Driven To Win

Chaz Wolfe
  • 5.0 (83)
  • ENTREPRENEURSHIP
  • UPDATED WEEKLY

Driven To Win is the podcast for entrepreneurs who refuse to choose between building a successful business and building a strong family. Hosted by serial entrepreneur Chaz Wolfe, the show is built for business owners who want to scale their companies, lead stronger teams, and create a life that wins both at work and at home. Chaz built and scaled multiple businesses by his late twenties, becoming a millionaire by 29 and a multi-millionaire soon after through ventures in franchising, home services, real estate, and online education. His approach centers on leadership, systems, and structure that allow businesses to grow without the owner carrying all the weight. On Driven To Win, Chaz sits down with elite entrepreneurs, business leaders, authors, and operators to break down the real strategies behind growth. These are not surface level conversations. Each episode focuses on the practical disciplines required to build companies that run through strong leadership, clear structure, and effective sales systems. But business success is only half the conversation. Driven To Win is built around the belief that true success means winning in all areas of life. That includes business, family, health, faith, and lifestyle. Through honest conversations and practical insights, the show challenges entrepreneurs to build businesses that support their family life instead of competing with it. Listeners will learn how to: • Scale a business through leadership and systems • Develop stronger sales and operational discipline • Build teams that reduce owner dependence • Lead their family with the same intentionality they lead their company • Create a legacy that lasts beyond the business Whether you are building your first company or scaling an established business, Driven To Win delivers clear strategies and real conversations with leaders who are committed to growth in every area of life. If you are serious about building a business that creates freedom instead of pressure, this podcast is for you.

  1. 1D AGO

    487 | He Built a $100M+ AI Company From a Cabin in the Woods With Richard White

    Connect With Chaz Richard White built the number one rated AI tool across 100,000 products on G2 with zero marketing spend, a team of three engineers for most of the company's life, and a single growth metric: 4% better every week. That compounds to 7x per year. He did not track monthly goals. He did not run sprints. He eliminated every meeting that did not move the product forward and stayed in his zone of genius while everyone around him handled everything else. Fathom AI is the note-taking tool Chaz and the GTK team use every day. In this conversation, Richard breaks down how he built it, how he cold-emailed his way into the Zoom marketplace three weeks after starting the company, and why speed is the only currency that actually matters in a fast-moving market. This is not a personality-driven episode. It is a systems and strategy episode. If you run a contractor business doing $1M+ and you want a framework for moving faster with less noise, this one is worth a listen. Key Takeaways: Richard launched Fathom in 2020 when investors were skeptical of AI. He bet that transcription costs would drop to near zero and AI quality would become exceptional. Both happened faster than expected.Richard cold-emailed one person at Zoom three weeks after founding the company. That email got them into the Zoom marketplace launch and changed everything. The best things that have happened in his career came from cold outreach.His growth target is 4% per week. That is it. Simple enough to never need to recompute, specific enough to hold the team accountable every seven days.Richard compares a first startup to playing Minecraft for the first time with no instructions. A second or third startup is playing after watching 10,000 hours of gameplay. Every strategy question that felt like an essay question becomes multiple choice.The biggest mistake from his previous company: handing off his zone of genius too early. He gave away product ownership to people he hired, became a manager instead of a product builder, and slowed everything down.Fathom spent a year refining the product before a real public launch. The standard was simple: can 50 people use this every single day without complaints? Until the answer was yes, they were not done.Most companies treat customer support as a cost to minimize. Richard treats it as product intelligence. Great support reveals exactly what to fix next.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 profitinstall real systemsbuild a team that runs the businessget your time backVisit www.gatheringthekings.com for information on how to apply. Connect with Chaz Wolfe (Host): Website: http://www.gatheringthekings.com Facebook: https://www.facebook Vacation With Entrepreneurial FamiliesEntrepreneur families grow closer, dream bigger, & build legacy together. Join our Family Vacation.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.

