Taiki Maeda
August 27, 2025

How to Make it This Cycle w/ CryptoMessi

Crypto veteran CryptoMessi joins the podcast to unpack the bewildering state of the current market cycle. He shares hard-won lessons on adapting trading strategies, the psychology of selling, and how to preserve wealth after you've made it.

Navigating an Uncharted Cycle

  • “Anybody that was here in 2021 knows this is nothing like 2021... I genuinely do not know how much longer we have.”
  • This market lacks the clear, all-ships-rising tide of previous cycles. Wealth events, like the Solana meme coin frenzy, have been isolated phenomena rather than a market-wide “alt season.”
  • Traditional cycle indicators are less reliable due to new variables like institutional ETFs and a surprisingly pro-crypto political environment, creating a confusing mix of signals.
  • The strategy of rotating profits from one hot narrative to the next is failing. Success now demands a high-conviction, "believe in it and stick to it" approach, as asset performance is highly dispersed.

The Psychology of Trading and Selling

  • “Crypto is a butthole. Exit only. Never put money back in crypto that you have taken out... Real money does not go in crypto.”
  • "Selling is a lot like that post-nut clarity... when you're in the bag... you're going to have this dopamine surge. None of it's real until you sell."
  • The biggest hurdle is selling. Stablecoins on-chain feel like “play money,” encouraging reckless reinvestment. Converting gains to fiat in a bank account creates crucial psychological friction.
  • Messi describes selling as achieving “post-nut clarity.” Once you sell a small portion of a beloved asset, the dopamine-fueled attachment fades, making it easier to see it objectively and sell more.
  • Comparison is the thief of joy. Seeing peers celebrate massive wins while your own high-conviction bets lag can create immense anxiety and lead to poor, emotionally-driven decisions.

Wealth Preservation After the Win

  • “One of the first impulses... after you've made it is you're going to want to spend money on making sure people know that you've made it... It alienates you.”
  • After a life-changing win, the dopamine withdrawal is real and can lead to irrational decisions. The first step is to do nothing—let the money sit in a bank account until it feels “normal” to you.
  • Avoid the trap of status-seeking lifestyle inflation (supercars, luxury watches). These purchases are often driven by a need for external validation and rarely bring lasting happiness.
  • Focus on converting crypto wealth into long-term, sustainable cash flow through real-world assets. Your crypto skills don't automatically make you a good real-world investor.

Key Takeaways:

  • This cycle defies historical comparison, demanding a shift from rapid rotation to high-conviction holds and a disciplined approach to profit-taking. The real challenge isn't just making money, but psychologically managing the wins and securing your wealth for the long term.
  • Ditch the Rotator Playbook. This isn't 2021. Stop chasing every pump. Success this cycle requires picking a few narratives, believing in them, and holding with conviction.
  • Make On-Chain Money Real. Stablecoins encourage bad habits. Cash out profits to a real bank account to create a psychological barrier against recklessly aping your gains back into the market.
  • Plan for Post-Win Depression. The dopamine crash after a massive score is inevitable. Resist the urge to chase that high; prioritize building sustainable, real-world income instead of buying status symbols.

For further insights, you can watch the podcast here: Link

This episode offers a raw, unfiltered look at the psychological warfare of the current crypto cycle, exploring why traditional strategies are failing and how to survive the mental and financial volatility.

Analyzing the Current Crypto Cycle

  • The Alt Season Debate: Messi pushes back against the idea that the Solana meme coin mania constituted a true "alt season." He defines a genuine alt season as a byproduct of enormous, market-wide froth that lifts all assets, not a localized wealth event.
  • Key Quote: Messi states, "Anybody that was here in 2021 knows this is nothing like 2021... every single cycle has had an alt season and an alt season is just like a byproduct of the enormous levels of froth that exist you know towards the later part of a cycle."
  • Strategic Implication: Investors should be cautious about declaring the cycle's peak based on isolated sector rallies. The absence of a broad, all-encompassing alt season suggests the market may have different dynamics or more room to run.

Conflicting Market Signals: Bullish and Bearish Cases

  • Bullish Factors:
    • The pro-crypto political stance of figures like Donald Trump, which was absent in previous cycles.
    • The potential for massive institutional inflows, with some analysts predicting trillions in new stablecoins.
  • Messi's Uncertainty: He candidly admits his confusion, assigning 50/50 odds to the cycle continuing versus topping out soon. He emphasizes the need for flexibility and avoiding rigid mental frameworks.
  • Actionable Insight: The current market is defined by unprecedented political and institutional factors. Investors must remain highly adaptable, as historical cycle models may no longer apply. Messi advises being mindful of year-end de-risking for tax efficiency, regardless of cycle theories.

