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How Bart Oates Built 3 Careers and Achieved Financial Freedom
In a world where relying on a single income source feels increasingly risky, how can you build multiple careers without burning out?
This episode dives into the strategic and financial realities of career diversification—a proven path to financial freedom that most people never pursue. While working full-time in the NFL, Bart Oates attended law school every off-season, ultimately graduating magna cum laude. He didn't wait for his playing career to end before building his next income stream.
We're joined by 3-time Super Bowl champion Bart Oates, who brings a unique perspective as both an elite athlete and successful entrepreneur. From going undrafted to winning championships, from earning his law degree while playing professionally to building purpose-driven businesses post-retirement, Bart's journey challenges everything we think we know about "having time" to pursue our goals.
Together with host Spencer Pascal, we move beyond the typical athlete success story to examine the practical strategies behind building sustainable income streams, transitioning careers successfully, and creating financial independence that outlasts your primary career.
- The Reality of Building Multiple Income Streams While Working Full-Time
- The "Show Up" Philosophy That Compounds Wealth
- Mental Toughness for Entrepreneurs & Business Builders
- Career Transition Strategy: From Athlete to Lawyer to Entrepreneur
- Principles vs. Preferences: A Decision-Making Framework
- The Undrafted Mindset: Turning Rejection Into Championship Results
- Building Purpose-Driven Income That Lasts
- Income Diversification in Real Time
If you're stuck in the 9-5 grind wondering "what else is possible," if you're building a side hustle but struggle with consistency, or if you're considering a career pivot but think it's "too late"—this episode is for you.
Bart Steven Oates is a 3-time Super Bowl champion (XXI, XXV, XXIX), 5-time Pro Bowl selection, and magna cum laude law graduate who earned his degree while playing professional football. He went from undrafted free agent to NFL legend, then successfully transitioned into law and entrepreneurship. Today, he helps former NFL players navigate the concussion settlement program, combining his playing experience with legal expertise to serve those who need it most.
Career Timeline:
- Accounting Degree, BYU (Marriott School of Business)
- 2× USFL Champion (Philadelphia/Baltimore Stars)
- NFL: New York Giants (1985-1993), San Francisco 49ers (1994-1995)
- Law Degree, Seton Hall University (earned during off-seasons), Magna Cum Laude
- Former President, NFL Alumni Association (NY-NJ Chapter)
"You show up. They show up. I play the game. I show up. I practice. I show up. I go to law school. It was really hard, but you just show up."
"I could have just shrunk up and melted away, or I could buckle up and say, I'm gonna make this as hard and impossible for him to make a change."
"There's principles and there's preferences. Principles—honesty, integrity—you never compromise. Preferences? Most things in life are preferences. Don't make them issues."
"Is it really worth starting an argument over a light when there are people out there who don't have a wife to wake up next to?"
Bart's Current Work:
- NFL Concussion Settlement Program - Helping former players (1970s-2014) navigate neurological damage claims including Alzheimer's and Parkinson's
Organizations:
- NFL Alumni Association (NY-NJ Chapter)
- Philadelphia/Baltimore Stars (USFL)
- New York Giants
- San Francisco 49ers
Want more conversations with leaders who've built financial freedom through diverse income streams?
Subscribe to Cash Flow Corner:
🎙️ Apple Podcasts | Spotify | YouTube | Your Favorite Platform
Connect with Spencer:
📱 Instagram: @spencerpascal
If you like this episode ✅ Tag @spencerpascal on Instagram with your biggest takeaway
Who This Episode Is For
✓ 9-to-5 professionals feeling trapped and wanting to build additional income streams
✓ Side hustlers struggling with consistency while working full-time
✓ Career changers wondering if it's too late to learn new skills
✓ Entrepreneurs facing rejection and needing mental toughness strategies
✓ Business owners wasting energy on conflicts that don't matter
✓ Anyone who thinks "I don't have time" to pursue their goals
View all episodes
By Spencer PascalIn a world where relying on a single income source feels increasingly risky, how can you build multiple careers without burning out?
