Episode 69: The Weekly Stock Move That Prints Cash | Jaden Sterling
November 26, 2025
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Former Wall Street pro turned wealth mentor Jaden Sterling joins Bo to break down one of the biggest beliefs holding people back from financial freedom. After a decade on Wall Street and building a 125 unit real estate portfolio with 12.5 million in capital, Jaden realized his real purpose was not just to grow his own wealth, but to teach everyday people how to do it too.
In this episode, Jaden explains why it does not actually take money to make money. It takes vision, the right vehicle, and the courage to think beyond traditional 401(k)s and mutual funds. From covered calls that can generate weekly income to using self directed IRAs and affordable housing to build serious wealth, Jaden shows how regular people can start small and still play a big game.
Guest Resources
Website: sterlingstockpicker.com
Instagram: @jadensterling
Value Bombs
It Takes Vision, Not Money – Why the belief that you need a lot of cash to start is one of the most limiting money myths.
Start With What You Know – How investing in companies you already use and love can be the simplest way to begin.
Covered Calls For Cash Flow – How Jaden uses covered calls to target 1.5 to 2 percent per week and stack returns on top of stock gains.
Beyond 401(k)s – Why he likes rolling old 401(k)s into self directed Roth IRAs and using them more creatively.
Affordable Housing Advantage – How he used creative financing, city partnerships, and apartment buildings to build an eight figure portfolio.
Sponsors
Grit Fitness – Elevate your fitness with cutting edge training and expert coaching. Learn more at Grit Fitness.
D3 Capital – Unlock sophisticated investment strategies designed to protect and grow your wealth. Learn more at D3 Capital.
Show Notes
[00:00] – Meet Jaden Sterling and hear his journey from Wall Street in the 90s to building a 125 unit real estate portfolio.
[02:00] – How Sterling Stock Picker was born and why he built a tool for novice investors to invest like experts.
[04:00] – Rethinking returns and why he trains people to aim for a minimum 30 percent instead of being satisfied with 8 to 10 percent.
[06:00] – What covered calls are, how they work, and why they can generate consistent weekly income.
[08:00] – Breaking down a simple covered call example and why options do not have to be “too risky” when used correctly.
[10:00] – The problem with parking everything in 401(k)s and mutual funds and why management fees quietly eat your returns.
[13:00] – Using Roth and self directed IRAs to invest in stocks, options, and even real estate more strategically.
[16:00] – The story of buying an apartment building using his IRA as collateral and getting it released after forcing equity.
[19:00] – How a chance meeting with the head of affordable housing led to grants, special financing, and multiple deals with the city.
[22:00] – Why he believes it does not take money to make money and how vision plus the right partners can change everything.
[26:00] – Bo’s experience going down the rabbit hole with Sterling Stock Picker, Robinhood, and automated trading platforms.
[30:00] – How Jaden’s AI assistant Finley helps users research companies, understand metrics, and learn investing faster.
[34:00] – Teaching his kids to invest early and how his daughter’s Aritzia stock and his son’s Apple position helped pay for college.
[38:00] – The importance of focusing on one niche at a time, whether it is affordable housing or a specific stock strategy.
[42:00] – Jaden’s plans for adding trading into the platform, using options more, and building recurring income for users.
[46:00] – Wrapping up with where to find Jaden online and how Sterling Stock Picker can help first time and experienced investors.
Killer Resources
D3 Capital eBook – Master tax reduction strategies with our exclusive guide.
Grit Fitness Blog – Premium content on fitness, wellness, and peak performance.
D3 Capital Blog – Stay ahead with insights on financial trends and advanced wealth building strategies.
Performance & Wellness Picks
Slate Protein – High quality, convenient daily protein.
Ghost Hydration – Stay energized and hydrated throughout your day.
Integrative Therapeutics – Wellness essentials for optimized health.
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