Keep Hustling

In this episode of Keep Hustling, host Aaron Gordon welcomes the first second-generation guest in the show's history. Haley Thams is the owner and CEO of Plimsoll Media, the agency behind the video and social content for this podcast, and she is the daughter of Todd Thams from episode 65. She bought the agency from Bradley Flowers at twenty one, fresh out of college, having never worked a corporate job in her life. Her reasoning was that if she took a nine to five first she would never find her way back to entrepreneurship, so she chose the scarier option while she was young enough to recover from it. Aaron pushes on why someone already running a company would add teaching early morning cycle classes, and the answer turns out to be about isolation rather than ambition. The conversation then gets unusually honest. Aaron gives her live on-air criticism about undercharging for work she keeps absorbing, she defends why she does it, and neither of them backs down. She closes with the line she lives by: show up before you're ready.

Get To Know Haley Thams

Haley Thams is a Midwesterner with a passion for content, and the owner and CEO of Plimsoll Media. Whether a brand is starting from scratch or already has a built following, she makes the work personal.

She grew up in Iowa and is a graduate of Iowa State University's Greenlee School of Journalism and Communication, with a degree in Public Relations and Business Marketing. Some of her proudest work at Iowa State was writing for the Iowa State Daily, building her own online portfolio, and working as an intern. She finished her degree a semester early in December 2022, and the next month, at twenty one, she bought Plimsoll Media from Bradley Flowers, before she had ever worked a corporate job.

Nearly four years later she runs the agency from Chicago. Plimsoll handles strategy-led media days, short-form and long-form capture, content systems and distribution, workflow automation, and ongoing advisory built on real performance data. Among its clients, Plimsoll produces the video and social content for this podcast and for Aaron's NY Risk Advisor channels.

Since May 2025 she has also taught cycle classes at SALT Fitness Chicago, where her TikTok, @haley_thams, has built a following of more than 3,000 riders and fans.

Haley is the first second-generation guest in Keep Hustling history. Her father, Todd Thams, is episode 65, Maintaining The Hustle. Bradley Flowers, who founded her company and later sold it to her, is episode 4, Finding Freedom Through The Hustle.

Website - https://plimsollmedia.com/

LinkedIn - https://www.linkedin.com/in/haley-thams/

Instagram - https://www.instagram.com/plimsollmedia/

Tik Tok (Plimsoll Media) - https://www.tiktok.com/@plimsollmedia

Tik Tok (Haley) - https://www.tiktok.com/@haley_thams

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3 Key Listener Takeaways

1. Show up before you're ready. Haley's closing line is the whole episode in five words. She is candid that she carries imposter syndrome, does not know everything, and is not the best at any one thing, but she shows up present and ready to work anyway. The alternative, waiting until you feel qualified, is how people end up twenty years down the road regretting what they never tried.

2. Most people will give you a chance. The job is not to waste it. Aaron reveals a phone call that happened before the sale, where Bradley told him he was fairly sure Haley would figure it out. The client base stayed because they trusted the handoff. Aaron's point to any young person listening is that the chance is usually there for the taking, and the fear of being too young or not being taken seriously is mostly self-inflicted.

3. Saying I will figure it out is good business. Doing it for free is not. This is the sharpest exchange in the episode. Haley will learn anything a client needs rather than hand them off, which is exactly why she keeps clients. Aaron tells her live on air that she is terrible at pricing that work, and that doubling a workload without adjusting the fee is bad hustle. She pushes back that she does not want to charge people who believed in her early. Both positions are worth hearing.

