Driven To Win

Chaz Wolfe
  • 5.0 (2)
  • 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. 2d ago

    472 | How to Win in Business While Taking 130 Days Off Every Year. Rob Dube on The 10 Disciplines.

    Connect With Chaz Rob Dube built ImageOne into a multi-million dollar company. He then co-founded The 10 Disciplines with EOS creator Gino Wickman and co-authored their book Shine. His premise is direct: you are probably winning in business while leaving a trail of chaos behind you, in your company and at home. And you do not have to. In this conversation with Chaz Wolfe, Rob breaks down all 10 disciplines that give high-performing entrepreneurs the framework to manage their energy, make decisions from a place of clarity instead of fear, and build a business that makes a greater impact without requiring you to sacrifice everything outside of it. This is not an episode about working less because you are lazy. It is an episode about winning more because you are clearer. Key Takeaways: Hustle culture is a mantra for some and a trap for others. The real question is not how many hours you are working. It is whose dream you are living and whether the decisions you are making are driven by love or fear.Time is your greatest asset. Most entrepreneurs manage their financials more tightly than their time. That is backwards.Discipline 1, 10-Year Thinking: Stop goal setting. Start imagining. Get clear on what your life looks like 10 years from now and let that vision become your North Star. When decisions align with that picture, the chaos reduces.Discipline 2, Take Time Off: 130 days per year. Every weekend, every US holiday, three weeks vacation. That is the baseline. The hard part is not checking email on the chairlift. The payoff is a clearer mind that produces better decisions and bigger impact.Discipline 3, Know Yourself: Be 100% authentically you at all times. People can feel inauthenticity in an energy field. Send an email to five people who know you well and ask for your greatest strengths and your greatest weaknesses. Vulnerable. Enlightening. Worth doing today.Discipline 4, Be Still: 30 minutes of silence every day. Prayer, meditation, journaling, contemplation. Your ego will resist it. Do it anyway. What surfaces when you sit still is exactly what needs to be released for your mind to get clear.Discipline 5, Know Your 100%: Decide on the perfect number of hours per week and weeks per year where you deliver your greatest value. Once you know that number, everything else becomes a decision about protecting it.Discipline 6, Say No Often: As you grow, more opportunities come than you have time for. Saying no gracefully, with an alternative, frees you to make greater impact on the things that actually matter.Discipline 7, Don't Do $25/Hour Work: Calculate your hourly rate. List everything you did this week that falls below it. Start delegating every item on that list. Somebody out there loves doing that work and is better at it than you.Discipline 8, Prepare Every Night: Five to ten minutes before bed. Write out tomorrow's schedule. Your subconscious goes to work while you sleep and you wake up with solutions you did not have the night before.Discipline 9, Put Everything in One Place: One capture system for every idea, commitment, thought, and promise. Nothing gets lost. Nothing gets forgotten.Discipline 10, Be Humble: View yourself as an equal to every other person on the planet. Humility is a strength. Every consistently humble person has a daily intentional gratitude practice. Start there.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 Facebook Instagram LinkedIn YouTube  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.

    39 min

  2. 4d ago

    473 | The Visionary/Integrator Trap That Keeps Contractor Businesses Stuck: Mike Paton on EOS Done Right

