Meet Linsay Smith of Gypsy Cup in Gilbert

Today we’d like to introduce you to Linsay Smith.

Linsay, can you briefly walk us through your story – how you started and how you got to where you are today.
I became a corporate accountant after college. I thought the safety and security of a job like that would make me happy. Turns out, I am not the cubicle type. After I had my second baby, I made the decision to stay home. I had two babies in two years and the day care cost alone made working not worth it. A couple years later, I had baby #3 and it was tough. Mentally, emotionally and physically. I wanted to be home and had no desire to go back to my cubicle but I also was drawn to do something meaningful and impactful that I could work with and around my kids. I have always had this idea that life could be different. That, maybe the 9 to 5 did suit our family and goals. There was a tug that there was just something… more.

Ainsleigh, baby #3 was a horrible sleeper and I was up in the middle of the night when she was just months old, scrolling through Instagram and I saw a picture of a tiny teardrop trailer someone converted to a coffee shop somewhere on the East coast. I swear it was what I call a lightning bolt moment. I just knew that was what I was looking for. I have had a lifelong love of coffee, travel, a meandering, unconventional life and this checked all the boxes. I saved a copy of the photo and it became my constant day dream. Mind you, someone with 3 kids under 5, the youngest 3 months old, a mound of debt, a husband that traveled for work, was not the ideal candidate to start something that: 1. we had no background in; 2. had no money for; 3. had no time for, so I kept it to myself and a close friend.

When the tug of this outlandish idea didn’t relent, I started writing it out. How many customers I thought I would need to be profitable. How much it would cost. Who would build it. All of that. I literally had NO clue what I was doing. None. But, I gathered information bit by bit. I researched constantly and saved pictures and design ideas. We LOVE travel and Europe so I knew I wanted it to look like this little cafe on wheels and not concession-y. I soon realized, that it would cost a lot of money that we didn’t have. I also didn’t want to leave my 4-month old baby in daycare if I could avoid it, also we couldn’t afford it. So, I took a night job at a country club down the street bartending, serving and working whatever I could in opposite hours with my husband to cut down on babysitting costs. I did that for 18 months. It was a hard, relentless, draining time. My husband and I never saw each other. There wasn’t much family time. It was really difficult but also really necessary.

When we decided to proceed with this crazy idea, we chose to have the trailer built in Portland since they are known for their food trucks. The process would take a while and I continued to work my bartending job to pay for it. As I began to speak more about what I was building, people began asking me about my product. I started recipe testing and got our cold brew nailed to perfection. I still had no trailer and was working at night. So, I decided to do it old school. Like an adult lemonade stand. I ordered $400 in supplies from Amazon and just started. I opened on my driveway for my neighborhood. Partly to get feedback on my recipes and then my kiddos wouldn’t need a sitter. It actually kind of took off. I began working Saturday and Sunday AM on my driveway and making as much as I did bartending. So, while the trailer was being built, I was able to quit bartending and jump into the cold brew side of the business right on my driveway. It was the strangest thing. People from the neighborhoods around us would come out. I sold a ton of cold brew like that. And it was a total fluke that I just got fed up working nights and away from my family. I just leapt. I began to target people that wanted indoor coffee bars and anything I could do till we had our full size unit.

The trailer was permitted and finished in January. I still knew VERY little about food trucking. I had no events on my books and most food trucks have pretty full schedules by then. I had nothing. My husband and I made the decision that we would say yes to everything for one year. Big or small. Since we knew nothing, we were going to act like it. So I straight cold called and pitched myself to anyone and everyone. I put myself out there. I did things for free. I did things I lost money on. I did things I made a ton of money on. I worked 7 days a week. It was nuts. We started to build momentum and word of mouth. We have a unique cold brew offering and cold brew is all the rage so that helped. But we got where we are on straight grit, hustle and failure if I am honest.

Overall, has it been relatively smooth? If not, what were some of the struggles along the way?
No. This is absolutely the hardest thing I have ever done. And the most rewarding. First, juggling my husband’s full time job, 3 kids in school/activities and this demanding business poses its own challenges. We have faced EVERYTHING. Our top of the line generator had an one in a million defect that failed constantly our first month and was in the shop. I hit a pole with the trailer that cause damage to it and my ego. We showed up at a lot of events and made little to know money. We blew tires on the side of the road. Our truck’s radiator blew on the way up north to a big event. I have missed sporting events and gymnastics meets. I have been rejected dozens of times by events I REALLY wanted. I have worked myself into the ground and ended up with $11 in our bank account. The learning curve was steep and unrelenting. The size of the trailer means it is hard to park and put places. Our county is TOUGH with permits and each city requires a different one on top of that. We had to learn how to operate equipment, make a latte, social media. It was just a lot to learn at once. It was the school of hard knocks for sure. But it was a TON of fun. But no….. that road was NOT smooth. Paved with coffee, wine, tears, laughs and grace.

