What challenges could come up when you turn your passion into a business? Meet husband and wife team Ashley and Tony Ross, who went from real estate and law enforcement to starting Cucina di Pizza. Hear their story about how they made it happen.
What challenges could come up when you turn your passion into a business?
In this episode, your host Jenny Dempsey chats with Ashley and Tony Ross, the dynamic duo behind Cucina de Pizza in San Diego, California. They share their incredible journey of leaving behind their careers in real estate and law enforcement to dive headfirst into the pizza business. Ashley and Tony started by perfecting their pizza recipes and using Instagram to build a loyal following, one delicious slice at a time.
But the road wasn’t always smooth. They faced challenges and setbacks, but their resilience and commitment to delivering a top-notch product and exceptional customer service kept them going. Now, Cucina de Pizza is known for its creative and mouthwatering toppings like biscuits and gravy, barbecue chicken, jalapeño popper, and a variety of veggie options.
Ashley and Tony’s story is a testament to the power of taking risks and pursuing your dreams, no matter how unconventional the path may seem. Tune in to get inspired and maybe even get a little hungry!
Episode Takeaways
Connect with Cucina di Pizza
Jenny Dempsey (00:00.15)
I knew when we made the decision to go in, nothing was going to hold back because you could stop yourself and say, what if, what if, what if, you just have to go for it. And you have to expect rejection because it will happen and it will, people can ghost you and you can't let that affect you. to the career flipper, a weekly podcast featuring career change stories from people around the world and a bunch of different industries about how they get from point A.
to point B and all the twists and turns in between. I'm Jenny Dempsey, your career flipping host. After more than a decade working in customer service and experience leadership at tech startups, as well as teaching a couple Udemy training courses, speaking at business conferences and stuff like that, I got laid off. And despite my experience, I received hundreds of job reductions. I just couldn't land a new job. I really started to question my worth. What am I supposed to do now?
Then a friend gave me an old junkie table. For whatever reason, I saw potential. I binged YouTube, TikTok, and Instagram videos to learn how to fix it up and found this brand new joy in giving something unwanted another chance at life, which really resonated with me after getting laid off and feeling unwanted myself. So this led me to start my furniture makeover and restoration business.
San Diego Furniture Flipper where I rescue and restore good furniture to keep it out of the landfill. You can follow along with the makeovers over on Instagram. Alongside Furniture Flips, I host this show, speak at events, and yes, still do some small -scale customer service contract work on the side. And even with all these amazing things I've developed over the past couple of years, I was feeling pretty alone and wondering if I was a bit delusional about this new path. I mean,
who really goes from the corporate tech world to being covered in paint and sawdust in their garage. So I reached out to a few people I knew who had also flipped their careers. Hearing their stories motivated me and it made me realize that it's okay to change direction at any point in life. And I soon discovered that there are way more people out there who flipped their careers more than I'd ever imagined. I thought if their stories are helping me feel less alone and more confident on my career path,
Jenny Dempsey (02:21.356)
They might help someone else too. And that's why I created this podcast to share these incredible stories and offer support to anyone considering going through or having already been through a career flip. So wherever you are in life, I hope this podcast inspires you to dream bigger, learn from those who've changed their careers and embrace the changes and risks that can help you grow beyond what you ever thought possible. All right, let's slice into this episode. Meet Ashley and Tony Ross.
Ashley's experience is in real estate, and Tony served for 20 years in law enforcement. Now, they've found a new recipe for success by flipping their careers into the pizza biz, founding Cucina de Pizza, a Neapolitan -style San Diego pizza pop -up that's dishing out creative and delicious pies all over the city. In this episode, you'll get a taste of what it's like after making a career flip and really figuring things out along the way.
From keeping track of what you learned to building a cult following with some seriously unique toppings and recipes, they didn't let the fear of not knowing get in the way. They just dove right in. And of course, I totally derailed the conversation toward the end when I got hungry and started asking them about their pizzas. Fair warning, you'll be craving a slice by the end of this episode. Let's go.