Show Overview

00:00 The first multi-generational guest in show history

01:26 Who Haley is and what Plimsoll Media does

01:52 Why add spin instructing on top of running a company

02:10 The isolation nobody warns you about with remote work

03:16 Moving to Chicago knowing exactly one person

04:22 Not joining the class, leading it

05:26 Why this was never about a second paycheck

07:07 Buying a business at twenty one

07:23 The deal with Bradley Flowers, and no corporate job ever

08:42 If I take the nine to five, I never come back

09:24 Should more young people take the swing

10:11 No systems, no processes, no idea how the money worked

11:00 The people who quit just short of the goal

11:29 The phone call Bradley made before the sale

12:28 Most people will give you a chance, do not blow it

13:39 The three clients who stayed through four years of figuring it out

14:20 The client who almost left for a bigger agency

15:46 Saying no versus saying I will figure it out

16:12 Going behind the curtain on what she charges

17:03 You doubled the workload and never raised the price

17:23 Why she will not bill the people who believed in her first

18:34 Being Todd's daughter at an industry conference

19:13 Why she bought a business instead of starting one

21:13 It is not what you know, it is who you know

21:47 Taking Plimsoll outside the insurance industry

23:41 Show up before you're ready, and a line from Mark Twain

In this episode of Keep Hustling, host Aaron Gordon does something he has not done in 156 episodes. He interviews a guest he cannot see, whose voice has been altered, and whose name he does not know. The Salty Adjuster is a career catastrophe claims professional who launched a podcast in May 2026 and was inside Apple's Top 100 in the Careers category in two countries within the first month, without ever revealing an identity. The anonymity started as job protection and turned into the product. With nothing to run past HR or legal and no corporate image to protect, the show calls itself the claims conversation unfiltered, and Aaron digs into what that freedom actually buys. They get into what the public gets wrong about claims adjusters, why a claim is a legal contract rather than a payday, and the two hardest days in the work: underpaying someone who deserved better advice, and paying someone who did not deserve it at all. The Salty Adjuster also explains the strange math of a double life, where a side hustle nobody at work can know about gives back more energy than the day job takes.

Get To Know The Salty Adjuster

There is no personal bio for this guest, and that is by design.

The Salty Adjuster is a career catastrophe claims professional who hosts anonymously. The identity stays hidden for employment reasons, because the day job employer does not know the podcast exists. Aaron has never met the Salty Adjuster and would not recognize the Salty Adjuster on the street.

The show is the claims conversation, unfiltered. It blends humor, hard-earned wisdom, industry insight and authentic storytelling about the people and issues shaping claims, with conversations spanning catastrophe response, careers, leadership, burnout, technology, mental health and the very human work of helping people recover after loss.

It launched in May 2026 and found its audience almost immediately. Within its first month on the air it ranked among the Top 100 Apple Podcasts in the Careers category in both the United States and Canada, a category with more than 12,000 shows. Listeners now tune in from more than 32 countries, and the audience runs across adjusters, carrier and TPA professionals, restoration experts, insurance leaders and entrepreneurs. In October 2026 the show was named a finalist for the 2026 Signal Awards in the Best Trailer category.

Guests have included Bryan Falchuk, best-selling author and President of PLRB; Meg McKeen, founder of Adjunct Advisors; workplace mental health leader Cal Beyer; Chris Luiz, CEO of Scout InsurTech; Laurel Jordan of Datos Insights; Tony Cañas of Insurance Nerds; and two names Keep Hustling listeners already know, Michael Balarezo from episode 149 and Curtis Goldsborough, LO$$ RATIO, from episode 75.

The show is produced by CoVerse Communications, founded by executive producer Brett McKenzie, the Producer Brett referenced throughout this episode. The team also includes associate producer Heather Blevins, known in the industry as The Insurance Rebel, assistant producer Sophia Fouse, Dan Jackson on creative and production, and visual designer Quinn McGowan.

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3 Key Listener Takeaways

1. Going around the box beats living inside it. Most people hear the rules and ask how much of their idea will survive them. The Salty Adjuster treated the corporate guardrails as irrelevant rather than binding and built the thing anyway, just without a name attached. Aaron calls that a unique spin on the hustle, and the key is that nothing about it is dishonest or illegal. It is simply a refusal to accept that the only options are permission or silence.

2. Nobody in claims is trying to beat you. The line that should travel furthest out of this episode is that none of it is personal. Claims have been paid to people the adjuster would never socialize with, and denied to people the adjuster genuinely liked. The best possible outcome is nothing out of your pocket beyond the deductible and nothing extra into it either, because being made whole is the entire job.

3. The right side hustle pays you back in energy. The usual assumption is that a second pursuit drains the first. Here it runs the other way. A recording day that starts with exhaustion ends with enough momentum to carry the rest of the workday, which is why the show survives alongside a full claims workload instead of competing with it.

Show Overview

00:00 A different kind of episode, and Aaron's disclaimer

02:03 Building something big with no spotlight on you

03:08 Aaron's producer Brett conspiracy theory

03:59 Team sports, a creative outlet, and employment reasons

04:38 The webcam question nobody wanted to think about

05:10 The freedom of never running it past HR or legal

05:49 Does your employer know you have a podcast

06:25 The kid who still wants to touch the hot stove

07:36 Three thousand people listen, and this meeting is about a file note

08:50 Everyone likes a good mystery

10:29 The parameters are not relevant, I will go around the box

11:15 What the public gets wrong about claims adjusters

11:44 A policy is a legal contract, not a payday

14:24 The underinsured total loss that could not be fixed

15:22 The mold that supposedly grew in eight hours

16:10 The angry text, and the homeowners who hug you in the ashes

17:15 Have we ever met

17:49 The team behind the show and a Signal Awards nod

21:27 The lamest superhero ever

22:30 When the side hustle hands the energy back

23:44 The way out is through

24:06 keep hustling

In this episode of Keep Hustling, host Aaron Gordon sits down with Harland Merriam, a Presbyterian pastor, a retired Army colonel with thirty two years of service, a real estate investor, and the author of Profit Seeks Purpose. Harland has spent a career asking people the questions they tend to avoid, and he has a name for the one that stops successful people cold. I have achieved everything I set out to achieve, so is this all there is? The conversation keeps circling back to an idea Harland calls the pause. Not quitting and not slowing down for its own sake, but stopping long enough to ask why am I doing this and who am I becoming, then letting the answer set the next direction. Aaron and Harland work through what the military teaches about trust and commitment, why a purpose can hold steady while an identity keeps changing, and what happens to a person whose entire sense of self is their job when the job goes away. Harland also explains why he facilitates a weekly mastermind of accomplished entrepreneurs, a room built for the doubts nobody posts on LinkedIn.

