Everyone is racing to adopt AI. Almost no one is asking the harder question: what kind of leader are you becoming as AI gets more powerful? Technology will not fix a broken culture or poor leadership. It amplifies whatever is already there.

In this conversation, David Carr sits down with two guests who think about this differently. Christopher Skinner, founder of Stealth Dog Labs, works at the intersection of AI, cognition, and leadership. Chris Wessling, The Process Dude, helps leaders escape the day to day by building systems that scale.

Christopher explains why AI is running on the wrong specifications, why it was never designed to listen, and the three legs every healthy relationship needs: safety, challenge, and investment. Chris brings the process lens, if there is pain in a business, there is a process problem, and shares how one discovery conversation uncovered a 700,000 dollar fix hiding in a company's estimates. Then Christopher shows how the words a company uses can reveal where it is really heading, sometimes years before the numbers do.

The takeaway: before you lean on AI, get an honest baseline of your culture, your communication, and your decision making. Then the tool can actually help.

Connect
Christopher Skinner on LinkedIn: https://www.linkedin.com/in/christopherjskinner/
Stealth Dog Labs: https://www.stealthdog.com
Connect with Chris Wessling, The Process Dude, on LinkedIn: https://www.linkedin.com/in/theprocessdude/


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Connect with Steward Your Business:

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• Call: +1 909.404.9865
• Website: https://stewardyourbusiness.com
• LinkedIn: https://www.linkedin.com/in/davidwcarr

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When a great employee leaves, most leaders assume it was about pay. Larry Salazar has the data to argue otherwise. The single largest contributor to the financial stress that drives turnover is housing, and almost no employer is doing anything about it.

Larry is the President and co-founder of NestSTEPS, a platform that turns home ownership into an employee benefit. In this conversation with David Carr he makes the business case: replacing an employee costs 50 to 200 percent of their salary, housing eats roughly a third of household spending, and financially stressed employees lose about 9 percent of their work time to money worries.

He shares the personal story behind NestSTEPS, leaving a company he loved because he could not figure out how to buy his first home nearby, and what a national study revealed: 78 percent of employees would switch employers for a home ownership benefit, and 89 percent would stay even after receiving help. Then he walks through exactly how the program works, from a financial wellness platform to live workshops to an employer funded contribution at closing, and how smaller companies can offer it through a PEO.

You will walk away rethinking what really keeps your best people, and what benefit could set your business apart.

Connect with Larry Salazar on LinkedIn: https://www.linkedin.com/in/larrysalazar/
NestSTEPS: https://www.neststepsbenefits.com
Sign up for Larry's newsletter: https://bit.ly/3OAGcp8


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Connect with Steward Your Business:

• Book a Leadership Clarity Call: https://calendar.stewardyourbusiness.com/cc
• Call: +1 909.404.9865
• Website: https://stewardyourbusiness.com
• LinkedIn: https://www.linkedin.com/in/davidwcarr

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When revenue slows, almost every company reaches for the same lever: more leads, more marketing, more pressure on sales. Ellen Smolko says that is usually the wrong move. Most revenue problems are structural, and more activity does not fix them. It just exposes the gaps.

Ellen is the founder of Foresight Performance and the Marketing Medic. In this conversation with David Carr she unpacks revenue friction, the term she coined for anything that quietly slows a company's growth, and her rule: diagnose before you do.

She shows how founders misdiagnose a slowdown, blaming the pipeline, then sales, then marketing, then buying a new website, while the real issue goes untouched. She shares a pricing pushback story where the client actually wanted to pay more, and an accounting firm that was losing clients until it lost the suits, got relatable, and then raised its prices. Then she lays out her four pillar revenue alignment framework: positioning and buyer fit, productization, pricing strategy, and scalability.

You will walk away knowing how to tell whether your revenue problem is really a leads problem, and what to look at instead.

Connect with Ellen Smolko on LinkedIn: https://www.linkedin.com/in/ellen-smolko/
Foresight Performance: https://foresightperformance.com
Free Revenue Friction Diagnostic: https://marketingmedic.pro/diagnosticfs


Become a supporter of this podcast: https://www.spreaker.com/podcast/business-roundtable--6049255/support.

Connect with Steward Your Business:

• Book a Leadership Clarity Call: https://calendar.stewardyourbusiness.com/cc
• Call: +1 909.404.9865
• Website: https://stewardyourbusiness.com
• LinkedIn: https://www.linkedin.com/in/davidwcarr

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For thirty years, getting found meant ranking on Google. That era is ending. People now ask ChatGPT, Perplexity, and Claude to recommend a business, and those tools only surface a few names. If yours is not one of them, your next customer never sees you.

Solomon Thimothy is the founder of Clickx, co-founder and CEO of OneIMS, and a USA Today and Wall Street Journal best-selling author who has spent two decades helping companies grow. In this conversation with David Carr he makes a blunt case: the founder's voice is now the growth strategy, and you cannot outsource it. If Oprah had outsourced her marketing, would Oprah be Oprah?