    44 min

  2. 6D AGO

    488 | If Your Marriage Is Struggling, Your Business Has a Ceiling. Here Is How to Fix Both With Austin Holt

    Connect With Chaz Most contractor business owners treat their marriage like a hobby and their business like a lifestyle. Austin Holt says that gap is exactly why both are underperforming. Austin is the founder of Conscious Christian Marriage, a certified marriage coach, and a multi-business owner. He has worked with entrepreneurs and couples for over a decade, including GTK members and their spouses. His take is direct: if you say your marriage is your top priority but your calendar, bank statements, and daily habits say otherwise, you are out of integrity. And that integrity gap bleeds into every part of your business. In this in-person conversation with Chaz Wolfe, Austin breaks down the three steps every entrepreneur needs to take to fix a strained marriage, why compromise is a victim's word and win-wins are a king's word, and how your spouse is the most underutilized asset in your entire business operation. Key Takeaways: Approach your marriage the way you approach your business: with values, vision, mission, agreements, and a scorecard. Most couples run on expectations. That is not a system.If your business is not giving you time, money, and energy, it is not set up correctly. A broken business model is a marriage problem, not just a business problem.If your marriage is your stated top priority but you are only winning in business, that internal misalignment will cause you to sabotage your own success. You will not want to bring wins home to a marriage that does not feel like home.Austin does not believe in compromise. Compromise means someone loses. Win-wins mean you get creative enough that both people get what they want.The greatest point of leverage in a man's life is his marriage. When it is working, everything overflows. When it is not, you are building on a cracked foundation.Men connect emotionally after sex. Women connect emotionally before sex. Understand that dynamic and stop waiting until 11:30pm when you are already depleted.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 profitinstall real systemsbuild a team that runs the businessget your time backVisit www.gatheringthekings.com for information on how to apply. Connect with Austin Holt (Guest): Website: https://austinjholt.com/ Instagram: https://www.instaustinjholtagram.com/austinjholt/?hl=en Facebook: https://www.facebook.com/austinjholt/ Connect with Chaz Wolfe (Host): Website: http://www.gatheringthekings.com Facebook: https://www.facebook.com/chazwolfe/ Instagram: Vacation With Entrepreneurial FamiliesEntrepreneur families grow closer, dream bigger, & build legacy together. Join our Family Vacation.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.

    51 min

  3. APR 13

    489 | He Has Parkinson's. They Rowed 2,800 Miles Anyway. The Human Powered Potential Story.

    Connect With Chaz In the summer of 2023, four men climbed into a single rowing boat in Monterey, California and rowed 2,800 miles to Hawaii. They were at sea for 41 days. By the time they reached the Hawaiian shore and fell into their families' arms, they had raised over $41 million for the Michael J. Fox Foundation for Parkinson's Research. More than 26,000 individual donors contributed to the campaign. Their fundraising goal started at $28 million, one million for every hundred miles. They blew past it. Then they raised their goal to $41 million to honor the 41 days on the ocean. They blew past that too. But this episode is not really about the numbers. It is about what happens to a man when the vastness of the ocean removes every distraction and leaves only what actually matters: the men beside him and the family waiting at the finish line. Brendan Cusick, Peter Durso, Scott Forman, and Patrick Morrissey join Chaz Wolfe and Jake Isaacs to talk about the darkest moments of the row, what it means to show up for each other when you have nothing left, and why the emotional recovery took far longer than the physical one. Key Takeaways: You cannot prepare for the vastness of the ocean. Pat Morrissey describes days of flat, dead water where every shift felt like you had not moved at all. The mental challenge dwarfed the physical.When Pete Durso found out on day 20 that the trip would take a week longer than expected, he broke down on deck. Scott came up and held him. That is all it took to keep going.Scott Forman says the physical recovery was easy. The emotional recovery took months and still hits him when he recounts specific moments.Pat has Parkinson's. Rowing suppressed his tremors almost completely while he was on the oars. When they stopped, the symptoms returned. During storms and sleep deprivation, his team covered for him without hesitation.On day three, in the middle of a violent storm, Scott and Brendan looked at each other after hours on deck, soaked and depleted, and said nothing. They just pulled up the anchor and started rowing again. That was the moment commitment became absolute.Scott said he did not do this for himself. He did it for the three men beside him. Every one of them said the same thing about the others.Pat's lesson from the row: surround yourself with the right people and you can do anything.Brendan's message after landing: when you put your heart and mind into something, anything is possible. But it has to be true. It has to come from the heart.Being vulnerable as a man is not weakness. Pete says fully embracing help from his teammates was one of the most important lessons of his life. He wishes he had learned it at 20.The community of 26,000 donors sending messages of support at the exact right moments became the team's emotional fuel when their own was gone.Connect with Chaz Wolfe (Host): Website: http://www.gatheringthekings.com Facebook: Vacation With Entrepreneurial FamiliesEntrepreneur families grow closer, dream bigger, & build legacy together. Join our Family Vacation.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.

