Taiki Maeda
August 28, 2025

My $40,000 Polymarket Bet

DeFi researcher Taiki Maeda details his pivot from sophisticated token analysis to placing a $40,000 bet on Polymarket. The wager: will controversial stuntman "Lord Miles" complete a 40-day water fast in the desert?

Anatomy of a Wild Bet

  • “You went from buying sophisticated DeFi crypto coins to betting on some random guy to fast in the desert. And I understand. I feel you.”
  • “If there's a rigged market, I'm going to ask myself how rigged is it in favor of one side or the other? And then I'm like, okay, what's the plus EV decision there?”
  • The bet centers on Lord Miles, a personality known for extreme stunts like visiting Afghanistan during the fall of Kabul. Maeda accumulated 40,000 "Yes" shares at an average cost of $0.52, risking $40,000 for a potential $20,000 profit.
  • The market became attractive after Miles moved from the open desert to an air-conditioned luxury tent to keep his livestream running. This change, approved by Polymarket, dramatically increased his odds of success.
  • The core thesis is that the market is "rigged" in favor of "Yes." Miles has complete control over the outcome and is in direct communication with Polymarket to clarify rules as he goes, allowing for vitamin consumption and location changes.

The Dystopian Social Layer

  • “Once money is on the line, people will just go out of their way to find an edge.”
  • “It is quite dystopian because at some point there is enough financial incentive to rig it... bring a bunch of guns or a knife, bring like orange juice and then be like, 'I'm going to shoot you if you don't consume this orange juice.'”
  • Financial incentives have created a PvP (Player vs. Player) environment. A major "No" shareholder, Windwalk3, has invested over $260,000 and is actively trying to disqualify Miles by filing lawsuits and scrutinizing his every move.
  • Bettors have gone to extreme lengths to gain an edge, from using Google Maps to dox Miles's location to analyzing the species of his pet cat to confirm he has access to air conditioning.
  • This market highlights the perverse incentives of prediction markets, where large bettors could theoretically be motivated to physically sabotage the event to ensure their desired outcome.

Prediction Markets as an Uncorrelated Asset

  • “My belief is that prediction markets should be uncorrelated from the crypto markets. So if I think that we are potentially entering a crypto bear market... it would be good for me to develop expertise in prediction markets.”
  • Prediction markets offer a venue for +EV (positive expected value) bets that are completely detached from traditional crypto market cycles, making them a valuable hedge during bear markets.
  • Beyond the primary bet, Polymarket presents an airdrop farming opportunity. Maeda uses multiple wallets to spread his volume and increase his potential allocation if the platform launches a token.
  • Other opportunities exist in mispriced markets, such as betting against moonshot odds (e.g., Ethereum hitting $17k in 2025) or betting on individuals with a track record of success, like Mr. Beast's charity fundraisers.

Key Takeaways:

  • Prediction markets are a chaotic blend of fundamental analysis, game theory, and social engineering. While seemingly degenerate, they offer unique opportunities for sharp bettors.
  • Bet on Rigged Games (If You Know Which Way They’re Rigged): When an event's outcome can be influenced by a central participant who wants it to succeed, the odds may not reflect the true probability. Identifying and betting with this influence is a core strategy.
  • Uncorrelated Returns Are Out There: Developing expertise in niche, uncorrelated markets like Polymarket can provide a valuable edge and a source of returns when broader crypto markets are stagnant or bearish.
  • Incentives Drive Everything: In markets with real money on the line, expect participants to push boundaries. From doxxing to lawsuits, bettors will exploit every available angle to find an edge, creating both risk and opportunity.

Link: https://www.youtube.com/watch?v=Skk_uuRqCa0

This episode unpacks a $40,000 bet on a man's 40-day desert water fast, revealing the bizarre, high-stakes, and potentially rigged dynamics of prediction markets like Polymarket.

The $40,000 Polymarket Bet

  • Prediction market bettor Tiki opens by detailing his $40,000 wager on Polymarket, a decentralized platform where users bet on the outcomes of real-world events. The market asks: "Will Lord Miles complete a 40-day water fast in the desert?"
  • Tiki reveals he is one of the largest holders of "Yes" shares, having invested approximately $40,000 across multiple wallets.
  • His average cost basis is 52 cents per share, positioning him for a potential $20,000 profit if Lord Miles succeeds.
  • He acknowledges the strange nature of the bet, contrasting it with his usual focus on DeFi protocols.

Tiki frames the absurdity of his shift in focus: "You went from buying sophisticated DeFi crypto coins to betting on some random guy to fast in the desert. And I understand. I feel you, right?"

The Subject: Who is Lord Miles?

