Driven To Win

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.

Driven To Win is a business podcast hosted by Unknown Host, with 54 episodes on record and a Required Pod Score of 81. PitchCentric scores this show on Booking Probability, Listen Score, and live audience signals refreshed every 24 hours.

Unknown Host hosts Driven To Win, a business show with 54 episodes published.

Our AI reads these to draft pitches. Use them as grounding for a pitch that cites a real guest and a specific topic.

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  Episode #463

  463 | The Five Financial Steps That Took Coach JV from Broke to a Rockefeller Trust for His Family

  Aug 17, 202654 min

  Connect With Chaz In December 2006, John Vasquez attempted suicide. That is how he describes it. The person he was that day, a man drowning in opiate addiction and low self-worth, died. He considers it the beginning, not the end. Fourteen years later, the COVID pandemic shut down the gym he had built using Alex Hormozi's Gym Launch program, and he found himself sleeping on his parents' couch with two kids, back in the house he grew up in, watching his parents' same patterns around money and fear play out in real time. That was the moment he drew a line in the sand. Today Coach JV runs three seven-figure business ecosystems, has a Rockefeller Trust set up for his family for generations, and has built a massive social media following teaching financial literacy, micro and macroeconomics, and cryptocurrency education to people who were never taught any of it. In this conversation with Chaz Wolfe, Coach JV breaks down his 5-part financial framework, why Ray Dalio is the lens through which he reads the global economy, why paying yourself first is not just a strategy but a frequency shift, and how he is raising his kids to be the first generation to break the pattern for good. Key Takeaways: Drawing the line in the sand is not a motivational phrase. It is a moment when you become more committed to the pain of change than to the pain of staying the same. That specific shift is what changes the trajectory. You have to give up something to become something. And most people are addicted to their old self. The subconscious programming laid down in childhood drives adult behavior more than most people ever acknowledge. Coach JV's 5-part financial framework: Foundation, meaning rewire your belief system around money and trace where it came from. Financial Literacy, meaning understand what money actually is, how banks work, and what the Federal Reserve has done to the dollar since 1913. Discipline, meaning budgeting and asking do I need this or do I want this. Income Creation. And finally, Protection, Compounding, and Growth. The US dollar has collapsed 99 percent in purchasing power since the Federal Reserve was created in 1913. School, job, 401(k) is a strategy of hope. You are hoping the market aligns when you retire. That is not a plan. Pay yourself first every single time. Before bills. Before spending. Money goes into your freedom account first. What is left is what you live on. This changes your frame of mind and eliminates frivolous spending automatically. America is at 120 percent debt-to-income ratio. The average middle-class American needs to earn $160,000 per year to truly be middle class now. The regional banks are in a tough position. Bond yields inverted in 2023. These are not opinions. These are Ray Dalio's documented patterns. Cryptocurrency is going to move significantly on the back end of this cycle. But what goes up must come down hard. Buy the rumors, sell the news. When the mainstream is telling you to get in, you should have been out days ago. Define your principles before anything else. For Coach JV: business principles are integrity, honesty, and uncompromising belief in God. Personal principles are peace, freedom, and family structure. If anything disrupts those three, the answer is a hard no. A $10 million contract offer that disrupts family structure is still a no. Ask your son when he falls: are you hurt or are you scared? Manage what is hurt. Acknowledge the fear. Then get back up and do it again together. This is the framework Coach JV uses to rewire what he never received. Everything happening in the global economy right now is a historical pattern. It has happened before. When you understand the waves of energy, it is the greatest time in human history to build wealth for your family if you are paying attention. If you are a contractor business owner doing $1M+ and you feel stuck in the day-to-day, we built GTK for you. Through peer mastermind and 1:1 coaching, we help you: increase profit install real systems build a team that runs the business get your time back Visit www.gatheringthekings.com for information on how to apply. 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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  Episode #464

  464 | Why Selling Your Business to a Holding Company Could Triple Your Exit. Josh Wilson Explains the Math.

