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Driven To Win

Advertise on podcast: Driven To Win

Rating
★★★★★
5
from
82 reviews
This podcast has
77 episodes
Language
English
Publisher
Chaz Wolfe
Explicit
No
Date created
2022/01/24
Latest episode
2026/10/29
Average duration
48 min.
Release period
3 days

Description

Grow your business without sacrificing family or me time. Sign up for our Family Mastermind here: https://gatheringthekings.com/family-mastermind.Do you also feel driven to win? My name is Chaz Wolfe. I'm a serial entrepreneur, investor, and founder of Gathering the Kings.Throughout my career, I've built, purchased, and sold multiple 7-figure ventures in franchising, home service, real estate, and consulting. And I know first-hand how being a business owner can be a lonely and isolating experience.I created the 'Driven to Win' podcast to help entrepreneurs who are trapped in the cycle of trying to grow their businesses without having time or energy for anything else. Here, we share insights about self-mastery, emotional intelligence, and resilience so you can find financial freedom, build thriving relationships, and nurture spiritual wellness. Follow wherever you get your podcasts for tips on how to lead a balanced, exceptional life.

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The 3 Reasons You Are Broke and the Path to $300K a Year | Brad Lea
2026/10/29
Connect With Chaz Brad Lea dropped out of high school at 16 and grew up in a blue collar family that told him to get a real job. He stumbled into sales, started out earning everyone around him, and went on to build many businesses. He says if you are broke, there are only three reasons: your mindset, your skillset or your habits. Brad says if you make $90,000 a year, you can make $200,000, and the path starts with selling something you believe in. If your business already does $1M in revenue, he says you beat 92 percent of businesses, and tweaking a few levers can turn $200,000 of profit into $400,000. People pay him $6,000 for an hour of his opinion, and most of them already had the same answer. In this conversation with Chaz Wolfe, Brad explains how you use gratitude, sales and relationships to grow your income without sacrificing your family. KEY TAKEAWAYS Talk to more people. Brad says the more hands you shake, the more money you make. A salesperson earning $80,000 from 100 customers can talk to 200 and expect $160,000 or more.Find which of the three is broken. Brad traces every money problem to mindset, skillset or habits. A positive mindset with bad habits still fails, and a strong mindset with strong habits can win with average skill.Do more, get better, then scale. Increase your volume first, then study sales, closing and persuasion. When you are maxed out, scale by leveraging people and technology.Keep more of what you already make. At $1M in revenue you have proven the model. Brad says tweaking a few levers can double profit from $200,000 to $400,000 and help you grow faster.Protect the relationship before the dollar. Brad says every dollar you receive comes from a relationship. If you chase the money and damage the relationship, the money goes with it.Trust your own opinion. Brad would tell his younger self to read 10 to 20 pages of a self help book every day and stop worrying about what people think unless you pay them for it.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. Get the free Owner Time Audit at gatheringthekings.com/timeaudit. It is a simple worksheet that shows you where your week really goes. We email it to you as a PDF within minutes. Connect with Chaz Wolfe (Host): Website Facebook Instagram LinkedIn YouTube Connect With Brad Lea: Website: https://bradlea.com/ YouTube: https://www.youtube.com/vtbradlea Facebook: https://www.facebook.com/TheRealBradLea Instagram: https://www.instagram.com/therealbradlea/ LinkedIn: https://www.linkedin.com/in/bradlea/ TikTok: https://www.tiktok.com/@therealrealbradlea?lang=en 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.