    Connect With Chaz Gathering The Kings ran EOS for six months and saw almost no growth. Then in October, Chaz, Jake, and the team got crystal clear on who owned what in the accountability chart. By January, the business had doubled. They had not changed their product, their marketing, or their team. They got clear on their lanes and let everyone run. That is the episode in one story. Mike Paton has been implementing EOS for 17 years. He co-authored Get A Grip and Process with Gino Wickman, succeeded Gino as Visionary of EOS Worldwide, and has seen every way a company can get EOS right and get it wrong. In this conversation with Chaz Wolfe and Jake Isaacs, Mike breaks down the most common self-implementation mistakes, what actually separates a great integrator from a mediocre one, why your team already knows whether you are a visionary or not, and why the visionary-integrator relationship is the most important partnership in any growing business. Jake Isaacs, who has served as integrator for multiple companies and is Chaz's integrator at GTK, co-hosts the episode. His perspective makes this one of the most practical EOS conversations you will find anywhere. Key Takeaways: The number one self-implementation mistake is the smorgasbord approach: picking the EOS tools you like and skipping the ones that feel hard. The accountability chart is almost always what companies skip first. It is almost always the reason they are not growing.A vision without traction is hallucination. You need to know who is accountable for what before your VTO means anything.You are almost certainly more intimidating to your team than you think. About 50 percent of the time, the leader of the organization is the problem. An outside facilitator lets you participate as an equal alongside your team instead of inadvertently suppressing honest input.Gino Wickman told Mike he was not hardwired as an integrator. He was a visionary who was capable of integrating. There is a difference. Most entrepreneurs who score high on both in an assessment are not ambidextrous. They just know the right answers.The highest and best use test: stop asking what an assessment says about you. Ask what role will bring you the most joy and add the most value to the business. Then go do that.The four traits every great integrator must have: focus, discipline, comfort with accountability including upward accountability to the visionary, and willingness to have tough conversations and get in the muck.The visionary-integrator relationship is a partnership. It is not the integrator chasing the visionary around with a broom. When it is right, it is like a great marriage where both people can be fully themselves and together become something unstoppable.If you are hiring an integrator and you cannot picture them being better than you at execution and happier than you doing it every day, you are making a mistake.To hire growth-oriented people, Mike asks two things: do you have strong beliefs you are willing to share, and what would you do if evidence challenged those beliefs? And: what do you do in your free time to keep your saw sharpened?You can keep bringing file folders of work home and lamenting that your car is first in the lot and last to leave. Or you can get help. Those are your two options.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 Facebook Instagram LinkedIn YouTube  Connect With Jake Isaacs (Co-Host):  Website Facebook LinkedIn Instagram YouTube 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.

    42 min

  3. Jun 3

    474 | He Was Hours From Death, Lost Everything, and Rebuilt. Peter Goldstein on the Real Cost of Winning.

    Connect With Chaz During the Great Recession, Peter Goldstein lost his business, his real estate portfolio, and his marriage within three years. He also had a 90 percent blockage in his lower left ventricle and was hours away from dying. He was in his late forties, in shame, and had to decide whether to play small or rebuild from nothing. He rebuilt. Today Peter is the CEO of Exchange Listing, founder of the Emmis Capital IPO fund, and author of The Entrepreneur's IPO. He has 30 years of experience guiding small and mid-sized companies through the public markets and has watched more IPO cycles than almost anyone alive. In this conversation with Chaz Wolfe, Peter breaks down what the current capital environment actually means for contractor business owners, how to build a company that investors want to buy before you ever think about selling, the single biggest pitch mistake entrepreneurs make, and why your calendar is the most honest scorecard of what you are actually committed to. Key Takeaways: There is more money sitting on the sidelines right now than Peter has seen in his entire career, across private equity, venture capital, and institutional markets. Eight to nine consecutive quarters of downturn. When the window opens, it will not be a flood overnight. But the companies that are prepared will move first.Do not get caught drinking the Kool Aid when the market opens. The 2021 IPO market was the best in 20 years, and two and a half years later it became the worst market in 30 years. The pendulum always swings. Fundamentals protect you when it does.Build your business as if you are preparing for an exit even if you have no exit planned. Tighter systems, controls, and governance increase enterprise value for every stakeholder whether you are selling tomorrow or in 10 years.Radical humility is the most underrated skill in entrepreneurship. Be honest about where your organization is weak. Write down the deficiencies. Then build solutions for each one. That is the entire framework.The biggest mistake in an investor pitch: 36 slides and 30 minutes and the entrepreneur never stopped talking. Talk less. Listen more. Find out what is important to the investor before you tell them what is important to you.Pitching investors is the same as selling. Discovery comes before presentation. Every time.Your calendar does not lie. Look at where you spent your time in the last four weeks and you will know exactly what you are truly committed to, not what you say you are committed to.You do not have to hit rock bottom to make radical changes. Self-awareness plus a real inventory of your time is enough to show you the gap between where you are and where you say you want to be.When you are down, go back to three things: purpose, self-care, and community. Not in a vague way. Purpose means getting clear on why you are doing what you are doing. Self-care means diet, sleep, and exercise. Community means people you trust who are already in your corner before things go wrong.Peter was hours from death, lost everything, and rebuilt. His lesson: you do not need to experience that to learn from it. Take the inventory before life forces it on you.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 Facebook Instagram LinkedIn YouTube 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.

