
Advertise on podcast: The Dwayne Kerrigan Podcast
Rating
4.8from
This podcast has
163 episodes
Language
EnglishPublisher
Dwayne KerriganExplicit
Yes
Date created
2023/09/20
Latest episode
2026/10/07
Average duration
71 min.
Release period
7 days
Description
Welcome to The Dwayne Kerrigan Podcast. Dwayne has navigated the business world for over 35 years, owning close to 30 businesses in 12 distinct industries. Today, entrepreneurship often seems more about glitz, glamour, and a celebrity venture. On this podcast, Dwayne collaborates with overlooked but accomplished entrepreneurs, delving into their journeys of forging exceptional enterprises. Join them as they share their personal journeys, lessons learned, and strategies that keep them moving forward. Let’s celebrate the true essence of entrepreneurship and inspire the next wave of business trailblazers.
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160. Building an Intentional Culture | FlyGuys CEO Joe Stough
2026/10/07
Joe Stough built a piece of software that ExxonMobil, Shell, and ConocoPhillips ran their worldwide safety operations on and he says none of it would have worked without a psychological framework he almost let disappear along with the mentor who created it. In this episode, he traces the throughline of intentional culture across three very different companies.
In this episode:
How Joe's early experience running Dynamic Systems International shaped the fundamentals he built his next company, Syntex, on — starting with hiring a lawyer on day oneThe Interpersonal Technology framework — eight personality styles built on Carl Jung's archetypes — that Joe credits for turning daily blowups with his first CFO into a working partnershipHow Joe's Impact software went from one language in one country to twenty-four languages in a hundred and eighty countries in a single year, landing ConocoPhillips, ExxonMobil, and Shell as worldwide clients within six monthsSelling Syntex to IHS in 2010 in an all-cash deal — and being pulled back to the office six months into "retirement"Why Joe took over teaching the Interpersonal Technology program himself after his mentor, Dr. James Gwaltney, passed away in 2016How FlyGuys runs an "Uberized" marketplace of over 22,000 drone pilots delivering data instead of rides or food
Time Stamps:
00:00 Intentional Culture Mindset
00:40 Podcast Welcome and Guest Intro
04:58 FlyGuys Business Model Explained
09:00 From Syntex to Waitr to FlyGuys
14:40 Early Failure Lessons Learned
20:09 Finding Mentors and First Investor
25:22 Interpersonal Technology Origin Story
31:25 Eight Personality Styles Overview
35:36 Thinking vs Feeling
36:17 Choicing and Dreaming Spectrum
37:12 Organizer vs Presenter Styles
38:06 Building Teams and Culture
39:38 Hiring for Strength Balance
40:50 Mentor Legacy and IP Story
48:47 Culture as Career Thread
52:35 Syntex Sale and Return
54:23 Global Data and Safety Index
01:00:20 Waitr Origin and Hypergrowth
01:04:53 Scaling Lessons and Replatforming
01:06:56 Wrap Up and Next Episode
About Joe Stough: Joe Stough is CEO of FlyGuys: a drone data collection company operating an Uberized marketplace with more than 22,000 pilots across the U.S. He founded Syntex in 1995, building the Impact software platform into what became a dominant operational excellence system used by companies including ExxonMobil, Shell, and ConocoPhillips, before selling the company in 2010. He later served as President and COO of Waitr, taking the food delivery company public on Nasdaq via SPAC in 2018. Joe now holds the intellectual property rights to the Interpersonal Technology framework and personally teaches it to leadership teams; he has been featured in Forbes, Fortune, and Entrepreneur Magazine, and sits on the board of Ducks Unlimited.
Connect: Follow The Dwayne Kerrigan Podcast for Part 2 of this conversation, and connect with Joe Stough and FlyGuys to learn more about the Interpersonal Technology program.
Connect with Joe Stough:
https://flyguys.com/
https://www.linkedin.com/in/joe-stough/
https://www.linkedin.com/company/flyguys.io/
Resources Mentioned:
Interpersonal Technology: The Art and Science of Personal and Professional Effectiveness by James A. Gwaltney (Author)
https://a.co/d/06TD2z2R
The Power of Goal ZERO: A Practical Leadership Guide for Achieving Superior Performance by Sam Smolik (Author)
https://a.co/d/06CjUZI2
The Daily Pursuit of Excellence: The 4 Keys to Achieving Superior Performance by Sam Smolik (Author)
https://a.co/d/03YXAfrQ
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.
