BusinessEntrepreneurshipManagementKids & FamilyParenting

Driven To Win

Gathering The Kings

Driven To Win is the podcast for entrepreneurs who want to build a profitable business without losing their family along the way. Hosts Chaz Wolfe and Jake Isaacs interview founders, CEOs, investors, and authors about the decisions, habits, failures, and relationships behind real results.

Across more than 500 conversations, the show covers how to:

Scale a business through leadership and systems
Sell and market with discipline
Build a team that runs without you
Create and protect wealth
Lead your family with the same intent you bring to your company

Chaz built and scaled companies in franchising, home services, real estate, and online education, and became a millionaire by 29. Jake is co-founder and integrator of Gathering The Kings, a peer mastermind for established business owners.

If you own a business doing $1M or more and want peers who hold you accountable in business and at home, learn more at gatheringthekings.com.

Play

Open in

26 episodes
daily
Avg 46 min
English

Support the show

Goes straight to the publisher. podnod takes nothing.

Support this Podcast

Episodes 26

Newest Oldest Longest

All20 Unplayed20 In progress0 Played0

Counted on this page — what you have heard stays on this device, so it is not something the list can be paged by.

#431
Yesterday · 54 min
Every Hire Should Triple Customer Experience | Holly Jean Jackson
Connect With Chaz Holly Jean Jackson built new projects inside companies like Visa, Treasury Wine Estates and the University of California. She kept getting laid off, and each layoff came with a big health challenge. She saw the pattern and left corporate America to build her own business. Today she is a revenue and performance consultant for business leaders, authors and speakers. When mature clients tell her margins dropped 30 to 50% in a quarter, she often finds five profit leaks on the first call. She also wrote the book and hosts the podcast Inspiration Contagion. In this conversation with Chaz Wolfe, Holly explains how to find your superpower, when to make your first hire, and how to protect your team from a bad apple. KEY TAKEAWAYS Ask the people closest to you what your superpower is. Buy a friend a coffee and ask what they highlight when they introduce you. Holly says the answers come quickly. Block your day around your energy. Group similar tasks so your brain is not switching all day. Expect it to take a year or two to find the schedule that fits you. Learn a task before you outsource it. Know the process, the expectation, and the impact on customers and employees. Then hand it to someone you trust. Hire when work is piling up and not firing you up. Most first hires are an assistant for scheduling, invoicing and admin. Then run the revenue ideas you never had time for. Make every hire raise your customer experience. Holly says each hire should make it at least three times better. If it does not, ask why you are hiring. Test new hires before full time. Holly uses a 30 day contract, then a 90 day contract with specific KPIs. Remove a bad apple fast because you cannot change a person's values. If you are a contractor business owner and you want to make more money, work less, and win at home, we built something for you. Get the free Owner Time Audit at gatheringthekings.com/timeaudit. It is a simple worksheet that shows you where your week really goes. We email it to you as a PDF within minutes. Connect with Chaz Wolfe (Host): Website Facebook Instagram LinkedIn YouTube Connect With Holly Jean Jackson: Website: https://hollyjeanjackson.com/ LinkedIn: https://www.linkedin.com/in/hollyjjackson/ Instagram: https://www.instagram.com/coachhollyjeanjackson/ Facebook: https://www.facebook.com/hollyjeanjackson/ YouTube: https://www.youtube.com/channel/UC3ElvJLGqpJ2ThA9utJCqMg Linktree: https://linktr.ee/coachhollyjackson Support the show Like what you heard? Share this episode with a friend and leave us a review on Apple Podcasts or Spotify! Join the conversation by visiting GatheringTheKings.com and apply to connect with other high-performing entrepreneurs and their families.
- Transcript
- Chapters
#432
Friday · 52 min
The 2.5 Year Pivot Behind the Uber of Heavy Equipment | Alex Kraft
Connect With Chaz Alex Kraft spent 16 to 17 years at a heavy equipment dealership, starting in sales and rising to chief operating officer before the company was sold. His first version of Heave helped contractors buy and rent equipment online, but dealers refused to use it, and he ground for two and a half years. Then he found the real pain: getting broken machines fixed. Heave is now a labor marketplace that connects equipment owners with independent mechanics, which Alex calls Uber for heavy equipment repairs. Customers pay a fraction of the dealership price, and the mechanic keeps more of the value he creates. After Heave raised Silicon Valley venture capital in August, Alex hired salespeople from the industry for passion over experience. In this conversation with Chaz Wolfe, Alex explains how you push through years of struggle, hire for passion and stay present at home while you build. KEY TAKEAWAYS Find the real pain before you scale. Dealers refused to use Heave's first product. The business took off once Alex focused on repairs, since only four providers in a territory could fix a machine. Act on your instincts about people. Alex says his worst mistakes were decisions he did not make. His gut told him a person was wrong for the role, and he waited too long. Stop seeking validation. Plenty of people told Alex Heave was a great idea and never bought. He learned that what people say does not matter until they act. Double down when you want to quit. Alex says you always have a move. Every company has three or four near-death experiences, and how you respond matters more than the circumstance. Hire for passion over experience. Alex warned his new salespeople the job would be harder than they thought. They missed in the first 90 days but stayed because they believed in the problem. Admit what you do not know. When Alex took over a service department he had never worked in, he told its leaders they knew it better and asked them to own the fixes. The room changed once their opinions counted. If you are a contractor business owner and you want to make more money, work less, and win at home, we built something for you. Get the free Owner Time Audit at gatheringthekings.com/timeaudit. It is a simple worksheet that shows you where your week really goes. We email it to you as a PDF within minutes. Connect with Chaz Wolfe (Host): Website Facebook Instagram LinkedIn YouTube Connect With Alex Kraft: Website: https://www.heave.co/ LinkedIn: https://www.linkedin.com/in/alex-kraft-531408146/ Company LinkedIn: https://www.linkedin.com/company/heaveapp/ Instagram: https://www.instagram.com/heaveapp Facebook: https://www.facebook.com/Heave.co/ Medium: https://heaveapp.medium.com/ Support the show Like what you heard? Share this episode with a friend and leave us a review on Apple Podcasts or Spotify! Join the conversation by visiting GatheringTheKings.com and apply to connect with other high-performing entrepreneurs and their families.
