

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
- Billabong XXL Biggest Paddle2003 · world record paddle-in↗
- Magnetic (Netflix)2018 · Nazaré↗
- World Surf LeagueAthlete profile↗
- Nazaré hold-down2019 press coverage↗
- Permissionless PodcastWith Heidi Chakos↗
- Crypto TipsYouTube · since 2016↗
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.
35 guides by Toby.
Regulation & TaxCrypto 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 CunninghamStablecoins
StablecoinsStablecoin 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 CunninghamWallets & Custody
Wallets & CustodyHow 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 CunninghamFundamentalsFundamentalsThe 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 CunninghamFundamentalsFundamentalsMarket Update/Thoughts On Current Events
Toby CunninghamFundamentalsFundamentalsTrade Alert 20th November 2025
Toby CunninghamFundamentalsFundamentalsMarket Update November 18 2025
Toby CunninghamReviews & SafetyReviews & SafetyTrezor 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 CunninghamAnalysis
AnalysisSpot 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 CunninghamEDITORIAL REVIEW
Reviewed by Toby
- Multisig Explained: How to Split Your Bitcoin Keys and Why It Matters
- Crypto Scams on Telegram: How to Spot a Fake Channel, Admin or Bot
- Lost or Stolen Hardware Wallet, or the Maker Goes Bust: What Happens to Your Crypto
- How to Legally Reduce Your Crypto Taxes: What We Did and What Actually Works in 2026
- Second Citizenship by Investment for Crypto Holders: What It Costs in 2026 and What We Learned Doing It
- Portugal Residency and Crypto Taxes in 2026: What Changed and What We've Learned Living Here
- Is Crypto.com Safe? Licences, Hacks, Complaints and the CRO Decision, Reviewed for 2026
- Ledger Recover Explained: How It Works and Why We Don't Use It