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Advice Line with Tara Bosch of SmartSweets

from How I Built This with Guy Raz ·

54m 0s

Advice Line with Tara Bosch of SmartSweets

This episode of How I Built This highlights the critical mindset and decisions that define entrepreneurial success. Founders begin with hard questions—like whether an idea is viable or if they should quit—emphasizing authenticity over marketing plans. The conversation explores how small decisions, such as switching to a rewards business card, can dramatically improve financial outcomes and scalability. Case studies of snack brands Snackish and XO Marshmallow reveal a focus on better-for-you, emotionally satisfying products that bridge health and indulgence, aiming at everyday consumers. Similarly, the experience-based brand Romanticize Collective demonstrates how accessible, joyful micro-experiences can counter digital fatigue and grow through customer feedback. Founders stress the importance of deep customer insights, emotional connections, and long-term vision in guiding product development and growth. Ultimately, success hinges not just on innovation, but on clarity, adaptability, and the courage to act on early ideas—especially when faced with uncertainty. The episode underscores that while tools and strategies exist, the true differentiator remains the founder's ability to persist, learn, and stay true to a compelling vision.

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This episode of How I Built This is presented by Enjin, the modern travel and spend platform built for businesses that are growing. Book faster, save more, and watch your rewards stack up. Stay tuned later in the episode to hear how Enjin is helping thousands of businesses travel smarter. 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 2 a.m. 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 understated. 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. We get support from U.S. Bank. A question I love asking founders. What's the one decision you almost didn't make, the one that changed everything? Because it's never the obvious stuff. It's never, I decided to start a company. It's the small, boring, Tuesday afternoon decision you barely remember making until you realize it's the reason everything after it either worked or didn't. Say you're 18 months in. Business is growing. You've got expenses. You've got to come back. You've got expenses coming from six directions, gas for the van, office supplies, your phone bill, team lunches that are actually client meetings. And you're putting it all on whatever card you grabbed in year one. You're not thinking about it. Why would you? You've got bigger problems. But here's the thing. Path A, you keep going like that. End of the year, you're sorting through statements, trying to figure out what went where. You've left hundreds, maybe thousands on the table and rewards you never earned. You've gone back into the business. Path B, you pause and get the U.S. Bank triple cash rewards Visa business card. Now you're earning 3% cash back on gas and EV charging, office supply stores, cell phone service, and restaurants. You pick up an extra $750 cash back as a bonus. And you've got a low APR on purchases and balance transfers for 12 months while you're scaling. Same business, same expenses. Two completely different outcomes based on one small decision. Visit usbank.com slash business to learn more. The creditor and issuer of this card is U.S. Bank National Association, pursuant to a license from Visa USA, Inc. Some restrictions apply. If you travel often, you'll want to hear about this unprecedented offer. For the first time ever, new Delta SkyMiles Reserve American Express card members get access to the Delta SkyClub, your pre-flight oasis to recharge, with 15 visits and four one-time guest passes each medallion year when flying. Delta SkyMiles Reserve American Express card members get access to the Delta SkyClub, your pre-flight oasis to recharge, with 15 visits and four one-time guest passes each medallion year when flying. I agree. I think the thing that has to coincide with that is taste and that experience of whatever you're enjoying and the emotional connection to it. I mean, chips is what we're starting with, potato chips, but the innovation goes far beyond that to really any salty snack you can think of and want to feel good about enjoying every day. So, yeah. And what's your role in the company? Are you the CEO? Yeah, I started it. I mean, in the same lens of SmartSuite. My daughter, Willa, I think the really special thing is I really built SmartSuite for my grandmother, and now I'm building Snackish with my daughter. So, it was actually, she'll be the first to tell anyone that Snackish was her vision, and SmartSuite was mine. But she comes to retailer meetings, she comes to the snacktory. Your daughter's like a young kid, right? Yeah. Yeah. She's five now. Okay. Got it. All right. But on her way to the C-suite, basically. She's been a big, big driver for the vision behind Snackish. So, is there a consumer in mind right now that you think this is going to particularly appeal to? There's really kind of two groups, and it kind of shows up through what's on shelf today in the category, too. The first is really the better-for-you chip, where perhaps they use avocado oil, but when you enjoy them, they still leave you feeling crummy afterwards. Yeah. And then there's the… functional category with the protein chips where you could eat a big every day but they just don't feel, leave you feeling emotionally connected to the product or taste great. So you don't really feel like reaching for it every day. So Snackish is kind of that bridge of those two kind of groups. So it's just she primarily, she may be, you