- Transcript
- Chapters
#433
Thursday · 50 min
Health Insurance Is Not Healthcare | Harlon Pickett
Connect With Chaz Harlon Pickett got laid off after 19 years in corporate America. When his severance benefits ran out, agents quoted his family of four $800 a month, so he got licensed to sell himself insurance. That accident put him in the insurance business in 2007. Harlon now runs Eagle Care Health Solutions and builds custom health plans for businesses and individuals. He explains why hospitals keep hundreds of prices for the same procedure and why a hospital can have five billing people for every bed. He takes no money from insurance companies and is paid only by the employer. In this conversation with Chaz Wolfe, Harlon shows you why health insurance and healthcare are two different things and how to take back control of one of the largest lines on your P&L. KEY TAKEAWAYS Own your health plan decisions. Once you pass 50 employees the law requires you to offer insurance, and it becomes your second or third largest P&L item. Do not leave that strategy to HR. Question the renewal win. A broker who talks a 15% increase down to 12% still handed you a 12% increase. Ask for the cash price. Hospitals keep hundreds of prices for the same procedure. The cash price is often far lower, and the care is the same. Look at Direct Primary Care. Members pay about $50 to $120 a month, see their doctor at no added cost and can text the doctor directly. Know who pays your broker. A traditional broker is paid by the insurance company and other vendors. Harlon is one of fewer than 500 advisors in the country paid only by the employer. Name a healthcare champion. Harlon only works with companies that assign one person to track how the plan runs. Problems get fixed during the year, not after renewal. If you are a contractor business owner and you want to make more money, work less, and win at home, we built something for you. Get the free Owner Time Audit at gatheringthekings.com/timeaudit. It is a simple worksheet that shows you where your week really goes. We email it to you as a PDF within minutes. Connect with Chaz Wolfe (Host): Website Facebook Instagram LinkedIn YouTube Connect With Harlon Pickett: Website: https://eaglecarehealth.com/ LinkedIn: https://www.linkedin.com/in/harlon-pickett/ Facebook: https://www.facebook.com/eaglecarehealthsolutions Instagram: https://www.instagram.com/eaglecarehealthsolutions/ The Health and Wealth Power Hour: https://www.youtube.com/playlist?list=PLQRIXJqN-5oK0b-n-wE0mOus2t25NtoH5 Support the show Like what you heard? Share this episode with a friend and leave us a review on Apple Podcasts or Spotify! Join the conversation by visiting GatheringTheKings.com and apply to connect with other high-performing entrepreneurs and their families.
- Transcript
- Chapters
#434
Wednesday · 41 min
Why a $100K Launch That Paid Zero Was Worth It | Larry Kaul
Connect With Chaz Larry Kaul once sat in his office at 10 o'clock at night, overwhelmed by the P and L, after his most important salesperson quit and a product line dropped his company. He stopped trying to force a fix, and the answers came fast. Years later, a product launch he expected to put $100,000 in the bank paid nothing, and his fear of criticism went away. Larry's sales outsourcing company has been passive income for about three and a half years, with someone else running it. He also founded Red Pill Pathway, an eight week program for entrepreneurs who want freedom, satisfaction, and happiness without compromise. In this conversation with Chaz Wolfe, Larry shows you how to stop copying other people and build a business around how you work. KEY TAKEAWAYS Copy yourself, not someone else. Larry tells clients to learn how business works and then find their own way through it. Ask yourself what you want, then listen. Larry says the answer comes in a moment of silence, not while you force a solution. Challenge your beliefs. Larry defines a belief as something someone told you that you accepted as true without examining it. Build the business around how you like to work. If you want to be in the trenches with people, use technology to leverage your time and price for enough margin. Learn how your answers reach you. Larry names five channels: thought, feeling, heart, visualization, and creative objects. Spend time alone every day. Pick a time and a place, cut the distractions, and ask yourself what you want. If you are a contractor business owner and you want to make more money, work less, and win at home, we built something for you. Get the free Owner Time Audit at gatheringthekings.com/timeaudit. It is a simple worksheet that shows you where your week really goes. We email it to you as a PDF within minutes. Connect with Chaz Wolfe (Host): Website Facebook Instagram LinkedIn YouTube Connect With Larry Kaul: Website: https://www.redpillpathway.com/events LinkedIn: https://www.linkedin.com/in/larrykaul/ YouTube: https://www.youtube.com/@entrepreneurexperiment Facebook: https://www.facebook.com/larrykaul/ Instagram: https://www.instagram.com/larrykaul/ Support the show Like what you heard? Share this episode with a friend and leave us a review on Apple Podcasts or Spotify! Join the conversation by visiting GatheringTheKings.com and apply to connect with other high-performing entrepreneurs and their families.
- Transcript
- Chapters
#435
Tuesday · 44 min
His Partner Died With No Key Person Insurance | Robert Poole
