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STRIVE Mentor Q&As

Thinking about career options? Want to know what a particular job or career path is really like? Join STRIVE’s Online Mentor Q&A Program and get real insight from active professionals on:
  • how they chose their career
  • what their day-to-day work is like
  • what skills, qualifications and mindset is helpful in their field
  • what value they are creating and trading
  • lessons they’ve learned along the way
  • and anything else you might like to know

We encourage you to participate in all sessions, since the conversation extends beyond field-specific questions into broader questions touching on all aspects of value creation and work-life balance. Also, it gives you a chance to learn about career paths you may not have considered. Want to see a particular professional featured, who is sympathetic to free-market principles? Let us know and we will try to schedule him or her. Email: info@striveclubs.org.


  • Duration: 60 minutes
  • Format: Moderated Q&A. The mentors and moderators are visible on webcam, the participants can send in questions ahead of time, and ask them live over chat
  • Platform: GoToWebinar
  • Schedule: Approximately monthly, either on Sunday afternoons or Wednesday evenings, at the mentor’s convenience.
  • REGISTRATION IS REQUIRED. Please like our Facebook page at https://www.facebook.com/striveclubs/ to be notified of upcoming Mentor Q&A Events. The GoToWebinar registration link for each event will be provided as the event is announced.


Fantastic session, Don Watkins! Lots and lots of useful, actionable wisdom. Specifically, my favorite part was your advice on how to be a good mentee and how mentoring relationships DO provide value to the mentors, not just the mentee. Thanks for this session! It was definitely time well-spent for me.”

Halelly Azulay

Founder and CEO at TalentGrow LLC

Past Q&As

Josh Windham

Attorney at Institute for Justice

Josh is an attorney at the Institute for Justice as well as an editor for The Undercurrent magazine.

Date: April 12 at 8:30 pm CT

Tal Tsfany

Chief Customer Officer at Base

Tal is the Chief Customer Officer at Base CRM as well as the co-founder of the Ayn Rand Center Israel.

Date: March 24 at 3 pm CT

Kendall Justiniano

Marketing Director at Design Structures & Solutions

Kendall is a Global Business Unit Marketing Director at PolyOne Designed Structures and Solutions LLC.

Date: January 29th at 3pm CT 

Katelynn McBride

Program Director at Notre Dame Law School

Katelynn specializes in career counseling and helping students craft their personal brand as the Program Director for Public Interest & Chicago Initiatives at Notre Dame Law School. Previously, Katelynn worked as an attorney at the Institute for Justice.

Wednesday October 12th at 7pm CT

Don Watkins

Author & ARI Fellow

Don is a fellow at the Ayn Rand Institute, author of RooseveltCare: How Social Security Is Sabotaging the Land of Self-Reliance and coauthor of Free Market Revolution: How Ayn Rand’s Ideas Can End Big Government and Equal Is Unfair: America’s Misguided Fight Against Income Inequality.

Listen to the recording here.

Sunday, September 11th at 3pm CT

Sunny Lohmann

Political Humorist

Sunny is a political humorist and YouTube personality at The Daily Sunny and House of Sunny. She has appeared on PJTV and occasionally writes for PJ Media and The Daily Caller.

Wednesday, August 17th at 7pm CT

Eric Daniels

Eric Daniels

Science Teacher and Curriculum Specialist

Eric trained as a historian and has worked with students at the university level but now specializes in childhood and adolescent education.

Sunday, July 17th at 3pm CT

Scott McDonald

Branch Chief at Marine Corps Headquarters

Scott has served with the Marine Corps in Iraq, before transitioning to diplomatic, strategic, and communication leadership roles at HQ in Washington DC.

Wednesday, June 8 at 7pm CT

Adam Mossoff

Scholar on Intellectual Property Law

Adam is a Professor of Law at George Mason University, and founder of the Center for the Protection of Intellectual Property.

Wednesday, May 25 at 7pm CT

Philipp Dammer

Professional Juggler

Philipp is a professional juggler based in Bochum, Germany. If you are considering an unusual career path, this Q&A is for you!

Sunday, May 8, 2016 at 3pm CT

Ben Wilson & Elizabeth Laughton

Trial Lawyers

Ben is an Associate at Hepler Broom LLC in St. Louis, MO and specializes in toxic tort litigation. Beth is an Associate at Munger, Tolles and Olson LLP in Los Angeles, CA and specializes in patent litigation

Sunday, April 17, 2016 at 3pm CT

Gena Gorlin


Gena is a Doctor of Clinical Psychology, currently working as a resident at Brown University.

Sunday, April 3 at 4pm CT

Jason Crawford

Entrepreneur & Founder

Jason is a serial entrepreneur (Fieldbook, Kima Labs) and has worked in a number of startups (Groupon, Pelago).

Sunday, March 20 at 3pm CT

Andrew Layman

Former Entrepreneur & Current Director at Salesforce

Andrew sold his startup to Symantec, and grew a career in product development at Microsoft and now at Salesforce.

Sunday, February 28 at 3pm CT

Alex Epstein

Intellectual Bodyguard to the Fossil Fuels Industry

Alex has founded the Center for Industrial Progress and is author of “The Moral Case for Fossil Fuels”.

Wednesday, February 17 at 7pm CT

Steve Simpson

Director of Legal Studies at ARI

Steve is the Director of Legal Studies for the Ayn Rand Institute, and former senior attorney for the Institute for Justice

Date: June 21 at 3 pm CT