Get To Know Harland Merriam

Harland Merriam is an author, entrepreneur, coach, and Presbyterian pastor with more than fifty years of experience helping people discover purpose, develop character, and lead with integrity.

After decades of ministry, military chaplaincy, and leadership, Harland entered the world of multifamily real estate investing, where he discovered that many successful entrepreneurs share the same quiet question: "I've achieved success, but is this all there is?"

That question inspired his book, Profit Seeks Purpose, and continues to shape his work today.

Harland now brings together faith-driven entrepreneurs in small mastermind communities where they find clarity, encouragement, accountability, and the courage to take their next faithful step. His passion is helping leaders build businesses that not only create profit but also bless people, strengthen communities, and leave a meaningful legacy. He served in the Army Chaplain Corps with both Reserve and Active Duty units across thirty two years, achieving the rank of Colonel and finishing his military career as Division Chaplain in the 90th and the 75th Divisions. As a Presbyterian minister he led congregations in Martinsville, Virginia, Raleigh, North Carolina, Dallas, Texas, and Beaumont, Texas. He is also a graduate of Stetson University, where he majored in Mathematics and Physics, and where he now serves as University Chaplain. His real estate work includes a local portfolio of rental properties and a syndicated 129 unit apartment complex in Tallahassee, and he leads a monthly meetup that teaches local investors how to invest wisely and ethically. He and his wife Barbara, whom he has known since kindergarten, live in DeLand, Florida.

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3 Key Listener Takeaways

1. The pause is part of the hustle, not a break from it. Harland makes the case that the adjustments that matter almost always arrive after a deliberate stop and a hard question. Why am I doing this, and who am I becoming? Hustling harder in a direction you have never questioned is just passing time with more effort. 2. Your purpose can hold steady while your identity keeps changing. For years Harland answered the question of who he was with his title, chaplain and pastor. When the uniform came off, the purpose of serving people did not disappear, it expanded. Aaron and Harland agree that it is fine to define yourself by your work, as long as the work is not the only thing holding your purpose up, because careers end and purpose should not end with them. 3. Doubt belongs in the room. Quoting his friend Rabbi Hyman, Harland offers that faith and doubt are two sides of the same coin and you cannot have one without the other. That is the reason he facilitates a weekly mastermind of highly successful entrepreneurs, a space built for the failures, the errors, and the questions that never make it into the LinkedIn version of a life.

Show Overview

00:00 Meet Harland Merriam

00:42 Thirty two years of military service

01:40 The one word behind all of it

02:49 The pause and the question that redirect a life

03:12 What the military teaches about commitment

04:13 A mission bigger than today

05:02 Trusted with everything at twenty one

07:11 University chaplain, fifty years older than his students

08:07 Purpose stays, identity evolves

09:23 How to commit when purpose keeps changing

11:35 Taking off the uniform and expanding the purpose

12:09 The first chapter, a man who turns outward

13:54 Rabbi Hyman on faith and doubt

14:42 A mastermind where the LinkedIn mask comes off

16:05 Complete does not mean perfect

20:11 When the job becomes the whole purpose

22:20 Two 14ers in Colorado with his son

23:17 Profit and purpose need each other

24:20 Harland's closing quote

In this episode of Keep Hustling, host Aaron Gordon sits down with Dr. Bill Sodeman, a business coach in Toledo who spent more than thirty years inside dotcoms, nonprofits, and universities before building a business of his own. Aaron opens by reading a line from Bill's bio, an unwavering commitment to excellence, and asking where it comes from. The answer goes back to graduate school in the eighties and nineties and W. Edwards Deming's work on continuous improvement, the ideas Detroit passed on and Toyota and Honda built an era on. Aaron then catches something in how Bill talks about slowing down. Bill never says stop, he says pause, and Aaron names why that matters: a stop means you quit, while a pause still leaves room for a pivot. Bill makes the case for five or ten minutes of Lego as a real reset, explains why vacation is when he gets most creative, and tells the story of the art student who found better ways to be creative in business school than in the studio. He also has a question he puts to his students. Forget what could go wrong, what happens when everything goes right?