  Aug 12, 202648 min

  Connect With Chaz Josh Wilson started at seven years old on a cruise ship, charging his vacation friends a markup to use his grandfather's cruise card. He built a wedding DJ business at 16 and sold it at 19 for $25,000. His only W2 job was two months as a buggy boy at Winn Dixie before he got fired. Since then he has built a 25-million-dollar real estate portfolio, lost over a million dollars on a single investment, and pivoted to M&A where he is now acquiring his seventh company with a goal of 10 companies and 10 million in EBITDA before exiting to private equity. In this conversation with Chaz Wolfe, Josh breaks down the entire M&A framework he uses: what to look for in a target company, why he only buys companies doing at least a million in cashflow, the five reasons a contractor business owner should consider selling to a holding company instead of selling on the open market, why most businesses have not raised prices since COVID, and how the multiple arbitrage game works when you roll your equity into a holding company instead of taking a 3x exit alone. Key Takeaways: The first question in any acquisition: when was the last time they raised prices? Nine out of ten businesses Josh looks at have not raised prices in years. A 10 to 20 percent price increase is often the first value add after closing. Only buy companies doing at least one million in cashflow. Below that threshold, you cannot afford to hire the management team you need to actually run the business. You end up doing everything yourself again. A 3x multiple on your own is a mom-and-pop exit. Roll your equity into a holding company targeting 8 to 10x and you may triple your eventual payout for waiting a few years. PE companies buy cashflow, not hustle. When private equity looks at a portfolio, they want a C suite in place, a back office running, general managers in every entity, and systems that do not require the founder. Build that picture and you become attractive. Going wide to find your vertical is not always a mistake. Josh spent five years acquiring different industries to find where he could go deepest. He is now locking in on transportation. The path was the education. The mentor moment that changed everything: Josh was sitting in a hot tub during COVID, watching his real estate portfolio and wondering if his tenants were going to pay. In that moment he realized he could not keep living his entire life this way. That discomfort drove the pivot. If I can't do it, no one can is a guarantee that you will never scale. Josh learned it the hard way. The C suite he built is the only reason he can now focus exclusively on vision and growth. Pivoting is not failure. Real entrepreneurs master the art of knowing when things are heading in the wrong direction and correcting course before it costs them everything. $25,000 was enough to count as a real exit. The size of the deal does not determine whether the principle applied. Josh knew how to create value and find a buyer at 19 years old. The same principle runs his 7-company portfolio today. Build the right C suite first. CFO, COO, CEO roles need to be filled by people who love operating, not just people who are available. Josh found each one through deliberate relationships, not desperation. If you are a contractor business owner doing $1M+ and you feel stuck in the day-to-day, we built GTK for you. Through peer mastermind and 1:1 coaching, we help you: increase profit install real systems build a team that runs the business get your time back Visit www.gatheringthekings.com for information on how to apply. 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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  Episode #465

  465 | Remote Work Is Not the Problem. Your Culture Is. Chris Dyer on What No One Will Tell You.

