How College Sophomores Turned $20, a Cellphone and a Dream Into a Cookie Company with Tiffany and Leon Chen: An EOFire Classic from 2022

10 Oct 2025 · 27 min

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Entrepreneurs on Fire - Episode Summary

Podcast Information

  • Podcast Title: Entrepreneurs on Fire
  • Host: John Lee Dumas
  • Guest: Tiffany and Leon Chen
  • Episode Title: How College Sophomores Turned $20, a Cellphone and a Dream Into a Cookie Company with Tiffany and Leon Chen
  • Original Release Date: 2022

Episode Overview This episode revisits the founding story and growth of Tiff's Treats, a cookie delivery company started by Tiffany and Leon Chen. The journey began with a mishap on a date that led to the innovative idea of warm cookie deliveries, ultimately evolving into a multi-million dollar business.

Key Highlights

Founding Story

  • Inciting Incident: Tiffany stood up Leon for a date and baked cookies as an apology.
  • Business Idea: Inspired by the cookies, Leon envisioned a delivery service for warm cookies, similar to pizza delivery.
  • Initial Resistance: Tiffany was hesitant at first, but Leon convinced her to pursue the idea.

Growth and Development

  • Technology Use:
  • Recognizing the lack of existing delivery software, they decided to build their own custom software to facilitate their business model.
  • Initially faced challenges with unreliable software developers but eventually built a robust system that still operates today.
  • Funding Strategy:
  • They emphasized the importance of building a solid foundation before seeking investment, leading to a successful fundraising round in 2008 after achieving proof of concept and revenue.

Core Values of Tiff's Treats

The company operates based on five guiding principles

  1. Make People Happy: Focus on creating warm moments and connections through their product.
  2. Make It Right: Commit to customer satisfaction and rectify any issues promptly.
  3. Protect the Brand: Strive for excellence in the niche of on-demand warm cookie delivery.
  4. Be Passionate: Foster a passionate team dedicated to a unique business model.
  5. Adapt and Grow: Embrace change and leverage technology for continuous improvement.

Community and Charity

  • Charitable Initiatives: Tiff's Treats donates 100% of sales from the opening of new locations to local charities, fostering a strong community connection.

Book Mention

  • Tiffany and Leon co-authored a book titled "It's Not Just Cookies," where they share their entrepreneurial journey, struggles, and insights for aspiring business owners, along with cookie recipes.

Key Takeaways

  • Success Begins with Building: Entrepreneurs should focus on developing their business and infrastructure before seeking outside funding for the best chance of success.
  • Confidence is Key: For those starting or growing a business, self-belief is crucial, despite the inherent challenges and fears.
  • Diverse Paths: There is no singular way to achieve business success; each entrepreneur must find their unique route guided by their values.

Call to Action

  • Visit [Tiff's Treats Cookie Delivery Website](https://www.cookiedelivery.com) for more information and to experience their offerings.
  • Check out their book for insights and recipes at [cookiedelivery.com/fire](https://www.cookiedelivery.com/fire) for a 20% discount.

Sponsors

  • HighLevel: An all-in-one platform for entrepreneurs and marketers.
  • Gelt: A tax planning partner providing personalized consultation.

Conclusion The episode not only recounts an inspiring entrepreneurial tale but also emphasizes the importance of foundational values in business, the integration of technology, and community engagement. Tiffany and Leon's journey serves as a motivational blueprint for aspiring entrepreneurs.

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Transcript

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0:01Boom! Shake the room, Fire Nation. JLD here and welcome to Entrepreneurs on Fire. brought to you by High Level, the all-in-one sales and marketing platform. On today's classic episode, we'll be breaking down how college sophomores turned$20, a cell phone in a dream, into a cookie company. To drop these value bombs, I brought Tiffany and Leon Chen into EO Fire Studios. In 1999, Tiffany accidentally stood up Leo Chen for a date. As an apology, she baked and delivered a batch of warm cookies, and the concept of warm cookie delivery was born. And today, we'll talk about how you have more chances to succeed if you build and focus on growing your company first before raising money.

