Me? I've got my own hard question about AI. Here it is. If everyone has access to something that can help them write the business plan, build the prototype, analyze the market, maybe even come up with the idea. What separates the people who actually build something from everyone else? I don't have a clean answer yet. So I've been sitting with it with Claude. There's hope in hard questions. Ask yours at Claude.ai/hibt. We get support from US Bank. A question I love asking founders. 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And it reminds me a little bit of the founders I talked to on this show, because the best ones obsess over things their customers will never see. Tiny details and visible improvements, relentless iteration. And not because anyone's watching, but because it makes the product better. That's what the mobile brand does. It engineers fuel the same way great founders engineer their products. Mobile Supreme Plus Premium Gas helps keep engines three times cleaner, which can mean better performance and improved gas mileage. It's for people who care about what's under the hood, even if they never see it. Three times cleaner compared to mobile regular gas in port fuel injected engines. Actual results may vary. Visit mobilefuels.com for details. So the plan was launch before Christmas, get a lot of press, sell a lot of suitcases. But we found out when we placed our order that there was no way that our bag would be ready before Christmas. Which I don't know why it was so surprising to us. We were like, what do you mean? Like we have this timeline in the spreadsheet. And it said that if we ordered the bags by August, we would have them for the holidays. Yeah. And it was as if like someone had said like we had to stop doing the company. From NPR, it's how I built this. A show about innovators, entrepreneurs, idealists and the stories behind the movements they built. I'm Guy Ross and on today's show, I have a broken suitcase inspired Gen Rubio to design a better one. And in the process, disrupt the multi-billion dollar luggage industry with her Instagramable suitcase away. Did your team want a website that looks and feels handcrafted but is still fast to ship? Well, Framer is built exactly for that. With Framer, you design on a visual canvas with responsive layouts, hosting and a CMS built in. So the work is production ready from day one. And you can get it done with help from Framer's AI agents. 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NetSuite Next surfaces insights exactly when you need them, puts agents to work on routine tasks and problems and lets us complex questions in plain language, like talking to a knowledgeable colleague. But technology is only part of the story. AI is also reshaping how people and teams work together and that shift is already underway. That's why NetSuite wants to put a new expert created business guide in your hands today. It's called aligning for the agentic era. How AI is changing every day work and right now it's yours absolutely free. Inside you'll discover how AI could reshape work across your entire organization and how to position your business to prosper from it. If your revenues are at least in the seven figures, get NetSuite's free business guide aligning for the agentic era. How AI is changing every day work at NetSuite.com/built. The guide is free to you at NetSuite.com/built. NetSuite.com/built. 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So when you're standing at the baggage carousel at the airport, waiting for your bag to come around, and there's like a never-ending parade of black suitcases going by, and every now and then the person next to you rushes to grab one of those bags only to realize it's not actually hers. This is a pretty common scenario, because for a lot of people, a suitcase is just the thing you shove all your stuff into when you go on a trip. You might have bought it for 50 bucks at TJ Maxx or on Amazon. And most of the time, you shove it into a closet or under your bed between trips. And it probably only lasts a few years before the zipper breaks or the handle falls off. And most of us have always accepted that, that's just the way it is, right? Well, Jen Rubio didn't think so. And back in 2015, she had a hunch that other people might agree. She hated how mid-range suitcases were designed, they seemed boring and uninspired. She wanted something that would last a long time and she wanted to create a bag that would be eye-catching, something you'd want to show off at the airport. And so Jen approached a friend named Steph Cory, who worked with her at Warby Parker. And the result of that partnership is, away, it's a line of sleek suitcases that come in tons of colors like rose gold or violet or sky blue. And with perks like a built-in phone charger, the kind of bag you'd want to Instagram while you travel the world. And Jen's own story of traveling the world? It started when she was a kid in the Philippines. Her mom was a dentist and her dad was a business professor there. Until one day, when Jen found out that their lives were about to change. I remember when I was 7 years old, my parents told me that me and my brother and my mom were moving to the US and we'd never been and we were so excited. And they told us stories about how in the US it snows and we went to this giant mall in Manila and bought snow suits, I had a pink one and my little brother had a blue one. And we wore them on the plane, so this was my first big, big flight with my mom. My dad stayed behind because he didn't have a visa yet. And we wore a snow suit, I remember just being very sweaty on the plane. And this was like, I don't know, late September. You were wearing your snow suit on the plane to the US. We insisted. We told my mom we're like, it snows there, we read about it. We landed in New York airport in September, sweltering, it was super hot. And I think that was the first time I'd ever really experienced true disappointment. Why did you guys move? Do you know what the reason was? Was it just like new opportunities or what? Yeah, that's a good question. I mean, we had a great life in the Philippines as far as I remember, but it was presented to us as a very exciting opportunity that not a lot of people got. We had a couple of aunts and uncles who already lived on the East Coast and we were going to join them. And we'd never even met these aunts and uncles, so we were super excited about it. Obviously looking back now is just for my parents to continue to grow and have more opportunities to develop their careers and give a better life to us. Eventually, Jen's dad was able to join the family in New Jersey. Her mom opened up a dentist's office and her dad ran the business side. And Jen started to settle into her new life in America. Did you, as a kid, did you, like, were you immersed in Filipino culture or? No, totally the opposite. I think there was like two different experiences of immigrant kids and they're the ones who embrace it. And they're the ones like me who are just immensely embarrassed of the experience. And I think it had a lot to do with, you know, the other kids at school or like wanting to fit in or, but, you know, I only spoke English. I would, like, get mad at my parents when they would cook Filipino food because it would make, like, my school jacket, like smell like food. And I was just, I don't know, I was like, I was a kid and I was just so embarrassed of the whole thing. And you kind of don't come to terms with that until you're, like, really 20s. Yeah. We start to kind of realize that it's this hugely rich part of who you are. Yeah. And it's so valuable and it's so important. And I just, I spent, you know, probably the first 10 years being in the U.S. and just like being embarrassed of being Filipino. Jen was a pretty good student through high school, despite, as she says, being more interested in being cool than doing well in our classes. And when it was time to go to college, she chose Penn State. And it was, like, TV college. It was a college in the movies and there were football games and there were tons of people. And, you know, everyone's wearing, like, school colors and there's, like, a quad. I know that's normal on every campus, but it was just, like, all of the college things you saw in movies. And I was, like, this is amazing. And I picked a major called supply chain. It was like, like, in the orientation they had said, you know, they were one of a handful of schools in the U.S. offering supply chain as a major. And I was like, cool. How exclusive. And I chose that to study. So you're doing, like, you're in college and I guess you decided that you just, at a certain point, you had an opportunity and it, and it meant that you didn't go back to college. Like, what, what happened? Yeah, so I was, I was taking a bunch of classes in the business school and they had at Penn State what's called a co-op program, which is you take a semester off and you work for six months at a company. And I was hating school and I was hating going to classes and taking the tests and actually having to apply myself. So I read about this program and I was like, cool, you get credits and you don't have to go to school. And I decided to do it and I was placed at Johnson and Johnson in Skillman, New Jersey. And I remember