60 Units, $10K a Month, and About 10 Hours a Week | Jason Velie
2026/10/28
Connect With Chaz Jason Velie started in real estate at about 30, while he still worked in finance. His first rental went badly. A bad inspection and a contractor who took $16,000 left the house sitting empty for about two years before it broke even. His first flip went much better and proved the model. He kept flipping and used the profits as down payments on apartment buildings. Today he holds about 60 units across four properties, clears more than $10,000 a month in net passive income, and works about 8 to 12 hours a week. He left his day job in April 2023. In this conversation with Chaz Wolfe, Jason talks about honest deals, an abundance mindset, and building wealth so you can be generous. KEY TAKEAWAYS Deal honestly, even when a lowball would pay more. A clear, fair offer builds the reputation that brings you the next deal.There is plenty of opportunity. Jason does not hoard what he knows or treat other investors as enemies.Give freely. He works every day to be able to be generous on every occasion.Get experienced help early. Vet your inspectors and contractors. Cheap help cost him dearly on his first rental.Use flips to fund the long game. Short term profits became down payments on assets that pay every month.Build the safety net first. Once passive income covers your living costs, you can make every other decision from strength. 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. Get the free Owner Time Audit at gatheringthekings.com/timeaudit. It is a simple worksheet that shows you where your week really goes. We email it to you as a PDF within minutes. Connect with Chaz Wolfe (Host): Website Facebook Instagram LinkedIn YouTube Connect With Jason Velie:  Instagram: https://www.instagram.com/jasonvelie 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.
She Sold Her Business to Bill Gates. Build Yours to Sell | Beate Chelette
2026/10/27
Connect With Chaz Beate Chelette built a business and sold it to Bill Gates. Today she calls herself The Growth Architect. She helps owners turn their talent into a business, add the systems that make it run, and build it so someone would want to buy it. She sees a lot of owners do the opposite. They buy course after course and tool after tool, chasing the next marketing promise, without ever building the business model underneath. In this conversation with Chaz Wolfe, Beate explains how to stop chasing tactics and start building a company with real value. KEY TAKEAWAYS Decide the end game early. A business built to sell for $50 million is set up differently from one built for $1 million.Write clear job descriptions. Roles that mix unrelated duties, like HR and sales, create overloaded mini me jobs that nobody can do well.Know what your skills are worth. Compare what your talent could earn with what you earn today, then decide what you want.Build the model before you buy the tools. Courses, funnels, and software do not fix a missing business model.Use a proven blueprint and a peer group. Learning from people who have done it is faster than figuring it out alone.What got you here will not get you there. Question the stories you tell yourself about what is possible. 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. Get the free Owner Time Audit at gatheringthekings.com/timeaudit. It is a simple worksheet that shows you where your week really goes. We email it to you as a PDF within minutes. Connect with Chaz Wolfe (Host): Website Facebook Instagram LinkedIn YouTube Connect With Beate Chelette:  Website: https://beatechelette.com/  LinkedIn: https://www.linkedin.com/in/beatechelette/  Instagram: https://www.instagram.com/beatechelette/ 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.
If You Can't Justify a Premium Price, You're Doing It Wrong | Colin Sanburg
2026/10/26
Connect With Chaz Colin Sanburg went to work in a family owned manufacturing company at 21. He ended up running it as CEO for almost 15 years and led a turnaround that took about 10 of them. He later started an industrial distribution company and still owns both. Along the way he noticed something. Most owners take their financial advice from their banker or their CPA. Neither one is focused on making the business more profitable. So Colin built FinElevate to sit in the finance seat with owners and run a profit playbook every week. In this conversation with Chaz Wolfe, Colin explains how an owner can understand the numbers well enough to lead with them. KEY TAKEAWAYS Pick one unit everyone understands. Jobs completed, cleanings done, seats filled. When sales, operations, and finance use the same unit, everyone speaks the same language.Start with two or three numbers. Add more only after your team understands the first ones.Charge a premium and earn it. Low prices still require full service. Colin says if you cannot justify premium pricing, you are doing it wrong.Read your P&L as percentages. Track each cost as a share of revenue, like labor at 30 percent or less.Know your fixed and variable costs. If revenue doubles and fixed costs stay flat, profit jumps. Run the what ifs.Delegate the work, not the understanding. You do not have to be the accountant. You do have to know the story well enough to hold your advisors accountable. 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. Get the free Owner Time Audit at gatheringthekings.com/timeaudit. It is a simple worksheet that shows you where your week really goes. We email it to you as a PDF within minutes. Connect with Chaz Wolfe (Host): Website Facebook Instagram LinkedIn YouTube Connect With Colin Sanburg:  Website: https://finelevate.com/  LinkedIn: https://www.linkedin.com/in/colinsanburg/  Instagram: https://www.instagram.com/the.finelevate/ 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.
