The Dwayne Kerrigan Podcast

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
Facebook
Instagram
Linked In
Website
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.

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
Facebook
Instagram
Linked In
Website
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.

Sean Barry's team used to spend six months building a feature. Now they build it in two to three weeks.
In Part 2, Sean and Dwayne move from the AI transformation inside LeanScaper to the bigger picture: what the software industry looks like in twelve months, why autonomous cars and AI adoption are fundamentally different problems, and what it actually means to participate in this change rather than spectate.
In this episode:
Why the software industry is facing a potential 50-80% company turnover in the next 12-18 months — and why it's simultaneously the best time to be a consumer of technology and the most terrifying time to be building it
The voice and ambient AI future that Sean sees arriving in the next 12 months: screens shrinking from 98% of the interface to 60%, then 20%, as conversational AI replaces the need to navigate software at all
Why AI adoption is fundamentally different from autonomous car adoption — when the choice is 150 hours of your time versus 5 hours with AI, it's not a choice your employer gives you, it's a choice that gets made for you
How AI can lift wages across entire workforces by removing waste from businesses — Sean's case that the real gift of AI isn't productivity, it's the ability to pay people more
Sean's closing philosophy on AI and empathy: the sentiment is largely negative because people aren't participating, and the antidote isn't optimism — it's getting informed, then helping others do the same

Start building your identity with Dwayne’s Identity Framework created for the LeanScaper Conference: https://www.dwaynekerrigan.com/identity-framework/
Episode Highlights:
00:00 - Be Informed About AI
00:25 - Podcast Intro
01:26 - Shipping Faster With AI
05:55 - Producing What Was Impossible
09:52 - Keeping Pace With Change
11:01 - AI’s Growth Curve
12:11 - Voice First Interfaces
16:54 - Future Of Software SaaS
21:16 - Build Vs Buy For SMBs
25:23 - Leverage Expertise With AI
27:31 - Does It Ever Normalize
31:12 - Autonomous cars
35:35 - Removing Waste Raising Wages
37:32 - Robotics And Scarcity
42:16 - How We Treat AI
46:12 - Participate With Empathy
51:12 - Closing And Disclaimers
Resources mentioned:
LeanScaper — AI operating system for the landscape industry
Lana — LeanScaper's AI agent
Mark Bradley — founder and chairman of LeanScaper
Claude Code — referenced by Dwayne as the platform he used for his planned 10-week AI course for his staff and their families
Lovable — referenced as a tool enabling small business owners to build their own apps
Eleven Labs / Cartesia — referenced in context of voice AI development
OpenClaw agents and Jarvis — referenced by Dwayne in context of his own AI setup
Tesla / Waymo — referenced in autonomous vehicle comparison
Anthropic — referenced re: recursive self-improvement blog post released day of recording
Paul Akers’s episode on The Dwayne Kerrigan Podcast — referenced regarding eliminating business waste: Episode 135: The Lean Maniac: Paul Akers on Eliminating Waste

Quotes:
“ This isn't a choice. Like, people who think this is a choice aren't paying attention. Back to what I said before, this happens either to you or with you.” - Sean Barry
“ What we accomplished in that two, three weeks would have taken us six months.” - Sean Barry
“ I honestly think it's normalizing already, and I have a wonderful wife who, who grounds me in these things because as well I'm like, "Man, if we're not go, go, go, like, we're gonna be left behind." And her very nuanced understanding of people, way better than I have, is like change takes time and people need time.” - Sean Barry
“ Nobody likes uncertainty, but that's where all the growth lies, is in your uncomfort.” - Dwayne Kerrigan
“ We can help an industry transform the lives of its entire workforce because we can take all of the waste out, and then all of a sudden there's enough money to really pay people well.” - Sean Barry
About Sean Barry:
Sean Barry is the Chief Product Officer at LeanScaper, an AI operating system and business community built specifically for the landscape and snow contracting industry. He brings nearly two decades of product and digital leadership experience, including almost four years at LMN (Landscape Management Network) — the landscape industry's leading business management platform — where he rose from SVP of Product to Chief Product Officer. Before entering the green industry, Sean spent 14 years at Laughlin Constable, a Milwaukee-based agency, where he built his career from Lead Engineer to SVP of Digital, Account and Innovation. He is currently at the forefront of applying AI to real-world business operations for contractors.
Connect with Sean Barry: https://leanscaper.com/
https://www.linkedin.com/in/sbarry/
Connect with Dwayne Kerrigan
Facebook
Instagram
Linked In
Website
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.