0:40And there is no one way to get it done. We talk that through and oh, so much more. And a big thank you for sponsoring today's episode goes to Leon Chen and our sponsors. Are you ready for the ultimate all-in-one platform for entrepreneurs, marketers, coaches, and agencies? Build funnels, automate follow-ups, manage clients, and even white label your own software, say hello to our featured partner, High Level, and visit highlevelfire.com to start your free trial today. Fire Nation, it's time to stop guessing and start winning with a proven playbook. Inside the Freedom Circle, you'll have access to my step-by-step systems for creating offers, building processes, and driving traffic, all in just 90 days.

1:27Ready for freedom? Visit freedom-circle.com to learn more. Tiffany, Leon, say what's up to Fire Nation. How are you guys doing today? Hi, we're great. Thanks for having us. Well, we are excited to have you. I'm already smelling the aromas of an amazing interview here today. We're going to start with you, Leon, because I do want to know, So how the heck did a college apartment cookie delivery service turn into a$500 million in growing business? Tell us that story. I often wonder myself how. And I will say it all started, and this is where I will defer to TIFF, because it all started when my now wonderful wife, but back then she was not my wife.

2:17We were only 19 years old. She stood me up on a date. So is this where I'm taking over? I have to defend myself, I feel like. But there's not a lot more to say about that. It is true. We were dating, but I stood him up on a date. And as an apology, I baked cookies for him. That was something I did personally as a hobby. I was somewhat known for it. And so I baked him a set of cookies, drove them over to his house to say, I'm sorry. And he took one bite of the cookie and immediately thought that we should do this as a business. Warm cookie delivery right from the oven delivered to you just like pizza delivery.

2:54And he called me up and said, we've got to do this. I immediately said no. I didn't want to do it. But he talked me into it. And we ended up getting started right out of his college apartment just two weeks later. and here we are 23 years later, still doing it, but on a larger scale. Yeah, I'd say on a slightly larger scale for sure, but I love when we get to hear how those aha moments actually happen. I mean, when Leon bit into that cookie, he was like, wow, I just literally got delivered to my door, these warm cookies. Why could I not have this on a more frequent basis or on an as needed basis or as desired basis, just like pizza is?

3:35And, you know, let's be honest, 23 years ago, that's actually when I was in college. I mean, there really wasn't a ton of delivery that was out there. I mean, you could get pizza delivered, but it wasn't like there was Uber Eats and DoorDash and all these different things. So it was a pretty interesting idea at the time. And you were able to develop this, Tiffany, into a technology driven consumer brand. So now, as we sit here today, Tiff's Treats, they are this technology-driven consumer brand. How did you transition into this over the years? Well, that was really a product of solving a problem that we had, which was, like you said, this was not commonplace to run delivery services back in the late 90s, early 2000s.

4:21You had pizza and you had Chinese food delivery, but not a ton else. So when we went to go start professionalizing our order taking system, everything off the shelf just wasn't fitting for us. We were on demand. We weren't pizza. We also did gifting. You could also schedule your order in advance. And there was no software out there that would handle all of these different functions. So we said we were going to build it ourselves. So we hired software engineers to build us custom software. It took a while to get that off the ground. We actually went through probably three different partnerships.

4:55before finally landing on one that worked. And in 2005, we launched our own software, which was at the time really just to take in orders. But since then, we've continued to add to it and add to it. It really is a platform that runs our business, both customer-facing and back-of-house. And we use the same system today, 20 years later, but it just has a lot more bells and whistles. Leon, obviously there were a lot of struggles building that software, building what you needed to be a technology-focused brand. What was one of the biggest, if not the biggest struggles you faced in that endeavor? There was probably a hundred different times where we were wondering what the heck we were doing with this business.

5:41But when it came for the technology, the biggest struggles were really right at the beginning. We kept hiring software developers that ghosted us. Back then, we didn't call it ghosting. We just didn't know what happened. They said that they would do X, Y, and Z, and then they wouldn't return our calls. We went through probably three different people before settling on, settling is probably not the right word, but we got connected through who is now our current chief technology officer. She was building this on the side of her day job working as a consultant for one of the big five consulting firms.