know, going to her Pilates class, her spins class. She has children, but she still wants to find better choices. She doesn't want to have to hide in the pantry and eat her favorite bag of chips. She wants to enjoy it with her kids. And then there's also the woman who, you know, she may have just graduated college and she's just entering the world and she's a wellness girly, but also loves to go out and have fun and will eat traditional chips too. So we're not targeting an extremist or like a protein maxing demo. We're really targeting kind of your everyday person who just wants to feel good about eating chips. Yeah. I'm curious. You know, you are obviously an experienced operator, right? But when you started Smart Suites, you were a total outsider, right? You knew nothing about the industry. And I wonder how, I mean, this time it's different, right? Because you are experienced and you're coming with resources to do this. So is there less of a, I don't know, an urgency? I mean, is there less of that kind of intensity that you had the first time around? I think it's just as intense and it's just in a different way. I think I don't feel like I'm going to be able to do it. I don't feel like I'm going to be able to do it. I feel that I'm experienced this time around. I think this time around, I have the blessing of having some pre-existing relationships, for example. But I still very much feel like I don't know what I'm doing and I'm waking up every day putting one foot in front of the other. The difference I would say now is I'm very at peace with the unknown and knowing that I will figure it out. All right. Well, we will have, I'm sure, a lot of opportunities to talk about some of the ways you're doing marketing and also your experience with the business. With SmartSuites. Let's bring on our first call. You ready? Amazing. I can't wait. All right. Let's do it. Welcome to The Advice Line. You're on with Tara Bosch, founder of SmartSuites and now Snackish. Please tell us your name, where you're calling from, and a little bit about your business. Hi. Hi, guys. So I'm Lindsay, founder and CEO of XO Marshmallow, a gourmet, better for you marshmallow brand that's reimagining this nostalgic sweet treat. And I'm based in Chicago, Illinois. Great. Welcome to the show, Lindsay. XO Marshmallow. Yes. And I think when I think of marshmallows, like, I'm sorry, I think of, like, the jet-puffed, you know, like, that probably is the 90% of the category, right? Those big plastic bags of marshmallows. I'm assuming that's not how you sell them. Right. So you're describing what I call a bag of boring, and that's not us. So you're used to, like, artificial ingredients, the same flavor, just, like, super processed. So we currently sell our marshmallows in boxes of 12, but you can use our marshmallows the same way you would the bag of boring hot chocolate, s'mores, Rice Krispie treats. But we encourage people just snack on them straight out of the bag. All right. Tell me how this business started. I mean, how did you start this business? Yeah. So I used to have a co-founder, and we started this business together 10 years ago. She was in her last year of law school and looking for an inexpensive gift to give on a law student budget. And at the time, those Pinterest hot cocoa in a jar recipes were very popular, and she found one. And at the end of the recipe, it said, if you're feeling brave, try making marshmallows. Marshmallows. She did. People loved them. She experimented with flavors during her graduation party and promptly told her family, I'm not going to be a lawyer. I'm going to play around with this marshmallow thing. I was on the other side of Chicago going through something very similar. I had started a clothing store while I was an undergrad, and I ended up meeting this girl through social media. We started connecting. I sold her marshmallows at my store for a little bit. We became business partners, and I grew up in East Texas. We went camping, and I had so many wonderful memories of marshmallows. How can we take this incredible memory I experienced growing up and bring it to somebody's pantry every day? You took just a left turn into marshmallows. You now sell marshmallows mainly online, direct-to-consumer. Is that where most of your sales come from? Right now, about 90% of our sales are D2C. Okay, great. Tell me a little bit about your overall sales. What do you expect to generate in, let's say, revenue this year? Yeah, just a little under $5 million. That's pretty great. How are you staffed? How many people do you have working with you right now? I have 11. We self-manufacture. There is no co-man for this style of marshmallow. Wow. You own your own production facility? Yes. I'm in about 10,000 square feet right outside of Chicago right now. All right. You launched about 10 years ago. You're doing about $5 million in revenue a year. Mostly, 90% of your sales are D2C. 90% of your sales are D2C. Before we get into that, what's your question for us? Sure. A little bit of background before we get into the question. We are looking to move into grocery. A big part of this year has been a reformulation. We're pulling all the corn out of the product and moving into that shelf-stable packaging that takes us from four months to 18 months. We have a lot of interest from grocery stores, but creating velocity and moving product off a grocery shelf is fundamentally different. It's much more important than driving D2C sales. How do we leverage the community and cultural relevance that we've spent the last 10 years building to drive grocery sales without cannibalizing our high-margin D2C sales? All right. Now, 90% of your sales are D2C. That's great because your margins are good on the sales, but you want to be in grocery. Tara, you know quite