To The Moon

At the Tiger Brokers “Trade to Win” Season 4 meetup held in Singapore in March 2025, three top-ranked contestants — @Sean , @EliteEquity, and @Caldron — were joined by special guest Bradley, who has achieved financial independence through trading. Together, they shared their personal journeys, core strategies, and market outlooks.

Read more>>🎉Tiger Brokers Celebrates "Trade to Win Season 4" Winners and Announces 2026 Season

Trade to win winners events - on-site photos

Trade to win winners events - on-site photos

Trade to win winners events - on-site photos

1. Core Trading Philosophies: Balancing Discipline and Conviction

1.1 Sean: From Emotional to Systematic

Sean, who has ranked in the top 10 for three consecutive seasons, has evolved his approach over the past year:

• Expanding from U.S. Stocks to Global Markets: Initially focused on U.S. equities, he shifted 50% of his portfolio to Hong Kong and China A-shares in the second season and recently pivoted toward software stocks.

• AI-Augmented Decision Making: He uses machine learning tools to analyze market data, paying close attention to technical patterns like “double bottoms” to identify reversal opportunities.

• Thesis Over Price Action: “Why I bought a stock matters more than short-term price moves. If the investment thesis remains intact — like Alibaba is still Alibaba — I won’t sell even if it drops 15%.”

1.2 Caldron: The Long-Term Holder

Caldron’s strategy is defined by patience and concentration:

• Holding Periods in Months or Years: Core positions like Tesla are held through drawdowns of 60–70%.

• Averaging Up, Never Down: “I only add to winners during a recovery. Trying to catch a falling knife is too risky.”

• High-Concentration Positions: Single-stock exposure can reach 50%, reflecting his belief that “concentration builds wealth,” though he admits this tests emotional control daily.

1.3 Elite Equity: Deep Tech Focus

With a background in IT, Elite Equity naturally gravitates toward tech:

• Sector Insight as an Edge: His industry knowledge helps him identify technological shifts early.

• From Concentration to Diversification: Once allocating 40–50% to a single stock, he now caps individual positions at 20%.

• Options for Enhanced Returns: He actively employs various options strategies on core holdings to boost gains.

2. Risk Management: A Common Thread Among Champions

Despite different styles, all three emphasize disciplined risk management:

2.1 Logic-Based Exits Over Price Stops

Sean: “Only speculative positions like short puts have hard stops, usually at 50% loss of premium.”

Elite Equity: “For quality companies, I average down if the thesis holds.”

2.2 Position Sizing Is Key

Caldron caps speculative trades at 2% of capital.

2.3 All avoid chasing parabolic moves.

Transparency as a Mirror The live ranking system acts as a emotional barometer. Caldron admits, “Seeing my rank drop still affects me. It’s a reminder of how hard it is to stay detached.”

3. Market Outlook: Divergence and Consensus

3.1 Views on current markets varied among the panelists:

Bullish on China:

Sean plans to increase exposure to Chinese stocks, arguing that many quality names remain undervalued.

Mixed Reactions to Fed Leadership Change:

• Elite Equity is more cautious given the incoming chair’s reputation for hawkishness and may take some profits.

• Caldron remains unfazed, sticking to his existing portfolio.

The AI Wave:

Sean expects rotation from hardware to software, citing opportunities in enterprise software like Salesforce and Oracle.

Special Feature: From Major Losses to Financial Freedom — Bradley’s Journey

A highlight of the event was Bradley, 37, who retired in October 2024 after reaching a million-dollar portfolio.

His Turning Points:

1. Learning from the Meme-Stock Disaster: Losing 80% during the 2021 frenzy pushed him to master options Greeks and short-selling mechanics.

2. Trading Geopolitical Macroe Trends: He successfully traded rare earth and memory chip themes by monitoring policy shifts.

3. Leveraging Tools: He praised Tiger Brokers’ platform and AI tools, using custom scripts to prepare watchlists for nightly trading sessions.

Advice for All Traders:

• Filter the Noise: Use social media wisely by following accounts that share Bloomberg-grade insights.

• Embrace the Solitude: Though he now trades alone after his study group dissolved, he still values community learning.

The Tournament’s Value: From “Lone Competition” to “Collective Evolution”

The meetup underscored how Trade to Win has evolved from a pure performance contest into a community where traders learn and grow together.

As host James Ooi summarized, “What stands out is not just the returns, but the process, mindset, and character each contestant demonstrates.” By creating this transparent, collaborative arena, Tiger Brokers is redefining how retail investors develop — a space where every trade is understood, every breakthrough is witnessed, and true success belongs to those who can think independently yet progress collectively.

In a symbolic close, host Teresa invited Bradley to form a team — a nod to the tournament’s evolving spirit: from trading alone to winning together.

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