Ep 34 | Prerna Gupta

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Forget the Naysayers

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Prerna Gupta is a serial entrepreneur and investor. After being at the helm of many successful startups, Prerna is now the CEO and Founder of Hooked, a company that is redefining fiction for the Snapchat generation. Hooked has over 100 million viewers across social media, a short form video streaming app called Hooked TV, and has received funding from Ashton Kutcher, Mariah Carey, LeBron James and Jamie Foxx to name a few. 

As the child of Indian immigrants growing up in a conservative town in Oklahoma, Prerna spent much of her life pretending to be someone she was not. Through soul-searching and digging deep within herself, she grew to understand that her differences made her special and that if she stayed true to herself, she would always be happy. Prerna has carried this lesson with her throughout her life: the courage to be herself has made her a risk-taking, brave entrepreneur, even when others have doubted her.

We chat with Prerna about her start-up lessons and failures, the importance of failing and iterating in business, the downfalls of being solely goal-driven, and why you should constantly seek fulfillment in life versus deferring your happiness to some time in the future. Prerna also shares more about her and her husband’s decision to buy a one-way ticket to Costa Rica, thoughts on staying balanced, and why love will always be more important than wealth.


Show Notes:

  • The impact that growing up in a small town in Oklahoma had on Prerna. [2:52]

  • Prerna’s career after college, before she decided to strike out on her own. [6:35]

  • Prerna’s feelings about going down a different path to most of her friends who were in the corporate world. [10:30]

  • Details about Prerna’s first startup, Yaari, the pivot it made, and why it closed. [12:39]

  • Moving onto a music creation app, Songify, after Yaari closed and the inspiration behind it. [15:45]

  • The double-edged sword of achieving your goals and creating success that you never dreamed of. [19:29]

  • Getting acquired by Smule and the big decision to sell everything & move to Costa Rica. [21:35]

  • How Prerna applied The Lean Startup methodology to a book concept she was working on [27:19]

  • When Prerna reached her ‘aha moment’ on the journey to creating HOOKED. [30:54]

  • Prerna shares 3 lessons on what makes certain businesses go viral. [34:00]

  • How Prerna thinks about balance in her life and what makes her feel most balanced. [37:10]

  • Advice for those looking to go down the fundraising route. [40:20]

  • Why venture capital is not for everyone and it is not the only way your business will succeed. [41:32]

  • Hear some of Prerna’s rituals that keep her motivated and inspired. [44:07]

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Ep 35 | Holly Thaggard

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Ep 33 | Shilpa Shah