Get To Know Dr. Bill Sodeman

Bill Sodeman earned a Ph.D. in Strategic Management and Information Systems from the University of Georgia. He holds an MBA from Rollins College, and a BA in Studio Art from the College of William and Mary. He has served in a number of leadership roles during his 30 plus year career in dotcoms, non-profits, and higher education. His roles included Chief Information Officer, Chief Learning Officer, and Faculty President. As a management and information systems professor, and as a published author, he has examined topics such as the use of artificial intelligence and big data in human resources management; corporate innovation; ESG investing; and stadium naming rights agreements.

In early 2025, Bill established a Focal Point Business Coaching franchise in the Toledo area, in pursuit of his lifelong goal of building his own business. As a consultant and Focal Point Certified Business Coach, Bill advises and supports business owners and executives to achieve results they otherwise could not achieve on their own. His areas of expertise include leadership development, strategic planning and implementation, continuous improvement, emotional intelligence, coaching, mentoring, corporate training, and stakeholder management.

Bill works with pro bono clients at non-profit organizations, and is a board member for the International Veterinary Organization. He works out daily, and has competed in many running events, including an ultramarathon and several marathons. He likes to travel around the world, and continues to pursue his interests in urban architecture and photography.

His motto is "Ite Inflammate Omnia."

Website - https://billsodeman.focalpointcoaching.com/

Coaching Profile - https://focalpointcoachingohio.com/coaches/bill-sodeman/

LinkedIn - https://www.linkedin.com/in/billsodeman/

3 Key Listener Takeaways

1. A pause is not a stop. Bill never uses the word stop, he uses pause, and Aaron is the one who names why that distinction carries weight. A stop means you quit. A pause leaves every option open, including going back the same direction with more energy or turning a full one hundred eighty degrees. Aaron takes it one step further: thirty seconds of thinking before you fall asleep can change the direction of a life, and the people who treat the world as only stop or go are the ones who never reach the next level.

2. Continuous improvement is the whole game. The philosophy Bill picked up in graduate school is simple and almost nobody runs it. Do not wait for something to break before you make it better. You do not have to be at the top of your industry's technology, Aaron notes, you just cannot afford to be at the bottom, and the only way to stay off the bottom is to keep adjusting while things are still working.

3. Prepare for success, not just for failure. Bill calls it the lottery question. Nobody wakes up expecting to win, so when something enormous actually lands, people are unprepared for it. He trains students to ask what happens when everything goes right, because the person who assumes they will fail gets blindsided by their own win, while the person who has already pictured it can act the moment it arrives.

Show Overview

00:00 Meet Dr. Bill Sodeman

01:05 Where continuous improvement came from, Deming and Toyota

02:02 Why everyone says it and almost nobody does it

03:17 What losing your leverage looks like

03:52 Thriving in a world that will not slow down

04:21 Time blocking, journaling, and the Pomodoro timer

05:08 Why Bill says pause and never says stop

05:44 The AI device Aaron wants in his shower

06:08 Aaron on why a pause still allows a pivot

07:24 The case for five or ten minutes of Lego

09:05 If I retire, I expire

09:45 Aaron's client and the idea born on a honeymoon

11:32 The art student who got more creative in business school

13:10 A childhood on the move and twelve years in Honolulu

13:39 A dot com in Texas, a nonprofit in Massachusetts, teaching in three more states

14:09 Building a network from scratch in Ohio

16:35 Stay positive, and the cynic who flipped the script

17:31 Forget what could go wrong, what happens when everything goes right

18:32 The lottery question and why nobody prepares to win

20:41 Bill's closing quote, Winston Churchill

In this episode of Keep Hustling, host Aaron Gordon sits down with Jason Wright, founder of Intentionally Inspirational and an early adopter who was testing AI inside ActiveCampaign five or six years ago, well before most people had heard of ChatGPT. The feature was predictive sending, it beat regular sends by four to seven percent, and nobody cared at the time. What makes the conversation useful is that Jason has since talked himself down. Back in March he was telling everyone to get on the bandwagon or get left behind, working harder than he ever had in his life. Then he noticed that nothing goes straight up forever. His position now is narrower and more honest: AI is excellent where the answer is black and white, and useless where it is not. Ask it how many ounces are in a pound, not how to fix your marriage. From there they get into his book on crushing fear and self-doubt, the choose-your-hard argument for betting on yourself, and a long detour into cigars and bourbon that turns out to be about the same thing. He closes with four words: go or get off the pot.

Get To Know Jason Wright

Jason Wright is the founder and CEO of Intentionally Inspirational, the marketing and automation agency he launched in 2015. He did not start out as an AI guy. He started out as an entrepreneur who was tired of watching good businesses fail because of bad marketing.

It was not his first business. His first taste of entrepreneurship came at fourteen, running lawn care and landscaping, with more fishing tackle as the motivation. He was told to go to college, get a degree, and get a real job, so he did. After seven years in corporate America, he had enough for one lifetime.

He built Intentionally Inspirational on one belief: that small businesses and entrepreneurs deserve the same quality of marketing that big companies pay millions for. The difference, as he puts it, is that they actually do the work themselves. No white labeling, no outsourcing to an overseas team, no faking it until they make it.