getting there on the first day and it's, you know, it's a, Johnson Johnson is a huge company and this was their headquarters and they told us something mind blowing on the first day, like, you know, 140,000 people work here and I just couldn't wrap my head around that number. I remember I kept trying to relate it back to like the Penn State football stadium and how many people could fit in there. And I was, I was just enamored with the whole thing. I like, I got a cubicle and I got an ID badge and I had my own desk and my own phone number and my own email and an email signature and just the idea of work and being like a business lady was so exciting to me and I just never wanted to go back to school. But I had to. So it ended. I had to go back for a semester and I was just so miserable. I had felt like I knew what was out there. I knew what it was like to work. This whole corporate world existed and it was thrilling to me and I wanted to be a part of it. So after a semester back at school, I got another co-op and this time I got placed at Neutrogena, which is also owned by Johnson & Johnson in LA. And I asked them to extend it for a summer internship and then I asked them to extend it into another thing. I just begged to stay. I like couldn't fathom the thought of going back to school. And I don't know how I did it but they let me stay and they made me like I promise that I would take the rest of my credits online and that I would finish and get my degree. Yeah. And I never did. And they offered you a job. Yeah. And I basically was just like the intern who never left and I was invited to walk a graduation but I think I'm still three credits short. So you see your technically a college dropout? Yeah, technically a college dropout. Yeah. I think people are like, "Oh cool. You're a college dropout." No, I dropped out of college so I could work in a cubicle. This is like 2006, 2007, you're in your early 20s living in L.A. you're working for Neutrogena and that was your plan at that point. Yeah. So I was working at Neutrogena and one woman that I really admired and that I had never spoken to her personally but I just remember recalling like every time she sent an email like everyone would open it and everyone would read her analyst reports all the time and every time she spoke like people would listen and she ran marketing and I was talking to kind of my mentor about her and I was like, "Okay, how do I get a job in marketing?" So this woman's like, "Oh well to work in marketing here, you need to get an MBA." And me being me, I didn't think to myself, "Oh, I should finish and get my undergrad degree so I can go get an MBA." I was like, "There must be some way around that." And there wasn't. But now like this, it opened up this whole new world to me of being able to work in marketing which to me at the time meant that you could control how people found out about your products and how you could take everything that people were saying about it and maybe change the products and I just thought it was so cool and I knew I really wanted to do it and that if I couldn't do it there I would find somewhere else that would let me do it. So I quit. And did you have a job or did you think, "Okay, I'm going to figure this out. I'm going to try and do marketing for people and just figure it out." Yeah, I was like, "I'm going to do marketing, I quit and I didn't have a job and I don't have a degree." and. And I didn't have that much money. But I had, do you know that platform Tumblr? - Yeah, sure. - So Tumblr had, I guess maybe just started, and I was like one of the early people on it, and it's what, you know, I would do in my spare time. I would like write on my Tumblr blog. And I had met a few people in LA on Tumblr. One of the guys I met did social media. And I was like, what do you mean you do social media as a job? Like I had my space, I had Tumblr. I had Twitter, and I didn't know that you could do that, and also that it was part of marketing. But he would do social media for some of the OG food trucks in LA. - He would like control their Twitter or whatever Facebook, whatever was around at that point. - Yeah, and it's so wild, it was literally Twitter. And doing social media for a food truck meant you would just tweet where the truck was gonna be, which sounds so crazy now that was someone's job. But I remember like following the Twitter account, finding out that the truck was gonna be like on the corner of these streets in LA, driving over there, and there would be hundreds of people there. And I don't know why, but it just blew my mind. I was like, you can just tweet where you are, and like people will come. And that's, that that was their business. Otherwise, like the truck would have just sat somewhere and you had to maybe drive by it. And I think it was like, this is marketing. Like this is how you get paid to do marketing and do social media. And these are all things I was interested in. And I was like, I got this, I'm figuring this out. So I started being like a freelance consultant for social media. - You just put your like, you just like hung a shingle out. Like how did you get people to hire you? How did you know where to go? - Honestly, so much of it is luck. It was really a lot of the right place, right time. I was living in LA, it was when food trucks were a big thing. - Yeah. - And I kind of just spread the word. I would go to small businesses and to food trucks. And my first client was the cafe on my street. It's not around anymore, but it was this little cafe on Beverly Boulevard. And I would, let me sit in the cafe all day and tweet things like, there's a password of the day. And if you say the password at the register, you get like a free espresso shot. - Oh wow. - It was such amateur hour, but there was also nobody doing it. So I found myself in this situation where I am getting paid to do something. I don't know that much about it, but also at the same time, everyone saw me as an expert. And it was one of the wildest years of my life because my first client was Buzz Coffee. And I don't even know if they paid me, like I think they paid me in coffee. And then all of a sudden I was doing it for a food truck and a restaurant. And then all of a sudden, they introduced me to someone and I was doing it for a new hotel that was opening. And then all of a sudden I'd realized I just spent a year being immersed in digital and social media and realizing how people could use that in a really powerful way. Like I also wasn't making a ton of money, but I was also doing personal assistant stuff. So I was a personal assistant to the wife of one of the heads of one of the very big studios in LA. And then she had asked me to help her with her blog and her social media and her website. And I started helping her with that. And then she told her husband I was doing a great job. And all of a sudden I find myself like driving up to the lot every day, like checking in with my ID and meeting with these film executives, talking about how they could market their films like through social media. - And this was like all, this is at the time when it's just starting to explode, right? And so primarily this was like Facebook and Twitter at that point, right? - Yeah, it was just Facebook and Twitter. Like my space was tapering off. - Yeah. And I mean, you were just sort of doing this as you went along, right? Like you weren't, you didn't set up a business or a company or you didn't sort of show the companies how their social media impacted the world, right? You weren't like producing reports for them. You were just out there doing the social media stuff and we're hoping that they were happy with it. - Yeah, exactly. And there were no metrics. There were no analytics of any sort at this time. And I would just be like, look what I tweeted. Look at all these people that responded. Look at these people who showed up. And for me, it was, that was actually great because it wasn't reports. It was like real tangible stuff. It was like people showing up and saying something. We're doing something or spending money at the business. And that was really exciting for me. - I just want to skip ahead for a sec because I guess eventually you were able to get a job at like a legit ad agency in New York and then you started to do this type of stuff like marketing for real. And then in 2011, you got recruited by Warby Parker. How did that happen? - So I have Tumblr to thank for this one again. So my friend Rich who worked at Tumblr was like, you should meet with these guys. You're starting this glasses company online and they just want to talk to someone about social media. And I remember meeting this guy who worked at Warby Parker and we met at Union Square Park. And I remember realizing kind of halfway through our conversation that it was a job interview. I thought that I was just like coming in there to like chat with them about the startup and they would like pick my brain and that was something I was like really open to. And I left being like, I think I just interviewed to be the social media manager at Warby Parker. And that's how I got started in the startup world. - They, to the co-founders have been on this show before and the social media stuff never really came up. Did they have a social media strategy when you got there? I mean, it's