    35 min

  4. Jun 1

    475 | He Turned Down $600M. Then the FBI Raided His Office. Jeremy Delk on What Happened Next.

    Connect With Chaz Jeremy Delk grew up in a small town in Bardstown, Kentucky, lost his father at seven years old, left a Wall Street job paying twice what both his parents earned combined, and built multiple multimillion-dollar companies across industries with no plan, no roadmap, and no formula beyond genuine curiosity and an obsessive willingness to negotiate from the other side of the table. His peptide company, Tailor Made Compounding, grew from zero to $60 million in annual revenue and 150 employees. He was approached unsolicited by a buyer with a $600 million offer. He turned it down. Less than two weeks later, the FBI raided his pharmacy, took $3 million in inventory, and set off six months of the most pressure he has ever felt in his life. He came out the other side, sold the company for $6 million instead of $12 million to protect his employees during COVID, and started over. In this conversation with Chaz Wolfe, Jeremy covers how to turn competitors into allies, why genuine communication is the only negotiation strategy that works long term, what the FBI raid taught him about resilience and identity, and the parenting decision he wants every entrepreneur to steal from him immediately. Key Takeaways: People do business with people. Industry is irrelevant. The skill that matters is genuine curiosity about the person on the other side of the table. If you can have the same rapport with a billionaire and a janitor, you will never have a shortage of relationships that matter.Negotiate from the other side of the table. Before you state your position, ask what is important to them. Ask what they actually need. The deal closes faster when both people feel understood.Jeremy's rule: be the nicest guy in the room until pushed. If you have genuinely made your best effort and the other side will not meet you there, you are fully justified going nuclear. The key is that you actually have to try first.He turned down $600M because he believed the company would be worth a billion the next year. Was it arrogant? Yes. Would he do it again? Also yes. The decision made sense from where he stood, and second-guessing past decisions that were made with honest information is a waste of your best thinking.The FBI raid was not a criminal indictment. It was a regulatory gray area around a vitamin B12 distribution that became leverage for a six-month federal pressure campaign. Jeremy never got the $3 million back and was never charged. He put more money in and kept operating.The fear of freedom being taken from you is unlike any other pressure. The threat of not being able to hold your kids is the only fear that matters at that level.He sold for $6 million instead of $12 million during COVID to protect his employees from losing jobs during a pandemic. That decision cost him on paper and was completely worth it.Humans are wired to be resilient and to be self-protective. The two coexist. You can look at every hard thing you have survived and use it as proof that you can survive the next one.The fear of failure lives entirely between your ears. Most of it is driven by what you think other people will think. And the reality is: no one is thinking about you nearly as much as you think they are.Jeremy wrote his book Without A Plan for his kids. When they are old enough to find the news articles from that period, he wanted them to hear the full story in his voice first.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 Facebook Instagram LinkedIn YouTube 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.

    37 min

  5. May 27

    476 | Their Parents Took Out a $200K Second Mortgage to Fund Their Dream. Here Is What Happened Next with Jesse & Joel Worcester

