JJ Kinahan is the CEO of IG North America, overseeing Tastytrade, Tastycrypto, and Tasty Live, and is a veteran of over 30 years in the financial markets. From his early days shoveling snow for neighbors in Chicago to trading options on the bustling floor of the CBOE, JJ brings real-world experience and a deep understanding of market cycles, entrepreneurship, and the shifting investing landscape.

On this episode we talk about:

JJ’s journey from a fourth-grade snow-shoveling hustler in Chicago to CEO and respected financial educator

Lessons from his immigrant family upbringing, navigating a blue-collar path to college (thanks to baseball) and seizing an unplanned opportunity that redirected his career into trading

The value of saying “yes” to new experiences—especially early in your career—and why breaking into offices, showing up, and staying open are career-changing moves

Why the status and stigma against the trades is fading, with skilled labor now highly respected and compensated (“plumbers charge like lawyers—as they should!”)

The evolution of JJ’s career: from summer clerk at the options exchange to running trading operations and eventually leading Tastytrade and Tastycrypto

Tasty Live’s mission of financial education: daily free live content empowering retail investors with practical, actionable trading and risk management education

JJ’s active investing toolbox: stocks, options, futures, forex, crypto, real estate, and small business investing, plus the importance of “tuition” (learning cheaply when you’re new)

Step-by-step practicals: how non-professionals can use conservative options strategies like covered calls and puts to enhance returns on stocks they already own

The real way to build wealth: small habits over a long time; why “get rich quick” always ends badly, and the importance of financial discipline

Why starting small, managing risk, and knowing your downside before you act are the keys to surviving—and eventually thriving—as an investor

Top 3 Takeaways

Seize Opportunity and Say “Yes” Early: Careers—in trading or elsewhere—are built by showing up, embracing new experiences, and being available when opportunity knocks.

Discipline and Risk Management are Everything: Start small, define your worst-case scenario, and don’t let emotions (or others’ hype) dictate your investments.

Wealth is Built Slowly, Not Speculatively: There are no shortcuts. Learn, automate good habits, and put your money to work without betting the farm.

Notable Quotes

“People will pay you for things they don’t want to do themselves.”

“If somebody cracks the door, just beat it down and keep going until somebody tells you to stop.”

“If anyone’s telling you there’s an instant way to make money—run. There’s always risk and reward.”

“Financial discipline is not a game—risk not thy whole lot!”

Connect with JJ Kinahan:

Free financial markets education: TastyLive.com

Brokerage and trading platform: Tastytrade.com

Disclosure: Options involve risk and are not suitable for all investors as the special risks inherent to options trading may expose investors to potentially significant losses. Please read Characteristics and Risks of Standardized Options at tastytrade.com/disclosures before deciding to invest in options.

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