Wealthyist

Core Theme: How a middle-class Wisconsin upbringing, strong family values, and an athlete’s mindset of consistent small improvements shaped Steve Novak’s approach to money, lifestyle, and giving back — and kept him far away from the “broke ex-athlete” stereotype.

Key Takeaways from the Conversation:

  1. Grounded Upbringing as the Anchor
    • Grew up in Brown Deer, WI (middle/lower-middle class); dad was a teacher/coach, mom a nurse. 
    • Saw bigger houses and nicer cars as a kid → early motivation that real wealth required success without debt. 
    • Even after making NBA money, never felt the need for a mansion. Bought a normal house in Whitefish Bay (“looks like all the other houses”) and still lives a relatively modest lifestyle.
  2. Financial Philosophy = Athletic Mindset
    • Translated his shooting training mantra (“get 0.1% better every day”) into investing. 
    • Very conservative investor: prioritizes steady compounding over home-run bets or crypto. 
    • Learned the hard way with a few bad private deals/restaurants → “losing money felt worse than winning felt good.” 
    • Focus: never move backward; small, consistent forward progress compounds over a 50+ year post-basketball timeline.
  3. Lifestyle Choices
    • Played on 9 teams, lived in Houston, LA, NY, Toronto, etc. → realized Milwaukee/SE Wisconsin is one of the most underrated places to live and raise a family. 
    • Chose walkable, community-oriented neighborhoods (Whitefish Bay) over sprawling estates. 
    • Family now owns two homes in Wisconsin (North Shore + Lake Country) instead of the typical athlete Florida/Arizona second home — “Wisconsin summers are the best in the world.”
  4. Giving Back & Full-Circle Moment
    • Dad coached generations of kids → Steve now runs shooting clinics all over SE Wisconsin, passing on the “aha” moments he had after thousands of hours in the gym. 
    • Wants the next generation to say, “Steve taught me footwork and motivated me.”
  5. NBA Financial Realities & Lessons
    • Rookie paycheck shock, royalty checks with no withholding, surprise tax bills when income jumps, jock taxes, escrow, etc. 
    • NBA’s unusually generous 401(k) match (up to 150%) and bridge annuities show the league/NBPA actively try to protect players. 
    • Mandatory financial-literacy meetings ($10k fine if you skip) — education is there, but players still have to act on it.
  6. Current Life
    • Just hired as Walt “Clyde” Frazier’s backup Knicks broadcaster (full-circle: New York was where he played his best ball). 
    • Still lives in Milwaukee; kids cheer for both the Bucks and Knicks.
Bottom Line (in Steve’s words):
“Don’t try to hit home runs. Just keep the money you worked hard for moving 0.1% in the right direction every day, make it last a long time, and don’t end up on a ‘broke’ documentary.”
A refreshingly grounded, Midwestern take on wealth from someone who’s seen both the NBA flash and the long-term reality — and consciously chose the latter.

What is Wealthyist?

Wealthyist, the podcast that discusses the lifestyles, choices, and strategies of the wealthy. Each week, the Annex Private Client team talks to experts in a variety of areas to discuss trends and paths visited by people who have built or are in the process of building significant wealth.