From Start-Up to the Fastest Growing Cookie Brand (How They Did It) | With Toto Cookies Ep. 23

0:00Today I'm sitting down with the team behind Toto Cookies, one of the fastest growing cookie brands in the natural market. Sydney turned a Crohn's diagnosis and a colon cancer scare into a decade-long quest to recreate the Toll House cookie in a way her body could actually handle. From hand mixing 12 cookies at a time to baking over 400 ,000 cookies a month, she and Bennett have rebuilt this brand through failed iterations, a near disastrous investor saying no to Walmart, and an almost obsessive focus on product over hype. In this conversation, we unpack their genius behind how they scaled, why UGC and founder content only work when the product is incredible, and what it means to build a legacy brand that balances meaning and metrics.

0:37This is Anatomy of a Brand, where every week I talk with people shaping culture, founders, marketers, entrepreneurs, and creatives. And if you're one of those, subscribe to never miss a conversation. This is episode 23 with Toto Cookie co-founders, Sidney Webb and Bennett Quintard. Toto Cookie's been around for four some years. Is that right? About four years. Four years, right. Always as this or different iterations. What are we talking in four years? Has there been changes or has it always been exactly what it is today? There has been many, many iterations. What was the first iteration of Total Cookies?

1:09How did it start there? Let's do a quick little pass over the origin story of it. And then we'll dive into how you guys have scaled this to the fastest growing cookie brand in the natural market. So we'll dive into that. But first, give us a little bit of how this thing started and maybe the first iteration to where we are today. Absolutely. Well, Tota was inspired by my health journey. I was diagnosed with Crohn's disease when I was 16 and went through an eating disorder throughout my high school and young adult years. And my junior year of college, I had a colon cancer scare. And essentially on the other side of all of this, I just wanted something that felt like comfort.

1:55I had been on such specialized diets for such a long period of time and I wanted something that tasted indulgent and tasted nostalgic. And for me, comfort growing up came in the version of Toll House cookies. I just loved the experience of having them fresh out of the oven. I'm a Pillsbury guy, I'm a Pillsbury guy, but I understand the Toll House recession. But a fresh baked cookie, There's just nothing like it. It's true. And when I was, you know, eating gluten-free and redefined sugar-free and all, I was on such a specialized diet. There was nothing that existed that was all of those things that tasted good.

2:32And so I decided that I was going to create my own version of that in my senior year. And you were like, are you like a baker? Are you like, what's the drive here? Just like, I'm going to make this. Is that just kind of like your energy? Like, I'm going to do it. I think I am and have always been a girl on a mission. And I was a girl on a mission that loved sweets. And so I think that that was enough of a driving force for me to figure it out. And I spent about a year recipe testing in my parents' kitchen, having friends over on a regular basis to try my latest creations. And I was trying cookies and brownies and truffles and any sweet thing I could really get my hands on.

3:16And for about a year, every single recipe was just an absolute fail. I really was starting to think that I was crazy for trying. I was not a baker. I didn't have any prior experience. I was really just being a mad scientist in my kitchen. And just as I was thinking that I was out of my mind for trying to figure this out, I decided to try one more cookie iteration. I invited my friends over. my family came over and I remember watching people take their first bite of this cookie and everyone kind of looked at themselves and they looked at me and then there was a lot of oh my gosh where did you buy this this is this is this is not one of your creations and I think in that moment I knew that I might be on to something very cool um and so I didn't initially start a company from that period.

4:14I had a recipe. I had an idea. That was like 10 years ago. So that was way back. This has been in some kind of form of ideation. Which is crazy. It's been a long, long journey. But when I first started selling the product, I was selling individual cookies to coffee shops. All right. I know lots of friends. Here's the thing. I know lots of friends who started that route, but I also don't have many friends. So I have lots of friends who started that route, but I don't have many friends who have gone to the scale that you guys have. So there goes from a moment of like, we're delivering these to coffee shops and natural start.