Over the past ten years the agency has worked with more than 725 accounts across ActiveCampaign, GoHighLevel, MailChimp, ConvertKit and others, building hundreds of funnels, running Meta ad campaigns, and setting up email automation systems for service businesses.

Then AI showed up and changed everything. A few years back they were dabbling with machine learning features inside ActiveCampaign, well before the current wave. When it became clear this was not just hype, they went all in. Today the work comes down to two things: fixing the offer and filling the calendar with qualified leads, with AI and automation as the method rather than the point.

He is the author of The Backwards Route To Forward Progress: 7 Solutions For Crushing Fear, Self-Doubt and Limiting Beliefs. He also hosts the Intentional AI Daily podcast, where he shares practical AI strategies, real world workflows, and honest takes on where the technology is headed. He runs the Smoke, Flow & Grow community on Skool, where cigars, smoked meat, bourbon and a little bit of business get discussed around the fire pit. With his wife he recently launched Bluebird Keepsakes, making personalized keepsakes on three lasers. He lives in St. Marys, Georgia.

Website - https://intentionallyinspirational.com/

LinkedIn - https://www.linkedin.com/in/thejasonwright/

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3 Key Listener Takeaways

1. Put AI in its lane. Jason's test is whether the answer is black and white. Numbers, analysis, a screenshot of a program you have never opened, how many ounces are in a pound while you are cooking. All of that it handles instantly. Ask it about your marriage and you are, in his words, asking a pizza for advice. It can also argue with you convincingly while being wrong, so run everything past your own logic test.

2. Choose your hard. His answer to anyone stalling on a leap. You can live a hard life from trying something and having it fail, or a hard life working for somebody you hate inside a safe and miserable job. Either way it is hard, so pick the version you would rather be living. He has failed more times than he can count, and his wife stopped counting the business ideas a decade ago.

3. Culture is not a waste of time. The cigar lounge is what Jason calls the great equalizer, where a blue-collar guy and somebody extraordinarily wealthy sit next to each other and nobody cares who anybody is. Aaron adds the part that makes it rare: forty-five minutes where nobody reaches for a phone. Find your version, whether that is a fire pit, a fishing boat, or a golf course, because the ideas tend to show up there.

Show Overview

00:00 Meet Jason Wright

04:29 Cigars, bourbon, and business around the fire pit

08:19 Where AI helps, and the lasers at Bluebird Keepsakes

10:45 Getting AI to explain fourth grade math

15:34 Choose your hard

17:41 The cigar lounge as the great equalizer

22:11 What to smoke if you are just starting

26:07 Why culture changes your business life

28:01 Wrapping up with listener engagement

In this episode of Keep Hustling, host Aaron Gordon reaches Dr. Denise Nussbaum in Maui, where she has lived for ten years and has not left the island since 2019. She spent more than two decades as a professor and department chair studying inequality, identity, and trauma, and she walked away in 2016 when, as she puts it, the job shifted from teaching students how to think to teaching them what to think. That opens the episode: AI in the classroom, the software built to catch it and the software built to beat that software, and her standing challenge to students to walk into the building across campus called a library. Aaron pushes back usefully, arguing the tools should buy us time to think rather than excuse us from it. From there they get into her research years and a frank stretch on how the conversation around inequality has shifted since the nineties. The last third is the strongest. Identity, why most people never examine theirs until it is threatened, family you choose rather than inherit, and the question she says every twentysomething should ask in the mirror: who are you really?

Get To Know Dr. Denise Nussbaum

Dr. Denise "Neesey" Nussbaum is an author, sociologist, designer, and community advocate whose work is shaped by a lifelong curiosity about the forces that influence human lives: power, belonging, trauma, resilience, and the choices we make when pushed to our limits.

She earned her Ph.D. in Sociology in 1999 and spent more than two decades at Mt. San Jacinto College in Southern California, where she served as a Professor and Department Chair. Throughout her academic career, she taught and mentored hundreds of students, encouraging them to think critically about social inequality, prejudice, human behavior, and the lasting effects of trauma. These themes continue to influence both her storytelling and her community work.

Her debut novel, The Ashes Know Her Name, combines the tension of a global thriller with a deeply human exploration of survival, identity, and the consequences of the past. Her writing draws on her sociological perspective to create characters and conflicts rooted in real-life complexity.

Denise is also the founder of Aloha Ranch, established in 2019 to support houseless and vulnerable families in West Maui. With more than 40 years of experience working alongside marginalized communities, she brings compassion, insight, and a commitment to helping people rebuild their lives.

Through her writing and service, Dr. Nussbaum explores not only what happens to people, but what happens because of what happens to them.

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3 Key Listener Takeaways

1. Learn how to learn, not just what to learn. Her worry is not that AI exists. It is that AI makes intellectual laziness effortless. Her fix is unglamorous: do real research, read real books, go find the sources that did not come looking for you.