He shows why AI tools only cite the sources they trust, third party media and podcasts, and how to build a footprint that makes you the answer when someone asks the machine who to hire. Then it gets strategic: why 10X thinking is easier than 2X, why the product with your best margin is often the one you market least, and how AI agents can follow up with every lead on autopilot.

You will walk away knowing whether your business shows up where buying decisions are now made, and what to do about it.

Connect with Solomon Thimothy on LinkedIn: https://www.linkedin.com/in/solomonthimothy
Clickx: https://www.clickx.io
OneIMS: https://www.oneims.com


Become a supporter of this podcast: https://www.spreaker.com/podcast/business-roundtable--6049255/support.

Connect with Steward Your Business:

• Book a Leadership Clarity Call: https://calendar.stewardyourbusiness.com/cc
• Call: +1 909.404.9865
• Website: https://stewardyourbusiness.com
• LinkedIn: https://www.linkedin.com/in/davidwcarr

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Everyone celebrates the startup that raises a huge round and grows at all costs. Bryan Clayton built the opposite. He took GreenPal, the Uber for lawn care, past 10 million dollars a year with zero venture capital, and he argues that raising too much money before you have it figured out is more likely to kill you than save you.

Bryan is the CEO and cofounder of GreenPal. Before it he built a landscaping company to 8 figures and 150 employees and sold it. In this conversation with David Carr he is candid about what bootstrapping really demands, from cutting his own burn to under 4,000 dollars a month to getting belly to belly with his first hundred customers.

He tells the story of the insight that saved the company. Coming from lawn care, he was sure customers only wanted the cheapest price. Then he talked to them and learned the real pain was the disappearing lawn guy. People wanted reliability, and would pay more for it. From there he gets practical: why scaling is a video game where you must play your level, how to find the one limiting factor holding you back, and how to build an antifragile business that improves when you step away.

You will walk away rethinking what real, durable growth looks like.

Connect with Bryan Clayton on LinkedIn: https://www.linkedin.com/in/bryan-clayton-a96b33214/
GreenPal: https://www.yourgreenpal.com


Become a supporter of this podcast: https://www.spreaker.com/podcast/business-roundtable--6049255/support.

Connect with Steward Your Business:

• Book a Leadership Clarity Call: https://calendar.stewardyourbusiness.com/cc
• Call: +1 909.404.9865
• Website: https://stewardyourbusiness.com
• LinkedIn: https://www.linkedin.com/in/davidwcarr

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How much money do you actually need? Most people answer with a number. Dr. Nicholas Michels says that is backwards. Don't start with a dollar amount. Start with the life you want, then let the money serve it.

Nick is a CERTIFIED FINANCIAL PLANNER professional, founder of Michels Family Financial, and author of Rich by Choice. In this conversation with David Carr he gets honest about why so many people are outwardly successful and inwardly stressed, and how to close that gap.

He has lived both sides. He grew up comfortable until his family went, almost overnight, from a stay at home mom of four to a single mom working three jobs. Years later he had built real wealth as a fast rising advisor and still felt his happiness lagging behind his bank account. The turning point was a hard conversation with his wife and the humility to seek mentors. From there he shares the comparison game and the rocking chair test, why happiness comes from the steps and not the destination, how to 10X your business through your unique ability, and a legacy lens that reframes what money is really for.

You will walk away ready to design the life first and let the number follow.

Connect with Dr. Nicholas Michels on LinkedIn: https://www.linkedin.com/in/nicholas-e-michels
Michels Family Financial: https://michelsfamilyfinancial.com
Rich by Choice (free gift): https://richbychoicebook.com


Become a supporter of this podcast: https://www.spreaker.com/podcast/business-roundtable--6049255/support.

Connect with Steward Your Business:

• Book a Leadership Clarity Call: https://calendar.stewardyourbusiness.com/cc
• Call: +1 909.404.9865
• Website: https://stewardyourbusiness.com
• LinkedIn: https://www.linkedin.com/in/davidwcarr

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Your business is growing. That does not mean it is stable. For a lot of founders, growth quietly hides the problems that will break the company later, and you do not see it until it snaps.

Tracy Holland is a founder, investor, and operator who took HatchBeauty Brands from zero to 100 million dollars, then built a live selling business to 27 million in two years and sold it. She now buys distressed companies and rebuilds them, and she has worked with more than three thousand entrepreneurs.

In this conversation with David Carr she names founderitis and its symptoms, lays out the three decisions that put a business near bankruptcy, and explains why revenue can climb while the company gets weaker. Then it gets practical: why most founders built a job instead of a business, how to move from operator to owner, and the one skill worth more than any technical talent, going deep into your customer's pain until you can describe it better than they can.

You will walk away knowing what to look at first, and why if it is a money issue, it is not really an issue.

Connect with Tracy Holland on LinkedIn: https://www.linkedin.com/in/tracyholland
Tracy on Instagram: search Tracy M. Holland


Become a supporter of this podcast: https://www.spreaker.com/podcast/business-roundtable--6049255/support.

