In Conversation with Jessica Yergin and Christie Catan of Tails of Connection

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Describe your business in a few words?

Tails of Connection is an online dog training community.

What made you take the leap to start your own business?

Jess: Christie and I met through Instagram after I fell in love with Christie’s 80-pound dog @otis_unleashed and we became friends IRL even though I lived in NYC and Christie in DC. When I came to DC for a job interview in the spring of 2019, we met up for coffee, and Christie shared her idea to build a new kind of resource for dog parents centered on community. She recounted her struggles trying to help her giant dog, who was still terrified of feathers, despite having spent thousands on training. When I got back to NYC, I called Christie back and said, “What if the job I was interviewing for was actually to start this company with you?” In August 2019, I moved to DC, and TOC was born.

What was your background prior to starting your own business?

Jess: I spent most of my career in TV news, working first for ABC News in breaking news and live coverage of special events like the royal wedding and then for Erin Burnett at CNN. Before I started TOC, I was a director of digital content at Charter Communications where I ran all of their pr team’s external digital properties, including their websites and social handles. As part of that role, I led the content strategy and creation for those platforms. 

Christie: I worked as a consultant at Ernst & Young for over 5 years and left to build my own startup in the fitness space. I had to close that startup down, but it is hard to call it a failure when I learned so much from it. 

Did you always know you wanted to be an entrepreneur?

Jess: Not at all. Growing up I knew that my dad’s family had a women’s coat and suit business that ultimately split the family apart for years. That kind of risk that could permanently impact your personal life really scared me. I guess that’s why I’m not doing this with family!

Christie: No, definitely not. I actually thought I wanted to be a doctor when I went to college, but I had a lot of health issues that landed me deep in the medical system. I spent a lot of time in hospitals and really wanted to not have to think about health, so I changed majors. 

Take us back to when you first launched your business, what was your marketing strategy to get the word out and did it go as planned?

Jess: We were lucky because Christie’s dog, Otis, has an incredible community of over 200k followers on instagram. This community has watched her work with Otis and her other rescue dog, Sully, all along and when we launched TOC they were very supportive. For instance, we asked them to fill out a survey about life with their dogs and overnight over 1k detailed responses flooded our inbox. 

Christie: We have always prioritized organic growth. We worked hard to build a small community and add value to their lives. As we focused on that, they started sharing us with their friends. It has been important for us to cultivate an engaged community and not just try to get the biggest reach.

We always learn the most from our mistakes, share a time with us that you made a mistake or had a challenging time in business and what you learned from it?

Jess: Running an online community is incredibly rewarding. We learn so much from our #TOCFam. Over the course of last year we’ve had a few scary moments where a couple of community members sent us threats directed at us or at themselves. We took these very seriously and reported them to the appropriate authorities.

Christie: I feel like my previous startup was a giant learning experience. You name a mistake, I likely made it. I think my biggest mistake in my previous startup was in focusing too much on the idea and then building my grand vision and not enough on actually doing, iterating, and learning. With TOC, we started really small and tried to thrill one person. We learned from that person and the people they told, and it informed the next thing we did. We keep an eye on the vision, but we try not to let our vision get in the way of our execution. 

What is the accomplishment you are the most proud of to date?

Jess: We’ve bootstrapped the entire time and in 2020 (including during the pandemic) we launched two community-based, on demand video e-courses, where you can train your dog at home. We built and marketed both courses entirely on our own. So far we’ve had over one thousand paying customers in our first year.

Christie: I am proud of us for building a community that has a beating heart. This world can be a really tough place, so I feel really excited knowing that we have created a space people feel some connection in.

When hiring for your team, what is your go-to interview question? Please share any hiring tips you can share from your experience?

Jess: We haven’t had the opportunity to hire yet. I can’t wait for that. In tv news years ago there was a question that I always found fascinating. “It’s five minutes until the Today Show starts and the co-anchors are fighting. What will you do to convince them to come to the set and do the live show?”

How has your business or industry been impacted by the COVID-19 pandemic?