Three People Running a Hundred AI Agents | Alexander De Ridder
2026/10/25
Connect With Chaz Alexander De Ridder builds AI agents for a living. His company, SmythOS, lets teams create agents with drag and drop tools and no code. His picture of the future is a small team of three people running a hundred agents that do the repetitive work. That sounds far away for a lot of owners. Alexander says it is closer than most think, and the companies that stay lean and learn early will have a big cost advantage over the ones that wait. In this conversation with Chaz Wolfe, he explains what AI agents are, where to start, and how to keep people in control. KEY TAKEAWAYS Start now with the basics. Use the free versions of common AI tools on your own work before you spend money on anything bigger.Do not mow your lawn with a bazooka. Keep AI on a short leash. Approve each step and keep a person responsible for every decision.Train a few people. Pick one to four people on your team to learn how to build and run agents.Lean companies win. A competitor with much lower costs can make a slow company irrelevant.Get ready for AI customers. More people will use AI assistants to find and buy services. Make sure your business can be found and understood.Humans multiplied. Alexander says it is not human versus machine. It is people doing more with machines. 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. Get the free Owner Time Audit at gatheringthekings.com/timeaudit. It is a simple worksheet that shows you where your week really goes. We email it to you as a PDF within minutes. Connect with Chaz Wolfe (Host): Website Facebook Instagram LinkedIn YouTube Connect With Alexander De Ridder:  LinkedIn: https://www.linkedin.com/in/adridder/ 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.
She Left Nike Weeks Before the Pandemic. Here's How She Survived | Dr. Taryn Marie Stejskal
2026/10/24
Connect With Chaz Dr. Taryn Marie Stejskal led executive leadership development at Nike and global leadership development at Cigna. In February 2020 she left Nike to start her own company. She had bookings lined up to replace her income. She was a single mom with two young sons. Within weeks the pandemic wiped those bookings out. She ran her business on a 30 day cash runway for 36 months, with no outside money. Today she leads the Resilience Leadership Institute and wrote the bestselling book The Five Practices of Highly Resilient People. In this conversation with Chaz Wolfe, Taryn breaks down what resilience really is and how an owner can build more of it. KEY TAKEAWAYS Resilience means coming out better. Taryn defines it as facing challenge, change, and complexity and coming out enhanced, not diminished.Do not try to go back. She says we do not return to who we were before a hard season. We bounce forward.Know when to push and when to pivot. Productive perseverance means you stay the course or change it on purpose.Leading can be lonely. Even owners surrounded by people carry decision fatigue. Connection with yourself and with others is part of the fix.Audit your self talk. Listen to your own words for 24 hours. Replace have to with get to.Fear is information. Notice it, but do not let it make your decisions. 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. Get the free Owner Time Audit at gatheringthekings.com/timeaudit. It is a simple worksheet that shows you where your week really goes. We email it to you as a PDF within minutes. Connect with Chaz Wolfe (Host): Website Facebook Instagram LinkedIn YouTube Connect With Dr. Taryn Marie Stejskal:  Website: https://www.resilience-leadership.com/  Instagram: https://www.instagram.com/drtarynmarie/  LinkedIn: https://www.linkedin.com/in/taryn-marie-stejskal/ 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.