still, this is still like the stonage of social media compared to today but did they have like accounts for all the different social media stuff and. - Yeah, I mean, it was still the Wild West. Like so there was a Twitter account and that was basically for customer service. And the guy who interviewed me, Brian, his whole job was like replying to everyone on Twitter which then became my job, which just spent like 10 hours a day replying to people. Even if the even people would be like, I love Warby Parker, I would reply like, thanks like hundreds of times a day. They're on Facebook, on Twitter, they're on Tumblr and Instagram launched right when I started. So I was like, guys, there's this cool platform. I think we should go on it and they're like, okay, cool, whatever. - And what did you, what did you do for them? I mean, like what, how did you start to use like things like Instagram to expand their brand? - Yeah, so I think I started thinking about like what a content strategy would look like. How do we take this amazing thing that we're building that's kind of weird, which is selling glasses online? All of my friends thought I was crazy for doing this. And like how do we translate that experience into like a social media community? And we would do things like, like Warby Parker had that like home trion program where you do try on five pairs of glasses and we would do it so that like people would post their five and like we'd repost it to our Tumblr. - And they would like post to those of themselves. - Mm-hmm. And then like our community would like help them pick. And that was like a big thing on Tumblr and Facebook. Like we would basically crowdsource what frames people should buy. And we would just build this like really loyal, really engaged community. And it just kept growing and growing. And I think it's all embarrassing to kind of like, look back at your work, especially in those early days. But I really was just like, I really could feel how social media was having an impact on how much people loved the brand. And that was really special to me. - When you were at Warby Parker, did it ever cross your mind that like, I wanna start my own business one day or was that not even on your radar at all? - No, I never wanted to start my own business. I never wanted to be an entrepreneur. I think I was just so grateful to have found work into something that I really enjoyed. And for me, that was like social media and marketing and eventually brand development that because those opportunities seem so limitless and that I never felt like I could learn everything there was to know about what I was doing that it never occurred to me to start my own thing. - So I guess you sort of lasted at Warby Parker for about two plus years. And you were recruited or you got a job with all saints, which is the fashion brand based in the UK, to be their global head of innovation. You were like 26, 27 years old. How did that happen? - So yeah, so when I joined Warby Parker, there were maybe 15 people there. By the time I left, there were a couple hundred. So it was still growing really quickly. I still left like pretty early days, but my father passed away while I was working at Warby Parker. And it kind of slowed down a little bit after that. And I started thinking a lot about what I wanted to be doing. And coincidentally, this headhunter called me at the same time, I was kind of going through that. And moving to London seemed like one of the most exciting things I could do and I was so drawn to the opportunity. The job was interesting, so it had really not. thing to do with anything I'd ever done before. So I became the Global Director of Innovation at All Saints and this is when they were trying to turn the company around. They had new owners and new CEO. I was 26 or 27 and I had a seat at the table with all these like very seasoned executives from like from self-ridges and herrids. And they knew they knew your work from Morby Parker and they wanted some of that magic for their brand presumably. Basically the new CEO at All Saints, I think had just wanted someone from Morby Parker. But yeah, I mean it was like great job, great title, like I got to live in London. I didn't realize until after the fact that what was missing is that my entire career had revolved around the idea that there was a brand and that someone in the middle does something and then there's a customer at the other end who falls in love with it and I built my entire career around like that middle part like being the gap between the customer and the brand like building the relationship, making people fall in love with the company and because all of my projects at All Saints turned out to be internal facing and more like internal innovation, I realized that was the part that I really missed. I wasn't wise enough to realize that at the time but I think that's basically why I was so bored. So what happened? What did you, I mean, were you just kind of waiting to figure it out? Yeah, I was waiting to figure it out. I always promised myself that I would only work on things that made me happy especially after my dad passed away. It was like really important for me to to spend my time doing things that I was really passionate about and I knew that had kind of dried up for me in this opportunity. And so I left I left All Saints and I was still living in London kind of for a finite amount of time because my visa was going to expire. So I started interviewing for jobs. I interviewed for like VP of marketing, like CMO jobs at companies of all different sizes. And during this, I was completely just on a tear around the world, splitting my time between interviewing and like going on vacation. So I'm in Zurich Airport and my bag breaks and it was this old bag that I'd had like since college, I guess. It's like no name, like black ballistic nylon bag. And it was super embarrassing. Like I didn't realize it broke that I didn't realize it broke. So I'm leaving a trail of like my underwear behind me as I'm running through the airport. And I get home and I go on Facebook and I tell everyone about this embarrassing story about my bag breaking and I ask people if they have any recommendations for a new bag new bag. Yeah, this was just me really like just trying to shop. This is like this is like 2015. This isn't that long ago. Yeah, this was 2015. At that point, I traveled hundreds of thousands of miles in my life with this one bag. And I was super annoyed and I was just like, okay, I'm just going to buy a really nice bag that I love and this won't happen again for a long time. So I ask a bunch of people and every single person is like, I don't know or I have this but don't get it. It's awful. Or or I would specifically ask a friend that I knew traveled a lot. And he or she would be like, oh, I don't actually know what brand I traveled with. And I think it was so crazy to me that all of these people, including myself, who loved to travel, who did it all the time, who packed a suitcase every time they traveled, really had no connection to this thing that they brought with that on every single flight on every single trip. But like most people would go to like Target or TJ Maxx or something or or or or or Marshalls and just like go to the suitcase area and get a suitcase. Yeah. And I didn't want to do that, which is why I asked everyone. And then I found out that like no one really had luggage that they loved. There is one girl who really loved hers and it was like $4,000. Wow. Even though they make $4,000 luggage. Yeah. I know. Me neither. So what I thought to myself was I have to find this brand. Like there has to be a great luggage brand out there. Yeah. Like I didn't I didn't think like I'm going to start wide. I was just like you were not looking for like just to be clear. You weren't looking for like a category to start a business in. No, not at all. Not at all. No. I was like I like wanted to go shopping. I wanted to buy the right thing so that this wouldn't happen again. And I was I was crowdsourcing for answers and I I didn't get an answer. And these are people who I have like a mass a network of friends over time who whose tastes I really trust whose advice I take and no one had any advice for me. Everyone was like good luck. So I started to think why doesn't this luggage brand exist? Like how come buying luggage is so awful? Like how can we have to go into like the basement of a department store or or in New York? There's all these like crazy luggage stores in Midtown that are massive and and you go in and there's a $500 bag next to a $50 bag and they look exactly the same. And like the luggage salesman is like whispering in your ear like I can give you 30% off if you buy it right now. I was like why is this so horrible? So that's when I maybe thought that I could start something like at this point I was interviewing for jobs and in my head I was like I can start a little luggage business on the side and like make it like some cool brand and maybe sell it at like at Liberty or on Netaporte or like these cool places that I like to shop and that's when I caught up with Steph. When I was at Werby Parker I met Steph Corey and we we started on the same day and we became fast friends and we were friends all throughout my time at Werby Parker. What did she do at