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Connect With Chaz
Mark Podolsky spent years in investment banking with a 45-minute commute each way, buying things he did not care about to impress people who were not thinking about him. Then he started going to tax deed auctions on the side and buying raw undeveloped land for pennies on the dollar. He never looked back.
Today Mark has done over 6,000 land deals, takes the entire month of July off every year to stress-test his team, travels globally at will, and runs what he calls a passive income machine built on three things: other people's time, software and automation, and other people's money. In this conversation with Chaz Wolfe, Mark walks through his entire land investing model step by step, explains why defaults are not actually a problem, why raw land is the most boring and least competitive niche in real estate, and why the only real mistake is stopping deal flow when you get scared.
Key Takeaways:
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:
Visit www.gatheringthekings.com for information on how to apply.
Connect with Chaz Wolfe (Host):
Website
YouTube
Profit Starts with Better Books!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.
Connect With Chaz
In December 2006, John Vasquez attempted suicide. That is how he describes it. The person he was that day, a man drowning in opiate addiction and low self-worth, died. He considers it the beginning, not the end.
Fourteen years later, the COVID pandemic shut down the gym he had built using Alex Hormozi's Gym Launch program, and he found himself sleeping on his parents' couch with two kids, back in the house he grew up in, watching his parents' same patterns around money and fear play out in real time. That was the moment he drew a line in the sand.
Today Coach JV runs three seven-figure business ecosystems, has a Rockefeller Trust set up for his family for generations, and has built a massive social media following teaching financial literacy, micro and macroeconomics, and cryptocurrency education to people who were never taught any of it. In this conversation with Chaz Wolfe, Coach JV breaks down his 5-part financial framework, why Ray Dalio is the lens through which he reads the global economy, why paying yourself first is not just a strategy but a frequency shift, and how he is raising his kids to be the first generation to break the pattern for good.
Key Takeaways:
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:
Visit www.gatheringthekings.com for information on how to apply.
Connect with Chaz Wolfe (Host):
Website
YouTube
Profit Starts with Better Books!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.
Connect With Chaz
Josh Wilson started at seven years old on a cruise ship, charging his vacation friends a markup to use his grandfather's cruise card. He built a wedding DJ business at 16 and sold it at 19 for $25,000. His only W2 job was two months as a buggy boy at Winn Dixie before he got fired. Since then he has built a 25-million-dollar real estate portfolio, lost over a million dollars on a single investment, and pivoted to M&A where he is now acquiring his seventh company with a goal of 10 companies and 10 million in EBITDA before exiting to private equity.
In this conversation with Chaz Wolfe, Josh breaks down the entire M&A framework he uses: what to look for in a target company, why he only buys companies doing at least a million in cashflow, the five reasons a contractor business owner should consider selling to a holding company instead of selling on the open market, why most businesses have not raised prices since COVID, and how the multiple arbitrage game works when you roll your equity into a holding company instead of taking a 3x exit alone.
Key Takeaways:
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:
Visit www.gatheringthekings.com for information on how to apply.
Connect with Chaz Wolfe (Host):
Website
YouTube
Profit Starts with Better Books!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.
Connect With Chaz
Chris Dyer ran PeopleG2, a human capital company with 4,500 employees and thousands of clients. He managed that team through the 2008 financial crisis without a single layoff. He built a culture that earned best-places-to-work awards for 15 consecutive years. And when he finally stepped away from the CEO role, he described it as an elephant getting up off his chest.
Now he speaks and consults on culture, remote work, and leadership, and his message to business owners is direct: the reason remote work is not working in your business is not remote work. It is your culture.
In this conversation with Chaz Wolfe, Chris covers what actually separates leaders who make remote work a lightning bolt for their organization versus those who burn it down. He also breaks down why accountability and tough conversations are the foundation of any culture, how to stop micromanaging and start building top performers, and why the question every leader needs to ask themselves before any difficult conversation is not what do I think but do I want to be right or do I want to be effective.
Key Takeaways:
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:
Visit www.gatheringthekings.com for information on how to apply.
Connect with Chaz Wolfe (Host):
Website
YouTube
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.
Connect With Chaz
Professor Tonya M. Evans graduated from Howard University School of Law, clerked in the Third Circuit, practiced at major law firms in Philadelphia, and is now a full tenured professor at Penn State with a joint appointment in data sciences. She is also a former professional tennis player who played at Northwestern on scholarship, and she is one of the most credible voices in the country on the intersection of law, finance, and emerging technology.
Her message to business owners is simple and direct: the big banks are trying to scare you out of a space they are quietly moving into themselves. JP Morgan CEO Jamie Dimon still calls Bitcoin garbage. JP Morgan is an authorized participant in the Bitcoin ETF. BlackRock, the most conservative investment firm in the world, was first in line to issue a Bitcoin ETF. The little guy is being scared away while institutional money gets positioned.
In this conversation with Chaz Wolfe, Prof Tonya breaks down what blockchain actually is in plain language, the three biggest crypto myths holding business owners back, why it is not early but not late, and how to start thinking about Web3 as a business owner even if you never buy a single coin.
