Driven To Win

Gathering The Kings
  • 5.0 (82)
  • Entrepreneurship
  • Weekly

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 systemsSell and market with disciplineBuild a team that runs without youCreate and protect wealthLead your family with the same intent you bring to your companyChaz 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.

  1. 13h ago

    He Raised $325M, Then Five Key People Quit in One Day | Tim Calise

    Connect With Chaz Tim Calise grew his gym franchise business to eight locations, funded with a line of credit on his house. At 1:37 one Wednesday morning he lay awake thinking, if only everyone knew how screwed we are. The next day five of his main people quit. Years earlier, Tim and a partner started a hedge fund with $750,000 committed and raised over $325 million in three and a half years. He later served as the number two at Gym Launch with Alex and Leila Hormozi, where a stake sold to a private equity firm for a high eight figure number. Today he works with founders doing $500,000 to $3 million a year. In this conversation with Chaz Wolfe, Tim explains why product matters more than marketing at that stage, how to take a calculated risk, and why you should never work through a crisis alone. KEY TAKEAWAYS Count the offers you make. Tim says it is the only metric that matters before you find product market fit. Successful businesses do not know more than you. They iterate faster.Sell a micro product first. Pick the one thing you do that gets the biggest result with the least risk, name it, and sell it. A $49 workshop turns a stranger into a customer who can later become a client.Sell it before you build it. Describe the offer to your audience and use their feedback. Do it free for the first five people if you have to, because the value is the feedback.Take risks with a downside you can live with. Tim is moving high ticket leads to a program at a 95% discount because he expects a business 3 to 10 times larger. Think in probabilities, not possibilities.Do not isolate when things go wrong. Get everything out of your head and onto paper, then call someone who can be objective. Then tell your spouse where you are and how you plan to fix it.Write an intention document and publish it. Tim's lays out where he came from, where he is going, and what he will not accept, like calls at 11 at night. Every client and prospect has to read 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 Tim Calise: Website: https://timcalise.com/ Instagram: https://www.instagram.com/tim.calise/ 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.

  2. 1d ago

    150 SOPs and One Hire Bought Back His Time | Tyler Woodall

    Connect With Chaz Tyler Woodall built an insurance agency by dialing 150 businesses a day and walking into 30 more. Then he had to put down his dog of almost 15 years, and it made him reassess his whole life. He got rid of the business he did not love, ended a relationship that was not working, and six months later his life looked completely different. To get himself out of the day-to-day, Tyler wrote out every task, recorded a Loom video for each one, and built 150 standard operating procedures. He hired one person, sent all 150 documents, and started handing off work. His company, Agency Aid, now helps insurance agencies, about 70 percent of its clients, automate the back end and delegate to virtual assistants. In this conversation with Chaz Wolfe, Tyler shows you how to document your work, delegate to a team you may never meet in person, and care for people so they stay. KEY TAKEAWAYS Write down every task before you hire. Tyler typed out each step, recorded a video, and built 150 SOPs before his first hire. Start with your biggest headaches and aim for 10 percent better, because done is better than perfect.Make people sign their checklists. A signature at the bottom makes your team read every line. If a signed checklist still misses the result, Tyler fixes the process instead of disciplining the employee.Nail the first six weeks. Tyler tells his customer success manager that a great first six weeks keeps a client for good. He holds his HR manager to the same standard for new team members.Kill failed ideas fast. Tyler's team tries something new every week and nine out of ten fail. A giveaway lead campaign flopped because agents did not want to cold call, so the team cut it after a few weeks.Manage deliverables, not hours. Tyler does not use time trackers with his core team. If the tasks get done, people can leave a couple of hours early and go be with their families.Care about the person outside of work. Tyler's HR manager runs a life goals program on love, influence, finance and energy. He says a man who feels in control of his life becomes incredibly loyal to you.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 Tyler Woodall: Website: https://agency-aid.com/ Website: https://winwithc4.com/ LinkedIn: https://www.linkedin.com/in/tyler-l-woodall/ Facebook: https://www.facebook.com/tyler.l.woodall YouTube: https://www.youtube.com/channel/UCcBS86j8j_84wQtr7YRVKJQ 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.

