Brad Schiller - CEO of Prompt

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Brad Schiller is co-founder and the CEO of Prompt, a company focusing on making people better writers through a combination of software and providing writing tutoring at scale. Brad is a writer, having written extensively on such topics as college admissions essays and case interview preparation for aspiring consultants.

Previously, Brad founded Beacon Ventures, a consultancy to PE firms, PE portfolio companies, and the Fortune 500. Before that, Brad was the first employee (2nd person) at Airware, a Y Combinator and VC-backed drone start-up ($85M funding), and he spent nearly 5 years at McKinsey after graduating from MIT.

Prompt manages and supports the college application writing process. Students receive a Personalized Assignment List over everything they need to do to complete applications for their school list based on Prompt's database of every requirement for every school (e.g., essay prompts). Students use Prompt's Content Strategy and Essay Outlining tools to develop the content and structure for their applications – effectively eliminating bad first drafts. Organizations use Prompt's essay review tools and workflows to review essays or access personalized feedback on essays from Prompt's global network of writing specialists. Prompt is used by high schools, college access organizations, and hundreds of independent admissions consultants.

Brad encourages interesting people to reach out to him at [email protected].

Highlights from the conversation:

• Brad's personal story of receiving valuable writing feedback at his first job
• The crazy story of DoesMyEssaySuck.com (yes, that was a real website!)
• Why content and structure are two focal points for the feedback given by Prompt instructors
• The tools Prompt has created to help students get started with college essays
• Take a guess: what % of student essays are submitted to Prompt within two weeks of the college app deadline? Hear the answer at 16:30
• Instructional and actionable: the two keywords for feedback on student writing
• The surprisingly quick rate that Brad's company helps students improve their essays
• No, AI isn't coming to steal teachers' jobs - Brad explains why at 22:50
• Brad's bet on writing help as a massive opportunity in EdTech
• Business development tip: The clever business partnership Prompt has with college admissions consultants
• Brad's strategy on growing out of the revenue Prompt creates and understanding market signals
• The decision-making process the Prompt team went through to plan its growth moves (35:12)
• An honest look into the decision not to raise venture capital funding - Brad explains it
• What's up next for Prompt?

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Thanks for listening!

Gerard Dawson