We were lucky to catch up with Hillary Lake recently and have shared our conversation below.

Hillary, thanks for joining us, excited to have you contributing your stories and insights. What did your parents do right and how has that impacted you in your life and career?

My parents have impacted my life and career 100% My parents grew up in the hippy era and were somewhat free spirits and didn’t give myself and my brothers a lot of direction or expectations, so the possibilities were endless. My dad was a truck driver and he worked long hours and was away from home a lot, he mostly came home on weekends. My mom was a stay at home mom raising five kids. They didn’t run some big successful company but they had grit, were resourceful and worked together to make sure we had a home and home cooked dinner on the table. Mom usually made dinner during the week and Dad would cook on the weekends. He would make really big breakfasts, grill out and sometimes make gumbo or chili. Growing up in a home where most everything was made from scratch taught me how to cook like that. There was a love in the process from a young age. I loved watching dad stir the roux. My parents are also responsible for my birth order, The age old argument whether leaders are born or made was solved when I was born, the only girl and eldest of five. I was given the opportunity to babysit a lot growing up and my parents would pay me and also gave me an allowance so at a very young age, I learned not just the value of a dollar but also the value of working to make my own money. I also learned that I could say no when I didn’t want to and make my own hours. There was an entrepreneurial spirit in that.

Hillary, before we move on to more of these sorts of questions, can you take some time to bring our readers up to speed on you and what you do?

I have officially been in food service since I was fourteen, my first job was at Dunkin Donuts. I have been in and out of the food and beverage industry for most of my life. I opened a bar and grill in Chicago in 2013 with my husband and operated that until 2018 when I moved to Florida to care for my father who had Parkinson’s. While in Florida, I decided to start an event planning and catering company to support myself while I took care of dad.
While I was caring for my dad, my husband would visit from Chicago and bring me my favorite deep dish pizzas.
Enter the pandemic and I was not catering or planning any events and no one was flying to bring me pizzas.
This was a time to be really creative. So I started experimenting with recipes and pans for deep dish pizzas that tasted like home. and then I put it up on my social media. People were asking how they can get one, so I sold my first pizza.

Hillary’s Chicago Pizza is different because it is authentic. We are Chicagoans, born and bred and have eaten at a lot of our hometown OG pizzerias. I made sure to incorporate the elements that are tried and true to Chicago pizza like crunchy, cornmeal crust, zesty sauce and fennel in the crumbled sausage. We use fresh ingredients and make everything from scratch. I have done the R+D for gluten free and vegan deep dish pizzas. We don’t buy a premade crust, again everything is made in house. We use a local sausage company and that is made with his grandpa’s recipe.
We are a family business. My kids are working with us now as we have grown. My son just moved to Florida to be a part of the company and you will find my daughter in the front of the house.
We value the experience of eating together and food that tastes good and makes you feel good. We are offering a taste of home to a lot of MIdwesterners and Chicagoans who have relocated. We see the joy when they find us and have a sample. There may have been tears on one occasion. Our pizzas are deep and full, they are meant to be shared. We have had people say “this is the best pizza I’ve ever had.”

Can you talk to us about how your side-hustle turned into something more.

In February 2021 as things were working toward normal in the world, I took a job at a school and kept pizza as my side hustle. We were doing a pick up pop up at a tap room and one of the market vendors asked why don’t we try the farmers market. So my husband and I incorporated farmer’s markets into our weekends. We would make pizza after work on Friday night and get up early Saturdays and package the pizzas and load up to set up at the market. By March of 2022 we were doing three markets a month and our personal deliveries. We saw we really had something viable. I was bringing in as much as my weekly paycheck in 13 hours of work. My contract at the school ended in June and we decided to go full time into the pizza business. We entered a partnership with a new brewery, Myrtle Avenue Brewing that opened in August. They take care of the beverages and we serve hot pizza and offer pick up 2 days a week. We immediately grew 525% the month we went full time and that was in July, in Florida. I keep a vision board above my desk and have monthly sales targets on the calendar. Vision is nothing without goals. Focus and perseverance make dreams come true. Our next step is our own production kitchen and storefront. We are moving really fast. We can’t wait.

How did you put together the initial capital you needed to start your business?

Funding is such a tricky topic. People, including myself have all these crazy money stories. We were taught talking about money is taboo. Well, you can’t have a business without talking about money. Money is not evil, rich people aren’t all bad and living in a capitalist society is what we do so we have to play the game. One thing that lights me up about business is the fact that I get to employ people and enrich their lives. So when looking for funding or creating a funding pitch, I keep that in the forefront of my mindset. I am connecting people with opportunities. It’s a win win win. I have had to seek out funding with previous businesses and it is usually a combination of friends and family, microloans, and owner financing.
This business has been bootstrapped so far. “Bootstrapping is the process of building a business from scratch without attracting investment or with minimal external capital. It is a way to finance small businesses by purchasing and using resources at the owner’s expense, without sharing equity or borrowing huge sums of money from banks.”
I am in this growth phase now where I am going to need some capital for my next move and I am doing a combination of friends and family and a Kickstarter model. I plan on preselling gift certificates, selling pizza packages, and selling some more. For new businesses, the reality of getting bank loans or SBA loans is still very difficult.
I am excited to try the Kickstarter model, as a supporter of Kickstarter campaigns in the past, it makes you feel good and like you’re a part of the story. I hope to incorporate that kind of support and community building into the next round of funding for Hilary’s Chicago Pizza.

Contact Info:

• Website: https://hillaryschicagopizza.com/
• Instagram: hillaryschicagopizza
• Facebook: https://www.facebook.com/hillaryschicagopizza

Image Credits
NIck Hogan