notes from the first ask dinner.

What if everything started with a question?

the idea

It all started 4 years ago. It was a simple idea then and it’s a simple idea now. I set out to ask 1 question to a wide range of leaders all over the world.

In a short time, I’ve been lucky and humbled by this experiment. I’ve had the great opportunity and pleasure to ask questions and learn from the tech rock stars, NGO leaders, professional athletes and CEOs of Fortune 500s. Since then it’s become a way of life, not just some interview blog.

But, I always wanted to host a dinner for ask. I wanted to take it to the next level with the ask dinner. An evening of learning, debates, delicious food and diverse conversations.

There were going to be a few rules as well;

  • The entire evening was driven by questions and a moderator. Thanks Antonio Neves.
  • Everyone is equal and everyone has a voice. There are no “speakers” or “podiums.”
  • Check out and being present, personal. No cell phones or computers allowed during dinner. Must be turned off.
  • Required dress is black and white attire. A classy gathering.
  • You’ll receive an ask notebook to take notes, remember everything and have something that you can keep forever to remember the evening.
  • The 10 people were hand picked to guarantee an unforgettable experience. (I tried for more ladies but they wouldn’t come!!! Thanks Michelle Bee for being a trooper!)
  • You don’t need to do anything except show up. I will have a photographer come so we can capture the true essence of the night (check out the photos below).

the experience

We broke the night into 3 - 1 hour sections. Different types of questions progressing to more personal and challenging as the night (and wine) went on. The goal was an intimate, personal setting where everyone would feel safe to share personal and behind the scenes stories. I told everyone at minimum we will have an amazing meal and at maximum we will have a night we remember forever.

I started the night with a little history of ask, why I think checking off and indexing a notebook is the best way to get work done and a quote from Jay Z because I know people have tons of other things they could be doing;

"Tonight, you could be anywhere but you chose to be here with us (me is what Jay Z says)" - Jay Z

Antonio started the main part of the night with this simple question;

"Tell us one thing about yourself that no one could find out about you online."

That lead the tone for the entire night. It was truly amazing hearing honest stories about insecurity, failing, fear after 9/11, being paralyzed twice, how social channels are the biggest hindrance to ones life, divorces affect on entrepreneurs, how fortunate we are in life, working to be the best husband and so many others that I feel really made the entire group of people come together in a meaningful, different way.

I didn’t have the dinner to get anything out of it. I had it to be with people I’d love to be friends with, learn from and hopefully become closer by asking hard, honest questions.

I got exactly that.

the people

Moderator: Antonio Neves -

The 9 people:

  1. Michelle Broderick -
  2. T.A. McCann -
  3. Marc Nager -
  4. Josiah Johnson -
  5. Brian Nash -
  6. Peter Boctor -
  7. Shane Mac -
  8. Chase Jarvis -
  9. Nick Soman -
  10. Photos: Max Mcsimov -

I honestly can’t say thanks enough for the experience that I got from being in the room with these 10 people for just one dinner. Thank you.

Want an ask notebook? Remember everything and get one here.

Want to have your own an ask dinner? Email me for the playbook at [email protected]

Also, a very special thanks to Arjun Dev Arora, Chuck Longnecker, T.A. McCann, Adam Hofmann and Michelle Bee for pushing me to host the dinner. Also, thanks to Tim Ferriss for the inspiration to create a notebook all around indexing.

the photos