Most business owners think getting a call from private equity is the finish line. Brian Will says that's exactly when you're most at risk. In Part 2, Brian delivers the frameworks that took him three exits and decades of hard lessons to build — from the five keys to success (which are also the five keys to failure) to what private equity firms will do to your earn-out if you're not paying attention.

In this episode:

The five keys to success — and why every single one is also a key to failure
Why your business is not your product — it's the business inside the business: marketing, data, systems, and the ability to put any product through a machine that finds customers and converts them
The private equity playbook most sellers never see coming: how an $80 million deal became $60 million, why earn-out structures based on EBITDA are almost always a trap, and why you must never let a PE firm take over your accounting
Brian's AI workflow — three screens, three AI models (Gemini, ChatGPT, and Claude, which he calls Jake, Elwood, and Jeff), and the one prompt he uses to make sure they challenge him
Why you should stop chasing advice from billionaires — and find someone exactly ten steps ahead of you, fresh out of the game, who's made mistakes at your level recently enough to still remember what they felt like
Living Forever AI: Brian's current startup building interactive AI twins for personal legacy, professional use, and homeschooling — and why he's bootstrapping it while competitors have raised $20 million.

Episode Highlights:

00:00 - Escape the Commodity Trap

00:30 - Podcast Intro and Setup

01:30 - Five Keys to Success

01:50 - Key One Strong: Why

02:25 - Keys Two and Three

04:38 - Key Four: Check Ego

05:25 - Key Five: Master P&L

07:33 - KPIs and Pattern Forecasting

09:54 - Pricing and Testing

13:14 - Business Is a Data Game

14:59 - AI for Financial Analysis

16:49 - Living Forever AI Twins

20:37 - Experience Meets AI

23:56 - AI Jobs and Media Fear

29:36 - Why Start at 60

31:07 - Proving It Again

31:52 - Builder Not Manager

32:43 - Exit Strategy Reality

34:51 - Private Equity Earnouts

39:43 - How PE Rollups Work

44:02 - Structuring Safer Earnouts

45:44 - Post Acquisition Lessons

49:52 - Business Beyond Product

55:28 - Using AI As Advisors

57:52 - Stop Chasing Billionaires

01:00:49 - Final Advice And Wrap

Resources mentioned:

Dropout Multimillionaire, No: The Psychology of Sales and Negotiations, The Invisible Multimillionaire, I Give the Dumb Kids Hope — Brian Will's books
Living Forever AI — Brian Will's current company: https://livingforeverai.com/
brianwillmedia.com — Brian Will's website
ChatGPT, Gemini, and Claude — Brian's three AI models, running simultaneously for business planning and analysis
The 7 Habits of Highly Effective People — Stephen Covey

Quotes:

“ If you are a commodity business, the only way for you to win is to chase pricing down to the bottom until you can't make money.” - Brian Will

“ I did a company, literally 32 marketing channels, and when I did the analysis, nine of those channels were unprofitable. Nine. And they represented 20% of their spend, their marketing spend.” - Brian Will

“ And at some point, I started questioning me. I've been doing this consulting thing and telling people what to do for 20 years. I wonder if I actually know what I'm talking about.” - Brian Will

“ Wherever you feel, you know, some angst around something, and this could be anywhere in your life, I think it's really important that you lean into it and realize that that angst is, is not there for you to pull back from anything. It's actually for you to lean into something, and there's something that you don't yet know.” - Dwayne Kerrigan

“ Stop chasing the advice of billionaires, because they can't help you.” - 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.