Werby Parker? She ran supply chain there so she was in charge of how the glasses were made like the factories that we got them from like how they got to the states to be shipped to customers just like stuff that I actually technically went to school for but really didn't know much about but we kind of went through this like the crazy growth of Werby Parker together and we stayed friends and we'd like loosely kept in touch and we check in every few months. So just as this like this little baby idea of of making luggage that my friends would love was brewing in my head I reached out to Steph and like I said our Facebook message and I said hey there's something I've been thinking about would love to catch up with you and she was she was in business school at the time so she left Werby Parker. Yeah she left Werby Parker to go to business school at Columbia and she'd just always been my sounding board so I called her to catch up and I was mostly complaining I was like this luggage brand doesn't exist like I have a bunch of ideas like I think I think I could make like a cool one but also how annoying I have to go interview for this other job and we're just catching up and this was supposed to be a 10 minute call and like three hours later we were still on the phone and basically she was in business school and she had been looking to start something and she was the one who was like what we did at Werby Parker we can do with luggage and we basically got off the phone and she realized like all the same things that we saw with I wear we were seeing with luggage like crazy markups in the industry like no brands that people really loved like a really awful shopping experience so she was coming at it from this whole like like supply chain disruption angle and she's I guess she was sitting there in business school like looking for her category and I basically called her with my little baby idea to start a luggage brand and she was like this is it like this is what we have to do when we come back in just a minute how Jen and Steph turned this baby idea into a reality and how a copy table book saved their business stay with us I'm Guy Ross and you're listening to how I built this from an PR confidence it's listening to your god it's moving forward even when the path ahead is unclear for nearly 160 years pacific life has helped people keep their promises building confidence for generations whether you're confident in your financial future or just beginning to envision it we're here to help ask a financial professional how pacific life the power of a promise pacific life insurance company Omaha Nebraska and in New York pacific life anonymity Phoenix Arizona hey welcome back to how I built this from NPR okay so it's 2015 and And Gene Rubio and Steph Corey have this idea for a better look. luggage brand, but to start working on it, would take a leap of faith. Because at the time, both of them were interviewing for other jobs. - So I was still living in London, and I was in pretty late stages to be VP of marketing at this fashion company. Stuff was in business school and talking to a few startups about being like their VP of supply chain. And I was actually being flown into New York for one of my final interviews. And I realized as I was doing the interview, that I was like, "I don't wanna do this." I like, "I wanna do the luggage thing." It's like, "I do the interview." I don't even remember how it went. But I got the job offer, and I really didn't wanna take it because I had been so excited about this idea for a luggage brand that I actually wrote I wrote stuff in email about how I never wanted to be an entrepreneur before, but I was really passionate about this idea. And I thought that we were the two perfect people to do it. And I made a whole list of everything I wanted co-founder and then explained how she embodied all of those things. I wanted someone who had a complimentary skill set and had other lucrative opportunities that they were turning down to do this, which was like a weird qualifier, but it was really important to me. And it wasn't until I wrote that email, like asking her to be my co-founder and asking her to do this with me, that that was the point I kind of realized I wanted to be an entrepreneur. - Did you come up with the name already at that point? - I think everyone's always looking for some wild story about how I came up with it. But as I was doing my research, I was like trying to stay organized, and I made like a folder on my computer. And it was like TBD luggage brand. And one day I like opened my computer and I just typed it away as a placeholder, like it just came to me. And I always had it in my head like, there's no way we can use like a way as a brand name. It's like just such a simple four letter word. It's like extremely common. And then stuff and I actually spent a lot of time like brainstorming new names, but we just never came up with anything as good. And she found like some trademark lawyers and asked them if we could trademark it and they basically laughed in our face. And she was like, she like insisted that they looked into it. And then a week later they called us and they said, you have been given a gift from the marketing gods because this trademark is available in your category in a lot of different countries. - All right, so you have a name. And what's the first step, like how do you, how do you get the luggage made? Like where do you even start? - Yeah, so kind of like our first steps made sense to us because we are who we are. I had this branding background. She had this supply chain background. And I was like, okay, we need to get a branding agency. Like we need someone to do this. And it was like, we didn't even have a product. We didn't even know how to make it. But I was like, I'm gonna start working on the branding. - And you have to design it? Like design what the suitcases are gonna look like. - Oh yeah, I didn't even think about that. I was like, I can sell anything. (laughing) I was like, we have to brand it. She's like, what are you branding? I'm like the company, don't worry about it. But she kind of went with it. So that's where my head was at. And stuff was like, okay, well we have to like come up with a product to sell. - So how did you find, like I mean, how did you even begin? Because I have to assume that suitcases probably mainly made in China. But like in terms of finding a place to make them and designers and like what did you do? How did you know what to do? - Yeah, so we at Warby Parker, stuff basically learned how to make things. And obviously the industries are different, but she had a bunch of contacts in China who she asked for intros to like in the luggage space. You know, we cast this wide net. We realized that there are lots of different factories like a varying degrees of being good at what they do. And like varying degrees of working conditions and like in the end product and all of that, that we couldn't really make a decision until we had decided what to make. And I think the first few weeks were just like really intense, like our intense version of like market research, which basically meant we went shopping like every single day. We went to every department store. We went to every luggage store and like compared all of the experiences and all the prices and like kept very meticulous notes on what was out there. Mainly because we couldn't afford to like pay for the industry reports. So we're like, we'll just figure this out ourselves. So we started shopping for luggage and we're like getting a better sense of like what was being offered. It still wasn't super clear to us. So we decided that to really create the perfect luggage, we need to actually figure out what people wanted. So over the course of a few months, we talked like maybe 800 people. And we would just talk to them about travel and we would ask them things like not even about luggage, but about their biggest pain points when they travel. And we discovered things like people get to hotel rooms and they would like steal laundry bags from the hotels because like they didn't have their own. Or that, you know, everybody like wanted a bag that they could fit a ton of stuff in but also have it be flexible but also really durable and like really lightweight. And then something we heard a ton was my biggest pain point, like one of my biggest pain points when I travel is like my phone always dies when I'm at the airport. So we were basically armed with not elusive features but stories that kept coming up. And that's how we figured out all of the things we needed to make like our one perfect suitcase. So as the design process began, like how did that work? Like what did you want the bag to look like? - Yeah, so basically, you know, Stephanie had this list and then I knew what I wanted it to look like. And you know, we were basically up like 20 hours a day because our industrial designers were in San Francisco. We had factories that we were talking to in China. Basically the second one of them wrote us an email like we would make sure to write back or pass it on so there would be no delays because also in all of this and to this day, I don't know where it came from but you know, this was like January, this was like February of 2015 and we had it in our heads that we wanted to launch by Christmas. So in less than a year, we wanted to have like product out into the world. And luckily like we really didn't have anything else to do so we just like immerse ourselves fully in this and we're just obsessed with every single detail. - So I guess, I mean, it's amazing is by, I mean, this idea really begins in 2015, like January, February of 2015. By November of that year, you guys managed to raise, I think like two and a half million dollars from VC companies. - VC is. - Yeah, was it, was that hard to get? I mean, was it hard to make the case? 