Driven To Win
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 systemsSell and market with disciplineBuild a team that runs without youCreate and protect wealthLead your family with the same intent you bring to your companyChaz built and scaled companies in franchising, home services, real estate, and online education, and became a...
Why He Gave 90% of His Building Company to Charity | Jeff Rutt
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In 2007 a banker slid a file across the table and told Jeff Rutt to pay back the loans on 25 model homes in 25 communities within 60 days. About half the home builders in the country did not survive 2007 to 2010. Jeff did, because he had kept a one to one debt to equity ratio.
Jeff bought a dairy farm at 20, then moved into home building with 12 pre-sold homes in his first year. Keystone Custom Homes now builds about 500 homes a year with about 150 employees. He also started Hope International, which has loaned about $1.6 billion with...
Why 4 Top MBAs Made His Inc. 500 Company Worse | George Kriza
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George Kriza grew his company onto the Inc. 500 with 473 percent growth over three years. To build a stronger leadership team, he hired three Northwestern MBAs, a University of Chicago MBA, and senior engineers from Motorola. It became the most strife filled, ineffective period in his company's history.
George learned to create clarity, pick the top three priorities, and align the team, pay, and communication behind them. He also put $2.3 million into an outsourced software fix he expected to cost under $1 million, fired the vendor, brought the work back in house, and built...
He Raised $325M, Then Five Key People Quit in One Day | Tim Calise
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Tim Calise grew his gym franchise business to eight locations, funded with a line of credit on his house. At 1:37 one Wednesday morning he lay awake thinking, if only everyone knew how screwed we are. The next day five of his main people quit.
Years earlier, Tim and a partner started a hedge fund with $750,000 committed and raised over $325 million in three and a half years. He later served as the number two at Gym Launch with Alex and Leila Hormozi, where a stake sold to a private equity firm for a...
150 SOPs and One Hire Bought Back His Time | Tyler Woodall
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Tyler Woodall built an insurance agency by dialing 150 businesses a day and walking into 30 more. Then he had to put down his dog of almost 15 years, and it made him reassess his whole life. He got rid of the business he did not love, ended a relationship that was not working, and six months later his life looked completely different.
To get himself out of the day-to-day, Tyler wrote out every task, recorded a Loom video for each one, and built 150 standard operating procedures. He hired one person, sent all 150 documents, and...
He Built a $50M Company, Then Got Fired | John St. Pierre
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John St. Pierre spent 15 years growing a sports business from about $10 million to more than $50 million in revenue. To chase $100 million he kept raising debt and investor money until his equity was diluted and he lost control. In 2018 the board fired him from the company he co-founded.
That failure led to the seven principles in his book, The $100 Million Journey. He applied them to another business and grew it to $100 million the right way. Today he is CEO and chairperson of Rhombus Group, a holding company with six businesses run by their...
Every Hire Should Triple Customer Experience | Holly Jean Jackson
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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.
<...The 2.5 Year Pivot Behind the Uber of Heavy Equipment | Alex Kraft
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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...
Health Insurance Is Not Healthcare | Harlon Pickett
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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...
Why a $100K Launch That Paid Zero Was Worth It | Larry Kaul
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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...
His Partner Died With No Key Person Insurance | Robert Poole
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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...
Delegate the Task You Love Most First | Mike Michalowicz
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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...
From a 1962 Sewing Machine to 2,000 Stores | Katie Richardson
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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...
Seven Figures at 25, Then Six Doses of Narcan | Joe Rivera
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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...
Clients Made $5M Per Event. He Charged $2,000 | Michael Tucker
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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...
The 3 Reasons You Are Broke and the Path to $300K a Year | Brad Lea
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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...
60 Units, $10K a Month, and About 10 Hours a Week | Jason Velie
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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...
She Sold Her Business to Bill Gates. Build Yours to Sell | Beate Chelette
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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...
If You Can't Justify a Premium Price, You're Doing It Wrong | Colin Sanburg
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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...
