We recently connected with Kara Ricciardi and have shared our conversation below.

Hi Kara, thanks for joining us today. So let’s jump to your mission – what’s the backstory behind how you developed the mission that drives your brand?

Stretchy Pants Food Tours is passionate about using food to connect people and celebrate local culture and history. Our mission is to create immersive and authentic culinary experiences that showcase the unique flavors and stories of San Francisco (and future cities we may expand into!). We know that food has the power to bring people together, foster understanding, and create lasting memories.

Integral to our mission is promoting small businesses in our community and telling the untold stories of neighborhood entrepreneurs.

Kara, love having you share your insights with us. Before we ask you more questions, maybe you can take a moment to introduce yourself to our readers who might have missed our earlier conversations?

I was lucky to grow up in an Italian and Spanish family in Brooklyn where I learned alongside my grandparents, aunts and extended family and developed a love of cooking, signing up for cooking classes by the time I was 9 years old. I always knew that I wanted to go to culinary school, but my parents wanted me to go to University first. I’m glad I did because I met my friend Ruby there who is my business partner now. I worked at restaurants during college. And then worked as a Pastry Prep Chef at the famous Central Park Boathouse, which gave me the knowledge that I wanted to go further and I went to the French Culinary School in San Francisco. While attending culinary school at night, I also worked with Americore on a farm in Half Moon Bay, California helping kids learn how to cook farm to table meals. My culinary experiences and my innovative mindset led to opportunities at test kitchens where I was making everything from vegan cookies to the spice and seasoning blends that are probably in your pantry today.

While I enjoyed food product development, it was quite repetitive and featured ingredients that were a far cry from the farm-fresh produce and local ingredients I enjoyed with the kids on the farm. I know that I wanted to start a culinary business, so I decided to get an MBA in Global Entrepreneurial Management in a fantastic program that included semesters in San Francisco, Taiwan and Barcelona and students from each region learning together.

Throughout my whole life, often with Ruby, I have gotten to travel extensively. I’ve been to over 80 countries and territories and I always look for the best food in each city and where I can go to meet locals. Roby and I often took Food Tours and loved learning about culture and history while eating the foods most traditional and/or innovative for that city. While I had always thought about a catering business, I realized that offering interactive experiences like Food Tours and Tastings was most in line with my values and commitment. My food experience makes me uniquely qualified to craft local experiences because I know how to highlight the real culture of a place and also what travelers are looking for.

In 2017 I started Stretchy Pants Food Tours and Ruby joined as my business partner not long after. I love that Ruby and I get to use our business, travel and culinary expertise to raise awareness of how delicious, fun, accessible and innovative San Francisco’s food scene is. We take people to the historical neighborhoods of San Francisco and help them see beyond the current commercial landscape to see the thriving, diverse population that has always thrived here and collaborated.

In addition to strategizing together, Ruby is a lawyer and essential at helping us have smart, fair and easy to understand contracts that our private clients appreciate – in the last few years we regularly lead tours for teams and new hires from the biggest tech companies in the Bay Area.

Our tours are designed to provide an interactive and engaging way for people to discover local restaurants, markets, and hidden culinary gems. In addition to our Food Tours, which favor family run and independent businesses, we partner with local food artisans and chefs to create unique and memorable experiences that highlight the best of each city’s food scene.

How’d you build such a strong reputation within your market?

Like our name “Stretchy Pants” suggests, our tours are very authentic and fun – like our guides. Our guides get to show the city they love through their eyes. We take our time with training and making sure our guides are ready and empowered to offer a delicious and engaging experience every time, this has meant that we almost always earn 5 Star reviews on all our platforms and we first grew organically and built our reputation this way. Recently we won the Traveler’s Choice Award on Trip Advisor in 2023 and we have been getting additional awards as well.

Now we have a bustling business with three public tours offered every week and 5 private tour experiences that our Corporate clients and private groups love (often Birthday parties, schools, start-up teams and social clubs in San Francisco).
One thing that sets us apart is that we focus on family owned businesses and include many restaurants, bakeries and bars that are 50 – over 100 years old whenever possible. Our guides are also always looking out for high quality options in every area and sharing if they find a new fave – this is helpful in case our “usual” spot is closed. The guides stay in regular communications with me and each other to stay connected, troubleshoot and share helpful insights with each other.

How do you keep your team’s morale high?

Our team of tour guides are all unique and talented individuals who have a love for showing people around and sharing history and food. They know their baos from their bibimbap, and all have their favorite taco and dumpling spots, but more than that they know people and they love being around them. Almost all my team members approached me, and I’ve found that most people know if they have what it takes to be a tour guide. It’s a challenging job and not for everyone. So long as I trust my gut in the hiring process I have always found fantastic people who are naturals.

I try to train well in the beginning then stay hands off unless something goes wrong. I try to respect that the guide might know more history than me, and is the one on the ground, so their feedback is in real time. I allow autonomy so they can enjoy what they are doing.

My senior team members and I curated the tours with our preferred spots for food and drinks, and we share outlines of historical and cultural touchstones that will be interesting to include, but we also leave a lot of room for our tour guides to research a region’s history and tell the stories that feel most resonant and engaging to them, and they might pick their own favorite dessert spot or change up a route to enhance their storytelling – they know that I trust them and this allows them to feel like the brilliant creatives that they are.

It’s a solo job and so I also try to make sure the guides feel like they have a community to chat about their craft. I do team dinners once a quarter and have a group chat, so they can feel connected and have a place to bounce ideas off each other.

Contact Info:

• Website: www.stretchy-pants.com
• Instagram: @stretchypantsfoodtours
• Facebook: @stretchypantsfoodtours
• Linkedin: @stretchypantsfoodtours
• Youtube: @stretchypantsfoodtours
• Yelp: https://www.yelp.com/biz/stretchy-pants-food-tours-san-francisco

Image Credits
These are by the Stretchy Pants guides and all are available for free use by our team.