  Aug 10, 202653 min

  Connect With Chaz Chris Dyer ran PeopleG2, a human capital company with 4,500 employees and thousands of clients. He managed that team through the 2008 financial crisis without a single layoff. He built a culture that earned best-places-to-work awards for 15 consecutive years. And when he finally stepped away from the CEO role, he described it as an elephant getting up off his chest. Now he speaks and consults on culture, remote work, and leadership, and his message to business owners is direct: the reason remote work is not working in your business is not remote work. It is your culture. In this conversation with Chaz Wolfe, Chris covers what actually separates leaders who make remote work a lightning bolt for their organization versus those who burn it down. He also breaks down why accountability and tough conversations are the foundation of any culture, how to stop micromanaging and start building top performers, and why the question every leader needs to ask themselves before any difficult conversation is not what do I think but do I want to be right or do I want to be effective. Key Takeaways: Remote work is not the problem. Leaders who cannot define success clearly, have tough conversations honestly, or give genuine autonomy will fail with remote teams. The same failures happen in the office. They are just easier to hide there. If you count keystrokes, require Teams status to always be green, and micromanage output instead of results, do not adopt remote work. You are not ready and you will blame the model instead of yourself. The companies pulling people back to office are not failing because of remote work. They are failing because their culture is broken. A tiny startup with remote culture is eating their lunch the same way they once ate bigger companies' lunch. Accountability does not disappear with friendship. Chris had 15 years of award-winning culture and still had to walk up to a 10-year friend and say: I told the client we would have this. You said you would deliver. That conversation has to happen whether or not you see each other at the holiday party. Do you want to be right or do you want to be effective? That question changes every leadership interaction. Winning an argument at the expense of a relationship or an outcome is not leadership. It is ego. Micromanagement does not fix underperformance. The answer to someone not performing is not more hands-on management. It is getting curious about why, having an honest conversation, and giving them the clarity and tools they need to succeed. Remote work gives employees their humanity back. Requiring someone to burn an entire vacation day for a 30-minute doctor's appointment is not a policy. It is a choice that communicates your real values. When you find something that works, lean into it. Stop overthinking, stop experimenting, and go hard. Chris wears white glasses because people love them. That is a business principle dressed up as an eyewear story. The same cash flow problem exists at 2 employees and at 4,500. The scale changes. The stress of keeping people whole does not. Losing 40 percent of your clients because they were all in one industry is a lesson you only pay for once. Diversify before you have to. If you are a contractor business owner doing $1M+ and you feel stuck in the day-to-day, we built GTK for you. Through peer mastermind and 1:1 coaching, we help you: increase profit install real systems build a team that runs the business get your time back Visit www.gatheringthekings.com for information on how to apply. 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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  Episode #466

  466 | What the Big Banks Know About Crypto That They Do Not Want You to Know. Tonya Evans Explains.

  Aug 5, 202647 min

  Connect With Chaz Professor Tonya M. Evans graduated from Howard University School of Law, clerked in the Third Circuit, practiced at major law firms in Philadelphia, and is now a full tenured professor at Penn State with a joint appointment in data sciences. She is also a former professional tennis player who played at Northwestern on scholarship, and she is one of the most credible voices in the country on the intersection of law, finance, and emerging technology. Her message to business owners is simple and direct: the big banks are trying to scare you out of a space they are quietly moving into themselves. JP Morgan CEO Jamie Dimon still calls Bitcoin garbage. JP Morgan is an authorized participant in the Bitcoin ETF. BlackRock, the most conservative investment firm in the world, was first in line to issue a Bitcoin ETF. The little guy is being scared away while institutional money gets positioned. In this conversation with Chaz Wolfe, Prof Tonya breaks down what blockchain actually is in plain language, the three biggest crypto myths holding business owners back, why it is not early but not late, and how to start thinking about Web3 as a business owner even if you never buy a single coin. Key Takeaways: Crypto comes from cryptography. Blockchain is a digital ledger. That is it. When someone starts throwing jargon at you, they are either confused themselves or they want you confused. It is a public record of transactions that no single entity controls. Bitcoin came on the scene January 3rd, 2009. Fewer than 8 percent of people globally hold it. If that is a fad, it is the longest fad and scam in the history of fads and scams. The banks are not scared of crypto because it is dangerous. They are scared because it threatens their dominance. Jamie Dimon calls it garbage while JP Morgan participates in the Bitcoin ETF. Follow the money, not the press release. The biggest mistake most people made in the 2021 crypto run was buying everything because the tide was rising. A rising tide lifts all boats, including the garbage ones. Holding Bitcoin through the crash and not chasing every alt coin is the lesson most people paid dearly to learn. Traditional wealth-building paths are not enough anymore. Max out your 403(b), buy a house, get rental property, ride it out. Prof Tonya followed that playbook as a high-income earner and found herself making all the money and all the mistakes simultaneously. First mover advantage is fleeting. If you are a business owner who has not thought about how blockchain and Web3 will affect your industry, start now. Not because you have to invest, but because the technology is moving with or without your awareness. Decentralized AI is the next frontier. The same centralized model problem that exists in banking is being replicated in artificial intelligence. The business owners who understand decentralization early will have options the others will not. The blockchain is public facing. The Department of Justice uses blockchain forensics regularly to recover millions in assets. It is not anonymous. It is the opposite of a dark market. Stable coins are going to matter more than most people think. For businesses operating globally or in any space without physical borders, a verifiable stable form of digital currency is not optional. It is coming. The mastermind principle applies here too. You do not have to be the expert on everything. You have to get around people who are, stay curious, and keep your saw sharpened. If you are a contractor business owner doing $1M+ and you feel stuck in the day-to-day, we built GTK for you. Through peer mastermind and 1:1 coaching, we help you: increase profit install real systems build a team that runs the business get your time back Visit www.gatheringthekings.com for information on how to apply. 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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  Episode #467