Three People Running a Hundred AI Agents | Alexander De Ridder
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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...
She Left Nike Weeks Before the Pandemic. Here's How She Survived | Dr. Taryn Marie Stejskal
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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...
The One Habit Keeping Successful Men Stuck at 70% | Clifford Stephan
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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...
From $2,000 Land Deals to Four Businesses and Home for Dinner | Travis King
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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...
Disney, Harley Davidson and NASA Hired Him to Automate Their Work | Phillip Brown
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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.
<...He Didn't Start Playing Until 14. Then He Went Pro for 10 Years | Dre Baldwin
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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...
I Treated My Team Wrong for 10 Years as CEO | James Lawrence
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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...
His Company Lost $7 Million on One Job | Ryan Schmitt
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Ryan Schmitt's company lost about $7 million on one job, and he now calls it his most impactful project.
If you run a contractor business and one bad job could sink you, this episode shows you how an owner walked back from the edge.
In 2018, Ryan's heavy civil firm in Jacksonville lost its bonding. He recapitalized the company, sold every asset with equity, and borrowed $2 million from a peer in his business group. He had chest pains and kept his key man life insurance because he was not sure...
From Miserable Engineer to 400 Real Estate Deals | Mike DeHaan
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Mike DeHaan quit engineering the same day he decided to, with no plan, and closed about 400 off-market real estate deals in three and a half years.
If you are using a passive income number as the reason you have not made your move, this episode is for you.
Mike spent five years as an engineer and was miserable for four and a half of them. He called his wife on the drive to work, quit that day, and went from low six figures to driving Uber and working...
Why Your Business Needs to Be on Video Now | Cam Beaudoin
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80% of video on social media is watched without sound.
If you are not captioning your videos, you are invisible to 8 out of 10 people scrolling past your content right now.
Cam Beaudoin spent years as an IBM developer and was always the one who wanted to present at demo day. He turned that into two businesses: a creative agency that helps professional speakers build real speaking businesses, and work that helps companies make their content accessible to more people.
In this conversation with Chaz Wolfe, you will...
How 2 Years in Federal Prison Built an 8-Figure Career | Sean Martin
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Sean Martin wrote the next 10 years of his life in composition notebooks from a prison cell and hit almost every target.
If you keep pulling yourself back to the same level no matter how hard you push, this episode is for you.
At 29, Sean was making 6 figures in medical sales and still hustling on the side. He served 2 years in prison. He stayed sober, read over 200 books, and rewrote his identity. Today he runs a seven, almost eight figure a year medical supply business built on relationships with...
She Started Over With $40 and Built Wealth | Janine Jennings
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Janine Jennings lost her infant daughter after a heart transplant, had no money left, and restarted her business with one $40 client.
If you own a business and you do not know your net worth or your retirement number, this episode is for you.
Janine is the president of JP Tax Service and Accounting and Cultural Differences Salon. She started as a hairstylist, took a free HR Block course to earn extra money in the slow winter months, and grew one phone call into a full tax firm. Her...
Heal Your Past So You Don't Repeat It at Home | Rick Jordan
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Rick Jordan's deal to take his company public fell apart eight times in the last five days before it closed.
If you run a service business and cash feels tight, his rule of thirds gives you a margin target you can check today.
Rick is the founder and CEO of Reach Out Technology, a public cybersecurity company with 78 employees. He went from the first Geek Squad agent in Chicago to buying companies, and he lived through survival mode when he was laid off right as his twins were...
He Asked Jim Rohn to Lunch. It Changed His Life | Dan Rawitch
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Jim Rohn told a room of college students that poor people should take rich people to lunch, and Dan Rawitch was the first person in all his years of speaking to actually ask him.
If you want to grow, take risks, and raise kids who can earn their own way, this conversation is for you.
Dan got rejected from twelve interviews at nineteen before someone hired him as a loan officer. He went on to trade bonds for Bear Stearns, built DataFacts into the fourth largest mortgage credit...