a bit about that, Target and grocery stores and Whole Foods. First of all, thoughts, questions, ideas for Lindsay? Yeah. We live in the same world. Whimsy. Congratulations on your journey. I think it's incredible that you're reaching this fork in the road where you're thinking of, okay, we should really scale. We want to go the path of grocery. Your question on, does it cannibalize one another? We really found that the split was always 70% wholesale, 30% D2C, but grocery really became such an impulse buy where she may not be thinking about it two weeks before she wants to enjoy them to order them. And so having that accessibility when she's in her grocery shop and pulling them off shelf, I see them as living together in unison and serving very different functions versus cannibalizing one or the other, especially at this stage in growth. Yeah. I think that's a really good point. My customer's biggest complaint right now is the cost of shipping and the time it takes to ship something. And to your point, that's because it's so expensive. It's so expensive. It's so expensive. It's so expensive. Because marshmallows and candy are this impulse item. I'm just trying to figure out, I feel like I've got D2C down pretty well. I've done it for 10 years. I'm just like, how do I take that marketing and drive it into grocery? I feel like when it comes to grocery, I'm a 10-year-old startup. It's like I'm in year one, right? Mm-hmm. You know, I wonder, Tara, I mean, we were talking earlier about the jet-puffed marshmallow, right? It dominates, you know, maybe 90, 95% of marshmallow sales in the US. And I don't think there are that many, or certainly not many national marshmallow brands, right? There's the jet-puffed, I think it's Kraft. I don't know who makes it. And then, you know, there's like Peeps, but you eat those on Easter. And there might be, you know, a couple of vegan brands out there. But it seems to me like there's an opportunity to jump out, especially with ingredients. Interesting. You know, all natural ingredients, maybe even something like a prebiotic fiber. I don't know if that's possible. But, you know, something where there's the utility of it, right? And I wonder if maybe there's an opportunity there. Yeah. So we are pushing ourselves a little bit to be what we consider a better-for-you indulgence, right? It's still candy. It's still sweet, but better for you. So we've taken all the artificial colors out of our products. We've taken all the artificial flavors out of our products. And we've taken all the artificial flavors out of our products. And then we're removing corn. So it is going to be a cleaner product, especially compared to the existing offerings. We've talked to our customers about this idea of protein maxing or fiber maxing the product because I consider myself a very customer-focused CEO. And the feedback we've gotten consistently is we don't want to get our protein or fiber from our marshmallows. So it's finding that balance between better-for-you versus healthy. What would you do, like with SmartSweets, a lower sugar version? Sweet enough, right? Because a lot of times, as you know, the sweetness profile in so many confections and foods in the United States is way higher than you find in Europe, for example. And sometimes it just over-indexes. And people don't really need that much sweetness. Yeah. We are looking to find ways to lower the sweetness level of our marshmallows anyway. Part of the positive feedback we often get is I like that this product is a good product. I like that it's a good product. I like that it's not too sweet to begin with. I personally, even for owning a marshmallow company, I tend to like our more savory flavors as opposed to the more popular flavors like birthday cake and cotton candy. So we are trying to find ways to lower the sugar without necessarily becoming a sugar-free brand. That makes sense. I mean, yeah, it's kind of a fun fact, but marshmallows is what I was recipe testing in my kitchen originally alongside gummy bears. And so very familiar with the kind of limited manufacturing that exists in this category and the really unique opportunity you have if you can scale the back end and really become kind of that kind of next generation marshmallow brand. I was having the same thought, I think the sugar, you know, it's if you're having like four to six of your marshmallows today, roughly how much sugar is in them. So if you're having four to six marshmallows, it's about 20 grams of sugar. Yeah, so I think I'm biased, obviously, so take it with a grain of sugar. But I think one of the key insights with Smart Sweets that we identified was creating the permissibility to eating candy every day. In the same way with marshmallows and thinking of that lens of what is that threshold with sugar, that's the tipping point for giving people that permissibility to truly eat marshmallows every single day as a snack. Yeah, that's. It's definitely something to think about. You know, I'm going to throw something out there, and you may hate this idea, or you might like it. I think that you should, you've got your core product, right, which is the snackable marshmallow. What if you offered a SKU that was made with allulose, which is a sugar alternative, which doesn't spike blood sugar. So there are a lot of people, not only diabetics, but people who are, you know, doing low-inflammation diets that are okay with allulose. It's naturally derived. Most people can digest it well, and I think it could work. I think it could work like sugar. Yeah, we are playing around with allulose a little bit. We just hired a special food scientist who actually built out the Peeps factory years ago, so she's very familiar with marshmallows, and experimenting with allulose. I'm a little on the fence