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Caruso Insights
Rain King Insights
Back at Pier Sixty-Six

Elevate
Conference 2026

Market Leadership • Risk Management • Execution
October 15–17, 2026 Fort Lauderdale, Florida
For serious traders and investors focused on process, performance, and market leadership

Join us back at Pier Sixty-Six for three days of market strategy, execution insight, and real-world trade management with traders who live this process every day.

Why Attend

Real market substance in a destination setting

This weekend is designed for traders and investors who want thoughtful market discussion, practical takeaways, and meaningful conversations — all in a setting that feels elevated, relaxed, and worth traveling for.
📈

Serious market conversations

Focused discussion around process, execution, risk, and market behavior for active traders and investors.

🤝

Meaningful networking

Meet like-minded members, hosts, and guest speakers in a more personal conference environment.

🌴

Back at Pier Sixty-Six

Return to one of South Florida’s most iconic waterfront settings for a conference experience that feels elevated from start to finish.

Trading Focus

What this conference is really about

This is not a generic event built around broad inspiration. It is built for people who care about the market, process, decision-making, and hearing from serious participants.

Built for traders and investors who want:

A more thoughtful conversation about markets, beyond surface-level commentary.
Clearer perspective on execution, process, and navigating real market conditions.
Direct access to hosts and guest speakers with different but complementary viewpoints.
An environment where the conversations off stage are just as valuable as the sessions themselves.
Pass Options

Choose the conference experience that fits you best

Both passes include full access to the core conference experience, with VIP designed for attendees who want the most exclusive access of the weekend.
VIP tier for Elevate Conference 2026 is limited. If you want the most access and the most complete weekend experience, VIP is the tier for you.
Featured Tier Limited VIP Seating

VIP Pass

The most complete conference experience, including premium small-group access beyond the main event.
Regular Pricing: $3,499
$2,999
USD
Early Bird Offer
Limited Time Only
  • ✓ Exclusive small-group VIP dinner on Friday, October 16
  • ✓ Exclusive VIP afternoon session on Saturday, October 17
  • ✓ Welcome cocktail
  • ✓ Light breakfast on both days
  • ✓ Lunch on both days
  • ✓ Printed conference manual
Secure VIP Pass
VIP is limited and expected to be the first tier to fill.
Core Conference Access

Executive Pass

Full access to the main conference experience for attendees focused on the core event.
Regular Pricing: $1,999
$1,899
USD
Early Bird Offer
Limited Time Only
  • ✓ Welcome cocktail
  • ✓ Light breakfast on both days
  • ✓ Lunch on both days
  • ✓ Printed conference manual
  • ✓ Access to main conference sessions
Get Executive Pass
A strong option for attendees who want the full main-stage experience.
Hotel Room Block: We also have a very limited hotel room block at an exclusive rate of $369 per night, which is a meaningful discount from regular hotel rates. There is also no resort fee, which makes a real difference versus most hotels in the area. Once you register, just reach out to us and we will send over the next steps for booking.
Hosts & Speakers

Learn directly from experienced market professionals

Elevate Conference 2026 brings together respected traders, investors, and educators for a weekend built around process, execution, market insight, and real conversation.
Hosts
Matt Caruso
Host

Matt Caruso

Matt Caruso is a market professional known for blending real-world trading experience with clear teaching. A former market maker and former finance professor, he has also been featured in financial media including FOX Business and Investor’s Business Daily.

Market Strategy Growth Stocks Risk Management
John Pocorobba
Host

John Pocorobba

John Pocorobba leads Rain King Insights and has over 20 years of market experience as an active individual growth stock investor. He is the leader of the Boston IBD Meetup and founder of the Annual BlueSky Investing Conference, with a teaching style built around helping investors visualize concepts and improve execution.

Position Trading Swing Timeframes Market Visualization
Guest Speakers
Tom Basso
Guest Speaker

Tom Basso

Tom Basso is a veteran trader, educator, and author known to many through the Market Wizards series. He currently runs EnjoyTheRide.world, where he shares trading education and market wisdom built from decades of experience.

System Trading Trader Psychology Long-Term Process
Christian Flanders
Guest Speaker

Christian Flanders

Christian Flanders is an independent trader focused on super performance in the stock market. He finished second in the U.S. Investing Championship in 2024 with a +433% return, and followed that with another second-place finish in 2025 with a +167% return.