Connect With Chaz In 2017 Robert Poole found his business partner of many years slumped over his computer. He had died of a heart attack the day before. Their key person insurance had lapsed, and Robert had no way to buy out the estate of a company valued at millions. Robert is a West Point graduate and Army veteran who runs Total Business Results, a B2B marketing firm built on cold calling. He stopped counting at 15,000 cold calls and figures he has made several hundred thousand. In a survey of his clients, 72% said they did not use social media in their business at all. In this conversation with Chaz Wolfe, Robert explains why cold calling still works in B2B, how to act when you are afraid, and why your business only grows as far as you do. KEY TAKEAWAYS Keep key person insurance in force if you have a partner. Robert and his partner let their term policies lapse so they could get in better shape first. They never got new policies, so Robert had no way to buy out the estate. Put your buy sell agreement in writing now. Robert wrote a two page agreement himself two years before his partner died. It required a business valuation, which gave him a way forward with the heirs. Do not assume your buyers live on social media. 72% of Robert's surveyed clients said they did not use it in their business. Owners often pick up the phone when the receptionist is out. Treat outreach as a duty. Someone out there needs your service right now. If you do not call them, a company with worse work and worse ethics will. Do the thing you fear. Robert says the only way to get rid of fear is to act. It gets easier the second time and easier every time after that. Lead people who choose to work for you. Robert ran his company top down like the military for years. Learning to hire, fire and build culture over the last 6 to 8 years paid him the most. If you are a contractor business owner and you want to make more money, work less, and win at home, we built something for you. Get the free Owner Time Audit at gatheringthekings.com/timeaudit. It is a simple worksheet that shows you where your week really goes. We email it to you as a PDF within minutes. Connect with Chaz Wolfe (Host): Website Facebook Instagram LinkedIn YouTube Connect With Robert Poole: Website: https://www.totalbusinessresults.com/ LinkedIn: https://www.linkedin.com/in/therobertpoole/ Instagram: https://www.instagram.com/therobertpoole/ YouTube: https://www.youtube.com/@therobertpoole Facebook: https://www.facebook.com/therobertpoole Support the show Like what you heard? Share this episode with a friend and leave us a review on Apple Podcasts or Spotify! Join the conversation by visiting GatheringTheKings.com and apply to connect with other high-performing entrepreneurs and their families.
- Transcript
- Chapters
#436
Monday · 30 min
Delegate the Task You Love Most First | Mike Michalowicz
Connect With Chaz Mike Michalowicz built and sold tech companies, including one to a Fortune 500 company, then lost everything out of what he calls arrogance and ignorance. He started writing down why he was failing, tested what worked in his own businesses and with other owners, and turned it into Profit First and All In. Mike found that only 17 percent of people will ever own a business, and only about 20 percent of those are still sustainable after five years. That is about 3 percent of the population. He learned from a Container Store co-founder that paying one A player $15 an hour beats paying three B players $10 an hour each. In this conversation with Chaz Wolfe, Mike shows you how to hire, delegate and lead so your team takes ownership of the outcome with you. KEY TAKEAWAYS Create jobs instead of doing the work. Mike says the owner's job is to be a creator of jobs. Most people want a good job at a good company, and only about 3 percent of people run a healthy, sustainable business. Match talent to tasks, not titles. Break every title into tasks. A receptionist who is weak at greeting walk-ins may be your best number cruncher. Delegate the task you enjoy most first. Write down everything you do, then hand off the easiest task you love. Mike started with his own scheduling, and now his wife books date night through his scheduler. Hire through workshops, not only interviews. Sports, an industry Mike puts at over $500 billion, recruits through camps instead of interviews. Home Depot runs bird house workshops and invites the most eager people to apply. Watch for thirst. Mike says potential shows up in three stages: curiosity, desire and thirst. Hire the people who reach thirst, where the work becomes part of who they are. Build community before culture. Mike's team rewrote one of his values into "be the Ted Lasso of companies." Let your values come from the whole team, not from the leader alone. If you are a contractor business owner and you want to make more money, work less, and win at home, we built something for you. Get the free Owner Time Audit at gatheringthekings.com/timeaudit. It is a simple worksheet that shows you where your week really goes. We email it to you as a PDF within minutes. Connect with Chaz Wolfe (Host): Website Facebook Instagram LinkedIn YouTube Connect With Mike Michalowicz: Website: https://mikemotorbike.com/ LinkedIn: https://www.linkedin.com/in/mikemichalowicz/ Instagram: https://www.instagram.com/mikemichalowicz/ YouTube: https://www.youtube.com/user/MikeMichalowicz Facebook: https://www.facebook.com/MikeMichalowiczFanPage/ 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.
- Transcript
- Chapters
#437
November 1 · 51 min
From a 1962 Sewing Machine to 2,000 Stores | Katie Richardson