4:57That feels very real. Like, hey, easy low hanging fruit, sell these to coffee shops. What changed after selling it to coffee shops that it started to change momentum? Like, what was the next step after coffee shops? Go ahead. Man, I mean, just to Sid's credit, in the beginning, this was literally like hand mixing dough with a wooden spoon. No mixer. You have to get your kitchen certified by the county. It might have been. We won't talk about whether or not get all the food certifications yet. Listen, I know so many people. They're like, I don't know if my kitchen's certified doing this, but I'm doing it.

5:29I'm doing it. I don't know if 22-year-old Sid had all of her certifications in line. Yes. But yeah, I mean, it was literally 12 cookies at a time with a wooden spoon. And now we're baking like 400 ,000 cookies a month. So I think like just the transition of that's insane. But it has been many iterations. And it was cookies to coffee shops. Then it was cookie dough that was being sold in like grocery stores. A few things around LA. And then 2022 was kind of this change. late 2022 is this change to like let's get a packaged cookie that's like ready to scale and market let's get a legit co-manufacturing facility that's making it um and let's try to push it to national retail so we basically relaunched the product and the brand in early 2023 same name new name same name just updated branding okay kind of overhauled the team raised some money um and just kind of was this serious moment of like we're gonna go for this we're gonna try to to make this something serious.

6:30Is that because you were like, we're excited about this product or were you actually seeing enough revenue from doing all those things to go, I think we got something and you're more like, and you have all this revenue coming in so it's kind of showing, improving it or were you like, we have enough but we also got a little bit of a gut that's like, this is gonna work. What was your logic? Honestly, the reason, the real reason why we ended up switching to cookies was, and this was like slightly before Bennett and I met, But when we were selling cookie dough during COVID, the refrigerated trucks were so expensive that selling individual shelf-stable cookies was just a more cost-effective way of selling the product.

7:12And then we also realized that once we started selling cookies, people were buying more cookies to enjoy at one period of time than they would buy a pint of cookie dough. So we were selling more product at one period of time than we would be with the cookie dough. And I think it was a really interesting learning because I think it just goes to show that you can't necessarily be married to your first iteration of something. Yeah, don't romanticize this thing because you're going to have to change it. Exactly. Exactly. So in this process, you also kind of, what's unique about Toto's is the visual identity of it is so compelling, right?

7:51You have that part of it, the actual packaging. The taste is also amazing. My sister-in-law, who struggles with a lot of health things and can't have certain foods and different things like that, her kids are in love with the total cookies. When I got that big box of them, it was like I had a massive shopping bag that I brought to them. It was like, hey, here's all the cookies because their kids are just enamored with them, just eating them up. It's one of those things that actually tastes good, so I get that part. But there is also this visual identity, this appeal to it, and that has this striking kind of look and feel.

8:23But also, you guys, there's a part of the UGC, like, content creation, how you guys marketed Total Cookies, that is in line with some of the founder-led stuff online that you see. But you guys have actually scaled it. So how did you think about content, user-generated content, and how you guys positioned this product in that way? What was some of the steps you took with social and all that? And was that your main channel or did you guys do other things? I think that content for us in many ways, like the product has had many iterations. I think the most important part of the content strategy really for Toto has been really making it feel like people are getting to know us and the people behind the brand.

9:12And I think focusing on the product itself has and making sure that it is delicious and indulgent makes the UGC content so easily shareable. shareable because when people are trying the cookie for the first time, I think there's such a, there's such a obsession with the product that they feel a need to share and an excitement to be the first person to tell all of their friends about it. Okay. I think like, that's good. We haven't actually done that much traditional marketing. Okay. Even from a content perspective, I mean, it's been on and off. Like when you guys, are you guys seeding products to people?

9:57Are you doing some of that? Or is it more like people are just actually, we are a bit, we are seeding a bit of product, but honestly it's been mostly organic growth. Okay. And I think there's something to be said for like seeing if the product has the legs to stand on without it being propped up by marketing. Okay. I think it's so easy to just jump in and focus on how do I get ads going? How do I get this out to as many people? How do I just get sales rolling? And I think you can get some inaccurate data if you just focus on the marketing in the beginning. Unpack that. Tell us more. I think you need to know whether the product is a really strong product.

