In a world where “charge what you’re worth” and “raise your prices” dominate the entrepreneurial conversation, Kelly is flipping the script with a reality check:

In this episode, she reveals why some of her biggest business wins — from stage appearances to multi-million-dollar brand growth — came not from getting paid upfront, but from playing the long game.

You’ll learn when it actually pays to work for free, how to evaluate opportunities strategically, and how to turn short-term sacrifice into long-term expansion.

If you’ve been wondering whether to charge or say “yes” for exposure, relationships, or visibility — this is your playbook for discerning which “free” is actually profitable.

Timestamps: 

[00:40] – Why “charge what you’re worth” isn’t always great advice — and how nuance creates better business decisions. [02:00] – The problem with instant gratification and how long-term strategy builds wealth  [04:15] – Free vs. paid speaking engagements — the $20K talk vs. the thousand-person audience. [05:45] – The free, local speaking events that led to new paying clients within 48 hours. [07:00] – The asset advantage: why visibility and brand content are often worth more than upfront payment. [08:30] – Kelly’s 4-part checklist for evaluating an unpaid opportunity [10:15] – The truth about big stages: how most speakers land them — and why most aren’t getting paid. [13:30] – Why Kelly doesn’t take podcast sponsors (yet) and how the show makes millions without a single paid ad slot (and why long-term audience trust is more profitable). [18:00] – The currency of integrity: why doing the right thing compounds in value over time. [19:00] – Final encouragement: trust your discernment, play the long game, and remember — nothing is impossible with God.

 

Resources:

• Join The Virtual Business School now for just $87/month, no contract: https://go.virtualbusinessschool.com/joinvbs 

• Learn more about our Legacy Leaders Mastermind: The premier mastermind for established 7- and 8-figure CEOs: https://programs.thebusinessadvisory.com/legacy-leaders 

• Join us in person this March for our annual Legacy retreat ($2M+ business owners): https://advancesociety.org/2026rsvp 

• Follow Kelly on Instagram: https://www.instagram.com/kellyroachofficial/               

  Follow Kelly on Facebook: https://www.facebook.com/kelly.roach.520/w    

  Connect with Kelly on LinkedIn: https://www.linkedin.com/in/kellyroachint/