159. The Space Between Fear & Action | Michelle “Mace” Curran
2026/09/30
At 500 knots each, two F-16s point straight at each other with less than a second to react, one of them upside down. That's the moment Michelle "Mace" Curran walks Dwayne through in Part 2 of this conversation, and it's just the entry point into a masterclass on what she calls "the space between": the pause between feeling fear and deciding what to do with it.
In this episode:
The near head-on collision during a Thunderbirds training pass, closing at roughly 1,000 mph, missing by what she believes was inches and the split-second decision-making that got both pilots through itWhy Michelle earned her call sign "Mace" (Mach at Circle Entry) by accidentally breaking the sound barrier on her second flight in Japan, and how she turned it into a badge of honorThe physical disruptor, wiggling her toes, that a flight instructor taught her to break out of over-control and hypervigilance, and the neuroscience behind why it worksWhy the Thunderbirds' hiring process (40 applicants, 3 spots, a 12-officer interview panel) weighs personality, composure, and preparation over raw technical skillHer "bubble" routine in her third year with the Thunderbirds, strict self-care boundaries that helped her show up better in a public-facing roleWhy she sees fear as a signal, not a stop sign, and how that reframe applies as much to a hard business call as it does to flying a fighter jet
Time Stamps:
00:00 Competence Over Noise
00:33 Welcome Michelle “Mace” Curran
01:32 Imposter Syndrome Pivot
02:53 Bravery And Fear Reframed
07:20 The Space Between
12:03 Near Miss Decision Making
14:54 Physical Disruptors Tool
21:56 Fear Signals In The Body
23:29 High Performance Discipline
29:01 Hiring For Team Traits
33:39 Thunderbirds Selection Process
36:20 Prep Under Pressure
37:13 Working Interview Signals
38:32 Downtime Reveals Drive
39:31 Bias and Perception Checks
41:15 Women in Fighter Aviation
47:13 Media Noise and Unity
50:58 Leading for Bigger Impact
54:56 Self Care for Performance
59:06 Where to Find Michelle
01:00:09 Call Sign and Failure Lessons
01:04:19 Final Thanks
Michelle "Mace" Curran is a former U.S. Air Force fighter pilot who flew as a Thunderbirds lead solo and trained the incoming opposing solo pilot during her tenure on the team. Over a 13-year military career she flew combat missions and instrument approaches in extreme conditions, including a station in Misawa, Japan. She is now a keynote speaker and author of the children's book Upside Down Dreams and its sequel centered on fighter pilot call signs, and has written a book exploring fear and decision-making under pressure. She also runs corporate workshops and speaks widely on high performance, fear, and leadership.
Connect with Michelle
Website: https://macecurran.com/
Instagram: https://www.instagram.com/mace_curran
LinkedIn: https://www.linkedin.com/in/macecurran/
Facebook: https://www.facebook.com/macecurran/
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.
158. Fighter Pilot to Founder | Michelle "Mace" Curran
2026/09/23
She's the second woman in history to fly lead solo for the U.S. Air Force Thunderbirds and she still describes her early years in a fighter squadron as "classic imposter syndrome." Michelle "Mace" Curran spent years running from failure before she realized what was actually driving her forward, and in this conversation with Dwayne Kerrigan, she pulls back the curtain on the debrief culture that rebuilt her confidence — and the messy, control-freak transition from single-seat cockpit to solo entrepreneur.
In this episode:
How a moment in the bookstore at the Smithsonian Air and Space Museum led, four years later, to Michelle's children's book What's Your Call Sign?Why Michelle calls her first Air Force assignment "classic imposter syndrome" — and how she learned to tell the difference between being pulled toward a goal and running from failureInside the Air Force flight debrief: how "root cause" and a single "lesson learned" sentence turn every flight — successful or not — into a team-wide teaching momentWhat changed when Michelle transferred to a reserve squadron in Texas right after it had debriefed a near-catastrophic mishapWhy leaving the military for entrepreneurship exposed her as, in her words, "a control freak," and what she's doing to build a real team instead of running her business like a one-person cockpitHow hitting the USA Today bestseller list with her book The Flip Side actually coincided with a dip in speaking bookings — and the lesson she took from it
Time Stamps:
00:00 Imposter Syndrome
00:24 Welcome
00:55 Meet Michelle “Mace” Curran
02:39 Why Kids Books
05:24 From Wisconsin To Jets
06:53 Advice For Parents
09:10 Pull Versus Push
14:48 Japan Pressure Cooker
18:39 Reputation And Legacy
21:25 Finding Your Team Role
23:35 Learning From Mishaps
26:32 Fighter Pilot Debriefs
31:32 Debrief Cadence Matters
32:40 Feedback Without Fear
34:36 Stacking the Odds
36:17 Solo Entrepreneur Shock
39:17 Delegation and Control
43:56 Trust Systems Not People
48:45 Building SOPs and CRM
52:17 Book Launch Reality Check
56:30 Entrepreneurship Fear and Freedom
58:49 Closing and Listener Takeaways
Michelle "Mace" Curran is a former U.S. Air Force F-16 fighter who flew as the fifth woman and second woman ever to fly lead solo with the U.S. Air Force Thunderbirds. She left active duty in 2022 after 13 years of service and founded Upside Down Dreams, a speaking, training, and education company. She is the author of three books, including the national bestseller The Flip Side, along with two children's books, Upside Down Dreams and What's Your Call Sign?