Hey Ashley, hey Tony, how's it going? Hey, thank you so much for joining on the Career Flipper, although I feel like we need to throw in some pizza puns, like really, you know, to like get this party started, am I right? Need, K -N -E -A -D, let's go with that. Exactly. my gosh, I'm so excited to have you both here chatting about your career flip.
simply because you make the most delicious looking pizzas. you know, and we've been following each other on Instagram for a little while. You're here local in San Diego. And so tell everybody about what you do.
Jenny Dempsey (04:22.732)
Well, Ashley's been, during the COVID time, she got into the bread making. I grew up Italian and it's big Italian family. I love Italian sandwiches. So I kept asking her to try to make Italian hoagie roll. So that's kind of where it started. And then she got that down and I'm like, Hey, what about pizza? You want to try pizza? She's all, I'm not making pizza.
And I said, I am pretty persistent. And I said, just give it a try. So she finally did. And you know, it turned out pretty good. And then I saw her the next day. I'm like, what are you doing? She's all, it wasn't good enough. I'm making it again. I'm all, what? I said, okay. I'm a perfectionist. And literally it was every day. I'm all, babe, what are you doing? She's like, I gotta get this perfect.
She's all, I'm making it, it's got to be perfect. And then it got to a point that she felt comfortable giving it to our friends and family. And they were like raving about it. And I'm like, my God, this is delicious. A few of our neighbors, he said he could eat pizza every day. So they were like kind of our guinea pig. And we just started experimenting with different toppings and whatnot.
and Ashley makes a phenomenal biscuits and gravy. So we put that on pizza and he couldn't stop talking about it. I I saw him in the grocery store and he stopped me and said, if you ever bring that biscuits and gravy pizza, I will eat it every day. I promise you that was the best pizza I've ever had in my life. And it didn't stop there. mean, Ashley just kept perfecting the dough, trying different flour combinations. And then it just got to a point where it was just pretty mind blowing.
to be quite honest. It took a long time to get to that point. We've been working on the dough for what? A little over two years. because there's so many different flowers and like fermentation processes that go into it. So we finally got it to where we were mind blown. And then our friends and family were like, you guys could start something with this. And then we kind of just talked about it. I had recently, I'm
Jenny Dempsey (06:39.054)
former law enforcement and I did about 20 years in law enforcement. then my dream since I was a kid was owning my own business. I kind of followed the path my mom wanted me to do. I went to San Diego State, graduated the criminal justice degree and then went into law enforcement. Just kind of the traditional path. And they weren't real supportive of running my own business and being an entrepreneur because that's just not how they were raised or how I grew up.
But once I left the law enforcement, I bought into a franchise system, which was barbecue cleaning, repair and installation service. And I ran that for approximately five years. Finding quality employees for the type of work we did was a huge challenge. So one of my buddies that ran Temecula Valley franchise, he came to me with an offer to buy my territory. So Ashley and I discussed it and I...
thought, you know what, this is probably a good time to exit. then I started a magazine publication, which is local community magazines. We're going to be launching one in Bonita here within the next few months, probably around September, October. And it's just community -based that friends, families speak about their life and like kind of a podcast, but in print form.
And Ashley and I actually were sitting down talking one evening and she said, should we just go for this? I'm all you serious? And she is like, I think we should. I'm like, we just kind of went in head first because I, I actually work two jobs as well. I'm in the home appraisal business and then I, I'm also a realtor. So my schedule is flexible where we could do this.
So we kind of just dove in and bought the oven and everything that we needed and we're like, let's go for it. We literally sat on the couch and wrote a list of everything we needed. Ashley bought a journal. She's all, I'm going to document every detail. And that's key to any business. If you're starting, it holds you accountable. So I bought this journal and I'm writing everything down. And the first month it was just,
Jenny Dempsey (08:59.896)
you know, bought this, bought that. But then it became our scheduling book, writing anything that happened, good or bad, funny, you know, events that didn't work out like we thought they were. But having this journal holds you accountable for the goals you want that you set for yourself. And I think that is super key to any, if you're starting a business is to buy a journal and write everything down, everything.
