Behind The Scenes: Dig on The Pitch

By Leigh Isaacson

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Dig - The Dog Person’s Dating App was selected by Gimlet Media to be featured on the hit podcast “The Pitch.” Here’s the behind the scenes look at how we were chosen to be featured. Click here to listen to the call-in competition episode published June 19, and listen to the full pitch episode published August 7 here.

It started on a 90-degrees, humid, New Orleans summer day two months ago when I was out walking my dog Penny listening to my favorite podcasts. The Pitch’s Josh Muccio announced they would be hosting their first call-in competition, so I blocked off an hour in my Google Calendar and set a reminder to call-in and pitch. Being one of the first to get through was important, I thought, so the producers and their selection team wouldn’t be tired and jaded after listening to hours of pitches. I later learned I was one of more than 200 people from around the world to attempt to get host Josh Muccio’s attention that day.

My first call-in attempt went straight to voicemail, but since I had dedicated the hour in my schedule to trying to connect, I called again. This time, the correct dial-tone rang back and the host of one of my favorite podcasts actually answered and I launched into my pitch filled with dog puns (I shih-tzu not), dating stories, and plans for our company, Dig.

It wasn’t 10 seconds into my pitch before I heard Josh Muccio and the producers laughing on the other end of the line. I had been in this situation before. People, especially dog-people, tend to fall in love with our company immediately when I share our story. Although the light heartedness makes for a fun pitch atmosphere, I have to bring people back into the mindset that this isn’t just a fun concept but a serious business opportunity. Josh seemed to get that right away.

“Well done, you just crushed it,” Josh said. “Ok, this is genius. Marrying pets and dating.”

If you listen back to that episode, you can practically hear my giant smile tearing across my face as I fan-girled out and told them how much I love the podcast. After I hung up, producer Heather Rogers also gave her stamp of approval with a, “cool. That was good.”

But that was just the beginning of a process that I only know how to describe by comparing it to online dating. First, there was a week of anxious waiting. Then, I jumped at the notification when Producer Heather sent her first email to me a week later. It would be the start of a few weeks worth of emails and phone calls filled with follow-up questions to see if I was a perfect match for the show. We discussed our customer acquisition strategy, defensibility, and one of the most popular questions on the show, “is this a business or just a feature?”

As an entrepreneur, I’m always ready with Dig’s facts, figures, and projections at all times. However, as a former TV reporter and journalism professor, I also knew that in this case - delivery was just as important as content.

I’ve been on dozens of podcasts to talk about Dig including NPR’s How I Built This (in the How You Built That segment), the Kim Komando Show, and famous Divorce Attorney Laura Wasser’s podcast Divorce Sucks! Each time, the producers remind you to be lively, speak clearly, and stay on topic. So, I knew The Pitch producer Heather wasn’t just looking for a great company to pitch investors on the show. She was, most likely, also looking for someone who could clearly articulate their mission, provide emotion, and, frankly, speak in soundbites. Knowing I was being recorded each time we spoke for potential use on the show, I tried to incorporate elements of timeliness and human interest in each answer I gave Heather while staying relatable to The Pitch audience and speaking in short, clear sentences. I tried to hit home with stories about the first Dig wedding, the hundreds of Dig users we’ve met at our launch events, and the adoptable dogs we feature on @digdates Instagram.

It worked!

On June 12, a month after my initial call to the show, I got a phone call from host Josh Muccio. I was sitting on the beach in Los Angeles, which sounds nice, but it was only because Southwest had lost my dog treat and pet bandana-filled luggage and I was waiting outside close to the airport with my backpack until I could check-in to my Airbnb.

On a recorded call, Josh said Dig - The Dog Person’s Dating App was selected to come pitch on the show in Brooklyn at Gimlet Studios! You can hear some of the phone call, including my bad dating app puns (“we matched!”) and my lofty promise to “kill it,” at the end of the call-in competition podcast episode.

I asked Josh why he picked Dig. Along with being very complimentary about the business, he said my pitch was fun, simple, and easy to understand. He thought my pizazz and spunk would be great in the pitch room, and it clearly seemed like I knew what I was doing.