  3. 2d ago

    He Built a $50M Company, Then Got Fired | John St. Pierre

    Connect With Chaz John St. Pierre spent 15 years growing a sports business from about $10 million to more than $50 million in revenue. To chase $100 million he kept raising debt and investor money until his equity was diluted and he lost control. In 2018 the board fired him from the company he co-founded. That failure led to the seven principles in his book, The $100 Million Journey. He applied them to another business and grew it to $100 million the right way. Today he is CEO and chairperson of Rhombus Group, a holding company with six businesses run by their own CEOs. In this conversation with Chaz Wolfe, John shows you how to tie your business plan to a 30 year life plan and grow without giving away control. KEY TAKEAWAYS Write a life plan before a business plan. John maps 30 years across areas like finances, health, family and spirituality. Then he works back to 10 years, 3 years, 1 year, each quarter and each week.Decide if you are an operator or an owner. If you only want a job, your boss is you. John now coaches his CEOs as chairperson and stays out of daily operations.Know your self financeable growth rate. If your cash flow funds 5% growth and you push for 20%, the other 15% comes from banks and investors. That debt and dilution put your equity at risk.Protect the house. John has lost a quarter million dollars to a customer bankruptcy and another quarter million to a wire sent overseas by mistake. Run a vulnerability assessment every year.Build a team of advisors. John has six advisors on his team. He makes no irreversible decision unless all six agree.Move big rocks, not gravel. John reads a daily visualization for 12 minutes. He cuts anything from his weekly plan that does not tie to his 30 year plan.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 John St. Pierre: Website: https://100mjourney.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.

  4. 3d ago

    Every Hire Should Triple Customer Experience | Holly Jean Jackson

    Connect With Chaz Holly Jean Jackson built new projects inside companies like Visa, Treasury Wine Estates and the University of California. She kept getting laid off, and each layoff came with a big health challenge. She saw the pattern and left corporate America to build her own business. Today she is a revenue and performance consultant for business leaders, authors and speakers. When mature clients tell her margins dropped 30 to 50% in a quarter, she often finds five profit leaks on the first call. She also wrote the book and hosts the podcast Inspiration Contagion. In this conversation with Chaz Wolfe, Holly explains how to find your superpower, when to make your first hire, and how to protect your team from a bad apple. KEY TAKEAWAYS Ask the people closest to you what your superpower is. Buy a friend a coffee and ask what they highlight when they introduce you. Holly says the answers come quickly.Block your day around your energy. Group similar tasks so your brain is not switching all day. Expect it to take a year or two to find the schedule that fits you.Learn a task before you outsource it. Know the process, the expectation, and the impact on customers and employees. Then hand it to someone you trust.Hire when work is piling up and not firing you up. Most first hires are an assistant for scheduling, invoicing and admin. Then run the revenue ideas you never had time for.Make every hire raise your customer experience. Holly says each hire should make it at least three times better. If it does not, ask why you are hiring.Test new hires before full time. Holly uses a 30 day contract, then a 90 day contract with specific KPIs. Remove a bad apple fast because you cannot change a person's values.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 Holly Jean Jackson: Website: https://hollyjeanjackson.com/ LinkedIn: https://www.linkedin.com/in/hollyjjackson/ Instagram: https://www.instagram.com/coachhollyjeanjackson/ Facebook: https://www.facebook.com/hollyjeanjackson/ YouTube: https://www.youtube.com/channel/UC3ElvJLGqpJ2ThA9utJCqMg Linktree: https://linktr.ee/coachhollyjackson 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.

