The Chicago Wellness Challenge featured in the local and national news. Learn more about the Spring 2019 challenge, the participants and wellness.


Bootstrapping in America’s special week-long series featured an incredible group of entrepreneurs who were a part of the Chicago Wellness Challenge. The program was designed to help entrepreneurs and business professionals make their mental and physical health a priority. The Spring 2019 Challenge was an overwhelming success and really made a difference in many lives.

Bootstrapping in America

Pete Wilkins - Founder of the Chicago Wellness Challenge

Mike Apostal - Co-Founder and CEO of Factor 75

Jordan Buckner - Founder and CEO of Tea Squares

Lee Shapiro - Co-Founder of 7 Wires Venture & CFO of Livongo

Chad Driscoll and Josh Siroko - Co-Founders of LIFT


Thrive: How a wellness challenge can help bring mental health to the workplace

Founding Participant and G2 Chief Marketing Officer, Ryan Bonnici shares his thoughts on the Chicago Wellness Challenge in Thrive Global.



Now week six of the #ChiWellnessChallenge, the crew is closing in on their wellness goals. Founding Participants TastyTrade’s Co-CEO Kristi Ross and TeaSquares founder Jordan Buckner join host, Scott Kitun, and challenge creator Pete Wilkins to discuss what they are doing to better themselves as part of the challenge.


Technori: Challenge check-in

Learn how several Founding Participants and Partners are progressing toward their #ChiWellnessChallenge goals.



Several Chicago Wellness Challenge Founding Participants share their perspective about the challenge.

Technori: The Why behind the ChiCago Wellness CHALLENGE

The Founder of the Chicago Wellness Challenge, Pete Wilkins joins Scott Kitun on the Technori podcast to discuss the #ChiWellnessChallenge (and little bit about startups and venture financing)

Thrive: The Chicago Wellness Challenge

The Chicago Wellness Challenge featured in Thrive Global, the medium dedicated to unlocking human potential.


wgn Radio: A Healthy No

Chicago Wellness Challenge Founding Participant and The SimplyBe Agency CEO, Jessica Zweig, talks about the power of saying NO and YES to wellness.


Optimizing Entrepreneurial PErformance

Pete Wilkins, Chicago Wellness Challenge Founder, explains how WHOOP provides key data about strain, recovery, and sleep to perform better at work and home.


wgn Radio: Eating Right on the Run

Chicago Wellness Challenge Founding Participant and Factor 75 CEO, Mike Apostal, calls in to talk about nutrition and how 75% of your fitness results come from what you eat!


3 Easy Steps for Entrepreneurs to Sleep Better

Three healthy sleep habits to help your body function in all of your personal and professional endeavors written by Ellie Porter, Managing Editor, in support of the #ChiWellnessChallenge.


Thrive: How I Train for Life: A VC Perspective on Wellness

The Chicago Wellness Challenge Founder, Pete Wilkins, provides 5 powerful tips to improve wellness.