Crypto Cycle Trading Psychology from Top Traders

Video source: Mastering the Psychology of Crypto Cycles | David Kalk Jeff Park

Guests: David Kalk, Jeff Park

Moderator: Yano, Santi

Original translation: Peyton, 7 UPDAO analyst

David Kalk of Reflexive Capital and Jeff Park of Bitwise explore the critical role of psychology in cryptocurrency trading. They argue that mastering one’s emotions and biases is key to outperforming others in the highly volatile and reflexive cryptocurrency markets. They dissect the limitations of traditional venture capital approaches, the potential of liquid strategies, and why mental toughness may be the most valuable advantage in the cryptocurrency space today. They share their perspectives on managing trading psychology, adapting to market institutions, and the future of institutional cryptocurrency investing.

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DavidJeff Introduction

David Kalk is the founder and chief investment officer of Reflexive Capital. He has a rich background in macro trading and began his career at Goldman Sachs in 2008, focusing on interest rate derivatives. He then joined Peter Thiels family office as chief investment officer of the macro fund, where he honed his risk management and trading skills. In 2020, he helped start CommonHealth Asset Management and began to focus on cryptocurrencies as macro assets. In July 2023, due to his passion for the crypto market, David founded Reflexive Capital, dedicated to developing institutional-grade cryptocurrency products.

Jeff Park is the Head of Alpha Strategy and Portfolio Manager at Bitwise. He has extensive experience in investment strategy and portfolio management. As an expert in alpha generation and investment management, Jeff has played a key role in shaping Bitwises investment approach and strategy.

Crypto is the most liquid inefficient market

Yano: Initial question

Yano asked David Kalk to summarize his argument for cryptocurrencies.

David Kalk: Perspectives on the Crypto Market

David Kalk believes that cryptocurrency is the most liquid inefficient market. Although the market is liquid, it is extremely inefficient due to the lack of professional trading experience and the presence of venture capital (VCs) and retail investors. He believes that professional traders and risk managers can gain significant advantages by dynamically adjusting and adapting to different market environments.

Santi: Questions about venture capital funds

Santi asked why many liquid funds tend to experience drawdowns, whether it is because of the managers’ inadequacy or because they are not focused.

David Kalk: Skill Differences

David responded that the skills required for trading and VC investing are very different. Traders must be flexible and react to price changes, while VCs focus on long-term investment thesis. He added that in the cryptocurrency space, people often become too closely tied to their investments, which can impair rational decision-making.

Yano: Ask Jeff Park

Yano then asked Jeff Park about his role at Bitwise and how he creates revenue for the company.

Jeff Park: Role at Bitwise

Jeff explained that Bitwise focuses on crypto asset management, takes a multi-strategy approach, and forms partnerships with unique crypto return opportunities. He emphasized Bitcoins inherent volatility and sees it as an opportunity rather than a drawback, especially in liquid and actively traded strategies.

Yano: Follow-up question from last week’s podcast

Yano asked David to share his thoughts on key points from last week’s podcast.

David Kalk: Reflections on Podcasting

David said he respected the previous guest and agreed with some of the points, such as the importance of finding an edge in the market. However, he differed on two points: suppressed volatility increased risk, and market psychology was too confusing to rely on. He believed that the current market structure was very different from the past, so adjusting strategies was crucial.

Santi: Comments on market behavior

Santi shared an example of a fund manager who held cash during a rising market and subsequently profited in the subsequent bear market. He agreed with David and highlighted the challenge of managing investor expectations in volatile markets.

Jeff Park: Challenges with LPs

Jeff discussed the unique expectations of crypto fund LPs (limited partners), who often seek short-term gains, which is inconsistent with long-term venture capital strategies. He emphasized the importance of managing these expectations in volatile markets such as crypto.

David Kalk: Adaptability in the Crypto Market

David concluded by stressing the importance of adapting and evolving as markets evolve, knowing when to shift strategies and when to hold onto cash for long-term success.

Santi: Identification

Santi agreed with David, stressing the importance of flexibility and being ready to adjust strategies as market structures change.