6:16Wow. I mean, Fire Nation, things have really changed over the past 10, 15, 20, 23 years. And this is just one area where back in the day, it wasn't easy holding people accountable. It just wasn't. There was a lot of trust that had to be put forward. And a lot of times that trust just was not honored. And let's stay with you right here, Leon, because raising money is terrifying for most entrepreneurs. I mean, Fire Nation, my listeners, they'd love hypothetically to raise money for their business, but they don't even know where to start. Yet you've raised hundreds of millions of dollars from investors.

6:50What is your secret for my listeners here today? For us, we got very fortunate because we started in 1999. We did not go out and raise our first round of funding until 2008. So we had not only proof of concept, but we had real revenues. We had a brand that was already built. We had already started on our technology. And so I think sometimes entrepreneurs are really excited and they want to go do that fundraise. But building and taking your time to focus on building your company and building your structure, your infrastructure first before you go out there to raise money will give you the best chance at success.

7:30Fire Nation, we have a lot of things we're going to be talking about. TIFF's top five, the core values that guide their company. We're going to talk about the technology, charity, and warm moments that are the three cornerstones of Tiff's treats, and so much more when we get back from thanking our sponsors. Fire Nation, tax season might feel far off, but here's the truth. The real planning happens now. Waiting until April usually means you're just reacting instead of taking control. When's the last time your CPA actually checked in to make sure you're set up for success before tax season? That's why I'm fired up about Gelt, your year-round tax partner for entrepreneurs, business owners, investors, and high net worth individuals, Gelt pairs an elite team of CPAs with powerful tech to create strategies that work all year long, not just once.

8:19You'll get proactive planning for both business and personal finances, a clear roadmap that tracks your goals, and seamless tools to file and review, all backed by a team that actually knows your situation. Fire Nation, I used to scramble every April and hope for the best. Now I see how much smoother things can be with a partner who helps me think ahead, get a personalized consultation, and 10 % off your first year when you mention entrepreneurs on fire. Visit joingelt.com slash E-O-F. That's www.joingelt.com slash E-O-F. Okay, let's talk about a platform that's completely changing how entrepreneurs are running their business, and they are also our featured partner high level.

9:04If you're an entrepreneur, coach, agency, or course creator looking to grow faster and smarter. High Level is the all-in-one platform that replaces your entire tech stack. Seriously, think ClickFunnels, Calendly, MailChimp, Kajabi, and even your CRM all rolled up into one powerful white label solution. You can build funnels, send SMS and email campaigns, schedule appointments, manage pipelines, run memberships, and even launch your own branded mobile app. It's drag and drop simple, incredibly customizable, and built for serious growth. My favorite part, You can resell HighLevel under your own brand.

9:37That means recurring revenue, loyal clients, and total control. So whether you're tired of duct taping tools together or ready to start offering high value services with ease, HighLevel is your unfair advantage. On top of it all, their support team is second to none and has your back every step of the way. Seriously, every question that pops up, they will have your answer waiting. And if you visit my special partnership link, you'll get a free trial. So visit highlevelfire.com to start your free trial and see why thousands of businesses are switching. That's highlevelfire.com, where marketing, sales, and automation finally come together.

10:14High Level, join the revolution. Tiffany, we're back, and I want to start with you here because this is, after all, TIFF's top five. What are the core values that guide your company? Thanks for asking. And first of all, TIFFS now refers to TIFFS as in TIFFS treats as the whole company. So I can't just claim these to be my top five, but they are the top five values for our company, which we call TIFFS top five. And we came up with them. Oh, at this point, it's been about 10 years ago. So they were not something that we started out with. We did not open a business and say, what are our values? And then going from there, we did it totally the opposite.

10:55We opened up a business. We thought we were creating a service that people wanted. And then over the years, we started getting feedback from customers. And that's how we formulated, okay, what is it that we're doing here that is making us special to people? We are connecting with people here. And what is it? And so we came up with this list of top five. The first one is we make people happy. So if nothing else, our job today is to make you happy with a warm cookie delivery. And it's It's really a little bit more than just making people happy. It's making these warm moments of connection between people, people sharing a warm, physically warm product, a warm, nostalgic, comforting chocolate chip cookie together.