10:36And I think you're not a good gauge of whether your product's a good product. And so seeing whether people will return, will find it, will buy it, will share it with their friends without it being something that has to be marketed to them to do, I think is a really good indicator. And so honestly, I mean, Sid is incredibly magnetic with whatever she does from a content perspective. She's done it on LinkedIn, on TikTok, on Instagram. And so I think there has been that very founder forward aspect to the content. But I don't think we've won because of our marketing strategy. Okay. I would agree completely.

11:10Even if the person who pushed it through that way, I love that. I mean, I think that what we have planned for 2026 is very different from, I think, what we've done in the past. And I think it's because of the obsession of the product and the success that we've had in retail and with people finding it and loving it and it having its own legs to stand on that now we are able to really dive into the marketing. And I think a lot of brands in CPG make the mistake of focusing on the perfect marketing strategy, the perfect photo shoot, the perfect high quality content. And it looks really cool for a while.

11:48You can, you know, make an epic post on LinkedIn or have a really cool Instagram grid. But at the end of the day, what people care about is does this product taste good and would I buy it again? And I think because we've nailed that, it's made so much of the marketing so much easier because we haven't really been doing a ton of it ourselves. It's been people sharing it amongst each other. Wow. Okay. So let me ask you this question. What are you doing? So that's one element. So we got one element of what you guys are doing. that is the product itself is quality and it stands on its own legs and people are finding it in the stores.

12:30They're aware of it from a friend, word of mouth, that kind of stuff. But then also they're finding it on the shelves at Sprouts and other places like that. What else are you doing that you think is leading to this thing, having the success to become that fastest growing cookie in the natural market? Like what, what else are you doing? man i mean i think we're um we're doing a ton behind the scenes to optimize the business to be something that can be scaled okay i think um you know we have a really incredible chief sales officer on the brand and he's worked on a lot of different cpg companies and i think you if you've got a decent product you can get into retailers you can get it sold on d2c but it being something that you actually have the internal capacity to scale is very different.

13:17Talk us through that. Are you talking about, can you actually continue fulfilling orders? Are we talking from the perspective? Yeah, I'm talking about... Because getting a product on the shelf is one thing. Totally. And we've even talked about this, so you shared with me the details of what it's like. Yeah, you can get a product on the shelf, but do people actually... And moving it off. Yeah, moving it off, buying it, restocking it, that kind of thing. Can you keep up... Is that the kind of thing you're talking about? Yeah, I'm talking about having the manufacturing systems in place, having the operational team in place, you know, getting, getting the cash in the business that you need to be able to scale, understanding your cashflow cycle.

13:50There's so much about the like non-glamorous side of a brand and a company that if you don't put those pieces in place, the littlest things can kill you. Not understanding how long it's going to take to collect money from a retailer. Give us a, give us a, a, a failure here. Give us a moment where you're like, man, this sucked because we didn't prepare ourselves in this way. And that, that operational thing maybe kicked you in the back of that? Well, I mean, so there's one pretty insane story. So when we first were, this was probably in 2023, late 2023, we were really trying to focus on the manufacturing of the cookie.

14:28We wanted to get, like, we wanted it to be perfect every time. And with co-manufacturing, you can only control so much of it because another group is basically baking it for you. And so we thought, let's open our own mini bakery. Let's do it ourself. Let's raise some money. And so we spent all this time looking at different locations. I love this. I feel like we're living this thing right now. So we basically started looking in Vegas. We started looking in Arizona. We were looking for like commercial baking space to like do our own mini bakery. And we found an investor. he committed to investing$800 ,000 to do this specifically to get the bakery set up to buy the equipment signs all the paperwork done deal we find the facility in Arizona we move to Arizona we start getting all the permits in place we're talking to the city we've got people coming out for zoning and while our things are still in boxes we realize that this guy is totally full of it and he doesn't have this money and we have one month left of cash flow we're now living in Arizona we've signed a lease to live there luckily we hadn't signed the bakery lease yet but um basically overnight we went from like we've got this money we're scaling we're growing to this guy is kind of a scam artist and had basically committed to us and all these other companies that he was investing and on the back end didn't have the cash to do it.