about it only because I know some retailers like Whole Foods. I know some retailers like Whole Foods. They don't do allulose, right? They've started to ban it, right? So I think there's an opportunity to have a line that is either sugar-free or made with allulose that isn't part of the core group so that we have both options. There are so many ingredients, too, nowadays, especially for your application. Stevia, monk fruit, different combinations of, like, I know I was using agar-agar, and it worked actually really well in the marshmallow. I was using agar-agar, and it worked actually really well in the marshmallow. In the marshmallows. So, yeah, the paths exist. And it's interesting, too, through that lens of, like, launching mass versus natural channel. I always found that the natural channel was more forgiving from an early-stage startup in terms of giving the end caps, giving the merchandising opportunities, not being as dollar and cents from the beginning, which was really helpful with SmartSweets, because we didn't have the budget to pay what some of the mass retailers would require from the hot. Absolutely. And that's kind of my thought, is roll out in natural and even Midwest locally first. So, we are bootstrapped. We're profitable. We are raising for the first time. But until that happens, we know that we're going to have to scale at a relatively efficient rate. I mean, I think that there's also something with the marshmallow category specifically, where there's so much, like, specific use cases for them, like camping or campfires. So, how do you take that category and then make it every day? And so, I think that snackable element's a key insight. There was a brand called Smashmallow who was really trying to do that. And I think, ultimately, manufacturing held them up. Yeah. That's our biggest concern right now, is the manufacturing side of things. And that is why we're raising, is to be able to build out capacity here. It's challenging. And to your point, there was a company that existed, both had capital. Yeah. And they had capital issues as well as manufacturing issues. I do have their former director of manufacturing now on my advisory board. So, I will say we will be able to jump a little bit of steps, just because I kind of have the plan in place. That's great. Yeah. Worth looking into what happened there and trying to learn from those lessons. Absolutely. Yeah. Awesome. Well, the brand is called XO Marshmallows. Lindsay Shanks from Chicago, Illinois. Thanks for calling in. Good luck. Yeah. Thank you guys so much. Yeah. When you started SmartSuites, there were some brands out there that were doing low sugar stuff, right? But there was an opportunity to stand out. Yeah, absolutely. Yeah, I think the key insight with us, there was no one taking it to that next step of everyday snackability. And for her, I think there's a huge opportunity there. I would eat marshmallows every day. I want to eat marshmallows every day. Yes. Stay with us, because after the break, we'll talk to another founder working to take their business to the next level. That's after the break. I'm Guy Raz, and you're listening to The Advice Line, right here on How I Built This Lab. You're listening to The Advice Line, right here on How I Built This Lab. low sugar candy brand Smart Sweets and the new snack brand Snackish. And we are taking your calls today. So let's bring in our next caller. Let's do it. Hi, guy. Hi, Tara. My name's Vivi. I am the founder and designer of Vivi's Vacation. I'm currently calling out of Hawaii, but I'm usually based in New York and it is a sustainable swimwear label. Welcome to the show, Vivi. So I'm looking your website, Vivi's Vacation, and so bathing suits, swimwear. And tell me about the bathing suits. I mean, are they, yeah, tell me a little bit about the sort of the aesthetic or the thinking behind the brand. So I've been very fortunate to be born and raised in Hawaii and my mom is from Brazil. So swimwear has always been a huge part of my life, in and out of the ocean, growing up surfing. So I began making bikinis by hand in high school for myself, then for friends, gone to college, and then worked as a fashion designer in the industry. So I have a lot of experience around swim. It's a very, the way that they make swim in Hawaii and the quality of Brazilian swimwear fabric is so different than anything that you can find easily in the market within like the main continental United States. So I really focus on high quality swim. Where are you making the swimsuits right now? I used to make everything myself, but recently found a manufacturer and they are made in Brazil, sustainable fabrics and everything. So incredible manufacturer, incredible team there. And you said you started working on this in high school. Yes. And when did you formally launch the business? When did you start selling these? So I guess like the first launch would be my senior year of high school. And then I went to RISD to study apparel design and I would operate like on a seasonal. So I would slowly design through the school year while working on other projects. And then I would launch for a pre-order window. And then I would sew them myself. My mom would help. So sometimes we would listen to how I built this while we were sewing the bikinis, which is great. And then I did that for a few years. And then I kind of paused as I was getting my footing, working as a corporate fashion designer and adjusting to like the life of like going to a nine to five as an adult and all that. And relaunched very recently with actual stock, which has been so different in like mid-July. Wow. Okay. And right now you're selling direct to consumer, I'm assuming, right? This is on your website. And tell me a little bit. So you've relaunched this recently. Tell