Alright – so let’s talk business. Tell us about Gypsy Cup – what should we know?
Gypsy Cup is a traveling cafe. We specialize in a unique combination of quality, style and mobility, Gypsy Cup offers an experience like no other. Traveling around to local events, weddings, festivals and markets, Gypsy Cup makes a lasting impression with exceptional product in a mobile setting. We have expertly crafted espresso drinks, coffee and a custom 8 tap system. We started becoming known for our cold brew (especially our vanilla bourbon) because of the unique flavor profiles that are not sugary or sweet. We do everything small batch and homemade so it really is a quality product. Our strawberry basil lemonade is another cord favorite that people go nuts over. The massive tap system makes it easy for us to handle large crowds and lines efficiently. That is a must in the food truck world. It is rare you have to wait long for coffee from us!

I am most proud of the efforts I have made to make us not just another coffee company, but a brand that is based on community, craft and connection. I think that it is something the world is lacking. You can get coffee anywhere. I know that. So, while I love coffee and my business, I love the entrepreneurial journey. I love inspiring other mama’s do their thing. I love giving back to the community and becoming rooted in those things that matter. People gravitate to that. I am pretty open about what it takes to bring this dream to life. Transparency is scary but it has gotten a lot of positive response and I am most proud of that. I don’t see us as just a coffee company. I see us as entrepreneurs that will one day have a model that we can use to teach other people and families to become self-employed. I am a HUGE fan of authenticity and people rocking their passions so I am most proud that Gypsy Cup is that platform I get to express that.

I think that is what sets us apart. Our willingness to be honest, transparent and connected. I am pretty big on that… I think our cold brew is pretty life changing and we put A LOT of effort into it. We don’t cut corners. We give back. We love doing what we do. We also pay attention to detail. I (try) to think of everything. I want to be highly styled, provide great service and exceptional product. I leave no detail out. I want it to be an experience you remember to visit us.

Any shoutouts? Who else deserves credit in this story – who has played a meaningful role?
My husband deserves the most credit. He has been ride or die in this with me. We have never thought we would just be a food truck. He is in and good with all the crazy avenues, expansion and things that can come from this.

I cannot go without mentioning Sarah. There would be no Gypsy Cup without her and I mean that. Before I could speak about this crazy idea to anyone, including my husband, I told her. I was exhausted from a new baby and she really pushed me to explore the idea farther and gently pushed me to take myself seriously. She has been such a champion for my business and someone I trust with everything I have.

My business coach and good friend Jenni is also in that camp. She has helped me get focused on my goals, grow, achieve things I never thought possible. She is also the BEST at what she does and just good people. I trust her with everything I have as well and we will always be grateful for her undying support of our business.

Our equipment guy Jeff. May sound strange to name someone like that but he knows this business inside and out. He really gave us great advice and helped us with things that he didn’t need to. When we were trying to get the trailer finished, we had it at his shop for literally months and he never complained. He was the first person that told me that he couldn’t wait for me to call him up and tell him how many thousands I made in a weekend. It never occurred to me, I would EVER make $1000 in a weekend. So, it was encouraging to have someone who wasn’t related to me, believe in me. He was an angel in many of the challenging times.

Our families. This was a group effort. My mother in law watched our kids countless times so we could go do crazy big events. My dad helped us hang our sign which took about a solid day. Not to mention the countless texts and calls he answered and helped us so much. My mom was there to be my moral support. I come from a family of entrepreneurs so they knew what I was undertaking. We were really lucky to have a lot of people cheering us on along the way.

I always say we are not self-made… we did the work ourselves, but we had A LOT of people, without which, we would not be here.

Contact Info:

• Address: Gilbert, AZ
• Website: gypsycup.com
• Phone: 4807764960
• Email: thegypsycup@gmail.com
• Instagram: gypsy_cup
• Facebook: GypsyCup
• Twitter: gypsy_cup

Image Credit:
Amy Termini Photography, Scout and Briar, Chelsea Herrera Photography, Herhashtaglife-Bre Geiger

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