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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

35 guides by Toby.

Regulation & TaxRegulation & Tax

Crypto Record Keeping: What to Track for Tax

Record seven things for every crypto transaction: date and time, type, asset and quantity, the fiat value at the time, fees, the venue, and the transaction ID. The fiat value is the field people skip and the hardest to reconstruct later. Export from every exchange quarterly and keep the raw files.

Toby Cunningham
StablecoinsStablecoins

Stablecoin Depegs: Why Pegs Break and What to Do

A stablecoin holds its peg through redemption plus arbitrage, so a depeg means that loop is blocked or doubted. Liquidity depegs usually recover within hours, collateral depegs depend on whether the assets are reachable, and design failures like Terra in 2022 rarely recover at all.

Toby Cunningham
Wallets & CustodyWallets & Custody

How to Set Up a Multisig Wallet: Bitcoin and Ethereum, Step by Step

You can build a multisig yourself, with no company holding a key. On Bitcoin, a free app such as Sparrow ties three hardware wallets into a 2-of-3 wallet. On Ethereum and similar networks, a Safe account does the same with a smart contract. Back up every key plus the wallet file or Safe address, and test recovery first.

16 min read/Toby Cunningham
FundamentalsFundamentals

The Weekly Alpha: The Collision of Geopolitics and Market Structure

The first full trading week of 2026 has concluded, leaving behind a complex tapestry of data that points to a market in the throes of a significant structural transition.

Toby Cunningham
FundamentalsFundamentals

Market Update/Thoughts On Current Events

Toby Cunningham
FundamentalsFundamentals

Trade Alert 20th November 2025

Toby Cunningham
FundamentalsFundamentals

Market Update November 18 2025

Toby Cunningham
Reviews & SafetyReviews & Safety

Trezor Safe 7 Review - Is It Worth It?

The Trezor Safe 7 is worth it for most people: it is Trezor's most complete hardware wallet yet, pairing the TROPIC01 chip, the first auditable secure element, with a dual secure element design, a 2.5-inch touchscreen, and Bluetooth 5.1 or USB-C. Bluetooth can be disabled for air-gapped use, though purists who want absolute isolation may still prefer a fully offline device.

Toby Cunningham
AnalysisAnalysis

Spot Trading in Crypto: What It Is and How It Works

Spot trading in crypto is buying and selling cryptocurrency for immediate delivery at the current market price, using only your own money. You own the actual coins, there is no expiry date, and you cannot lose more than you put in, which makes it the safest way to trade actively. Trades match through an exchange order book using market, limit, stop or take-profit orders.

Toby Cunningham

EDITORIAL REVIEW

Reviewed by Toby