Key Takeaways:
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:
Visit www.gatheringthekings.com for information on how to apply.
Connect with Chaz Wolfe (Host):
Website
YouTube
Profit Starts with Better Books!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.
Connect With Chaz
Tony Lamb grew up watching his father sell vacuum cleaners door to door and thought that was the pinnacle. He got a college degree, walked into a pharmaceutical sales interview, heard the number $36,000 a year, and drove straight back to the vacuum cleaner office to ask for the highest commission they would pay.
Then one afternoon, his kids ran to a beat-up ice cream truck in their neighborhood, paid $22 for freezer-burned ice cream from a guy fresh out of prison, and Tony saw a gap. Two years of obsession later, he launched Kona Ice. Today Kona Ice is the largest food truck company in the world with over 1,700 units, has given back over $130 million to local communities, and spawned two additional brands. Tony did it with no debt, a clear lane, and a refusal to be anything other than the absolute best at what he does.
In this conversation with Chaz Wolfe, Tony breaks down the origin story of Kona Ice, the difference between a small business owner and an entrepreneur, why pain and suffering are the best growth tools available, and what it actually takes to build a franchise that scales without you.
Key Takeaways:
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:
Visit www.gatheringthekings.com for information on how to apply.
Connect with Chaz Wolfe (Host):
Website
YouTube
Profit Starts with Better Books!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.
Connect With Chaz
Scott Arias built ACE Consulting into an eight-figure commercial construction consulting company with 223 employees, over 3,000 client companies, and what he claims is a 100 percent A-player team. He overcame a devastating motorcycle accident and prescription drug addiction to do it. And he has done it by building something most contractors never build: a system for identifying, hiring, and leading people across three completely different generations simultaneously.
In this conversation with Chaz Wolfe, Scott breaks down why generations are defined by historical events, not arbitrary birth year ranges, what each generation actually needs to perform at the highest level, the specific interview questions he uses to filter for A players, and why the biggest mistake most Gen X and Boomer leaders make is assuming their generation had it right.
People problems are the number one drain on every contractor doing $1M+. This episode is the framework for fixing that.
Key Takeaways:
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:
Visit www.gatheringthekings.com for information on how to apply.
Connect with Chaz Wolfe (Host):
Website
YouTube
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.
Connect With Chaz
In January 2009, Jay Conner had two houses under contract and a banker who had just told him his line of credit was closed. No warning. No grace period. The global financial crisis had arrived and Jay was not prepared.
He asked himself one question: who do I know who can help me with this problem? Nine days later he had raised $2,150,000 in private money without asking a single person for it. Since then he has never asked anyone for money. He currently has $8.5 million in private money available and has completed over $52 million in real estate transactions across more than 500 homes rehabbed.
In this conversation with Chaz Wolfe, Jay breaks down his exact private money framework: the mindset shift that separates desperate fundraising from confident education, the two-conversation rule that eliminates awkwardness entirely, the good news phone call script that funds deals without pitching, and why there is more money available right now than most people will ever access because they are asking the wrong question the wrong way.
Key Takeaways:
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:
Visit www.gatheringthekings.com for information on how to apply.
Connect with Chaz Wolfe (Host):
Website
YouTube
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.
Connect With Chaz
Somewhere between 50 and 60 percent of Americans are actively considering a new job this year. There are 2.3 open jobs in the United States for every available worker to fill them. And more than 50 percent of new hires never show up for their first day because they accepted another offer in the window between signing and starting.
Joey Coleman has spent his career teaching companies like Zappos, Whirlpool, Hyatt, and NASA how to keep the people they spent months recruiting. His book Never Lose an Employee Again applies the same eight-phase framework he built for customer retention to the employee experience. In this conversation with Chaz Wolfe, Joey walks through every phase, identifies where even the biggest companies break down, and gives contractor business owners the exact moves to make before another great employee walks out the door.
Key Takeaways:
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:
Visit www.gatheringthekings.com for information on how to apply.
Connect with Chaz Wolfe (Host):
Website
YouTube
Vacation With Entrepreneurial FamiliesSupport 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.
Connect With Chaz
You close the deal. Your team is high-fiving. You are ready to deliver. Meanwhile, your new customer is sitting at home in an emotional hole, doubting the decision they just made, wondering if they chose the right company, and the only sound filling that doubt is their own voice.
That gap between when a customer buys and when you actually deliver is one of the most expensive moments in any contractor's business. Most companies never think about it. Joey Coleman has spent 20 years teaching companies like Zappos, Whirlpool, Hyatt, and NASA how to fix it.
In this conversation with Chaz Wolfe, Joey breaks down the six communication tools available to every business owner, all eight phases of the customer journey from first impression to raving advocate, and why most companies are only getting three or four of those phases right. This is Part 1. Part 2 applies the same framework to employee retention.
Key Takeaways:
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:
Visit www.gatheringthekings.com for information on how to apply.
Connect with Chaz Wolfe (Host):
Website
YouTube
Vacation With Entrepreneurial FamiliesSupport 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.
From the publisher's feed
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,…
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.