Chaz Wolfe
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 tha...
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476 | Their Parents Took Out a $200K Second Mortgage to Fund Their Dream. Here Is What Happened Next with Jesse & Joel Worcester 27.05.2026 41:06
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, s...
477 | Treat Your Sales Team Like a Pro Sports Roster. Ryan Groth on Recruiting, Leading, and Winning. 25.05.2026 53:22
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,...
478 | He Had No Idea How to Run a Business. He Built 7 Franchise Locations in 4 Years Anyway With Chaz & Jake 20.05.2026 36:04
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 se...
479 | One Is 18 Years Married. One Is Twice Divorced. Two Entrepreneurs on the Most Important Decision You Will Ever Make With Chaz & Jake 18.05.2026 51:11
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 1...
480 | He Applied for 64 Credit Cards at 21 and Cash Advanced $97K. Here Is What Happened Next with Fernando Angelucci 13.05.2026 44:41
Connect With Chaz Fernando Angelucci graduated from University of Illinois with an engineering degree, landed a job at Dow Chemical with a pension, a 401K, a truck, and an expense account, and was completely miserable within six months. Thirteen months into the job, the night after he quit, he applied for 64 credit cards. Twelve got approved. He cash advanced $97,000 and went all in on real estate...
482 | $0 to $1.73M in 12 Months: The 6 Steps Chaz Wolfe Used to Build His Remodeling Company from Scratch 11.05.2026 46:28
Connect With Chaz Make More Money. Work Less. Win At Home. Chaz Wolfe launched a remodeling company in early 2023 knowing nothing about construction. He had never swung a hammer on a client job. He did not know the trades. What he knew was how to build a team, create a sales process, and design a client experience that makes people say yes and refer their friends. In twelve months, Kings Collectiv...
483 | Most Entrepreneurs Are Wasting a Full Week Every Month. Joe Rare on What to Delegate First. 06.05.2026 51:21
Connect With Chaz Make More Money. Work Less. Win At Home. If you are spending two hours a day checking email, you are losing a full week every month to a task someone else could handle for $10 an hour. Joe Rare figured this out early, outsourced everything he possibly could, and built multiple seven-figure businesses from a mountain town in Bozeman, Montana with a team based largely in the Philip...
484 | Shiny Object Syndrome Is Killing Your Business. Brian Decker on Focus, Wealth, and the Bitcoin Cycle 04.05.2026 46:09
Connect With Chaz Make More Money. Work Less. Win At Home. Brian Decker turned $500,000 into $7 million in crypto in under 12 months. The cycle before that, he turned $50,000 into $400,000. This is not luck and it is not gambling. It is a data-driven approach to understanding economic seasons, money supply cycles, and the four-year Bitcoin halving pattern that has played out the same way every sin...
485 | He Took a One-Way Ticket to Florida with Two Suitcases and Built a 200-Location Franchise Empire With Charles Bonfiglio 29.04.2026 37:29
Connect With Chaz Make More Money. Work Less. Win At Home. Charles Bonfiglio left Brooklyn at 21 years old with two suitcases, a one-way plane ticket to Florida, and a dream of opening a car stereo shop. He could not get a loan. He could not get a landlord to take him seriously. So he found franchising, used it as leverage, and never looked back. Fifteen years after buying a six-store chain called...
486 | Work-Life Balance Is a Lie. Here Is What High-Performing Entrepreneurs Do Instead With Chaz & Jake 27.04.2026 41:11
Connect With Chaz Make More Money. Work Less. Win At Home. Most business owners have been chasing the wrong thing. Work-life balance sounds reasonable until you actually examine it. Balance implies that to give more to one area, you have to take from another. Chaz Wolfe says that is the wrong model entirely, and it is quietly limiting what contractors believe is possible at home and in business. I...
481 | 6 Personal Habits That Are Quietly Killing Your Business (And How to Fix Them) With Chaz Wolfe 22.04.2026 29:33
Connect With Chaz Most contractor business owners are looking for the next system, the next hire, or the next revenue strategy. What they are not looking at is the personal habits that are quietly capping everything they are trying to build. Chaz Wolfe has made every single one of these six mistakes himself. He built and scaled multiple businesses, became a millionaire by 29, and still had to conf...