Connect With Chaz Katie Richardson was a young mother making baby gear on her mom's 1962 Bernina sewing machine while her kids napped. A boutique owner asked to sell it and told her she would regret it if she did not use her gifts. Katie felt that future regret so strongly that it pushed her to start a business she knew nothing about. She launched her product in 2010 and within a year it was in 2,000 US stores with distribution in 26 countries. Over seven years she grew it into a multimillion dollar international company with about 30 products, then exited. Today she runs a business coaching company, works less than 20 hours a week and makes more money than she ever did. In this conversation with Chaz Wolfe, Katie shows you how to align your thoughts, feelings and actions so you can make hard decisions and build a business that fits your family. KEY TAKEAWAYS Use future regret as fuel. Walk your current path five years forward and look back. If you feel regret, those five years have not happened yet and you can change course now. Build daily practices. Katie exercises, journals, prays, reads scripture and keeps a weekly date night with her husband. Those habits let her work clear and fast. Stop waiting for the perfect decision. Katie stayed stuck for almost two years on a choice that affected her family, team and clients. She learned the skill is choosing, not choosing perfectly. Watch the words you use about yourself. Lines like "I'm always late" or "I'm tired today" shape how you show up. Decide who you are first and your results follow. Give your kids real responsibility. Her boys packed their own backpacks for a move to Taiwan at ages three, five and seven. Her chore chart gives identities like Chief Dog Officer and Duke of Dish Land. Define what matters before success shows up. Money, fame and recognition pulled at Katie when her business took off. A clear North Star kept her growth from costing her family. If you are a contractor business owner and you want to make more money, work less, and win at home, we built something for you. Get the free Owner Time Audit at gatheringthekings.com/timeaudit. It is a simple worksheet that shows you where your week really goes. We email it to you as a PDF within minutes. Connect with Chaz Wolfe (Host): Website Facebook Instagram LinkedIn YouTube Connect With Katie Richardson: Instagram: https://www.instagram.com/katie.live/ Linktree: https://linktr.ee/katie.live 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.
- Transcript
- Chapters
#438
October 31 · 41 min
Seven Figures at 25, Then Six Doses of Narcan | Joe Rivera
Connect With Chaz At 25, Joe Rivera was a stockbroker in New York making seven figures a year, and it still was not enough. A coworker handed him his first opiate, and his life went dark. He overdosed twice, and the last time it took six doses of Narcan to bring him back. After he got sober, Joe built another multimillion dollar company. Something was still missing, so he built a coaching and speaking business that helps owners who hit a wall of exhaustion and lack direction. In this conversation with Chaz Wolfe, Joe shows you how clarity, accountability, and asking for help move you from busy to productive. KEY TAKEAWAYS Get clear on your mission. Without clarity, Joe says life becomes unmanageable and things fall apart at the seams. Stop confusing busy with productive. Doing things with no direction is unproductive, even when your calendar is full. Face the fear head on. Joe could not picture life without drugs until he faced that fear and asked for help. Do not try to do it by yourself. You are only as good as your team, and people will help when you ask. Get around people who are ahead of you. Joe found sober people to get sober and multimillionaires to build his second multimillion dollar business. Pick an accountability partner. Without one, Joe says it is easy to get sidetracked and put off what you learned. If you are a contractor business owner and you want to make more money, work less, and win at home, we built something for you. Get the free Owner Time Audit at gatheringthekings.com/timeaudit. It is a simple worksheet that shows you where your week really goes. We email it to you as a PDF within minutes. Connect with Chaz Wolfe (Host): Website Facebook Instagram LinkedIn YouTube Connect With Joe Rivera: Website: https://www.withjoerivera.com/keynote-speaker Facebook: https://www.facebook.com/withJoeRivera Instagram: https://www.instagram.com/withjoerivera/ LinkedIn: https://www.linkedin.com/in/joe-rivera-0a27b311b/ YouTube: https://www.youtube.com/@reforgeacademywithjoeriver6288 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.
- Transcript
- Chapters
#439
October 30 · 49 min
Clients Made $5M Per Event. He Charged $2,000 | Michael Tucker
Connect With Chaz Michael Tucker was a part-time restaurant server and youth minister when a friend offered to teach him real estate. He had no money, so he traded marketing work for coaching. He ignored his mentor once and lost $20,000, but he kept going. His marketing work grew that mentor's real estate education company to $750,000 in 10 months with no list and no audience. Michael now runs The Funnel Pros, a done for you virtual event agency. He says clients have made up to $5 million per event, while he started out charging $1,500 to $2,000. In this conversation with Chaz Wolfe, Michael explains how to borrow other people's audiences, why you should hire before you burn out, and why you should charge for the result you deliver. KEY TAKEAWAYS Stick with one thing long enough to get good. Michael jumped between stock trading and drop shipping for three or four months at a time. Real estate worked because he kept working it. Hire before you burn out. Michael waited a year to make his first hire even though he had the money and the work months earlier. Email and client onboarding alone took him 10 hours a week. Know your numbers before you say you cannot afford help. One eight figure owner found $5,000 to $10,000 a month in software nobody used. A GTK member found about $600,000 a year in repeat job site purchases filed as miscellaneous. Build your SOPs before your first hire. Write the handbooks and processes now. When the hire comes, you just pass the baton. Borrow audiences from people who already have your customers. Michael's mentor ran 20 to 30 partner events over four years and made well over seven figures. A contractor could partner with a real estate agent or an insurance company. Charge for the result, not the hours. Michael stayed at $1,500 to $2,000 per event too long. Do not let other people set your value. If you are a contractor business owner and you want to make more money, work less, and win at home, we built something for you. Get the free Owner Time Audit at gatheringthekings.com/timeaudit. It is a simple worksheet that shows you where your week really goes. We email it to you as a PDF within minutes. Connect with Chaz Wolfe (Host): Website Facebook Instagram LinkedIn YouTube Connect With Michael Tucker: Website: https://www.thefunnelpros.com/ Facebook: https://www.facebook.com/funnelpros/ LinkedIn: https://www.linkedin.com/in/theofficialmichaeltucker/ Instagram: https://www.instagram.com/officialmichaeltucker/ 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.
