
The Withdrawal Button You Can Never Find
Andreas Brekken, the founder of SideShift.ai, speaks less like someone arriving to pitch a product and more like an early adopter who remembers when Bitcoin was a technical curiosity posted on Slashdot.
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View full episode detailsBrekken found Bitcoin around 2011, when the community consisted mostly of hardcore libertarians attending conferences in Acapulco and tech adopters who saw a payment system that behaved differently from existing services. To him, it looked like PayPal except accounts could not be blocked, no merchant approval was required, and the software could be installed on any computer. By 2012, he was exploring the debug console inside his Bitcoin wallet, typing RPC commands to generate deposit addresses and send funds. This realization that any program able to speak JSON-RPC could control the wallet led him to build early experiments: dice sites, video poker casinos, and other applications that used Bitcoin as programmable money.
Bitcoin on Slashdot
The second wave of Bitcoin users found the project through Slashdot, which Brekken describes as boomer Hacker News. At the time, the mechanics of the system were more interesting than the speculative price, which swung too much to reason about. He observed that today people move tens of millions of dollars around DeFi on a block explorer, a feat that would be impossible with a traditional bank or PayPal. The instinct that there was no barrier to entry eventually led to SideShift.ai, the direct-to-wallet exchange he runs today.
Looking at the handful of exchanges that existed in 2013, including Mt. Gox and Bitstamp, Brekken asked himself how hard it could be to build one. He found out by launching Justcoin. The experience taught him that while getting started is easy, running an exchange at scale without losing funds, miscounting balances, or getting hacked is incredibly difficult. He eventually sold Justcoin and joined Kraken as an engineer when there were only ten people in the office. For two years he worked closely with founder Jesse Powell, whom he describes as a crypto OG.
A Real Piece of Work
After his time at Kraken, Brekken took a break and swore he would never run an exchange with a bank account again. He described banks as a real piece of work and noted that dealing with them inevitably means dealing with the government. The custodial model also meant sitting on millions of dollars and becoming a target for attackers, a burden that kept him awake watching the money around the clock. This history shaped the non-custodial philosophy behind SideShift.ai.
Brekken calls the swapping on the SideShift site direct-to-wallet because it is easier for users to grasp. He contrasts this with the process at a large custodial exchange: register, wait for email codes, set up 2FA, upload documents, deposit, wait, swap to an intermediate asset, verify a withdrawal address, and finally initiate the withdrawal. These steps are often designed to keep funds on the platform.
There's a big deposit button, but you can never find the withdrawal button.
Exchanges profit from holding balances and retaining users, but Brekken believes a crypto user should always hold their own keys.
More Chains Than Users
The name SideShift originated from Bitcoin sidechains like drivechains and Blockstream Liquid. Brekken expected services would be needed to move value between these separate chains at a time when nobody was using the word bridging. As the industry moved toward a landscape of multiple independent blockchains, the name stuck. He jokes that there are now more chains than users, a fragmentation that created demand for swapping across networks and moving stablecoins between layers.
DeFi pulled in loyal users who wanted trades that are difficult to execute on a decentralized exchange, such as moving from BTC to a meme token. SideShift provides a REST API at sideshift.ai/api that requires no credentials, no forms, and no API keys. This programmatic access allows wallets like Trezor, Edge, and the bitcoin.com wallet to route swaps directly inside their interfaces. Developers can use the API to request quotes and fulfill swaps from any application, receiving affiliate payouts for their integrations.
The Security Arms Race
Smart contract security has entered a faster cycle due to improvements in artificial intelligence. Brekken describes the current moment as an arms race between attackers and defenders. Large language models have become capable of static analysis, allowing observers to send raw binaries or compiled code to find faults. While the past year has been costly for the industry, he expects the tools used to reinforce contracts will eventually outpace those used to break them because there are more white hats than black hats.
One direction for the industry is formal verification, where code is mathematically proven to prevent money leakage or theft. Brekken points to Zcash and its shielded pools as an example, where the newest pool is claimed to be formally verified. He suspects AI tools are being used heavily in this work, as writing formally verified software was previously out of reach for most developers. He suggests that learning to create formally verifiable code will be a significant trend for developers in the coming years.
Machine-to-Machine Payments
The vision for machine-to-machine payments dates back to the Ethereum white paper and yellow paper before the 2014 ICO. Vitalik Buterin wrote about smart contracts paying other smart contracts, a concept that sold Brekken on the project. He once imagined self-driving cars on a congested road using micropayments to negotiate for position based on the passenger's urgency. The rise of LLM-based agents has made this problem concrete again.
Traditional payment rails like credit cards do not scale for agents. A virtual card raised questions about the legal name on the account and whether the card would even be accepted. DAOs face the same barrier: without an office or a CEO, they cannot get a bank account, and without a bank account, they have no cards. Brekken expects a future where individuals use ten different agents, each with a budget to pay for hosting, tokens, and online services. He points to Venice.ai, a project by Erik Voorhees, as an example of a service letting users pay per request with streaming payments via the HTTP 402 standard.