me how you're doing. I mean, I can't imagine you have a huge marketing budget, right? No. So you're probably still small. Tell me how have sales been in the last, you know, since you launched? Sales have been good. At my peak, I got like 60 orders in the span of two weeks, which was incredible. That was my biggest summer ever. Currently, I've done about, I've sold about 15 sets so far. And launching towards like the end of summer is an ideal. But it's been great because I've been able to get like a first round like of orders out and then having the time to sort of restrategize, like rework the website and aim to hit. Like a second round of orders for holiday season. Yeah. Well, and also, I mean, you know, Thanksgiving, Christmas, lots of people are going to the beach. So, to Hawaii, in fact. All right. Before we dive in further, what's your question? So I've only sold online. And this whole time, it's sort of been like you try to make a TikTok or like an Instagram reel that gets a lot of traction. And it's like, if the algorithm works for you, it works for you. And if it doesn't, it doesn't. And it becomes so crucial that you've really done that edit down. So my official question would be, what was your process or system for editing down to the most important elements of your product, then translating that into packaging, social media posts, email blasts, and website headers? Great question. I want to bring Tara in. Tara, say hello to Vivi's vacation. You, you don't have to answer the question right away. But you, of course, had to figure that out with Smart Suites, you had to figure out what the packaging was going to look like. So first of all, thoughts, ideas, or questions for Vivi? Congratulations on your adventure. It's so inspiring that you had an idea and the courage to act on it when you were in high school. And so inspiring for others that hear your story as well. It sounds like you're really clear on your reason to believe. And that sounds like it's really the fabric and the quality of your work. And I think that's really important. And I think that's really how it's made. And you have such an authentic story behind that. I think if you're thinking across channels, what's so important is, you know, how are you going to communicate that value prop in three seconds or less to the consumer on shelf? When I reflect on Smart Suites journey, and it was actually inspired by a podcast that I had listened to that Tim Ferriss was on when he was talking about how he was marketing his book, The 4-Hour Workweek. And it was the essence of of course, like, you want all women to be wearing your swimwear, but identifying the niche that you are creating the most value for and then infiltrating their world. And with social and TikTok nowadays, you can get so specific in different niches. And there's so many ways that you can really show up in their world from a social perspective and make Vivi seem like it's much bigger by infiltrating the niche. It does make me think to I guess how, how niche is to niche when you're looking for your target audience? And then how do you find that perfect balance of casting that net, but and then also, like meeting the needs of your niche customer? Great question. I mean, I think the blessing that you have is you have customers, right? So you have people who have bought the product, and have resonated with it. And perhaps also people who have bought it again, I always found such great nuggets in picking up the phone, and calling the customers. It's I know, it's, it's so easy these days to just be behind the keyword in the phone. And that works too, and DMing them, but asking people to have a 10 minute conversation. It was incredible, the amount that I learned, and then also the consistent threads that were the emotional connections as to why somebody felt, you know, like, I don't know, I don't know, I don't know, I don't know, I don't know, I don't know, I don't know, I don't know, I don't know, I don't know, I don't know. drawn to the product and why they were repurchasing. And you might find an answer hidden kind of within the thread of similarities of those conversations. That is really, really helpful. Yeah, that's the beauty of Instagram. It's like you can just DM someone and then get have that customer feedback and interaction. It's like the phone doesn't have to have to stop anything, it can connect you. Yeah. connecting the story to the product. And you never know. I mean, And she may, especially with, you know, a brand that's that is coming from Hawaii, where, I mean, that could be one post. It just could go, you know, go viral. Yeah. All right. We're going to take another quick break, but we'll be right back with another caller. Stay with us. I'm Guy Raz and you're listening to The Advice Line right here on How I Built This Lab. Welcome back to The Advice Line right here on How I Built This Lab. I'm Guy Raz and today I'm taking calls with SmartSuite's founder, Tara Bosch. So, Tara, what do you say? Ready for our next call? Let's do it. Hi, Guy. Hi, Tara. Thank you for having me. I'm Allie Aguilar, based in Los Angeles, and I'm the founder of Romanticize Collective. And it's an experience club bringing original, whimsical ways to create, explore, and play into everyday life. Okay. Welcome to the show. Thank you for calling in, Allie. So, I don't understand what the product is. Explain that to me. I get the whimsical joy. What do you sell? What do you make? Yes. So, right now, it's in the format of a subscription box. So, instead of products, I deliver experiences. So, you get an experience guide and then intentional items to bring the experience to life. And right now, there are four that are delivered every month to our members. Okay. So, it's a box. And what's inside? So, the