Yeah. And literally the good, the bad, the ugly, I mean, we go through the journal and kind of read, my God, I remember that, you know, it's just kind of cracks us up. That was Ashley's idea. And it was a game changer. And then Ashley, you know, started the Instagram and because she's like, how are we going to get gigs? You know, how are we, you know, where are we going to set up? And we didn't really have that plan yet. And I said, well, Instagram was good to me through the barbie clean business. didn't
know anything about social media. And I kind of just learned as I went. Ashley's way better at it. She's very creative. I just did before and after photos. She just started it and you know, we started gaining some followers. And then she's like, I'm to reach out to this brewery. Yeah. And so that's really how it started. And we've gotten all our business from Instagram. It's huge. So he was really successful with DMing establishments. So that's really how it started. I
Damn them with what we did in our process and they gave us a chance and we, you know, we set up and. It's kind of just taken off from there because then it started becoming word of mouth, you know, and we, you know, when Ashley started reaching out to like apartment complexes, not realizing that they have sister complexes and then their community manager would reach out, you know, and then it kind of just snowballed and she's like, my God, we're like.
fully booked. And I'm like, geez, that was quick. You know, our first like official launch month, we were booked literally like four days a week. We take Mondays off because our son has an event that he has to go to. So we take Mondays off, but it's literally like he said, it's snowballed. We have to turn jobs down, unfortunately now. And I mean, we we have people traveling an hour away.
Jenny Dempsey (11:26.594)
just to get Ashley's homemade ranch. She makes a spicy ranch that's out of this world. And people want to know if we sell the ranch itself. He had to push me to get the ranch on the menu though. Cause I'm a salad person and long ago I gave up bottled ranch, but I love ranch. So I found a recipe that just worked, but it's not the same as pizza ranch. So he's like, you got it, work on a pizza ranch. So I'm like, okay.
Maybe, but because our crust, it's so puffy, it's like a breadstick. So I rethought about it I'm like, all right. So I had to tweak the salad ranch and then landed, cause it's gotta be a thicker ranch and it is phenomenal. we've got regular and then we've got the spicy, but the spicy tends to be the most popular and it really works well with our dough. Yeah. It kind of blew her away when so many people were coming back.
and letting us know that they want us to bottle the ranch and sell it to them. And that's possibly in the works. We're discussing it, but right now we're just enjoying what we're doing. It's kind of neat seeing the following. We have regulars that come to almost every event and literally like two, three, four days a week. I'm like, man, and we look at each other, three and pizza like four days a week. it's just, it's wild how it's kind of taken off so quickly. We weren't expecting that.
Yeah, that's amazing. That's amazing. It started from something that you were perfecting and just curious about, wanted to do really well. And then you were just making people so happy with this delicious pizza that it sounds like it just was a natural decision for you to make. Like, yeah, let's bring this to more people. Were there ever any points throughout the journey when you were starting out?
that you were like, I'm not sure if we should do this or were there any like hesitations or even imposter syndrome or any things like that that you were thinking maybe we shouldn't do it this way? Like what was that like for you? Well, for me, and I think Ash would agree to this is, you know, and we mentioned the imposter syndrome and I am familiar with that, you know, because I felt that a little bit with the barbecue cleaning because, you know, we would turn terrible grills in brand new.
Jenny Dempsey (13:48.66)
and people were just floored and wowed and then they would spread the word. So I was kind of using that with the pizza. I was incorporating that experience with the pizza. In the beginning, we were, for our ingredients, even though Ashley had the dough perfected, I I knew the dough was phenomenal, but then we started discussing ingredients. We were getting in the beginning, basic ingredients, your pepperoni that you could get at any local grocery store.