487 | He Built a $100M+ AI Company From a Cabin in the Woods With Richard White 20.04.2026 44:19
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...
488 | If Your Marriage Is Struggling, Your Business Has a Ceiling. Here Is How to Fix Both With Austin Holt 15.04.2026 51:17
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 spous...
489 | He Has Parkinson's. They Rowed 2,800 Miles Anyway. The Human Powered Potential Story. 13.04.2026 1:08:29
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...
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 08.04.2026 40:12
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, commi...
491 | Most Contractors Are Losing Sales Not From Lack of Leads, But From These 5 Mistakes With Chaz Wolfe 06.04.2026 25:02
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 ju...
492 | He Helped Clients Go From $20M to $600M... Here Is What Most Entrepreneurs Get Wrong About Marketing With Wayne Mullins 01.04.2026 44:08
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 b...
493 | Why 97% of Business Owners Fail at Goal Setting (And How to Be in the 3%) With Chaz & Jake 30.03.2026 56:01
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 h...
494 | How to Turn Passion Into a Profitable Business With Eric Cogorno 25.03.2026 55:30
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 w...
495 | How Entrepreneurs Win by Doing More With Less With Chaz & Jake 23.03.2026 44:48
Connect With Chaz Most businesses are not failing because of a lack of opportunity. They are failing because of inefficiency. In this episode of Driven To Win, Chaz Wolfe and Jake Isaacs break down the powerful principle of doing more with less. They explore how entrepreneurs think differently about efficiency, leadership, and resource management compared to large organizations and government syst...
496 | How Entrepreneurs Build Real Influence Through Clear Thinking and Writing With Jeff Goins 18.03.2026 53:02
Connect With Chaz Many entrepreneurs want influence. But influence does not start with followers. It starts with clarity. In this episode of Driven To Win, Chaz Wolfe sits down with bestselling author Jeff Goins to talk about the real foundation of influence, clear thinking and strong communication. Jeff explains why writing is one of the most powerful tools entrepreneurs have for sharpening their...
497 | The Real Secret to Building a Business Legacy Starts at Home With Andy Hobaica 16.03.2026 1:02:23
Connect With Chaz Most entrepreneurs say they want to build a legacy. But very few define what legacy actually means. Is it revenue? Growth? Recognition? Or is it the people you raise, the culture you build, and the leaders you develop along the way? In this episode of Driven To Win, Chaz Wolfe sits down with Andy Hobaica, a third generation entrepreneur who understands that lasting success requir...
498 | AI Will Not Replace Sales. Weak Salespeople Will With Glenn Poulos 11.03.2026 53:28
Connect With Chaz AI is changing business faster than most entrepreneurs are ready for. Sales systems are evolving. Automation is accelerating. Tools are becoming more powerful every year. But one thing has not changed. People still buy from people. In this episode of Driven To Win, Chaz Wolfe sits down with Glenn Poulos, co founder and leader at Gap Wireless, to break down how entrepreneurs can l...
499 | From Technician to True Business Owner With Dominic Rubino 10.03.2026 59:22
Connect With Chaz Most trades business owners start as great technicians. Then the business grows. The jobs pile up. The team expands. And suddenly the owner is buried in work with less time, less clarity, and more pressure than ever. In this episode of Driven To Win, Chaz Wolfe sits down with Dominic Rubino, host of Profit Tool Belt and a trusted advisor to trades business owners across North Ame...
500 | Your Circle Is Your Ceiling With Members of Gathering The Kings 02.03.2026 1:07:51
Connect With Chaz You will not outgrow your circle. In this milestone 500th episode of Driven To Win, Chaz Wolfe gathers a group of high-performing entrepreneurs around a fire in Cabo, Mexico for a raw conversation about growth, legacy, and the power of proximity. This is not a theory session. It is a real discussion between business owners who have experienced the weight of leadership, the loneli...
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