End Small Talk
Introducing End Small Talk: Deep Questions for Better Conversations by Cory Stout

Otterpine is excited to announce the release of End Small Talk by entrepreneur and deep thinker, Cory Stout!

Cory Stout is the founder of Woodies Sunglasses and a long-time friend of Otterpine. His new book, End Small Talk, contains over 250 unique and thought-provoking questions to spark conversation and encourage people to connect on a deeper level. But this isn’t your average book of conversation starters. Categorized on a scale of 1 to 10, these questions are designed to move beyond small talk so you can have truly authentic conversations that cover a range of topics and styles—from hypothetical to literal, from pop culture to personal, and everything in between.

We sat down with Cory to explore the inspiration behind this thought-provoking project, and we’re excited to share his insights!

How would you describe your book in your own words? If someone asks, “What is End Small Talk about?” you say…

End Small Talk is about non-rehearsed conversation. Most people you meet, you’ll only see them once in this lifetime. What would you ask someone if you knew this was the last conversation? 

What inspired you to try to end small talk? 

I traveled extensively in hostels and the questions people usually asked were so brain-numbing. I wanted better.

Do you have any advice for anyone who is trying to have deeper conversations but might be worried about answering these questions

You have to read the group before you ask certain questions. A group of strangers just isn’t ready for level 10 questions unless they’re near the trash fence at Burning Man. A good prescription is to push people to the edge of their comfort zone without going over.

End Small Talk

What was your process like when writing this book? Have you asked people these questions, and have you answered them yourself?

In the process of writing this book, I asked at least 1,000 people questions. The questions were slowly refined, like a comedian trying out material. 

What’s your favorite question to ask a stranger?

My go-to question is: Is falling in love more like winning the lottery or learning to play the piano? The most likely answer is somewhere in between, and the false dichotomy leads to fertile conversations. Plus, people just love talking about love.

Your book explores what it means to have deep conversations. What drew you to this endeavor, and what do you hope readers will gain from reading this book?

Conversation is at the core of human connection. It comes so naturally and probably always has.

I hope everyone will carry around a small notebook and publish their insights every couple of years. It’s surprising how much you can create with a little bit over a long time.

What’s next for you as an author? Do you have any future writing projects or exciting plans on the horizon?

I decided to disconnect from the internet for a year and write a book about it. I’m scheduled to reconnect on January 13th, so stay tuned to see if I’ll even want to reconnect.

Also, I want to give a shout out to Saeah! This book would low key suck without her.

End Small Talk

End Small Talk is available in paperback and E-Book on Amazon.

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