LP Priority

David Kalk: LP Priority and Strategy Design

David Kalk discussed the distorted return profile in cryptocurrency investing, highlighting that many allocators are not just looking at absolute returns, but want to achieve returns within a specific volatility profile. He noted that while there is interest in strategies that effectively manage volatility (such as allocating 80% of funds to cash and 20% to cryptocurrency strategies), the industry has not yet created a return profile that appeals to these allocators. David believes that in order for these strategies to attract new funds, they need to be packaged correctly.

Santi: Question about the attractiveness of strategy

Santi asked the two speakers how attractive such strategies are to limited partners (LPs), especially considering that most LPs are used to categorizing investments as hedge funds or venture capital. He noted that the concept of “liquid venture capital” often confuses LPs, causing them to pass on investment opportunities.

David Kalk: The right structure is needed

David agrees that the concept of liquid venture capital does not effectively meet the needs of LPs. He believes that the strategy must be a true hedge fund strategy without major drawdowns to be classified as a hedge fund. Although cryptocurrencies have attractive risk-return characteristics, previous investment practices were often reckless and poor leverage management led to crashes. David questioned whether this was due to the difficulty of the strategy itself or because the wrong people were managing it.

David Kalk: Psychological Advantages and the Role of Risk Management

David stressed that psychological advantages and risk management are crucial in trading, especially in the cryptocurrency space. He noted that while many people from traditional finance (TradiFi) think they can apply the same principles to crypto, this does not always work. He suggested that the 2018 batch of managers should not be seen as an indicator of what can be achieved with real experience and talent in the cryptocurrency space, hinting that the industry needs more serious and competent efforts.

Liquidity vs Private Markets

Jeff Park: The importance of investment vehicle structure

Jeff Park highlights the critical role of investment vehicle structure when comparing beta-focused approaches to liquid alpha-focused approaches. He notes that in an open-end structure, annual fees and settlements can become a burden, especially if the fund experiences large swings. Investors seeking risk management may prefer closed-end funds, especially venture-focused funds, where incentives are better aligned through distribution waterfalls, allowing for greater patience. However, in an open-end structure, large swings in performance can leave investors worse off than with a general partner (GP). Jeff highlights that these structural issues are significant and why some investors are wary of certain investment vehicles.

Jeff Park: The transformative potential of the cryptocurrency space

Jeff acknowledged that, as David mentioned, there is potential for change in the cryptocurrency investment space. He noted that new trading mentalities and financial innovations, such as the launch of Bitcoin ETFs and the possibility of options on these ETFs, mark the convergence of traditional financial instruments with cryptocurrencies. This could lead to more risk-managed trading solutions. However, Jeff stressed that having the right investment vehicle structure that aligns with the interests of limited partners (LPs) is critical, which is an issue that has not been adequately addressed in the past but offers hope for the future.

David Kalk: Trading is a professional skill

David Kalk challenges the assumption that traditional portfolio managers (like someone who has been trading oil for 20 years at Millennium) are bound to fail in cryptocurrency trading. He argues that trading is a professional skill, and there are probably some people who have excellent trading abilities in the cryptocurrency space, just as there are in venture capital. However, David notes that he does not often come across people who have the discipline and self-awareness to understand and exploit their own cognitive biases in their trading strategies. He questions whether such individuals exist in the cryptocurrency space.

The value of psychological advantage

Santi: The importance of identifying biases and managing emotions

Santi responded by sharing his experience of regular discussions with David, which often begin with questions like “What am I not seeing? What are my current biases?” He suggested that this focus on identifying blind spots and managing emotions are the most critical aspects of successful trading, emphasizing the importance of self-awareness and emotional control during the trading process.

David Kalk: The Importance of Psychological Advantages in Cryptocurrency

David Kalk asserts that psychological advantages may be the most important advantages in the cryptocurrency market. He notes that in traditional markets, survivors often develop this advantage through years of experience. In the cryptocurrency space, those with psychological resilience have a huge opportunity, especially since many have moved from actively managing their portfolios to a buy-and-hold strategy. However, David criticized this approach, noting that many assets in previous cycles have not maintained their value. He stressed the importance of adapting and actively managing positions in such a volatile environment, rather than sticking to a buy-and-hold mentality.

Santi: The challenges of holding major assets and managing volatility

Santi stressed that most managers are reluctant to simply hold the main assets, especially with the rise of ETFs. He acknowledged that clients pay management fees to obtain excess returns, which sometimes involves holding cash or main assets such as Bitcoin or Ethereum. He believes that the key to managing a chaotic asset class like cryptocurrency is to guide clients through volatility, which is the real value provided by managers.