Resources mentioned:
The Flip Side (book)Upside Down Dreams (children's book)What's Your Call Sign? (children's book)
Follow The Dwayne Kerrigan Podcast for Part 2 of this conversation, and find more from Michelle "Mace" Curran.
Connect with Michelle
Website: https://macecurran.com/
Instagram: https://www.instagram.com/mace_curran
LinkedIn: https://www.linkedin.com/in/macecurran/
Facebook: https://www.facebook.com/macecurran/
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.
157. Spark of Trust | Keiron McCammon
2026/09/16
On this episode, Dwayne sits down with Keiron McCammon, host of Spark of Trust podcast, to unpack why that show exists in the first place. It starts with a wrong answer: Keiron went looking for what broke in 2022, blamed social media, and found something underneath it. Trust didn't collapse all at once, it broke in three acts over six decades: first our communities, then our institutions, then our information environment, each one stacking on the last, so no single fix, founder, or organization can repair it alone. Over the next hour and a half, Dwayne and Keiron dig into that unraveling, and why the honest response isn't a solution, it's a signal.
Time Stamps:
00:00 Welcome Keiron McCammon - Spark of Trust Podcast
01:36 Why Trust Matters
02:57 Tech Optimism to Disillusion
05:06 From Misinformation to Trust
06:14 Three Acts of Trust
09:54 Spark of Trust Mission
13:47 Community Pillar Questions
17:04 Neya
24:08 Institutions and Business Trust
30:27 Why Small Business Wins
34:20 Earning Trust Locally
35:19 Reimagining Broken Institutions
37:48 Community Care Lost
41:13 New Models in Healthcare
42:51 Building Trustworthy News
45:11 Tech Accelerates Misinformation
48:08 Internet of Humans
51:12 Trustworthy AI and Fiduciary Duty
57:26 Agents Bots and Identity
01:02:07 Optimism and Network Building
01:04:48 Podcast as Information Network
01:08:28 Dream Guests and Mission
01:09:32 From Listeners to Action
01:12:32 Building Trust Communities
01:18:36 Capital and Trust Tech
01:20:20 Mission-Proof Business Models
01:26:20 Honesty Builds Trust
01:28:02 Character and Consumer Power
01:31:53 Closing Reflections
If this conversation named something you've been feeling, share it with someone who needs it. And follow the show wherever you listen. It helps the right people find it.
Connect with Spark of Trust
https://sparkoftrust.com/
https://www.youtube.com/@SparkofTrust
https://www.linkedin.com/company/sparkoftrust
https://www.instagram.com/sparkoftrust/
https://www.facebook.com/sparkoftrust
https://podcasts.apple.com/ca/podcast/spark-of-trust/id6807994008
https://open.spotify.com/show/3XYhVqgSkTCGMpUYiRZDAQ?si=befe38707d834864
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.
156. Psychedelics, Ego & Success Hangover with Kelsey Kitsch
2026/09/09
Canada's top female entrepreneur two years running, flying between magazine covers and global stages and privately rocking on the floor with the door locked. Kelsey Kitsch, former CEO of Mind Cure and author of Success Hangover, sits down with Dwayne to unpack the ego that built her empire, the psychedelic experience that dismantled it, and what she found once the striving finally stopped.
Content Warning: This episode discusses psychedelics from personal experience. Dwayne and Kelsey explicitly state they are not promoting psychedelics. If you choose to explore this topic, please do thorough research, consult a medical professional, and ensure proper facilitation and integration support.This content is for informational purposes only.
This episode also touches on mental health and suicidal ideation. 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.