'Cause it sounds like it was pretty easy. I mean, pretty quickly after the idea. - Yeah, so in March of 2015, like when this was barely an idea, like we still didn't have a ton of direction what we were doing, a friend of mine in San Francisco introduced me to Yuri Kim, who's a partner at Forerunner and Forerunner is the VC firm that invested in Warby Parker and Everlane and DollarShaveClub and Jet.com and they just had like these amazing portfolio and these amazing wins and we had heard about them obviously when we worked at Warby but didn't really interact with them. And my friend was like, I'll introduce you to one of the partners and me, like I just had like the audacity to schedule a meeting with her even though we literally had nothing. At this point, we still thought away it was a placeholder name. It was just like an idea to create this thing and we were basically just like in the throws of doing research but I was in San Francisco and I met with Yuri and I kind of like, it was basically just like a meeting of me being excited about what we were doing. In my head, it wasn't like me pitching her but because of that, like because of that early meeting and because of like her wanting to stay in touch and being excited about the idea and seeing how excited we were about the idea. Like we stayed in touch which meant that when we actually went out to raise our seat around in the summer, we already had like a like a foot in the door with one of the firms that we wanted to partner with. And we pitched a lot of, we pitched a lot of VCs. It was like a crazy process. We were like super diligent. We had this crazy spreadsheet of every single venture capital firm who'd ever invested in a direct consumer brand. Who the partner was at each firm that did it. If we had any like mutual connections on LinkedIn, like how we would get to them, we had this like crazy master plan for fundraising. - So you really thought this through. You were really methodical about it. You and Steph were really, I mean, you really did your homework. - Yeah, I mean, I think part of it was that like that deadline to launch in 2015 came from nobody but us. But we just, we really wanted to do it. I don't even know where that timeline came from. And you wanted to do it in time for Christmas. - Yeah, we wanted to do it in time for Christmas. Yeah. We're like, this would be like a great way to launch. Like get a ton of press. So we had this like self-imposed deadline looming above our heads. But like once we got it, wrote the timeline down, we stuck to it, and that meant being super methodical and everything we were doing, whether it was designing the product or fundraising or just literally anything that we were doing. So we raised the seed round in the summer, and we talked to a lot of investors, and Yuri Kim, a forerunner, ended up co-leading our seed round, and she actually brought in the other co-lead, which was Brian O'Malley from Excel at the time. But you guys, I mean, by that summer, you get your- you get your- Two and a half million dollars. Two and a half million. So what was the plan in the summer of 2015? So the plan was to launch me for Christmas, and we had known from previous experience that this was like a very lucrative time to launch something, all the media does gift guides. There's also like a lot of demand for like human interest stories and things like that. But all these angles that we wanted to hit. But basically the plan was to launch the suitcases and get a lot of press, because we knew from Warby Parker that the press was a big part of driving sales. Right. They had this like article in GQ or Vogue or something that just like blew up for them. But this was already July, August of 2015, like the big magazines are already- They're already making decisions about their Christmas issues at this point. Their gift-giving guides at this point. Yeah, so we didn't do that at the time. We were like, got months. Our whole thing was launch before Christmas, get a lot of press, sell a lot of suitcases. But we found out when we placed our order in August that because of the way we designed the bags, and we used like all of these like top of the line components, and we had looked at like every single supplier and wanted all of the best things from all the suppliers. That there was no way that our bag would be ready before Christmas. Wow. Which, I don't know why it was so surprising to us, we were like, what do you mean? Like we have this timeline and the spreadsheet, and it says like the spreadsheet that we made up. And it said that if we ordered the bags by August, we would have them- You would have them by Christmas. Right. And it's so weird that this whole world did not adhere to our timeline. Yeah. Even though it was a self-imposed deadline. At this point, we'd actually started, like we didn't even have a suitcase yet and we'd already started talking to editors and to like potential PR agencies about what we were doing, and we had gotten some really good feedback. So- But didn't they want to see the suitcase, or did you- were you sending them like photos of it? We were sending them like like 3D renderings, and we were mostly just like selling them on this idea that like before us, amazing affordable luggage did not exist. And beyond that, that there was like this whole brand that was obsessed with travel, the way that they were, and that we were creating it. So people were just excited about that. And when we found out the bags weren't going to be ready, we were like, okay, what are we going to launch? Like we can't launch suitcases. So basically our options were like, don't launch or push it back, which it wasn't on the table for us for whatever reason. Or we could launch with a pre-order, which I think is just like the most boring thing you can do when you're launching a brand, like no one wants to put their credit card down for something that they like may or may not get. So we came up with this idea, and the idea was that we would come up with something before Christmas that people would want to buy that would show them that we were like this amazing new travel brand they never heard of. Right. So the idea was to write a book, neither of us were writers. For a single suitcases come off the factory line. So I was just like this freak with all these crazy ideas and stuff would be like, okay, we can make this work. We were just total enablers. Was it going to be a book of your photos of your luggage? No, so basically I was like, we're sitting in this week, we're like, okay, we have to show people that we're an exciting new travel brand and that they're going to love us. So the book was we were going to find 40 taste makers, like not celebrities, but people who had really strong communities, like people who we wanted to vouch for us essentially. And my friend, who was like a freelancer for Team Magazine and Vogue and into the gloss, she was going to interview these people about like their favorite place to travel to. And she would write the little blurbs and then we realized that like we would need photos in the book or it'd be really boring. So she would also ask them for their vacation photos. And we came up with this list of people that she would interview. And the whole plan was to write this book and we had two, it was just us and two designers at the time. And we got them to agree to design the book. So we're like, we're going to make a coffee table book and then inside the coffee table book, we're going to put a gift card that people can redeem for the luggage. Wait, let me just pause for a second. You had raised two and a half million dollars from VCs who wanted you to make luggage and you were now using that money to come up with a coffee table book of people's vacations. I didn't even think about that. I just wanted like did anybody say, hey, what are you guys doing or did they not really know? Well, it's actually funny because when we were trying to choose our investors, a lot of the feedback that we got were like, oh, you're creating the Werby Parker for luggage. Great. We'll invest. And those are super easy conversations. The other feedback was like, you know, we would show them a picture of the luggage, like a rendering of the luggage and they'd be like, I don't get it. It's just luggage. Like what's different about it? We're like, well, here's all the great things about the product. But also, and then I would go on and on about this brand that we were building. I would like ramble about the brand and I was like, we make luggage, but we're a travel brand and it's really going to connect with people. And that's the whole idea for a way is that people didn't emotionally connect with Samsonite or Tumi or any of these other brands. And basically, the VCs that