- Transcript
- Chapters
#440
October 29 · 48 min
The 3 Reasons You Are Broke and the Path to $300K a Year | Brad Lea
Connect With Chaz Brad Lea dropped out of high school at 16 and grew up in a blue collar family that told him to get a real job. He stumbled into sales, started out earning everyone around him, and went on to build many businesses. He says if you are broke, there are only three reasons: your mindset, your skillset or your habits. Brad says if you make $90,000 a year, you can make $200,000, and the path starts with selling something you believe in. If your business already does $1M in revenue, he says you beat 92 percent of businesses, and tweaking a few levers can turn $200,000 of profit into $400,000. People pay him $6,000 for an hour of his opinion, and most of them already had the same answer. In this conversation with Chaz Wolfe, Brad explains how you use gratitude, sales and relationships to grow your income without sacrificing your family. KEY TAKEAWAYS Talk to more people. Brad says the more hands you shake, the more money you make. A salesperson earning $80,000 from 100 customers can talk to 200 and expect $160,000 or more. Find which of the three is broken. Brad traces every money problem to mindset, skillset or habits. A positive mindset with bad habits still fails, and a strong mindset with strong habits can win with average skill. Do more, get better, then scale. Increase your volume first, then study sales, closing and persuasion. When you are maxed out, scale by leveraging people and technology. Keep more of what you already make. At $1M in revenue you have proven the model. Brad says tweaking a few levers can double profit from $200,000 to $400,000 and help you grow faster. Protect the relationship before the dollar. Brad says every dollar you receive comes from a relationship. If you chase the money and damage the relationship, the money goes with it. Trust your own opinion. Brad would tell his younger self to read 10 to 20 pages of a self help book every day and stop worrying about what people think unless you pay them for it. If you are a contractor business owner and you want to make more money, work less, and win at home, we built something for you. Get the free Owner Time Audit at gatheringthekings.com/timeaudit. It is a simple worksheet that shows you where your week really goes. We email it to you as a PDF within minutes. Connect with Chaz Wolfe (Host): Website Facebook Instagram LinkedIn YouTube Connect With Brad Lea: Website: https://bradlea.com/ YouTube: https://www.youtube.com/vtbradlea Facebook: https://www.facebook.com/TheRealBradLea Instagram: https://www.instagram.com/therealbradlea/ LinkedIn: https://www.linkedin.com/in/bradlea/ TikTok: https://www.tiktok.com/@therealrealbradlea?lang=en 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.
- Transcript
- Chapters
#441
October 28 · 47 min
60 Units, $10K a Month, and About 10 Hours a Week | Jason Velie
Connect With Chaz Jason Velie started in real estate at about 30, while he still worked in finance. His first rental went badly. A bad inspection and a contractor who took $16,000 left the house sitting empty for about two years before it broke even. His first flip went much better and proved the model. He kept flipping and used the profits as down payments on apartment buildings. Today he holds about 60 units across four properties, clears more than $10,000 a month in net passive income, and works about 8 to 12 hours a week. He left his day job in April 2023. In this conversation with Chaz Wolfe, Jason talks about honest deals, an abundance mindset, and building wealth so you can be generous. KEY TAKEAWAYS Deal honestly, even when a lowball would pay more. A clear, fair offer builds the reputation that brings you the next deal. There is plenty of opportunity. Jason does not hoard what he knows or treat other investors as enemies. Give freely. He works every day to be able to be generous on every occasion. Get experienced help early. Vet your inspectors and contractors. Cheap help cost him dearly on his first rental. Use flips to fund the long game. Short term profits became down payments on assets that pay every month. Build the safety net first. Once passive income covers your living costs, you can make every other decision from strength. If you are a contractor business owner and you want to make more money, work less, and win at home, we built something for you. Get the free Owner Time Audit at gatheringthekings.com/timeaudit. It is a simple worksheet that shows you where your week really goes. We email it to you as a PDF within minutes. Connect with Chaz Wolfe (Host): Website Facebook Instagram LinkedIn YouTube Connect With Jason Velie: Instagram: https://www.instagram.com/jasonvelie 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.
- Transcript
- Chapters
#442
October 27 · 49 min
She Sold Her Business to Bill Gates. Build Yours to Sell | Beate Chelette
Connect With Chaz Beate Chelette built a business and sold it to Bill Gates. Today she calls herself The Growth Architect. She helps owners turn their talent into a business, add the systems that make it run, and build it so someone would want to buy it. She sees a lot of owners do the opposite. They buy course after course and tool after tool, chasing the next marketing promise, without ever building the business model underneath. In this conversation with Chaz Wolfe, Beate explains how to stop chasing tactics and start building a company with real value. KEY TAKEAWAYS Decide the end game early. A business built to sell for $50 million is set up differently from one built for $1 million. Write clear job descriptions. Roles that mix unrelated duties, like HR and sales, create overloaded mini me jobs that nobody can do well. Know what your skills are worth. Compare what your talent could earn with what you earn today, then decide what you want. Build the model before you buy the tools. Courses, funnels, and software do not fix a missing business model. Use a proven blueprint and a peer group. Learning from people who have done it is faster than figuring it out alone. What got you here will not get you there. Question the stories you tell yourself about what is possible. If you are a contractor business owner and you want to make more money, work less, and win at home, we built something for you. Get the free Owner Time Audit at gatheringthekings.com/timeaudit. It is a simple worksheet that shows you where your week really goes. We email it to you as a PDF within minutes. Connect with Chaz Wolfe (Host): Website Facebook Instagram LinkedIn YouTube Connect With Beate Chelette: Website: https://beatechelette.com/ LinkedIn: https://www.linkedin.com/in/beatechelette/ Instagram: https://www.instagram.com/beatechelette/ 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.