    1h 8m

  4. APR 8

    490 | He Spent 7 Years in Prison for a Crime He Didn't Commit. Here Is How He Built an Elite Life After With Sean Michael Crane

    Connect With Chaz Sean Michael Crane spent seven years behind bars for a crime he did not commit. He walked in as a man who had wasted a decade to addiction, broken promises, and a life that did not match who he wanted to be. He walked out with a mission. Today Sean is the Founder and CEO of Unstoppable 365, a self-mastery program that has helped men lose 100 pounds, rebuild their marriages, commit to sobriety, and build businesses that give them back their identity and their family. In this conversation with Chaz Wolfe, Sean gets direct about the real reasons men stay stuck, why your "why" might not be strong enough to actually move you, how to build the kind of track record that earns your spouse's trust, and what it takes to reset your identity at any stage of life. If you are a contractor doing $1M+ who is winning in business but losing at home, this episode will challenge you to look in the mirror and make a decision. Key Takeaways: The moment a prospect hesitates to commit is not an objection. It is a coaching moment. It reveals how they make every decision in their life.When you operate from fear and doubt, you never get what you want. Delay is not caution. It is the same pattern that is already keeping you stuck.Most men say their wife and kids are their why. Sean challenges that directly: if that were true, your actions would already align with it.Sean spent 10 years running from his problems before prison forced him to stop and face himself. Most men never get that forced reckoning. They have to choose it.Personal development creates professional success across the board. When you change who you are, everything you put your name on changes with it.If there is no harmony at home, it bleeds into the business. If the business is consuming you, it bleeds into home. The two are not separate problems.Most men already know what they need to do. The problem is they do not believe they are worth it. That belief is changeable, but it requires repetition and environment.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 profitinstall real systemsbuild a team that runs the businessget your time backVisit www.gatheringthekings.com for information on how to apply. Connect with Sean Michael Crane (Guest): Website: https://seanmichaelcrane.com/  Unstoppable 365: https://unstoppable365.com/  Instagram: https://www.instagram.com/sean_crane_official/  Connect with Chaz Wolfe (Host): Website: http://www.gatheringthekings.com Facebook: https://www.fa Vacation With Entrepreneurial FamiliesEntrepreneur families grow closer, dream bigger, & build legacy together. Join our Family Vacation.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.

    40 min

  5. APR 6

    491 | Most Contractors Are Losing Sales Not From Lack of Leads, But From These 5 Mistakes With Chaz Wolfe

    Connect With Chaz Most contractor business owners think their revenue problem is a lead problem. Go get more leads, close more deals, done. But Chaz Wolfe has trained thousands of salespeople across multiple industries, generated millions in W2 commission personally, and built companies that produce consistent sales revenue. His take is direct: more leads do not fix a broken sales process. They just expose it faster. In this solo episode, Chaz breaks down the five core principles that have driven millions in sales for him and his clients. These are not tactics. They are the fundamentals that every contractor business owner needs to install in themselves and their team to convert more leads, close without pressure, and build a pipeline that actually runs. If your close rate is inconsistent, if your team is ad-libbing the sales process, or if you are leaving money on the table every single week, this episode is the reset you need. Key Takeaways: Resilience is not a mindset you are born with. It is a decision you make every time you pick up the phone after a no.The more no's you get, the more deals you close. When you internalize that, rejection stops being the enemy and becomes the engine.You should never try to be someone you are not in a sales conversation. Prospects pick up on it immediately and trust disappears.Active listening is not just being quiet. It means your next question is built from their last answer, not from your script.The more deeply you understand a prospect's real problem, the less you have to sell. The product sells itself when the fit is obvious.The sales process is four steps: open, discovery, presentation, close. In that order. Every time. No exceptions.A confused mind does not buy. Keep the presentation simple, logical, and tied directly to what they told you in discovery.Hard closing is usually a symptom of a broken discovery, not a closing problem. Fix discovery and closing gets easy.The best salespeople review their calls, track their numbers, and drill the process even when they are already winning.Average input does not produce above-average output. If you want to double or triple the business, you have to master the inputs.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 profitinstall real systemsbuild a team that runs the businessget your time backVisit www.gatheringthekings.com for information on how to apply. Connect with Chaz Wolfe (Host): Website: http://www.gatheringthekings.com Facebook: https://www.facebook.com/chazwolfe/ Instagram: https://www.instagram.com/gtkfamilymastermind/ LinkedIn: Vacation With Entrepreneurial FamiliesEntrepreneur families grow closer, dream bigger, & build legacy together. Join our Family Vacation.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.

