Leigh Isaacson of Dig: “I think it’s extraordinarily important that we re-empower our local news reporters; I would love to inspire a movement where people were re engaged with their local news”

Alexandra Spirer
Nov 7, 2019 · 12 min read

I think it’s extraordinarily important that we re-empower our local news reporters. In New Orleans, where Dig is based, a longstanding local newspaper was recently bought out by a rival, and the reporters are being let go. This is unfortunately a common story among newspapers and traditional media nationwide. I would love to inspire a movement where people were re engaged with their local news. Reporters and local news teams are underpaid, overworked, and unbelievably rushed. However, they are the champions of their communities. We should be able to trust that the local news reporters are covering our stories to the best of their abilities, and offer them help when possible. There’s a lack of trust that reporters will cover businesses fairly or factually, but this could be easily solved with efforts towards better communications and by strengthening opportunities for relationships. I talk to small businesses regularly about the power local news has for their businesses. Understanding what is newsworthy and important for a community to know is not only vital for democracy, but it’s also a huge opportunity for local businesses to get the word out and position themselves as an expert in a field. Learning the difference between trying to advertise your business and a great news pitch can help a reporter cover an important trend with you included. A movement that fosters better relationships between newsrooms, local businesses, and stakeholders would be beneficial for everyone.


I had the pleasure to interview Leigh Isaacson. Leigh is the CEO and Co-Founder of Dig — The Dog Person’s Dating App. Dig is the best way for dog lovers to find a compatible match and plan a dog-friendly date. Leigh’s background in TV news reporting, homeland security studies, and nonprofit management helped form the way Dig celebrates the passion and commitment of dog lovers through the Dig app with dog-friendly events nationwide and by building a dedicated community of single dog-lovers. Leigh lives in New Orleans, LA with her German Shorthaired Pointer Penny and fiancé Adam.


Thank you so much for doing this with us Leigh! Can you tell us a story about what brought you to this specific career path?

background is in TV News reporting. I taught at Tulane University, where my classes focused on Homeland Security and Emergency Response Management. I was also the regional director of a large nonprofit in coastal conservation in Louisiana. The one thing everything has in common is that there are dog people everywhere! A few years ago, my sister, Casey, was dating someone who tried to be a dog person for her. By the end of the relationship, he didn’t want the dog in his apartment or he’d put towels down on the couch so the dog didn’t touch anything. She said to me, ‘I wish I just knew from the start that this wasn’t going to work because of my dog.’ Together, we knew that we could solve this problem. With Casey’s incredible background in art direction and advertising design, and my various management and communications careers, we could design a great app that would connect dog people. From there, we could get the word out in really unique, fun, dog-friendly ways. I’ve always been extraordinarily curious, which was very important as a reporter. It’s equally as important when running a business. You have to be interested, willing, and passionate enough to learn every aspect of getting a company off the ground.

Can you share the most interesting story that happened to you since you began leading your company?

Being so immersed in the dog-loving world, it can be easy to forget there are people out there who truly hate animals. I was pitching to a group of potential investors, and one man said that his father told him he could only have a pet if it could be held underwater for 45 seconds and survive (which is why, he said, they only had goldfish). The man was proud to say he would never let an animal in his home (and therefore had no idea why people would want to be on a dating app devoted to dog lovers). Luckily, we are constantly surrounded by incredible people who dedicate their lives to loving their dogs and rescuing others. That one man’s negativity was quickly washed out by a sea of dog-loving partners and Dig users.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

Early in the app’s infancy, my sister Casey, who is my co-founder, and I waited in line outside of the Flatiron Building in New York City where we intended to pitch Dig for an investment-oriented web-series. We brought Casey’s dog, Layla, to pitch along with us because she was the inspiration for the app and she’s adorable. Layla is often with us for events, on travel trips, and in business meetings. However, we hadn’t considered how Layla’s irrational fear of reflections and shadows would be exacerbated with TV cameras and lights highlighting our pitch. After lots of preparation and hours of waiting in the freezing cold, we ended up giving our quick pitch while Layla squealed and shook in our arms. We probably looked more like a PSA about canine anxiety rather than a dating app for dog lovers. We learned an important lesson on the importance of cutting to the chase and limiting distractions. Although Layla is important, the quality of our business, our passionate community, and our unique marketing efforts shine on their own.

What do you think makes your company stand out? Can you share a story?