Bingo!

I had two weeks to prepare, but as every entrepreneur knows, business doesn’t slow down just because you’re fundraising. Dig was launching with big, dog-friendly events and partnerships in Denver, Seattle, and Dallas, our user numbers were climbing higher thanks to our new ad campaigns, we were interviewing potential new hires, and of course much more. The pitch was scheduled for the day of our Denver launch event, so my co-founder and sister would be running the puppy-filled party without me. But, our small, dedicated team is always ready to take opportunities as they come. We knew the chance to pitch world-class investors and share our story would be well worth the work.

That’s when I discovered an unsung hero behind The Pitch, Lisa Muccio, and she guided me through the preparation and scheduling process. The Pitch team recommended I listen to and study as many of the past episodes as I could, and they also sent an uncut version of a previous episode so I could get a clear understanding of just how long I’ll be in the pitch room and how my pitch will be edited into a podcast episode.

In an email, Josh said, “Hopefully I'm not overwhelming you. I've just seen in the past that the founders that do the best, are the ones who prepare the most. And those who go back and study past episodes perform even better.”

Loud and clear!

I learned that I’d be pitching a few of the regular investors on the show and one investor who was new for this season. My first step was to go back and listen to the episodes that featured those investors and, importantly, to learn if any of the investors were dog owners or had invested in pet tech or dating apps before. By the time of the pitch, I was ready to offer investor Michael Hyatt’s dog Chiquita the position of Chief Dog Officer and was excited to connect with investor Charles Hudson of Precursor Ventures about his investment in dog-related businesses.

Two of my favorite previous episodes on the show, of course, were from dog-companies Waggit and DogSpot. Before my pitch, I took the opportunity to reach out to the founders who both quickly replied with great advice about staying focused in the room, how to work with the investors after the show, and emphasizing the importance of sharing our most compelling metrics up front (while also saving a few for the middle).

To start capitalizing on our airtime, I wrote up a quick press release and told the local press about Dig winning the global call-in competition and about our upcoming episode on The Pitch. The story was picked up by New Orleans magazines and TV stations, and from there it was reposted across news outlets such as the San Francisco Chronicle, KMBC Kansas, and even Yahoo News. This way, even if I walked out of the pitch room without investment, we were still getting a great boost just by being on the show. That was a comforting thought as I walked into the gorgeous Gimlet Media studios in Brooklyn on June 27.

I met Lisa Muccio at the front desk, and I tried peering into offices to see if I could spot any of my other favorite podcasters, like the guys on Reply All, as we walked back to the prep room. I was surprised at how light and airy the Gimlet building is compared to what I was used to in the dungeons of the local TV news world, and the atmosphere sent me to a next level of excitement. Lisa handed me water and an awesome The Pitch t-shirt to take home and got me mic’d up for the show.

I can’t wait for people to hear what happened next. What you won’t be able to see is the huge smiles the investors gave me when I walked in and they saw my Dig t-shirt, the affirming handshakes laden with anticipation, and the microphone on a stand that reminded me of the toothpaste commercial song “You’re never fully dressed without a smile” from the musical Annie.

After the pitch, I handed out “my mom’s single” and “my dad’s single” bandanas to everyone, and I sat outside in a community garden next to the studio and called nearly everyone I knew. I went to meet a friend at a bar, and wildly, the incredible day only got more glamorous.

While recanting The Pitch to my friend, we spotted Tyler Cameron, the dreamy and extremely popular contestant from this season of The Bachelorette. This was weeks before Tyler would make it to the finals, but he had already amassed 675K instagram followers of his now 1.9M and, importantly, I knew he was a dog-lover. I walked right up in my sweaty Dig t-shirt and told him about the app. He gave me a hug and laughed that he’d share Dig - The Dog Person’s Dating App with the single guys he knew - since he happened to be close to quite a few now. I told him I was in town to be on a show myself, actually, and that he should check out The Pitch. No word yet on if he subscribed.

Listen to the full pitch episode featuring Dig - The Dog Person’s Dating App here.