How Dating App Left Field Scored Spot on ‘Shark Tank,’ Got Investment

Kate Sieler and Samantha Martin had a secret.

For several months, the cofounders of dating app Left Field had to keep their lips sealed about pitching their startup on the hit show “Shark Tank.”

“It was definitely a crazy secret to be sitting on for so long, especially because there’s no guarantee that the episode is going to air,” Sieler told Business Insider.

The pair’s “Shark Tank” experience began with an unexpected email from a producer — which they initially thought was spam — and included months of video calls before they flew to Los Angeles to pitch on camera.

On set, the two were “laser focused,” Sieler said. Adrenaline was pumping.

The episode, which aired this month, featured two guest “Sharks” on the panel of investors: Reddit cofounder Alexis Ohanian and jewelry designer Kendra Scott.

“Hi Sharks,” Sieler said as the two walked up to the investors. “We’re best friends, and we’re here seeking $200,000 for 5% of our company.”

They ended up with an investment from both Ohanian and Scott.

The pitch that got the Sharks on board

Left Field isn’t the first dating app to end up on Shark Tank. Dating app Coffee Meets Bagel went on the show in 2015, for example.

“We watched every episode on a dating app,” Martin said. “We did our homework.”

Left Field’s pitch was straightforward: The dating apps we’re used to aren’t cutting it. Sieler and Martin tried to prove that their app would be different and help people find love in real life, not just swipe.

At the time, Left Field was focused on location-based dating, though it’s since pivoted to matching people based on shared interests and communities.

While pitching, the founders highlighted the app’s early 5,000 users (that number has since grown, Sieler said, but the startup declined to share an updated number). They also answered questions about how they’d monetize (their plan is to introduce subscriptions down the line).

Knowing ahead of time that Ohanian and Scott would be Sharks in their episode, Sieler and Martin focused their pitch on winning them over.

“We had come in dreaming that maybe one of them would invest,” Sieler said.

To woo Ohanian, they zeroed in on how they’d deliver a better alternative to online dating for younger daters. For Scott, that meant focusing on having strong branding, Sieler said.

“I know nothing about apps, nothing, but I know I have a lot of women in my company who are struggling every day to meet their man,” Scott said after hearing Left Field’s pitch. “So many of them are single in my business, and they hate the current dating apps. So I like that this is a fresh approach.”

After some on-screen banter and negotiations, Left Field’s founders convinced Ohanian and Scott to invest $200,000 for a combined 8% equity stake with a post-money valuation of $2.5 million.

The deal also gave Ohanian and Scott advisory shares worth 4% combined, split evenly between them, for their advice and resources.

“They’re very compelling founders,” Ohanian said during the episode. “The numbers are early, early signs of potential traction, and I do think Gen Z desperately wants to find human interaction again.”

Ohanian’s investment went through his VC fund 776, which has also invested in new social startups like Airbuds, a music-sharing app. Scott invested as an angel.

It’s an uphill battle for many dating apps, however, as giants like Bumble and Match Group (which owns Tinder and Hinge) face headwinds in the stock market.

‘I was so nervous that I couldn’t eat’

Pitching investors generally comes with stress — but cameras, lights, and the chance to be watched by millions added to that pressure.

“I was so nervous that I couldn’t eat,” Sieler recalled from the day the two filmed the episode.

“We spent a lot of time just in our dressing room reciting our pitch to each other, asking questions,” Martin said.

Walking out onto the set, the two wore green tank tops with Left Field’s logo they’d hand-dyed in a bucket themselves.

“You have to get your outfits approved, and they work with you to make sure it’s going to be good on camera,” Sieler said.

Before seeing the episode for themselves when it aired, Left Field’s founders didn’t know what would be cut from their pitch. The pitch, which is edited down to a roughly 10-minute segment for the show, took about 45 minutes in reality, Sieler said.

Onstage, you have “no concept of time,” she added.

Bringing capital — and lessons — back to New York

When Sieler and Martin arrived back in New York City after filming, they polled Left Field’s users about what was and what wasn’t working.

Sieler said the “No. 1 thing” the app’s users reported was that they liked how Left Field made them feel like their next love was “already a degree of connection away.”

As Martin described it, there was a clear “nostalgia for the meet-cute.”

Since launching and pitching the app on “Shark Tank,” Left Field has pivoted away from its location-based features to connecting people based on shared interests and commonalities, such as mutual friends, hometowns, or favorite spots. The app uses AI to help calculate people’s compatibility.

Some of the app’s redesign direction stemmed from Ohanian’s perspective and 776’s other portfolio companies, Martin said.

“One of the most interesting lessons from Alexis is how you want to make it as easy for there to be content on a platform as possible,” Martin said. “We want it to be as easy as possible for people to interact.”

Riding the wave of attention after “Shark Tank,” Left Field is expanding into new US cities, starting with Boston.

Left Field recently made its first hire beyond its founding team, which includes a third cofounder, Sean Miller, and is preparing to raise its seed investment round.

“We’re really trying to stay small,” Martin said. “We are only trying to take the money that we need, so we keep control.”