In January, 95% of the code Sean Barry's team wrote was written by hand. Six months later, that number is 2%. Sean isn't predicting what AI will do to your industry — he's living it, building it, and losing sleep over it.
In this conversation with Dwayne Kerrigan, Sean Barry - the Chief Product Officer of LeanScaper - shares what the AI transformation actually looks like from the inside: the grief, the identity crisis, the compounding flywheel effect, and the window that's closing faster than most people realize.
In this episode:
Why most small to mid-sized businesses can't implement AI on their own — and what LeanScaper is doing about it for the landscape industry
The compounding flywheel effect: why companies that embrace AI now may be uncatchable by competitors who wait six months
The emotional journey Sean's team went through when AI fundamentally changed their jobs overnight — and what's on the other side
Why the most powerful AI asset in your business might already be sitting in a drawer somewhere
The one thing Sean tells every business owner who doesn't know where to start
Why the resistance to AI — in boardrooms, on campuses, and inside teams — all traces back to the same root cause

Start building your identity with Dwayne’s Identity Framework created for the LeanScaper Conference: https://www.dwaynekerrigan.com/identity-framework/
Episode Highlights:
00:00 - AI Pace Shift
00:27 - Podcast Intro
00:59 - Meet Sean Barry
03:33 - LeanScaper Explained
04:33 - DIY AI Struggle
08:28 - Jobs Fear vs Abundance
14:46- Human Connection Premium
17:08 - Mindset, Education, and Retraining
25:57 - How to Start Using AI
30:36 - SOPs as Superpower
36:00 - Uncatchable Flywheel
43:43 - Grief and Identity Shift
53:26 - What Changed Since January
58:14 - New Team Workflow Rebuilt
01:00:51 - Wrap Up and Stay Tuned for Next Episode
Resources mentioned:
LeanScaper — AI operating system for the landscape industry
LMN (Landscape Management Network) — landscape industry business management software
Mark Bradley — Chairman and founder of LeanScaper
Lana — LeanScaper's AI agent
ChatGPT — referenced as starting point for AI adoption
Claude / Anthropic — cited as the inflection point in AI coding capability that changed everything in late 2024
Claude Code — referenced as coding tool
Codex — referenced as AI coding resource
GitHub Copilot / Microsoft Copilot — referenced in context of AI coding history
Figma — referenced as design tool being replaced by AI-assisted coding
OpenClaw agents — referenced by Dwayne as agents running in his own setup

Quotes:
“ Your choice is not whether or not this happens, your choice is whether it happens with you or to you, and that's the choice you get to make.” - Sean Barry
“ In January, ninety-five, ninety-eight percent of the code we would write was written by hand, and today, two percent. Yeah, that's six months.” - Sean Barry
“ Take next week off and stop doing your day job, and then spend forty hours learning AI and diving into ChatGPT, Codex, Claude. Figure out what you want. Dive in, there's tons of education. You just ask AI how to use it. Then the next week, that time will pay back. You will have moved yourself so far in that forty hours that you will get that time back the next week.” - Sean Barry
"You'll be uncatchable by people who don't." - Sean Barry
“ I think 95% of small to mid-sized businesses don't have the time nor resources to go accomplish that. So I think we're at the exciting point in what we're trying to do is, is take all that power and then do all the heavy lifting for landscape contractors so they can just turn it on and use it and not need to go figure out how to put it all together.” - Sean Barry
About Sean Barry:
Sean Barry is the Chief Product Officer at LeanScaper, an AI operating system and business community built specifically for the landscape and snow contracting industry. He brings nearly two decades of product and digital leadership experience, including almost four years at LMN (Landscape Management Network) — the landscape industry's leading business management platform — where he rose from SVP of Product to Chief Product Officer. Before entering the green industry, Sean spent 14 years at Laughlin Constable, a Milwaukee-based agency, where he built his career from Lead Engineer to SVP of Digital, Account and Innovation. He is currently at the forefront of applying AI to real-world business operations for contractors.
Connect with Sean Barry: https://leanscaper.com/
https://www.linkedin.com/in/sbarry/
Connect with Dwayne Kerrigan
Facebook
Instagram
Linked In
Website
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.

Most people treat sleep like something that happens to them. Dr. Michael Breus, aka The Sleep Doctor, treats it like a system — one that can be built, optimized, and recovered no matter how badly you've abused it.
In Part 2, Dwayne and Dr. Breus move from theory into full practice: the single morning habit that regulates your entire sleep schedule, the truth about supplements and peptides, and why a 78-year-old entrepreneur taking four different drugs to get through the day became drug-free in two weeks and now more productive than his staff can handle.
In this episode:
The one rule that regulates your entire sleep schedule
The three-15s morning routine: 15 deep breaths, 15 ounces of water, and 15 minutes of direct sunlight within 20 minutes of waking — and why vitamin D is a circadian pacemaker
The supplement framework most people get completely wrong
Dr. Breus's unambiguous position on peptides: lab-use-only compounds are being injected by people who have no idea what the 10 or 20-year consequences are, and the only thing he's ever found that he cannot fix without medication or intervention is physical pain and major mental health issues
How Dr. Breus accidentally became The Sleep Doctor: rejected from his first-choice sports psychology program, he sold himself into a sleep track, fell in love with clinical sleep medicine, and never looked back — "You change somebody's sleep, you change their life."