Dig is unique because it brings dogs to the dating world and it brings another side of companionship to the dog world. In both industries, people are looking for better out-of-home experiences. One of my favorite e-mails I’ve received is from someone who on a Dig date said that it seemed like the dogs fell in love first, and that it almost gave them permission to let their walls down and connect with the person on the date more easily. We’re building a community of people who are looking for compassionate, trustworthy, and responsible partners. The dog aspect of the app brings out the best in people right away.

Are you working on any exciting new projects now? How do you think that will help people?

We are constantly talking to our users about what they want to see from the app. How to make it better, where they want more dog-friendly events for singles, and more. We have a few exciting, new features coming soon that will help users enhance their profiles and put their best foot, and paw, forward. We’re also expanding our brand ambassador program nationwide. We have users, dog groups, rescues, and dog-friendly businesses reach out to us daily asking how they can help throw a Dig event in their area. Interestingly, almost all of the people reaching out to work with Dig are women. We’re emboldened to have such a passionate community of Dig fans that they’re willing to put in the work to help Dig succeed. These hyper-local events run by brand ambassadors will be taking place across the country, and it’ll help our users find love by getting more potential matches on Dig.

What advice would you give to other female leaders to help their team to thrive?

Very quickly, I noticed we were attracting employees and ambassadors to Dig who were almost overwhelmingly passionate about the dating app and dogs in general. One of the best things we did from the beginning was create a very flexible program that continues to harness their enthusiasm in unique ways, keeping everyone excited and passionate about their work. Finding out what they like to do in their spare time helps us think of new and creative ways to reach different dog-loving communities, and the ambassador gets to work in an area they already love. For example, one brand ambassador said they’re still into Pokémon Go, and they mentioned that tons of people bring their dogs to Pokémon Go events or meet ups. With their help, we were able to organize a Dig presence at an upcoming Pokémon event and so we can spread the word quickly in a new, hyperlocal, unique, and exciting way. I think, when given the opportunity, you can’t rival the passion and commitment of ambitious, dog-loving women.

What advice would you give to other female leaders about the best way to manage a large team?

Not only is our team large, it’s diverse. It’s made up of all remote workers, many part-time or commission-based representatives, an overseas development team, and more. Staying on top of weekly all-manager communications across departments is extraordinarily important. Not to mention, it can get challenging with many different time zones. If timing doesn’t work out for a video call one week, an email round-up of what everyone is focused on can be motivating and inspirational. For the rest of the staff, it’s important that they don’t have too many bosses. In a startup environment, it can be a delicate balance between wearing many hats and staying in your lane. Fostering great informal communications between groups with private Facebook groups, Slack channels, etc. is very valuable, but it’s crucial that there’s a delegation protocol led by managers who are empowered by the top team.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

Allison Ward is the CEO and Founder of Pet Krewe (Check out their dog costumes, they are amazing. They even have a notorious RBG — Ruth Bader Ginsberg- outfit). She has a remarkable pet-focused business also based in New Orleans and was instrumental in helping us break into the pet industry. She has introduced us to influential players in the pet industry, shared information about Dig with her customers nationwide in social media marketing and in her email newsletters, and overall acted as our champion in the New Orleans business community.

How have you used your success to bring goodness to the world?

From the beginning, we recognized that we were creating a platform for people to find love, but we also had an opportunity to promote dogs looking for “the one” as well. It’s been part of our mission to promote as many adoptable dogs as possible through the app, in our marketing, and at our events. Every dog featured in @digdates photos on Instagram and in our marketing materials is available for adoption from Louisiana area shelters. Also, at every event we host, we offer free space to any nonprofit or rescue dedicated to dogs, and we create a safe space for volunteers and fosters to bring adoptable dogs to our events. This way, we’re hoping to bring goodness to the world in the form of love between Dig users as well as love for animals who are in need.

What are your “5 Leadership Lessons I Learned From My Experience” and why. (Please share a story or example for each.)