we ended up going with were the ones who got that brand was this tangible thing that we could make uniquely ours and that's what it would set us apart. So every time and even now, like every time we come up with like some crazy idea like this, they're like, okay, it must be for the brand. So no one questioned what we did. Yeah. Where were you going to sell the book? So we were going to, that was like the book was the thing that we were going to sell. So we had set up this whole website to sell luggage that wasn't going to be ready. So then we changed the website to sell the book. Wait. So if you went on the away website in November of 2015, you could only buy the away coffee table book. You could not buy a suitcase? Yeah. I mean, I guess, I guess like a different way of looking at it would be like you would, it was basically a pre-order for the suitcase, but you would get the book. And the reason we did that was because we wanted people to be able to give people things for the holidays, like something tangible. So yeah. So if you went on the away website in November of 2015, you would buy the coffee table book and the book would come with a gift card for the suitcase, but you would have to go back on the website in February through the gift card. And it was like the craziest, like least efficient idea on paper, and even now as I'm telling you. But stuff was like, you know what? I think this could really work. And we made 2,000 of these books. And I remember like the books got delivered and they came these huge boxes. And I think Steph and I looked at each other and we were like, this is either a great idea or we're going to have these books in this office, like fraternity, which is like these thousands of books showed up. So in November rolls around, we had lined up a bunch of press, we invested a ton of time in meeting with editors, like getting them to fall in love with us and the idea and the product that would eventually launch. And on November 9th, 2015, we woke up and there's a big feature on Vogue.com. All about this new travel brand. And that was our launch. And we had the book on the website and we basically spent the whole day, like refreshing Google Analytics, refreshing our, like our little dashboard for the platform that we were selling on. And people just started buying the book. Wow. And how much did it cost? Well you had, so basically you had to buy the book for $225, which was the price of the first suitcase. And we sold hundreds on the first day. On the first day. On the first day. So Vogue wrote about it, a bunch of other outlets picked it up. All of the people in the book were like really excited about it. We had like a big dinner, everyone's posting about it. And then the next day, like hundreds more sold, and then more the next day. And by the end of a couple of weeks, we had sold out of all of the books in each book represented one suitcase that we ordered. So we had sold out of our first order. And at this point, you still did not have a single suitcase, like in stock in the US. No, so basically every suitcase that would come in February was accounted for. So February of 2016, the suitcases were going to arrive from China. Exactly. And where, like, did they come in like a giant shipping container to like a warehouse in New York? Yeah, so it's actually great because, so this, like the holidays happen. We sold the books, like our minds were blown. And we were like, look at the appetite for for this brand, like all the stuff we told VCs is real. And we actually weren't sure if it would be. So that felt like it. great but then we were like okay we actually have to get the luggage over here. So right after Christmas we flew to our factory and we actually spent days like in the factory on the production line doing like quality control checking every suitcase. Like Steph and I were like we're standing there with all the factory workers like we inspected every bag off of the line. They got packaged in their boxes. Were you happy with them? Do they look do they look the way you want them to look? Yeah it was it was a dream come true because we'd basically spent an entire year just just imagining it and designing it and like and putting in the work and I had never been a part of that process before of like coming up with and designing something from scratch and then seeing the end result. So there were a lot of tears it was it was like a very emotional time but we were they were like I was like on the factory floor like crying like hugging the suitcase but yes so that was January we like you know they put them on a boat and they made their way over and we sold our first physical suitcase in February of 2016. Wow that year I think in your first the first year where you actually had the suitcases you you ended up selling 55,000 suitcases which is amazing how did how did people find out about them. I mean I think what we saw pretty quickly is that our timing was perfect like we were in this time in social media where travel is a status symbol everyone wanted to post about not just their trips and like not just about the beach that they're on or like the mountain that they're skiing on but but how they got there and people were taking photos at airports or or even when they were packing. And Steph and I realized that like we had to be a part of this and we had to be the bag in all those photos that people were posting as they were packing or as they were at the airport. So we basically found I mean in the beginning in the beginning it was a lot of press and then it was a lot of basically anyone we knew on social media that had a lot of followers like asking them to post about the bag during that kind of like pre-trip process and we made it so that anytime you would open Instagram and someone was like getting ready for a trip they would be posting a photo with their waist suit case. How did you I mean pretty I guess pretty soon you were getting I mean celebrities were starting to use the bags like Rashida Jones and Carly Claus and I mean did you did you deliberately seek them out and say hey check out our bags or how did that happen. I think what happened was we'd give it to a couple celebrities and I can't remember who but you know celebrities get their photo taken by Paparazzi when they leave the airport so the bag would start showing up like in all of these magazines as as celebrities were leaving airports so I think that did a lot for growing our customer base and also other celebrities seeing it but I think what's been amazing is that like celebrities were so drawn to the brand that every celebrity collaboration we've ever done has been because that's the lab has been a customer and it was crazy like I don't I don't know how it happened like when we first launched the book and we were like looking at the orders come in you know we would see the names of every single person who ordered yeah yeah and I remember be like oh I know that person from college like they must have seen on Facebook or or like I used to work with that person and it'd be like names of people we knew and then maybe like names of people we didn't know but then once in a while like you know we're watching orders come in one day and Laura Jean with her spoon ordered a bag and Steph said Steph said it out loud and I was like that's Reese with her spoon that's her real name she's like that's so weird that you know that but yeah like she had heard about it from like one of these articles or one of these influencers and she ordered a book so she actually has one of our like original books and the bag you started this company just the two of you in 2015 how many how many employees do you have now we've close to 250 employees wow I mean it's it is pretty unbelievable like you know the one hand it is unbelievable right you start this company in 2015 today you know three and a plus years later um you know you're doing I don't know the last I've seen is 50 million revenue probably higher today so we've sold over one million suitcases wow I mean it it's pretty amazing how quickly that's happened but at the same time like you really both you and and Steph came to this with a lot of experience it and experience it really kind of set you up to succeed in in this venture like this was like you you sort of took the time to kind of burn the ropes and I mean now it's in some ways it's not surprising that it succeeded so quickly um I don't know I mean does it does it surprise you I think that um just things have been moving so quickly that like I don't think we stop enough to like to think about what happened and what we've done I think a lot of it has to do with the fact that we're so different and basically like any strength that Steph has is like my weakness and vice versa so that meant like from the beginning we had all bases covered um so I feel like even if this wasn't a runaway success we would have done things like twice as quickly or twice as good as as anyone else um because we really like from the beginning operated as like one brain but I mean I don't know I think it's like I never set out to do this I never set out to to run a company with with hundreds of people and I think what's asked of you when when you have a couple dozen employees and maybe like a couple million revenue is so different than than what is being asked