Hi Playmakers,
When I was a broke kid in a tiny town of 2,000 people, with a blind dad and a mom working as a cashier, I couldn’t picture what my life would look like today. I didn’t see a path to venture capital, or bestselling books, or building companies from scratch. I just knew I wanted more freedom, opportunity, and choices.
I had never been around people with money growing up, so I had to figure out how all of this worked on my own. Over time, I sought out people who had built extraordinary wealth and learned how they thought about money. Their lessons that completely changed my life.
Here are three of the biggest ones, and how I applied them:
Wealth is a mindset, not a number. They don’t measure success by what they can spend, but by how much freedom their money buys them.
For me, that meant redefining how I saw my time. I started measuring the value of my labor at home and chose to hire help (like a housekeeper or landscapers) instead of spending hours doing that work myself. Buying back my time gave me more freedom to focus on the things that mattered most.Cash flow matters more than net worth. They focus on building assets that generate income, not just assets that look good on paper.
Instead of upgrading my 2012 Mazda3 with 180,000 miles on it, I bought rental properties. For years, my tenants were driving fancier cars than me, but I was focused on building assets that worked for me while I slept.Money is a tool, not an identity. They use it intentionally to create opportunities, invest in ideas, and design a life on their terms.
One of my billionaire friends once told me he was embarrassed when he was introduced as a “newbie billionaire” to Laurene Powell Jobs, the wife of Steve Jobs. That moment stuck with me. No matter how far you climb, there’s always someone higher up the ladder. And that’s why financial freedom has to be defined by you. It’ll look different for everyone. For me, I work toward a goal that allows me to pursue meaningful work, spend time with people I love, and chase my biggest dreams without comparing my journey to others.
Those lessons reshaped the way I thought about money and gave me the freedom to take big risks.
If you’ve ever wondered whether stories like this are still possible, let me tell you: they are.
Simply ask yourself the same question I did, over and over again:
Why not me?
The Play of the Week: Carol Tomé, CEO of UPS
Before she took the helm at UPS, Carol B. Tomé had retired. She was confident she had done all she needed to after an 18-year tenure as CFO at The Home Depot, where she helped scale the business from 400 to 2,200 stores and nearly $100 billion in annual revenue. Then the pandemic hit.
UPS needed a steady, experienced leader. At age 63, Carol returned to the boardroom as CEO of the $135 billion logistics giant. In that moment, her leadership became a global lifeline.
Carol B. Tomé was born in Jackson, Wyoming in January 1957, as Carol Louise Buchenroth. Raised hunting, fishing, and sewing her own clothes, she learned from a young age resilience, self-reliance, and discipline. These were attributes that served her in business as well as in the outdoors.
Her father was a community banker, and Carol lent in her early days at the same bank in Denver. She went on to leadership roles at Johns-Manville and Riverwood International before The Home Depot recruited her in 1995 to lead its expansion into Mexico. By 2001, she was CFO. During her tenure, Home Depot not only weathered the 2008 financial crisis but also saw its share price rise over 450 percent and revenue approach $100 billion.
In 2019, she walked away to retire. Family, ranch, board work, philanthropy, and hobbies awaited. She thought her story had ended.
The Execution Plan: Your Play for the Week
Insights are only valuable if they’re acted on. Let’s turn this knowledge into impact with small but powerful action steps.
This week’s challenge: reflect on your relationship with money.
For some of us, this might be one the hardest challenges yet. Think about one area where your relationship with money needs to improve. Are you spending too much on things you don’t need? Is there credit card interest that’s eating into potential savings? Do you have an emergency fund? It looks different for everyone, but one of the best places to start is to reflect on your financial situation with honesty and humility.
Call to Action:
1️⃣ Reflect on one area where you can improve your financial mindset.
2️⃣ Report back and let me know how it went! Drop a comment or share your post below. The best responses may be featured next week.
Playmaker’s Spotlight: Real People, Real Wins
This week’s play comes from Lucy Guo, co-founder of ScaleAI.
This may, in fact, be the most savage money-saving tip I’ve ever heard. I truly don’t think this can be topped. WDYT?
PS: If you were as fascinated as me, my full deep dive on Lucy can be found here.
Want to be featured next?
Make sure to tag @Jenny Stojkovic on your post for a chance to be featured.
The Extra Edge: Industry & Success Trends
📱 Shocking absolutely no one, a smartphone ban in Dutch schools has improved learning. At least we have a study to prove it.
📖 A man who read 3,500 books has the definitive list. Take a look.
🧔🏻♂️ Male birth control. It’s almost here. They tested it on humans, and it’s safe & effective.
🦻🏻 Gene therapy allows baby girl to hear her mother’s voice for the first time. Science is remarkable.
On this day in 2003, this old "lady" was discontinued...
How to Get Involved:
The Wednesday Play isn’t just a newsletter — it’s a community. I’ll be announcing much more in coming weeks and months! For now, let’s connect across social.
