Kate Bradley Chernis spent over a decade figuring out how to use sound to make strangers feel like friends. At Sirius/XM, she was building 200-layer audio files for 30-second commercials. Next, she was infusing radio theory into a generative AI platform before most people knew what generative AI was. Now at Backline EQ, she's using the same instinct, that sound tells you things a transcript never could, to engineer human connection at scale. This conversation covers all of it: the neuroscience, the pivots, and the parts of the journey she rarely shares out loud.

In this episode:

• The theater of the mind and why it's the foundation of trust: when your brain constructs the story rather than receiving it passively, it taps into nostalgia, memory, and emotion — the three keystones of why we buy, connect, and believe
• Why your eyes lie but your ears don't — Kate's case that sound is the most honest and hardest-to-trick human sense, and what that means for AI tools that rely entirely on transcripts
• The "rules of radio" Kate embedded into Lately's AI — word choices like "remember" versus "don't forget" that trigger different emotional responses, drawn from her training in the neuroscience of music and parasocial connection
• How Backline EQ outperformed the Microsoft/IBM/Google industry-standard language model (MFCC) by 70% in measuring team fit — using voice patterns alone, without transcription
• Kate's vulnerable disclosure about a difficult period in her life after eleven years building a company and how her mother's reminder that she was a prodigy at six became the unexpected anchor that helped her begin again
• The investor who finally told her to stop inventing something new and just make existing technology better and how that single pivot made everything easier for the first time in over a decade

Content Warning: This episode includes a brief discussion of suicidal ideation. The conversation is handled with care and context, but we want our listeners to be prepared.

If you or someone you know is struggling, call or text 988 — the Suicide and Crisis Lifeline — available 24/7 in both the US and Canada.

Episode Highlights:

00:00 - Podcast Welcome and Content Warning

00:17 - Sound Design Obsession

01:20 - Meet Kate Bradley Chernis

03:32 - Kinder Egg Smuggling Story

04:13 - From Radio to AI

05:56 - Theater of the Mind

10:23 - Why Sound Builds Trust

12:36 - Building Lately Secret Sauce

15:23 - Voice Control and Trust

21:18 - Staying Human in AI

28:58 - Leaving XM and Starting Up

34:27 - Early Genius, Confidence and Reinvention

36:26 - Self Love and Authenticity

38:38 - Imposter Syndrome Scale

39:15 - Resume Exercise for Confidence

42:29 - Trusting Your Gut

44:10 - Loneliness and Standing Up

47:05 - Entrepreneurship Lessons

52:05 - Rebuilding The Village

56:19 - Backline EQ Pivot

01:01:37 - Patterns and the Bridge

01:06:49 - Collecting Data the Hard Way

01:09:56 - Sound As A Force

01:11:22 - Return on Collisions

01:13:20 - Saying No and Self Care

01:16:57 - Closing Thanks and Outro

Resources mentioned:

• This Is Your Brain on Music — Daniel Levitin
• The Art of the Start — Guy Kawasaki
• Backline EQ Live Conversations — Kate's audio salons, every other Thursday at 2:00 PM Eastern
• MFCC (Mel-frequency cepstral coefficients) — industry language model standard Kate's technology was benchmarked against

“Your eyes lie. They can lie to you, but sound doesn't.” - Kate Bradley Chernis

“Often people will focus so much on their life condition rather than, "No, I'm here for a reason. I just need to maybe alter the blueprint." That doesn't mean lower your expectations, it just may mean shift your standards. Shift the way you're gonna get there, timeline, trajectory.” - Dwayne Kerrigan

“You have to start measuring. You have to start collecting data.” - Kate Bradley Chernis

“I can make people I can't see feel like they belong. It's more than that. I can make you feel like with a conversation that is either as powerful or more powerful than if we were eye to eye in real life. That's how transcendent sound is. There's a magic there that is, well, it's magical. It's fantastical.” - Kate Bradley Chernis

“Entrepreneurship's f***ing hard. This is a gladiator sport. And there is no substitute for the constant and never-ending courage that you need to have inside this, this arena.” - Dwayne Kerrigan

About Kate Bradley Chernis:

Kate Bradley Chernis is an early Generative AI visionary who co-founded the first closed-data, proprietary machine learning and natural language processing platform in 2014. She is the co-founder and CEO of the Backline Network, which uses curated audio-only salons to capture real-time conversational dynamics and convert them into AI that predicts and engineers group chemistry at scale. Before her career in AI, Kate spent over a decade as a rock 'n' roll radio DJ, serving 20 million listeners daily as Music Director and on-air host at Sirius/XM. An early prototype of her technology delivered Walmart a 130% ROI year-over-year for three years.