    Connect With Chaz Jesse and Joel Worcester grew up in a pastor's household in Oregon. Lower middle class, not much money, dad who talked openly about financial stress. Joel wanted to play in the NBA and take care of his mom. Jesse just wanted to compete. What they shared was a simple belief: failure was not an option. When Joel and Jesse graduated, they moved their operation to Kansas City, started buying distressed properties in 2008 and 2009 while everyone else was nursing wounds from the crash, and built one of the most disciplined real estate investment firms in the Midwest. Their acquisitions team underwrote over 300 properties last year and bought two. That filter is not caution. It is the system that protects their investors and has driven returns over 15 years. In this conversation with Chaz Wolfe, Jesse and Joel open up about the $200,000 second mortgage their parents put in as seed money, the seven years they barely paid themselves, the break-the-deal process they borrowed from Blackstone to stress-test every acquisition, and why they believe the most underrated asset in any business is the right partner rowing in the same direction. Key Takeaways: Jesse and Joel's parents took a second mortgage on their home for $200,000 as the seed investment. That was everything their parents had. Failure was never an option from day one, and that pressure focused them in a way that overconfident optimism alone never could have.They entered the Kansas City market in 2008 and 2009 when no one else wanted to. They had not bought heavily at the peak, so they were not managing losses. They were acquiring great deals while everyone else was recovering.In their best years they would underwrite 300 or more deals and buy two. That discipline is the foundation of their investor return track record.They borrowed a break-the-deal process from Blackstone: bring a large team into a room and rip the deal to shreds before moving forward. Try to find every possible failure mode, assign risk mitigation to each one, run sensitivity analysis. Only then does the conversation shift to upside.Joel describes himself as a big starter who is not much of a finisher. He built a team of finishers around himself. That combination, not individual brilliance, is what scaled the company.Choosing the right partner is like choosing a spouse, and often harder to exit. Do not partner with your best friend. Find someone whose strengths complement yours, whose goals align with yours, and whose willingness to grind matches yours.Transparency with investors is the long game. When a deal misses, the question is not whether you can justify it. The question is whether you were transparent throughout and whether you did all the due diligence you should have. That standard keeps the relationship intact regardless of outcome.Most investors who get into real estate late in life invest their own capital. Jesse and Joel invested others' capital from day one. That accountability structure built their character before it built their wealth.Joel's most important lesson: the competitive drive that makes you great in business can become ego-driven arrogance if you do not have the right people around you to check it. Partners do not just complement your skills. They protect you from yourself.Business is the greatest sport that exists because you create your own scoreboard, there is always a new challenge, and teamwork is everything.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 Facebook Instagram LinkedIn YouTube 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.

    41 min

  6. May 25

    477 | Treat Your Sales Team Like a Pro Sports Roster. Ryan Groth on Recruiting, Leading, and Winning.

    Connect With Chaz Make More Money. Work Less. Win At Home. Ryan Groth is a former professional baseball player who walked away from the game and discovered that everything he knew about team performance, recruiting, coaching, and culture applied directly to sales. He founded Sales Transformation Group over a decade ago and has since trained thousands of salespeople across the contracting industry, helping companies go from $5 million to $25 million by installing the same thing every great sports team runs on: a system, a culture, and the right people in the right roles. In this conversation with Chaz Wolfe, Ryan breaks down what it actually takes to build a high-performing sales team from scratch, why the Starbucks CEO's family policy would get him fired in any serious organization, why humble confidence is the most underrated quality in a sales leader, and how to build a brand that makes the best talent come to you instead of you chasing them. He also gets direct about what he has seen in his own life: driven men who build empires and lose their families in the process. Ryan has chosen a different path, and he lays out exactly why. Key Takeaways: A manager is someone you have to follow. A leader is someone you want to follow. Know which one you are and which one your team needs.High performers do not sign their family's future to a company without a vision. If your business does not have a clear path, a compensation structure, and a track record, the best talent will politely decline and go somewhere else.Your first hire is not just about their numbers. It is about the culture they bring and the people who follow them in. One rockstar changes the standard of everyone around them. One average hire brings in more average.Build your company like a sports franchise. Locker room culture, coaching structure, ongoing training, peer comparison, and a compensation plan that is a win for both sides.If you are good at selling and can produce alone, you do not have a business yet. You have a high-paying job. The difference between the two is a team that does not need you to close every deal.Humble confidence is one of the rarest qualities in sales leadership. Arrogance comes from doing all the work yourself. Humility comes from trusting the team, the timing, and something bigger than your own effort.Who you are as a person is your brand before anyone looks at your product. The best contractors in the trades are asking whether they want Ryan's culture before they decide to buy his training. That evaluation happens before the first sales conversation.Ryan's rule: do not build your income at the expense of your marriage. The best deal you ever close does not matter if you look across the table and your wife is permanently checked out.If you have hidden skeletons, clean them up. Time reveals who you really are. In sales and in life, the reputation catches up.The difference between managing and leading in sales is the same as the difference between compliance and commitment. You can manage activity. You can only lead people.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 Facebook Instagram LinkedIn YouTube 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.