2. Time saved is only worth what you do with it. Aaron's version is that Waze handed back the hour you used to spend planning a route. Her counter is that dishwashers and washing machines made the same promise in the fifties, and the cup just refilled with more to do. The tool does not decide how that hour gets spent. You do.

3. Ask who you are before something forces you to. Most people never examine their identity, she says, because it is like water to a fish. Invisible until it is threatened. Her question for anyone in their twenties: who are you really, and do you actually like the thing you do every day?

Show Overview

00:00 Meet Dr. Denise Nussbaum

05:33 What to do with the time technology hands back

07:31 Settling arguments with the Encyclopedia Britannica

13:07 Learning the business from his mother

16:39 Why retirement hits male identity hardest

18:56 The girl who changed her name at ten

20:51 The summer the twins went to different camps

24:02 Why the road to resilience runs through denial

In this episode of Keep Hustling, host Aaron Gordon sits down with Ben Barbic, a recording artist, author, and real estate broker out of San Jose, for a conversation that starts with a pile of weight plates. Ben's house burned down in a forest fire when he was five. The plates in the garage were the only thing that survived, so he sandblasted them and lifted with them all through his teens. He still has them. Two years after the family rebuilt, an earthquake took the house again, the day before his tenth birthday. What he pulled out of all that was less toughness than a pattern: build, lose, build back better. It is why a song that does not land is just a reason to write the next one. Aaron and Ben get into finding purpose in pain without pretending to feel good about it, why progress beats goals, and how music became the one place Ben has ever felt fully in control. He closes on the line that has stayed with him for years: the more I practice, the luckier I get.

Get To Know Ben Barbic

Ben Barbic is a recording artist, author, and real estate broker based in San Jose, California. His memoir, Rise & Climb: Finding Purpose Through Pain, is out now. He has closed more than $250 million in real estate through his brokerage, and he has spent decades working across music, fitness, real estate, and personal development.

His music blends reggae and hip-hop. He records and produces out of Where Dreams Sail Studios, where he has worked with reggae legends and with artists nobody has heard of yet, and his songs reach listeners worldwide through streaming playlists. He released an official soundtrack album alongside the memoir, with songs written to match its chapters.

Rise & Climb is written for high performers and for anyone in the middle of rebuilding. Barbic's own rebuilding started early. A forest fire took his family's house when he was five, and the only things that came through it were the weight plates in the garage. He sandblasted them and lifted with them through his teens. Two years after the family rebuilt, an earthquake took the house again, the day before his tenth birthday.

What came out of that was a habit rather than a slogan: build, lose, build back better. He credits a great uncle who was still curious into his nineties with showing him what staying at something actually looks like.

He keeps a daily practice of gym work and mountain climbing, and he has read more than five hundred books. He speaks and mentors people working through hard stretches, and his position is that nobody has to pick one path.

Both of his children are musicians releasing their own work, his son on jazz piano and his daughter as a singer. A song by the three of them has not happened yet, but he says it is in order.

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3 Key Listener Takeaways

1. Harness the discomfort instead of numbing it. Ben's advice for anyone in pain does not start with feeling better about it. The energy inside discontent is usable fuel. The move is to add one small thing you actually want for yourself, a walk, a run, anything, rather than reaching for whatever dulls it. It does not have to be a grand undertaking and you do not have to be happy about it.

2. Progress beats goals. He believes in goals, but he lives on progress, which is why he does not plan on retiring from what he is trying to accomplish. Framed that way, a song that does not land is a reason to make the next one rather than evidence the work was wrong.

3. The more you practice, the luckier you get. His closing quote, and his answer to anyone who calls somebody else's success luck. Keep showing up at the thing and the breaks start arriving. That is not luck. That is volume.

Show Overview

00:00 Meet Ben Barbic

05:55 The moments that shape you before you notice

09:29 Why a setback flips a switch instead of shutting one off

10:27 What to do when you are the one in pain

14:07 Music as the place he goes when life is chaos

18:01 What makes an artist easy to produce

21:37 The emotional spectrum we all share

24:28 The closing quote

In this episode, host Aaron Gordon sits down with entrepreneur and agency founder David V. Kimball to discuss the evolution of curiosity-driven side hustles and how experimentation, failure, and adaptability fuel long-term success. David Kimball shares how his early days building websites and following his interests taught him the value of persistence, even when instant results don't materialize. The conversation covers the importance of automating and outsourcing to free up time for what truly matters, the need for business owners to balance privacy concerns with technological progress, and how "creating more than you consume" can be a powerful catalyst for growth. They touch on the future of AI, responsible automation, and the temptation to over-optimize at the expense of meaningful experiences. David Kimball urges listeners to audit their routines, embrace tools that amplify their potential, and remember that true freedom requires self-discipline. The episode ends with an inspiring quote about moral restraint and an encouragement to always keep hustling.

