On Friday, October 13, three remarkable woman entrepreneurs shared their their stories, challenges, and triumphs at the “Women in Entrepreneurship” panel at Palomar College. These dynamic founders – Cassandra Schaeg (SIP Wine & Beer), Maya Madsen (Maya’s Cookies), and Deanna Smith (Deanna’s Gluten Free) – offer invaluable insights into their journeys, shedding light on the unique experiences they’ve encountered as female business owners. From their personal “whys” that drive them, to the exceptional resources within North County that have propelled their businesses, take a glimpse into the wisdom and resilience of these accomplished women. Explore their candid reflections, networking advice, and lessons learned in the hope of inspiring the next generation of aspiring entrepreneurs.


How did you become a business owner, and what is your “why” – the thing that drives you?

Cassandra: I will just tell you my why is that I wanted to have freedom. Freedom looks different for a lot of people. For me it looks like working where I want to work, supporting who I choose to support, dressing how I want to dress, and figuring out how to help others in that process. To do that, entrepreneurship is one of the avenues that I’ve taken. I’ve worked for others people before, but there’s just something about creating your own destiny that is peaceful. To be responsible for the work that you produce and to also help other people see the value in themselves.

Maya: I spent 30 years as a personal trainer, fitness instructor, and I’m vegan. I like to say I’m your worst nightmare, a “vegan personal trainer.” I always eat clean and healthy and exercise and gave myself my cheat day. On my cheat day as a vegan, I wanted a cookie, and I could not find a cookie in the marketplace 15-20 years ago. All the vegan cookies on the marketplace were full of healthy ingredients such as nuts, chia seeds, and flax. I wanted a Mrs. Fields style cookie that I grew up eating at the malls in the 80s. So I took a classic recipe and added my own personal touch, a few herbs and spices, and created a vegan chocolate chip cookie. I was known for that cookie. I was the cookie mom. I have three sons. That was my claim to fame in the little kid’s world at their elementary school.

Fast forward to 2013 and my son called from his university and said that we’re behind in our bills for his tuition and his card’s not swiping to get into the dining hall. I gave them my best piece of motherly advice I could: “Sneak in with a friend until I can figure out how to get your tuition up to date.” I made a critical decision to start turning my side hustle and my cookies into a business and started selling them to friends and family. Once I got up to about 20 dozen per week out of my home kitchen, I decided to turn it into a formal business, starting at farmer’s markets and growing from there.

My “why” is I wanted to make sure that my boys were able to have the education that I, unfortunately, was not able to give myself. They’ve already graduated college, so now my why is to continue to innovate in my space, to allow those who have dietary restrictions to enjoy a delicious cookie, and to be able to give back to my community. I started my life in foster care, and I was always the person on the receiving end. It was always a goal of mine to be on the other side, to be able to give back, and now I can.

Deanna: I have always had a business of some sort. Growing up, we didn’t have a whole lot of money, so we always had to figure it out. When you’re in school and other kids happen to need something, like a pencil they weren’t prepared for, and you’re just constantly giving to that person, you think “Wait a minute, I can sell you that.” So I think entrepreneurs are just wired in a certain way. We don’t really fit in a box. I tried to do “regular jobs,” and I just didn’t fit in that box. My mind was always wandering. I always had these ideas, and so I just wanted to do something that was more interesting. How did I get here? A lot of hard work and surrounding myself with a lot of people who knew a lot more than I do. I don’t have a formal education, but I do know how to pay attention to opportunity, especially when it keeps knocking at your door.


What is one of the biggest challenges you’ve had to face as an entrepreneur, and how did you overcome it?

Cassandra: COVID was definitely a challenge. But it forced people to be still, to think about things, and to focus on themselves with some introspection. As an entrepreneur, you’re always going, going, going, and you don’t get to slow down. You’re always problem solving. We go through challenges every day as entrepreneurs. Depending on how we look at it, it’s either an opportunity for growth or an opportunity to fail. How I overcame it? I created a TV show. I wouldn’t have been able to do that had we not been at home for a year during COVID thinking, “What do I do now? I know. Let’s do a TV show.”

Maya: As an entrepreneur, every day there’s a challenge of some sort, so you have to persevere. I like to say, “Put my big girl pants on, and figure it out.” That’s my personal motto. For me, the biggest challenge to date would be June of 2020 during COVID and our business went viral due to people posting black-owned businesses to support.

I had been doing about 20 orders a day on our e-commerce site just to keep the lights on. Overnight, we – myself and one other employee – had 10,000 orders in the queue. You can see how daunting that was. I asked my equipment person, “How am I going to do this? Do you have any piece of machinery to help me produce these 250,000 cookies I need to produce?” You really do have to surround yourself with people who know more than you. So that almost killed me. It took a toll on my loved ones. It took a toll on me. It took a toll on my employees. But we persevered. We were able to scale our business up six times over because of that.