In this episode:
The three conditions Kelsey uses to unlock curiosity and better ideas, novelty, motion, and high emotion, drawn from researcher Mary Helen Immordino-Yang's workWhy Kelsey builds weekly goals instead of long-term SMART goals, and how her brother Trent Kitch's annual "goal card" shaped that thinkingThe battle between her "ego self" and "soul self" that played out over four hours in her first guided psychedelic experience and what was waiting on the other sideA breakdown of psychedelic experience levels, from psilocybin and MDMA to ayahuasca, San Pedro, mescaline, and 5-MeO-DMT, and what "set, setting, and sacrament" actually meanWhy Dwayne points listeners toward Dr. Dispenza's breathwork program as a non-psychedelic starting point, and the Othership app Kelsey usesThe reframe that closes the episode: "We can only feel loved in proportion to how much we're seen, and we can only be seen in proportion to how much we show people of ourselves."
Time Stamps:
00:00 Psychedelic Safety Disclaimer
00:42 Mett Kelsey Kitsch
03:30 Reinvention in a Changing World
05:13 Curiosity as a Career Compass
08:23 Play Framework for Creativity
16:34 Pattern Interrupts and Choice
19:48 Expectations Goals and Targets
30:23 Funeral Mindset and Daily Meaning
33:44 Opening Up About Psychedelics
35:32 Hustle Identity
36:31 Success Yet Empty
37:54 First Guided Journey
38:52 Sufficiency After Silence
41:15 Safety And Legality
42:22 Psychedelic Levels
44:44 Set Setting Integration
48:29 Breathwork Alternative
51:20 Beyond Woo Woo
59:39 Curiosity Over Protocol
01:03:10 Operating System Reset
01:04:58 Ego Versus Soul
01:10:04 Seen To Be Loved
01:13:01 Closing Remarks
About Kelsey Kitsch: Kelsey Kitsch is a Canadian entrepreneur recognized as the country's top female entrepreneur two years in a row and named to Canadian Business' Top 25 Under 35 and the Dell Women's Entrepreneur Network's Top 200 Globally. She started in construction at 15 in her father's business, later becoming President of Belvedere Place Development before founding Spark Play. She is the author of Success Hangover, delivered the TED Talk "Play Is the New PhD," and previously served as CEO of Mind Cure, a psychedelic-focused mental health company. She is now the founder of Paramont Love, focused on intimacy intelligence.
Resources mentioned:
Book: Success Hangover by Kelsey KitschTED Talk: "Play Is the New PhD" by Kelsey Kitsch
Connect with Kelsey Kitsch:
https://www.kelseykitsch.com/
Linked In
Connect: Follow The Dwayne Kerrigan Podcast for a new episode each week, and follow Kelsey Kitsch's ongoing work in intimacy intelligence at Paramont Love
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.
155. Curiosity, Play & the Art of Reinvention with Kelsey Kitsch
2026/09/02
Kelsey Kitsch was Canada's number one female entrepreneur two years in a row. She was on the cover of magazines, speaking at global economic forums, and building multimillion-dollar companies. She was also sitting on the floor of her locked office, in the darkest period of her life, wondering why none of it felt like anything. In Part 1 of this conversation, she and Dwayne explore what happens when the life you built no longer fits — and what it takes to build a new one from the inside out.
In this episode:
The three-factor brain state that produces your best ideas — novelty, motion, and high emotion — drawn from Mary Helen Imordino-Yang's research, and why Kelsey's most creative moments happen driving fast with the windows down in a place she doesn't knowWhy most people set goals wrong: Kelsey's case for short-term weekly goals anchored to a long-term direction, and why the deeper question isn't "what do I want to achieve?" but "who do I want to be when I get there?"Kelsey's experience with guided psychedelic therapy — the four-hour ego vs. soul battle she audio-taped during her first journey, and what it felt like to experience sufficiency for the first time: just being, without striving or driving or winningWhy woo-woo is a category problem, not an evidence problem — and how Kelsey frames breathwork and psychedelics the same way: repeatable patterns that produce consistent results, regardless of whether the mechanism is fully explained yetThe Othership breathwork app and Dr. Joe Dispenza's Marco Island program as non-invasive entry points for anyone curious about expanded states but not ready for psychedelicsThe single most important insight Kelsey has learned about love and being human: we can only feel loved in proportion to how much we're seen, and we can only be seen in proportion to how much we show of ourselves.
Content Warning: This episode discusses psychedelics from personal experience. Dwayne and Kelsey explicitly state they are not promoting psychedelics. If you choose to explore this topic, please do thorough research, consult a medical professional, and ensure proper facilitation and integration support.This content is for informational purposes only.
