Connect With Chaz

Dre Baldwin did not start playing basketball until he was 14. He played one year of high school ball, mostly from the bench. He walked on at a Division III school, a level that almost never sends anyone to the pros.

After college he sold gym memberships and worked at Foot Locker. Then he paid his own way into an exposure camp in the summer of 2005, played well, signed with an agent, and was playing pro ball in Lithuania a few weeks later. He played professionally for almost 10 years.

Today Dre runs Work On Your Game. He has written 11 books, spoken at TEDx four times, and built more than 48 million views on YouTube. In this conversation with Chaz Wolfe, he breaks down the mental toughness behind all of it, and how a business owner can use the same playbook.

KEY TAKEAWAYS

1. Quitting and pivoting are not the same thing. Dre walked away from baseball because he did not have the talent. He kept the goal and changed the vehicle. Owners do the same when a service line or a market stops working.
2. If it is not working, your formula may be wrong. When a business stalls, Dre says the strategy itself may be off. Find someone who already has the right information and learn from them.
3. Review your habits like employees. Every habit gets a review. Keep it, adjust it, or let it go.
4. Work backward from the goal. Dre calls it a reverse roadmap. Start with the result, then decide what has to be true at each step to get there.
5. Moderation is average. Dre says there is no neutral in life. You are either getting better or getting worse. Clear yes or no rules make hard decisions easy.
6. Invest in yourself early. His advice to his younger self is to start investing in himself as soon as possible, in what he learns and in who he spends time with.
   
   

If you are a contractor business owner and you want to make more money, work less, and win at home, we built something for you.

Go to gatheringthekings.com and apply for a GTK Growth Audit. We will show you exactly where you are leaking time, profit, and opportunity, and what it would take to fix it.

Connect with Chaz Wolfe (Host):

Website

Facebook

Instagram

LinkedIn

YouTube

Connect With Dre Baldwin:
Website: https://dreallday.com

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Share this episode with a friend and leave us a review on Apple Podcasts or Spotify!

Join the conversation by visiting GatheringTheKings.com and apply to connect with other high-performing entrepreneurs and their families.

Connect With Chaz

In 2018, Ryan Schmitt thought he was having a heart attack. He was cutting every dollar he could find in the business, and he was trying to decide whether to cancel the key man life insurance policy. He kept it. Because he was not sure he was going to make it.

The company he had built over a decade had just lost $7 million on one job. They had lost their bonding. He had borrowed $2 million from a colleague. He was staring at the ceiling every night.

He never had a single employee leave.

Today, 230 people work for Petticoat-Schmitt. They hear the financials every Monday at 3:30. They share in the profits. And Ryan is in the middle of converting the company to an ESOP so his people can own it.

That is where a valley of darkness can take you, if you walk into the punch every morning and refuse to stop.

KEY TAKEAWAYS

1. The most impactful project is often the one that nearly kills you. When Ryan was asked at a conference what his most impactful project was, he immediately named the one that lost $7 million. Not because it was successful. Because it changed everything about how he leads.
2. Tell your spouse first. Ryan's business group told him to go home and tell his wife before anyone else. She said, "as long as we're together, that's all that matters." That sentence became fuel for everything that came after.
3. Relationship capital is real capital. Two people showed up with money and resources when Ryan needed them. They said yes because they knew his character, not because the numbers looked good. That is what you are building when you build genuine relationships.
4. Transparency did not cause a stampede. Ryan shared the full financial picture with his team during the worst of it. Nobody left. In a good market where every other company was hiring, his people stayed. That is what a people-first culture actually produces under pressure.
5. Stop hiding in your office. Pre-crisis Ryan was head-down at his desk. He thought that was where he was most valuable. He was wrong. Post-crisis Ryan has no office. He shows up on job sites at sunrise with biscuits and questions.
6. Profit sharing changes the conversation. When employees see exactly how the company is doing and share in the upside when it performs, they stop being workers and start being partners. That shift is what made the rebuild possible and is what the ESOP is formalizing.
   
   

If you are a contractor business owner and you want to make more money, work less, and win at home, we built something for you.

Go to gatheringthekings.com and apply for a GTK Growth Audit. We will show you exactly where you are leaking time, profit, and opportunity, and what it would take to fix it.

Connect with Chaz Wolfe (Host):

Website

Facebook

Instagram

LinkedIn

YouTube

Connect With Ryan Schmitt:
LinkedIn: https://www.linkedin.com/in/ryan-schmitt-14866587/
Website: https://www.petticoatschmitt.com/
Facebook: https://www.facebook.com/petticoatschmitt
Instagram: https://www.instagram.com/petticoatschmitt/
YouTube: https://www.youtube.com/channel/UCPPhiL7wjPWpFPH30VqMcbQ

Support the show

Like what you heard?

Share this episode with a friend and leave us a review on Apple Podcasts or Spotify!

Join the conversation by visiting GatheringTheKings.com and apply to connect with other high-performing entrepreneurs and their families.