    53 min

  7. May 20

    478 | He Had No Idea How to Run a Business. He Built 7 Franchise Locations in 4 Years Anyway With Chaz & Jake

    Connect With Chaz Make More Money. Work Less. Win At Home. Chaz Wolfe was a college dropout who had never read a P&L when he sat down with a business broker at 24 to evaluate his first acquisition. He asked the broker to explain what a P&L even was. He bought the business anyway, an Edible Arrangements franchise, for roughly half a million dollars on an SBA loan. Four years later he had seven locations. In this episode, Jake Isaacs flips the mic and interviews Chaz on his 16-year entrepreneurial journey: from selling candy bars door to door as a kid to help his single mom pay for basketball trips, to building business systems that ran without him, to founding Gathering The Kings and serving hundreds of contractor business owners who want to do the same thing. This is the Chaz Wolfe origin story. No fluff. No polish. Just the real decisions, the systems thinking behind them, and the philosophy that has driven everything from location one to a remodeling company that hit $1.73 million in its first year without Chaz ever swinging a hammer. Key Takeaways: Business is business. Chaz never identified with the product. He identified with the system. When someone asked why he wanted to be the fruit guy, his response was direct: he was not going to be the fruit guy. He was going to be the guy who developed a business system and blew the roof off it.The job was always fuel, never the destination. While earning top 1% income in corporate sales, Chaz was stashing money, investing in real estate, and buying businesses. The day-to-day income funded the eventual freedom.Going from two locations to three was the moment Chaz had to work on the business instead of in it. He physically could not be in three places. That constraint forced the systems thinking that defined everything that followed.Every role handoff happened the same way: Chaz did it, brought someone in to watch, let them try it with him there, then stepped away entirely. By the time he was done, they did not need him. In fact, he was in the way.The mastermind principle is not a buzzword. Napoleon Hill's definition is specific: two or more minds working in harmony toward a definite aim. Something gets created in that interaction that did not exist before. That is what GTK is built on.If you are a 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 Facebook Instagram LinkedIn YouTube Connect With Jake Isaacs (Co-Host):  Website Facebook LinkedIn Instagram YouTube 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.

    36 min

  8. May 18

    479 | One Is 18 Years Married. One Is Twice Divorced. Two Entrepreneurs on the Most Important Decision You Will Ever Make With Chaz & Jake

    Connect With Chaz Make More Money. Work Less. Win At Home. Jake Isaacs' dad hung a poster on his bedroom wall when Jake was eight years old. It was called 21 Suggestions for Success by H. Jackson Brown Jr. #1 on the list: Marry The Right Person. This decision will determine 90% of your happiness. Jake is 42, twice divorced. Chaz married his high school sweetheart at 21 and has been married 18 years. Same generation. Same entrepreneurial world. Completely opposite stories. And in this episode, both of them sit down, get honest, and break down what they have each learned about marriage, partnership, and why the person you choose to build a life with is the single most important business decision you will ever make. This is not a marriage therapy session. It is a direct conversation about how the right spouse amplifies everything you build and how the wrong one creates a ceiling on all of it. Chaz also breaks down exactly how he would fill his pipeline if he were dating in 2024, including the criteria he would use and why most people are running a broken selection process. Key Takeaways: Entrepreneurs face a 50% divorce rate on their first marriage, higher than the general population. That number is not a warning label. It is a system problem. The inputs are wrong before the marriage even starts.Marrying the right person is not a feeling decision. It is a values, vision, and direction decision. When those align, the partnership creates something that was not there before.Napoleon Hill calls it the mastermind principle: two or more minds working in harmony create a third force. Chaz and Julie have been doing this for 18 years, and the compounding effect is real. Jake describes his own experience as herky-jerky because the consistency was never there.Chaz's view on love is built on three layers: duty first, honor second, intimacy third. Duty means you do what you said you would do. Honor means you treat her uniquely because you value her. Intimacy is the result of both done well over time.Your marriage is the most underutilized asset in your business. When it is working, you move with freedom and power. When it is not, you move with weight and anxiety. The two cannot be separated.If you are a 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 Facebook Instagram LinkedIn YouTube Connect With Jake Isaacs (Co-Host):  Website Facebook LinkedIn Instagram YouTube 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
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5
out of 5
2 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
    45
  • Rating
    Explicit
  • Copyright
    © 2026 485188
  • Show Website
    Driven To Win

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