Connect with Kate Bradley Chernis:

https://www.linkedin.com/in/katebradley

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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.

What happens when the business you built becomes too dependent on you to keep growing?

Mark Bradley, Founder and Chairman of LeanScaper and author of the newly released The Landscaper’s Operating System: Build a Landscape Company That Runs Without You, joins Dwayne Kerrigan for Part Two of a conversation about one of the most important transitions an entrepreneur can make: moving from being the person who runs everything to becoming the leader who builds a company capable of running without them.

Mark draws on decades of experience building, scaling, and evolving businesses to break down the disciplines that separate growth from sustainable scale. He shares why strong systems and processes matter, how a CEO’s role must change as the company grows, and why the ability to prioritize, protect your time, and develop capable people becomes increasingly critical at every stage.

The conversation also gets into Mark’s relentless approach to learning — seeking out experts, asking better questions, openly measuring progress, and refusing to let past success become a reason to stop improving. For Mark, better businesses are built by leaders willing to continuously evolve themselves alongside the organization.

That philosophy has shaped each chapter of his career. Mark scaled TBG Landscape from a backyard operation into one of North America’s Top 100 landscape contractors before co-founding LMN in 2009, creating the business-management software he wished had existed while running his own company.

Today, he is continuing that mission through LeanScaper, helping landscape business owners build stronger operations, better teams, greater profitability, and businesses that no longer rely on the owner to solve every problem.

His new book, The Landscaper’s Operating System, takes that mission even further, distilling decades of hard-earned lessons into a framework for owners who want to step out of the bottleneck and build a company designed to perform beyond them.

If you are trying to scale a business, lead at a higher level, or create something that does not require your constant involvement to succeed, this is a conversation worth revisiting.

You can access Mark's book here: https://book.leanscaper.com/

Time Stamps:

[00:00] Introduction

[01:24] Preframing the Landscape Industry

[02:15] Creating Software for the Landscape Industry

[10:22] Asking for Mentorship and Luck

[13:53] Mental Shifts in Transitioning to Software

[17:40] Overcoming Personal Overwhelm

[19:22] Impact of Personal Goals on Business Success

[21:57] Journey to Losing 140lbs

[24:05] Advice to Younger Self

[29:26] Initiating Landscape Management Network (LMN)

[37:13] Keys to Business Success

[43:00] Innovating Your Business Model

[50:50] The Importance of Being Feedback-Oriented

[53:25] The Role of Progress in Success

[1:01:45] Scaling from 1M to 30M in Revenue

[1:11:36] A Day in the Life of a CEO

[1:18:00] Thanks and Connecting with Mark Bradley

[1:20:08] Closing Remarks and Disclaimer

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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.

What does it take to build a business that is profitable, principled, and strong enough to scale?

Mark Bradley, Founder and Chairman of LeanScaper and author of the newly released The Landscaper’s Operating System: Build a Landscape Company That Runs Without You, joins Dwayne Kerrigan for Part One of a wide-ranging conversation on the decisions, disciplines, and operating principles that helped shape his career.

Mark’s path was anything but conventional. After leaving the nuclear industry, he entered landscaping and began building what would eventually become TBG Landscape, growing it from a backyard operation into one of North America’s Top 100 landscape contractors. Along the way, he developed a distinctly operator-driven approach to business — one built around understanding the numbers, choosing the right customers, investing in great people, and refusing to compromise on the standards required to build something sustainable.

In this conversation, Mark explains why not every customer is a good customer, why strong businesses need healthy margins, and why paying exceptional employees exceptionally well can become a competitive advantage rather than a cost to control. He also breaks down the importance of clear goals, disciplined budgeting, job costing, and measuring productivity so that business decisions are driven by facts rather than instinct.