idea is rooted in getting you out of autopilot and bringing a little more magic into an average Tuesday. So, it could be anything from making homemade cavatelli pasta from scratch. Another could send you out into your town where you're exploring like a tourist again. Or have you looking up at the night sky under a meteor shower. Okay. So, it's like it gives you prompts. But also, it gives you like the ingredients to make pasta? So, for that one, it would be the guide would kind of give you a backstory on cavatelli and where it originated from. And then I'll put together playlists to kind of set the Italian vibes. It'll have a tutorial or recipe. And then the items are a wooden pasta block and the roller. So, you would go out and get the flour. But that's kind of getting you to actually do the experience. All right. So, it's a subscription box. And that's the revenue model as a subscription. Right. Currently, yeah. And so, tell me how this idea came about. Yeah. So, my background is in real estate and development. And I've done that for high-growth tech startups. And in those environments, you know, it's always about the next milestone, the next launch, go, go, go. And I realized I'd gotten really good at prioritizing that and kind of deprioritizing the things that light me up. So, things that made me curious or got me to create or explore. Or just simply play again. And I was like, how can I make this more accessible to weave into my life? And so, I kind of came up with a subscription model where it was delivered to your door. It was guided for you, already curated. And you could easily do it on like a Tuesday evening. And so, you started this business. And I'm sorry, when did you start it? I launched in January of this year. Okay. And how is it doing? Give me a sense of your numbers. Yeah. Right now, we have 30 recurring members. So, done just under 20,000 in total sales. And right now, trying to figure out a sustainable customer acquisition. Yeah. All right. So, before we dive in further, tell us what your question is. Yeah. So, kind of relates back to the subscription model. So, I'm curious how you know when to keep refining how you market and grow what you've built. So, in this case, the subscription model versus when it's time to evolve the product. So, I'm curious how you know when it's time to evolve the product or the business model to better deliver on the mission. Okay. Tara, I want to bring you in. What's the sign that you look for when maybe you should try something else out or maybe sunset something or double down on something? Yeah. You're creating joy. You're creating moments of joy and experiences around that, and the world always needs more of that, so that's awesome. How do you determine what experiences you're including in the boxes? I mean, I think that's a really broad spectrum of, you know, someone going stargazing or someone cooking, and how do you decide kind of the, like, threshold that it's an experience that all your subscribers will like each month? Yeah. Right now, I'm constantly iterating on that. So, it's four unique experiences that I design every month. So, I'll either root it in things that are happening that month. So, the stargazing was around the massive meteor shower we had. So, I'll kind of think, okay. Is there a season or a major event or a whimsical holiday that I can craft something around, but they're all intentionally, one is always getting you to create, one is exploration, reflection, and then another could just be, like, a whimsical way of doing something simple, and those are kind of, like, the core themes I try and diversify in each one, but eventually, like, any subscription model eventually is meant to be customizable to your desires and what you want to bring into your life. That makes sense. Sounds like you're in that kind of early validation of the, like, product market fit and, like, and what is that sweet spot. Have you talked to your current 30 customers to understand what's keeping them coming back? Some of them, but I definitely, I wrote that down. I know you mentioned that, I'm doing those calls. I think that would be a good way to just get more of the feedback around the emotions and what people are liking and not liking. Yeah, definitely. I think the overall thesis of what you're trying to do is smart, and there are a lot of opportunities around this, you know, this sort of analog or tactile experiences, a lot of in-person experiences. I think it's going to be a bigger business as more and more things just become AI and, you know, people can't tell the difference between what's real and what's not. And so I see the kernel of something here, and this is, like, version 1.0, right? This. And it may be that you continue to do boxes, but they are something different, or it may evolve into, you know, into something that you aren't even, can't even imagine now. Like meetups or, you know, or sort of groups around the country or a network or some community building thing, right, that is, that serves the purpose of this idea that we need to have these tactile, these real-world, offline experiences. So I would give it a, you know, I think to Tara's point, I would talk to your customers and get as much information as you can, as much data as you can. And I would continue to experiment with that while thinking about the bigger idea, right, which is to get people connected in a different way. Yeah, one question that's coming up for me, too, that's, like, when you chat with them, figuring out, are they opening the box? Doing this experience, and then are they telling their friends and family, and are their friends and family subscribing? And if they're not, why? What's holding them back? I think of, like, Fresh Prep or, like, that kind of where it's like, oh, my gosh, I