How He Lost $50K a Month in 5 Days and Fixed It | Armando LeDuc
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Armando LeDuc lost close to $50,000 a month in retainer business in about five days, and the fix became the client journey system he now builds for other companies.
If clients leave unhappy, invoices go unpaid, or referrals have dried up, this episode shows you where the gap is.
Armando is the director of LeDuc Entertainment and host of the Spaghetti on the Wall podcast. When his team started posting daily content for their own business, they hit $30,000 a month in revenue in the first month. Then clients started...
Fired, Broke, and Building From $0 | Neb Aynu
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Neb Aynu was the top producer at his bonding firm when he got let go. He started Kingdom Bonding with zero income, zero dollars, and zero relationships with insurance companies.
If you have ever felt stuck in a box and wondered what going all in really costs, this one is for you.
Neb had planned to start Kingdom Bonding in five years, at 35. Instead, he moved in with his sister, put his apartment on Airbnb, walked places in the rain, kept his budget under $100 a month, and worked 70...
If You Build It, They Will Not Come | Rylee Meek
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Rylee Meek sold about $30 million in insulation without knowing what the R in R value stands for.
If your business does not have a predictable flow of leads and sales, you have a very expensive hobby, and this episode shows you why.
Rylee gave his life to entrepreneurship at 15. He moved from network marketing to personal training to dinner seminar marketing, where he had his first million dollar year at 26. He has started eight companies and says each one hit seven or eight figures within the first 10 months...
Why You Lose Customers You Already Won | Clifton Muckenfuss
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Clifton Muckenfuss grew his construction company to 60 to 62% repeat and referral business while spending less than 1% of top-line revenue on direct response marketing.
If you finish a job and never talk to that customer again, you are losing your easiest sales.
Clifton co-founded a residential construction company in 2010 knowing nothing about construction, exited in 2021, and launched Building Raving Fans. He is now director of coaching at Win Rate Consulting. His Google reviews went from 3 in the first five or six years to over 100. He did it with a...
Passive Income From Raw Land | Mark Podolsky
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Mark Podolsky has done over 6,000 raw land deals and takes every July off to see how his team runs without him.
If you only make money when you are working, this episode shows you what a business that runs without you looks like.
Mark left investment banking, a 45-minute commute and a micromanaging boss after he started buying raw land at tax deed auctions for pennies on the dollar. He now runs a land business built on other people's time, software and automation, and other people's money, and...
Five Financial Steps From Broke to a Family Trust | Coach JV
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In 2020 Coach JV was broke on his parents' couch with two kids, and four years later he is coming up on three seven-figure ecosystems and has a Rockefeller Trust set up for his family.
If you want to build wealth that outlasts you and still be home for your kids, this episode is for you.
John Vasquez, known as Coach JV, left a banking VP role in 2017. The pandemic shut down the gym he built with Alex Hormozi's Gym Launch program, and he moved his family into his...
How Selling to a Holding Company Can Triple Your Exit | Josh Wilson
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Josh Wilson says an owner with $1 million in cash flow who sells to a holding company instead of the open market could walk away with $10 million instead of $3 million.
If you plan to sell your company one day, this episode shows you what buyers look for and how to get a bigger multiple.
Josh sold his first business, a wedding DJ company, for $25,000 at 19. He built a $25 million real estate portfolio over 15 years, then moved into acquisitions. He now runs six companies with over 156 employees in four states...
Remote Work Is Not the Problem. Your Culture Is | Chris Dyer
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Chris Dyer managed 4,500 employees and independent contractors and never laid off a single person, even through 2008 and 2009.
If your team underperforms and you think remote work or the new generation is the problem, this one is for you.
Chris ran PeopleG2, a human capital company, for 20 plus years and earned best places to work scores for about 15 years. Now he speaks and consults on culture, remote work, and leadership. His message: the reason remote work is not working in your business is your culture.
In this...