  • To assess the bet's viability, Tiki provides crucial background on Lord Miles, portraying him as a controversial figure known for undertaking extreme and dangerous activities for attention. This context explains why the market gives him a non-trivial chance of success.
  • Miles gained notoriety for traveling to Afghanistan during the fall of Kabul, where he was subsequently imprisoned by the Taliban for eight months.
  • His history includes other high-risk stunts, such as illegally visiting a heavily protected, snake-infested island in Brazil.
  • Tiki characterizes him as an individual predisposed to extreme challenges, making him a unique subject for such a demanding physical and mental test.

The Challenge and Its Evolving Rules

  • The conditions of the 40-day water fast began to change almost immediately, significantly altering the perceived difficulty and influencing market odds.
  • A water fast is an extreme diet consisting only of water and electrolytes. Undertaking one for 40 days is exceptionally dangerous and typically requires strict medical supervision.
  • Initially, Miles attempted the fast in the open desert, but his live-streaming equipment overheated in the 109°F heat.
  • He then moved into a luxury camping pod with continuous air conditioning, justifying the change as necessary to maintain the 24/7 live stream required by the bet. This move caused the odds of success to rise sharply, prompting Tiki to enter the market.
  • Further controversy arose when Miles consumed vitamins on stream. After bettors bought "No" shares, Polymarket clarified the rules, stating that "ingestion of vitamins/mineral supplements without significant caloric value does not qualify as breaking the water fast."

Community Scrutiny and Market Drama

  • The financial stakes on Polymarket incentivize intense, real-time investigation from the community, turning the bet into an adversarial spectacle.
  • Bettors used open-source intelligence to pinpoint Miles's location, cross-referencing his live stream background with Google Maps images of a luxury desert resort.
  • The presence of a pet cat in his tent was cited as further proof of a comfortable, climate-controlled setting, as most cat breeds cannot survive in extreme desert heat.
  • The Polymarket comment section became a hub for accusations of fraud, with users claiming Miles and the platform were colluding to bend the rules for marketing purposes.

The Order Book Trenches and a Major Antagonist

  • Tiki analyzes the market's liquidity dynamics, focusing on the "order book trenches" and a key player actively betting against Lord Miles.
  • Order books are lists of buy and sell orders on a market. On illiquid prediction markets, a single large participant can heavily influence the odds.
  • A user named "Windwalk3" emerged as the primary antagonist, accumulating over 500,000 "No" shares by spending approximately $260,000.
  • This user provided substantial sell-side liquidity for "Yes" shares by placing large limit orders, which Tiki used to build his position.
  • Windwalk3 is a serious market participant with a reported profit and loss of over $1 million on Polymarket, primarily from a successful bet on the 2024 U.S. election.

Dystopian Incentives and the Risk of Sabotage

  • The large sums of money involved create perverse and potentially dangerous incentives for participants to influence the event's outcome directly.
  • Tiki highlights the "dystopian" reality that a large financial stake could motivate someone to physically sabotage the fast, speculating on a scenario where someone could find Miles and force-feed him.
  • Windwalk3 escalated the conflict by threatening a civil lawsuit against Lord Miles for fraud and misrepresentation.
  • In response to perceived threats, Lord Miles moved to a new, undisclosed desert location for better security. This action itself sparked further debate over whether traveling violated the "continuous" nature of the fast.

Tiki on the market's strange incentives: "At some point... there's like some financial incentive to try to affect the outcome of an event."

Tiki's Thesis: Betting on a Rigged Market

  • Tiki reveals his core investment thesis: he believes the market is structurally rigged in favor of a "Yes" outcome and has positioned his capital to exploit this edge.
  • He argues that Lord Miles has near-total control over the outcome and is highly incentivized to complete the challenge to boost his personal brand.
  • The potential for "soft cheating" combined with Miles's demonstrated grit for extreme stunts makes success highly probable.
  • Miles is in direct communication with Polymarket to clarify rules, allowing him to navigate the challenge's terms without disqualification.
  • Based on these factors, Tiki calculated the true probability of success at over 70%, creating a positive expected value (+EV) opportunity compared to the 52-cent price he paid.

Broader Opportunities in Prediction Markets

  • Tiki broadens the discussion to the strategic value of prediction markets for crypto investors, particularly as an uncorrelated asset class and a venue for airdrop farming.
  • Uncorrelated Returns: Prediction markets offer a way to generate profit independent of crypto market cycles. This is especially valuable in a potential bear market.
  • Airdrop Farming: Tiki is using multiple wallets to place bets, a common strategy to maximize a potential future token airdrop from Polymarket.
  • He identifies other potentially mispriced markets as examples:
    • Betting against Ethereum hitting $17,000 in 2025 (priced at 5% odds).
    • Betting on Mr. Beast's charity fundraiser successfully raising $40 million by its deadline.

Conclusion

This deep dive reveals prediction markets as a chaotic but potentially lucrative frontier where success hinges on analyzing human incentives and market structure. For investors, these markets offer uncorrelated returns and airdrop opportunities, demanding a unique blend of research, psychological analysis, and high risk tolerance.

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