- Transcript
- Chapters
#443
October 26 · 49 min
If You Can't Justify a Premium Price, You're Doing It Wrong | Colin Sanburg
Connect With Chaz Colin Sanburg went to work in a family owned manufacturing company at 21. He ended up running it as CEO for almost 15 years and led a turnaround that took about 10 of them. He later started an industrial distribution company and still owns both. Along the way he noticed something. Most owners take their financial advice from their banker or their CPA. Neither one is focused on making the business more profitable. So Colin built FinElevate to sit in the finance seat with owners and run a profit playbook every week. In this conversation with Chaz Wolfe, Colin explains how an owner can understand the numbers well enough to lead with them. KEY TAKEAWAYS Pick one unit everyone understands. Jobs completed, cleanings done, seats filled. When sales, operations, and finance use the same unit, everyone speaks the same language. Start with two or three numbers. Add more only after your team understands the first ones. Charge a premium and earn it. Low prices still require full service. Colin says if you cannot justify premium pricing, you are doing it wrong. Read your P&L as percentages. Track each cost as a share of revenue, like labor at 30 percent or less. Know your fixed and variable costs. If revenue doubles and fixed costs stay flat, profit jumps. Run the what ifs. Delegate the work, not the understanding. You do not have to be the accountant. You do have to know the story well enough to hold your advisors accountable. If you are a contractor business owner and you want to make more money, work less, and win at home, we built something for you. Get the free Owner Time Audit at gatheringthekings.com/timeaudit. It is a simple worksheet that shows you where your week really goes. We email it to you as a PDF within minutes. Connect with Chaz Wolfe (Host): Website Facebook Instagram LinkedIn YouTube Connect With Colin Sanburg: Website: https://finelevate.com/ LinkedIn: https://www.linkedin.com/in/colinsanburg/ Instagram: https://www.instagram.com/the.finelevate/ 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.
- Transcript
- Chapters
#444
October 25 · 47 min
Three People Running a Hundred AI Agents | Alexander De Ridder
Connect With Chaz Alexander De Ridder builds AI agents for a living. His company, SmythOS, lets teams create agents with drag and drop tools and no code. His picture of the future is a small team of three people running a hundred agents that do the repetitive work. That sounds far away for a lot of owners. Alexander says it is closer than most think, and the companies that stay lean and learn early will have a big cost advantage over the ones that wait. In this conversation with Chaz Wolfe, he explains what AI agents are, where to start, and how to keep people in control. KEY TAKEAWAYS Start now with the basics. Use the free versions of common AI tools on your own work before you spend money on anything bigger. Do not mow your lawn with a bazooka. Keep AI on a short leash. Approve each step and keep a person responsible for every decision. Train a few people. Pick one to four people on your team to learn how to build and run agents. Lean companies win. A competitor with much lower costs can make a slow company irrelevant. Get ready for AI customers. More people will use AI assistants to find and buy services. Make sure your business can be found and understood. Humans multiplied. Alexander says it is not human versus machine. It is people doing more with machines. If you are a contractor business owner and you want to make more money, work less, and win at home, we built something for you. Get the free Owner Time Audit at gatheringthekings.com/timeaudit. It is a simple worksheet that shows you where your week really goes. We email it to you as a PDF within minutes. Connect with Chaz Wolfe (Host): Website Facebook Instagram LinkedIn YouTube Connect With Alexander De Ridder: LinkedIn: https://www.linkedin.com/in/adridder/ 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.
- Transcript
- Chapters
#445
October 24 · 1 hr
She Left Nike Weeks Before the Pandemic. Here's How She Survived | Dr. Taryn Marie Stejskal
Connect With Chaz Dr. Taryn Marie Stejskal led executive leadership development at Nike and global leadership development at Cigna. In February 2020 she left Nike to start her own company. She had bookings lined up to replace her income. She was a single mom with two young sons. Within weeks the pandemic wiped those bookings out. She ran her business on a 30 day cash runway for 36 months, with no outside money. Today she leads the Resilience Leadership Institute and wrote the bestselling book The Five Practices of Highly Resilient People. In this conversation with Chaz Wolfe, Taryn breaks down what resilience really is and how an owner can build more of it. KEY TAKEAWAYS Resilience means coming out better. Taryn defines it as facing challenge, change, and complexity and coming out enhanced, not diminished. Do not try to go back. She says we do not return to who we were before a hard season. We bounce forward. Know when to push and when to pivot. Productive perseverance means you stay the course or change it on purpose. Leading can be lonely. Even owners surrounded by people carry decision fatigue. Connection with yourself and with others is part of the fix. Audit your self talk. Listen to your own words for 24 hours. Replace have to with get to. Fear is information. Notice it, but do not let it make your decisions. If you are a contractor business owner and you want to make more money, work less, and win at home, we built something for you. Get the free Owner Time Audit at gatheringthekings.com/timeaudit. It is a simple worksheet that shows you where your week really goes. We email it to you as a PDF within minutes. Connect with Chaz Wolfe (Host): Website Facebook Instagram LinkedIn YouTube Connect With Dr. Taryn Marie Stejskal: Website: https://www.resilience-leadership.com/ Instagram: https://www.instagram.com/drtarynmarie/ LinkedIn: https://www.linkedin.com/in/taryn-marie-stejskal/ 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.