At the heart of Mark’s philosophy is a simple idea: a better business should create better outcomes for everyone involved. Better customers create healthier margins. Healthier margins allow you to invest in better people. Better people deliver better work. And when the entire system is aligned, growth becomes far more sustainable.

That operating mindset eventually led Mark to co-found LMN in 2009 after recognizing that the business-management software his own landscape company needed simply did not exist. What began as a solution to an internal problem grew into technology used throughout the landscape industry.

Today, Mark continues that mission through LeanScaper, helping landscape business owners strengthen their operations, improve profitability, build more capable teams, and create businesses that are less dependent on the owner.

His new book, The Landscaper’s Operating System, brings together decades of those lessons into a practical framework for owners who want to build stronger companies with greater clarity, discipline, and independence.

If you are building a company and want to understand the fundamentals beneath sustainable growth — the customers you choose, the people you hire, the numbers you measure, and the standards you refuse to compromise — this conversation is a powerful place to start.

You can access Mark's book FREE here: https://book.leanscaper.com/

Time Stamps:

[00:00] Introduction

[00:35] Mark Bradley: TBG Landscaping Journey

[01:38] Starting a Business: Mark's Story

[07:34] Acquiring First Customers: Strategies

[13:17] Business Evolution: Landscaping Today

[14:03] Replicating Business Success: Insights

[18:41] Targeting Ideal Customers

[23:59] Maximizing Revenue Per Hour

[27:15[ Mindset: Abundance vs Scarcity

[29:33] Financial Management: Budgeting Tips

[32:55] Crafting a Solid Business Plan

[37:00] Preserving Company Culture During Growth

[42:10] Leadership's Role in Business Success

[46:06] Setting Strategic Business Goals

[47:53] Implementing Goals Across Your Team

[51:39] Earning Based on Results: A Business Philosophy

[54:54] Transition from Landscaping to Software Development

[57:20] Emphasizing the Role of Education in Business

[1:00:18] Entering the Software Industry: A New Venture

[1:06:48] Mindset Shifts for Software Business Success

[1:07:27] Announcement: 2 Part Podcast Series

[1:07:54] Future Podcast Topics Discussion

[1:09:00] Finding Industry Mentors

[1:10:33] Youthful Entrepreneurship: Learning the Ropes

[1:12:12] Tailoring Advice to Fit Your Business

[1:13:55] Closing Remarks and Contact Information

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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.

This episode is a re-release and features Phil M. Jones, a successful entrepreneur and speaker, who brings to light the significance of mastering pivotal conversational moments in sales and customer service for business success. Join us as we delve into strategies for overcoming and preventing customer objections, understanding decision-making processes, and enhancing customer journeys in diverse industries. We explore the necessity of identifying critical moments in a customer's journey, tailoring compensation to motivate sales teams, and the impact of mindset on professional growth. Phil provides practical advice on setting targets, using direct rewards, and resources for further learning in sales and business strategy.

An entrepreneurial success story and founder of 5 multimillion dollar companies, Phil M Jones is a strategic Advisor to pioneering leaders of the world’s biggest brands. The author of 7 best-selling books including the “Exactly” Book Series with over 2 million copies sold, he is the Producer of the “Most Listened To” Audiobook of all time and Innovator of the highly coveted “How to Persuade” audible production. To date, more than 800 different industries, across 59 countries and 5 continents, have benefited from his input. Phil recently joined a long list of global leaders who serve in residence at High Point University’s Access to Innovators Program. The program at HPU connects students with industry leaders for networking and mentorship opportunities. He joins Apple Co-Founder Steve Wozniak, Netflix Co-Founder Marc Randolph and many others.

For more info on Phil M. Jones; https://www.philmjones.com/ or https://exactlywhattosay.com/

Check Out Phil’s Books: https://www.amazon.com/stores/Phil-M-Jones/author/B0097DKWP4?qid=1510658902&sr=8-1&ref=ap_rdr&isDramIntegrated=true&shoppingPortalEnabled=true

Timestamps:

[00:00] Introduction

[00:38] Phil Jones Background

[05:02] "Exactly What to Say" Overview

[08:32] Mastering the Art of Asking

[13:41] Effective Communication Strategies

[18:01] Achieving Results vs. Being Right

[24:30] Traits of Successful Salespeople

[28:43] Enhancing Customer Experience

[31:45] Sales Training Fundamentals

[32:35] Mastering Product Knowledge

[37:15] Developing Sales Skills

[39:45] Cultivating the Right Attitude

[41:01] Ideal Sales Training Schedule

[49:15] Encapsulating Excellence in Sales

[51:30] Embracing Discomfort in Sales Training

[1:02:05] Critical Business Moments

[1:20:58] Preventing Sales Objections

[1:40:30] Connecting with Phil M Jones

[1:42:25] Outro

Connect with Dwayne Kerrigan

Linked In: https://www.linkedin.com/in/dwayne-kerrigan-998113281/

Facebook: https://www.facebook.com/businessofdoingbusinessdk

Instagram: https://www.instagram.com/thebusinessofdoingbusinessdk/

Disclaimer The views, information, or opinions expressed by guests during The Business of Doing Business are solely those of the individuals involved and do not necessarily represent those of Dwayne Kerrigan and his affiliates. Dwayne Kerrigan or The Business of Doing Business 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.

Andrew Pancholi doesn't hedge his calls. In Part 2 of his conversation with Dwayne Kerrigan, the cycles analyst behind Market Timing Report lays out exactly where he thinks gold and oil are headed next — the kind of specific, put-your-name-on-it targets most analysts avoid — plus the one year already circled on his calendar for the next real market correction, and why the pullbacks along the way are buying opportunities, not warning signs. Using research that traces back nearly a century, Andy breaks down which years tend to run hot, which tend to break, and the one he's watching most closely right now. Dwayne and Andy also dig into digital currency, BRICS, and whether replacing the US dollar would really just be a way to wipe out national debt — and Andy shares how a historical pattern tied to the Dust Bowl era points toward a coming boom in grain and commodity markets.

Episode Time Stamps:

00:00 Cycles Love Or Hate

00:22 Welcome Back Andrew Pancholi

01:23 Digital Currency Questions

03:40 Crypto Value And BRICS

05:06 AI Bots and Cycle Speed

07:01 NFTs Bitcoin and Scrutiny

09:55 Debt Reset and History

11:41 Future Of Money Risks

14:50 Market Timing Report

18:28 Risk Management Trading Edge

24:00 Market Outlook and Year Cycles

31:10 Gold Oil and Commodity Boom

34:22 Mississippi Grain Crunch

36:08 Gold Cycles Explained

36:53 Why Cycles Matter

40:54 Gold Targets and Pullbacks

42:56 Cycles vs Technicals

45:45 AI and Modern Warfare

53:13 Using AI for Research

58:14 Upside of AI Progress

01:01:28 Detaching From Tech

01:02:46 Where to Find Andrew

01:04:21 Final Takeaways and Wrap

Guest bio: Andrew Pancholi is the founder and CEO of The Market Timing Report, a global macro research service used by professional investors and portfolio managers to identify risk windows and periods of asymmetric opportunity. For over 40 years, he has forecast turning points in markets including the S&P 500, gold, oil, and Bitcoin using time cycle analysis built on the methods of W.D. Gann, Edward Dewey, and Ralph Elliott. He is co-author of the bestselling book Zero Hour with Harry S. Dent Jr. and a board member of the Foundation for the Study of Cycles. Before market timing, Andrew spent decades as a senior pilot for a major flag carrier airline, including roles as Training Captain and Training Standards Captain.

Resources mentioned:

Find Andrew Pancholi's daily cycle updates and forecasts at www.markettimingreport.com or on YouTube at Market Timing Report https://www.youtube.com/@markettimingreport

https://www.linkedin.com/in/andrewpancholi/

https://www.facebook.com/markettimingcyclesanalysis/

Instagram @andrew.pancholi

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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 1981, American hostages were released from Iran within hours of Reagan's inauguration. Forty-five years later — to within 30 hours — Andrew Pancholi told his subscribers an Iran conflict was about to begin. He was right. This is not luck. It’s mathematics — and in this conversation with Dwayne Kerrigan, Andrew breaks down exactly how cycle analysis works, what it's telling us about real estate, geopolitics, and the global economy right now, and what business owners and investors should be doing with that information.