15:54So yeah. So like it's, it's those moments where there's going to be these things that just almost kill you over and over and over and over again. And I think you need two different people in those scenarios you need. And I think Sid is so good about being the like optimistic, we're going to get through it. It's all good circulated to the network get a lot of people in the in the you know in the ecosystem to start you're not getting you're like i'm not getting drowned by this thing yeah and then you need like kind of me in it to like go through chop through the problems figure out how we can get through it and like operationally get through that phase and then you're looking at both of those as kind of essential ingredients because some people look at them as opposites and they kind of remove one of them they kind of in crisis scenarios and companies you'll find that they'll say the overly optimistic naive people over here and then the other people are like you're so dreadful that you never look for solutions yeah but together there's such a dynamic of you fuel each other in that way where that's where like uh that fun like collaboration that takes place that a lot of people kind of quickly bypass um okay so what so you operations is one thing people overlook when they're trying to grow their cpg brands or any kind of brand they overlook that what are the other things that you guys are doing that you think people are overlooking right now that you guys are like, this is something we're doing regularly.

17:15Is it the sales guy? What are the things that you are breathing for you but are not breathing for others? And you may not be able to even identify them quickly because you're like, this is just the air we breathe. We didn't know it's that different. But for some, it's not even in their mind. I think definitely how you grow in retail is super important. I think the steps that you take as far as what retailers you go to first what accounts are expensive versus what accounts really kind of grow with you there's there's good retailers and there's bad retailers for what's a good retailer what's a bad retailer define that more what does that so I think like a lot of times it's it's fun to think about going into the big retailers that everyone knows the targets the Walmart's they're like all those big ones I've known I just know countless brands who've done that too early and it can kill you it just when you get into a retailer like that and they buy your product.

18:10It sounds great. Yeah. But typically they're going to charge you just to go on the shelf to start, which could be tens of thousands, over a hundred thousand dollars of cash just to get into the store. Okay. Then you sell them the product, but they say, okay, cool. We're going to take the product and we're going to pay you in 90 days. So now you've outlaid all this money to build the product, to get it into the store. And then you're maybe getting paid 180 days after you did that. And then if it doesn't perform, they're going to start deducting money off of your checks for marketing if things start to spoil so I mean we've had moments where we thought we were gonna get early on where we were expecting two hundred thousand dollar checks from distributors because we sold them two hundred thousand over the product and you get your check back and it's got a bunch of lines of deduction for this and promo for this and this spoiled and this misshift and that two hundred thousand dollar check is now twenty six thousand dollars and you're like oh that doesn't even cover my cost to produce so I think that i think that like going like growing in retail with small retailers proving yourself and like growing forward instead of just trying to get that exciting big name that everyone will be like you're super successful yeah um i think like really understanding the ramifications of whatever growth you agree to is huge so what i was gonna say to in in a in a similar vein i think that a lot of people think that the more retailers you're in, the more number of doors that you're in, the more successful you are, or so it is perceived.

19:45And I think that one thing that we've learned is it's always, maybe not always, but in our experience, it has been so much better and more successful for the business to go deep with the people that you've worked with and had success with instead of just casting a wide net and trying to get into as many places as you possibly can. And the reason for that being part of what Bennett was talking about, there's a lot of initiation fees or slotting fees or free fills that a lot of these bigger retailers require. and for example in Sprouts and some of these other retailers where we're a really high-performing product our buyers have taken note of that and they've come to us to say we want anything that you will launch so please let us know when that happens and so I think that we are creating an opportunity for our business to continue to grow in the exact same number of doors and I think that people forget that that's an option because getting into a walmart or a target etc seems like the next right move yeah knowing how to say no to the to the wrong opportunities is huge i mean we've we've said no to walmart we've said no to 7-eleven you know we've said we've had to put pauses on pursuing kind of just mass grocery channels not doing the cvs's and Because it would do, it would.

