In the Room with Investor turned Founder, Naomi Shah

Claudia and Madison interview Naomi Shah, Founder of Meet Cute

Welcome back to The Room Podcast, Movers and Shakers Series.

Today we sit down with Naomi Shah, founder and CEO of Meet Cute. Meet Cute is an entertainment company with the largest library of scripted rom-coms in the world and biggest global creative network of writers, actors, and directors. Naomi wasn’t always set to be the queen of digital-first romantic comedies. She grew up in Portland watching her parents work together in leading a successful software company. She stayed on the west coast for undergrad, finding herself at Stanford where she majored in mechanical engineering. Through a twist of corporate recruiting, Naomi landed at Goldman Sachs on the trading floor before ultimately joining Union Square Ventures as a member of the investment team.

It was in USV’s own conference rooms, where the idea for Meet Cute was born and created. Today, Naomi is recognized by Forbes 30 under 30, and has raised funding from prominent investors, including USV, Lerer Hippeau and Advancit Capital in an effort to bring a 21st technology to the sector which was made popular by movies titled, You’ve Got Mail.

In today’s episode of The Room Podcast, we explore insights and themes such as turning an investment thesis into a company, the “girl boss” trope and what it means for founders, and the future of the romance genre. Let’s open the door.

Listen to the episode here on Apple Podcasts or here on Spotify.

Key Theme 1: Turning an investment thesis into a company

As a former investor herself, Naomi knew what venture capitalists were looking for when starting Meet Cute. In fact, she originated the idea within the four walls of Union Square Venture’s office. It was in the pursuit of a company that mirrored the mission of Meet Cute, that Meet Cute itself was born. Venture capitalists are often creating thesis about the future in real-time, and validating them against what they’re seeing in the market. In some circumstances, more often than you might think, an investor will get so enthusiastic and convicted about an idea happening they’ll build it themselves. Naomi’s first employer was the first person to say yes to here and Meet Cute which today has gone through their Series A venture financing!

Key Theme 2: The “girl boss” trope and what it means for founders

In the 2010s, the idea of the “girl boss” became popular nomenclature to describe a woman “killing it” at work. It was often women who were lauded for raising gobs of venture financing or building a successful business on their own. One by one, we’ve seen these former girl bosses be torn down by media some due to fraudulent and illegal activity, ala former poster child Elizabeth Homles. Others because of less nefarious, but still career-damaging decisions, such as Audrey Gelman and Ty Hanney.

Naomi, Claudia and Madison discuss the fallout of the girl boss in this decade, and what it means for founders who happen to be women. Naomi remarked, “The girl boss became a really big trope in a really big archetype, which is awesome…but it put a lot. emphasis on the girl and not the boss. There are so many different styles of leadership. Some leaders are quiet, some leaders are louder, and some leaders are persuasive.” Embedded in this quote and the discussion is a challenge to the venture and start-up ecosystem to value grit, individuality, and excellence rather than identity in isolation from the output.

A question for our listeners, how do you reconcile your identity with your work? And how does this reconciliation impact your definition of success?

Key Theme 3: The Future of (digital-first) Romance

On a lighter note, we looked backward at the evolution of the romantic comedy genre and lept into the future with Naomi and Meet Cute to hear what the future holds. Today the entertainment industry is empowered with more data than ever on viewers and user engagement. However, there is still a lack of scalable real-time feedback on which storylines will stick, and which will fall flat. Naomi and the Meet Cute team aim to change the status quo through their rom-com incubation efforts and help the large Hollywood studios produce content that already has a loyal audience. Naomi shared Meet Cute closed its first TV deal in February, bringing one of their stories big screen. We can’t wait to tune in!

Thank you for listening to this episode of The Room — if you enjoyed our conversation please like, follow, and subscribe to our newsletter. Which you can find at

Stream this episode on Apple Podcasts

This episode concludes our second installment of Movers and Shakers.

Get excited about season six, launching Tuesday, May 18th, as 10AM EST or 7AM PST.

See you in The Room.




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