The One Habit Keeping Successful Men Stuck at 70% | Clifford Stephan
2026/10/23
Connect With Chaz Clifford Stephan spent 20 years building a compensation consulting firm in Silicon Valley. He was successful, social, and a regular drinker since high school. In his late thirties he started to feel like he was aging faster than he should. He spent real money on sleep, supplements, and diets. None of it fixed the problem. Then he took a full year off alcohol. That one decision changed his sleep, his energy, and his health. At 50 he was surfing 10 foot waves in Nicaragua. He turned the experience into Booze Vacation, a coaching program that helps high achieving men take a long break from drinking and see what they are really capable of. In this conversation with Chaz Wolfe, Clifford explains why he believes a lot of successful men are running at 60 to 70 percent, and why alcohol is often the reason. KEY TAKEAWAYS Moderate drinking still has a cost. Clifford says even a few drinks a week can hurt sleep, hormones, mood, focus, and recovery.One decision beats a hundred small ones. A long break replaces the daily question of whether to drink tonight. Clifford calls it trading one decision for a hundred.Play offense, not defense. A short dry month is defense. A three, six, or 12 month break gives your body and brain time to show you the difference.The first few weeks are the hardest. After that the focus moves to sleep, exercise, personal growth, and rebuilding a social life that does not depend on alcohol.Muscle is your currency for longevity. In your 40s and 50s, strength training matters more than most supplements.Ask if it serves you. Chaz has never had a drink. His test is simple. If my success is up to me, why would I take in something that takes away my control? 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. Get the free Owner Time Audit at gatheringthekings.com/timeaudit. It is a simple worksheet that shows you where your week really goes. We email it to you as a PDF within minutes. Connect with Chaz Wolfe (Host): Website Facebook Instagram LinkedIn YouTube Connect With Clifford Stephan:  Website: https://boozevacation.com/  Instagram: https://www.instagram.com/boozevacation/  Facebook: https://www.facebook.com/BoozeVacation/ 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.
From $2,000 Land Deals to Four Businesses and Home for Dinner | Travis King
2026/10/22
Connect With Chaz Travis King started a real estate side hustle with his wife while he still had a salaried job. The 2008 recession hit his house deals hard, so he switched to land. The deals were smaller and the risk was lower. Some early flips made only about $2,000 each. He kept going. His goal was $10,000 a month in recurring revenue. The side business passed his salary and he walked away from the job. Today he runs four connected businesses, each with a small remote team, and he built them so he could be home with his sons. In this conversation with Chaz Wolfe, Travis shares how focus and repetition turned a side hustle into a business that fits his family. KEY TAKEAWAYS Pick one thing and stay with it. Travis says almost anything will work if you commit to it for 12 to 18 months instead of switching after a few.Mastery comes through frequency. Lots of small, low risk deals built his skill and his confidence. After 20 to 40 deals, he knew what he was doing.Set a number you can measure. His target of $10,000 a month gave the side hustle a finish line.Courage is not the absence of fear. The successful people Travis knows still feel fear. They move anyway.Learn from someone who has done it. A mentor gets you there faster than any shortcut.Win at home first. If your kids do not think you were a great dad, Travis asks, who cares what else you built? 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. Get the free Owner Time Audit at gatheringthekings.com/timeaudit. It is a simple worksheet that shows you where your week really goes. We email it to you as a PDF within minutes. Connect with Chaz Wolfe (Host): Website Facebook Instagram LinkedIn YouTube Connect With Travis King:  Website: https://travisking.com/  Facebook: https://www.facebook.com/landeducator/  Instagram: https://www.instagram.com/_travisaking/ 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.
Disney, Harley Davidson and NASA Hired Him to Automate Their Work | Phillip Brown
2026/10/21
Connect With Chaz Phillip Brown has spent about 20 years automating how businesses run. His firm, Blu Pitt, has built systems for Walt Disney, Harley Davidson, and NASA. He also works with small companies that have 5 to 15 people. His view is simple. The average business uses 50 to 100 different software tools every week. About 80 percent of the back office work can be automated. Most owners just have not written down what they do. In this conversation with Chaz Wolfe, Phillip explains how an owner can get hours back every week without being a programmer. KEY TAKEAWAYS Write it down first. If a task only lives in your head, nobody else can do it and no tool can automate it. Turn your daily and weekly work into simple playbooks.Start with the work you dread. Email sorting, payment checks, and bookkeeping repeat every week. Those hours add up fast.Connect what you already have. You may not need a new all in one platform. Getting your current tools to talk to each other often matters more.Ship it, then fix it. Early in his career Phillip saw most software projects die before launch. Release something small, get feedback, and improve it.Check before you build. Someone may already sell a tool that solves your problem better and cheaper.Give AI clear instructions. Phillip says to think of a computer as a child with a fresh mind. Tell it exactly what you want in plain language. 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. Get the free Owner Time Audit at gatheringthekings.com/timeaudit. It is a simple worksheet that shows you where your week really goes. We email it to you as a PDF within minutes. Connect with Chaz Wolfe (Host): Website Facebook Instagram LinkedIn YouTube Connect With Phillip Brown:  Website: https://www.blupitt.com/home  LinkedIn: https://www.linkedin.com/in/phillipjbrown/ 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.