  1. Gather as much advice as you’re comfortable with, but don’t take too much advice. It’s incredibly important to surround yourself with people who will give you mentorship and counsel, but make sure you follow through with only the advice that aligns with your gut and convictions. For example, we are regularly asked why we don’t have an app for friends to meet up at the dog park. We know that although the desire is there and we can gather information to be able to harness that enthusiasm in the future, we can’t stretch ourselves too thin while we’re still building a community dedicated to single dog lovers looking for a (human) partner.
  2. Be authentic. Early on, we made a decision that I would be the face of Dig on TV for news features and other public speaking opportunities. One way I remain personable and cut down on canned responses is by including my dog Penny in as many opportunities as possible. Unlike me, she definitely has never had TV training. She keeps me on my toes, keeps me laughing, and helps us focus on our main message of love and compatibility.
  3. Keep learning. Find a way to keep engaged with new trends, techniques, stories, and relationships. I suggest podcasts such as “Stuff You Should Know” and NPR’s “How I Built This” because they aggregate different topics and lessons you may not have known you were interested in.
  4. Get creative. I strongly rely on my sister and co-founder, Casey, who has a background in advertising design and art direction, to encourage the creativity in our marketing techniques, partnership ideas, and more. One of my favorite ideas Casey came up with early on in our business was to make dog tags out of Shrinky Dinks that said “my dad’s single” and “my mom’s single” to hand out to people who downloaded Dig. The low cost tags were easy to make, a relaxing activity, and a huge hit among Dig fans!
  5. Sometimes you just need to take a walk (with your dog). Growing a business is filled with daily ups and downs. Taking the time to literally step away from a complicated problem for a short while also getting some fresh air, exercise, and some alone time with your “pupner in crime” can reenergize you.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. :-)

I think it’s extraordinarily important that we re-empower our local news reporters. In New Orleans, where Dig is based, a longstanding local newspaper was recently bought out by a rival, and the reporters are being let go. This is unfortunately a common story among newspapers and traditional media nationwide. I would love to inspire a movement where people were reengaged with their local news. Reporters and local news teams are underpaid, overworked, and unbelievably rushed. However, they are the champions of their communities. We should be able to trust that the local news reporters are covering our stories to the best of their abilities, and offer them help when possible. There’s a lack of trust that reporters will cover businesses fairly or factually, but this could be easily solved with efforts towards better communications and by strengthening opportunities for relationships.

I talk to small businesses regularly about the power local news has for their businesses. Understanding what is newsworthy and important for a community to know is not only vital for democracy, but it’s also a huge opportunity for local businesses to get the word out and position themselves as an expert in a field. Learning the difference between trying to advertise your business and a great news pitch can help a reporter cover an important trend with you included. A movement that fosters better relationships between newsrooms, local businesses, and stakeholders would be beneficial for everyone.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

In the newsroom, I’d constantly be asked, “Did your story come out good?” It is an important question because the answer would dictate where producers would place your story in the newscast. I once worked with an extraordinarily talented videographer who used to answer the daily question with, “It’s better than good. It’s done.” It’s a lesson I remind myself of regularly. A phenomenal project that is only half-finished is less valuable than one that is completed! Sometimes it’s important to put just the right amount of effort into something to ensure it’s completed appropriately rather than agonize over its perfection.

Some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them :-)

Through Dig’s events and constant communication with Dig Dating App users, we’re on the ground meeting and engaging with dog lovers in cities across the country. We understand what dog lovers are looking for in terms of new experiences, and we hear their points such as: How difficult it is to travel with your dog, how many apartments are not dog-friendly, and more. We would like to sit down with those who have a major influence in the pet industry to discuss the future of dog-friendliness and how trends in the industry will help us ensure we live healthier, longer, and more joyous lives together with our pets. I’d like to have breakfast (at a dog-friendly location!) with Nina Leigh Krueger, President of Nestlé Purina U.S. PetCare, who has decades of experience in the pet industry including innovative new product rollouts, marketing, and M&A. Based on her experience and public remarks, I would be excited to learn Nina’s perspective on the dynamic changes happening in the pet industry today. I also have to mention my sister’s idol, Tina Fey, as a powerful, funny, inspirational boss who could teach us about hiring the right people (and ‘getting out of their way’) as she discusses in her book Bossypants.

Authority Magazine

Leadership Lessons from Authorities in Business, Film, Sports and Tech. Authority Mag is devoted primarily to sharing interesting feature interviews of people who are authorities in their industry. We use interviews to draw out stories that are both empowering and actionable.

Alexandra Spirer

Written by

I am an entrepreneur, publicist, journalist and event producer based in Sunny Florida. My passion is writing & giving back to others.

Authority Magazine

Leadership Lessons from Authorities in Business, Film, Sports and Tech. Authority Mag is devoted primarily to sharing interesting feature interviews of people who are authorities in their industry. We use interviews to draw out stories that are both empowering and actionable.

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