made a dinner right away. It comes up in friend conversation. You're like, this saved me so much time. The ingredients were in the box. And then your girlfriend's signed up with her family the next day. So if people aren't kind of having that natural waterfall effect. What's stopping them? And I think that could be a really good nugget to understand how to evolve from a product perspective as well. Yeah. No, that's really good feedback. Thank you both. I think the overall vision is, like, this is how it exists today, but essentially trying to make experiences as accessible as buying a consumer product. It's, like, the same way we can have something delivered to our door and consume it, and it's done. You could also, you know, learn how to do a new thing or experience a world. Somewhere far away. I'd be curious, like, given that it's experiences, kind of micro experiences delivered to you, is there another format that you guys envision for this model? I would. I mean, you're in Los Angeles, right? I would think about testing out some kind of in-person thing, right? I mean, I think that could be a huge value proposition, right? You're here. You're here. You're here. You're here. You buy the box, and there's an opportunity to actually meet up with a few other people and maybe, like you say, experience your own city. It's worth experimenting because I also think, aside from offline, you know, people want to – you're seeing people buy books, right, instead of reading them on screens. People want to be around other people, right? So it's not easy, but it might be worth trying to experiment with. So it's not easy, but it might be worth trying to experiment with something in the box and a real-world experience. If you have some people in the L.A. area, for example, that you can experiment with. Yeah. I am doing an event – it's funny that you say that. I am testing that at the end of the month, doing a collaboration with a local women's group, so bringing one of the experiences from the box to real life. So it's kind of like a scavenger hunt in Culver City, and then you're gathering items and then doing, like, a junk journaling experience. So – It'd be interesting to test that. Yeah. There's a couple of companies, too, I think that are operating at scale. I can't think of one of the names, but where they they plan the trips that you can purchase the road trip, you know, and or the itinerary. And they're very experience based, too. And it could be interesting to connect with some of those founders and even from like a cross collaboration opportunity and things like that from a brand awareness perspective. OK, thank you. Yeah, well, it's an awesome idea. I would keep experimenting. Ali Aguilar, the brand is called Romanticize Collective. Good luck. Tara, thank you so much for doing this. It's so great to have founders come on and, you know, and give advice. It's one of the great advantages we have on the show, which is we can bring all these founders who've been on and have them come back and help us out. I feel so honored, honestly, and so inspired by the entrepreneurs that came on today and shared their stories, too. It's yeah, it's it's really cool. The world needs. It's more people having the courage to act on ideas than ever before. I agree. Tara, before I let you go, just one question for you, which is if you could go back to when you started Smart Suites and, you know, in the in in the basement, like mixing, mixing up the ingredients. If you could go back and say, hey, here's something you need to know as you're starting out. What do you think would have been helpful for you to know? I think the clarity of what the world looks like. Five years from now with your vision in it and being so crystal clear in that there is a quote and I can't remember who it is by, but it's always resonated. And it was the essence of it's not that you can't get to where you want to go. It's that most people don't know where they want to go. So clearly defining like what is that point? I would have defined that even with more clarity from the beginning. And once I did, I saw how that catapulted. The vision forward. That's pretty abstract. I know, but it dovetailed into all of the specific decisions like retailers launching nationally or not and things like that. Yeah, it's great advice. Tara, thanks again. And by the way, if you haven't heard Tara's original, I built this episode. You've got to go check it out. Here is one of my favorite moments from my interview with Tara. We put a launch date for December of 2015. Come second week into December, they call me and they say, hey, we are not going to let you use this recipe, this formula. You can use another formula with chicory root fiber as the bulking agent. And immediately I knew what they were telling me was we're going to give you a recipe that's actually not digestible. That's going to blow up people's stomachs. That manufacturer took the recipe and ended up going on to launch a product. They're going to protect themselves. Hey, thanks so much for listening to the show this week. And by the way, please make sure to check out my newsletter. You can sign up for it for free at GuyRoz.com or on Substack. This episode was produced by Chris Messini with music composed by Ramtin Arablui. It was edited by John Isabella. Our audio engineer was Anli Huang. Our production staff also includes Alex Chung, Carla Esteves, JC Howard, Catherine Seifer, Casey Herman, Carrie Thompson, Sam Paulson, Neva Grant. And Elaine Coates. I'm Guy Roz, and you've been listening to How I Built This. Thanks again to Enjin for their support. If your business is growing and your team is traveling, Enjin makes it simple and saves you money doing it. 33,000 businesses have joined. Now it's your turn. Enjin.com. slash built