He Didn't Start Playing Until 14. Then He Went Pro for 10 Years | Dre Baldwin
2026/10/19
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 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.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.Review your habits like employees. Every habit gets a review. Keep it, adjust it, or let it go.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.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.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. Get the free Owner Time Audit at gatheringthekings.com/timeaudit. It is a simple worksheet that shows you where your week really goes. We email it to you as a PDF within minutes. Connect with Chaz Wolfe (Host): Website Facebook Instagram LinkedIn YouTube Connect With Dre Baldwin:  Website: https://dreallday.com 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.
I Treated My Team Wrong for 10 Years as CEO | James Lawrence
2026/10/14
Connect With Chaz James Lawrence met with more than 500 CEOs and found the biggest companies had the worst people problems. If you lead a team and still make every call yourself, this episode shows you what that costs. James Lawrence was a CEO for 20+ years, mostly in automotive, and admits he made every mistake in the book in his first 10 years as a leader. Today he runs Happy, a platform that uses behavioral science and AI to coach each employee on how to work with the specific people around them, right before the meeting happens. You will hear how Vince Lombardi and Andy Reid led individuals instead of a roster, the 60-second walk that changed how James handles anger, and the backyard exercise that pointed him to the work he does now. Key Takeaways When a leader makes every decision because he does not trust his team, he wastes the people he is paying.Not everyone sees the world like you. A quiet, analytical person in a meeting is listening, not rejecting you.Vince Lombardi said he had 50 men on his team and treated them as 50 unique people. Know when to push in public and when to talk in private.When emotion spikes, take a 60-second walk around the building. James did it so often his team wondered where he went, and it changed how he responds.Engaged teams are more profitable, more productive and keep people longer. Treating culture as an extra is a mistake.Take a blank pad, set money aside, and write what you want from the rest of your life. James spent three to four hours at a time on it, over about three months.James writes the number of days he likely has left at the top of his to-do list every day. Nothing has made him value his time more. Chapters 00:00 Meet James Lawrence, CEO of Happy 02:38 Why Leaders End Up Making Every Call 06:25 What 500 CEOs Revealed About People 09:56 How the Happy Assessment Works 17:07 AI Coaching Before Your Next Meeting 20:28 Adapting to Others Without Faking It 25:50 Vince Lombardi Treated 50 Men Differently 29:52 Travis Kelce, Andy Reid and Psychological Safety 33:57 Every Mistake in His First 10 Years 37:30 Teaching Self-Awareness to Your Kids 39:45 Engaged People Are Not a Vitamin 44:54 The Blank Pad of Paper Exercise 49:56 Counting the Days He Has Left 54:03 Do the Work You Love Every Day 56:51 How to Connect With James Lawrence Make More Money. Work Less. Win At Home. 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 profitinstall real systemsbuild a team that runs the businessget your time back Get the free Owner Time Audit at gatheringthekings.com/timeaudit. It is a simple worksheet that shows you where your week really goes. We email it to you as a PDF within minutes. Connect with Chaz Wolfe (Host): Website Facebook Instagram LinkedIn YouTube Profit Starts with Better Books!Clean books. Clear reports. Monthly bookkeeping built by business owners, for business owners.Disclaimer: This post contains affiliate links. If you make a purchase, I may receive a commission at no extra cost to you.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.