for us now yeah so for us like while externally it it definitely has been successful and really exciting and something we're really proud of we're just like we're constantly like behind the scenes like trying to fix things or trying to try to keep up with things yeah you know like those first those first investor meetings they'll sit there and look at you to see if you have what it takes or if you have the idea that can turn into a one billion dollar company and to us that was so daunting like how do you create a billion dollar company and now the kinds of investors that that we meet with or that we're getting to know for this next phase of the business we'll see things like yeah we really um you know we're really just evaluating to see if this can be like a five or ten billion dollar company which which is mind blowing yeah I mean you're you are like at the time of this recording you're only 32 you've got oh my god like your entire career ahead of you where do you see this company going I mean do you what do you what do you imagine a way becoming um beyond a company that sells suitcases I'm only 31 sorry I'm sorry I'm skinny I was like am I 32 um I mean I so I think for us it's funny because the future away really goes back to what we were saying in those first investor meetings that we're building this travel brand and I think we talked about it a lot but we didn't really know what it meant we knew we were gonna be a travel brand and we were gonna start by selling luggage but we became so obsessed with just every part of the travel experience um so I think you know in the short term like our goal right now is um the way you would go to like to Nike if you're if you're playing sports and you kind of get you can get everything from like one sports wear brand and they make all the different things like we want to do that with travel like when someone's going on a trip we want to make everything they need to go on that trip seamlessly but I think in the long term like what we've done or what we're trying to do is really set this foundation for how do we create a brand that people love and trust enough so that we can solve every single part of the travel experience do you how much do you think of how much you think luck played a part in in your success and how much do you think it was hard work and skill and talent I think it's um it's probably 50/50 I mean I think for me personally luck in timing had so much to do with with everything I've done at every single step just in terms of like the way we time things or the people that we met or even just the fact that like it was really lucky that I called staff when I did and that we didn't take the jobs that we were supposed to but I think um we we worked our tails off especially in that first year just obsessing over everything yeah I mean I don't know I think it's like every time I saw something that excited me I would find a way to do it like I never thought oh I need to get a degree to do that or I need to have certain work experience to do that I would just find a way to do it and I think I'm just a very curious person this is something I learned from my dad actually and um I just followed all of my curiosities that's Jen Rubio of away the company has expanded its product line a bit since those first few bags came off the factory floor in addition to their signature hard shell suitcases and now sell double bags backpacks even packing cubes and the brand continues to gain more and more celebrity fans including most recently gotchas Megan Markle who reportedly gifted away suitcases as party favors at her bar. baby shower. And please do stick around because in just a moment, we're going to hear from you about the things you're building. But first, a quick message from one of our sponsors, Smart Water. Inspired by fresh thinkers whose stories you're listening to, Smart Water has more ways to hydrate. Smart Water alkaline with 9+ pH and smart water antioxidant with added selenium. Smart Water, that's pretty smart. Hey, thanks so much for sticking around because it's time now for how you built that. And today's story comes to us from John Moroni, who lives just outside Grand Rapids in Michigan. Anyway, back in November of 2015, the snows came early to the east side of Lake Michigan. In what afternoon, John decided to take the kids sledding. Sledding is something fun. You can grab a few sleds and go find a hill and spend hours. And as John watched his kids slide down the hill, he thought, "Hey, I want to get in on the action because sledding is awesome." But John is also a fully grown, middle-aged man. And as he sat on that sled, waiting to glide down the hill, he realized that sleds don't always agree with grown-ups. Three pounds and years later on our bodies, sledding isn't quite as exciting as it used to be, you know, when you're 8, 10, 12 years old. Which to John didn't seem fair or right. Sledding should be fun for everyone and besides, this seemed like a problem waiting to be solved. Which worked out great because John happens to be a professor of product design. So that afternoon, he decided to take out his notepad and take some notes. He noticed that a lot of kids like to run and jump onto their sleds trying to get a little bit more speed and a lot of them would do it. Running and then kneeling on their sled as they go down and hitting jumps and things like that. Well, that was terribly uncomfortable for us as adults. That kind of got the wheels turning a little bit. The wheels started turning and John got in touch with a group of friends who also loved to solve design problems. He shared his notes with the team and he asked, "Hey, could we figure out a way to make sledding more comfortable and more fun?" Not just for kids, but for grownups too. One of the team members said to us, "Hey, I think we could really make this a little bit more exciting if we created two independent sleds and strapped them to our legs." Two sleds strapped to your legs. Kind of like the pads a hockey goalie might wear, but instead of pads, they'd be sleds. So John and his buddies decided to pursue this idea. They pulled together about $20,000 each and got to work. The first prototype was actually kind of like a foam-filled sled that was cut in half and duct taped to somebody's legs. Just to see if it were possible to have two independent legs with something underneath them track and stay straight down a hill. It was possible, but not that simple. So for the next model, John made a hard plastic shell to fit over the lower legs. Heard some straps to it and then cut up some yoga mats and stuck those on the inside just to get a little bit of cushion. Yeah, you laughed, but when you're my age, that matters. This version did move better on the snow, but now John needed to make the sleds more comfortable without losing that agility. The foam was kind of the key ingredient to all of this. There's an impact energy absorbing foam that goes into it that sort of raises your feet up in the back and really makes it possible to go down the hill and pick up some speed without totally dragging your feet the whole way. At this point, John needed feedback on his design, so he got his friends, his kids and his neighbors' kids to try them out. You know, we heard really straightforward things like, "I really like how I can run and slide on them. It helps me go faster. I like how I can walk up the hill and not have to carry my sled up." For the next winter 2016, the team was ready to sell their product. They used some of their money for advertising and they ended up selling 800 units. It was time to celebrate, but about two days after that big shipment, we hit this local ski hill. All the founders put on a pair, jumped, went down the hill, and half of them broke. I'm the very first run. Thank God for the beer because that probably made it a little bit more tolerable when we discovered what the problem was, but man, it sure didn't feel good at all. The problem was the straps. They weren't properly attached. So the team grabbed the beer and left the hill and spent an entire night troubleshooting. And after a few days, they sent customers a follow-up shipment. It had better fasteners and instructions on how to attach them. And they also started gearing up for the next winter. They tweaked the sled design and they added a smaller size for little kids. So when the 2017 season rolled around, we sold 8,000 units. We actually sold out. John Maroney and his team are the founders of sled legs. Next year, they're planning to sell sled legs in stores. If you want to find out more about John or hear previous episodes, head to our podcast page. How I built this.npr.org. And of course, if you want to tell us your story, go to build.npr.org. And thanks so much for listening to the show this week. You can subscribe wherever you get your podcasts. And while you're there, please do give us a review. You can also write to us at [email protected]. And if you want to send a tweet, it's at how I built this. Our show is produced this week by Rachel Faulkner with Music Composed by Rumpteen Aero Bluey. Thanks also to Julia Carney, J.C. Howard, Nora Cootsie, Neba Grant, Melissa Gray, Sanna Zmeshkenpur, and Jeff Rogers. Our intern is Candace Lim. I'm Guy Ross and you've been listening to How I Built This. This is NPR.