And I said, okay, now we got to up the game on the ingredients. We both wanted the best ingredients possible. So I did a ton of research in regards to, you know, the Italian sauces, the pepperoni, the cheese, all of it had to be top notch. So that took a while. I didn't know how to go about it. You know, and you do get doubts like, wait, is this for big time restaurants? Is this, you know, we're just a husband and wife team, but
I got some connections and we got it hooked up. know, so, I think that was the only time I thought, you know, is this, is this really happening? Like, can we make this really legit? And I, we both feel we got to that point. yeah. Yeah. Wow. Yeah. then it, and then it sounds like, know, when you were messaging people on Instagram and using that social community tool to really build out, you know, your, sounds like
cult following almost at this point, like you're loyal customer base people driving an hour to come get these pizzas. That first direct message that you might've said, I don't know if I can hop back into history here, but like you sent that message. Did you have any expectations? Did you think that, okay, they're going to reach out? Did you have any thoughts like, what if I never hear from them or?
Were you unattached to the outcome? Because I think sometimes a lot of people get held up like they got this great idea, they're going all in and they're like, wait, now I got to find people to actually, you know, buy this. And sometimes they get kind of, stop in their tracks of like, you know, whatever reason they might get scared or they might feel like what if it's not good enough yet or all the things. there any, when you were like sent that first message, what was that like? You know, you have to have thick skin. And I think
Jenny Dempsey (16:04.042)
at my age now, like I have that. I knew when we made the decision to go in, nothing was going to hold back because you could stop yourself and say, what if, what if, what if you just have to go for it and you have to expect rejection because it will happen and it will, people can ghost you and you can't let that affect you. So when I did send the message, I mean, I sent multiples, right? And I
didn't have an expectation, you know, cause we're brand new. and when people did reach back out, it's like, wow, you know, like it was the sense of achievement. Ashley jumped up and down when we got our first meeting with a brewery. She's like, my God. And we got connected. One of our first clients we got connected with was an apartment that's literally a mile down the road from us. And it was a,
bi weekly contract. And that was I'll never forget it. I just felt so like happy like we did this. And, you know, people want, you know, a pizza pop up. So you can't worry about what if and you have to have thick skin and expect rejection. Yeah, early on. I mean, we had a lot of like, geez, that sucked.
you know where we went to a brewery and it was they sold three pizzas and we're sitting out there in the dark and looking at each other and it's just, we got in the car, we took some positives from it and, because we got some other connections through that event and you know, we don't dwell on the negative, you know, because not every event is going to be successful. cause with our product,
we have to throw away everything that we don't use. Cause the dough has a certain amount of life, you know, after, you know, it's bald. So we take it to an event. If we don't sell it, we've got to toss it. So there's a lot of product waste. So we have to deal with that. And then on top of only selling three pizzas, you know, if you don't have a positive outcome or outlook,
Jenny Dempsey (18:24.756)
or believe in yourself, you'll never make it. it's, yeah, we're still dealing with that, but we do feel very positive about our business and what we have that we can look at something negative like that and we could take out the smallest positive. Like we made a connection, you know, if that's the only thing that we took from that night. We had an event at one of our top complexes.
that we sell out every time within an hour, an hour and a half. And we had a major malfunction with the oven. And I did even having the barbecue cleaning repair experience, I knew what it was, but I didn't have the part and I knew it was shot. And we had to refund 15 people and pack up and leave. I mean, so everything's not, you know,
peaches and roses, you know, you take the good and the bad. So we just like kind of that sucked, but we're driving. Okay, that'll never happen again. I'll have that part on hand and write it in the journal. you'll always remember it. Yeah. You know, so we're very transparent, you know, it sucked with, we had a crowd around us when all this was going on.
And you're in the hot seat. mean, you're on stage there and it's just like. And I, we both had to address the, you know, all our customers that were waiting for the pizza. Hey, these things happen. We apologize. We'll be back in a couple of weeks. know, bear with us, you know, but you can't let those times, you know, get you off track, you know, and you gotta believe in your product because those things will happen. Absolutely. we, we.