  5. 4d ago

    The 2.5 Year Pivot Behind the Uber of Heavy Equipment | Alex Kraft

    Connect With Chaz Alex Kraft spent 16 to 17 years at a heavy equipment dealership, starting in sales and rising to chief operating officer before the company was sold. His first version of Heave helped contractors buy and rent equipment online, but dealers refused to use it, and he ground for two and a half years. Then he found the real pain: getting broken machines fixed. Heave is now a labor marketplace that connects equipment owners with independent mechanics, which Alex calls Uber for heavy equipment repairs. Customers pay a fraction of the dealership price, and the mechanic keeps more of the value he creates. After Heave raised Silicon Valley venture capital in August, Alex hired salespeople from the industry for passion over experience. In this conversation with Chaz Wolfe, Alex explains how you push through years of struggle, hire for passion and stay present at home while you build. KEY TAKEAWAYS Find the real pain before you scale. Dealers refused to use Heave's first product. The business took off once Alex focused on repairs, since only four providers in a territory could fix a machine.Act on your instincts about people. Alex says his worst mistakes were decisions he did not make. His gut told him a person was wrong for the role, and he waited too long.Stop seeking validation. Plenty of people told Alex Heave was a great idea and never bought. He learned that what people say does not matter until they act.Double down when you want to quit. Alex says you always have a move. Every company has three or four near-death experiences, and how you respond matters more than the circumstance.Hire for passion over experience. Alex warned his new salespeople the job would be harder than they thought. They missed in the first 90 days but stayed because they believed in the problem.Admit what you do not know. When Alex took over a service department he had never worked in, he told its leaders they knew it better and asked them to own the fixes. The room changed once their opinions counted.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 Alex Kraft: Website: https://www.heave.co/ LinkedIn: https://www.linkedin.com/in/alex-kraft-531408146/ Company LinkedIn: https://www.linkedin.com/company/heaveapp/ Instagram: https://www.instagram.com/heaveapp Facebook: https://www.facebook.com/Heave.co/ Medium: https://heaveapp.medium.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.

  6. 5d ago

    Health Insurance Is Not Healthcare | Harlon Pickett

    Connect With Chaz Harlon Pickett got laid off after 19 years in corporate America. When his severance benefits ran out, agents quoted his family of four $800 a month, so he got licensed to sell himself insurance. That accident put him in the insurance business in 2007. Harlon now runs Eagle Care Health Solutions and builds custom health plans for businesses and individuals. He explains why hospitals keep hundreds of prices for the same procedure and why a hospital can have five billing people for every bed. He takes no money from insurance companies and is paid only by the employer. In this conversation with Chaz Wolfe, Harlon shows you why health insurance and healthcare are two different things and how to take back control of one of the largest lines on your P&L. KEY TAKEAWAYS Own your health plan decisions. Once you pass 50 employees the law requires you to offer insurance, and it becomes your second or third largest P&L item. Do not leave that strategy to HR.Question the renewal win. A broker who talks a 15% increase down to 12% still handed you a 12% increase.Ask for the cash price. Hospitals keep hundreds of prices for the same procedure. The cash price is often far lower, and the care is the same.Look at Direct Primary Care. Members pay about $50 to $120 a month, see their doctor at no added cost and can text the doctor directly.Know who pays your broker. A traditional broker is paid by the insurance company and other vendors. Harlon is one of fewer than 500 advisors in the country paid only by the employer.Name a healthcare champion. Harlon only works with companies that assign one person to track how the plan runs. Problems get fixed during the year, not after renewal.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 Harlon Pickett: Website: https://eaglecarehealth.com/ LinkedIn: https://www.linkedin.com/in/harlon-pickett/ Facebook: https://www.facebook.com/eaglecarehealthsolutions Instagram: https://www.instagram.com/eaglecarehealthsolutions/ The Health and Wealth Power Hour: https://www.youtube.com/playlist?list=PLQRIXJqN-5oK0b-n-wE0mOus2t25NtoH5 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.