Podcast Summary

Key Points:

  1. Founders face hard questions early, like whether their idea is viable or if they should quit, and Anthropic built on such a question by focusing on AI’s positive impact on people.
  2. A key challenge in entrepreneurship is distinguishing between those who build and those who only dream—AI tools like Claude may help by enabling idea generation, but execution still depends on personal drive and decision-making.
  3. Small, overlooked decisions—like switching to a rewards card—can drastically impact business finances and scalability, as seen with U.S. Bank’s triple cash-back Visa card.
  4. Snackish and XO Marshmallow both target everyday consumers seeking better-for-you, emotionally satisfying snacks, bridging the gap between health-focused and indulgent food.
  5. Successful founders leverage customer feedback and emotional connections to refine products and marketing, especially when transitioning into new channels like grocery stores.
  6. The journey from product idea to market success often involves pivoting based on real-world insights, such as learning from failed manufacturing models or customer behavior.
  7. Subscription-based experiences, like Romanticize Collective, offer accessible, joyful micro-experiences that counter digital fatigue, with potential to evolve into real-world community events.
  8. Clear vision and long-term direction—knowing where you want to go five years from now—serve as a guiding force for decision-making and business growth.

Summary:

This episode of How I Built This highlights the critical mindset and decisions that define entrepreneurial success. Founders begin with hard questions—like whether an idea is viable or if they should quit—emphasizing authenticity over marketing plans. The conversation explores how small decisions, such as switching to a rewards business card, can dramatically improve financial outcomes and scalability.

Case studies of snack brands Snackish and XO Marshmallow reveal a focus on better-for-you, emotionally satisfying products that bridge health and indulgence, aiming at everyday consumers. Similarly, the experience-based brand Romanticize Collective demonstrates how accessible, joyful micro-experiences can counter digital fatigue and grow through customer feedback. Founders stress the importance of deep customer insights, emotional connections, and long-term vision in guiding product development and growth.

Ultimately, success hinges not just on innovation, but on clarity, adaptability, and the courage to act on early ideas—especially when faced with uncertainty. The episode underscores that while tools and strategies exist, the true differentiator remains the founder's ability to persist, learn, and stay true to a compelling vision.

FAQs

Enjin is a travel and spend platform designed for businesses that are growing. It helps users book faster, save more, and accumulate rewards through smarter travel and spending decisions.

Anthropic was founded on a hard question: how can AI benefit people? They conducted surveys with over 100,000 people to understand public hopes and fears about AI, and publish their findings transparently.

Snackish bridges the gap between 'better-for-you' and functional snacks by offering tasty, healthier chips that don’t leave people feeling crummy, with a focus on emotional satisfaction and daily enjoyment.

XO Marshmallow uses all-natural ingredients, removes artificial colors and flavors, and avoids corn. It emphasizes better-for-you consumption while maintaining a nostalgic, snackable experience.

The U.S. Bank triple cash rewards Visa card earns 3% cash back on gas, office supplies, phone service, and restaurants, helping businesses save hundreds of dollars annually and reduce expenses without changing operations.

Grocery sales are impulse-driven and require different marketing strategies than D2C. The risk of cannibalizing high-margin D2C sales requires leveraging existing community and cultural relevance to drive grocery adoption without conflict.

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