21:20Yeah, because they're so expensive. They require so much effort and focus and cash. And when we say no, we mean, it's not a no forever. It's just a not right now. And it's the same thing with the ad, like to just to circle it back to like the, the marketing focus in the beginning, it's like, you can just be like, I want to get as many people seeing this product as possible. I want to blow up the ads. I want to do all that. It's the same thing with retail. Just trying to do the, like as many doors we can, whatever retailers were take us but as soon as it starts to like struggle it collapses instead of being like oh we have this foundation we're doing well with natural now let's try going to like home goods or like something else and if you layer these things on instead of trying to just jump too far you limit your risk of just total collapse because once the once the like once the wheel starts to turn the wrong direction from a cash standpoint it can be really hard to like get it going the right way again.

22:21Yeah. So I think growing the right way is. Growing the right way is discerning how, knowing that, finding the wisdom, finding the people to help you even understand that process versus simply thinking you can navigate it on your own. All right. So the wrestle here that I want to ask you guys about is, so Sydney, your chief brand officer, Bennett, your CEO, chief executive officer over here. So I want to know what are the tension points that you guys find? Like what are the moments where you're just like, I want to push for this and I want to push for this that you guys have to navigate to go like, I want to build a meaningful brand.

22:50It may not be all about the numbers or you're like, the numbers, like these things. Like, how do you guys do that dance of both meaning and metrics? Like, how does that work for you guys? Absolutely. I think it's a conversation that we've had a lot more, we've been having a lot more recently because I think, as I mentioned, 2026 is going to be a big, like breakout marketing year for us. And I think sometimes what makes a brand have real staying power and makes it a true legacy brand are things that aren't necessarily quantifiable. It's the being able to build a lifestyle and a cult like following around a brand.

23:32And that's not necessarily always done through like ads that you can measure a CAC on or a specific ROAS on. And so I think finding the balance of, I think that building a brand that has this legacy ability in some ways comes down to like a gut feeling and it can't necessarily be quantified by the numbers. And I think that I feel like I have a strong enough vision for what this brand can become that I feel confident that we can execute on it and that it will make a difference. But I think that sometimes it's hard when you're looking at cash flow and you're looking at how much money we have to allot for a certain amount of time.

24:22It might be harder to be able to justify. I think you need to be able to decide what type of founder you are. Because I think there's a few different types of founders in the world. And I think if you are a Sydney-type founder that is vision and product and brand and big picture, you need to find the person that is going to be thinking about all the details, how you get there, tactically, what needs to happen. And if you're someone like me, you need to find a Sydney. because I always say there's like, you need that person every day who's gonna make two times two equal four, just like every single day, eight times a day.

25:00Yeah, the predictability, you go like, this is what's happening. And you've got that compounding effect, but you need that person who once a month is gonna make two times two equal like 4 ,000, you know? And I think like understanding what type of founder you are and not just trying to be the Steve Jobs or the, you know, the Musk or whatever you wanna do and really thinking about what your skills are and then finding that counterpart, whether it's a co-founder, whether it's just team members, but counterbalancing so you can have those arguments and disagreements because you need to be able to challenge each other on should we focus on brand?

25:33Should we focus on optimization and cash? And if you just have one type of mentality in the room, you're probably going to make mistakes that you wouldn't if you had both. Yeah, you'd be that like, I think there's the concept is called team of rivals. There's this larger book that talks about Abraham Lincoln's individuals he brought around himself who were actually his competitors in running, where he's like, these are the people that are actually competing against me for office. I'm going to bring them in onto my team because this team of rivals is going to sharpen us to a better outcome because we're getting the diversity of opinions and perspectives and balancing it out and letting each other see from different angles.