11:39We've learned is really impactful in people's lives. They can send them to each other and have this giftable connection moment, or they can order them together. Maybe it's an office around the table. Everybody's getting together and sharing this, but it is this moment that people are having. And that's really where we started talking about warm cookie moments that people are having. And that is our top, top value that we always want to keep in mind. The next is we make it right. We all know things can go wrong. Sometimes it's on our end and sometimes it's on the customer's end. But when you're having a delivery made, there's many chances for a little something to go wrong.

12:16But we're always going to make that right. Even if you give us the wrong address and you call back and say, where did my cookies end up? We will say, you know what? You said sweet 300, but is it really 200? We will remake that and send that back out for you for free. And the reason we do that is you are expecting a certain something, a certain experience when you ordered. And if you didn't get that experience for whatever reason, it is our job to bring you back to what you are expecting to get, not with a refund, but with a redo of the experience. And then we protect the brand. That's number three.

12:52We like to keep things simple here. Our aim is to be best in the world at what we do. And we like to think that we are best in the world at on-demand bake-to-order warm cookie delivery and on-demand gifting. And every decision we've made since the beginning has been in service of that. And every decision that we say no to is because we don't want to take away from being best in the world at warm cookie delivery. We are passionate. That's number four. We're a group of very, very passionate people. We're out here to do something that's never been done before, to build a brand that didn't exist and really to build an industry that didn't exist when we started.

13:29So we're all very passionately aligned around that. And finally, number five is we adapt and grow. When we started, it was 1999. And we really needed two things in order to do a two-person business, a delivery business. And that was cell phones and the Internet. They were both becoming newly available to everyone. And we realized right up front that technology would help us grow and scale our business. And we leaned into it. As we said before, we built our own technology. We're constantly updating that, upgrading it. We're constantly upgrading our operations. We're adapting equipment to fit our needs.

14:08Since warm cookie delivery is not a large industry the way that we operate, we have to adapt our own equipment to it. And the reason we have this as one of our values is we found that one thing about people in general is that change makes us uncomfortable. And if you're hoping to come to work here on day one and leave on your last day and largely do the same thing throughout, this probably isn't the place for you because we're always adapting. We're always growing. We're changing to make things better, more streamlined, a better experience for the customer. So hopefully that's something that's exciting for people on our team.

14:42And if it's something they just can't stand, then this probably is not the place for them. Fire Nation, I really hope you're just understanding what makes Tiff's Treats just so special. I mean, they're really caring about the customer experience first and foremost, which is so meaningful for so many reasons. Is there anything you want to add to this, Tiffany, before we move on? About the customer experience, you're absolutely right. You hit it right there, nail on the head. That is what's so important to us. People entrust us with their special moments. And it's important to us from the time that they place the order to the time that they receive the order, that everything was an awesome experience for them, that the customer service along the way was top notch.

15:24And we take a lot of care and a lot of pride to make sure that we own that experience the whole way. Special moments, special experiences. And Leon, technology, charity, and warm moments, those are the cornerstones of the Tiff's Treats brand. Tell us more. Warm moments we can go on and on about. In fact, in the book that's coming out on April 5th, we included some of our favorite warm moments over the years. And like Tiff said, we realized early on people were ordering cookies but as a way to connect with one another, as a way to comfort one another. I'll go real quick into one of my favorite war moments of all time.

16:05It was early on when a woman from a downtown office called one of our managers to place an order. The manager gets talking to the woman, and the manager says, hey, what are you ordering for today? And the woman who was working at the downtown office, she said, well, I'm an admin for this office, and our boss here, whenever it rained, he would always tell us stories about how his mom would make him cookies. when he was a little kid, every time it rained at school. So when he came home from school and it was raining, he knew he was going to have fresh baked cookies. So every time it rained, it would remind him of his mother.

16:40And the lady goes on to say, today is the first day it's rained since his mother passed away. And so everyone here at the office decided to get together and order some cookies so he could have fresh baked cookies during this rainy day. I mean, Fire Nation, those are the type of experiences that you are creating for your customers, for your clients, for people who are connected to you and your brand. So this is just really powerful stuff. Now, we also wanted to bring in the technology and charity aspect of this as well. So would either one of you like to jump in on that? Yeah, I'll jump right in.

