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Driven To Win

Gathering The Kings

Driven To Win is the podcast for entrepreneurs who want to build a profitable business without losing their family along the way. Hosts Chaz Wolfe and Jake Isaacs interview founders, CEOs, investors, and authors about the decisions, habits, failures, and relationships behind real results.

Across more than 500 conversations, the show covers how to:

  • Scale a business through leadership and systems
  • Sell and market with discipline
  • Build a team that runs without you
  • Create and protect wealth
  • Lead your family with the same intent you bring to your company

Chaz built and scaled companies in franchising, home services, real estate, and online education, and became a millionaire by 29. Jake is co-founder and integrator of Gathering The Kings, a peer mastermind for established business owners.

If you own a business doing $1M or more and want peers who hold you accountable in business and at home, learn more at gatheringthekings.com.

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  • 26 episodes
  • daily
  • Avg 46 min
  • English

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  • #451
    October 12 · 42 min

    His Company Lost $7 Million on One Job | Ryan Schmitt

    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 profit install real systems build a team that runs the business get 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.

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  • #452
    October 7 · 42 min

    From Miserable Engineer to 400 Real Estate Deals | Mike DeHaan

    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 profit install real systems build a team that runs the business get 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.

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  • #453
    October 5 · 47 min

    Why Your Business Needs to Be on Video Now | Cam Beaudoin

    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 profit install real systems build a team that runs the business get 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 Cam Beaudoin: Instagram: @thefrequentspeaker LinkedIn: linkedin.com/in/cambeaudoin YouTube: youtube.com/@AcceleratedAccessibility 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.

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  • #454
    September 30 · 48 min

    How 2 Years in Federal Prison Built an 8-Figure Career | Sean Martin

    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 profit install real systems build a team that runs the business get 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.

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  • #455
    September 28 · 36 min

    She Started Over With $40 and Built Wealth | Janine Jennings

    Connect With Chaz Janine Jennings lost her infant daughter after a heart transplant, had no money left, and restarted her business with one $40 client. If you own a business and you do not know your net worth or your retirement number, this episode is for you. Janine is the president of JP Tax Service and Accounting and Cultural Differences Salon. She started as a hairstylist, took a free HR Block course to earn extra money in the slow winter months, and grew one phone call into a full tax firm. Her daughter spent four months in the ICU in 2004 while Janine kept working to pay rent. That loss taught her why self-employed people need savings and a retirement plan. In this conversation with Chaz Wolfe, you will learn how to track your money daily, how to calculate your "quintillionaire number," and how to keep moving when everything falls apart. Key Takeaways Check your spending and net worth every day, the same way you check your phone. Most people were never trained to do it. A lot of people outlive their money. Pick a retirement date, then go to SSA.gov to see what you will draw. You need 40 credits to collect Social Security. You can start small. Put $10 a week into a Roth IRA through Acorns, or $50 a month into an S&P 500 fund at Vanguard. Your quintillionaire number: income minus expenses, plus side income, plus 3% for inflation, times 2.5. On $200,000 income and $36,000 in expenses, that comes to about $448,000. Earning $200,000 and spending $205,000 does not work. Grow income, hold spending flat, and put the gap to work. At rock bottom, give yourself permission to proceed and stop blaming yourself. Then take the next appointment. Consistency earns referrals. Customers come back when they know what to expect from you. Chapters 00:00 Meet Janine Jennings of JP Tax Service 03:01 Why You Must Track Spending Daily 05:24 Three Steps to Plan Your Retirement 07:43 Her Daughter's Heart Transplant Story 12:57 What to Do at Rock Bottom 16:44 Divorce and Building Unshakable Consistency 20:56 Starting Over With One $40 Client 23:59 From Hairstylist to Full Tax Firm 27:22 How to Find Your Quintillionaire Number 32:16 One App to Track Your Net Worth 34:01 How to Connect With Janine Jennings 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 profit install real systems build a team that runs the business get 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 Janine Jennings (Guest): Website: jptaxservice.com Instagram: @jenningspeytontaxservice Facebook: @JPTaxServices LinkedIn: linkedin.com/in/janinejennings9999 TikTok: @jptaxservice YouTube: JP Tax Service and Accounting 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.

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  • #456
    September 14 · 50 min

    Heal Your Past So You Don't Repeat It at Home | Rick Jordan

    Connect With Chaz Rick Jordan's deal to take his company public fell apart eight times in the last five days before it closed. If you run a service business and cash feels tight, his rule of thirds gives you a margin target you can check today. Rick is the founder and CEO of Reach Out Technology, a public cybersecurity company with 78 employees. He went from the first Geek Squad agent in Chicago to buying companies, and he lived through survival mode when he was laid off right as his twins were born. You will learn how to tell the difference between hard work and forcing it, why fear only goes away when you act, how proximity built his relationship with his kids, and how to run your numbers so you can pay yourself and still fund growth. Key Takeaways Difficulty means you need to figure out how. Ignoring every sign that says stop means you are forcing it. When two options both look bad, look for a third. Rick did that at every impasse until his public company deal closed. The only way to stop feeling fear is to act. You do not need step seven. You need step one. Proximity is Rick's number one parenting tip. He took his twins on errands from two months old, and at 16 they still ask to come along. Rule of thirds: cost of goods sold is one third of revenue, overhead is one third, and net income is one third after you pay yourself. Reinvest half of that net income into growth. No money problem is unsolvable with more revenue at good margins. When cash is tight, offer 5% off for payment wired in 48 hours. Rick's code is calm, confident, never hesitate. His advice to his younger self is simple: don't wait. Chapters 00:00 Meet Rick Jordan of Reach Out Technology 02:43 How to Know When to Push or Quit 05:27 The IPO Deal That Fell Apart Eight Times 08:11 Where Self-Limiting Beliefs Come From 09:56 The Only Cure for Fear Is Action 13:29 Fix the Broken Child in You 16:18 Proximity Is the Number One Parenting Tip 22:45 The Rule of Thirds for Service Businesses 29:27 Classify Your Numbers and Forecast 13 Weeks 32:06 Fix Cash Flow by Selling More 34:41 Why Pivoting Is Often a Pricing Problem 36:51 Do More With the Same People 40:28 Someday Never Comes, Only Today 45:51 Calm, Confident, Never Hesitate 48:23 How to Connect With Rick Jordan 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 profit install real systems build a team that runs the business get 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.

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Showing 21–26 of 26 episodes