Arun Gupta

Inquirer
DISC Type : cd

Chief Executive Officer at Hapiko

New York, New York, United States

Overview

Arun Gupta is a serial entrepreneur and the CEO of Hapiko, a creative technology company for children. A Yale University graduate, he previously founded the successful mens fashion marketplace Grailed, which he grew to millions of users before it was acquired. His career began at the Y Combinator startup accelerator.

Arun is passionate about building products that foster creativity and connection. His latest venture, Hapiko, aims to merge technology with hands-on, imaginative play for children, moving them away from passive screen time. He has a history of identifying niche community needs and building platforms to serve them.

Unique fact: His first venture was one of Y Combinators earliest hardware startups, an alarm clock wristband that analyzed users sleep cycles.

Personality Overview

Judgemental

ROI Conscious

Upfront

They can be nudged to make faster decisions by offering what they value.  They respond well to confident salespeople. They care equally about the product and its potential impact.

Topics They Care About

AI for Children
His new company, Hapiko, is focused on creating safe, "creativity-first" AI experiences for kids that encourage hands-on play instead of passive screen time.
Serial Entrepreneurship
Has founded multiple companies, starting with a Y Combinator-backed hardware startup, then building and selling the e-commerce platform Grailed, and now leading Hapiko.
Creative Technology
Expresses a love for building products that connect people and spark creativity, from fashion communities to tools that bring children's imaginations to life.

Media Appearances

Arun has no verified media appearances

Work History

1-2025
Chief Executive Officer at Hapiko
9-2013 - 12-2024
CEO at Grailed
6-2008 - 12-2011
CEO at Perfect Third Inc.
Student Fellow at Yale Entrepreneurial Institute
Student at Yale University

Education

2006 - 2010
Bachelor of Science (BS) from Yale University
2009 - 2009
Education details unavailable from Y Combinator

More Information

Social Presence :

Prographics :

Exp : 15 Location : New York, New York, United States Job Level : Leadership Designation : Chief Executive Officer at Hapiko
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Insights For Selling To Arun

During A Call Or A Meeting

DO's

  • Tell them that you are there to help them create visible impact within their organization
  • Get to the point quickly instead of spending too much time on pleasantries
  • Highlight the competitive differentiation of your product

DONT's

  • Avoid repeating yourself or making generalizations
  • Don’t expect them to change their mind quickly if they say no once
  • Avoid long winding pitches, stay objective

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Arun is

  • Conviction in the product matters to them, followed by proof points and strong testimonials.
  • Will you ever get a clear answer from Arun

  • They may not be very forthcoming, but they will say no if needed.

Insights For Deal Planning

    How fast (or slow) will Arun move?

  • They are neither the fastest decision makers nor the slowest.
  • Can Arun take some risk or not?

  • They can take risks but after weighing up the pros and cons.

You And Arun

Personality Compatibility


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