17:15So with the charity has always been a very big deal for our brand. It started with the opening of our second location all the way back in 2006 and 2008, our second and third locations, where for every opening, we give 100 % of the sales, not the profits, but the sales from that day to a local charity that is near and dear to our heart that is in the communities that we're opening the stores in. And we've done this for every single store since our second one. And it's really, really fun. It's a great day. The community comes out to support. We've done Make-A-Wish before where we've even invited the Wish Kid out and they've served cookies or baked cookies.

17:59We've gotten a limo to pick up the kid, the Wish Kid and the family. And it's just something that we want to do. This is something that we want to stand for is that we want to give back in the communities that have received us over the years. Now, let's talk about the technology aspect. I mean, We got into a little bit about that before the break and how you really are a technology-driven consumer brand at this point. But what else do you want to add here, Leon? Yes, it's very easy to think that, oh, Tiff's Treats, they have over 75 locations. They're more like a retail or a restaurant or a multi-unit concept.

18:36But almost all of our orders come in online or through the app. So in truth, we are very much an e-commerce brand. And even very, very early on, I remember the year that we did$40 million in revenue, we spent$4 million on software development on our technology. We were spending 10 % of our sales to build our technology. And we know that, again, it's based on the fact that we want the customer experience to be seamless. And we know that these days, technology is the answer to that. Now, Tiffany, you have been killing it in business for a long time now. And as a couple, you guys have been thriving in business too.

19:21I mean, I'm sure there's some ups and some downs. I mean, I've been working with my significant other now for 10 years, so I totally get all of that. But it's not just cookies. It was your actual first time writing a book together. How was that process for the two of you? Great question. And I think the process of writing the book was the same as the process when we do anything, which is Leanne has an idea, he gets it started, he gets the ball rolling, then I come in. She says no at first. Yeah, I say no, and then we figure out how to make it work, and then we get really excited, and we work very, very well together, but sometimes it takes us a little bit of greasing the wheel, like getting it rolling.

20:08At first, we struggled a little bit on how to write a book together because, you know, we're like sitting side by side, who's going to type and who's going to do this? And then we're like, how do two people write one thought? And I think it was Leon's idea to say, let's write it in different voices. I'll say my part and then you say your part. And then we kind of go back and forth, sometimes on the same different, you know, takes on the same thing. And once we figured that out, then it was really, really easy because it was like being, working on a project together, but still having separation enough to where I could write my own thing, he could write his own thing, and then we would come together and see how it all fit.

20:52So it ended up being a really, really fun process, but kind of like everything that we get started off the ground. It was a little shaky to start and then it really smoothed out afterward. Anything you want to add to that, Leon? No, she said it exactly right. That's exactly how the process of our business and the process of writing the book was. But what was really fun was reminiscing with her about some of those early struggles. And you look back during those days, it was so painful to go through some of the early struggles. But then writing the book gave us an opportunity to look back wistfully at those moments and remember back on those moments.

21:31And looking back on it, those were incredible inflection points in not only our business, but our lives. So that was really fun and rewarding for us. That is really cool. And let's end with a bang because you have written this book. It's not just cookies. Tell us more about this book, Why Fire Nation, an audience and a listenership of entrepreneurs, of small business owners. Why do they need to pick this book up? And then we'll say goodbye. I think this book is a fun, first of all, it's fun and it's light. So it's not super heavy. It's not a textbook. It's all about our struggles. And I think anybody who's starting a business or even wants to start a business or has been thinking about it can relate to the fact that things aren't perfect all the time.

22:21And even if they seem polished and nice from the outside, there's a lot of struggles going on behind the scenes. And we're very, very open about it in the book, our early struggles, some of the mistakes we made along the way, and then some of the learnings that we came out of the other side understanding, but only really with the benefit of having 20 plus years of being able to reflect on things as they've been going. And then we can't forget about the recipes too. If you're a cook at all, a baker, we've got really simple, easy cookie recipes in there that are very fun. It's a gorgeous book with nice photography, so it's perfect for your coffee table.