- Transcript
- Chapters
#446
October 23 · 31 min
The One Habit Keeping Successful Men Stuck at 70% | Clifford Stephan
Connect With Chaz Clifford Stephan spent 20 years building a compensation consulting firm in Silicon Valley. He was successful, social, and a regular drinker since high school. In his late thirties he started to feel like he was aging faster than he should. He spent real money on sleep, supplements, and diets. None of it fixed the problem. Then he took a full year off alcohol. That one decision changed his sleep, his energy, and his health. At 50 he was surfing 10 foot waves in Nicaragua. He turned the experience into Booze Vacation, a coaching program that helps high achieving men take a long break from drinking and see what they are really capable of. In this conversation with Chaz Wolfe, Clifford explains why he believes a lot of successful men are running at 60 to 70 percent, and why alcohol is often the reason. KEY TAKEAWAYS Moderate drinking still has a cost. Clifford says even a few drinks a week can hurt sleep, hormones, mood, focus, and recovery. One decision beats a hundred small ones. A long break replaces the daily question of whether to drink tonight. Clifford calls it trading one decision for a hundred. Play offense, not defense. A short dry month is defense. A three, six, or 12 month break gives your body and brain time to show you the difference. The first few weeks are the hardest. After that the focus moves to sleep, exercise, personal growth, and rebuilding a social life that does not depend on alcohol. Muscle is your currency for longevity. In your 40s and 50s, strength training matters more than most supplements. Ask if it serves you. Chaz has never had a drink. His test is simple. If my success is up to me, why would I take in something that takes away my control? If you are a contractor business owner and you want to make more money, work less, and win at home, we built something for you. Get the free Owner Time Audit at gatheringthekings.com/timeaudit. It is a simple worksheet that shows you where your week really goes. We email it to you as a PDF within minutes. Connect with Chaz Wolfe (Host): Website Facebook Instagram LinkedIn YouTube Connect With Clifford Stephan: Website: https://boozevacation.com/ Instagram: https://www.instagram.com/boozevacation/ Facebook: https://www.facebook.com/BoozeVacation/ 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.
- Transcript
- Chapters
#447
October 22 · 44 min
From $2,000 Land Deals to Four Businesses and Home for Dinner | Travis King
Connect With Chaz Travis King started a real estate side hustle with his wife while he still had a salaried job. The 2008 recession hit his house deals hard, so he switched to land. The deals were smaller and the risk was lower. Some early flips made only about $2,000 each. He kept going. His goal was $10,000 a month in recurring revenue. The side business passed his salary and he walked away from the job. Today he runs four connected businesses, each with a small remote team, and he built them so he could be home with his sons. In this conversation with Chaz Wolfe, Travis shares how focus and repetition turned a side hustle into a business that fits his family. KEY TAKEAWAYS Pick one thing and stay with it. Travis says almost anything will work if you commit to it for 12 to 18 months instead of switching after a few. Mastery comes through frequency. Lots of small, low risk deals built his skill and his confidence. After 20 to 40 deals, he knew what he was doing. Set a number you can measure. His target of $10,000 a month gave the side hustle a finish line. Courage is not the absence of fear. The successful people Travis knows still feel fear. They move anyway. Learn from someone who has done it. A mentor gets you there faster than any shortcut. Win at home first. If your kids do not think you were a great dad, Travis asks, who cares what else you built? If you are a contractor business owner and you want to make more money, work less, and win at home, we built something for you. Get the free Owner Time Audit at gatheringthekings.com/timeaudit. It is a simple worksheet that shows you where your week really goes. We email it to you as a PDF within minutes. Connect with Chaz Wolfe (Host): Website Facebook Instagram LinkedIn YouTube Connect With Travis King: Website: https://travisking.com/ Facebook: https://www.facebook.com/landeducator/ Instagram: https://www.instagram.com/_travisaking/ 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.
- Transcript
- Chapters
#448
October 21 · 35 min
Disney, Harley Davidson and NASA Hired Him to Automate Their Work | Phillip Brown
Connect With Chaz Phillip Brown has spent about 20 years automating how businesses run. His firm, Blu Pitt, has built systems for Walt Disney, Harley Davidson, and NASA. He also works with small companies that have 5 to 15 people. His view is simple. The average business uses 50 to 100 different software tools every week. About 80 percent of the back office work can be automated. Most owners just have not written down what they do. In this conversation with Chaz Wolfe, Phillip explains how an owner can get hours back every week without being a programmer. KEY TAKEAWAYS Write it down first. If a task only lives in your head, nobody else can do it and no tool can automate it. Turn your daily and weekly work into simple playbooks. Start with the work you dread. Email sorting, payment checks, and bookkeeping repeat every week. Those hours add up fast. Connect what you already have. You may not need a new all in one platform. Getting your current tools to talk to each other often matters more. Ship it, then fix it. Early in his career Phillip saw most software projects die before launch. Release something small, get feedback, and improve it. Check before you build. Someone may already sell a tool that solves your problem better and cheaper. Give AI clear instructions. Phillip says to think of a computer as a child with a fresh mind. Tell it exactly what you want in plain language. If you are a contractor business owner and you want to make more money, work less, and win at home, we built something for you. Get the free Owner Time Audit at gatheringthekings.com/timeaudit. It is a simple worksheet that shows you where your week really goes. We email it to you as a PDF within minutes. Connect with Chaz Wolfe (Host): Website Facebook Instagram LinkedIn YouTube Connect With Phillip Brown: Website: https://www.blupitt.com/home LinkedIn: https://www.linkedin.com/in/phillipjbrown/ 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.
