Kevin Bracken left New York when he was 18 years old. He made good on a public promise in 2004 to move to Canada if George W. Bush were re-elected. Bush was re-elected, and Kevin now calls Toronto home most of the year. 

 

Part event planner but mostly a philosopher, Kevin is the instigator behind his global events juggernaut Newmindspace, founded in Toronto. He has produced thousands of events in over 200 cities around the world. His contribution to culture has impacted hundreds of thousands of people. 

 

With Jake, Kevin discusses his idea of the “urban playground movement” (a phrase he coined), how he and his team have evolved the rave culture and why it’s so important to him re-imagine how urban centers are used. He talks about the lies of Silicon Valley (he’s received venture capital funding for two startups) as well as breaking rules, causing chaos, marketing smartly and being genuine. 

 

Today, October 27, it’s election day in Toronto, and Kevin is planning an event called “Rob Ford: The Business as Usual Party” which celebrates the departure of crack addict Toronto Mayor Rob Ford. The fun starts at 9PM at Toronto City Hall.  

 

At the top of the show, Jake and Cait discuss Caitlin's desire to bring a third person (a second woman) into her relationship in the bedroom to spice things up and a meeting that followed with the $100 million founder & CEO of AshleyMadison.com in Toronto. 

 

The Jake Sasseville Show is produced by Jake Sasseville, Gregory Stuhtzer, Vivienne Kelly, Caitlin Engel in New York City, Christopher G. Keene in Massachusetts and Kodi Seaton in Washington D.C. (c) 2014

Doug Akin was the quintessential Mad Man. He co-founded the Mr. Youth advertising agency (which he later sold for millions), launched a restaurant in the West Village right near his apartment. His agency helped to define the social media revolution in the 21st century and continues making huge waves today.  

These days though, Doug can be found living on a bus. Specifically, the Gratitude Bus, which is parked in the Hamptons. After he sold the agency, Doug started on a trek across the world to find himself. 

He shares with Jake what he realized after he visited his twentiest country --  the key to what he had been looking for his whole life. He talks about the early days of Mr. Youth, how he won business with Nestle, JetBlue, HP and every major brand in the United States, getting the call from the Facebook co-founder asking for help and what he says propelled him to material and spiritual success. 

Doug can best be reached at instagram.com/IamDougAkin

At the top of the show, Jake and Cait discuss spirituality and giving your friendship an occassional sabatical. Womp womp. Hint. Hint. 

The Jake Sasseville Show is produced by Jake Sasseville & Gregory Stutzer. Also: Kodi Seaton, Caitlin Engel, Vivienne Kelly and Christopher G. Keene. (c) 2014 All rights reserved. 

Tara DeFrancisco is considered by many to be one of the greats of improv comedy this country has ever seen. 

Certainly in Chicago, but all over the world, Tara has made a name for herself as a playful and insightful entertainer who Free Press calls the "funniest woman in Chicago" and Curves Magazine wrote is by far the "top 25 funniest females in the United States." 

Early in her career after being cast out of 700 hopefuls, Tara followed in the steps of Amy Poehler, Steve Carell, Jane Lynch, Martin Short and others cutting her teeth 250 days a year touring with Second City. By 33, Tara had done over 3,000 shows. 

In her ever candid, often hilarious and consistently vulnerable interview with Jake, Tara discusses Saturday Night Live, why she loves Chicago, the art of improv, taking risks, following her dreams and self-acceptance. She takes us on a deep dive inside her mind and heart and we get to explore what makes her tick, how she got so good and why she keeps coming back for more. 

At the top of the show, Jake and Cait talk about the Men's Health magazine article slamming females in sports, Jake's childhood (and adult) closet obsession with Rosie O'Donnell and Caitlin's new film "A Long Walk to Forever," adapted from a Kurt Vonnegut Jr. short story. 

The Jake Sasseville Show is produced by Jake Sasseville and Gregory Stutzer. Associate producers Kodi Seaton, Caitlin Engel and Vivienne Kelly. (c) 2014 All rights reserved. 

Michael Simmons' father died when Michael was eight years old. That, he says, is why his life in business has been all about defying the odds.

He's the CEO of Empact Summit, has spearheaded over 600+ entrepreneurial education workshops at universities around the world and is the popular columnist at Forbes about relationship building in the age of social media.  

Michael sits down with Jake to discuss relationships, the #1 mistake he says people make when trying to be social on social networks, why being open and vulnerable with all people, not only certain ones, is imperative to being successful and how to build rock solid relationships even if you're a quiet or shy person (hint: it's about serving others, not you!)

At the top of the show, Jake and Cait discuss important lessons learned (and mistakes made) in building relationships in business and why Cait won't go with Jake on the Transiberian railroad from St. Petersburg, Russia to Beijing, China. 

The Jake Sasseville Show is produced by Jake Sasseville and Gregory Stuhtzer. Associate producers Kodi Seaton, Caitlin Engel and Vivienne Kelly. (c) 2014 All Rights Reserved