Connect With Chaz

Mike DeHaan was miserable for four and a half years as an engineer. One morning, driving to work in dead silence, he called his wife and said he needed to quit. She asked what he would do instead. He said he did not know.

He quit that same day.

Within three and a half years, his off-market real estate business had closed 400 deals. One every business day. No passive income strategy. No slow build. Just a decision, a lot of work, and a complete willingness to live on 25% of his former income until the business kicked.

That is the mindset this episode is built around.

KEY TAKEAWAYS

1. Passive income is not a strategy. It is an excuse. Most people using their "financial freedom number" as a benchmark have no real plan to hit it. They are using it to justify staying comfortable.
2. It is easier to make $1,000,000 than to replace a $200,000 W-2 with passive income. Mike has had this exact conversation with hundreds of students. The math almost never works the way people think it does.
3. Your W-2 is not safe. Tech layoffs, restructuring, industry shifts. You do not control it. Mike's income dropped 75% when he left engineering, but he chose the risk. The W-2 employee thinks they are avoiding risk. They are not.
4. Build the war chest first. Most investors save every dollar, dump it into the next property, drain all liquidity, and repeat. Mike's students learn to build a pipeline first, generate income through wholesaling, then deploy capital strategically into assets they actually want to keep.
5. Real estate is the vehicle. Not the destination. The skills you build, marketing systems, sales processes, deal analysis, transfer to any business. Mike could apply what he built to an HVAC company, a franchise, or anything else.
6. The $40,000 check moment changes everything. Almost every student who comes into Mike's program says they just want rentals and passive income. About three months in, after their first assignment check, they stop talking about passive income entirely.

If you are a contractor business owner and you want to make more money, work less, and win at home, we built something for you.

Go to gatheringthekings.com and apply for a GTK Growth Audit. We will show you exactly where you are leaking time, profit, and opportunity, and what it would take to fix it.

Connect with Chaz Wolfe (Host):

Website

Facebook

Instagram

LinkedIn

YouTube

Connect With Mike DeHaan (Guest):
YouTube: https://www.youtube.com/@collectingkeys
Instagram: @mike_invests
Website + Scale Program: https://collectingkeys.com/scale

Resources Mentioned:
The 4-Hour Work Week by Tim Ferriss: Buy It Here

Collecting Keys Animated Adventures: Watch It Here

GTK Full Resource Library: Get It Here

Support the show

Like what you heard?

Share this episode with a friend and leave us a review on Apple Podcasts or Spotify!

Join the conversation by visiting GatheringTheKings.com and apply to connect with other high-performing entrepreneurs and their families.

Connect With Chaz

80% of video on social media is watched without sound.

If you are not captioning your videos, you are invisible to 8 out of 10 people scrolling past your content right now. That is not a social media tip. That is a revenue problem.

Cam Beaudoin spent years as an IBM developer before realizing he was always the one who wanted to present at demo day. He turned that into two businesses: one helping professional speakers build real speaking businesses, and one helping companies make their content accessible to more people.

The message he brings contractors is simple. You already have the most important thing video content needs. You have a face, a job site, and a phone. Start pressing record.

KEY TAKEAWAYS

1. Video is the fastest trust builder you have. 91% of consumers want more video from brands. A 30-second video of you introducing the technician coming to their home does more for customer trust than any marketing piece you could pay for.
2. 80% of video is watched without sound. Facebook's own research showed it. Captions are not optional. They are the difference between someone watching your content and scrolling past it.
3. The record button is the hardest button to push. Once you hit it, it gets easier every time. You do not need a camera crew. You need your phone and a reason to talk.
4. Reusable content compounds over time. Videos that get 2 likes today become a course next year. A collection of short how-to videos becomes a paid subscription product. Start building the library now.
5. Accessibility is usability. If your content is hard to read, hard to hear, or hard to see, you are removing people from your audience. Fix your colors, caption your videos, and check your contrast.
6. Starting a business with kids is different, and that is okay. The mental load is higher. The time is tighter. The key is not balance. It is deciding what you are building and committing to the next small step, not the full mountain.

If you are a contractor business owner doing $1M+ and you feel stuck in the day-to-day, we built GTK for you.

Through peer mastermind and 1:1 coaching, we help you:

• Increase profit
• Install real systems
• Build a team that runs the business
• Get your time back

Go to gatheringthekings.com and apply for a GTK Growth Audit. We will show you exactly where you are leaking time, profit, and opportunity.

Connect with Chaz Wolfe (Host):

Website

Facebook

Instagram

LinkedIn

YouTube

Connect with Cam Beaudoin:

• Instagram: @thefrequentspeaker
• LinkedIn: linkedin.com/in/cambeaudoin
• YouTube: youtube.com/@AcceleratedAccessibility

Resources Mentioned:

• YouTube Live, Facebook Live, Instagram Live for practice
• Accelerated Accessibility: youtube.com/@AcceleratedAccessibility

Support the show

Like what you heard?

Share this episode with a friend and leave us a review on Apple Podcasts or Spotify!

Join the conversation by visiting GatheringTheKings.com and apply to connect with other high-performing entrepreneurs and their families.

