The Best Investments Look Dead Before They Explode w/ Eric Jackson

Watch on YouTube ↗  |  May 29, 2026 at 18:45  |  43:04  |  Milk Road Macro
Speakers
Eric Jackson — CNBC Contributor

Summary

Eric Jackson discusses his AI-driven crypto market timing model, predicts Bitcoin at $50M and Ethereum at $1.5M in 15 years, and highlights specific stock picks like Dave (DAVE) and Peloton (PTON) as well as crypto assets Sky (SKY) and Bittensor (TAO). He emphasizes finding down-and-out companies with insider buying and using dynamic risk management.

  • Eric Jackson explains his proprietary macro model that signals transitions between crypto bull, choppy, and bear markets.
  • He predicts Bitcoin will reach $50 million and Ethereum $1.5 million in 15 years, driven by agentic AI adoption.
  • He is bullish on Dave (DAVE), an AI-powered lending platform with low default rates and rapid growth.
  • He sees Peloton (PTON) as a turnaround play with 2 million subscribers and a new CEO.
  • He likes Sky (SKY) stablecoin for its mortgage partnership with Better, saving 100 basis points.
  • He is also a fan of Bittensor (TAO), a decentralized AI network token.
  • He shares his process for finding beaten-down tech stocks by looking at insider buying, customer growth, and low market expectations.
  • He advocates for active risk management (e.g., hedging, reducing exposure) rather than simply holding through volatility.
Trade Ideas
Eric Jackson CNBC Contributor 0:02
Bitcoin to $50M in 15 years
Bitcoin will reach $50 million in 15 years driven by mainstream adoption of agentic AI, which will increase reliance on AI agents for financial tasks and trust in digital assets, leading to massive crypto adoption and price appreciation.
BTC HIGH
Eric Jackson CNBC Contributor 0:09
Ethereum to $1.5M in 15 years
Ethereum will reach $1.5 million in 15 years driven by the same agentic AI adoption thesis, with Ethereum serving as a foundational layer for decentralized applications and smart contracts in an AI-driven world.
ETH HIGH
Eric Jackson CNBC Contributor 31:18
Sky stablecoin with innovative mortgage partnerships
Sky is a decentralized stablecoin that offers a 100 basis point advantage over traditional mortgage rates through its partnership with Better, making it an innovative and underfollowed crypto asset with strong growth potential.
SKY MED
Eric Jackson CNBC Contributor 32:53
Bittensor decentralized AI network token
Bittensor is a decentralized AI network token that Eric Jackson likes after studying its white paper, seeing potential for growth as AI and crypto converge, though he provides less detail on specific catalysts.
TAO MED
Eric Jackson CNBC Contributor 33:31
Dave AI lending growing fast
Dave is an AI-driven lending platform targeting lower-credit consumers with short-term loans based on cash flow analysis, boasting very low default rates, rapid growth, and a new credit card product, with significant upside remaining even after a 50x run from $5 to $270.
DAVE HIGH
Eric Jackson CNBC Contributor 36:32
Peloton undervalued with steady subs
Peloton is a beaten-down former COVID darling with 2 million steady subscribers providing recurring cash flow, a smart new CEO, and a path to growth; Eric bought around $4 and sees the stock potentially reaching high teens in a couple of years as a turnaround story.
PTON HIGH
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This Milk Road Macro video, published May 29, 2026, features Eric Jackson discussing BTC, ETH, SKY, TAO, DAVE, PTON. 6 trade ideas extracted by AI with direction and confidence scoring.

Speakers: Eric Jackson  · Tickers: BTC, ETH, SKY, TAO, DAVE, PTON