Deanna: I’ve been in business for 15 years. For this particular business, I’ve had a mindset that “I’m going to be prepared.” Just when you think everything’s going well, the ovens are going well, everybody’s showing up to work – there’s always something. You’re always on your toes, waiting for something. So just being prepared is the hardest thing. And surrounding yourself with people and discernment.


Can you tell me if there are any additional aspects or challenges you encounter as a female entrepreneur? Specifically, are there any unique challenges you face as a woman in the role of a business owner?

Cassandra: We don’t have enough time for that.

Deanna: How long is this event going on?

Cassandra: One of the reasons I opened SIP in lovely Escondido was because it was an opportunity. When I look around the room, and I see women who are doing phenomenal things, I can’t help but notice that there are not a lot of people that look like me in this room. When you’re trying to pull for motivation or support, and you’re trying to figure out what that looks like, it could be daunting.

I’ve heard a lot of us say that we have people that are smarter than us in our circle. I think that’s the biggest thing. I need all my friends to be smarter than me. We have big dreams, and if you have the right people in your corner supporting you, and when you’re prepared, many people won’t say no when you ask for help. Being a black woman, there’s not enough wine in the world, but being a woman in business, we all know what that looks like in terms of statistics.

We’re growing, we’re opening businesses every day, but we don’t get the support. You talk about venture capital money, you talk about visibility, trying to get money for loans – everything you can think of. It’s hard, but it takes the hustle to make it happen. If I were to be open for one year, that would have been fine with me, but to be here almost nine years? It’s definitely a blessing, so thank you.

Maya: So many challenges as a woman, and definitely as a woman of color, there’s an extra layer of challenges that go along with that. For me I had imposter syndrome and insecurities, because I didn’t have a formal education. My education was on the streets. So I always hunkered down a little bit, and I let other people think they were smarter than me, because I was afraid to really speak my mind, to say what I know. Don’t ask me why. It sounds ridiculous now, but I finally came into my own and realized that I’m smart, and I know what I’m talking about, and I know what I’m doing. Sometimes I don’t, but I will find out and if the person in front of me is uncomfortable with that that’s their problem, not mine.

I finally came to that realization one day because I had an electrician come into my facility to do some work on a new piece of equipment. And the minute he walked in the door, all he was doing was giving me advice on what I should be doing. And mind you, this is a vegan bakery. He’s an electrician. I finally just said to him, “I hired you to do my wiring, not give me business advice, so can you please just do the job that I hired you for. He looked at me, and his assistant looked at me, and I think that was a turning point for me when I said, “I have a voice. I know what I’m doing. I’m smart. I’m driven, I can do these hard things, and I’m no longer going to lower myself to make someone else feel comfortable.”

I’m not a mean person, at all, but I just have my voice now. That’s one of the many challenges – showing your strengths and not worrying if the person on the other side of the table is uncomfortable with that.

Deanna: When I introduce myself, after maybe having some dialogue on the phone with a potential client, and I show up, and they say, “YOU’RE the baker? But you don’t look like a baker. But you’re so skinny. And they ask me ridiculous questions like, Do you eat? Do you eat meat?” And I just laugh. People have to get past all of this – the image, what they see in front of them. You just have to let them think through all of those things that are so confusing to them when they’re looking at an entrepreneur of different color. And we’re female. And wait a minute, you have a business? And, oh, you have a brain? So it sounds harsh and crude, but that’s our world. I don’t know how to say it any other way, but getting past those barriers is always such a waste of time. Because if we weren’t women of color, and we were men it would just be boom, boom, done. But the biggest challenge is the constant hurdles. Not explaining, but almost having to prove our work.


A panel of three women plus one moderator in front of an audience


With those challenges in mind, how have you each championed diversity in your own business and industry, and what benefits have you seen as a result?

Cassandra: That’s just what I do for a living at this point in my life. It makes me very happy. There’s nothing wrong with helping other people. There’s nothing wrong with supporting people who don’t look like us. I know that as business owners, we’re sometimes in this bubble of trying to do our thing. But if we pick our heads up just a little, sometimes that we can help each other.

Maya: I try to source BIPOC brands for our ingredients. In fact, (Deanna and I) are about to do a collab on some gluten free dough. In our refrigerator case, all of our drinks are BIPOC brands, and I proudly tell my customers when they come in. I just intentionally source those when I can and it’s more expensive, but I don’t care. I want to make sure that as my brand’s growing, I use my platform. We have a black history cookie collection every year in February that I’m working on right now. I create cookies with a theme, and I try to tell alternative black history with those cookies. Tell the history that you didn’t learn. And also support other black and brown brands by using their ingredients.

