Hi, I'm Shane Mac.

I try to ask questions
most people don't.


It was a simple idea then and it's a simple idea now. Over ten years ago I decided to start asking people one question they don't usually get asked. This simple idea has led to hundreds of interviews, a dinner series, and a personal mission to make the world a more curious place. Nothing has impacted my life and work more than working on this. Listen to ask on Apple Podcasts, Soundcloud, and Spotify. Some past guests include Simon Sinek, Gary Vaynerchuk, Steve Huffman, Chase Jarvis, Amanda Bradford, Jason Fried, Michelle Broderick, Grant Imahara, Ryan Carson, Brad Feld, Lewis Howes, Robert Stephens, and many more. Click below to follow and learn more about ask.

Check out ask.


I was CEO & Co-founder of Assist which was acquired by Conversocial in 2019. We spent the past 5 years at Assist building the future of AI and the talking internet with partners like Amazon, Google, Facebook, Apple, and Twitter. Our software powers Fortune 500 companies like T-Mobile, Fandango, 1-800-Flowers, Sephora, Best Buy, MGM hotels, and many more. I'm now an SVP at Conversocial.

I previously worked on Gist.com, which was acquired by BlackBerry for over $40 million. We were one of the first social CRM companies and grew to over 100 million people by 2010. I am the founder of ask and chairman of Squared Away and New Degree Press. I've been featured in the NYTimes, Wall Street Journal, NPR's All Things Considered, Forbes, USA Today, and more.

I also write, invest, speak, and play music for fun. When I speak, I mostly do live Q&A.

I like spending time with people who are in the arena. If you're struggling, need help, or just wanna talk about some crazy ideas, please reach out and say hello. It's hard doing your own thing. I'm so thankful for all those who have helped me along the way.

Send me a message on Twitter and thanks for stopping by,@shanemac


I wrote the business book "Stop with the BS."

"Stop with the BS is a compilation of small, tactical strategies and advice that will make you think differently about the way business and careers work. You only have so much time to do what you want to get done, so make sure to focus on what is most important to you."
- Tony Hsieh
, NY Times bestselling author of "Delivering Happiness" and CEO of Zappos.com, Inc.

"Shane has some stuff figured out that lots of people never get. What he wrote on this train ride, you'll be thinking about for much longer."
- Julien Smith
, NYT Best-selling Author of Trust Agents

Check it out on Amazon here


I love music and mashups. I created the world's first live mashup show with wait what, the producer and DJ behind the Notorious XX. That debut album garnered 1M+ plays in 10 days and critical acclaim from New York Magazine, Rolling Stone, The New Yorker, and The Guardian UK, who dubbed it "the best mashup album of the year."

Check out a video from our last show

Simon Sinek
NYTimes Best-selling auther of
"Start with Why"
Chase Jarvis
Photographer & CEO Creativelive.com
Gary Vaynerchuk
CEO VaynerMedia, NYTimes Best-selling author, Investor
Grant Imahara
Host of Mythbusters and Actor
Steve Huffman
CEO & Co-Founder of Reddit
Steve Huffman
CEO & Co-Founder of Reddit
Jason Fried
CEO Basecamp, NYTimes Best-Seller
Grant Imahara
Host of Mythbusters and Actor
Grant Imahara
Host of Mythbusters and Actor


I love building, investing, and helping out with products and companies. I also believe side projects are where the magic happens. I find when we aren't so serious and just playing around that we find what we should be working on. Send any ideas my way, I'd love to check them out.

Remember app
I hate forgetting someone's name. I built a simple yet powerful product to remember everyone's name and the place where you met. It also sends me a notification 20 ft outside the door the next time I walk in. It's powerful.

Squared Away
Personal assistants who are military spouses. I helped Michelle, CEO of Squared Away, start a personal assistant company for military spouses who are always living in new cities.

Creator Institute & New Degree Press
Chairman of the Board. We are creating a new school that teaches people how to be a creator.

Machine Yearning
A podcast season we produced with the founder of RadioLab & Limina House about the future of AI and the talking internet.


Inspired by Patrick Collison, these are some questions that I find interesting.

Want To Know What Your Brain Does When It Hears a Question?
Questions hijack the brain. The moment you hear one, you literally can’t think of anything else. And that can be a powerful tool. Behavioral scientists have also found that just asking people about their future decisions significantly influences those decisions, a phenomenon known as the “mere measurement effect.” Back in 1993, social scientists Vicki Morwitz, Eric Johnson, and David Schmittlein  with more than 40,000 participants that revealed that simply asking someone if people were going to purchase a new car within six months increased their purchase rates by 35%.