The Failure of Old Strategies and the Rise of Conviction

  • Market Fragmentation: The proliferation of L2s (Layer 2 scaling solutions) and alternative L1s has created hundreds of ecosystems competing for attention, unlike the handful of dominant chains in 2021.
  • The New Meta: Conviction: Success in this cycle, according to Messi, requires picking a few assets with strong narratives and teams and holding them with conviction. Constant rotation is more likely to lead to missing the few concentrated winners.
  • Key Quote: "If you want to do really well this cycle, I feel like you can't really be this kind of heavy rotator... You got to pick something and believe in it and stick to it."
  • Strategic Implication: Researchers should focus on identifying protocols with sustainable narratives and strong fundamentals rather than chasing short-term momentum. Investors should consider concentrating capital in a smaller number of high-conviction plays.

The Psychological Toll of Underperformance

  • Comparison is the Thief of Joy: Both speakers acknowledge the intense psychological pressure of seeing others succeed, especially when your own high-conviction bets are underperforming.
  • DeFi's Curse of Cash Flows: Messi notes that protocols with strong revenue, like Maker and Ethena, are often tethered to their cash flows and may not experience the explosive, narrative-driven pumps of other assets. The market prices in their revenue, limiting their premium.
  • Actionable Insight: Mental capital is as crucial as financial capital. Investors should set clear personal performance goals and avoid comparing their results to others on social media. Recognize that revenue-generating DeFi assets may behave more like value investments than high-growth tech stocks.

Navigating Disillusionment and Staying Engaged

  • The Importance of Staying Interested: Even when the market feels irrational or corrupt, the key is to keep exploring, trying new things, and maintaining an open mind. This persistence is what leads to discovering the next major opportunity.
  • Hyperliquid as a Case Study: The airdrop for Hyperliquid, a decentralized exchange, rewarded users who stuck with a platform that was initially clunky. Those who held the airdrop with conviction saw a further 10-20x gain, proving that believing in a project can pay off immensely.
  • Strategic Implication: Don't let market cynicism lead to apathy. Actively researching new protocols, even those that seem unpolished, is essential. Survivorship in crypto often comes down to staying in the game long enough to catch the next wave.

The Cardinal Rule of Selling: "Crypto is a Butthole, Exit Only"

  • Stablecoins vs. Fiat: Messi explains the critical psychological difference between holding profits in stablecoins versus a real bank account. On-chain funds feel like "play money," making it easy to ape into new, risky trades.
  • The Necessity of Friction: To combat this, he advocates for converting profits to fiat and withdrawing them. This creates a mental barrier that protects capital from impulsive decisions.
  • Key Quote: "Real money does not go in crypto. Crypto's... a butthole. Exit only."
  • Actionable Insight: Implement a strict off-ramping strategy. When taking profits, move a significant portion completely out of the crypto ecosystem into a traditional bank account to solidify gains and prevent reckless re-investment.

Recognizing Tops and Managing Risk

  • DeFi-Specific Risks: He warns about hidden risks even in seemingly safe DeFi protocols. He points to the GMX V1 exploit as an example of how even battle-tested code can fail. He also highlights the practice of "rented TVL," where protocols temporarily inflate their TVL (Total Value Locked), a metric representing the total assets deposited, creating a false impression of growth.
  • Strategic Implication: When evaluating DeFi protocols, scrutinize the source and stickiness of their TVL. Be wary of protocols with sudden, parabolic TVL growth that isn't supported by organic user activity. Prioritize protocols with transparent and sustainable revenue models that offset token emissions.

Life After "Making It": Preserving Wealth and Sanity

  • Dopamine Withdrawal: The high from a parabolic portfolio is more intense than any drug. The subsequent crash can lead to depression, irrationality, and a desperate urge to chase that feeling again, often through reckless investments.
  • Avoid Lifestyle Inflation: Resist the urge to immediately buy supercars and luxury watches to signal status. These are often "dick magnets, not chick magnets" and alienate you from normal life. The primary focus should be on securing long-term stability, like buying a house with cash.
  • Let the Money Normalize: Do not make any major financial decisions until the new level of wealth feels "normal." This prevents you from treating it like house money and allows for more rational, long-term planning.
  • Actionable Insight: If you experience a major financial windfall, immediately off-ramp a significant portion to fiat. Wait several months before making any large purchases or investments. Focus on creating sustainable, real-world cash flow through investments like commercial real estate or stable businesses to secure your future.

The "Post-Nut Clarity" Analogy for Selling

  • Selling Breaks the Spell: Just as post-nut clarity can make you question your recent decisions, selling a portion of a beloved asset breaks the emotional attachment. It makes you see the asset more objectively and makes it easier to sell more if needed.
  • Key Quote: "That same bag you feel that way about, you sell a little bit. You're gonna have a little post-nut clarity there. All of a sudden it becomes a lot easier to sell more because you realize that selling it wasn't so bad."
  • Strategic Implication: To overcome the emotional barrier of selling, start by selling small, incremental amounts (e.g., 10%). This action can break the "hodl" hypnosis and allow for more rational portfolio management.

Conclusion: Build a Bullish Life Chart

This conversation underscores that surviving crypto requires immense psychological grit and a shift from short-term tactics to long-term wealth preservation. The ultimate goal is not just a bullish portfolio chart, but a bullish life chart—one defined by progressively higher lows in finances, mental health, and overall well-being.

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