  467 | He Sold Vacuums Door to Door and Built the Largest Food Truck Company in the World. The Tony Lamb Story.

  Aug 3, 202658 min

  Connect With Chaz Tony Lamb grew up watching his father sell vacuum cleaners door to door and thought that was the pinnacle. He got a college degree, walked into a pharmaceutical sales interview, heard the number $36,000 a year, and drove straight back to the vacuum cleaner office to ask for the highest commission they would pay. Then one afternoon, his kids ran to a beat-up ice cream truck in their neighborhood, paid $22 for freezer-burned ice cream from a guy fresh out of prison, and Tony saw a gap. Two years of obsession later, he launched Kona Ice. Today Kona Ice is the largest food truck company in the world with over 1,700 units, has given back over $130 million to local communities, and spawned two additional brands. Tony did it with no debt, a clear lane, and a refusal to be anything other than the absolute best at what he does. In this conversation with Chaz Wolfe, Tony breaks down the origin story of Kona Ice, the difference between a small business owner and an entrepreneur, why pain and suffering are the best growth tools available, and what it actually takes to build a franchise that scales without you. Key Takeaways: Do not try to build a better hamburger at scale. Find the open niche, stick your foot in it, and become the undisputed best at that specific thing. Tony turned down every offer to brick-and-mortar Kona Ice and stayed in his lane. The gap between idea and action is where most businesses die. Tony talked about Kona Ice for two years before someone told him to do it or drop it. The moment the words "I'm going to do it" came out of his mouth, he was committed. If you need too much money personally to survive the early years, the business will never grow. Tony kept his personal debt load at zero, lived lean, and reinvested everything. That gave him the fortitude to build through the hard seasons. The entrepreneur and the small business owner are two completely different animals. A great small business owner who executes consistently is incredibly valuable. An entrepreneur who cannot execute is a liability. Know which one you are. Brand is not optional. A clean truck, a uniformed driver, and a reasonable price changed everything about how communities received Kona Ice. The opposite of a problem is not just the absence of the problem. It is a completely different experience. Pain and suffering are the prerequisites for real growth. Tony said the NVIDIA CEO told Stanford graduates he hoped they would have pain and suffering. Tony agreed. He intentionally launched new brands when things got comfortable because the discomfort is where the learning is. College is not the answer for everyone. The question is whether the education you are paying for will service the debt you incur to get it. Tony's kids never finished college and are all doing extremely well. The best proof your model works is when someone who is not like you runs it successfully. When the non-salesperson in Georgia started producing results with Kona Ice, Tony knew he had a real business. Wisdom is not built in a classroom. It is built by consuming knowledge relentlessly, getting around smart people, attending conferences, and staying humble enough to admit what you do not know. Family and business are not separate departments. Tony drove his kids through neighborhoods in the Kona truck, put his youngest daughter in a car seat in the front, and built the business from within his family's daily life. If you are a contractor business owner doing $1M+ and you feel stuck in the day-to-day, we built GTK for you. Through peer mastermind and 1:1 coaching, we help you: increase profit install real systems build a team that runs the business get your time back Visit www.gatheringthekings.com for information on how to apply. 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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