This episode dives into the strategic and financial realities of career diversification—a proven path to financial freedom that most people never pursue. While working full-time in the NFL, Bart Oates attended law school every off-season, ultimately graduating magna cum laude. He didn't wait for his playing career to end before building his next income stream.
We're joined by 3-time Super Bowl champion Bart Oates, who brings a unique perspective as both an elite athlete and successful entrepreneur. From going undrafted to winning championships, from earning his law degree while playing professionally to building purpose-driven businesses post-retirement, Bart's journey challenges everything we think we know about "having time" to pursue our goals.
Together with host Spencer Pascal, we move beyond the typical athlete success story to examine the practical strategies behind building sustainable income streams, transitioning careers successfully, and creating financial independence that outlasts your primary career.
- The Reality of Building Multiple Income Streams While Working Full-Time
- The "Show Up" Philosophy That Compounds Wealth
- Mental Toughness for Entrepreneurs & Business Builders
- Career Transition Strategy: From Athlete to Lawyer to Entrepreneur
- Principles vs. Preferences: A Decision-Making Framework
- The Undrafted Mindset: Turning Rejection Into Championship Results
- Building Purpose-Driven Income That Lasts
- Income Diversification in Real Time
If you're stuck in the 9-5 grind wondering "what else is possible," if you're building a side hustle but struggle with consistency, or if you're considering a career pivot but think it's "too late"—this episode is for you.
Bart Steven Oates is a 3-time Super Bowl champion (XXI, XXV, XXIX), 5-time Pro Bowl selection, and magna cum laude law graduate who earned his degree while playing professional football. He went from undrafted free agent to NFL legend, then successfully transitioned into law and entrepreneurship. Today, he helps former NFL players navigate the concussion settlement program, combining his playing experience with legal expertise to serve those who need it most.
Career Timeline:
- Accounting Degree, BYU (Marriott School of Business)
- 2× USFL Champion (Philadelphia/Baltimore Stars)
- NFL: New York Giants (1985-1993), San Francisco 49ers (1994-1995)
- Law Degree, Seton Hall University (earned during off-seasons), Magna Cum Laude
- Former President, NFL Alumni Association (NY-NJ Chapter)
"You show up. They show up. I play the game. I show up. I practice. I show up. I go to law school. It was really hard, but you just show up."
"I could have just shrunk up and melted away, or I could buckle up and say, I'm gonna make this as hard and impossible for him to make a change."
"There's principles and there's preferences. Principles—honesty, integrity—you never compromise. Preferences? Most things in life are preferences. Don't make them issues."
"Is it really worth starting an argument over a light when there are people out there who don't have a wife to wake up next to?"
Bart's Current Work:
- NFL Concussion Settlement Program - Helping former players (1970s-2014) navigate neurological damage claims including Alzheimer's and Parkinson's
Organizations:
- NFL Alumni Association (NY-NJ Chapter)
- Philadelphia/Baltimore Stars (USFL)
- New York Giants
- San Francisco 49ers
Want more conversations with leaders who've built financial freedom through diverse income streams?
Subscribe to Cash Flow Corner:
🎙️ Apple Podcasts | Spotify | YouTube | Your Favorite Platform
Connect with Spencer:
📱 Instagram: @spencerpascal
If you like this episode ✅ Tag @spencerpascal on Instagram with your biggest takeaway
Who This Episode Is For
✓ 9-to-5 professionals feeling trapped and wanting to build additional income streams
✓ Side hustlers struggling with consistency while working full-time
✓ Career changers wondering if it's too late to learn new skills
✓ Entrepreneurs facing rejection and needing mental toughness strategies
✓ Business owners wasting energy on conflicts that don't matter
✓ Anyone who thinks "I don't have time" to pursue their goals