In Part 1 of this episode:

• The 18.6-year real estate cycle: why we are currently at the same position in the cycle as 2007 — just before the Global Financial Crisis — and what the smart money did last time, and what to do now
• The 100-year pandemic cycle — how Spanish flu, cholera, and COVID all followed the same pattern, and why Andrew saw COVID coming
• The 90-year geopolitical cycle: how the polarization, rise of nationalism, anti-immigration sentiment, and challenges to global order we're seeing now mirror the 1930s decade almost exactly — including the economic conditions that led to the rise of fascism
• The 250-year empire cycle — America at a tipping point, the petrodollar's quiet expiry, and China's strategic expansion while the West was distracted
• Why Andrew predicted the Israel-Iran conflict to within 30 hours — the convergence of a 45-year cycle, a 90-year cycle, and a 36-year cycle, and why Netanyahu's personal history from the 1976 Entebbe raid has driven his policy decisions in Gaza and Lebanon
• The AI boom through the lens of cycles — why every major boom is fueled by new technology, and whether the return on investment can justify what's going in.

Note: This conversation is for informational and educational purposes only and does not constitute investment advice. Please consult a qualified financial professional before making any investment decisions.

Episode Highlights:

00:00 - Hidden Patterns Teaser

00:30 - Podcast Intro Setup

01:03 - Meet Andrew Pancholi

04:39 - Why Cycles Matter

07:06 - Real Estate Cycle

08:44 - Big Cycles 2029 Risk

12:15 - What Should We Do

15:38 - Seven Year Life Cycles

19:43 - Forecasting Iran Conflict

24:25 - Pandemic Cycle Evidence

29:29 - Boom Signals And Technology

35:45 - Real Estate Action Steps

40:09 - Timing the Property Cycle

41:38 - Strategy Over FOMO

43:25 - Cycle Experts and Herd Signals

45:53 - Geopolitics in 90 Years

48:44 - The 250 Year Empire Shift

58:11 - Petrodollar and BRICS Challenge

01:06:21 - China’s Resource Playbook

01:11:38 - War Outlook Russia Ukraine Taiwan

01:15:31 - What to Watch Next

01:18:01 - Wrap Up and Disclaimers

Resources mentioned:

• Zero Hour — book by Andrew Pancholi and Harry S. Dent Jr.
• The Secret Life of Real Estate and Banking — book by Philip Anderson
• The Secret Wealth Advantage — book by Akhil Patel
• The Art of War — book by Sun Tzu
• The Market Timing Report — markettimingreport.com

Quotes:

“The minute you start a conflict, a physical conflict, you have lost the war.” - Andrew Pancholi

“The markets are an indication of the psychology of the world. That's the way I've always been trained and always looked at it, is that it is gonna give you what the psychology of the world is looking at things from a economic standpoint.” - Dwayne Kerrigan

“ If you don't have to buy, keep saving, 'cause the chances are the house prices will come down, and then when we get to about 2031, 2032, that might be a good time to start looking.” - Andrew Pancholi

“ Religious texts, philosophical texts, they all hide mathematical patterns within them. There is something secret hidden away. I mean, it's an open secret if you go and study it, but there are some patterns and years, certain mathematical patterns that do repeat in the bigger picture.” - Andrew Pancholi

“ I put the, uh, message out on the Thursday evening to our subscribers saying, "This is gonna kick off, uh, I believe on tomorrow or, or Saturday," and it actually happened on Saturday. So depending on where you are in the world, it was maximum 30 hours out.” - Andrew Pancholi

Andrew Pancholi is the founder and CEO of The Market Timing Report, a global macro research service used by professional investors, portfolio managers, and family offices to identify risk windows and periods of asymmetric opportunity. For over 40 years, he has forecast turning points in markets including the S&P 500, gold, oil, and Bitcoin using time cycle analysis built on the methods of W.D. Gann, Edward Dewey, and Ralph Elliott. He is co-author of the bestselling book Zero Hour with Harry S. Dent Jr. and a board member of the Foundation for the Study of Cycles. Before market timing, Andrew spent decades as a senior pilot for a major flag carrier airline, including roles as Training Captain and Training Standards Captain.

Connect with Andrew Pancholi: https://andrewpancholi.com/

https://www.linkedin.com/in/andrewpancholi/

The Market Timing Report — markettimingreport.com

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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 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/

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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/

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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

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Linked In

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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.