  7. 6d ago

    Why a $100K Launch That Paid Zero Was Worth It | Larry Kaul

    Connect With Chaz Larry Kaul once sat in his office at 10 o'clock at night, overwhelmed by the P and L, after his most important salesperson quit and a product line dropped his company. He stopped trying to force a fix, and the answers came fast. Years later, a product launch he expected to put $100,000 in the bank paid nothing, and his fear of criticism went away. Larry's sales outsourcing company has been passive income for about three and a half years, with someone else running it. He also founded Red Pill Pathway, an eight week program for entrepreneurs who want freedom, satisfaction, and happiness without compromise. In this conversation with Chaz Wolfe, Larry shows you how to stop copying other people and build a business around how you work. KEY TAKEAWAYS Copy yourself, not someone else. Larry tells clients to learn how business works and then find their own way through it.Ask yourself what you want, then listen. Larry says the answer comes in a moment of silence, not while you force a solution.Challenge your beliefs. Larry defines a belief as something someone told you that you accepted as true without examining it.Build the business around how you like to work. If you want to be in the trenches with people, use technology to leverage your time and price for enough margin.Learn how your answers reach you. Larry names five channels: thought, feeling, heart, visualization, and creative objects.Spend time alone every day. Pick a time and a place, cut the distractions, and ask yourself what you want.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 Larry Kaul: Website: https://www.redpillpathway.com/events LinkedIn: https://www.linkedin.com/in/larrykaul/ YouTube: https://www.youtube.com/@entrepreneurexperiment Facebook: https://www.facebook.com/larrykaul/ Instagram: https://www.instagram.com/larrykaul/ 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.

  8. Nov 3

    His Partner Died With No Key Person Insurance | Robert Poole

    Connect With Chaz In 2017 Robert Poole found his business partner of many years slumped over his computer. He had died of a heart attack the day before. Their key person insurance had lapsed, and Robert had no way to buy out the estate of a company valued at millions. Robert is a West Point graduate and Army veteran who runs Total Business Results, a B2B marketing firm built on cold calling. He stopped counting at 15,000 cold calls and figures he has made several hundred thousand. In a survey of his clients, 72% said they did not use social media in their business at all. In this conversation with Chaz Wolfe, Robert explains why cold calling still works in B2B, how to act when you are afraid, and why your business only grows as far as you do. KEY TAKEAWAYS Keep key person insurance in force if you have a partner. Robert and his partner let their term policies lapse so they could get in better shape first. They never got new policies, so Robert had no way to buy out the estate.Put your buy sell agreement in writing now. Robert wrote a two page agreement himself two years before his partner died. It required a business valuation, which gave him a way forward with the heirs.Do not assume your buyers live on social media. 72% of Robert's surveyed clients said they did not use it in their business. Owners often pick up the phone when the receptionist is out.Treat outreach as a duty. Someone out there needs your service right now. If you do not call them, a company with worse work and worse ethics will.Do the thing you fear. Robert says the only way to get rid of fear is to act. It gets easier the second time and easier every time after that.Lead people who choose to work for you. Robert ran his company top down like the military for years. Learning to hire, fire and build culture over the last 6 to 8 years paid him the most.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 Robert Poole: Website: https://www.totalbusinessresults.com/ LinkedIn: https://www.linkedin.com/in/therobertpoole/ Instagram: https://www.instagram.com/therobertpoole/ YouTube: https://www.youtube.com/@therobertpoole Facebook: https://www.facebook.com/therobertpoole 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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5
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82 Ratings

About

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 systemsSell and market with disciplineBuild a team that runs without youCreate and protect wealthLead your family with the same intent you bring to your companyChaz 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.

Information

  • Creator
    Gathering The Kings
  • Years Active
    2022 - 2026
  • Episodes
    89
  • Rating
    Clean
  • Copyright
    © 2026 Gathering The Kings
  • Show Website
    Driven To Win