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Toby Cunningham
CO-FOUNDER

Toby Cunningham

Toby Cunningham is co-founder of Learning Crypto. He has been in crypto since 2012 and co-hosts the Crypto Tips YouTube channel, which he and Heidi Chakos started in 2016.

  • In crypto since 2012
  • Billabong XXL Biggest Paddle (2003)
  • Netflix’s Magnetic · Nazaré

ABOUT

About Toby

Toby Cunningham is co-founder of Learning Crypto and has been in crypto since 2012 — trading and holding through every cycle since. He co-hosts the Crypto Tips YouTube channel, which he and Heidi Chakos started in 2016 and which has grown past 200,000 subscribers. He writes the site's market-structure and on-chain analysis: Bitcoin cycle indicators, ETF flows, DeFi mechanics and the discipline of sizing risk. Together they also host the Permissionless Podcast.

Before crypto, Toby was a professional big-wave surfer. In 2003 he won the first Billabong XXL Biggest Paddle award for a 56-foot wave at Todos Santos, Mexico, then the world record for a wave caught without a tow. He lives in Nazaré, Portugal, where he still surfs and drives jet-ski safety on the largest waves in the world, and he appears in the Netflix documentary Magnetic (2018). His February 2019 five-wave hold-down at Nazaré was covered by Surfer, The Inertia and SurferToday.

That background shapes how he writes about markets: respect the downside, ignore the hype, and never confuse a good outcome with a good decision. Originally from San Diego, Toby has been trading and holding Bitcoin through every cycle since 2012.

ALSO BY TOBY

Books, press & profiles

Toby holds Bitcoin in self-custody and does not take payment for coverage or rankings. Affiliate links are marked where used. This author page was last reviewed on 17 September 2026. Full disclaimer.

GUIDES

31 guides by Toby.

DeFiDeFi

What Is Liquidation in Crypto? Understanding Forced Closures in Trading

Liquidation in crypto is the automatic, forced closure of a leveraged position when losses push your collateral below the exchange's maintenance margin, usually 10% to 20% of the position. The exchange sells at market, deducts a 0.5% to 1% fee and returns whatever is left, often close to nothing. A 5x long on Solana at $200 with 15% maintenance margin dies near $190.

Toby Cunningham
AnalysisAnalysis

Arbitrage Trading in Crypto: How to Profit from Price Differences

Crypto arbitrage means buying an asset on one exchange and selling it on another where it trades higher, pocketing the gap. It is legal and gaps still appear, but typical spreads have shrunk to 0.1% to 2% and vanish in seconds, so the profit goes to automated bots with large capital and low fees. For most retail traders, fees and speed make it unprofitable.

Toby Cunningham
DeFiDeFi

DeFi Trading Explained: How to Trade in Decentralized Finance

DeFi trading is swapping cryptocurrencies through smart contracts and community-funded liquidity pools rather than a company's order book. You connect a Web3 wallet such as MetaMask, hold some of the chain's native token for gas, and trade on a DEX like Uniswap or an aggregator like 1inch. Start with a small test swap and watch your slippage setting; flash loans and yield farming can wait.

20 min read/Toby Cunningham
Scams & RiskScams & Risk

Pump and Dump Schemes in Crypto: How to Spot and Avoid Them

A pump and dump is market manipulation where organized groups quietly buy a thin, obscure token, flood social media and paid influencers with hype to push the price up, then sell their holdings into the retail buying frenzy. Warning signs include synchronized shilling, anonymous teams, low liquidity and promised price targets. Position limits, stop-losses and an exit plan set in advance are the practical defenses.

17 min read/Toby Cunningham

EDITORIAL REVIEW

Reviewed by Toby