Brian Will has owned 10 companies across five industries, made three exits worth over $500 million, and written four books — including two Wall Street Journal bestsellers. None of it was handed to him and the odds were very much against him. In this conversation with Dwayne Kerrigan, Brian unpacks the frameworks behind his success: the personal filter, the success ladder, and the $80 million decision he almost said no to.

In this episode:

The "I'm in" moment: Brian's business partner Steve asked him to borrow $66,000 more after nine months of zero revenue and $500,000 in losses — Brian's accountant, CMO, and COO all quit before he finally said yes, and the company sold for $80 million just 18 months later
Why "failure leads to success" is a myth Brian calls out directly — it's learning from failure that leads to success, and most people skip that step entirely
The success ladder framework: Brian started at step zero with no education, no backing, and no mentors — and why the only two ways to climb are to learn every painful lesson yourself or find someone who's already done it
The personal filter concept: everything you've ever heard, read, and experienced creates a subconscious filter that accepts or rejects new information — and why people who seem to have the Midas touch aren't lucky, their brain just knows how to recognize success
How Brian's abusive childhood created what he calls the "anger box" — and how that same fuel, once controlled, became his most powerful sales and leadership tool
Why three years of counseling after his divorce was the moment he realized the only person he was still trying to prove anything to was himself

Episode Highlights:

00:00 - Keep Moving Forward

00:15 - Podcast Intro

00:47 - Meet Brian Will

02:53 - Dumb Kids Hope Story

04:40 - Military Discipline Lessons

08:30 - Abuse, Anger, and Trauma

12:28 - Anger Box Control

13:35 - Learning From Failure

17:04 - Mentorship Strategy

17:59 - Steve and the Big Bet

19:40 - All In Decision

20:38 - Breakthrough and Exit

22:36 - Ego Surrender and Trust

26:46 - Vulnerability and Divorce

32:20 - Drowning Mind in Books

34:30 - Who Steve Was

35:27 - Equity Swap Origin Story

39:23 - Email Marketing Gold Rush

41:10 - Success Filter Framework

46:05 - Wrap Up and Next Episode

Resources mentioned:

I Give the Dumb Kids Hope, Dropout Multimillionaire, No: The Psychology of Sales and Negotiations, and The Invisible Multimillionaire — Brian Will’s books
How to Win Friends and Influence People — Dale Carnegie book
Master Key to Riches — Napoleon Hill book
The E-Myth Revisited — Michael Gerber book
Blink — Malcolm Gladwell book
Rich Dad Poor Dad — Robert Kiyosaki book
Living Forever AI — Brian Will's current company: https://livingforeverai.com/

Quotes:

“ Failure does not lead to success, ever, never, ever, ever. Learning from failure leads to success, and that's the thing that a lot of people don't do, especially in business.” - Brian Will

“ In 60 days, we hit our first offer. We did $6 million, then 20, then 30, and then sold the company for $80 million 18 months later.” - Brian Will

“ The only person that still thinks, or in my case, still thought that I was that kid laying in the yard crying after I got beat up by my stepdad was me. I was the guy that I did, I had to prove something to.” - Brian Will

“ Failure will be inevitable at some point, and learning is optional." - Dwayne Kerrigan

“ It's your personal filter that will determine whether you succeed or fail in life.” - Brian Will

“ Most of the time, they quit right before they're about to make a breakthrough. That's just a fact.” - Brian Will

About Brian Will:

Brian Will is a serial entrepreneur, two-time Wall Street Journal bestselling author, and business consultant who has founded or co-founded ten companies across four industries, with combined valuations exceeding half a billion dollars. He is a two-time TEDx speaker and the author of four books including Dropout Multimillionaire and No: The Psychology of Sales and Negotiations. Currently, Brian is the CEO of Living Forever AI and runs a coaching and consulting practice helping entrepreneurs master the core metrics, sales systems, and processes that drive sustainable growth.

Connect with Brian Will: https://brianwillmedia.com/

Connect with Dwayne Kerrigan

Disclaimer: The views, information, or opinions expressed by guests during The Dwayne Kerrigan Podcast are solely those of the individuals involved and do not necessarily represent those of Dwayne Kerrigan and his affiliates. Dwayne Kerrigan or The Dwayne Kerrigan Podcast is not responsible for and does not verify the accuracy of any of the information contained in the podcast series. The primary purpose of this podcast is to educate and inform. Listeners are advised to consult with a qualified professional or specialist before making any decisions based on the content of this podcast.