His Company Lost $7 Million on One Job | Ryan Schmitt
2026/10/12
Connect With Chaz Ryan Schmitt's company lost about $7 million on one job, and he now calls it his most impactful project. If you run a contractor business and one bad job could sink you, this episode shows you how an owner walked back from the edge. In 2018, Ryan's heavy civil firm in Jacksonville lost its bonding. He recapitalized the company, sold every asset with equity, and borrowed $2 million from a peer in his business group. He had chest pains and kept his key man life insurance because he was not sure he would make it. He never had a single employee leave. Today, 230 people work for Petticoat-Schmitt. They hear the financials every Monday at 3:30, share in the profits, and are on track to own the company through an ESOP. You will learn how Ryan rebuilt around his people and why he gave up his office. Key Takeaways 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."Relationship capital is real capital. A peer lent Ryan $2 million and a surety contact showed up at his office the next morning because they knew his character.Transparency did not cause a stampede. Ryan shared the full financial picture during the worst of it. Every other company was hiring, and his people stayed.Get out of your office. Ryan now has no office. He meets crews on job sites with biscuits and asks, "What would you do if you were me?"Profit sharing turns workers into partners. Project and company level profit sharing gave his team a reason to fight through the rebuild, and the ESOP formalizes it.Run the business on a plan everyone sees. Ryan uses EOS, a daily 7 to 8 minute company huddle, and walks every new hire through the plan himself. Chapters 00:00 Inside a 230 Person Heavy Civil Firm 03:17 From Petticoat Contracting to 230 Employees 06:12 Why He Chose a Win Win Deal 09:43 The Valley of Darkness and $7M Loss 21:56 Chest Pains and a $2 Million Loan 28:57 Why He Gave Up His Office 32:57 Digger Day for Kids With Cancer 37:49 Patience and How to Connect With Ryan Make More Money. Work Less. Win At Home. 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 profitinstall real systemsbuild a team that runs the businessget your time back Get the free Owner Time Audit at gatheringthekings.com/timeaudit. It is a simple worksheet that shows you where your week really goes. We email it to you as a PDF within minutes. 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 Connect with Chaz Wolfe (Host): Website Facebook Instagram LinkedIn YouTube Profit Starts with Better Books!Clean books. Clear reports. Monthly bookkeeping built by business owners, for business owners.Disclaimer: This post contains affiliate links. If you make a purchase, I may receive a commission at no extra cost to you.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.
From Miserable Engineer to 400 Real Estate Deals | Mike DeHaan
2026/10/07
Connect With Chaz Mike DeHaan quit engineering the same day he decided to, with no plan, and closed about 400 off-market real estate deals in three and a half years. If you are using a passive income number as the reason you have not made your move, this episode is for you. Mike spent five years as an engineer and was miserable for four and a half of them. He called his wife on the drive to work, quit that day, and went from low six figures to driving Uber and working in a gym. His household income dropped about 75%. Today his business averages close to one deal every business day. Chaz Wolfe and Mike break down why passive income goals often become an excuse, why you should build a cash war chest before you buy rentals, and why the marketing and sales systems behind his business would work for an HVAC company too. Key Takeaways Passive income goals often become an excuse. A $200,000 earner needs a lot of properties to replace that income, and most never take the leap.Mike believes it is easier to make $1 million than to replace a high paying W-2 with passive income.Your W-2 is not safe. Tech workers earning $250,000 a year lost their jobs overnight in the past 12 months.Build runway before you jump. Mike had $100,000 saved and cut spending to about $4,000 a month so the family could live on his wife's income.Build the war chest first. Use debt, partners and other people's money for the deals worth keeping instead of draining your cash on every property.Students who say they only want rentals change their minds after their first $40,000 wholesale check, usually about three months in.Marketing, sales and deal analysis skills transfer to any business, from an HVAC company to a franchise. Chapters 00:00 400 Deals and Crazy Seller Stories 02:05 Real Estate Is a Marketing and Sales Business 05:14 Quitting Engineering the Same Day With No Plan 10:04 Act First and Plan Later 13:24 Why Passive Income Goals Become an Excuse 19:00 Living on $40,000 After a 75% Pay Cut 23:07 Do Not Be Afraid of the Work 25:48 It Is Easier to Make $1 Million 29:13 Build the War Chest Before Buying Rentals 32:06 Why Collecting Keys Shows the Losses Too 35:16 Turning Wild Deal Stories Into Cartoons 37:31 Squatters, Fist Fights and Jailhouse Sellers 39:59 How to Connect With Mike DeHaan Make More Money. Work Less. Win At Home. 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 profitinstall real systemsbuild a team that runs the businessget your time back Get the free Owner Time Audit at gatheringthekings.com/timeaudit. It is a simple worksheet that shows you where your week really goes. We email it to you as a PDF within minutes. Connect With Mike DeHaan (Guest): YouTube: https://www.youtube.com/@collectingkeys Instagram: @mike_invests Website + Scale Program: https://collectingkeys.com/scale Connect with Chaz Wolfe (Host): Website Facebook Instagram LinkedIn YouTube Profit Starts with Better Books!Clean books. Clear reports. Monthly bookkeeping built by business owners, for business owners.Disclaimer: This post contains affiliate links. If you make a purchase, I may receive a commission at no extra cost to you.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.