26:06Ultimately, there's decision-making power that sits somewhere, but everybody's getting to bring their thoughts on this. Okay, a couple more questions I want to ask you guys. If you had to say how you changed over the process of building Toto? How would you describe how you've changed as an individual where you're like, this is as a business owner, as someone's building a brand, trying to scale this thing, all the different entrepreneurial things you guys have done over the years. How have you changed as individuals? What's something you're like, man, this is, I'm different because of this or this is what's different about me.

26:40Good question. You want to go first? I can. Go for it. I think that to Bennett's point in some ways, I've always been an optimist for many reasons that probably don't make sense. From a very young age, I always had a very grand vision for my life and a vision for how I would impact people in the world. And I don't think that I necessarily knew how I was going to make that happen. But in some ways, I think I've always had such a clear vision that that will come true. And I think I've learned that in the process, you can be as much of an optimist as you want, but it really takes so much hard work.

27:34And it takes so many late nights and so many tough conversations. And it really does take such a level of sacrifice. And I think it's really important to have a very clear vision on your why as you are getting started, because there are going to be many, many, many points in time where it feels like. What's the point for continuing on? and I think I've just I've I've changed because I've I've learned to have so much more almost like respect for how hard this really is. Yeah that's good I love that. Yeah man I think as somebody who's been trying to build companies like my entire life you know like I was in high school trying to you know figure out how to start a t-shirt brand and then working on like trying to do a non-profit and then you know dropped out of college building my first like legit company like i've been so focused on trying to find that thing and become this person that i always wanted to be that i think there's this point that's started to tip for me and i think it's it's still in process but stepping out of that mentality of I'm still that underdog who doesn't know what he's doing and it's just scrapping against the world.

29:03Yeah. That view of yourself. Yeah. And just like stepping into like, Oh no, I'm, I'm very capable of this and it doesn't need to be coming from such a place of scarcity and fear. Um, cause I still, I still, sometimes I still feel like I'm that 18 year old kid who doesn't know anything about startups. You're like, you're always walking, you're like, I'm always the youngest in the room. Yeah. I'm always, everybody's looking at me going Like, why are you here? Like, who are you to talk? You kind of live with that because that's how you started. Where you're like, I got to prove myself. And so that energy, if never corrected, stays the whole course and creates that scarcity mindset.

29:37Yeah, it does. And I think people feel it too. And so I think it's just been that moment of like, I've been doing this for 10 years, full time, building my own things. You know? When you say people feel it, what do you mean? I just think people can, I think your team, I think investors, I think people you interact with can feel if it's coming from a place of scarcity and fear and lack or if it's coming from a place of confidence and belief. And I think I've started to see shifts towards that. And I think it's going to be a lifetime longer process for sure. fair. But I think I've noticed the way that people respond to me differently as I start to have more of that belief that this isn't a fluke.

30:22I'm not just, you know, bumbling my way through it, that there might be something here. Yeah. That's, that's really, there's a humble confidence. Okay. I got two more like final questions for you guys. And I'm going to point them at both of you in two different ways. So you can think about them here. Cindy, I want to ask you this question and And then I'm going to, I bet I'm going to share your question at the same time. So you guys can think about this is Sydney, what would you, if you were to be being brought in and someone's like, Hey, I want to start a brand, where does your brain immediately go?

30:51Like, how do you start looking at it? You're like, okay, this is what I think about. And this is what I think you need to think about. So if someone's at that starting phase of a brand, what do you think about? And so as you think about that question, Bennett, I want to ask you, if someone's already started a brand and they're like, what is like, what do I need to avoid? Like, here's where you could go wrong. If you go down this route, this is where it's going to go bad for you. Like, kind of giving some advice and wisdom to go, like, hey, don't do this. That's not just applicable to the CPG space, but all the different spaces that you could think to, the different history you have with building companies, going, you really need to look at this.