Matt Caruso, Founder, Caruso Insights

 
Matt is a market professional known for his unshakable optimism, disciplined execution, and deep knowledge of growth investing. He gained national attention for his 346% return in the 2020 U.S. Investing Championship.

Matt’s background as a market maker and former finance professor allows him to bridge the gap between theory and action. His work has been featured in Fox Business, Investor’s Business Daily, and Business Insider. 

John Pocorobba, Founder, RainKing Insights

John is an active growth stock investor with over 20 years of market experience. He founded Rain King Insights with his professional mindset to educate traders, both full and part time, to capture more success in the markets.  John is exceptional at helping investors visualize trading concepts, turning ideas into clear, repeatable actions. He is currently transitioning his leadership of Boston IBD Meetup into his new Quarterly Connect Series to launching in January 2026.

Mike Webster, Senior Market Strategist at Investor’s Business Daily (IBD)

A 30-year market veteran and current Senior Market Strategist at Investor’s Business Daily (IBD). Mike is a former portfolio manager at William O’Neil & Co., where he developed a stock grading system to prioritize high-probability setups.

Known for using the 21-day exponential moving average as a trend filter, Mike’s session will help traders understand their risk, their setups, and themselves.

Jason Shapiro, Hedge Fund Manager 

A hedge fund manager with a contrarian edge, Jason is best known for being featured in Jack Schwager’s Market Wizards. His success comes from fading crowded trades and speculator sentiment using the Crowded Market Report (CMR) — a data-driven system he developed and still uses today.

With over two decades of experience across equities, currencies, futures, and metals, he brings a rare perspective few traders get access to.