Why Your Business Needs to Be on Video Now | Cam Beaudoin
2026/10/05
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. Cam Beaudoin spent years as an IBM developer and was always the one who wanted to present at demo day. He turned that into two businesses: a creative agency that helps professional speakers build real speaking businesses, and work that helps companies make their content accessible to more people. In this conversation with Chaz Wolfe, you will learn how to get comfortable on camera, how to use short videos in your sales process to build trust, how to turn a library of how-to clips into a paid course, and how Cam sets a 40-hour work week while raising a 9-year-old and a 9-month-old. Key Takeaways 91% of consumers want more video from brands. Video consumption is up 254% in the past five years.Caption every video. Facebook research found 8 out of 10 people scroll with the sound off.The record button is the hardest button to push. Start with YouTube Live, Facebook Live, or Instagram Live. Nobody is watching your first one, so use it to practice.Use video in sales. A one-minute script of 60 to 80 words sent as a personal video gets you thanked. A cold call never does.Chaz sends a founder video when a lead books, then a video of the tech before the home visit. Clients know who is coming to their door.Your how-to clips compound. A set of bathroom remodel videos with 2 likes today can become a mini course you sell later.Decide what you want and set the limit. Cam caps his business at 40 hours a week and agreed on the 9 to 5 split with his wife.Chapters 00:00 Why 91% of Consumers Want Video 01:50 Building a Business for Professional Speakers 03:34 From IBM Developer to Speaker 06:53 Accessibility Is Usability 08:53 80% of Video Is Watched Muted 10:38 How to Get Comfortable on Camera 13:37 Why Video Builds Trust in Sales 16:05 Video Trust for Contractor Businesses 21:47 What a Speaker Demo Reel Does 25:42 Turn Short Videos Into a Course 28:26 Reframing the Fear of Starting 31:17 Starting a Business With Young Kids 38:34 Treat Speaking Like a Business 41:25 Sell From Stage at Home Shows 45:34 How to Connect With Cam Beaudoin Make More Money. Work Less. Win At Home. 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 profitinstall real systemsbuild a team that runs the businessget your time backGet the free Owner Time Audit at gatheringthekings.com/timeaudit. It is a simple worksheet that shows you where your week really goes. We email it to you as a PDF within minutes. Connect with Cam Beaudoin: Instagram: @thefrequentspeakerLinkedIn: linkedin.com/in/cambeaudoinYouTube: youtube.com/@AcceleratedAccessibilityConnect with Chaz Wolfe (Host): Website Facebook Instagram LinkedIn YouTube Profit Starts with Better Books!Clean books. Clear reports. Monthly bookkeeping built by business owners, for business owners.Disclaimer: This post contains affiliate links. If you make a purchase, I may receive a commission at no extra cost to you.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.