Jess: The pandemic was particularly challenging because we needed to quarantine and were separated. Christie had to film herself in her apartment for our next product, Camp TOC, and upload the footage for me to edit. Overall though the dog industry is booming but dog trainers have been forced to do much more online business because of the pandemic. Christie and I were fortunate to have a digital product, the Tails of Connection Challenge, already available right when the pandemic started so we didn’t have to scramble from that perspective.  

Christie: We have done a lot of growing in a time where the world has felt incredibly uncertain. So much is already unknown with startups, and it became tough for us to predict the future. Luckily our strategy pre-pandemic was digital first and we are small and able to adjust quickly, but it certainly created some extra question marks as we thought about our strategy. 

What’s next for your business? What can we expect to see over the next few years?

Jess: We are excited to partner with a professional trainer this year and design a course around her. In the future we would love to develop content featuring many more diverse training personalities. We are also releasing something puppy specific this year since there have been so many pandemic pups.

What is the biggest lesson you have learned in 2020?

Jess: A day that you are healthy and have food and a roof over your head is a great day. 

Christie: The little things are the big things.

What do you know now that you wish you knew when you were first starting your business?

Jess: It sounds cliche but it’s about the journey and not the destination. There are a lot of days where it feels like nothing is happening but now I know I have the power in me to change the direction of this business and make something happen and doing a little of that every day really adds up. 

Christie: It is really hard and will challenge every belief you have about yourself. I likely would have had some mantras taped above my desk to help ground me from day one – ha! 

How have you managed to stay grounded this year?

Jess: I raised a brand new puppy this year that I picked up in March (the timing was scheduled well before the pandemic and coincidental). He had a number of health issues from the beginning and is extremely high energy. Training and caring for him has been all consuming. For the first time I really got to appreciate being a part of our #TOCFam and using our products to learn and get help and advice from our amazing community. 

Christie: Trees! I fell madly in love with trees. I try to spend time in nature each day — often walking through the woods with my dogs. I stop and sit with trees and feel this calm just wash over me. 

Do you believe in work/life balance? What are some of your best tips?

Jess: I’m trying to. Especially with the pandemic and working in the same house as my husband all day long. I try to give myself breaks to play and train my puppy, Stanley. I also take time for myself to read (I really enjoy a good romance novel), work out (Christie and I have been doing Obe’ well before the pandemic and know and admire their kickass co-founder, Ashley Mills), and cook.

Christie: I hear so many different terms thrown around these days and am never sure what people actually mean by them without asking. I will tell you where I stand right now though. I think it is so important to remember our humanity. Work can often be a beautiful part of that, but it is not the only thing. I try to remember that I have all sorts of currencies — things that fill me up and add value to my life. Money isn’t the only type of currency. I value time with my dogs and friends and family. I love deep heart conversations. I love time in nature. I love dancing. Those things are also worth my time. I also find that I can be so much more creative at work when I give myself space to play and be. Like life, I think work has seasons. I think there are periods where it takes up a huge amount of time, and that is okay. In those seasons, I sometimes carve out just 10 minutes and give myself permission to do whatever the heck I want. Also, the busier work gets, the more important it is for me to spend some time in nature playing with my dogs, so I usually do that first thing in the morning to make sure I have filled my cup up before I get going with work.

What’s something our audience would be surprised to learn about you?

Jess: When I started college in New York, I wanted to be a professional flute player and I was in a joint program with the Manhattan School of Music. 

Christie: As a child, I used to have recurring dreams (over years) that I lived with dolphins (I have always loved dolphins). That is likely not what you had in mind, but it would at the very least surprise some people. 

What are your top 3 tips to stay productive each day?

Jess: 

Make a checklist in the morning and start checking things off.

Disable alerts from instagram on your phone.

Set mini goals for the day and reward yourself with a walk, a workout, a snack or something else when you hit those goals. 

Christie: 

Put your phone away from you or turn it on airplane mode when you want to work something out. 

Have a mini goal that is concrete and focuses your day a bit. 

Step away from what you are doing if you are just spinning. 

What does being an Entreprenista mean to you?

Jess: I feel so lucky to be a female founder of a small business. We still have a ways to go before we shatter that glass ceiling and I want to support as many female entrepreneurs as possible on this journey. 

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