    25 min

  6. APR 1

    492 | He Helped Clients Go From $20M to $600M... Here Is What Most Entrepreneurs Get Wrong About Marketing With Wayne Mullins

    Connect With Chaz Wayne Mullins helped a client grow from $20 million to over $600 million in less than five years. He has trained more than 20,000 marketers. He has launched New York Times bestsellers. And when Chaz asks him his number one success in business, Wayne's answer has nothing to do with any of that. In this episode, Wayne breaks down the marketing mistakes that are bleeding your business dry, including why the Boost Post button is designed to take your money, why AI content is making most businesses look lazy, and why being better than your competitor is actually a path to failure. Then the conversation shifts to something most marketing experts never touch: how Wayne built a thriving family life, a high-performing team, and a culture of self-accountability while running one of the most successful marketing agencies in the country. If you are a contractor business owner doing $1M+ who wants to market smarter, lead better, and actually be present at home, this episode delivers on all three. Key Takeaways: Being slightly better than a competitor is not a strategy. The only thing that creates separation is being different.77% of people can still tell the difference between AI-generated content and human-written content. AI that sounds too perfect loses the reader.Good copy is a dialogue, not a monologue. Shorter sentences, more conversational, less like an English class essay.The Boost Post button is designed for one thing: to make Facebook money while making you feel like your marketing is working.You cannot put a like, a share, or a comment into your bank account. Marketing exists to create customers, not engagement metrics.Wayne's biggest success is not a client win. It is 22 years of marriage and four kids who actually want to spend time together.Presence is a decision. Wayne spent the first seven years blaming the business. The day he changed the story he told himself, everything changed.The most difficult person you will ever lead is the one looking back at you in the mirror.Culture is a reflection of your thinking. Sloppy thinking builds a sloppy business.62% of employees globally are disengaged. Most do not understand where the company is going, why it matters, or what their role is in getting there.Trust is the default. Your team should have to earn suspicion, not earn trust.Over-communication is not annoying. Silence creates questions. Questions create doubt. Doubt erodes trust.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 profitinstall real systemsbuild a team that runs the businessget your time backVisit www.gatheringthekings.com for information Vacation With Entrepreneurial FamiliesEntrepreneur families grow closer, dream bigger, & build legacy together. Join our Family Vacation.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.

    44 min

  7. MAR 30

    493 | Why 97% of Business Owners Fail at Goal Setting (And How to Be in the 3%) With Chaz & Jake

    Connect With Chaz Most business owners set goals in January and abandon them by March. Not because they lack ambition. Because they lack a plan. In this episode, Chaz Wolfe and Jake Isaacs break down the exact annual planning framework they use inside Gathering The Kings to help contractor business owners reverse engineer their biggest goals into a daily roadmap they can actually execute. If you have been running the business by feel and hoping the year turns out right, this episode is your reset. Key Takeaways: Only 3% of goal-setters write their goals down. Be in that 3%.Zoom out first. Annual planning starts by seeing the whole year from 30,000 feet, not from your desk.You are not missing a revenue number. You are missing the indicators that get you there.Reverse engineer everything. Start with December and work backwards to today.The right goal scares you a little. If it does not, you set it too low.Set goals in every category: business, marriage, health, faith, and lifestyle.Big goals without a plan create shame. Big goals with a plan create belief.Community accelerates everything. The people around you are either raising your ceiling or capping it.Going public with your goals adds integrity pressure that drives follow-through.A decision is a commitment to cut off every other option. Treat it that way.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 profitinstall real systemsbuild a team that runs the businessget your time backVisit www.gatheringthekings.com for information on how to apply. Connect with Chaz Wolfe (Host): Website: http://www.gatheringthekings.com Facebook: https://www.facebook.com/chazwolfe/ Instagram: https://www.instagram.com/gtkfamilymastermind/ LinkedIn: https://www.linkedin.com/in/chaz-wolfe-86767054/ YouTube: https://www.youtube.com/@gatheringthekings Connect With Jake Isaacs (Co-Host):  Website: http://www.gatheringthekings.com Facebook: https://www.facebook.com/jake.isaacs.56 LinkedIn: https://www.linkedin.com/in/jake-isaacs-28071b41/ Instagram: https://www.instagram.com/gtkfamilymastermind/ YouTube: https://www.youtube.com/@gatheringthekings Vacation With Entrepreneurial FamiliesEntrepreneur families grow closer, dream bigger, & build legacy together. Join our Family Vacation.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.