Deanna: Supporting the community is being involved in the community. Lifting up our heads out of our bubble is challenging at times, because there’s always something to be done in our workspaces. But if you can take the time to spend time in your community, it will pay over tenfold. I have had many people in my community come to me in the beginning, coming in and buying my products. They would come and say, “My 8-year-old son has never had a birthday cake. Can you make a birthday cake?” When I gave her the birthday cake, and I would be crying, and the kid would be happy… I cherish those moments because when I’m sitting at my desk, and my ovens are down, or something crazy is going on. When people come in and they’re so grateful – those are the moments that keep me going.


I agree, those moments are so cherished and important. With that in mind, can you share a moment of great triumph in your business?

Cassandra: I would say winning an Emmy was definitely a triumph. You create a television show, supporting women and people of color in industries, and you don’t think you’d win an Emmy for it. Putting a team together to make that happen was the hardest thing I’ve ever done. What was really important was being intentional about how we were going to see ourselves on television. Looking at what’s currently out there and wanting to be the complete opposite of that. Making the show, and making sure people knew that there are people like us in this world who are doing phenomenal things, even if they don’t see on television.

Maya: There’s one thing that’s a great triumph for me is when I became a Washington Post recipe contributor. The Washington Post was asking me, from Sacramento, California in the hood, who doesn’t have formal education, who has no culinary training, becoming a Washington Post recipe contributor, and they paid me! I felt validated. I thought, “Okay, I think I know what I’m doing. I think I’m a professional.”

Deanna: The moment that I actually spoke with Jacques Pepin. He is a world renowned chef. KPBS has a lot of his shows. He was best friends with Julia Childs. He invited me to his charity ball dinner, and then he invited me to be in his digital cookbook, and I just couldn’t believe it. Because we come from humble beginnings, we don’t have a formal education, so when that stuff happens to you it brings you back to when you were a kid, running around with no shoes on, playing with your cousins or siblings in your neighborhood that’s not very fancy. It’s just so surreal. Just to be next to somebody who continues to do amazing things in the community.


Those are all so amazing. I love it! Let’s switch gears a little bit to focus on our region. What resources or organizations in North County have been particularly helpful to you on your business journey?

Cassandra: I’m going to give a shout out to Cal State San Marcos. My business was part of the Senior Experience Program. You’ve got to listen to these kids, because they know what they’re talking about. I was having a hard time trying to tell the story of what SIP was and what we’re setting out to do. Four college students in marketing were like, “Oh, you just need to do this, this, and this.”

And I’m like, “Well, you done saved me about 20 grand in marketing!” Look, you have to surround yourself with people who are smarter, and you also you just have to listen to the children. I mean, we’re sitting here at a college, and these kids know more than we will ever know, given what this world is morphing into. I’ll stick around with the college kids. Anytime I can talk to them, and ask them about what’s happening from technology, to how are they getting information, to what would they like to see… Don’t mute those children, because they’re pretty much our future.


I love that. We used the Senior Experience too, and it was really amazing. The value you’re getting out of these projects verses how much it costs – it’s like pennies in the bucket, really.

Maya: You said exactly what I was going to say. My business is in North County, near Cal State San Marcos which has been a huge part of my growth. The students, the staff, the organization’s there – they’ve all helped me. The mayor in San Marcos, Rebecca Jones. She has opened doors for me there, and she’s hugely supportive as well. And my fellow business owners, Cassandra especially, because whenever she has an opportunity where she thinks I could have an opportunity, she will contact me and last minute, no minute, whatever. And the answer is always, “Yes.” So my fellow business owners, the university, and Innovate 78, which we are both a part of, has been invaluable, helping me grow, giving me exposure, opportunities. We partner with the San Diego Boys and Girls Club as well, and we are able to have interns that they pay for.

As a small business, that directly affects my bottom line, having interns that the community provides. It also gives them an opportunity to have their first job, learn how to be an employee, how to show up on time, and all those things. North County is a hidden gem that I didn’t know was out here, and I’m so happy I’m now a part of it.

Deanna: Definitely my community. When I started my business, I had already made loaves of bread for my family. I made some gluten free bread for my 3-year-old cousin. She took it to preschool, and people started calling me. Every Sunday, my numbers grew, and I just kept making more and more bread.
Finally, I said, “This is ridiculous. I need to figure out what I am going to do on a grander scale.” I didn’t know anything about massive production. I didn’t know that there were giant mixers that you could take a bath in.