1000 % believe in our product. We know we have a good product. We know we provide outstanding customer service. You know, so those little mishaps that occur in any kind of business, you know, you just keep on trucking, you know, and learn from that, you know, and it gets you, it makes you better, you know, because you've gone through it. It's like, okay, I know how to tackle this now, you know, right, right. No, that resin, that resonates so much. feel like with furniture flipping early on, you know,
Jenny Dempsey (20:48.75)
I didn't know what I was doing. Sometimes I would literally go and like Google a YouTube video to figure out what type of like process I need to do for a particular piece of wood. And then I would do it and mess up and I'm like, my gosh. And I'm so glad that a lot of these things that I was, know, pieces of furniture were not clients yet. They were things that I was finding and trying to fix up and like, you someone was throwing away. I'm like, I'll do this. But I would sometimes knock myself down a bit, like I should have done better, but I would learn and move on and
I didn't have a journal. I love this journal idea, Ashley. I feel like that is something, I've been like, I have a notes app, so I just like type notes out, but it's like all kind of scattered around. Like I love the idea of having a journal, writing it with, you know, a pen on paper and having that so easily accessible. And I love how you mentioned a turn into scheduling and I'm sure it's evolved even more, you know, with the journals. Do you keep all of them as well? I'm sure you have multiple by now.
Cause I think that's a great tip for a lot of people when they're starting out to document these things and learn from them. so how does that kind of work where you're at now with documenting things, but also kind of going back and remembering things from, from the past and lessons you've learned. Well, we are, we're on our first year. So we're on our first journal. and the journal, it's the type of journal, it's a Fox journal, but there's,
Areas, so you've got your standard calendar squares, and then there's areas where you can write lengthy notes. And then we also have, we keep our, a lot of our collection of process, different pizza toppings, like combinations. We have that in there, our ranch recipe. So we're still on our first journal, but it's, getting pretty full as we go on.
If we're sitting on the couch and we come up with an idea or, you know, maybe we should try this. We'll write it down, you know, and, you know, go back to that. And it kind of just reminds us, you know, because yeah, everything's digital, but writing it down, really some instant you remember it. You remember that experience, you know, when she would make a dough or something was a little off, she'd write it down. Like, you know, it didn't puff up as much or.
Jenny Dempsey (23:12.77)
You know, didn't proof is good. You know, the water temperature is this. And I mean, it's just everything. Yeah. Every detail, you know, we jot down. I love that. I had, so that's so incredibly helpful. And I feel like a lot of people listening, that's something that's very actual. People can take away, to have something good and solid and to keep track of these things as you know, you kind of evolve. so I,
love pizza. love the style of pizza. guys make my boyfriend. I was mentioning before, like he loves to fire them up in our backyard for like family parties and stuff. And we're always learning. He's always, he does all of that. I just watch and eat. It's great. and so like you mentioned pizza topping combos and I, I'm, I'm so
What are some of your favorite ones? I've never heard biscuits and gravy pizza. I'm like blown away. That sounds amazing. But what other, if you can share some other of your favorites, just for a little pizza inspo, like what are some of your favorite ones or what are some of your favorites that you see people that come to you enjoy most? Well, my favorite or one of ours is the barbecue chicken pizza. And that was our
first specialty pizza that we put on our first menu, because we always have a specialty pizza on our new menu that we roll out right now once a month, but we're thinking about changing it up to like two weeks. But the barbecue chicken pizza is by far my favorite, but it's very popular where we took it off the menu and people were asking for it constantly.
And that's what just you barbecue the chicken. Well, Ash is leaving out something because barbecue chicken pizza is kind of a regular in Southern California. know, people are familiar with the California pizza kitchen and whatnot. But Ash, took it and made it incredible because she uses a very gourmet, creamy Gouda cheese. and that smoked Gouda.