    56 min

  8. MAR 25

    494 | How to Turn Passion Into a Profitable Business With Eric Cogorno

    Connect With Chaz Most entrepreneurs start with passion. But passion alone does not build a business. In this episode of Driven To Win, Chaz Wolfe sits down with golf coach and entrepreneur Eric Cogorno to break down how passion becomes profit when paired with clarity, consistency, and disciplined execution. Eric shares how he went from in person golf coaching to building a powerful online brand with a massive YouTube following and a thriving digital coaching business. His story is a real example of what happens when someone commits to a long term vision and keeps showing up even when growth is slow. This conversation dives into the principles that apply to both business and life. Eric explains how the same mindset that improves your golf swing also improves your business results. Identify the real problem. Focus on repetition. Commit to the process. If you are building a brand, growing an audience, or trying to turn your expertise into income, this episode will challenge how you think about consistency and long term success. KEY TAKEAWAYS • Why passion only works when paired with discipline • The real role consistency plays in building a brand • How Eric used YouTube to build authority and audience • Why your first content will never be perfect and why that is good • The connection between golf improvement and business growth • Why personal development shapes long term success • How entrepreneurs can grow a business without sacrificing family priorities Connect with Chaz Wolfe (Host): Website: http://www.gatheringthekings.com Facebook: https://www.facebook.com/chazwolfe/ Instagram: https://www.instagram.com/gtkfamilymastermind/ LinkedIn: https://www.linkedin.com/in/chaz-wolfe-86767054/ YouTube: https://www.youtube.com/@gatheringthekings Vacation With Entrepreneurial FamiliesEntrepreneur families grow closer, dream bigger, & build legacy together. Join our Family Vacation.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.

    56 min
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5
out of 5
83 Ratings

About

Driven To Win is the podcast for entrepreneurs who refuse to choose between building a successful business and building a strong family. Hosted by serial entrepreneur Chaz Wolfe, the show is built for business owners who want to scale their companies, lead stronger teams, and create a life that wins both at work and at home. Chaz built and scaled multiple businesses by his late twenties, becoming a millionaire by 29 and a multi-millionaire soon after through ventures in franchising, home services, real estate, and online education. His approach centers on leadership, systems, and structure that allow businesses to grow without the owner carrying all the weight. On Driven To Win, Chaz sits down with elite entrepreneurs, business leaders, authors, and operators to break down the real strategies behind growth. These are not surface level conversations. Each episode focuses on the practical disciplines required to build companies that run through strong leadership, clear structure, and effective sales systems. But business success is only half the conversation. Driven To Win is built around the belief that true success means winning in all areas of life. That includes business, family, health, faith, and lifestyle. Through honest conversations and practical insights, the show challenges entrepreneurs to build businesses that support their family life instead of competing with it. Listeners will learn how to: • Scale a business through leadership and systems • Develop stronger sales and operational discipline • Build teams that reduce owner dependence • Lead their family with the same intentionality they lead their company • Create a legacy that lasts beyond the business Whether you are building your first company or scaling an established business, Driven To Win delivers clear strategies and real conversations with leaders who are committed to growth in every area of life. If you are serious about building a business that creates freedom instead of pressure, this podcast is for you.

Information

  • Creator
    Chaz Wolfe
  • Years Active
    2022 - 2026
  • Episodes
    30
  • Rating
    Explicit
  • Copyright
    © 2026 485188
  • Show Website
    Driven To Win

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