David Kalk: Balancing major holdings with active strategies

David compared the dilemma to the stock market, where managers often hold major holdings like Apple or Amazon. The challenge, he noted, is balancing those holdings with other strategies to justify the fees the manager charges.

Santi: Focus on results rather than intellectual justification

Santi stressed that the focus should be on delivering results, not just holding assets and constructing overly complex intellectual arguments. He stressed that the goal is to outperform, not just appear smart in client communications.

David Kalk: Investor restrictions hinder flexibility

David discusses the dilemma managers face due to restrictions and interference from investors, which greatly hinders their ability to effectively execute strategies. He argues that this lack of flexibility is a major problem in fund management.

Santi: Trust and freedom in managers

Santi believes that investors need to trust the wisdom of managers and allow them to execute strategies without being overly restrictive. He believes that investing is about trusting the ability of managers and giving them the space to do their job.

David Kalk: The critical role of flexibility and adaptability

David stressed that flexibility is crucial, especially in the dynamic cryptocurrency market. He believes that being able to adapt and avoid being bound by rigid restrictions is the key to success.

Santi: Balancing downside risks and capturing upside potential

Santi agreed, noting that the key is to manage downside risk and preserve capital while still capturing most of the upside potential, even if that means not reaching the absolute top.

David Kalk: The concept of market reflexivity in cryptocurrencies

David introduced the concept of market reflexivity, which is particularly important in cryptocurrencies. He explained that markets are subject to feedback loops, where price changes affect fundamentals, which in turn affect prices. This phenomenon is particularly evident in cryptocurrencies, where the lack of clear valuation metrics allows prices to fluctuate freely and sometimes illogically. He asserted that understanding these feedback loops is essential to navigating the market.

Santi: The importance of risk management in volatile markets

Santi reiterated that managing risk is crucial, especially in a market like cryptocurrencies where psychological factors can lead to extreme price swings.

David Kalk: Adapting to market reflexivity

David discusses the importance of understanding and adapting to the markets reflexive patterns. He states that success is not about predicting exact tops and bottoms, but about understanding the markets current state and adjusting accordingly.

Santi: Tips for knowing when to quit

Santi admitted that it’s easy to be a perpetual long in crypto, but the real skill lies in managing risk and knowing when to exit, even if it means missing out on some gains.

David Kalk: Achieving long-term success through flexibility and adaptability

David concluded by stressing that flexibility and adaptability are the keys to long-term success in the cryptocurrency market. He emphasized the importance of understanding the dynamics of market psychology to make informed decisions.

Jeff Park: The impact of ETFs on the cryptocurrency market

Jeff Park pointed out that the launch of ETFs, especially Bitcoin ETFs, is a game changer. Although Bitcoin is the representative of the cryptocurrency industry, it does not represent the entire asset class. He believes that Ethereum may attract more interest from institutional investors as a bet on future technology. Jeff believes that ETFs may serve as a bridge to wider adoption, but the real impact will be seen as funds begin to flow into the broader cryptocurrency ecosystem.

Navigating the market environment

Santi: Discussing the current market environment

Santi opened by asking about performance over the past three to six months from an investment perspective, acknowledging the challenges of the current environment. He was curious if there were any changes in mental models that helped or will help outperform in the current cycle.

Jeff Park: The value of a multi-manager strategy

Jeff Park responded by referring to a point he made in a podcast with Tar that it is unrealistic to expect a single manager to excel in all areas - including fundamental analysis, trading data, market neutral strategies, etc. Instead, he stressed the importance of selecting managers who are strongest in specific areas, which is consistent with their multimanager approach. This approach has proven valuable over the past six months.

Jeff illustrates this through the various returns of multi-strategy approaches. For example, Bitcoin ETFs enabled discretionary macro trading, while automated trend strategies also outperformed. In March, high-frequency trading strategies provided the best risk-adjusted returns during the meme token mania. By April, the focus turned to decentralized finance (DeFi) projects such as Pendle and Ethena. As David Kalk mentioned before, the tokens that perform well in this cycle may be different compared to previous cycles, which highlights the importance of actively integrating novel primitives.