23:00But really for any aspiring entrepreneur, hopefully it's something that people can relate to, get some inspiration out of, and maybe take a few tidbits away from our learnings. Yeah, I'd love for people to read this and say, wow, if these two can do it and got through everything they got through in this book, then maybe I can do it too. Well, Fire Nation, you heard it from the two authors and they actually have a really cool URL for you to get 20 % off their cookies and or the book cookiedelivery.com slash fire. That's cookie delivery.com slash fire. So Tiffany and Leon, before I let you two go, just really concise and quickly, I'm going to go to each one of you for this.

23:48Share one thing that you really want to make sure our listeners get from our entire conversation today. One takeaway, one strategy, one tidbit. Tiffany, let's start with you. You can do it. If you're looking to start a business or you're early in your business and you're not sure on your next step of growth, have confidence in yourself. It's going to be scary. That's part of the process, but go for it anyway. My takeaway would be there's not one way to get it done. The stories that we share, the things that we went through, what we stand for, our values, we're not saying it has to be the secret.

24:23Our values are the secret to business. It doesn't matter. It almost doesn't matter what your values are as long as you know what they are and you live by them. Fire Nation, you are the average. Of the five people you spend the most time with, you've been hanging out with TC, LC, and JLD today, so keep up that heat. Head over to eofire.com, type either Tiffany or Leon into the search bar, and the show notes page will pop up with everything we've talked about here today. Again, check out their book. It's not just cookies. You can get 20 % off the book and or these amazing cookies that they've been delivering for quite some time now.

25:06Cookiedelivery.com slash fire. That's 20 % off. Cookiedelivery.com slash fire. So Tiffany and Leon, I want to say thank you for sharing your truth, your knowledge, your value with Fire Nation today. For that, we salute you and we'll catch you on the flip side. Thank you so much, John. Thanks for having us. Hey, Fire Nation. Today's value bomb content was brought to you by Tiffany and Leon. And Fire Nation's successful entrepreneurs accomplish big goals, which is why I created the Freedom Journal to guide you in accomplishing your number one goal in 100 days. And we're talking step-by-step. So visit thefreedomjournal.com and I'll catch you there or I'll catch you on the flip side.

25:46Are you ready for the ultimate all-in-one platform for entrepreneurs, marketers, coaches, and agencies? Build funnels, automate follow-ups, manage clients, and even white label your own software, say hello to our featured partner, High Level, and visit highlevelfire.com to start your free trial today. Fire Nation, it's time to stop guessing and start winning with a proven playbook. Inside the Freedom Circle, you'll have access to my step-by-step systems for creating offers, building processes, and driving traffic, all in just 90 days. Ready for freedom? Visit freedom-circle.com to learn more.

From the publisher

From the archive: This episode was originally recorded and published in 2022. Our interviews on Entrepreneurs On Fire are meant to be evergreen, and we do our best to confirm that all offers and URL's in these archive episodes are still relevant.

In 1999, Tiffany accidentally stood up Leon Chen for a date. As an apology, she baked and delivered a batch of warm cookies, and the concept of warm cookie delivery was born.

Top 3 Value Bombs

1. You have more chances to succeed if you build and focus on growing your company first before raising money.

2. You can do it. If you're looking to start a business, or you're early on in your business, and you are unsure about your next growth step, have confidence in yourself. It can be scary, but go for it anyway.

3. There is no one way to get it done.

Checkout Tiff's Treats Website  – Tiff's Treats Cookie Delivery Website

Sponsors

HighLevel - The ultimate all-in-one platform for entrepreneurs, marketers, coaches, and agencies. Learn more at HighLevelFire.com.

Freedom Circle - A powerful community of entrepreneurs led by JLD. Are you ready to go from idea to income in 90-days? Visit Freedom-Circle.com to learn more.

Gelt - Tax season might feel far off, but the real planning happens now. Get a personalized consultation and 10 percent off your first year when you mention Entrepreneurs On Fire at JoinGelt.com/eof.

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