This episode also touches on mental health and suicidal ideation. 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 (audio):
00:00 - Psychedelic Safety Disclaimer
00:42 - Podcast Intro
01:13 - Meet Kelsey Kitsch
03:28 - Reinvention in a Changing World
05:13 - Staying Curious to Pivot
08:23 - Creativity Formula - Three Factors
16:34 - Pattern Interrupts and Choice
19:48 - Expectations Goals and the Golf Metaphor
25:16 - Identity Driven Targets and Daily Intentions
30:23 - Mortality Mindset and Showing Up Fully
33:43 - Opening the Psychedelics Conversation
34:32 - Driven to Deliver
36:31 - Success Yet In Crisis
37:54 - First Guided Journey
38:52 - Quiet Mind Breakthrough
41:15 - Safety and Legality
42:22 - Psychedelic Levels 101
44:44 - Set Setting Integration
48:29 - Breathwork Alternative
51:20 - Debunking Woo Woo
57:15 - Curiosity Beyond Protocols and Unknowns
01:04:58 - Ego vs Soul Battle
01:10:04 - Seen Known Loved
01:13:01 - Closing and Disclaimers
Resources mentioned:
Success Hangover — Kelsey Kitsch’s bookTED Talk: Play Is the New PhD — Kelsey KitschMINDCURE — psychedelic drug research company Kelsey co-founded
Overcoming Adversity: A Journey to Self-Alignment and Impactful Entrepreneurship with Sophia Plank
Part 2: Finding Balance: The Intersection of Self-Reflection and Business Growth with Sophia Plank
About Kelsey Kitsch:
Kelsey Kitsch is a Canadian entrepreneur, author, and founder who was twice named Canada's top female entrepreneur by PROFIT and Chatelaine. She built and led multiple multimillion-dollar companies including Belvedere Place Development, co-founded MINDCURE (a psychedelic drug research company), and is now the founder of Paramount Love (https://paramountlove.com/), focused on intimacy intelligence. She is the author of Success Hangover (published as Kelsey Ramsden) and has given a TED Talk titled Play Is the New PhD.
Connect with Kelsey Kitsch:
https://www.kelseykitsch.com/
Linked In
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.
154. Sound, Trust & Starting Again with Kate Bradley Chernis
2026/08/26
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 believeWhy 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 transcriptsThe "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 connectionHow Backline EQ outperformed the Microsoft/IBM/Google industry-standard language model (MFCC) by 70% in measuring team fit — using voice patterns alone, without transcriptionKate'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 againThe 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 LevitinThe Art of the Start — Guy KawasakiBackline EQ Live Conversations — Kate's audio salons, every other Thursday at 2:00 PM EasternMFCC (Mel-frequency cepstral coefficients) — industry language model standard Kate's technology was benchmarked against
Quotes:“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
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.
153. Vision, Entrepreneurship and Purposeful Growth with Mark Bradley (Re-release)
2026/08/19
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
Connect with Dwayne Kerrigan
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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.
152. Mission-driven Success: Integrity and Industry Disruption with Mark Bradley (Re-release)
2026/08/12
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
Connect with Dwayne Kerrigan
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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.
151. Exactly What To Say with Phil M. Jones (Re-release)
2026/08/05
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.
150. Gold, Oil, and the Cycle Nobody's Watching with Andrew Pancholi
2026/07/29
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
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.
149: Andrew Pancholi: What History Tells Us About Right Now
2026/07/22
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 nowThe 100-year pandemic cycle — how Spanish flu, cholera, and COVID all followed the same pattern, and why Andrew saw COVID comingThe 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 fascismThe 250-year empire cycle — America at a tipping point, the petrodollar's quiet expiry, and China's strategic expansion while the West was distractedWhy 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 LebanonThe 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 AndersonThe Secret Wealth Advantage — book by Akhil PatelThe Art of War — book by Sun TzuThe 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
Connect with Dwayne Kerrigan
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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.
148: Brian Will: Don't Sell to Private Equity Without This
2026/07/15
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
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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.
147: From Dropout to Multimillionaire: Brian Will's Success Formula
2026/07/08
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.
146: Why AI Empowers Entrepreneurs More Than Anyone with Sean Barry
2026/07/01
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/
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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.
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PhilGarza 2025/09/20
Dwayne is a 💎
⭐️⭐️⭐️⭐️⭐️
I recently had the privilege of meeting, chatting, and shaking hands with Dwayne Kerrigan. His genuine care for the people in his circle an...
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