This pattern continued to develop in May and June, with opportunities emerging in Layer-1 protocols and yield farming strategies. Jeff mentioned that at Bitwise, their goal is to provide investors with a full range of strategies, including reflexive macro trading, supplemented by multiple orthogonal return vectors in liquid strategies.

David Kalk: Systematic processes and the challenges of adapting to market cycles

David Kalk added that each market cycle presents unique challenges. He noted that one difficulty in systematizing any investment process is the limited sample size. For example, stablecoins did not exist two cycles ago, so it is difficult to develop a stablecoin indicator. Understanding market flows is critical, and flows between Q1 and Q2 differ significantly, influenced by factors such as Bitcoin ETFs and stablecoin indicators. In addition, the market saw a technical sell-off at the end of the second quarter.

David observed that the market currently seems to be in a transition phase. He advised traders to adjust their positions and risk-taking strategies, noting that it is not wise to be fully invested throughout the cycle for those who want to retain risk. Instead, he suggested gradually increasing positions to prepare for important market fluctuations, such as the much-anticipated Super Bowl moment.

David also reviewed how some tokens showed surprising resilience in previous cycles in Q4 and Q1, despite research showing that many tokens will not survive the next cycle. Some tokens experienced significant rebounds, which highlights that investors tend to return to familiar assets, driving short-term gains. However, he warned that new developments will not necessarily drive old tokens, and stressed the importance of focusing on assets with inherent convexity.

Santi: The impact of circulating supply on older tokens

Santi followed up on David’s point by pointing out that the key difference between old tokens is their circulating supply. Tokens with large circulating supplies, especially those that are being unlocked, may significantly underperform. However, some old tokens that have unlocked most of their supply may show significant growth because they are more in line with fundamentals.

David Kalk: The impact of unlocking tokens on performance

David agreed, noting that unlocking tokens has proven to be one of the worst performing factors. If someone systematically trades based on this factor, it would be a clear strategy. He added that the focus of looking at old assets versus new assets should be on their potential to attract new capital and interest. Old assets may have difficulty inspiring new investment due to past bubbles or scams, while new tokens may provide new opportunities.

Santi: Opportunities in gaming tokens and other niche categories

Santi noted that in categories like gaming tokens, such as Axie Infinity, there has been a significant rebound from lows. While some investors may avoid assets they previously lost money on, others may see deeply discounted assets as buying opportunities.

David Kalk: Assessing Buyer Sentiment and the New Narrative

David stressed the importance of understanding who is buying these assets - previous holders, or new investors attracted by low prices. He suggested that many investors may prefer new narratives and innovative projects over assets associated with past disappointments. This shift in investor sentiment will be key in determining which assets gain attention in the future.

Jeff Park: Factor Models for Insight into Market Dynamics

Jeff Park shared some of his recent insights from factor models that study market dynamics. The research used the Fama-French model to evaluate factors such as momentum, value, and growth. It was found that growth was a persistent factor, but most profits came from short positions rather than long positions. Jeff concluded that while old tokens may have potential, most gains in recent years have come from betting on assets that have fallen.

Market sentiment management

Santi: The Challenge of Quantifying Cryptocurrency Growth

Santi opened the discussion by mentioning the challenges of quantifying growth in the cryptocurrency space, as the volatility and dynamic nature of the market complicates the task.

Jeff Park: Key Metrics for Growth Evaluation

Jeff Park responded by saying that a recent study used two main metrics to quantify growth: the total value locked (TVL) relative to market cap, which serves as a broad indicator, and weekly user engagement growth. By analyzing these variables, the study aims to rank assets and predict their potential movements. Jeff pointed out that assets that perform poorly in these metrics may decline significantly, while those that perform strongly may provide investment opportunities.

David Kalk: Reflexivity and the role of momentum

David Kalk further discussed reflexivity in the market, noting that momentum and fundamental indicators (such as the creation of new wallets) can be effective indicators. He pointed out that the best effect is when the momentum and growth factors are in play at the same time, as this combination can bring considerable profits in various market conditions. Whether applied to long or short positions, this two-factor approach has proved successful in practice.

Santi: A leading indicator for memecoins

Santi mentioned memecoins, noting that for these assets, the most critical metric is the number of wallets and their growth rate — whether it’s daily, hourly or weekly. He believes this is a leading indicator for identifying potential opportunities in the memecoin market.