Connect with Steward Your Business:

• Book a Leadership Clarity Call: https://calendar.stewardyourbusiness.com/cc
• Call: +1 909.404.9865
• Website: https://stewardyourbusiness.com
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Most owners buy the AI tool, skip the strategy, and wonder why nothing improves. Jason Alexander, CEO of Chief AI, explains why AI is a people and process problem, not a tool problem.

Hand someone a guitar, and you still hear no music until you teach them to play. Jason has lived the operator side of this. Over 20 years, he built and scaled a staffing and consulting business to roughly 100 million dollars before selling, and now he helps founders turn AI into practical, measurable results.

In this conversation with David Carr, he breaks down the three-year success roadmap he uses to determine where AI actually belongs, why "assess, one quick win, then scale" beats chasing silver bullets, and how to make AI part of your culture rather than hiding it from clients. He also gives a straight answer on the fear everyone carries: AI is a force multiplier, not a layoff plan. Arm 100 people to produce 400, rather than cutting headcount to save payroll.

If you are a founder or leader trying to make AI pay off without losing what makes your business human, start here.

Connect with Jason:
ChiefAI: https://chiefai.co
Jason Alexander on LinkedIn: https://www.linkedin.com/in/jasonalexander
Free AI Readiness Score: https://chiefai.co/ai-readiness-assessment/

Become a supporter of this podcast: https://www.spreaker.com/podcast/business-roundtable--6049255/support.

Connect with Steward Your Business:

• Book a Leadership Clarity Call: https://calendar.stewardyourbusiness.com/cc
• Call: +1 909.404.9865
• Website: https://stewardyourbusiness.com
• LinkedIn: https://www.linkedin.com/in/davidwcarr

Watch more episodes  and subscribe on YouTube:
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You can have the right strategy, the right team, and the right systems. But if you are running on empty, none of it performs the way it should. And most leaders already know what they should do. They just do not do it.

Jalene Szuba is the founder of Happiness Anchor, a nationally board certified health and wellness coach, TEDx speaker, and Tulane University wellness consultant. In this conversation with David Carr she starts with sleep as a performance driver, not a lifestyle topic, then goes where most leadership talks never reach: why knowing better so rarely changes what we do.

She unpacks the Immunity to Change framework from Robert Kegan and Lisa Lahey, the same process she uses in her coaching and in research at Tulane. You will hear how hidden commitments and big assumptions work against your goals, one foot on the gas and one on the brake, why small tests beat massive overhauls, and why a healthy culture has to start at the top. Underneath it all is the Steward Your Business idea that the biggest constraints on a leader are internal, and they will not fix themselves.

You will walk away able to name the change you keep avoiding, and with a simple first step you can take tonight.

Connect with Jalene Szuba on LinkedIn: https://www.linkedin.com/in/jaleneszuba/
Happiness Anchor: https://www.happinessanchor.com


Become a supporter of this podcast: https://www.spreaker.com/podcast/business-roundtable--6049255/support.

Connect with Steward Your Business:

• Book a Leadership Clarity Call: https://calendar.stewardyourbusiness.com/cc
• Call: +1 909.404.9865
• Website: https://stewardyourbusiness.com
• LinkedIn: https://www.linkedin.com/in/davidwcarr

Watch more episodes  and subscribe on YouTube:
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Most business owners think PR is about getting featured. More placements, more visibility, more attention. Ronica Cleary says that is exactly where it goes wrong. Visibility without a strategy behind it is not a win. It is just noise.

Ronica is the founder and CEO of Cleary Strategies and a former White House correspondent who spent years in newsrooms before building her agency. In this conversation with David Carr she pulls apart what PR actually is, and why chasing placements so often backfires. Your business alone, she says, is rarely newsworthy. The real work is figuring out what is.

She walks through the period of discovery her team runs with every client, turning a founder's story into four to six clear pillars, why a guarantee of a set number of placements every month is a red flag, why she personally turned down a media hit that looked like an obvious fit, and how thinking like a producer instead of a publicist is the difference between a pitch that lands and one that dies in an inbox. Running underneath it is the Steward Your Business idea that PR is not just about getting attention, it is about being ready for it.

You will walk away able to tell whether your own message would hold up once it lands, and with a simple self-check to see whether you are even ready for PR.

Connect with Ronica Cleary on LinkedIn: https://www.linkedin.com/in/ronica-cleary/
Cleary Strategies: https://www.clearystrategies.com


Become a supporter of this podcast: https://www.spreaker.com/podcast/business-roundtable--6049255/support.

Connect with Steward Your Business:

• Book a Leadership Clarity Call: https://calendar.stewardyourbusiness.com/cc
• Call: +1 909.404.9865
• Website: https://stewardyourbusiness.com
• LinkedIn: https://www.linkedin.com/in/davidwcarr

Watch more episodes  and subscribe on YouTube:
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