Get To Know David V. Kimball

David V. Kimball is co-founder and CEO of lilAgents, where he leads strategy, SEO, and content. He is a digital marketer with more than 15 years of experience and a B.A. in Communication from Northwest University. He has led teams across software, staffing, and creative work, with a consistent focus on quality-of-life improvements for non-technical audiences.

Kimball lowers the barrier between people and the tools they need. Sometimes that means showing someone a tool that already exists. Sometimes it means making the tool itself. He is obsessed with process, platform agnosticism, and building new things that people can actually use.

At lilAgents, the agency he co-founded, the team builds AI systems for business owners so their time can go back to running the company and closing deals. Everything the agency builds is owned by the client rather than rented from the firm. The work is designed to compound, becoming more valuable over time instead of more expensive. Kimball describes the model simply: the team are the mechanics, not the landlords.

Part of that work is orchestrating AI agents to build and ship software. Examples of what he has built include award-winning apps that took first place in Netlify's Hot App Summer for shipping 30 open-source tools in 30 days, and first place in the CloudCannon and Astro challenge. He created Vault CMS, which lets writers publish an Astro website from Obsidian and is referenced in Astro's official docs, with 369 stars on GitHub. He also built Astro Modular, a blog theme for people who want a place online that belongs to them without building one from scratch, with 228 stars on GitHub. Across 21 Obsidian community plugins and his other public work, he has 861 GitHub stars. He has presented at Mike Schmitz's Practical PKM community, Hannah Siegertsz's Shipyard, and The Build Exchange, hosted by the AI Institute for Life Improvement in Tacoma.

Before lilAgents, Kimball spent 15 years in tech and marketing, including startup work at Gigster and Virtasant, six years of enterprise work at TrueBlue and Microsoft, and additional agency, indie games, and freelance roles.

He has worked remotely since 2018 from the Pacific Northwest, where he lives with his wife and kids. On his blog he writes about productivity, tech, and whatever he is working on. He builds with AI tools every day.

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3 Key Listener Takeaways

1. Create more than you consume. David drives home the power of shifting from passive consumption to active creation. Build, make, or invent, as a hobby or a new venture, and you unlock unexpected potential and greater fulfillment, regardless of current skill level.

2. Failure is not fatal. Pivot and persist. Aaron and David both stress that setbacks, failed ideas, and experiments are part of progress. The willingness to try, fail, adapt, and keep moving is how personal and professional evolution actually happens. Every misstep can become a stepping stone.

3. Harness curiosity and technology. This episode treats a curious mindset as a competitive advantage. David shows how embracing tools like AI and automation, while understanding their boundaries, helps people and businesses reclaim time for what matters most, keep innovating, and stay ahead in a rapidly changing world.

Show Overview

00:00 Curiosity and the drive to create

06:37 Learning from social media failures

09:37 Challenges of marketing strategies

13:32 Balancing automation and human effort

14:32 Fears and realities of automation

17:39 Privacy and tech solutions

22:59 Internet access and evolving knowledge

27:06 Wrapping up with listener engagement

27:38 Goodbye and encouragement

In this episode of Keep Hustling, host Aaron Gordon sits down with Michael Balarezo to talk through his path from Miami to claims work, Silicon Valley engineering, and a life in Colorado. Michael has seen insurance from both sides of the desk. He started as an all-lines adjuster, then built software for companies that included Google, Amazon, and Disney. In December 2021 the Marshall Fire hit his Boulder home. His family lost nearly everything on the main level and upstairs. The claims and rebuild process that followed felt like a second full-time job for two years.

That experience changed how he treats people in the process and why he co-founded Adjusto, the autopilot for contents claims. He walks through the scramble of evacuation, why the right coverage has to be in place before the smoke reaches the driveway, and how little most consumers are ever taught about their policies. The conversation gets into the hard realities of a claims system built for one house, not a thousand at once, and why the industry needs better tools as disasters arrive every year instead of once a decade. Michael closes with the Galaxy Quest line that became his working rule: Never give up, never surrender.

Get To Know Michael Balarezo Michael Balarezo is co-founder and CEO of Adjusto. An American software developer, futurist, and insurtech entrepreneur based in Boulder, Colorado, he is building recovery infrastructure for the disaster era.

He has seen personal property loss from every seat. After college he worked claims as an all-lines adjuster, then moved into software engineering in Silicon Valley. He spent eight years in engineering and technical leadership at MightyHive before serving as Global VP of Enterprise Automation at Media.Monks, where he led internal automation and AI strategy.

The Marshall Fire showed him how contents claims break carriers at both ends of the book. Most claims are small, under $5,000, and adjuster time often costs more than the payout. Large losses consume entire teams for months while families wait. When a catastrophe hits, both problems compound. Experienced adjusters get pulled to the fires, and the everyday claims behind them sit and rot in the queue.