How 2 Years in Federal Prison Built an 8-Figure Career | Sean Martin
2026/09/30
Connect With Chaz Sean Martin wrote the next 10 years of his life in composition notebooks from a prison cell and hit almost every target. If you keep pulling yourself back to the same level no matter how hard you push, this episode is for you. At 29, Sean was making 6 figures in medical sales and still hustling on the side. He served 2 years in prison. He stayed sober, read over 200 books, and rewrote his identity. Today he runs a seven, almost eight figure a year medical supply business built on relationships with physicians, and he invests in commercial real estate. You will learn why your mind keeps resetting you to the standard you were raised at, why 10x can be easier than 2x, and why your success will cost you some relationships. Key Takeaways Your mind works like a thermostat. It pulls you back to the temperature you were raised at until you consciously reset it.Fear of success is real. Sean scored off the chart for it and sabotaged himself for years before he saw it.Use downtime as school. In prison Sean read over 200 books and wrote goals in notebooks. He hit almost all of them.10x is easier than 2x. A 10x goal forces you to stop relying on what you know and go stand next to someone who has done it.Add value before you ask. Doctors had no time to market, so Sean marketed their practices for them and won their business.What you stop doing matters most. Getting sober 18 months ago changed the entire structure of Sean's life.Your success is a threat to every relationship you started with. The people who love you will support you from a distance.Chapters 00:00 Two Years in Prison at Age 29 01:47 Building a Medical Supply Business on Relationships 06:58 Growing Up in the Bronx 12:29 Writing His Next 10 Years in Prison 16:17 Fear of Success and Your Inner Thermostat 23:16 Getting Sober and Letting Go 26:52 Why Your Success Threatens Old Relationships 29:47 Stop Needing Old Friends to Root for You 37:52 A Message for Single Moms 39:26 Real Success Mentors for Inner City Youth 45:12 Don't Stop Believing and Clean Your Feed 47:22 Wrap Up Make More Money. Work Less. Win At Home. 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 profitinstall real systemsbuild a team that runs the businessget your time backGet the free Owner Time Audit at gatheringthekings.com/timeaudit. It is a simple worksheet that shows you where your week really goes. We email it to you as a PDF within minutes. Connect with Chaz Wolfe (Host): Website Facebook Instagram LinkedIn YouTube Profit Starts with Better Books!Clean books. Clear reports. Monthly bookkeeping built by business owners, for business owners.Disclaimer: This post contains affiliate links. If you make a purchase, I may receive a commission at no extra cost to you.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.

Podcast reviews

Read Driven To Win podcast reviews


5 out of 5
82 reviews
★★★★★
Ozeal 2026/06/04
Driven to succeed as an entrepreneur!
This is a great all-around podcast. Everything from mindset to real, in the trenches type pf advice/guidance. Love Chaz’s energy and the conversations...
★★★★★
Chance McClain 2025/03/12
Sharp, Fun, and Worth Your Time
Chaz Wolfe knows how to pull out a convo. He asked questions that made me think, pushed me to reflect on my business, and somehow made it feel effortl...
★★★★★
Mck1ly 2024/11/27
Great listens
Well prepared and fascinating. Full of great info and interviews
★★★★★
Armando Le 2024/06/03
This podcast is legit!
Chaz is an amazing host! I really enjoyed our time!
★★★★★
liferx 2024/04/15
Top Notch
This podcast is filled with powerful and useful content! Very professional and well put together!
★★★★★
J9stein 2024/03/20
JP Tax Service and Accounting
Chaz is a prolific artist, host and person. His energy gives off a greatness that is unspoken and gives tons of value to everyone. Thanks for everythi...
★★★★★
B Walka 2024/02/21
Excellent podcast!
Good information, keeps your attention, and has a good variety of topic.
★★★★★
ThisIsRambo 2024/01/30
Chaz is a genius!
Chaz is a true business guru and I love this show. Amazing guests, and incredible content.
★★★★★
Jason Velie 2024/01/18
Top Class!
The podcast itself provides such a tremendous amount of value, but I was even more impressed with Chaz when I had the honor to be a guest. Regardless ...
★★★★★
muttin 2024/01/04
So much information
Such a great podcast with so much information hard to not listen.
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