Podcast Summary

Key Points:

  1. Anthropic was founded on a hard question
  2. Founders often face critical, late-night questions about their ideas—such as whether they should build or quit—rather than surface-level marketing plans.
  3. A small, seemingly ordinary decision—like switching to a business credit card—can drastically impact financial health, with US Bank’s triple cash-back card offering significant rewards for essential expenses.
  4. Travel brands like Delta and mobile fuel services are leveraging AI and customer experience design to create products that enhance daily routines, from fuel cleanliness to travel rewards.
  5. Jen Rubio, inspired by her travel experiences and a lack of appealing luggage, co-founded Away with a focus on user needs, using real customer insights to design a better product.
  6. The launch of Away was delayed due to supply chain realities, leading the founders to pivot with a pre-launch book campaign that generated strong media attention and pre-orders.
  7. The success of Away demonstrated that emotional brand connection—built through storytelling and community—can drive adoption even without a physical product in stock.
  8. Founders thrive when they ask hard questions, embrace iterative details, and trust in their intuition, even when the path ahead is uncertain.

Summary:

The transcript explores how founders and innovators build successful ventures by addressing fundamental, often overlooked questions—like whether an idea is viable, or what small decisions shape long-term outcomes. Anthropic’s foundation on public feedback about AI ethics exemplifies this, showing how deep, honest inquiry drives purpose. Similarly, Jen Rubio and Steph Corey discovered a gap in the luggage market, where travelers lacked stylish, functional, and emotionally resonant products.

Their journey from a personal frustration to launching Away involved rigorous research, early investor engagement, and a bold pivot: creating a coffee table book as a pre-launch product to generate media buzz and pre-orders. This strategy, rooted in storytelling and customer pain points, not only built brand loyalty but also confirmed market demand. Meanwhile, financial and operational decisions—such as switching to a business credit card—highlight how small, intentional choices compound over time.

The narrative underscores that true innovation stems not from grand visions alone, but from patient iteration, emotional connection, and the courage to ask hard questions. From travel to finance to AI, the recurring theme is that success begins with a simple, authentic inquiry.

FAQs

Anthropic was founded on a public-benefit corporation model, driven by the hard question: 'How do we make sure AI goes well for people?'

Anthropic surveyed over 100,000 people to understand their hopes and fears about AI, and they publish the findings—even the uncomfortable ones.

The question is not about the big vision, but about the small, daily decisions that reflect a founder’s commitment to improvement and execution.

Switching to a business card with cash back rewards—like the US Bank triple cash rewards card—can save hundreds of dollars annually by earning back on everyday expenses.

The new Delta Sky Miles Reserve American Express card offers 2 Delta comfort round-trip flights and 15 visits to the Delta Sky Club per year.

Framer allows creators to design visually responsive websites with built-in hosting and CMS, and integrates AI agents to speed up editing and publishing.

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