Connect With Chaz

At 29, Sean Martin was making 6 figures in medical sales, had the gift of persuasion, and was doing 2 years in federal prison.

Not because he couldn't succeed. Because he was afraid he actually could.

Sean grew up in the Bronx, the son of a Dominican immigrant who raised him alone. He got the college degree. He got the sales job. He built the income. And still, the programming from the streets kept pulling him back. Until he had no choice but to sit with it for 2 years and rewrite everything.

He filled composition notebooks with the next 10 years of his life. He hit almost every target.

This episode is about what it actually takes to change the temperature you were set at.

KEY TAKEAWAYS

1. The subconscious thermostat is the real problem. Like a thermostat set to a fixed temperature, your mind will pull you back to whatever standard you were raised at, no matter how far you push. You have to consciously reset the temperature or you will always return to it.
2. Fear of success is more common than fear of failure. Sean scored off the charts for fear of success on personality assessments. Many ambitious people self-sabotage because they don't know who they will be when they actually achieve what they say they want.
3. Prison was the pause that made everything possible. Two years of sobriety, 200 books, and composition notebooks full of goals. Sean did not kill time in prison. He designed his future. Almost all of it came true.
4. 10x is easier than 2x. To double your income, you grind harder at what you already know. To 10x, you have to completely abandon what you know and find who has already done what you want to do. The goal itself forces you out of broken programming.
5. You cannot bring everyone with you. Your growth is a threat to people who are not growing. That includes people you love. The ones who truly support you will do it from a distance. The ones pulling you down are not evil. They are just a mirror of where you used to be.
6. What you stop doing matters more than what you start doing. Getting sober 18 months ago was not about adding a habit. It was about removing the thing Sean used to numb himself from his own potential. Stop the numbing first.
   
   

If you are a contractor business owner doing $1M+ and you feel stuck in the day-to-day, we built GTK for you.

Through peer mastermind and 1:1 coaching, we help you:

• Increase profit
• Install real systems
• Build a team that runs the business
• Get your time back

Go to gatheringthekings.com and apply for a GTK Growth Audit. We will show you exactly where you are leaking time, profit, and opportunity.

Connect with Chaz Wolfe (Host):

Website

Facebook

Instagram

LinkedIn

YouTube

Support the show

Like what you heard?

Share this episode with a friend and leave us a review on Apple Podcasts or Spotify!

Join the conversation by visiting GatheringTheKings.com and apply to connect with other high-performing entrepreneurs and their families.

Connect With Chaz

What does financial discipline look like when it grows from desperation instead of discipline?

Janine Jennings didn't learn about net worth from a finance professor. She learned it in an ICU, watching her infant daughter fight for her life, while still working hair clients to keep the lights on. When her daughter passed, she had nothing. She restarted with one appointment and a $40 tip.

Today, she runs a full tax and accounting firm, speaks the language of the self-employed, and has a formula she calls your "quintillionaire number." The number every contractor should know but almost none actually do.

This episode is about money, but it's really about what it takes to stop drifting.

KEY TAKEAWAYS

1. Track your money daily or you are drifting. Most people know what they earn. Few know what they spend. Janine says treat your finances like your phone: check it every day.
2. Your "quintillionaire number" is your retirement target. Take your income, subtract expenses, add side income, add 3% for inflation, multiply by 2.5. That is your freedom price. The formula is on her website.
3. Retirement is not optional just because you own a business. Self-employed people have no employer plan. Janine's entry-level tools: Acorns for a Roth IRA, Vanguard for the S&P 500. You can start with $10 a week.
4. Resilience is the decision to keep making money move. When Janine lost her daughter, she forced herself to take one more appointment. Then one more. That is not a metaphor. That is the actual mechanism of recovery.
5. Net worth is your number one financial metric. Income minus expenses equals net worth. If you are not tracking it, you cannot improve it.
6. Starting over does not require a head start. Janine rebuilt twice: after her daughter's passing and again after her divorce. Both times she started with one client, one service, one next step.

If you're a contractor business owner doing $1M+ and you feel stuck in the day-to-day, we built GTK for you.

Through peer mastermind and 1:1 coaching, we help you:

• Increase profit
• Install real systems
• Build a team that runs the business
• Get your time back

Go to gatheringthekings.com and apply for a GTK Growth Audit. We'll show you exactly where you're leaking time, profit, and opportunity.

Connect with Chaz Wolfe (Host):

Website

Facebook

Instagram

LinkedIn

YouTube

Connect with Janine Jennings (Guest):

• Website: jptaxservice.com
• Instagram: @jenningspeytontaxservice
• Facebook: @JPTaxServices
• LinkedIn: linkedin.com/in/janinejennings9999
• TikTok: @jptaxservice
• YouTube: JP Tax Service and Accounting

Support the show

Like what you heard?

Share this episode with a friend and leave us a review on Apple Podcasts or Spotify!

Join the conversation by visiting GatheringTheKings.com and apply to connect with other high-performing entrepreneurs and their families.