David Kalk: Market mechanisms for adapting to change

David stressed the importance of identifying changes in market regimes, suggesting that if you have a framework that works for the market and notice that certain strategies are no longer working, you need to adjust your approach. Monitoring whether the growth and momentum factors continue to support each other or whether they begin to diverge can help you determine whether you have entered a new market regime.

Santi: The psychological challenge of relying on reflexivity

Santi shared his personal struggles when relying on reflexivity, admitting that he felt challenged by not believing he had an edge on the market overall. His background in traditional finance, which was very competitive, led him to question the validity of his own perspective, despite his 12 years of experience. He noted that many people who thought they had an edge ultimately underperformed or failed, and that even successful investors like Stan Druckenmiller acknowledged the unpredictability of the market. This realization led him to recalibrate his perspective, realizing that many market participants were not deeply engaged in the market, which created opportunities for those who were serious about participating.

David Kalk: Understanding and Using Trading Edges

David responded by discussing the concept of trading edges, noting that in macro trading, many professionals use similar strategies that appear to have an edge. However, when entering a new space like cryptocurrencies, traders may find that their edge is unique because others may not be using it effectively. Applying a specific edge in the absence of competition can lead to an advantage, creating opportunities for those who identify and exploit it.

Santi: The role of emotions in managing positions

Santi turned the topic to the emotional challenges in trading, especially during the memecoin supercycle. He explained the difficulty of managing a position when wallet growth suddenly began to decline. He wondered how to manage a position in this situation, especially when holding a long-term bullish memecoin, when the immediate indicators changed. The emotional impact of seeing others profit while facing the challenge of rapidly changing indicators is difficult to deal with.

David Kalk: The Complexity of Managing Emotions in Trading

David acknowledged the complexity of managing emotions in trading, noting that trading coaches often play the role of therapists. He stressed that there is no one-size-fits-all answer, but rather an understanding of which emotions lead to costly mistakes and a plan for dealing with them. This may involve reducing positions, maintaining positions, or making rational decisions based on changing information. David explained that the goal is to identify personal emotional patterns and adjust strategies accordingly. In a volatile market like cryptocurrencies, momentum plays a big role, so this requires a more flexible approach than traditional mean reversion strategies.

Santi: The importance of personal experience and flexibility

Santi shared his personal experience in the current cycle where he adjusted his approach by gradually increasing his investment in Solana, even though he did not catch the bottom. He explained the challenge of dealing with criticism from market participants for missing out on the best trades, but in hindsight he learned to accept that failing to catch the bottom was acceptable. He found that gradually increasing the size of investment can be an effective strategy. Santi recalled the DeFi summer, where the market provided enough time to catch trends even when entering the market early. Overcoming emotional paralysis and gradually adjusting strategies was a key lesson he learned.

David Kalk: The value of psychological flexibility

David couldn’t agree more, stressing the importance of psychological flexibility in cryptocurrency trading. He believes that in this asset class, it is usually more advantageous to invest in the early stages of a trend, rather than trying to catch the bottom. He concludes that the likelihood of achieving significant gains is higher when entering a trend early, rather than focusing on catching the exact bottom. David reiterates that in a market as dynamic as cryptocurrencies, adaptability and the willingness to adjust strategies based on new information are crucial for long-term success.

Is cryptocurrency worth investing in?

Santi: The Challenges of Timing and Liquidity in Crypto Markets

Santi began by discussing the difficulty of managing a position in volatile markets, especially when dealing with meme coins. He explained how the peg effect makes it difficult to adjust even if a currency falls sharply, even if it still looks like a good position. Looking back to November 2021, when interest rates began to rise and markets began to slide, Santi emphasized the importance of understanding that perfect timing is almost impossible. Instead, he advocated for holding positions with significant entry and exit points, emphasizing the importance of liquidity. He noted that a lack of liquidity can be detrimental, and that it is important to wait for better conditions rather than overtrading in volatile markets.

David Kalk: Liquidity Complexity in Trading

David echoed this sentiment, adding that while people appreciate liquidity, they often avoid it because it requires active trading, which can be psychologically taxing. He suggested that for most traders, it might be better to have fewer decisions to make.

Santi: Embracing the value of volatility

Santi contrasts this with the venture capital world, where investors have the luxury of time, sometimes waiting a decade to see if their decisions were correct. In the crypto space, however, he believes it is better to face volatility head on. If an asset drops significantly, but if the fundamentals are solid, then it could be a buying opportunity. He stressed the importance of having cash on hand and a plan to seize these opportunities.