Discover Your Chronotype - Take The Quiz: https://sleepdoctor.com/pages/dr-breus-podcast-dwayne-kerrigan
Episode Highlights:
00:00 - Sleep Boosts Everything
00:22 - Podcast Welcome
01:24 - Wake Time Consistency
01:41 - Melatonin Timer Explained
03:12 - Minimum Sleep Safety
04:54 - Sleep Quality For Performance
06:41 - Exercise And Cooling Hacks
10:53 - Home Sleep Testing
14:51 - Sauna Timing And Cold Plunge
19:06 - Blue Light and Screen Stimulus
22:05 - Morning Sun Routine
23:51 - Supplements vs Bloodwork
27:50 - Magnesium Types And Research
30:24 - Avoid Over Supplementing
33:01 - Eight Hours Myth
34:42 - Modern Sleep Basics
35:40 - Kids and Teen Sleep
38:36 - What Good Sleep Feels Like
39:44 - Depression Meds and REM
45:29 - Entrepreneur Sleep Debt
49:39 - Peptides Sleep Shortcuts
54:36 - Sleeping Pills and Tapering
01:00:21 - Sleep Doctor Origin Story
01:04:03 - Sleep and Purpose
01:05:48 - Final Takeaways and Goodbye
Resources mentioned:
Take the Original Chronotype Quiz | SleepDoctor.com
Sleep Doctor At Home Sleep Test (SleepDoctor.com)

The Sleep Doctor At-Home Sleep Test provides clinical-level sleep analysis from the comfort of your own bed. Using two simple sensors and a connected app, users receive personalized results reviewed by a licensed provider in under a week.
Orion Sleep — mattress topper for temperature regulation
Eight Sleep — mattress topper referenced as comparable product
ChiliPAD — referenced as comparable cooling product
Full Script — Supplement Management & Lab Testing Platform
Andrew Huberman — referenced in context of the apigenin/magnesium threonate sleep stack
Dan Sullivan / Strategic Coach — case study referenced with permission
Laird Hamilton and Gabby Reece — referenced in context of sauna/cold plunge performance camp

Quotes:
“ Everything you do, you do better with a good night's sleep. Everything. There's not a single biological function that you don't do better when you sleep.” - Dr. Michael Breus
“ 25% of the people that show up on my doorstep, I have them go do blood work. As soon as we fix the deficiencies, they're done. They're gone. They don't need anything. But here's the funny part. Nobody has a deficiency in ashwagandha, right? Nobody has a deficiency in passionflower, right? Nobody.” - Dr. Michael Breus
“ God's delays are not God's denials. You know, you thought you wanted to be this, and you were pursuing this expectation or this hope or this dream, but then what you really found was your true purpose.” - Dwayne Kerrigan
“Wake up at the same time seven days a week. Notice I didn't say go to bed at the same time. I said wake up at the same time.” - Dr. Michael Breus
“ Sleep is the currency of attention. You cannot pay attention to anything if you're not well-slept. ADD, ADHD gets worse when you're not well-slept. You can't focus. Everything depe- this is why sleep is so fundamental to life, is because it's, it literally dictates what you look at, what you focus on, and where you spend your time. It's all comes from whether or not you got a good night's rest.” - Dr. Michael Breus

Dr. Michael Breus, Ph.D., is a double board-certified Clinical Psychologist and Clinical Sleep Specialist, and one of only 168 psychologists in the world to have passed the Sleep Medicine Boards without attending medical school. Known as The Sleep Doctor, he is the founder of sleepdoctor.com, was named the Top Sleep Specialist in California by Reader’s Digest, and one of the 10 most influential people in sleep, and is the author of several books including The Power of When and Sleep, Drink, Breathe: Wellness is Too Complicated. He has appeared on Oprah, CNN, The Today Show, and The Dr. Oz Show more than 40 times, and lectures globally for organizations including YPO and Tony Robbins' Unleash the Power Within.
Connect with Dr. Michael Breus:
YouTube: Sleep Doctor
Instagram: Sleep Doctor (@thesleepdoctor)
Take the Original Chronotype Quiz | SleepDoctor.com
Sleep Doctor At Home Sleep Test (SleepDoctor.com)
The Sleep Doctor At-Home Sleep Test provides clinical-level sleep analysis from the comfort of your own bed. Using two simple sensors and a connected app, users receive personalized results reviewed by a licensed provider in under a week.
Connect with Dwayne Kerrigan
Facebook
Instagram
Linked In
Website
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.