Jenny Dempsey (25:27.052)
So that kicks up the flavor, but yeah, I, I barbecue the chicken in a barbecue rub. and then we put a, it's a spicy pepper, smoke pepper, seasoning on top of that as well. it just elevates the flavor, tenfold. so we pretty much sold out of that at, just about every event we, had, had a few folks that would come.
every single Friday at this brewery because they just wanted that barbecue chicken pizza. Another popular one was the jalapeno popper pizza. yeah, that was good. So it was a butter cream cheese base. So there's no red sauce on it. And then it's cheddar cheese and bacon and then thinly sliced jalapenos. And the way the base
Cooks with the art now it's just. It's heavenly. Yeah, yeah, yeah, I've had people stop me. And literally tap me on the shoulder that is the best pizza ever had my life. It was very unique. So yeah, like the pigly wiggly is that was actually a special that people begged us to keep on the menu.
So that's a regular, it's a meat lover. Italian sausage, bacon and pepperoni. Italian sausage we use is very high quality. It's delicious. I've had a lot of different Italian sausages growing up and, know, just being Italian and this sausage can be actually reached out to us. And they said, it looks like you use very, very fine ingredients and we would like to send you some samples.
So they sent us samples and I was blown away. I was like, this is the sausage. So, what about your favorite vegetarian pizza? I'm a vegetarian. So anything you got, cause I love the creativity with all the toppings. What do you, what do you got for us veggie friends? Well, so it's basically a mixture of peppers. You got your yellow, red, green.
Jenny Dempsey (27:44.224)
and mushrooms, but we take it a step further and we saute them in an Italian seasoning. And going back to that's how I grew up, was everything was mushrooms, you know, sauteed with a little bit of a spice kick. then also he grew up on a sausage, what pepper sandwich. And so we just omit sausage from that. And then the way the peppers are sauteed with the mushrooms is
I mean, melts with the cheese. She eats it for breakfast. She literally asked me weekly to make that. Yeah. But that's what I grew up with. was sauteed mushrooms, peppers, and egg on a sandwich. everybody thought it was weird, but I was so used to it. So I just took that kind of recipe from my dad, and that's what we use for the veggies.
Yum. Amen. That sounds amazing. my gosh. Well, thank you so much, know, Ashley, Tony for sharing your story or journey, where you came from, how you are now. I am starving. I am like craving pizza. Where can people find you? How can they connect with you and enjoy some of the za you got? The best way to find us is through Instagram. Ashley posts every Monday our schedule where we're going to be throughout the community. We're in
Chula Vista quite a bit, but we do do communities and events. We've done them in San Marcos, Escondido. We have a pretty decent following in the Chula Vista area. So that's typically where they can find us. But yeah, Ashley posts every Monday our schedule. It's Cuchina de Pizza. Thank you so much for your time and sharing all the delicious pizza. Yes. Awesome. It was a pleasure. Thank you.
Thanks for tuning in to this episode of The Career Flipper. Be sure to connect with Ashley and Tony, Kachina De Pizza, using the links in the show notes.
Jenny Dempsey (29:46.912)
If this episode gave you a little boost, share with a friend who can also use some inspiration. Or maybe needs a slice of pizza. Rating and reviewing the show helps more than you know, and hitting that subscribe button means you'll get more amazing flipping stories like Ashley and Tony's every Thursday. Your support helps me reach even more career flippers and those dreaming of making their own leap, spreading all the good vibes and motivation we all need on this journey. And if you're looking for a career flipping speaker for your events,
or the podcast or just drop a line and share your story, swing by thecareerflipper .com. I'd love to hear from you. What I love most about doing this podcast is the hope that it might inspire you to go after what you're dreaming of, even if it feels really scary right now. I know it's hard to take that first step when the fear of the unknown holds you back, but if I could ask one thing of you, it would be to tie your shoes, take a deep breath, and just start.
You never know where it might lead, and I believe you can achieve whatever you set your mind to. So keep on your path, my friend. What's the best that could happen? Talk to you next week.