So, I reached out to my community. There is a place called “The French Bakery” on Grand Avenue, and I was very good friends with the owner at the time. I would eat there all the time, and they made fresh pastries. I said, “I have this recipe, and I need to scale it up.” He gave me a tour in the back. He’s got a big ole mixer, and he had a French baker. He told me to come anytime, and we could make it here. I didn’t know where to get the ingredients, and took my list and called his source. The next week he had everything I needed. We developed in his bakery. It was amazing.

There were other people who guided me on industrial bakeries. When you are involved in your community – people want to help you. They stumble over themselves to help you. Especially when you’re doing something amazing and new. They all want to know: “What are you doing? What does it taste like? Can I taste it?” So, community definitely helped me grow in almost every aspect.


A common thread in all of your answers is creating connections within your community, forming mutual help for one another. Since there are many students in the room who may not have had a chance to do much networking, how would you advise them?

Deanna: Fake it till you make it. You have to like it. Sorry, you just have to. I don’t like speaking in front of people. This makes me very nervous. Sometimes you’ve got to go talk to somebody who might hold the keys to your future in one particular company. You have to find your courage, and how do you find your courage? You surround yourself with people that you trust and will be your cheerleaders. Have a core group of people who will help you be strong. You are strong, but you don’t always have to be strong. Lean on your friends. Lean on your support. Go to people who have more information.

Maya: I like to say your network is your net worth. I am an introvert. I am uncomfortable mingling. I don’t drink, so I can’t loosen up with a little drink. So it’s extremely difficult for me, because I used to feel like I don’t have anything in common. Once I started forcing myself to get out of my comfort zone, and it was painful because it was uncomfortable, and networking and going to events, things started happening for me. Every event, I walked away with a meaningful connection that led to something else that led to something else. Now I go to everything, and I always say as I’m driving there in my head, I wonder what meaningful connection I’m going to walk away with at the end of this event.

Cassandra: One of your biggest assets is going to be the relationships that you build. One of the things that I’m fortunate to have is the ability to connect the dots. I see someone, and think, “This person’s looking for this, this, and this.” I can leave the room now, right? Because I’ve done my due diligence. At the end of the day, this is our community. We all run into each other. Someone’s always looking for a job, a hairdresser, something. If you have that information, the greatest thing you can do is pass it on. Because when you think about someone’s going to bring your name up anyway. So there you go – it’s the gift that keeps on giving.


Thinking back to when you first started your business, what one piece of advice do you wish that you would have heard? What would advise would you give to the aspiring entrepreneurs here?

Cassandra: Oh, mine’s always trust your gut. That’s it. Trust your guts. Our intuition is a barometer for a lot of things and if something doesn’t feel right, don’t do it. The other thing is, it’s okay to say no, and not have to give an explanation. Just, “It’s a no for me.” The last is, really focus on taking care of yourself. Entrepreneurship is so hard. There’s Sundays where I just sit, stare, and watch Lifetime movies, and that is what I need in order to get through another week.

Maya: I was going to say trust your gut, but you already said it. I will say the other piece of advice that was difficult for me is when you’re starting a business and you need staff, sometimes your friends and family are the only people around that you can source from, because you don’t have any money to pay people or whatever that may be. As your business grows and scales, sometimes those same people don’t have the skill set, the mindset, or whatever “set” it may be to help you continue. I had a lot of friends and family working for Maya’s Cookies, and when we scaled six times over, overnight, some of those people weren’t able to keep up with the accelerated growth, and I had to make some difficult decisions. Hire your friends and family if you need to, but just know that as your business scales up, some people that were with you in the beginning may not be the right people as you grow, and that’s okay.

Deanna: Definitely trust your gut, because we’re wired that way. Don’t let anybody tell you that you can’t. Don’t let anybody tell you that you’re wrong, especially when you’re trusting your gut. Stand up for what you believe in, and don’t let anybody take your identity. When you are out there working, you have a million things to do, you are understaffed, and you don’t have any money, make sure that you are taking care of yourself first. Everyone else can leave. They can get another job. Make sure that you do everything in your business for yourself and the growth of your business, because at the end of the day, you’re the one. Whatever project that you’re creating, keep your creations to yourself. Trade secrets, all that stuff. Make sure that they’re all protected. When things get really hard, I always lean into my faith, so that’s what I would recommend.


(This event was co-hosted by Palomar College and San Diego North Economic Development Council and moderated by Caitlyn Canby.)


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About the Author

Caitlyn Canby loves to discover and share people’s stories. She has her bachelor’s degree in Communications, Print Journalism with over 8 years of journalism experience. An Escondido native, she just moved back from Catalina Island to North County with her husband and two children to the town of Fallbrook. Caitlyn enjoys collaborating on projects as Marketing and Events Coordinator at SDNEDC, traveling, and exploring new restaurants, venues, experiences, and cultures.





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