That is why Balarezo co-founded Adjusto in 2024 with James Terry and Reid Greer. One platform handles the full severity spectrum. Small claims resolve touchless in hours. Large losses get world-class orchestration backed by the patent-pending FairMatch valuation engine, which pairs adjuster logic with market consumer data, plus TPA-enabled field services. Every claim gets exactly the treatment it needs.

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3 Key Listener Takeaways 1. Preparation meets peace of mind. Michael's calm during the Marshall Fire evacuation came from work done early: documenting possessions and understanding the policy before the crisis arrived. Knowing your coverage and keeping it current is the difference between panic and a plan.

2. Empathy from experience. Moving from adjuster to claimant put him inside the stress and emotional swing policyholders live through. Seeing both sides of the process made empathy nonnegotiable, for people in the industry and for anyone catching one of life's curveballs.

3. Never give up, never surrender. Whether you are fighting through an insurance claim or rebuilding after a total loss, the episode lands on persistence, adaptability, and a refusal to quit as the hustler mindset that gets you through adversity.

Show Overview 00:00 Getting into insurance in Colorado

04:53 The role of insurance adjusters

07:25 Understanding insurance for big purchases

11:41 Escaping the wildfire emergency

15:40 Insurance and peace of mind

16:22 Importance of early preparation

22:45 Being open about past roles

25:58 Addressing industry challenges with empathy

27:30 Recognizing outdated claims processes

In this episode of Keep Hustling, Aaron Gordon welcomes Mark Lewis, author of Give a Damn: The Ticket to Cultural Change. They discuss the importance of serving others, the impact of small positive actions, and how empathy and intentional engagement can transform both professional and personal lives. Mark Lewis shares insights from his experience running CEO roundtables, his book's core principles, and how technology is eroding face-to-face interactions. They highlight the value of fostering meaningful connections whether at work, in families, or through community and religion, and address barriers to cultural change including negativity and ego. The episode closes with Mark Lewis's motivational quote: "Individually, you make a difference. Collectively, we change the world."

Get To Know Mark S. Lewis Mark S. Lewis is CEO of Evolve Media AI, a professional speaker, leadership coach, CEO Roundtable facilitator, and best-selling author of Give A Damn! The Ticket to Cultural Change. He is a senior executive with a proven track record of building, leading, and guiding organizations, teams, and executives through growth, acquisition, and turnaround.

Mark co-founded the first locally owned Internet services company in New Orleans and grew its revenue from zero to nearly $4 million in less than three years. He established three remote branch offices, forged strategic partnerships with local exchange carriers, and helped negotiate the company's sale to a Fortune 1000 firm. He later merged three start-ups into a single entity, driving a 30% revenue increase in just two months, then negotiated the multi-million-dollar sale of that combined company to a wireless Internet provider.

His experience spans leadership coaching, sales and marketing, new business development, strategic planning, finance, and operations across both start-ups and established companies. He has led IBM agent firms in developing sales and marketing plans that improved profitability and designed a successful turnaround strategy that rescued a nonprofit organization from bankruptcy. Since 2014 he has implemented and moderated more than 25 CEO Roundtables.

Mark's contributions have been widely recognized. He was named Technology Leader of the Year in Louisiana by the Governor's Office, selected as the Marshall Klein Entrepreneur of the Year by the Entrepreneurial Organization of Louisiana, and honored as Rising Tide Small Business of the Year in Technology by the New Orleans Chamber of Commerce. In 2023 he was recognized nationally as a Leadership Coach by the Coach Foundation.

Results-oriented and focused on accelerating both growth and fulfillment, Mark continues to help businesses and individuals stay on a clear path to success.

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3 Key Listener Takeaways

1. Serve Others to Serve Yourself Mark Lewis shows that lasting success grows from putting the needs of others first instead of chasing personal gain. A mindset of service and empathy leads to deeper personal fulfillment and stronger internal well-being in both business and life.

2. Small Gestures Create Culture Throughout the conversation Mark demonstrates how simple, thoughtful actions such as saying "please" and "thank you" or holding a door open can lift organizational and personal cultures. These everyday behaviors create a powerful ripple effect that improves relationships, positivity, and even health and happiness.

3. Make Connection a Priority The episode underscores the cost of letting technology crowd out real interaction. Aaron and Mark both stress the importance of protecting time for authentic, in-person communication through family meals, community involvement, or workplace collaboration so people can build deeper connections and a more balanced life.

Show Overview 00:00 Discovering connected family ties of guest and host in Syracuse

04:31 Improving interpersonal skills

09:13 Thoughtful company culture strategies

12:50 Discussing the importance of the Sabbath

14:58 Link between religion and longevity

17:25 Importance of Religious Legacy

20:19 Justifying wrong actions

24:37 Examining obstacles to happiness

27:35 Podcast sign-off and contact info