Super Performance Growth Stocks Execution
Final Agenda

Three days of market insight, strategy, and connection

October 15–17, 2026 at Pier Sixty-Six in Fort Lauderdale, Florida.
All times Eastern
Live market analysis, actionable trading sessions, guest speakers, and exclusive VIP experiences
Thursday · October 15, 2026

Welcome Day

3:00–5:00 PM
Pre-Conference Sessions & Registration
2026 Year in Review with John and Matt
Current Leadership with John and Matt
5:30–7:30 PM
Welcome Social Hour
Friday · October 16, 2026

Conference Day One

Light breakfast and lunch included
8:00 AM
Light Breakfast
8:30 AM
Welcome
Matt Caruso and John Pocorobba
8:45 AM
Trading the Market Open LIVE
Morning pre- and post-open process with Matt Caruso
10:15 AM
Break · 15 Minutes
10:30 AM
Capitalizing on Explosive Gaps
John Pocorobba
12:00 PM
Lunch Break · 60 Minutes
1:00 PM
Special Guest
Psychology of Position Size
Christian Flanders
2:30 PM
Effective Watchlist Building
Using screeners and ranking systems with Matt Caruso
3:30 PM
Break · 15 Minutes
3:45 PM
Special Guest · Zoom
Building a Trading System
Tom Basso
5:00 PM
Day One Wrap-Up
6:30 PM
VIP Experience
Yacht Cocktails & Dinner
An exclusive evening with the hosts, guest speakers, and fellow VIP attendees
Saturday · October 17, 2026

Conference Day Two

Light breakfast and lunch included
8:00 AM
Light Breakfast
8:30 AM
Welcome Back
8:45 AM
Timing Market Bottoms with Options and Positioning
Matt Caruso
10:15 AM
Break · 15 Minutes
10:30 AM
YOU as the Edge
John Pocorobba
12:00 PM
Lunch Break · 60 Minutes
1:00 PM
Combining Strategies to Navigate Market Conditions and Reduce Portfolio Volatility
Matt Caruso
2:15 PM
Bull Market Super Cycle
John Pocorobba
3:15 PM
Break · 15 Minutes
3:30 PM
VIP Session
Market Wizard Tom Basso
My All-Weather Journey in the Markets
Q&A with all speakers
Featuring Christian Flanders
5:00 PM
Final Wrap-Up
The Elevate VIP Experience

An unforgettable evening on the water

We have officially confirmed the VIP dinner experience for Elevate Conference 2026 — an exclusive private yacht evening created for a limited number of VIP attendees.

Private yacht for the Elevate Conference VIP dinner Exclusive VIP Yacht Experience
Outdoor sky deck aboard the private yacht
Private yacht dining area
Yacht lounge and social space
VIP Dinner — Friday Evening

More than a dinner. A private yacht experience.

VIP attendees will board directly from the Pier Sixty-Six marina before setting out for an evening cruise along the Fort Lauderdale Intracoastal Waterway.

From the moment you step aboard, the evening is designed to feel polished, relaxed, and personal. Enjoy welcome drinks, waterfront views, a curated dining experience, music, and conversation while cruising past Fort Lauderdale’s luxury homes, mega-yachts, and palm-lined canals.

With hosts, speakers, and fellow VIP attendees together in a much smaller setting, this will be one of the most memorable and exclusive parts of the Elevate weekend.

01
Board directly from Pier Sixty-Six A seamless waterfront departure directly from the conference hotel and marina.
02
Cruise the Intracoastal Waterway Take in waterfront estates, mega-yachts, palm-lined canals, and iconic Fort Lauderdale scenery.
03
Curated dining and cocktails Enjoy an elevated dining experience with attentive service in a relaxed onboard setting.
04
A more personal evening Spend meaningful time with hosts, speakers, and a select group of serious market participants.
VIP seating is strictly limited. The yacht has limited capacity. Once the available VIP passes are filled, additional seats cannot be added.
Attendee Feedback

See what last year’s attendees had to say

Stay on property at Pier Sixty-Six
Stay at Pier Sixty-Six

Make the weekend feel like more than just a conference

Returning to Pier Sixty-Six means returning to a setting that already felt right for the event — elegant, coastal, and unmistakably South Florida.

We also have a very limited hotel room block at an exclusive rate of $369 per night, which is a meaningful discount from regular hotel rates. There is also no resort fee, which makes a real difference versus most hotels in the area.

Once you register, just reach out to us and we will send over the next steps for booking. Staying on property helps attendees get more out of the experience, from early conversations and relaxed networking to evening events and the overall flow of the weekend.

Very limited room block
$369/night exclusive rate
No resort fee
Booking steps sent after registration
Explore the Venue