- Transcript
- Chapters
#449
October 19 · 48 min
He Didn't Start Playing Until 14. Then He Went Pro for 10 Years | Dre Baldwin
Connect With Chaz Dre Baldwin did not start playing basketball until he was 14. He played one year of high school ball, mostly from the bench. He walked on at a Division III school, a level that almost never sends anyone to the pros. After college he sold gym memberships and worked at Foot Locker. Then he paid his own way into an exposure camp in the summer of 2005, played well, signed with an agent, and was playing pro ball in Lithuania a few weeks later. He played professionally for almost 10 years. Today Dre runs Work On Your Game. He has written 11 books, spoken at TEDx four times, and built more than 48 million views on YouTube. In this conversation with Chaz Wolfe, he breaks down the mental toughness behind all of it, and how a business owner can use the same playbook. KEY TAKEAWAYS Quitting and pivoting are not the same thing. Dre walked away from baseball because he did not have the talent. He kept the goal and changed the vehicle. Owners do the same when a service line or a market stops working. If it is not working, your formula may be wrong. When a business stalls, Dre says the strategy itself may be off. Find someone who already has the right information and learn from them. Review your habits like employees. Every habit gets a review. Keep it, adjust it, or let it go. Work backward from the goal. Dre calls it a reverse roadmap. Start with the result, then decide what has to be true at each step to get there. Moderation is average. Dre says there is no neutral in life. You are either getting better or getting worse. Clear yes or no rules make hard decisions easy. Invest in yourself early. His advice to his younger self is to start investing in himself as soon as possible, in what he learns and in who he spends time with. If you are a contractor business owner and you want to make more money, work less, and win at home, we built something for you. Get the free Owner Time Audit at gatheringthekings.com/timeaudit. It is a simple worksheet that shows you where your week really goes. We email it to you as a PDF within minutes. Connect with Chaz Wolfe (Host): Website Facebook Instagram LinkedIn YouTube Connect With Dre Baldwin: Website: https://dreallday.com Support the show Like what you heard? Share this episode with a friend and leave us a review on Apple Podcasts or Spotify! Join the conversation by visiting GatheringTheKings.com and apply to connect with other high-performing entrepreneurs and their families.
- Transcript
- Chapters
#450
October 14 · 59 min
I Treated My Team Wrong for 10 Years as CEO | James Lawrence
Connect With Chaz James Lawrence met with more than 500 CEOs and found the biggest companies had the worst people problems. If you lead a team and still make every call yourself, this episode shows you what that costs. James Lawrence was a CEO for 20+ years, mostly in automotive, and admits he made every mistake in the book in his first 10 years as a leader. Today he runs Happy, a platform that uses behavioral science and AI to coach each employee on how to work with the specific people around them, right before the meeting happens. You will hear how Vince Lombardi and Andy Reid led individuals instead of a roster, the 60-second walk that changed how James handles anger, and the backyard exercise that pointed him to the work he does now. Key Takeaways When a leader makes every decision because he does not trust his team, he wastes the people he is paying. Not everyone sees the world like you. A quiet, analytical person in a meeting is listening, not rejecting you. Vince Lombardi said he had 50 men on his team and treated them as 50 unique people. Know when to push in public and when to talk in private. When emotion spikes, take a 60-second walk around the building. James did it so often his team wondered where he went, and it changed how he responds. Engaged teams are more profitable, more productive and keep people longer. Treating culture as an extra is a mistake. Take a blank pad, set money aside, and write what you want from the rest of your life. James spent three to four hours at a time on it, over about three months. James writes the number of days he likely has left at the top of his to-do list every day. Nothing has made him value his time more. Chapters 00:00 Meet James Lawrence, CEO of Happy 02:38 Why Leaders End Up Making Every Call 06:25 What 500 CEOs Revealed About People 09:56 How the Happy Assessment Works 17:07 AI Coaching Before Your Next Meeting 20:28 Adapting to Others Without Faking It 25:50 Vince Lombardi Treated 50 Men Differently 29:52 Travis Kelce, Andy Reid and Psychological Safety 33:57 Every Mistake in His First 10 Years 37:30 Teaching Self-Awareness to Your Kids 39:45 Engaged People Are Not a Vitamin 44:54 The Blank Pad of Paper Exercise 49:56 Counting the Days He Has Left 54:03 Do the Work You Love Every Day 56:51 How to Connect With James Lawrence Make More Money. Work Less. Win At Home. If you're 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 Get the free Owner Time Audit at gatheringthekings.com/timeaudit. It is a simple worksheet that shows you where your week really goes. We email it to you as a PDF within minutes. Connect with Chaz Wolfe (Host): Website Facebook Instagram LinkedIn YouTube 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.
- Transcript
- Chapters

Showing 1–20 of 26 episodes