David Kalk: The Importance of Having a Plan

David stressed the importance of having a thorough plan. While it is fine to update your plan daily based on new information, the core strategy should be built around your trading process and the wider market environment. The plan should reflect past trading experience to avoid repeating the same mistakes, and should not be changed frequently.

Santi: Responding to market changes

Santi noted that certain market events, such as the Fed’s actions and shifts in U.S. cryptocurrency policy, represent turning points. He suggested that while these developments may be viewed as pivotal points a few years from now, the opportunities to proactively act on them today cannot be ignored.

David Kalk: Balancing long-term perspectives with market realities

David agreed, but suggested shortening the time horizon to 15 months rather than two years, acknowledging that there could be significant market declines in the interim. He stressed the need to assess reactions based on market conditions and adjust investment sizes accordingly, focusing on raising funds if the narrative remains consistent. He warned against overthinking, advocating a balanced approach, staying committed to the deal without overreacting to short-term volatility.

Santi: Dealing with competition and market institutions

Santi and David discussed the importance of understanding the broader market system. While there are fewer advantages to intraday trading, a long-term perspective can provide significant opportunities, especially when considering the complex supply and demand dynamics of altcoins. They noted that Bitcoin remains the most reliable aspect of the market.

Santi: Return to the assumptions of traditional finance

Santi asked Jeff an interesting question, asking if he would consider returning to traditional finance and hedge fund macro trading given the challenges in the cryptocurrency market.

Jeff Park: The unique charm of cryptocurrency

Jeff responded thoughtfully that while traditional finance offers stability, the path forward for cryptocurrencies is both challenging and rewarding. He highlighted the unique attributes of cryptocurrencies, such as liquidity, volatility, and global reach, which are unmatched in traditional markets. Jeff finds the potential for additional returns by taking liquidity risk particularly attractive in the crypto space. He compared this to traditional markets and suggested that if the SP 500 was as volatile as cryptocurrencies, the expected return premium would be much higher. This relative discount and opportunity gap drives his passion for macro trading in cryptocurrencies.

Santi: The importance of compound interest and risk management

Santi reflected on the book The Missing Billionaires, which highlights the importance of compounding capital and risk management. He noted that many traders tend to overcomplicate their strategies, while successful market makers often achieve high returns with low risk. He stressed that even small differences in annual returns can have a significant impact on capital over a long period of time.

David Kalk: Drawdowns and the impact of mental toughness

David added that managing drawdowns is critical because big losses require big gains to recover. He stressed the importance of understanding the psychological aspects of trading, including identifying personal emotions and biases. Observing how others manage these challenges can give you an edge in the market.

David Kalk: The dangers of rigid thinking

David warns that early success in trading, such as Ethereum, can lead to rigid thinking and fixed views. He stresses the importance of building a track record that combines psychological advantages with trading advantages, which can attract new investment. While this transformation may take time, it could become very important in the next five to seven years.

Santi: Strategies for future cryptocurrency success

Santi concluded that the most successful strategies going forward will likely be those that effectively capture upside potential while managing downside risk. He acknowledged that while certain strategies may perform better in specific cycles, smart investors will recognize the value of reducing volatility and capturing returns over time.

David Kalk: Evolution of focus for capital allocators

David notes that traditional money allocators are gradually shifting their focus towards evaluating strategies based on their actual performance rather than relying solely on historical norms, which is indicative of a broader trend in investment approaches.

Santi: Final thoughts and suggestions

Santi asked Jeff if he had any final thoughts or advice, and Jeff recommended the book Market Wizards as a must read. The book provides valuable insights into the psychology of trading behavior, which are particularly important in the unique structure of the cryptocurrency market.

Santi: The value of therapy in trading

Santi agreed, sharing that therapy has been a valuable investment for him, providing new perspectives and support by discussing challenges with someone outside of his circle.

David Kalk: The Role of a Trading Coach

David agrees, stressing the importance of trading coaching and psychological methods to help ensure a healthy mindset when making decisions.

Jeff Park: Parenting and Trading Perspectives

Jeff added that having children has given him a different perspective on trading, affecting his time management and stress levels.

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